Crossdressing Holiday

Julie Jessica

   

I have been cross-dressing all my life as far back as I can remember. I am heterosexual and married, in my mid forties. My story starts when I met my wife. About two months before we were due to get married she came to me to call the wedding off she would not tell me why at first but after a big deal of auguring and upset she confessed to me that she had in the pass before I had met her had had lesbian flings. No long term girl friends but servile one night flings, for the past two years she had suppressed her feelings for other women but did not think it would be right to get married.

I did not want to lose the woman I had fallen for and really loved and rather than give up on her (Maggie) we decided to get married and I agreed to turn a blind eye to any flings Maggie would have as long as they would stay short term relationships. With Maggie being so honest with me I confessed my cross dressing urges. She was not really both by my confession and only asked how often and what I wore. I told it was mostly my sisters clothing and only in the privacy of my bedroom….it was a sexual thing for me.

We married and moved in to our own house sex life was great, lots of privacy I resisted the temptation to dress up and as far as I knew Maggie was not have lesbian sex. A couple of years in to the marriage our first child was born this was followed a year later by our second child. After this sex was off the agenda. me and Maggie realised some was not right so we decided rather than fall apart it would be a good ideal for Maggie to go to one of the known gay pubs and pick her self up a woman for a one night stand and in return she would let me wear her under wear well she stayed out in a local hotel. I did not want to meet or know the person she was going be with .this seemed to put the spark back in to our sex life at home and over time Maggie bought me many items of clothing so as I did not ruin hers as I am 15 stone and six foot tall. we even bought some size 11 high heels on a weekend trip to London ( the internet was not around then ). But as the kids got older my dressing had to put on the back burner as I did not want them to find out, Maggie continued her so called one night stands every couple of month. time pasted and my children have now left home which brings us to this present day. For the last six month Maggie has been proactive in getting to diet let my hair grow and generally let me cross dress with make up, teach to walk more feminine to the extend I feel quit comfortable. Maggie assured me over and over that in the right light I would pass for a lady, I never really believed this as I feel and known I am a man in a dress.

For this years holiday Maggie sugest than we hire a private villa in Portugal, I left all the arrangements to her and in June this year we when. As with most men I left all the packing to Maggie .we arrived ain Portugal for Maggie to tell this was her treat and for the next seven days I was going to live 24 /7 as the woman I alls wanted to dress as I could not believe ant I was hearing, Maggie had always let me cross dress at home but she knew I was heterosexual and only craved the occasional session I did not want to live as a woman . When I went to unpack my case I found it full of nothing but ladies clothing. The villa was secluded so I played a long with Maggie. Straight away I was in a pink shimmer string bikini. My nails painted to match. (I do not have any body hair as I normally remove it at home and wearing a pair of three inch heels. I venture in to the outside and had a mixture of feelings, fear being one but a feeling of release as I never ventured out side before. Maggie laughed at me and with me because there I was in a foreign country six foot tall my weight was now fourteen stone standing and acting out one of my fantasies. We had the best sex ever there and then.

Evening came and Maggie told me to go get dressed in the clothing she had laid out in the bedroom, this consisted of black pleated mini dress covering my neck and arms and my four inch black stilettos. And underneath I was to wear my leather waist clincher which is done up with draw strings( I have learnt to do this my self over the years) I can reduce my waist by about six inches. Black lacy and satin bra with full matching knickers. In the mean time Maggie said she would prepare supper. Mags came in to the bedroom applied some make up to me and did my hair. Electric pink lipstick, pink eye shadow and masscare.Clip on chandler ear rings I do not have my ear pieced. I felt great and elated. I walked in to the kitchen expecting to see food on the table but there was nothing. Maggie came out of the bedroom looking as great as ever and told me to get a move on the taxi was waiting, I froze because before today I had never been outside dressed as a woman and now I was going for a meal. I had no time to think as the afternoon had gone so well I just followed Mags out the door and in to the taxi. It was dark by now , I never spoke in the taxi for fear of giving myself away I just sat there my heart pounding but Maggie kept reassuring me. After a short ride of no more than five minutes we arrived at the bar/restaurant and Mags and I entered. Maggie explained she had researched the place we where staying at and this bar was gay friendly which I later found out to be a lie she told me just to put me at ease. We sat at the back of the bar in a dimly lit corner, a waitress bought us a bottle of wine and after a glass or two I felt a lot more relaxed, especially thinking it was a gay friendly bar, and the gay community seem to be more excepting of cross dressers. Twenty minutes pass and I needed to have a pee of I stumbled to the loo trying to walk like the lady I was trying to pass for I reached the toilets and for the first time ever entered the ladies, had a pee and came back out of the toilets only to see Maggie talking to a stunning attractive woman at our table. I could not bring my self to approach the pair of them and watched what seemed to be ages.. they did appear to know each other so I thought to my self it might be some one we both knew so stayed out of the way as it would have been impossible to explain what I was wearing to who ever it was. To my horror Maggie got up out of her seat and left the bar with this other woman, I went to chase after her forgetting in my panic where and how I was dressed I moved quickly and them the waitress stopped me ,Maggie had left without paying our tab. This stopped me in my tracks I did not any fuss dressed as I was so I open my handbag and gave the waitress my credit card. I felt such a idiot totally humiliated as I stood there in a black pleated mini dress, four inch black high heels , ear rings full make up painted false nails struggling to walk and move because of the corset it was clear to all once I left the safety of the dark corner I was a man in drag to top this my credit card had my name on it Mr Justin ……….

I left the bar and started the short walk home not thinking clearly I knew I could not pay for a taxi with credit card. I finally arrived home trying all the way to walk and portray the woman I was dressed as .I did this so as not to bring attention to my self but with hind sight it would have been better to take the shoes off and get back to the villa as soon as possible the walk took me approximately 20 minutes all the way home I kept thinking how could Maggie have done this to me. I got back to the villa and I could see the lights on thought the shutters. I opened the door only to see Maggie in the bedroom with the woman from the bar. They were having sex they turned to me and both just burst out laughing. The woman turned out to be her lesbian lover from England, they had been having an affair since before we where married. They had planned the whole thing. I sat there I did not know whether to cry or laugh with them. They BETWEEN THEM HAD MADE ONE OF MY TEENAGE FANTISES come true. The rest of the week continued in the same manor. I became one the girls during the day we would sit around our pool all in bikinis, I ended up with great tan lines and in the evening I would cook the girls a meal. They even gave me a girl's name Justin became Julie. I was not allowed to sleep with Maggie and her lesbian lover of 22 years but they did permit me to watch. Maggie and her friend carol would tie me to a chair and position me so I could see every thing after wards they un tie me and watch me masturbate my self. Thee week soon pasted now the three off us get to gather often Maggie has never been so happy she always wanted share her secret life with me. I now dress at home more often carol comes over for suppers which I prepare Maggie and coral sleep together once ,twice a month me and Maggie now have the best sex ever . can wait for summer 2008

  

  

  

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