penny the maid

Penny has been busy,,,

2011-01-10T10:39:00.000-08:00

Penny has been busy and apologises for missing her deadline for an update.
Soon.... xxx

Penny's adventures

2010-11-24T07:59:00.000-08:00

Thank you to those of you who have emailed me with such positive comments about my most recent update to my little story (posted as The Contract Pt3). This is just to let you know that I hope to have the next instalment up on my blog by the end of the coming weekend. x

The Contract - Pt 3

2010-11-21T08:15:00.000-08:00

Liz had left for Zurich early on the Monday morning. She is a senior executive with her company, a high achiever, a high earner and her colleagues often talk of her as someone with the potential to get to the very top. Her career has always been hugely important to her, in the early days of our relationship it had become clear to us both that she was destined for greater things than me, but unlike many men I had never been threatened by her success. I was in awe of her and I always felt she relished the fact that whatever battles she had fought during the day at work, she was married to someone who didn't need to be "top dog". I was always aware that I wasn't as macho as other guys, Liz had once told me that when we first met she had thought that I might be gay because I seemed quite effeminate and she had befriended me because she thought I was "safe". It was when she realised that I wasn't emasculated by her success and was happy to support her in her career that we became lovers. Our relationship worked, it wasn't perfect and it certainly wasn't always harmonious but it worked. In social situations Liz was always the dominant partner and it was she who people really wanted to see. Whilst she had great social confidence and could effortlessy energize a room, I was awkward and could never fully engage in the blokeish banter with the other husbands. People didn't seek me out at parties and I think that I probably had a reputation for being difficult and anti-social, I wasn't, I was just incredibly self conscious and unsure of myself. One of Liz's friends once said to me that I didn't seem comfortable in my own skin, I laughed off her comments but deep down I wondered if she had seen into my soul.

Business trips had become a regular occurence for Liz. I used to secretly look forward to her being away because it was at these times that I had developed my little routine of dressing up in female clothing. It was an opportunity to escape and I had been overwhelmed by the pleasure and freedom that I felt when looking in the mirror and seeing myself in her clothes. But then I had been caught and everything had changed. Having recovered from the initial shock of seeing her effeminate husband standing before her wearing her clothes she had siezed the opportunity to really take control of my life. The dynamic in our relationship had changed and now I could see that she was excited about being totally in control and seeing just how much she could exert her authority over another human being. She was the epitome of an alpha female and whilst others might have run for the hills I couldn't escape because I still worshipped her and couldn't imagine life without her.

Liz's absence on this business trip could not be the excuse for me to get in to my routine of dressing up and kicking back. I'd signed the Contract. The Contract was clear. I had to prove that I could last for one month without dressing up or engaging in any identifiably feminine activity. The price of failure would be high, too high. My occasional escapism would become a permanent lifestyle, in a moment of frustration and anger I had signed a document that could change my life forever.

Liz had left for Zurich early on Monday morning, she would be away for three days. She'd kissed me as she left, I was still in bed and wouldn't need to get up for another hour or so. "Don't do anything that I wouldn't do whilst I'm away" she had whispered in to my ear, " there's a good girl, and by the way you know that I won't mind if you want to wear any of my things whilst I'm away, and if you are careful I probably won't find out anyway" she smiled as she kissed me on the cheek and then she left. I heard the front door open and close, she was gone, three days....

I lay in bed thinking.... "good girl"... she was relentless in her insistence that I be referred to as female at all times and I hated the fact that I always felt a rush whenever she referred to me as a female. She had left me feeling horny and she had done it deliberately. I was still wearing the cock cage that she had put on me at the beginning of the month and I had no way of releasing my sexual tension and was ready to self combust!

My phone rang, it was 7.15am, my boss Steve was on the line. He was brief and to the point.

"Don't come in to the office this week, the CEO's son is doing an internship and he is working in our department this week. I've given him your desk so just work from home." the line went dead. Working from home was not unusual for me but I had planned to be in the office because it would at least give me human contact whilst Liz was away. I now faced the prospect of three days on my own... boredom and temptation, a powerful combination.

I worked hard throughout the day, I'm smart enough to know that if you keep yourself busy you leave no room for distraction. In truth I had no choice but to work hard, I was behind on work with a deadline looming so the day passed with alarming speed. Suddenly it was 7.00pm, I was tired and the quality of my work was deteriorating, it was time to eat and to relax.

Cooking for one felt strange, being on my own felt strange, I opened a bottle of wine, I don't normally drink on my own but I had been thrown out of routine and a glass of wine seemed an entirely appropriate response. One glass of wine swiftly became two, now I was relaxed!

After a light supper I decided to end my evening with a nice warm bath, some good music and perhaps another small glass of wine... I felt good, mellow, the pressure of the past few weeks had subsided and the combined effects of Sauvignon Blanc and Norah Jones allowed me to drift into a relaxed state.

I stepped out of the bath and dried myself. I couldn't help but notice that my body hair hadn't returned with any enthusiasm in the past few weeks, I had never been particularly hairy and I had come to like being smooth, it felt sexy. It was probably a combination of the wine, my mellowness and the boredom that sometimes comes with being on your own but having towelled myself dry I wandered into our dressing room, entirely naked and feeling just a little bit frisky. I would never have admitted it to Liz but I missed the way I felt when I was wearing something soft and feminine, it was a feeling like no other and as I stood there looking at the wardrobe I couldn't resist putting my hand out to feel a silk dress on Liz's clothes rail. Suddenly those familiar feelings washed over me, it was late in the evening, no one would ever know, if I just slipped on a couple of items and was careful about replacing them.... the temptation was just too much...and anyway, no one would ever find out.

I found the bra and knickers that Sally had bought me for my birthday. The labels had already been removed so all I needed to do was remember to replace them in exactly the same place after I had tried them on. I stepped into the knickers and as I pulled them up my heart beat quickened, I knew that I would have to put stockings on as well. I picked out a new sheer black pair and reasoned that I could buy a new pair to replace them and Liz would never be any the wiser. I should have just worn the underwear for a few minutes and then covered my tracks, but I didn't, I was excited and all thoughts of consequences had temporarily evaporated. I wanted to see how I would look wearing the little black dress that Liz and Sally had made such a fuss about, and in the heat of the moment I decided to do it "properly". On went a garter belt to hold up the stockings, a black camisole top (just because I loved how it felt on my skin) I stepped into a pair of black patent stiletto heels ( "fuck me shoes" was how Liz described them when she gave them to me) and finally I took the dress off the rail ready to try it on.
It felt wonderful, the chiffon skirt of the dress brushed against my stockings creating an effect that was almost electric, I'd missed this feeling! Liz had bought me a wig some time ago, in the style of a brunette bob cut, and although my hair had grown I decided to put it on. My transformation was nearly complete, I just needed to put on some make up, and I did so unable to resist the temptation to finish my look with a bright red lipstick that contrasted so shamelessly with the black dress. I went back in to our dressing room and gazed at myself in the full length mirror, smiling as I saw the woman looking back at me, I pouted and posed, revelling in the fact that I really did look quite convincing. It was such a shame to think that this would be the last time I could do this, but I knew that to be caught again would be a disaster. I had signed an agreement which clearly stated that I would live full time as a woman if I was tempted to dress during a period of one month. The month was not yet over but thankfully on this occasion I knew that there was no possibility of being caught.

Enjoying the feeling of being Penny again I settled down to watch TV in living room for an hour or so , delaying the moment when I would have to put everything back exactly as I had found it and return to my otherwise dull existence. I must have dozed off but I awoke with a start as the phone rang in the kitchen. It was Sally. "Oh good, I was hoping you'd be at home" she was calling from her car, " I'm just driving by and wanted to drop in to collect the books Liz is donating to our fundraiser for the local hospital. I'll be there in 2 mins, see you soon!" She didn't give me a chance to respond, she disconnected, leaving me in a state of utter panic. Why hadn't I been warned that she might be coming to collect the books?!
Gathering my thoughts as quickly as possible I desperately tried to hatch a plan. I knew that she couldn't come in to the house or have any opportunity to see me. I simply didn't have time to get changed. What an idiot I'd been. Grabbing a pen and a piece of A4 paper I scrawled a note which I would leave on the box " Sally, sorry but I wanted to tell you that I was just going out to have a late beer with a couple of the guys, I'm running late so hope you don't mind me not waiting for you. See you soon! xx" Knowing that I didn't have much time, my plan was to leave the box by the front gate so that Sally wouldn't need to come to the house. Picking up the box I hurried out of the house to the front gate which is at the end of a pathway 15 metres from the front door. If I was quick I'd be able to get back in to the house and turn the lights off and Sally would assume that I was not at home. I was still wearing the stiletto heels, on reflection I should have taken them off , I couldn't move as quickly as I'd hoped, I reached the front gate and just as I set the box down a car slowed near the house as it pulled up to park. Damm she was here already ! Could I get back in to the house without her seeing me?! I couldn't risk it, I had to hide behind a tree and some shrubs and hope that Sally was in a hurry and in no mood to investigate.

From my hiding place I saw her get out of her car and walk up to the gate, she picked up the note that I had left on the box. She smiled to herself and shook her head, my heart pounded as I prayed that she would just pick up the box and leave. But she didn't. She lookd up and glanced towards the front door and could see that I had left it open, she walked along the path to the door and called inside. " Hello... hello, is anyone at home?" She was greeted by silence and to my surprise she entered the house. This was bad news, I hadn't tidied up after myself yet, if she went upstairs she would see some of the clothes that I had got out of the wardrobe whilst thinking about what to wear, they were strewn on the floor, if she went in to the bathroom she would find my make up , open and clearly recently used. I wanted to run away but didn't dare move, my only hope was that she didn't see me. That would leave me the option of denying everything. After several minutes Sally emerged from the house, she closed the door firmly behind her, using her spare key to double lock the door she picked up the box and loaded it into her car before driving away. She hadn't seen me, thank God!.

But she'd locked the front door and I didn't have my keys with me. I was locked out! Wearing a black cocktail dress and stiletto heels in the early part of winter, late at night, I was locked out of my house. My guess was that Sally had also set the alarm before closing the front door, how on earth had I allowed myself to get in to this situation?!

Perhaps a window had been left unlocked somewhere, I walked around to the side of the house chcking each window as I went. Suddenly a voice called out from my neighbours garden, " Hi, are you ok?" it was Brad Jones, a neighbour who had moved in to the area a few months ago. I didn't know him well, we'd had a disagreement over boundary rights soon after he moved in and in the manner of these things our minor neighbour dispute had left a bad taste for us both. For the past few weeks we'd stayed out of each other's way.

He spoke again " Are you ok Miss? Are you locked out, perhaps I can help?" Brad had never actually met Liz and he obviously thought that I was she. I ignored him but he persisted. He'd been in his garden putting garbage in the bins and had obviously seen me trying the windows.

He came right up to our boundary and leaning across he looked right at me as he again asked if he could help. I tried to mutter that I was fine but it was obvious that I wasn't.

" I guess that husband of yours isn't at home right now", he leaned over the wall, smiling, " Hi, I'm Brad, its good to finally meet you" In the darkness I could see his bright white smile, he was a good looking guy, mid thirties, very athletic, he was everything that I had never been, confident and masculine, that's probably why I had made things so difficult for him when he first moved in, I was jealous of him. As he looked at me I could see him adopting a quizzical expression, it was dawning on him that I wasn't what I had first appeared to be. He smiled again but this time his smile had a different aura, it was cocky, he was pleased with himself.

" So, you've somehow managed to lock yourself out, your wife isn't home yet and my guess is that she doesn't know about your err..exotic interests... yet. Looks like you're screwed! I wonder how she'll react when she finds out...it couldn't happen to a nicer person!"

Oh how I regretted our earlier disagreement. I pleaded with him not to say anything.

" I know you don't like me but please don't say anything, it's incredibly important that Liz doesn't find out about this, please, I'll do anything you want, and I promise that I will be a better neighbour. Could I come to your house and borrow some male clothes and call a locksmith?"

