Written by Pat262
16 Feb 2012
My first experience as a cross dresser
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Firstly, sorry if this story is a little long but it is 100% true and it completely changed my life.
I am married to Samantha who, when this happened, ten years ago, was 40 and I was 35.
Samantha has always liked me to fuck her dressed in stockings and suspenders and has always insisted I keep my hairy bits smooth, apart form my legs and arms. I always found it very erotic wearing stockings, but never really thought about how other men would find it.
One weekend we were invited to our friend Pete's birthday party which was taking place at his house, it was his 40th so quite a big one, and we were surprised to be told there was a theme, 'Vicars and Tarts'. My immediate thought was where am I going to get a Vicars outfit, but Samantha had other ideas!! She suggested she go as the Vicar and I go as the tart! At first I refused but the more I thought about it the more I thought what a great laugh, and for some reason it was making me feel very horny.
Samantha offered to help me get sorted and also insisted I do it properly, that meant shaving all over, including my legs, arms and armpits. She also went out and purchased a blonde wig and a full tarty outfit consisting of black lace underwear, sheer seamed black lace top stockings, 4 inch sling back black patent heels, very short white flared pleated skirt, and a black lace long sleeved blouse. She also said she would do my make up and we had a week to master walking in heels.
Her enthusiasm surprised me but she really wanted to have a great laugh and surprise all my friends with how feminine I could look. I am quite lucky in that I have a small frame and am very slim through doing lots of exercise, so Samantha thought I would make a great 'tart'.
On the day of the party we got ready, Samantha looking like an old vicar you would find in a country village somewhere and me looking like a real slut, including full make up and false eyelashes, and surprisingly horny. In fact I thought I looked pretty good and was surprised with my look. I was nervous about seeing all my friends and what they would say, but having played a variety of sports with them for a number of years, and been in a few scrapes, I also knew they would find the funny side.
When we entered the house the first reaction was astonishment, the second was laughter, and the third was complimentary. Most of the women commented on how good I looked and were surprised how well I could walk in heels. Others were really envious of my legs and kept saying how good they were! Obviously I got called various unsavory names by my mates, but after a while they almost forgot and the talk turned to the usual stuff, football, cars and women.
A few of us were talking in the kitchen and I was sitting at the end of the table, legs crossed and plenty of stocking and thigh showing, not deliberately but the skirt was so short I had no choice. Whilst chatting i noticed Pete's Dad, Mick, kept looking over at me. Mick is a big man, about 6'4'', 57 years old, at the time, and heavily built. He is also a real 'mans man', builder with big rough hands and loud. I kept looking over and catching him looking at my legs and basically eyeing me up. I felt a nervous feeling in my stomach but also a twitch in my lace panties, I had never felt like this before.
Next time I looked over at Mick I smiled and he smiled back raising his glass. Five minutes later he was sitting next to me and joining in the conversation with me and my mates. I turned to sit facing the table, legs tucked under but still crossed, As we talked I noticed Micks knee resting against mine, and again I felt slightly aroused. He soon had placed his hand on his knee and rested it against my stockings, with me thinking it was an accident but I was now feeling nervous, excited and also very sexy, could this big rough man actually fancy me?
Next minute I felt the hand move on to my knee and start to stroke my stocking clad legs. Mick carried on chatting to everyone as if nothing was happening, and to my surprise I did not remove his hand, just sat transfixed getting my right knee and thigh fondled. The feeling of arousal was immense and my cock was like rock. He stroked up my thighs until he reached my stocking top and started to try and push his hand between my crossed thighs. What could I do but part my legs slightly and let him stroke the inside of my thigh. He looked at me, laughed slightly. said 'I'll see you later' got up and left the table.
I felt really flustered and took off to the toilet to calm down, trying to hold my cock down on the way. It was one of the most erotic things that ever happened to me and I felt really horny but confused at the same time.
I made my way back to the kitchen and stood with my back to the kitchen unit talking to some of my wives friends when Mick appeared and stood next to me. My heart jumped and I tried to look cool, but I felt excited at what might happen next, and was not disappointed. As we chatted I felt a hand slide up the back of my leg and start to fondle my bottom. I just let it happen, carried on chatting and enjoyed it. Mick slipped his hand inside my panties and started to rub my bum hole. He whispered to me 'upstairs in five minutes' and walked away.
I cannot explain the thoughts running through my head but I found myself walking up the stairs five minutes later into the unknown. As I reached the top i could not see Mick but as I looked up he was standing st the top of the second staircase of the three story townhouse. He beckoned me forward and I took the second flight of stairs. Mick walked ahead of me and I followed him. He walked into what turned out to be Pete and his wife Sarah's bedroom. He held the door open and I walked in. He then passed me and walked into the en-suite bathroom. I followed and he locked the door behind us.
I stood with my back to the sink and Mick approached me. He put his arms round me and immediately tried to kiss me, and I responded. His tongue was exploring my mouth while his hands were all over my bottom and rubbing my stocking tops. He started licking and kissing my neck and talking dirty to me, telling me I looked like a real slut who wanted to be used by a proper man, and that I had been cock teasing him all evening. He then told me to feel his cock and I started to rub him through his jeans, it felt big. He stood back, unzipped himself and dropped his jeans to the floor. He told me to kneel and take down his boxers. I pulled them down his legs and a big shiny helmet appeared and a much bigger cock than my own. 'Fucking suck it then you slut'. I did what I was told and took it in my mouth. It felt great and I think I was a natural, I held it and licked it from end to end, wanked it and licked his big saggy balls. Just then there was a knock at the door, it was Pete wanting to go to the toilet.
Mick shouted 'Fuck off I'm having a shit' and kept pushing his cock down my throat.
He got me to stand up and lean over the sink with my short white skirt riding up over my smooth arse and legs. Mick started to rub his cock over my panties clad bottom and then pulled them to one side and started to rub his cock against my smooth arse. I was starting to get worried when he pulled back and said 'Your not getting fucked this time, that's for the next time baby, this time your going to swallow my spunk'.
He got me to sit on the toilet and pushed his big cock down my throat making my gag, which I loved. He then held the back of my head and started to ride my mouth hard calling me all sorts of dirty names. I started to cup and rub his balls and then felt him start to tense. Next thing he exploded filling my mouth with spunk. He held on to my head as he grunted and I swallowed what I could, although some did escape and dribble down my chin. He then told me to lick it clean which I did hungrily.
Mick stood back, pulled his things on and threw me his business card.
'Ring me tomorrow you tart and we will arrange the next time'.
I just nodded and sat there as Mick left the room. I got up, locked the door, got my cock out, pulled it twice and spunked like I never had before.
Needless to say I called mick the next day and we arranged to meet at his house when his wife was out. He fucked me the second time and I became his 'bit on the side' which I am to this day. I eventually told my wife I liked dressing and wanted to stay smooth which she agreed to, but she still does not know about Mick.
We have been away for weekends where he has used me throughout our time away and I have been dressed as a women from the time we arrived to the time we left. He only ever lets me wear very short skirts which don't leave a lot to the imagination. We have also had a couple of threesomes with other blokes who Mick works with.
I will keep on letting Mick fuck me for as long as he wants, but he is getting on now and
I need to start looking for someone younger, any offers?