penny the maid

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...