"Yeah you can come to my house, we can talk about it there"

Great! Brad was going to help me, the situation could be saved!

He showed me into his house, leading me straight in to the kitchen. As we got in to the light he looked at me and said " Hey you look pretty good, I can see that you've done this before, most women couldn't walk on those heels, I see that you don't mind suffering to look good for the guys!"

I didn't like the way he had said that, I was desperately keen to get out of the dress and put a t-shirt and jeans on. " Do you have some clothes I can borrow?" I asked, hoping to get this all over with as quickly as possible, I was acutely embarrassed and he seemed to be enjoying every second of my humiliation.

" What's the hurry, you look kind of cute, thats a very sexy dress that you have on there. So tell me how important is it that I don't tell your wife about this?"

" I can't begin to tell you how important " I blurted " It would be an absolute disaster, that's all I can say, please, please don't tell her, I beg you"

" There's no need to beg" He sat down on a chair at the kitchen table, " definitely no need to beg, but it does appear that I have the upper hand here. My neighbour, someone who went out of their way to make things difficult for me now has an urgent need of my help. My smug neighbour secretly wants to be a woman. In fact my neighbour makes a pretty convincing woman, a woman who wears killer heels and slutty red lipstick. What is your female name?"

"It's Penny" I said, realising that things were beginning to go wrong again.

" Well Penny, do you know what I always think when I meet a woman wearing lipstick like that? I think of her taking my cock in her mouth and swallowing my load. That's what I think of Penny, I think of her dropping to her knees, unzipping me and drinking every last drop of my cum."

I was speechless.

"So Penny, tell me again how important it is that I don't tell your wife about you wandering around wearing her clothes and flirting with the neighbours? "

I remained speechless.

" Penny, you know what to do. Drop to your knees, there's a good girl, I haven't cum for a few days and I'm ready!"

I didn't want to do it, I had to find a way to stop this. " Look, this is crazy, you know I'm not really a woman, you can't honestly want me to do this.." I couldn't think of anything else to say but I hoped that by articulating that I wasn't a woman would make him see sense.
" This isn't about what you are, its about who you are and what that represents to me. It's about power, and right now I have power over you. I'm going to show you what power I have over you and that my dear Penny is something that I find very, very exciting. He stepped closer to me reaching out to me, touching me, sliding his hand behing my waist, pulling me closer. As he did so he slipped his other hand under the skirt, his fingers tracing my stockings up to the garter strap. " Good girl Penny, how did you know that I like my woman to wear stockings." I gasped as he touched me, fighting back the desire that was building within me. "You may claim not to be a woman but I see a woman before me. You may claim that you don't want to suck my cock but I know that you were born to do it. You dream about it and now you have no choice." My heart raced as he whispered into my ear, " You know you want to Penny, you know that you need to, you know that you have no choice. Make me come, taste my cum and then say thank you."

I had no choice. If he told Liz then my life would change forever. No choice.

I knelt before him as he sat, leaning back in his chair. I hesitated and he took my hand and led it to his groin, resting my hand on the front of his jeans. I could feel his hardness.

" Make it good Penny"

I had no choice. Unzipping his fly I slipped my hand inside and gently stroked him though his boxers. I was shocked by how excited he had become, his cock was rock hard and I had barely touched it. He suddenly stood up and pushed his jeans and his boxer shorts down to his ankles

" Let's make some room for you to get to work on me, Penny" he said as he sat down again.

His cock was now unencumbered and was fully erect. It was magnificent, beautiful even, over 7 inches of thick, cut cock, I couldn't help but be in awe of this good looking, athletic masculine man.

I reached out to touch him, my hand on him, my flesh on his flesh. His cock quivered slightly as I touched him for the first time, Brad sighed as he leaned back, his hand moving to my head trying to draw me towards him. I didn't resist.

I kissed the tip of his manhood, I don't know why I kissed him, I just did it. Then I parted my lips and let my tongue dance around the tip, licking the pre cum and lubricating his helmet. I placed one hand around his shaft, I slowly took him into my mouth. He was moaning now as I started a rythmic motion using my lips to sense every contour of him. I cupped his balls with my free hand, even with two hands I couldn't cover his manhood.

I could feel his hips moving towards me, synchronising with my strokes, " God that's good" he murmured as I could feel his cock getting even harder. "Oh Penny you are a natural! " He was looking down at me, a sly smile on his face as he watched me. " You love it don't you Penny, you love sucking my cock, I bet you want me to fuck you right now"

Those words cut through me like a knife, I didn't want to admit it but I was so turned on, and I wanted him to come. I also wanted him to fuck me. I'd never wanted that before. Liz had been using a strap on dildo on me for a while and only allowed me to come when it was inside me. Perhaps her conditioning was working. I hadn't come for weeks and I had a burning need for this man to slide his cock inside me and fuck me. Fuck me hard. I was shocked that I felt that way but I couldn't help it. I wanted him to take me and I wanted to submit totally to him. What was happening to me?!
He stood up again, but this time he didn't say anything. He placed both his hands on my head, holding me near him as he started to thrust. He was fucking me now, fucking my mouth. His hands were strong and I could feel him tensing as he held my head. My hands were on his buttocks, pulling him to me, I wasn't resisting. My lips were closed around his cock, his shaft riding along my tongue. His stroking became increasingly urgent.

Brad gasped "This is going to be quick, I'm gonna cum" as I felt his helmet swelling, I couldn't believe how hard he was. And then he came. That incredible moment when his cock pulsed and he groaned as he released his seed into my mouth. It was warm and salty, instinctively I swallowed as more of his juice filled my mouth. I could feel some his cum dribbling down my chin, and even in that moment of heightened passion I remember thinking that I didn't want to get his cum on my dress. I swallowed everything that I could. And then it was over.

Brad stood up and looking down at me he smirked as he said " Right, you can get up now, that was very enjoyable thank you. Shut the door as you leave!"

" But what about lending me some clothes and letting me use your phone to call a locksmith? I thought we had a deal"

" The only deal we had was that I wouldn't tell your wife, and I won't tell her. I am a man of my word. As for the rest you just made some assumptions and that was a mistake. You should have have been nicer to me when I moved to the area. Now you are paying the price. Any time that Penny would like to come back and suck my cock she is very welcome, if she is very lucky I may even fuck her but for now I have to ask you to leave. Good luck in getting back to your house!"

It was midnight, Liz was due back within hours, I was standing outside my house,locked out, wearing a black cocktail dress and high heels, I had the lingering taste of my neighbour's cum in my mouth, the temperature was plummeting and it had started to snow. It wasn't supposed to happen this way.... I had to do something...

This weekend...

2010-11-19T08:30:00.001-08:00

The latest instalment will be posted by the end of the weekend x

Beautiful Cocks

2010-11-18T03:41:00.000-08:00

I like these images and I thought I would share them with you.. x

Update

2010-11-15T04:13:00.001-08:00

Thank you to every one for being so patient. The past few months have been a blur and so much has happened. I am working hard on writing updates and hope to post regularly over the

next few weeks. There is much to tell...

Penny x

Update

2010-05-03T05:52:00.000-07:00

Penny is planning to let everyone know what happened to her and will post an update by May 11th. Thank you all for being so patient x

Penny is back!

2010-04-26T01:28:00.000-07:00

Poor Penny....

Wishful thinking...

2009-11-11T06:48:00.000-08:00

In between posting updates I'm afraid that I have been fantasizing about being used and abused again.. I can't quite decide which of the girls in these pictures it is who I secretly want to be most... xx

The Contract pt2

2009-11-08T16:03:00.000-08:00

It felt strange to return to life as a man. I hadn’t fully appreciated just how much my life had been taken over by Penny and her feminine ways. I had got into routines such as regular leg waxing and wearing perfumes and had become used to doing many of these things almost without thinking.
Over the first few days of the month long trial period I constantly had to stop myself from absent mindedly slipping in to those old routines, Liz was watching me like a hawk and I knew that she was just waiting for me to slip up.
I couldn’t really understand why she was so determined for me to fail, it seemed logical that any woman would want her husband to be a masculine male, to provide for her and to fulfil all aspects of the role of husband and lover, just like it had been in our early days together. But Liz didn’t want that any more, well at least not from me.
“Oh Penny darling “ she would say, still referring to me as a female at all times, “ I miss all those girly moments that we shared together, from the first time that I caught you wearing one of my dresses, I knew that deep down it’s what you really wanted. I’m just sorry that I didn’t know about it before, it must have been terrible for you to live this secret double life”
“But it wasn’t like that” I protested but before I could say any more Liz cut across me “Oh you silly girl, I really don’t know how you can say that!” Her tone was patronising but she smiled as she spoke “ Listen Penny we both know that real men don’t wear their wife’s clothes, a real man would never spend a weekend in Barcelona as a woman, for God’s sake you even had a drink in a bar with my sister whilst fully dressed. A real man would have run a mile, you didn’t!” She was warming to her theme but adopted a more serious tone, “A real man wouldn’t have offered to pay his boss to have sex with his wife... do you want me to go on?”
She had made her point, what had started with a mad moment of curiosity as I had tried on some of her clothing when alone in the house all those months ago had become something much more. I felt that I had been tricked and blackmailed into doing all of the things that she talked about but there was no denying the fact that I had done them. It was very difficult for me to argue against it and she knew it.
She spoke again, “ Baby we have had so much fun together since you became Penny, more fun than we have had for years, our relationship works this way, I get to be in charge and you get to be the woman of your dreams, I don’t see why you would want to fight that...”

So it continued, every day Liz constantly reinforcing my femininity, always referring to me as Penny and being negative and hostile towards me whenever I exhibited any masculine characteristics. She had insisted that all my female clothing remain in my wardrobe so that I could see them every morning when I chose my clothes for the day. At first my sheer stubbornness helped me overcome any temptation, I was determined to prove my point and regain some control over my life. As the days went by I found myself taking longer to choose my clothes for the day. I wasn’t tempted to put a dress or a skirt on but as I lingered over my selection of trousers I would run my fingers through the row of Penny’s clothes that were hanging on the rail, I missed that softness, that feeling of silk stockings against my skin, those floaty summer dresses brushing against my legs as I walked... but I wouldn’t be tempted. The price would be too high, I’d signed a contract and if I weakened and was caught there would be no going back this time. It was harder than I’d expected though, Penny had really got under my skin.
One Saturday morning as we neared the half way mark of the month long trial, Liz’s sister Sally came round for coffee. I hadn’t seen her for a while and it was good to see her. I’d always had a difficult relationship with her but when I had become Penny she had been surprisingly warm to me and much more relaxed in my company. She had a wicked sense of humour and although she was fiercely loyal and supportive to her sister and had helped her to trick me in the past, she was engaging company and I liked her. I couldn’t but help remember that time in Barcelona when Liz had persuaded me to go to a bar dressed as Penny. I remembered Sally’s amazed reaction when she saw me there, and I remembered the feeling that it gave me when she looked me up and down from head to toe, a feeling that I had never admitted to anyone, an electric rush of excitement as the thrill coursed through my body. It was the humiliation, the humiliation of being exposed in front of this beautiful young woman, my wife’s sister, that had thrilled me to the core, and every time I saw her I was reminded of that moment and of that feeling.
Sally and Liz chatted whilst we had coffee in the kitchen, it had been a while since they had spoken and Sally was keen for an update.
“So how’s she doing?” she asked, looking over to me as she spoke, a mischievous look on her face.
“She’s trying very hard” said Liz “but I think it’s all so silly, I know that she wants to prove something to me , but I miss having the real Penny around, all this ‘pretending to be a man’ stuff is really very dull.”
I had long since stopped bothering to object to Liz talking about me in this way, it wouldn’t change anything.
Liz then announced that Sally had come round because her husband was away for the weekend and the girls were going to spend the day shopping together. I was told to come along because they wanted me to drive and they wanted my opinion as to what would look good on them. In retrospect it was a mistake for me to agree to go. Throughout the day they insisted on referring to me as Penny and every time they saw a nice dress or a nice top they would say how nice it would look on me. I could see that they were trying to wear me down but I wasn’t going to fall into their trap.
In one store Liz had picked out a beautiful black cocktail dress with a chiffon skirt. “ Oooh” she said “Everyone should have a little black dress” and with that she held it up against me and said to Sally “What do you think?” Sally turned and looked at me as I blushed whilst Liz held the dress up to me, I felt that familiar surge of adrenaline as she spoke “Now that is lovely, Penny, I think you should try it on, black is such a great colour for you, Liz why don’t you ask if they have it in her size?” they both giggled.
“Absolutely not” I protested “ I’ve told you, I don’t do that anymore!”
“Penny you really are becoming such a bore” Sally pouted as she took me by the arm and led me off to another department. As I looked round to see if Liz was following us I could see her chatting with the sales assistant as she handed back the dress. I assumed that she was just asking her to put it back on the rack, I thought nothing more of it and we continued with our shopping. In truth it was a good day, if I set aside the relentless comments about my femininity I could see that Liz and Sally were good together and we shared a lot of humour that day. Liz told Sally that I had my birthday coming up soon and Sally offered to buy champagne in a cocktail bar as an early celebration. Liz and Sally flirted outrageously with the waiters but it was all in good spirits and the champagne flowed, it ended up being a really good day.
Another week passed and I still hadn’t cracked. I was convinced that I would succeed and get to the end of the month and be able to have my life back. I wouldn’t deny that I had been tempted during those quiet moments when your mind wanders, Liz had insisted on me wearing a chastity device during the month long trial period and because I hadn’t been able to relieve myself I found that it was increasingly easy for me to become aroused. Seeing and touching Penny’s clothes every morning was difficult, and privately I missed being able to slip into something more sensual, more feminine. But the price of failure was too high...
My birthday arrived on a Sunday, seven days before the month would be up. I sat at the table in the kitchen with Liz having breakfast when she produced a parcel for me to open. “Happy Birthday darling, I hope you like it” As she handed it to me she kissed me, a passionate, open mouthed kiss, her tongue pushing into my mouth. I was instantly aroused, it had been weeks since the little cock cage had been put on me and I was ready to explode. I pulled Liz into an embrace and returned the kiss with all the passion and fire in my body, but she pulled back and said, “Ooops, silly me, almost forgot your present, come on now, open it up, I can’t wait to see what you think of it. “
I unwrapped the parcel, I should have known of course, as the paper fell to the floor I was left holding that little black dress, the one we had seen on the shopping trip with Sally.
I was about to complain but Liz pressed her finger against my lips and said “ Don’t be angry with me darling, I saw the way you looked at yourself in the mirror as I was holding it up against you, I could see that you wanted it, you just didn’t want to admit it. “ She was right of course, secretly I had loved that dress and had dreamt about wearing it ever since. I couldn’t admit it though, I was so close to finishing the month and the price of failure was so high...
“ Liz you need to understand that I don’t do that anymore, I’m a man and always will be. You can’t change me into something that I’m not!”
“ I wouldn’t dream of trying to change you baby” she purred, “ I just want you to be free to express yourself and allow your true self to come out”
We were both standing in the kitchen, Liz again held the dress up against me as she had done at the store, I protested but she moved much closer to me, pressing herself up against me, we were separated only by the dress as she ran her hands over me.
“ Do you know how much it turns me on to think of you wearing this dress darling ?” she said “ To think of you wearing this with some sexy black lingerie, black silk stockings, with ‘fuck me’ shoes and killer heels.. do you know how happy it would make me if you did that for me? “ She was whispering into my ear, she knew that I had been starved of any sexual stimulation for weeks, I was on fire and she knew it. I so wanted to say yes, but I knew I couldn’t.
Suddenly there was a knock on the door and the moment was gone. Liz went to answer the door and came back with Sally who had arrived unannounced with a small package under her arm.
“Happy Birthday Penny, she almost squealed with delight, “It’s not much but when I saw it I thought of you, I hope you like it” I opened the parcel. Sally had bought me a set of matching lingerie from La Perla. Bra, knickers, garter belt, the whole lot, all in black lace. There was also a pack of black silk, seamed stockings. I didn’t know what to say.
“ I had to guess your size, the store said that they would change if it doesn’t fit.”
Liz interjected “ Oh Sally well done, that will go nicely with the dress I bought her, clever girl! We were just talking about accessories, Penny was getting very excited!”
“Look I’m not going to wear this, how many times do I have to tell you?” I was determined to assert myself.
Liz looked at Sally and smiled “ I’m looking forward to seeing her in these, we’ll have to find a party to go to so that she can wear all her gorgeous new things, she’ll look fabulous and will probably be fighting the men off... I hope she leaves some for us!” They laughed as I looked on in frustrated bewilderment. Liz could see that I wasn’t finding the situation very funny and in order to placate me said that she would take my things upstairs, put them in my wardrobe and that we would talk about it later. Whilst she was upstairs Sally came and sat next to me at the table. She put her hand on my arm as she said “Don’t be angry with me, Liz is so much happier when you are Penny, you know it’s what she wants, why can’t you give her what she wants. You were always pretty objectionable when you were a guy, as a woman you are so different, so soft, so feminine and you look so great. She moved even closer and rested her hand on my thigh as she spoke again “Don’t you miss how it feels to pull on a pair of silk stockings, or when you step into a dress and feel that soft material as it falls around your body? Don’t you want to know what its like to walk into a room and have all the men look at you, wanting you? “ She was gently stroking my thigh now and I was close to the edge yet again..
Liz walked back into the room and Sally pulled back slightly from me, she gave Liz a knowing look and said “ I was just trying to persuade Penny to try the dress on, we all know that’s what she really wants”
“ Oh well, not to worry” said Liz “there are still seven days to go, although I won’t be here for the next 3 days to keep an eye on things, I have to go to Zurich on a business trip in the morning”
“Zurich? I didn’t know that you were going to Zurich..” I said.
“ Didn’t I mention it? I’m sorry. I’ll be away for three days so I am trusting you to be honest with me about how you get on in my absence. I will leave a photocopy of our contract on the table in the kitchen to remind you of what will happen to you if you are caught dressing up whilst I am away.”
“It won’t happen” I boasted,” I only have seven days to go and then I will have proved to you that I am a man and deserve to be treated like a man.”
I’d had enough of the conversation and left the room, leaving Liz and Sally to chat away for another hour or so. Occasionally the conversation would be interrupted by laughter, I knew that they were probably plotting something, but they wouldn’t catch me out,not this time, I was so close.
Later that evening as time for bed approached I found myself in the dressing room, my wardrobe door was open and I could see the little black dress hanging on a rail. I stretched my hand out to feel the material, it was beautifully soft, so light, and the dress looked so stylish. They were right, I really wanted to put it on.
Just then Liz came into the room and seeing me touching the dress said softly “ You know you want to, why don’t you stop fighting it baby, you know you want to. Of course you could always try it on whilst I am away, no one would know that you’d done it... you know that you want to.
She had planted a seed, I did want to, and maybe whilst she was away I could quickly try it on, if I left the price tags on the dress no one would ever be able to prove that I had tried it on, I could get away with it and she would be none the wiser. But I remembered the contract and quickly came to my senses, it wasn’t worth the risk. She would be away for three days leaving me alone to face temptation, I wasn’t going to fail, not this time.

The Contract - Update

2009-10-12T11:16:00.001-07:00

This is just to let you know that alot has happened since the contract was signed. I hope to have time to post a full update by the weekend. xx

The Contract

2009-10-07T01:33:00.000-07:00

It was Sept 1st 2009 and I decided that I needed to have a serious chat with Liz about the way that things were developing. What had started as a punishment for being caught red handed, trying on her clothes all those months ago had become an almost unstoppable change of life and I was desperate to regain some kind of control.
I’d been increasingly upset that Liz would no longer allow me to enter her when we made love . “ I would never allow a girl to do something like that darling, it’s just not for me, give me a strong powerful man every time!” She always laughed it off but I was beginning to worry that she would become interested in finding herself a lover. On several occasions recently in moments of passion she had talked about how wonderful it was to feel a man’s cock thrusting deep inside. She talked about it as if it was something we should both want, and whilst I was worried that she was trying to condition me to want men, I was also aware that I wasn’t attending to her needs and that soon she would find somebody who could.
It wasn’t just that though, I was really struggling with the change of identity and although being Penny could on occasion be intoxicating and thrilling, I knew that deep down I was a guy and the right thing to do, the normal thing, would be to live as a man, a proper husband , and refuse to be Penny any more. I had to reassert my masculinity.
When I told Liz she just laughed at me. “Don’t be ridiculous, we’ve come too far for that, and anyway I know that you love it really, you’re just confused that’s all.”
I decided to stand my ground and repeated that I didn’t want to be Penny any more. I asked Liz to think about it but I wanted her to know that I strongly believed that it was time for me to stop being Penny.
An hour or so later Liz came back in to the room. “Ok, I’ve given this some thought” she said, “you are telling me that you want to be a man again, you want me to treat you as a husband, and you don’t want to be Penny any more. Is that correct?”
“Yes” I replied, unsure as to what to expect
“So after all that you have put me through, and all I have done to support you, you’ve decided that you are bored with this and want to go back to how things were, correct?”
That wasn’t how I saw things at all, yes I’d been caught dressing up, but everything since then had been driven by Liz, either pressuring me, tricking me or blackmailing me into becoming more feminine, but arguing about that seemed pointless right now. My focus was on getting her to agree and for her not to throw me out of the house.
“ I’m sorry” I said.
“ Ok,” Liz replied, if that’s the way you want it I have a deal for you. Interested?”
I sat forward, all ears
She continued “You can try at being a man for one month. During that time you are to dress up as a man at all times, and you are to do your best to behave as a man.” (even in the way she said this I could see her trying to reinforce my femininity). During this period of one month you must not do anything that could be considered female, and I mean anything. You are not to wear any female clothes, make up, wear perfumes, you are not even to read women’s magazines. You must be a man at all times. Is that understood?”
“Yes.” I agreed immediately, it looked like Liz was going to allow my wish.
“Ok, but you must understand that if you fail in anyway, even if it’s something simple like polishing your nails. If you fail then the price will be a high one.”
With that she pushed a piece of paper towards me.
“This is something that I prepared in case we ever had this conversation. I suggest that you read it and sign it”
I read the document.

“I hereby agree that I will spend one month living as a man. I will not wear any female clothing or engage in any activity which could be interpreted as female.
Although I will be living as a man I will make no attempt to make love with my wife during this period. I fully accept that I have to prove that I have earned the right to be regarded both as a man and a husband. During this time I will make no attempt to relieve myself and agree to wear a locked cock cage chastity device which will rstrict my ability to touch myself. The situation will be reviewed at the end of one month. During this month all of my female clothing, make up and indeed all my female possessions will remain where they are now. Nothing will be hidden away and I fully accept that part of my challenge is to resist the temptations that they offer. I also hereby agree that if I fail and allow my femininity to resurface in any way during this time I will fully and enthusiastically accept the following penalties and will offer no resistance or complaint.
1.My forename will be legally changed to Penny.
2.I will never again claim to be male or wear male clothing.
3.I will wear female clothing at all times.
4.I will give full legal authority to Liz and she will make all decisions about my future. I also accept that I will do the bidding of anyone who she gives authority over me.
5.I agree to undergo any cosmetic surgery or procedures (including breast implants, hormone treatment, and hypnotherapy) and give Liz full authority to make those decisions for me.
6.I will never again attempt to make love to Liz and will become her maid and perhaps on occasion her sex slave. I will do as she says at all times, without complaint.
7.I fully accept and enthusiastically endorse Liz’s right to take lovers as she pleases, and to find satisfaction with a real man.
8.I will do everything I can to embrace my femininity and to live a full life as a woman.

Wow, I couldn’t believe what I was reading, it would be madness to sign something like this, and I told Liz as much.
“ Hold on a minute” she said, “I thought you said that you are a guy and that you want to be a guy?”
“ I did”
“So what’s the big deal? Surely all you are signing is a bit of paper that is confirming that you are a guy. Right? Why are you making this hard for yourself? You’ve made it clear that this is what you want and you are obviously confident that you can do it, what’s the harm in signing? I’m giving you what you want!”
She had a point, after all, this was my way out and I had been increasingly worried about things getting out of control. If I signed this contract I could get my life back. The penalties didn’t matter because I wasn’t going to fail. Suddenly it seemed like a good idea to sign.
“Ok, I’ll sign it.”
“Fair enough” she said, I’ll call Sally and ask her to come round so that she can witness your signature. That way it will be a proper legal document.
Sally lived nearby and arrived within minutes. Liz had explained the situation over the phone and as Sally came into the room, a bundle of energy as always, she eagerly sought out the contract and sat down to read it.
“Ooh, this is really interesting” she said to Liz, “It looks like failure is going to be expensive! Tell me one thing, why do you want Penny to wear a locked cock cage?” Liz leant towards Sally and whispered in her ear,they both giggled. Wearing a mischievous look Sally flashed me a smile and wished me luck . I knew that she wanted me to fail but this time I was confident that I would be the one laughing in a month’s time. I was determined to prove them both wrong and my competitive instincts took over as I took the contract and signed with a flourish. Liz and Sally also signed the contract and Sally agreed to look after it for safekeeping.
I wasn’t going to fail, this time nothing could go wrong.....

Updates

2009-10-06T08:00:00.000-07:00

Penny is now back and will be updating regularly (See latest post below). Another posting will be made this weekend. I have much to tell...

Dressing up

2009-08-28T05:13:00.000-07:00

Its been a while since I last posted, sorry, things have been hectic and I simply haven't had time.
We had a quiet summer, carrying on in the pattern that had been established by Liz. She insisted that I spent large amounts of time as Penny and she was increasingly negative towards me whenever I returned to what had now become my male alter ego.
A few weeks ago she came home early from work one day. She seemed to be in good spirits and carried with her various shopping bags. "Hey baby I decided to take the afternoon off and I went shopping with a girlfriend. I got a bit carried away in the lingerie department at Selfridges, Ive got lots of things for us to try!"
I wasn't sure that I wanted this, I was increasingly feeling a need to reassert my maleness and so I tried to dissuade her " Liz, I'm a bit tired today," I said, " do you mind if I take a look at some of this tomorrow?"
She looked at me with a flash of defiance "Hey I've gone to alot of trouble for you today, now I suggest you pour a couple of glasses of wine and come upstairs with me... now!"
I'd learnt that there wasn't much point in arguing with her when she was in this mood so yet again I did as I was told.
Liz threw the bags on to the bed and started to rummage through her purchases. "ooh, lots of lovely things for us to try" she purred in delight, " lets freshen up with a quick shower and then it'll be time to play dress-up!"
I was still feeling reluctant but the Sauvignon Blanc was beginning to ease my resistance. We stepped into the shower together (something that we hadn't done for a while) and began to soap each other in the way that we had done in the early days of our relationship.
My body hair had been removed some time ago and as she was soaping me Liz said " I love the smoothness of your skin now that all that hair has gone, it's so soft, so feminine, so... you"
She never missed a chance to reinforce my self image as being female, but I was trying to resist, I really was.
We soon stepped out of the shower and having dried ourselves, slipped into bathrobes. Liz shot me a wicked smile and gestured for me to join her by her dressing table. "Come on my darling" she said, " Let's fix our make-up before we start trying these things on. Would you like my help or will you do your own?"
I had become quite adept at applying my own make up and to be honest I preferred to do it myself. We sat at the table together, in front of the mirror applying our foundations, blushers, lipsticks. Liz looked at me and smiled "Penny I love having these girlie moments with you, it's such a great way to relax, and you are so good at doing your make up now, you look just gorgeous, I can't imagine that you would be able to walk past a construction site without all the men stopping work to look at you.... anyway, come on lets see what I've bought today."
I couldn't help but notice that Liz increasingly talked about men finding me attractive. I wasn't sure where she was going with that, maybe it just turned her on , but it was always part of her reinforcing my femininity. Part of me secretly really liked the idea of being a sexy woman, irresistible to men, but most of me was still fighting those thoughts and trying to reassert my masculinity.
By this time we had drunk a couple of glasses of wine each. I was feeling much more relaxed and was increasingly turned on as we helped each other into the new lingerie. Liz ran her hands over me as she fixed my bra, we were both wearing stockings, lace panties... her touch was electrifying and I could feel myself becoming aroused. I leaned forward and kissed her, suddenly her tongue was in my mouth and we were kissing tenderly but with passion. I gently touched her, caressing her breasts, kissing her neck, wanting her, wanting her more than I could say...

I could feel myself hardening and my male instincts were beginnning to take over. As we kissed I gently pushed her on to the bed and moved my hand inside her panties, feeling her warmth and her wetness. She sighed as I moved my fingers over her pussy, gasping as I slid one finger inside her, meeting no resistance as her wetness invited me to push further. I was overcome with desire and pulled my panties aside to reveal my hardness, moving myself into position so that I could enter her... it had been so long.

Suddenly Liz stiffened up and pushed me away " Penny what are you doing?" she demanded, all sense of the moment evaporating as she spoke.

" I got carried away" I blurted " I haven't been inside you for so long and I thought that maybe just this once..." Liz cut me short " Oh darling, don't be silly, you're just confused, remember you're a girl now, and there is absolutely no way that I could ever let a girl do that to me.."

"But.." I tried to protest but she placed a finger of my lips, "shh darling, you know that I'm right, its just your hormones confusing you, but its ok, I have a little treat for you that will make you feel better.." she reached across to the drawer in her bedside table and pulled out the feeldoe, the dildo that she used on me more and more. She slipped the bulbous end into her moistened pussy and pulled me gently towards her. She kissed me again, sliding her tongue into my mouth, her hands were all over me, gliding over the silk of my stockings. I was becoming aroused again my hardness returning. Liz drew her hand across my panties, feeling my little erection "Ooh someone's not complaining now" she purred in delight, and as she left her hand resting on my panties whispered in my ear " You want me don't you?"

"You know I want you you " I almost gasped in response, " Good girl" said Liz, as she slid my panties down, at the same moment she reached into her drawer again, this time bringing out a small tube of lube. She dabbed some on my finger and said to me " You'd better make yourself ready for me, you know what to do with that, come on, you know you want to"

So I did as I was told and put the lube on myself, knowing that in seconds Liz would be inside me again.

She made me kneel on the bed as she positioned herself behind me, she brought her hand in front of me and held my little erection , slowly stroking me as she pressed the dildo against my wet hole. "Ooh that feels so good" she said as she slid inside "Doesn't it feel amazing to have a nice big cock inside you?" She continued to stroke as she whispered in my ear " I know this is what you want, its what we both want, to feel how it is when a man takes you, pushing his cock deeper and deeper inside you... Oooh Penny, women like us deserve this, we deserve to have that pleasure, if only you could know what its like to feel a man cum, to feel him pulse and spurt his cum inside, to feel his power..."

I knew what she was doing, she only ever let me cum when I was being fucked now, she was conditioning me to accept it, and to want it. She stroked me harder as she thrust inside me, I could feel myself getting closer to the point of climax, "Yes Penny, you know you want to cum, you know you want to feel a real man, we both do, we both need it, we need to be taken and pleasured by real man with a beautiful thick cock, say it Penny, say it..."

"Yes," I blurted, delirious with passion, and in that moment I came, in fact we both came, my little cock dribbling cum all over Liz's hand.

Liz withdrew from me and we both slumped down on the bed, exhausted. Liz looked over to me, smiling with that familiar triumphant gaze, " Penny you really are such a tart! One minute you are trying to tell me that you want to make love to me like a man despite the fact that you are wearing a matching bra, panties and nylons, and the next thing you are begging for cock! Whatever am I going to do with you!

And with that she rolled over and went to sleep, wearing what appeared to be a very contented smile.

Maid training...

2009-07-29T05:39:00.000-07:00

Liz has sent Penny on a residential maid training course in order to speed up her conditioning. She will be back to tell all soon....

Liz meets Steve

2009-07-11T08:50:00.000-07:00

I was sitting at my desk replying to some emails when my phone rang, it was Steve, my boss.

"Your wife is in reception, go and get her and bring her to my office " It was a command that didn't invite discussion so I did as I was asked and went down to reception to meet Liz.

I took her straight up to his office and after I had made the introductions he said " Look, I know we were supposed to have lunch today but somethng has come up and I am tight for time, do you mind if we have the meeting in here?"

Before I could say a word Liz smiled and said "Sure, I won't keep you too long, but if we are going to do this in the office do you mind if Penny sits in our meeting?"
"Penny?" was Steve's immediate and slightly confused reply, " who's Penny?"
Liz grimaced as she cast me a glance, mouthing the word "sorry" to me as she turned back to face Steve..
" Sorry that was a slip of the tongue, but given that Penny is the reason we are having this meeting, it's probably for the best that you know sooner rather than later"
"Know what?" Steve replied wearing an increasingly perplexed expression. He looked towards me hoping that I might help, but I just stood there in horrified, dumbstruck silence.
Liz sat down before continuing, "Well it all started a little while ago when I got home one day earlier than expected only to find my husband wearing my clothes"
"Wearing your clothes??" Steve edged forward on his chair as he spoke, suddenly very focussed on what Liz was saying.
"Yes my clothes, a dress, my underwear, stockings, make up, the whole lot. I'm sure you can imagine that it was a massive shock to me.
Steve's eyebrows seemed to have moved at least an in inch further up his forehead and he appeared to by finding it hard to suppress a smirk of delight " Yes, that must have been terrible for you, but why are you telling me?"
"Well after I had calmed down we had a long talk and it appears that my husband has a very strong desire to live as a woman. He asked me if I would refer to him as "she" at all times and has also changed his name to Penny. Penny never wears male clothing at home now, in fact she persuaded me to take her on a girls trip to Barcelona to do some shopping and spent the whole trip dressed as Penny. I found it very difficult but am doing my best to be as understanding as possible. Penny has made it clear that she wants people to know about this, she insisted on surprising my sister by meeting her in public when fully dressed, its all been very difficult and very embarrassing for me but I am trying to be as supportive as possible."
I couldn't believe my ears, Liz was manipulating the truth in such a way as to make it seem that this was all my doing. Yes she had caught me trying on her clothes in a moment of boredom at home but ever since that moment she had blackmailed me into dressing more regulalrly, it was she who had surprised me with meeting her sister, and it was she who had insisted that I work from home so that I could be Penny on a permanent basis, all so that she could be in total control!
She continued to speak "The one thing that Penny has been worried about - by the way I hope you don't mind if we all call her Penny from now on - was how you and your colleagues at the office would react. I said that I would come in and have a chat with you in order to persuade you to offer your support"
" What kind of suport do you have in mind?" said Steve, clearly revelling in this moment of revelation.
"Well as Penny goes through her transition to becoming a full time woman I wondered if you would allow her to work from home on a more regular basis. Once she has adjusted and adapted to the course of hormone treatment that she will soon be starting I'm hopeful that you will allow her to return to a normal working environment"
Transition! Hormones! This was all news to me...
Steve adopted a very serious air, " We are an equal opportunities employer, Liz and we are proud of our record of supporting minority groups..Penny will have all the support that she needs" As he turned towards me he smiled, it was a patronising smile of victory. He continued to speak " I have to say Liz that I am very impressed by how supportive you are being. Not many women would be able to stand by their husbands in the face of such shocking revelations"
"Thank you Steve, but in truth Penny has always been very loyal to me, and I feel it is the right thing to do."
Steve frowned, he got up from his desk and went over to his office safe. Unlocking it he removed a piece of paper. What was he doing?!
He spoke in a soft, measured tone, " Liz, I think that you should know that when I came in to work this morning I found this note on my desk, I'm sorry " He handed it to her.
Oh my God... it was the note that Steve had typed up and had persuaded me to sign
" I challenge you to sleep with my wife. If you are successful I will pay you £5"
Steve stepped over towards Liz and put a consoling hand on her shoulder " Liz, I'm sorry that I had to show you this but you have been so supportive and I think that it's important that you know what "Penny" is up to. I hope that you can appreciate that I am not the kind of person who could ever find this kind of macho game playing appropriate, but it's pretty clear that Penny is very confused and needs help."
"£5, is that all I'm worth to you?" Liz looked hurt and upset
"I didn't mean it like that" I was making a pathetic and utterly useless attempt to defend myself.
Steve interrupted once more " Liz, I'm guessing that Penny (he couldn't say my new name without emphasising the P ) simply feels very guilty about the way you have been treated and what you have been put through. I suspect that this note was just a very clumsy way of encouraging me to show interest in you so that you could enjoy the company of a real man. Penny knows that I am 100% heterosexual and proud of that fact. Obviously she is very misguided in trying to make me force myself on you, that's not the kind of person that I am"
He was manipulating her, I could see it but she couldn't! He was sowing seeds, telling her he was a "real man" "100% heterosexual" and on top of that a caring thoughtful person.
"Thanks Steve, I think you are being very generous to Penny in saying that, its such a shock to see that note, I need to think about it, and what effect it will have on my relationship with Penny in the future.
She stood up to leave, I stood up at the same time but Steve told me to sit down and wait in his office. He escorted Liz back out to the reception area and came back 5 minutes later and resumed his position behind his desk.
" Well Penny, what an interesting meeting that was!" he said in triumph, " All these years, I had no idea that you were a closet gay! How amusing"
"Steve its really not like that"
He cut me short " To be honest I don't really care. I find it quite amusing that you like to play at being a girl..However Liz may think that you are her sissy, but the reality is going to be quite different. From now on you will be MY little sissy fag. If you want to keep your job, you will do everything I say at all times, is that clear? If you fail I will do everything in my power to ensure that you never work in this industry again. You will be ruined. Have I made myself clear?"
"Yes Steve" was my meek reply, I could sense that I was beaten and in no position to argue with him.
"And never call me Steve again, from now on when you speak to me you will call me Master, is that understood?!"
"Yes Master" I knew that Steve was a confident alpha male but I'd never seen this side of him before.
He continued speaking " It's no secret that I have always fancied your wife, and thanks to your complete stupidity I'm going to have her.
She doesn't know it yet but I'm going to take my time and gently reel her in. Whilst you are prancing around dressing like a sissy I'm going to fuck her. I'm going to fuck her like she has never been fucked before and I'm going to do it in my office, in your house, in your bed, in the back of your car, I'm going to make her beg me to fuck her and I'm going to make sure that you know about every second of pleasure that I give her. Every time that I have fucked her I'm going to ring you so that you can thank me for giving her something that you never could. Just make sure that you leave your phone switched on.. I'd hate for you to miss any updates."

Later that day I arrived home, still trying to come to terms with how my world had changed so utterly in such a short time. It didn't seem so long ago that I was just a regular guy with an ordinary life but how dramatically had everythig changed when I'd made the fateful mistake of trying on my wife's clothes and getting caught. My wife had forced me to become more feminized and seemed to have no qualms about blackmailing me to accept more and more female conditioning. My boss now knew and had told the entire workforce that I was to be treated as a woman at all times. Worst of all it turned out that he was a lecherous bully and he was planning to take my place in the marital bed.

I walked through the door to find Liz sittng in the kitched drinking a glass of chilled white wine. she looked gorgeous and I found her as attractive in that moment as I always had.
I knew that I owed her an apology for the note and immediately told her how sorry I was.
She was surprisingly clam and just said to me..
" Penny I've given it some thought and I think that Steve is probably right. You've been confused and given that you clearly can't offer me the things that only a real man can you got it into your head that you should persuade someone else that they should . Penny you are a silly girl and you have made a mistake and I forgive you. I can appreciate that you see Steve as a very attractive and desirable man but he has made it clear that he is not the kind of man who pursues other peoples wives. he's too nice for that. For my part I still love you and am not the kind of woman who would sleep with someone just because they are very good looking. Let's just regard the matter as closed."
I knew that the matter wasn't closed but had no choice but to agree with her.
"Oh and by the way we had a delivery today, I'd ordered some lingerie and sleepwear for you from Victoria's Secret. Look at this isn't it lovely? "
She showed me a black babydoll , some sheer stockings , and some lace panties.

" Be a good girl and try them on for me?" she said. I didn't want to, the reality of being a girl ,the total lack of control that I had in my life , and the realization that this wasn't a game was sinking in very fast. I wanted to be Liz's husband again and to do things that men do for their wives but
Liz had taken the opportunity to move on and it was all too late for me.
Liz joined me in the bedroom as I tried on the new clothes.
She beamed as she looked at me, "Oh Penny you really look such a temptress! If I ever let you out the guys will just be queueing up for you!"
I began to protest but she laughed and stepping closer to me slid her hand inside my panties..
"Oh I can feel that someone is pleased with how today has gone!"

She's going to meet my boss.

2009-07-08T09:42:00.000-07:00

Liz wore a contented smile for several days after our return from Barcelona. It seemed that she hugely enjoyed exerting her control over me and every time that she tested me and came out on top it reinforced her enthusiasm for taking us both down this path. It had been only moments before we were due to leave our Barcelona hotel to go to the airport that she finally relented and gave me back my chinos so that I could make the journey in some male clothing. Even then I was forced to compromise as she gave me a tailored red silk top to wear as well. It was extremely feminine and I felt incredibly self conscious. Liz also seemed to find it highly entertaining to insist that I wore some fake pearls and a set of bra and panties underneath the top.
“Liz I can’t wear this, I’ll look ridiculous, this top is obviously made for a woman and anyone who gets close to me will be able to see that I’m wearing a bra ” I had protested.
“ Oh don’t make such a fuss darling, “Liz had replied, “ It looks fine, and anyway given that you have been wandering around Barcelona wearing a collection of my summer dresses for the past few days you’ll forgive me if I don’t take your protests too seriously!”
We arrived back in London in one piece although throughout the journey I felt the stares of strangers and heard whispered conversations and muffled laughter. On the plane the hostesses had taken it in turns to attend to us and were clearly amusing themselves by trying to work out whether I really was wearing a bra. I sat quietly, dazed and confused. Utterly humiliated at my plight yet incredibly excited as I cast my mind back to the memory of how it felt to spend three days as Penny.
On Monday I returned to work, dressed in my male clothes and restored to my male persona. The day went as normal until late morning when my boss, Steve, called me into his office.
“ Your wife has called me and has asked to meet me for lunch later this week” he said, “what’s it about”
“Err, I’m not sure” I replied rather hesitantly , “ I think she wants to speak with you about the possibility of me working from home on a more regular basis”
“So why do you need your wife to have that conversation with me” was Steve’s abrupt reply, “Who wears the trousers in your house?”
I was trying to think of a way to answer that particular question when he continued “ I guess she probably just wants to meet me! All the woman do in the end, they can’t help themselves!”
God he was so arrogant. He had an easy charm which on occasion was quite attractive but he had incredible self confidence. I remembered having a drunken argument with him several months earlier when he had insisted he could get any woman into bed if he put his mind to it. I’d told him that he was being ridiculous and was living in a fantasy world but he had just laughed at me. “ Any woman is beddable my friend, you just have to work out what they want and then give it them. I bet I could have your wife if I wanted to”
I told him very forcefully that Liz wasn’t that kind of girl and that she was far too choosy anyway. He just laughed at me, “Sure thing buddy, believe what you want to believe”
That had been several months ago and now here we were in his office facing the prospect of him having lunch with my wife.
I could tell what he was thinking and blurted out to him “ Steve there’s no way that she’d ever be interested in you, she seeing you because she wants to see more of me!”
“Oh so you remember our little conversation and you think that I’m not good enough for her do you?”
“That’s not what I meant, I just think that if you try it on with her you’ll get nowhere”
Steve’s reply was instant “ You know I wasn’t going to try it on with her, but now I feel compelled to. Shall we have a bet on it?”
I replied saying that I thought that wasn’t a good idea but Steve was rising to the challenge now and reminded me that I thought that he had no chance of success so what was there to lose in me agreeing to a bet? His logic was simple and straightforward,
“I’ll make it easy for you” he said, “ shall we say £5. “ winner takes all!” and if you agree to the bet then I will be much more likely to agree to Liz’s request for you to do more homeworking when I see her ,“
He went to his desk and began typing on the keyboard. He pressed the print key and passed the resulting sheet of paper over to me with a pen. It said in bold letters “ I challenge you to sleep with my wife. If you are successful I will pay you £5.” I probably should have paid more attention to the wording but I signed the paper where he told me to. I thought it was all a macho charade and he would never follow through and if he did that he wouldn’t succeed.
Steve locked the paper in his office safe. “In case you are wondering I’m locking this away just in case I need it in the future, you see I fully intend to seduce your wife, I will take her to the point where she is begging me to fuck her, and when you complain or try to stop me I will be able to use this against you. In fact I may need your help and now that I have this piece of paper I will expect you to help me or face the consequence of having the document made public.
I was stunned into silence, I’d allowed him to manipulate the situation so that it would appear that the whole thing was my idea.
Steve then stood up as if to close our meeting and as he showed me to the door he said to me
“ I’ve had another thought... just to make things interesting I’ll call you when I’ve seen her. Don’t answer your mobile. When I call I will allow the phone to ring once if she has agreed to see me again, twice if she has agreed to come to my apartment, three times when I kiss her passionately for the first time, and if it rings four times it’s because I have just given her an orgasm.” He was smiling but had a fiery look of determination in his eyes, I could see that he wanted to demonstrate his masculinity and his superiority to me.
I left his office unsure of what I had started but certain that once again I had no control over what was going to happen.
I got home from work that evening and found that the house was empty. Liz had left a note saying that she was meeting Sally for drinks and would be back later. I liked having the house to myself, it gave me an opportunity to relax and not have to worry too much about showing resistance to Liz about becoming Penny. I went upstairs to the bedroom and took off my suit and stepped into the shower. When I came out I sensed the emptiness of the house and as I was alone couldn’t resist the temptation to become Penny again. She was becoming an ever present in my life and gave me a feeling of relaxation and contentment that I couldn’t find elsewhere.. A plain white silk blouse, a grey skirt, some very sheer stockings , black high heels and some lipstick and once again Penny stood before me in the mirror. I spent the next hour or so watching TV and drinking chilled white wine. I dozed off and was only woken by the sound of Liz’s key in the front door.
“Hi honey I’m home” Liz called as she came through the door “ and Sally has come back to pick up a book that I’m lending her” I sat bolt upright in shock, not again!
At that moment they both walked into the room, only to stop in their tracks when they saw me.
Liz was the first to speak “ Hah, do you see how things are Sally? As soon as she gets home she can’t wait to get out of her work things and get dressed. I’m seriously thinking about throwing out the male clothes, they aren’t being worn and they are just taking up space. So much for having a husband!”
Sally was smiling as she said “ I know Liz but she’s so cute, and once she’s trained just think of all the household chores that she’ll do for you. I think we need to find you a real man though, you have to start thinking about yourself”
“Oh I’m not ready for that yet” replied Liz ( did I hear correctly, did she use the word “yet”?). At the moment I’m just trying to get used to having another woman in my house. And for all her faults I still love her, I’m beginning to see a side of her that I really like, a side that I never saw in my husband, life may be different but now that I’m in control I think it will be better.”
Sally left and I went into the kitchen to fix Liz a drink. Liz followed me and as I was pouring her a glass of wine she moved closer to me and standing behind me put her hands around my waist gently holding me.
“ I love what you are wearing darling, and you are really beginning to develop a look that works for you .. look at us , you look gorgeous in that skirt and you have legs to die for! You look so glamorous and sexy and here I am wearing a pair of jeans and a sweater, this really is a role reversal! ”
It was a nice compliment and I thanked her because despite still feeling quite awkward in women’s clothes I did think I was becoming more convincing everyday and I was desperate to look good.

She was running her hands over my skirt and feeling my stocking tops, “ I think that you should always be Penny at home now darling.....always....” my heart skipped a beat “ we both know that its’ what you want” She was pulling me closer to her and I could feel she was becoming aroused..
“ I’m feeling horny baby, do you think we should fuck?” Wow what a question! I hadn’t been inside Liz for an age and was very definitely ready to make love with her.
“Ooh yes, I’d love that” I replied breathlessly, “Good “ she said, I’ll be back in a moment.
Liz was gone for a moment or two and came back into the room with a large double ended dildo , and a tube of lubricant.
She saw the look of surprise on my face. “Oh baby did you think that you were going to do the fucking? That’s so silly, you know that only a real man could ever have me in that way. I made a purchase today and I think it may be fun. It’s called a Feeldoe, it’s actually made for lesbians to use on their lovers because they both get pleasure from it, it should be just fine for us. Mistress Grace is adamant that you should only have an orgasm when you have been penetrated, its all part of your conditioning, its all in your best interests, trust me!
She had her hands on me again, caressing me, kissing me, her touch felt so good, she slid her hands down the back of my skirt, pressing herself against me, “ Turn round baby” she whispered into my ear.. I didn’t resist, I turned and with my back turned to her she ran her hands across the front of my body, feeling my bra through the silk blouse, “Bend over the desk baby “ another whispered command . I leant forward, resting my hands on the desk. I could hear her unzipping her jeans and heard her sigh as she placed the bulbous end of the dildo inside her, “ Oh baby I want you so much “ she said to me as her hands gently lifted my skirt, exposing my stocking tops and my white panties, I felt the coldness of the gel on her finger as she prepared me to take her manhood and I gasped as she guided it into me, sliding it gently in and out, deeper and deeper, rhythmically stroking us both as she held me with her hands on my hips pulling me back onto her cock. I felt her shudder as she climaxed so quickly and she reached around me to feel the hardness of my own little cock.
“ You love it baby don’t you? You love it when you have my cock inside you don’t you? This is how girls like to come. You want to come don’t you?”
I came, and I came hard. It was the first time I had come in a long while and I could barely stand.
Once more Liz had her now familiar air of triumph. I knew what she was doing. For her it wasn’t just about me dressing as a woman, she was going to make me become one, and make me want everything that women want. Not only was I powerless to stop it, I secretly loved it.

“By the way, I’m seeing your boss for lunch tomorrow, Steve is his name isn’t it? What’s he like?”

Daydreams...

2009-06-14T04:00:00.000-07:00

I thought I would upload some photos that I have found recently whilst surfing the web. I think its fair to say that there isn't a girl in any of these pictures that I wouldn't love to be...

Barcelona part 2....

2009-06-12T01:58:00.001-07:00

Liz seemed to be revelling in her new role as Queen of our little world. In all the time we had been together I had never seen her so energised and so obviously excited and amused by the power that she had over me. Confidence oozed through her.

It didn't take long to get ready. Liz handed me some beautiful white underwear and a white linen dress, saying to me "lets keep it simple tonight, its your first time in public and its probably best for you to wear something that doesn't draw too much attention.."

I was excited yet terrified as I pulled the stockings over my recently waxed legs. I stepped into a pair of summer sandals, brushed my hair and put on my now customary Alice band and stood back from the mirror, taking in the image before me.

"Have you decided where we are going tonight?" I asked, "Do you really think that I can get away with this? Surely people will look at me and know?"

Liz stepped towards me and put her hands on my shoulders, looking me in the eye as she said "Penny you'll be fine. You haven't perfected the look yet but in this town there are different and interesting people in every bar in every street, you'll blend in just fine. As for tonight I thought we could start by having a drink in the bar and see how the mood takes us. Now come on, don't forget your lipstick, its time to go.

We left the room and headed into the great unknown. As we stood waiting for the lift I was struck by how beautiful Liz was. She had an effortless elegance, wearing a pale green cashmere top and white cotton trousers she barely needed make up, and carried herself in a way that only seemed to highlight my clumsiness. "Don't worry" she said, obviously sensing my anxiety " you look great, just relax and allow the woman in you to come out... you know you want to" Another knowing smile "and of course lets not forget that I have some very interesting tapes and photographs, it would be a shame if you refused to do as I say and I had to make them public wouldn't it Penny?!" There it was, the reminder that this was all non negotiable.

We walked together, arm in arm to the bar on the ground floor of the hotel. Liz found us a table tucked away in the corner, and I sat with my back to the room as Liz ordered a bottle of champagne.

"Oh waiter, would you bring three glasses please, we are expecting one more person to join us?" she said

"What?!" I blurted, "what do you mean? you didn't say anything about us seeing anyone else, who is joining us?"

"Oh, I'm sorry, I must have forgotten to tell you, " she replied "my sister Sally is in Barcelona this weekend with a group of girlfriends , she's going to have a drink with us before joining her frinds for dinner later"

"You must be joking! I can't see Sally, not dressed like this! I'll be humiliated. Please tell me that you are making this up!"

At that precise moment Liz's sister, the beautiful blonde who I had always secretly fancied but never really got along with ,arrived at our table and greeting Liz with a hug and a kiss turned to me and simply said "WOW"

There was a brief pause, it seemed like an eternity as my heart rate went through the roof and I was convinced that I was a heartbeat away from fainting on the spot.

"Oh my God, Liz you were telling the truth! I would never have believed it if I hadn't seen this with my own eyes, Of all the people in the world...I would never have guessed.. I need a drink!"

She was smiling as she spoke, in fact Liz was smiling too, suddenly I felt like I had again walked into a trap and hadn't seen it coming.

"Sally meet Penny, Penny meet Sally" said Liz with a triumphant air.

"Penny you have no idea how good it is to meet you" said Sally with an unmistakeable smirk, "Liz told me that she found out that you like to dress up but I didn't believe her when she said that you were so keen that you'd go out in public, Oh my God, you have even plucked your eyebrows, ooh and you've waxed your legs, Penny is well and truly out of the closet! Liz I really would never have guessed that your husband was gay , how do you cope with that!"

"But I'm not gay.." I'd barely got the words out when Liz interjected

"To be honest Sally I was shocked and angry when I first found out, but after I'd thought about it for a while I realised that it was a situation that I could turn to my advantage, and to be honest I have to admit that I've quite enjoyed seeing just how much control I have. You see once you understand that you are dealing with someone who might protest a little but in truth just adores being a woman and will do anything to be allowed to be a woman then the rest is plain sailing. Its only been a few weeks but the house has been signed over to me, the bank accounts are all in my name. Penny has agreed that I no longer have a husband and in order to stay in my house she accepts that she is my companion and housemaid"

"Housemaid!" Sally could barely conceal her amusement, " Ooh please tell me that you've bought her a uniform"

"But of course darling" Liz replied.. they were giggling like schoolgirls and I was looking on in stunned silence.

"But what about the day job? Surely even you wouldn't make 'Penny' go to the office.

"Well I had thought about it, and it is tempting but I have decided to speak with Penny's boss to see if she can work from home on a full time basis. I'm having lunch with him next week to discuss it"

I couldn't believe my ears, my wife had arranged to meet my boss to persuade him to let me become a home worker and she had done this without telling me. They were talking about me as if I wasn't there.

"So you are pretty serious about pushing on with Penny becoming a full time woman then?"

" Well you know me, I see things in black and white, Penny loves being Penny and is actually a nicer person to be around than my ex husband so it seems to make sense for it to become 24/7. It also puts me in aposition where I can get on with my life and do things that suit me, as and when I want to. Its a win win situation. I also have a friend who is a Dominatrix, she is whipping Penny into shape for me and is being very pushy about seeing just how far we can take the transformation"

"Really , what does that mean?" Sally asked

" It means that you should never mess with a dominatrix! "said Liz " She wants to go the whole way with Penny and give her hormones, boobs, the works!"

"Bloody hell, you can't do that can you, surely... can you?" Sally had a look of delight and sheer amazement on her face"

"We'll see, to be honest I've been quite surprised by how Penny seems to have embraced all of this. She may claim not be gay but I can tell you that she likes her men to be big and strong, and is desperately keen to please"

"You're kidding me"

"Its all on tape Sally, poor Penny didn't realise that she was being filmed. I've promised not to show the tape to anyone as long as she does as she is told."

"How wonderful" Sally was loving every second of this, " You must let me know how you get on, I hate to say it but I have to leave now or I will be late to meet my girlfriends for dinner. I can't wait to tell them. I think a couple of them knew your husband before he/she became Penny, we'll have to see if we can arrange for us all to get together for a girls night out before we leave Barcelona!

"Sounds like a great idea" said Liz, that triumphal air returning " and of course I'm thinking that when Penny has completed her maid training she might have some spare time that can be utilised by hiring her out to work for friends or family. Do you think that might interest you?

"Ooh Liz, you read my mind !" Sally replied, " that would be such fun!"

Barcelona.

2009-05-26T08:04:00.001-07:00

I got home in the early evening of that eventful Friday expecting to see Liz but all I found was a note on the kitchen table saying “I’m out with the girls tonight, don’t wait up! x” After everything that had happened it seemed unreasonable for me to complain, but I was disappointed because I felt the need to talk with her. So much had happened so quickly and I was confused and feeling totally out of my depth. The next day we were due to go away together for a few days so I figured that would give us both an opportunity to draw breath and get some normality back into our lives. To be honest I was looking forward to leaving my new alter ego of Penny behind for a few days.
The next morning involved the usual pre travel blur of activity, packing suitcases, checking tickets, confirming taxi rides to the airport etc. The plan was to fly to Barcelona for a long weekend. Liz had arranged it and had booked us into a lovely hotel , le Meridien near the busy Las Ramblas district. Her planning was always meticulous , our driver turned up on time, we got to the airport on time and it was only when the driver unloaded our bags that I realised that my bag wasn’t there. Liz was quick to reassure me, “Don’t worry, I decided to take one big bag rather than two smaller ones, I put all of your things in for you”
“ Oh ok, thanks” I replied, thinking nothing more of it.
The rest of the journey went very smoothly and we were soon at our hotel . It was early afternoon and our plan was simple, shower, get changed and head out for a glass of something fizzy in a nearby bar so that we could work out our plans for the next few days.
Liz showered before me, and as I undressed in readiness to use the shower after her I put my discarded clothes into a laundry bag. I’d worn cream chinos during the journey and they looked decidedly grubby. I figured that hotel laundries usually do a pretty good job so I made the call to housekeeping and put the bag by the door.
I went into the bathroom whilst Liz was still in the shower. She has a fabulous body and looked irresistible as she massaged herself with soapy lather. Taken by the moment I stepped into the shower to join her, my cock already semi erect in anticipation.
“What are you doing baby?” she said in a quizzical way. “Well I thought...” I replied, but she quickly interrupted me, “ Penny, you need to understand that we have agreed how things will be between us, this isn’t a game that you can play by your rules whenever it takes your fancy. You have admitted that you like being a female so as far as I am concerned you are one. Now stop being silly and let me finish my shower.”
What she had said shocked me because despite the intensity of the previous few weeks I had seen it as an extended fantasy game. I really hadn’t considered the possibility that this was something that was destined to change our life together in any kind of extreme way. I still thought that Mistress hadn’t yet told Liz about the events of Friday with the delivery guy. We’d left for Barcelona so soon afterwards I assumed that they hadn’t had time to speak, and any way Liz hadn’t mentioned it. God if Liz did find out there really would be no going back. Suddenly the enormity of the situation was beginning to hit home.
I decided not to push the point with Liz and just to go with the flow a little. The plan had always been to use the time in Barcelona to relax and enjoy some time together. With that in mind I waited my turn for the shower and then spent the next 15 mins or so with the water on icy full blast and emerged cleansed and invigorated.
Liz was dressed, made up and ready to go out as I stumbled around the room searching through the cupboards looking for my things.
“What’s up baby?” she smiled,
“Just looking for my things”
“ I unpacked for you” she said, “its already in the wardrobe and your underwear is in the second drawer down in the chest of drawers”
“Thanks” I replied but as I opened the second drawer I immediately realised that she had made a mistake.
“Liz this is all your stuff...”
“I don’t think so baby” she replied as she came over to peer into the drawer “ No, those are definitely your things Penny, mine are all in the top drawer”
The drawer was full of ultra feminine underwear that I had never seen before. Looking at the labels most of it seemed to be from Myla’s boudoir collection, http://www.myla.com/boudoir/
I went to the wardrobe and again there was no sign of any of my clothes. All I could see were Liz's clothes, a mixture of dresses, tops and skirts, some of which I'd not seen before.
“ Liz, what’s going on?”
“Oh Penny, relax,” said Liz smiling at me, “ we are in Barcelona, miles from home, nobody here knows you. The only male clothes that made the trip were the ones that you were wearing and they are in the hotel laundry now. You should be grateful that I went to a lot of trouble to buy some lovely new clothes for you. I’m so looking forward to having a long girls weekend with you!”
“But this is crazy, I can’t do this, I didn’t mean for things to go this far, for God’s sake Liz you can’t be serious...”
Suddenly she wasn’t smiling any more “I’m very serious Penny, I have said this before but your desire to play at being a girl has given me an opportunity of take charge of my life. That is an opportunity I fully intend to take. You will submit to me, and you will do everything that I tell you. Your role is to be my companion and not my husband. Real men don’t wear dresses do they Penny?”
“Well no, I suppose they don’t” I replied
“And men don’t wear bras and panties, or stockings and high heels do they Penny”
“No Liz,” I wasn't comfortable with the direction this was heading in..
“Oh, and of course men don’t dress as maids to seduce the delivery guy do they Penny”
She knew! Dammit she knew.
“Men don’t do any of those things do they Penny? Isn’t it women who do those kind of things Penny”
I was finding it hard to disagree with her, she was using words to make me agree that I wasn’t a man and I was so confused. It was at the moment that she reached out and took my little cock in her hand. She started gently stroking and it felt so good. “Stop resisting me Penny, you know how you want this. You love it when you dress up don’t you Penny?”
I wanted to say no but I could feel my little cock getting harder and harder as she caressed it..
“And you want to wear a dress for me now don’t you Penny, and you want to wear your highest heels so that we can go out and tease some sexy Spanish guys don’t you Penny?” she continued to stroke me and I could feel myself building to a crescendo..
I knew that I shouldn’t be letting this happen but I couldn’t stop it, she was completely in control..
“Your Mistress told me what happened on Friday Penny, she told me how you allowed the delivery guy to sweep you off your feet and take you upstairs, did you know that she had filmed it all. She showed it to me on Friday night. I saw how you let him carry you to the bed Penny, I saw how you wrapped your legs around him as he climbed on top of you, I saw how passionately you kissed him, how you slipped down the bed and took him in your mouth. I saw how you made him come so quickly and how you took every last drop of cum from him Penny. I saw what a good girl you were Penny, you enjoyed pleasing him didn’t you and you want to do it again don’t you Penny, because you like being a girl don’t you Penny?
She was stroking faster now and at that moment my little cock erupted in orgasmic convulsions.
“Hah, I think we have our answer” Liz said triumphantly, “Penny, after all of this can you see how I would find it difficult to see you as a man” she said, “ but I think it’s wonderful that we seem to have similar taste in men, in fact I have to admit I was quite jealous watching you on that tape as the delivery guy had his way with you. Lucky girl!”
“Now come on, that’s enough talking for one night, Barcelona is a party town and I think that Penny and Liz should find a party! “
“I’ll help you with your make up...” she said as I realised that for tonight at least resistance was pointless.
To be continued...

Holiday

2009-05-17T04:44:00.000-07:00

Sorry that I haven't posted in the past couple of weeks. I am currently on holiday with Liz . Its quite an adventure. I will be back soon to tell you all about it.

Watch this space !

Penny x

Friday

2009-04-29T05:00:00.000-07:00

As usual I arrived at my Mistresses' house on time on Friday, and as usual she looked immaculate resting on her chaise longue, issuing commands in such a confident effortless way. I had learned at an early stage that her word is law, and anyway I had been forced by my wife Liz to sign a contract agreeing that I would accept without question that both Liz and Mistress Grace had complete control over my life and all decisions. I knew that they found it amusing that it was so easy to control me and whilst Liz kept telling me how much she loved me I always thought that Mistress Grace just saw me as a plaything. They had photographs though, and the threat of public exposure meant that I had no choice but to do as they said, even if they seemed to be leading me down one way path...
As soon as I arrived at Mistresses' house the routine was that I would immediately go upstairs and change into my maids uniform. Mistress told me that it was important to wear a uniform so that everyone would be able to clearly understand my place in the pecking order.
Although my Monday to Thursday existence still involved working in a busy office as I had always done, Mistress insisted that Fridays should be entirely feminine days. My legs had long since been waxed and although I wouldn't admit it I had come to love the feeling of pulling silky stockings over my perfectly smooth skin. I stepped into the uniform, put an Alice Band in my hair, applied my red lipstick in the way that I had been taught, and went downstairs to report for duty.

My working day on Fridays had become fairly routine. Mistress had given me a schedule which included the laundry, dusting and hoovering the house and of course doing the ironing. She said that it was extremely important for me to show my value to my Mistress at all times and she certainly had no intention of doing any household chores herself. It was only after I had completed my chores that she would start with other aspects of my training or "attitude adjustment" as she called it, but I will tell you more about that on another occasion.

Anyway on this occasion I was busying myself with some ironing when Mistress walked in to the room and told me that she was going out for a while and would be back later.
"Oh by the way, I'm expecting a delivery of some garden furniture later" she said, "if they turn up while I am out you must make sure that they take it through to the back of the house and assemble it before they leave."

I panicked and protested " But I can't answer the door dressed like this!"

"Penny, if you fail to do as I ask then you will have to be responsible for the consequences. This is not a joke, and its not a game. You are my maid now and if I want you to take a delivery for me then you will do it without question. Do I make myself clear?"

"Yes Mistress"

"Good girl, it would be such a shame for your work colleagues to see some of the photos we have of you now. If the door bell rings I expect you to answer it without hesitation. In the meantime you have ironing to finish". And with that she turned and left the room, left the house, and left me in a state of near blind panic.

I continued with the ironing, it was a sunny day and with the windows open a gentle breeze fluttered through the room. I figured that delivery firms are notoriously unreliable and anyway I calmed myself with the thought that Mistress was probably just having a joke at my expense and that no one would show up at the door. I turned the radio on and soon became lost in another world, listening to old songs and indulging in absent minded daydreams. As I stood there with the soft satin of my dress brushing gently against my thighs everytime I moved , I began to think about what it would have been like if a delivery man had turned up. What if he was big and powerful, and mistaking me for a real girl had taken me against my will? I was shocked by how turned on I became, and I remembered the hypnotic conditioning that my Mistress had imposed on me early in my training. She had told me that I would start to fantasise about men. I had dismissed it as silly and pointless, just part of a game, but here I stood, only a few weeks later, my pulse quickening at the thought of what might have been...

Suddenly I was snapped out of my day dream by a loud knock at the door. I froze. Mistress had a set of keys so I knew that it couldn't be her. There was another loud knock at the door and as I cowered in the hallway I could see through an open window that there was a delivery truck parked on the drive. My heart rate went through the roof. Mistress had left me in no doubt that I had no choice but to open the door. If I failed she would tell everyone my secret and the photographic evidence was excruciatingly embarrasing. My career would be ruined and any humiliation would be far greater even than what I would suffer in opening the door. At least the delivery man wouldn't know who I really was. I decided that the worst thing that could happen would be that he would laugh at me, perhaps make a joke and then get the hell out of here!

I took a deep breath and opened the door.

He was gorgeous. 6ft 4 ins tall, maybe mid 30s, very muscular, wearing a tight shirt with cut off sleeves and blue jeans.

He smiled at me " Hi!" he said, I have a delivery for you, where do you want it?"

"Oh, can you take it through to the back of the house please" I stuttered as quietly and softly as possible, " My Mistress has also asked me to remind you that she would like the furniture assembled"

"Your Mistress?" he smiled again, " So you aren't the lady of the house then? Is she not here to sign for the goods?"

" No I'm afraid not" I replied, "I'm not sure when she'll be back"

"Thats fine by me, you'll do nicely!, I'll get the things from the truck"

I couldn't believe it, he had reacted to me in a perfectly normal way, seemed like a really nice guy and was just going about his business. Maybe I was going to get away with it!

It didn't take long for him to unload the garden furniture from the truck. I watched from the kitchen as he started the job of assembling the pieces. He was a seriously fit looking guy and it wasn't difficult to just stand there admiring him. I could see that it was quite physical work and it was a gloriously sunny day. I suppose I should have been prepared for the moment when he took his shirt off to stop himself getting too hot. He had muscles to die for and as I gasped and muttered a barely concealed "wow" under my breath, he looked over to me and smiled.

"Hey sorry about stripping off my shirt like like this, I hope you don't mind but its hot work out here"

"Oh no, thats fine, I understand" I replied. " Can I get you something cold to drink?"
"Yeah, that would be great, thanks, what do you have?" I had absolutely no idea what Mistress kept in her fridge. " Err, not sure, I'll take a look". I smiled back at him and went to the fridge and stared blankly at its contents. I couldn't believe the situation I had found myself in. I hoped that no one would ever find out. Mistress wouldn't be back for a while, and if she didn't find out that I had been flirting with the delivery man then Sue would never know. No need to panic. Everything would be fine. Just give him a drink, let him finish the job and then he can be on his way. No harm done.

I guess he must have become impatient whilst I looked through the fridge trying to find something he might like. " Not having much luck?" he said as he breezed through the back door into the kitchen "lets take a look at what you have hidden away in there shall we?" He flashed me that smile yet again and came over to the fridge. He positioned himself right behind me, peering over my shoulder into the fridge. He was very close to me and my pulse was quickening again. I was out of my depth. He deftly slipped his arm around my waist, gently holding me from behind, gently but firmly pulling me towards him.

"I'm sorry" he said, "but I think that these maids uniforms are such a turn on. You don't see many women wearing them nowadays and the silk stockings as well, its all too much for me I'm afraid, I'm as horny as hell and I need a woman!"

Now I was worried. The fantasy moment had been replaced by the fear that I was about to be exposed for what I really was.He was twice my size and could easily beat me to a pulp if he wanted to.

"Please don't" I said as his other hand reached around me, locking me in his grasp. "I'm not that kind of girl, really, I'm not what you want"

" I know exactly what kind of girl you are Penny, and right now you are what I want"

He knew my name. How the hell did he know my name. I hadn't told him. He spun me round so that I was facing him, I was pressed up against his naked torso and could feel his immense strength. On the one hand I was terrified and on the other I was thrilled by his power and the certainty with which he handled me. He looked at me, smiled again and said "I've known your Mistress for years, I used to be her personal trainer before I got into the delivery business.She's told me all about you. I'm here as part of your training programme!"

I tried to pull away but his grip was to strong for me. "Penny, if you want to be a maid then you have to learn how to look after your men as well as your Mistress" he said. And then he scooped me off my feet and simply said " I think its time that we went upstairs"

I was powerless to resist. As he carried me in his arms he kissed me. A deep lingering kiss, his tongue pushed firmly into my mouth. I couldn't help myself, I found myself putting my arms around his neck and kissing him back, kissing him with passion wanting him to take me.

As he carried me to the stairs I suddenly caught sight of my Mistress, she had returned without me noticing. In her hand she held a video camera which she was pointing at us. She had recorded everything.

She smiled at me, smiled at him. She walked over to us. She kissed the delivery man on the cheek. "Be gentle with her" she said. And then she turned to me, she whispered in my ear,...

"Go on Penny, you know you want to..."

Liz and Penny

2009-04-14T03:31:00.000-07:00

This is Liz, looking gorgeous for the camera. She says that I'm not allowed to make love with her any more but if I am good she will let me help her get ready when she goes out in the evenings... And this is me, Penny. Photo taken on self timer when I thought I was alone shortly before Liz came home early and discovered my secret.....This is one of the photos that she is threatening to show to all our family and friends if I fail to do exactly as she says...

No going back...

2009-04-11T05:22:00.000-07:00

Liz always sends me to Mistress Grace for day long training sessions on Fridays. It has meant that I now only work a four day week but Liz has always been our main breadwinner and is more successful in her career than I have been. Since Liz found out that I like to wear her clothes her attitude to me has changed dramatically. In many ways she is still kind and loving towards me but she now insists on making all the decisions in our life and I have been forced to sign all of our assets over to her under threat of being exposed to family and work colleagues as a closet sissy. She has made it clear to me that she will continue to love and support me but that she no longer regards me as her husband or lover. I did protest that she should give me another chance but her response left me in no doubt.

"Don't be silly darling, you know that I think you are sweet and I do like having you as my plaything, but you can only get that little cock hard enough when you are being Penny and you know I prefer men. I have given it alot of thought and whether you like it or not Mistress Grace is going to train you so that you can be useful to me as my Maid. Don't you think its wonderful? You get to make your fantasies real and I get to have complete control of my life and still have a companion. Now run along or you will be late to see Mistress, you know how she likes you to be on time."

How it started...

2009-03-23T07:37:00.000-07:00

Everything in my life has changed so much since my wife Liz took control. Now I exist to serve both her and her friend Mistress Grace to whom I am sent for training.

It all started when Liz found out my little secret (she came home unexpectedly one day and caught me trying on her underwear) she reacted in a surprsingly calm way.
"Of course I've always suspected that there was something different about you" she said, " I married you because I like the way you treat me and you are easy to be around but in truth I have never felt you were manly enough for me... now we know why". She continued "I wish you had told me about this earlier, it really didn't have to be a secret, everyone should have the opportunity to express themselves and to be who they really want to be"
I was left completely speechless (not least because I was still standing in our bedroom in front of her wearing one of her basques with steamed stockings an embarrassed smile and a barely concealed erection).
"And before you try to make any silly excuses about why you are wearing my clothes we can both see that you appear to have a huge erection trying to burst through my panties.. I haven't seen you as hard as that in a long time. "
It seemed pointless to protest, the truth was that our sex life had evaporated into fairly brief encounters and I had found it increasingly difficult to satisfy her. Whilst making love with her I would often fantasize about "forced feninization" scenarios and by doing that I had been able to get hard enough to appear enthusiastic. Now my secret was out but rather than shout she was calm and looked at me with a loving smle.
" You know I can't believe I'm saying it but I think you may even look better in that stuff than I do! You really have geat legs, with a little bit of work I bet you could pass as a woman, hah! whatever shall we do with you!
As she spoke I could feel myself getting even more excited and my arousal was very obvious as my cock bulged through my panties.
She looked at me with a sly smile, "you know it would be such a pity to waste that... " and with that she walked towards me still smiling, she put her hand inside my panties and grabbed my erect cock and as she did so she turned and led me to the bed with her hand firmly wrapped around me. " Come along now, there's a good girl, I'm in charge now"
She pushed me back on to the bed and immediately climbed on top of me. She hitched up her skirt and with my cock in one hand she used her other hand to pull aside her own panties and guided my cock to her glistening wet pussy. She didn't give me any say in the matter, she was totally in control and she knew it. As she put my cock inside her and pushed down hard on me she said " from now on we do everything my way, if you want to be a girl then you have to play by my rules is that clear?"
I was in a frenzy of excitement and would have agreed to anything..
"Yes of course" I said,"I'll do anything you want"
"Good, the first thing is that you are NEVER to reach orgasm without my permission, is that clear?
"Yes" I replied,
"Good girl " She continued to ride me and my excitement was increasing with every moment, just by her referring to me as a "girl" sent shudders of excitement through me.
"Now that we have found out your secret things will have to change. You cannot reasonably expect me to regard you as my husband. You can continue as my "partner", in fact it will be fun to have a female friend to confide in, we can still live together but not as husband and wife. Thats non negotiable I'm afraid"
"But.." I protested
She pushed down hard on me and pinned me to the bed by my shoulders . "No 'buts', darling, its simple, you want to play at being a girl and I am happy to help you. We have passed the point of no return. If you refuse to do things my way I will simply tell everyone that you know about your secret. You see what you hadn't realised when you started to play "dress up" with my clothes was that you were giving me a wonderful opportunity to take complete control of both of our lives. Its an opportunity that I fully intend to take. Oh and by the way I probably ought to let you know that I have actually known about your secret for a while, I suspected that something was going on so I discreetly set up a spy webcam in our bedroom a little while ago. Imagine my surprise when I saw the film of you putting on my underwear! Mind you I was even more surprised when I saw how enthusiastic you were about playing with my vibrator! Bad Girl, you really should get your own! Anyway I recorded everything and wouldn't dream of showing your family and friends as long as you do everything I say, understood?!"
"I understand" I replied meekly, although I was secretly thrilled at the way she was taking control I thought I had better show some kind of resistance.. "but this is such an extreme way of dealing with things"
"Well thats' your problem not mine I'm afraid. And by the way I think it would be easier if we changed your name, you need something that will suit your new life. From now on you are to be known as Penny, its such a nice feminine name. "
"Of course you will need training. I'm too busy at work and I think it would be better if you were in the hands of an expert. You may remember an old friend of mine, Grace, well we got a little drunk a few weks ago and she told me that she has an interesting sideline as a dominatrix.
I told her about what I had seen on the webcam and it was her who encouraged me to see this as an opportunity. She has volunteered to take you in hand and you are to report to her house for your feminization training first thing tomorrow. Isn't it exciting!"
It was at this point that I lost control, my excitement had been building as she dominated me so completely and I felt an electrifying surge go through my cock as it spasmed into orgasm.
Her response was immediate, she slapped me across the face with stinging force. "You are never to do that again, my pussy is now reserved for the cum of real men, not girly wannabees like you."
With that she placed her knees on my shoulders, pinning me down and lowered her pussy onto my face. "Lick me until I am clean" she said " its a taste that you will have to get used to...."

Letter from my Mistress

2009-03-10T11:00:00.000-07:00

"Your new name will be Penny, Let me tell you a little about who and what you will be.
Eventually Penny will be employed by one of our wealthy female clients. I can't tell you just exactly who She will be, but suffice it to say that in your eyes she will be the most beautiful woman you have ever known.
You will dedicate every waking moment to ensuring that she is happy, healthy and content. You will have no sexual feeling for her, of course, or for any woman for that matter; this would only compromise your role as a servant. You will admire her, though. In your heart of hearts, you will wish that you could be her. Everything that she touches - her clothes, her undergarments, her makeup, her shoes, and her jewellry. You will be nothing. She will be everything, all that is good and beautiful and worthy of being loved. Your existence would have no meaning if it were not for Her. You will work very very hard, Penny. Your days will be filled with cleaning, washing, ironing,, seven days a week, three hundred and sixty five days a year. What little time you have for yourself will be spent improving your appearance. Your undergarments and uniforms will always be immaculate. Your makeup will always be fresh and perfectly applied.
And sometimes, Penny, when it is late at night and you are not too exhausted from your long day of service, you will pleasure yourself in a manner consistent with the feminine consciousness we have created for you. You will find yourself fantasizing exclusively about men: strong and powerful men who are as strong as you are weak, who are as hard and forceful as you are soft and submissive, men alone or men in groups who see you only as a sexual object, men who want to possess your body in every conceivable way again and again and again.
As time passes you will naturally want to make your fantasies real. Perhaps your mistress will give you a night off now and then. Perhaps she will have given you some of her precious, castaway clothing. Perhaps you will put on a tight dress and high heels and spend an evening looking for male companionship at a local bar. All will be possible once you are a woman.
I know this is very hard for you to imagine, and it might be more than a little frightening as well, but I assure you that we do this for very good reasons. You will simply be much happier if you learn to do as you are told..
Being a maid will be the most important and treasured thing in your life, next to your mistress‘s happiness,
So there it is Penny. I would ask you if you still wanted to go through with it, but we both know that it is too late for second thoughts. You have not been happy as a man, but now I am here to make things better. I look forward to seeing you next week. Please be sure to have your affairs in order, as there is no turning back."

Mistress continues with Penny's training...

2009-03-10T10:31:00.000-07:00

"You are such a good girl" You take me by the hand and lead me to the bed room.You have positioned a chair directly infront of the mirror. "Now" you begin, "here's how its going to work.I want you looking straight into the mirror, I want you watching me fuck you with my strap on dildo. I'm going to train you to love it like the little whore you are.I know that you are a virgin but if you are going to be a good maid you will have to accept this without resistance or question.
I am going to make it easier for you. My hands will be wrapped around your cock.BUT, you only get stroked if you push back against the dildo when it is inside you..When you go down on your dildo cock, you will feel my hands going up your sweet cock.When you come up off that dildo cock, you will feel my hands stroking you down on your cock.You see, my hands, although they will be wrapped around your cock WILL NOT MOVE, you will only feel the pleasure of the stroking if you fuck my hands, as you ride the dildo cock. From now on you will learn that you can only ever cum when you have a cock inside you. You will learn to crave it.
"Now, my sweet little slut.....ride!"
It is hard for me, I really dont want anything to violate me, but the sensation of your hands is too much and I start my rhythm.Shallow dips at first, craving the feel of your hands, I so want to fuck you hands."oohh, i start to cry...please, stroke me,,it feels so good" I say.
"Good girl, thats the way, ride the cock!""Look!, look, sweet little girl, look how good you can ride a cock" pointing my face toward the mirror.
"lets see if we can take it a little deeper" you urge me on.I follow your command and start taking slow deep thrust loving your hands, and being deeply probed by your dildo cock...I begin to enter my orgasm..."oooh"...I cry..
"come on.....come on, litte girl...come for me.Ride it, ride that cock!" "OOOOhhhh!!" i cry.
"thats it, good girl, cum for me, cum for your Mistress!!"
"AAAHHH", I fall back on to the bed orgasming...for you...you taking one hand to finish me off, stroking me firmly, and with the other hand fucking me with the dildo.
I am laying back on the bed, legs spread, like a good little slut... the journey continues.

Day dreams......

2009-03-09T09:13:00.000-07:00

I curled my fingers around his cock and felt it throb as his tongue traced lightly along my jaw to my earlobe. I couldn't believe that I was actually touching his cock, or rather trying to pull it through the leg hole of his shorts. My free hand reached up to the snap and he kissed his way from my ear to my neck with little bites and sucks to burrow under the collar of my uniform to my shoulder. I pulled his trousers down just far enough to expose his member. He stood up straight and took a step around the chair so that his cock was level with my mouth. With my right hand slowly moving up and down his shaft and my left hand squeezing his sack, I pulled my first real cock within inches of my mouth."Oh God Penny," he groaned, " You make me so hot, I'm going to lose it way too fast."I looked up at him, smiled, licked the head of his penis and squeezed his balls. He came immediately his first volley of cum hit my nose before I could open my mouth. I managed to catch the next spurt and felt four or five more throbs and eruptions before he fell back to the couch. I leaned forward with him, keeping his cock inside my mouth and sucked the last few drops of his cum.As I felt his member soften between my lips, listening as his laboured breathing slowed and became more even. I savoured the bittersweet flavour of his semen. . One thing I realized was how much making him cum excited me. I really enjoyed it and I would have been happy to feed on his cock all afternoon

Penny

2009-03-02T06:18:00.000-08:00

Penny the transvestite maid has been away, learning how to be a good girl.

She'll be back soon...