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By *atiek OP TV/TS
2 weeks ago
Cranleigh |
I've loved reading the stories in the forum about how many of us first got into crossdressing which set me wondering about first time sex en femme. Here is my story as best as I can remember it.
Like many of us I'd dabbled with dressing as a teenager, masturbating while wearing my mum's underwear etc and was turned on by thoughts of being used sexually like a girl. However, I didn't know anyone I could share these feelings with so my dressing had remained as an occasional wanking treat when I was home alone.
Things changed for me in the summer of 1970 at the age of 19. By then I knew I was bi and I had already had some meets with other boys and men although my experience of man on man sex was still limited and very much my secret. One night I had met an older man in a public toilet who took my anal virginity (see my story in the Toilet Tales thread) and I had arranged to meet with him again a few days later expecting to have another cottage session. However, when John picked me up in his car early that evening he told me he would be taking me to his home as his wife would be out until late which would give us plenty of time to play. I'd already let him fuck me so I was not exactly frightened but I was nervous about what an older man like himself might be expecting me to do for him!
John lived in a large detached house on a quiet, respectable suburban road not so far from where I then lived with my parents. When we arrived he took me straight upstairs to a guest bedroom with a double bed, a free standing full length dressing mirror and it's own en-suite bathroom. Without saying anything he started to take off his clothes so i did the same anticipating that he would want to fuck me again. This was the first time I'd seen him fully naked - he was in his late 40's / early 50's, with a handsome face and a well groomed look but quite stocky and verging on overweight with a lot of body hair except for his cock and balls which were shaved and free of pubic hair. By contrast I was very slender with long shoulder length dark hair, as was in fashion at the time, and little body hair except for the fluffy pubic hair around my genitals and hair under my arms.
When we were both undressed John took me into his arms and began to kiss me and while his hands caressed my naked body I opened my mouth to his tongue and gave myself to him. As we were kissing I noticed some female underwear lying on the bed and assumed it had been left there by his wife. He saw me looking at them and told me we would get to that in due course and then asked me if my "pussy" was clean. I knew he meant my arsehole and somewhat ashamed I had to admit it was probably not and that I was not even sure how best to do it.
He must have anticipated this would be the case and led me into the bathroom, which had an old fashioned telephone style hair shower in the bath and showed me how to use the shower hose to douche my arsehole. Once clean he told me he was going to shave my cock, balls and armpits as he needed me to look smooth all over for him. I was a bit nervous, wondering how I could explain it if my parents or any of my straight friends spotted this, but knew I would let him do whatever he wanted to me. In no time at all, using an old fashioned safety razor my cock, balls, bottom and pits were hairless and my new lover declared I was now ready for the next stage in my education.
I had been expecting that once my arsehole was clean he would be bending me over to receive my second ever fuck and I was desperate for him to do just that! It seemed that he had other needs. Taking my hand he led me back to the bedroom and told me to start dressing in the female garments on the bed. I started with a white lacy garter belt and pulled on the pair of seamed nylons which he helped me to attach to the suspenders. He handed me a flimsy white lacy bra which, having no tits at all, I did not fill out but which seemed to fit well over my chest. Once he'd helped me to buckle it up I put on a tiny pair of panties, again in white with lace trim. By now the feel of the fabrics against my skin and the excitement of what was happening had made my cock so stiff that it would not go into the little panties which my now hairless balls had already filled. Finally as a finishing touch he slipped a necklace round my neck, clipped some big gold earrings on my ears and then applied bright red lipstick to my lips.
Once I was dressed in the lingerie John turned me around to face the mirror. I simply could not believe the transformation and how feminine I looked with my slender figure and long hair adding to the illusion of a young teenage girl! He said he wanted to see how feminine I could act and told me to pose for him. I flounced around the room thinking of all the bimbos I'd seen in films, displaying myself shamelessly to him. I'm sure I was being OTT camp but from the smile on his face I knew I had got something right!
Standing back displaying his masculine body with his hard cock and big balls John asked me how I felt now I was dressed. I confess I gushed, telling him how aroused I felt and that all I wanted to do was to be able to show him how grateful I could be for giving me this experience! He said that when we first met me he had could see that I might be girlfriend material which was why he had wanted to invite me to his home and dress me. Although I was thrilled with what I'd seen in the mirror, I was still very nervous about disappointing him so I asked him if he liked how I had turned out. When John told me I looked how he had imagined I could be and that he would show me how a real man could use a girl like me I blushed with pleasure.
For the next couple of hours I let John use me in any way he wanted. I worshiped his cock and balls with my lips, tongue, mouth and throat, I rimmed his arsehole kissing and tonguing his hole and then penetrated him with a dildo while he instructed me in how to please him with it and he fucked me in positions I had not even thought about.
At one point while we took break for a drink I asked him if the lingerie belonged to his wife. He said he had put together a collection of her cast offs together with some other items for friends of his who enjoyed dressing to use but that what I was wearing were all hers as my body shape was similar. It occurred to me then that what he needed from me was to be a sex partner who would accept without question those all those things his wife would not allow while in his imagination he was having her! This did not upset me at all as I was just so grateful that he seemed to find me attractive and if pretending that I was his wife excited him I was more than happy to play that role.
Throughout the evening John had shown remarkable stamina, his cock, which although not huge was a very respectable 6 inches, stayed hard most of the time and he had not yet cum even though on a few occasions I knew he must have been close and I'd licked up the pre-cum leaking from him more than once. As a finale to the evening he stood up and pushed me down on to my knees thrusting his cock into my mouth. As I used my lips and tongue to massage his big bell end I felt his cock begin to spasm and he pumped spurt after spurt of hot sperm into my mouth filling it to the point that cum began to leak from my lips. Pulling his cum covered cock out he told me to look up at him, open my mouth and show him what was there and then swallow it before licking him clean. I did as I was told which was yet another first for me. I had let men cum in my mouth before but never swallowed sperm.
Sadly the evening came to an end and I became almost tearful when I had to take off the lovely feminine lingerie and go beck to being just a young man. Before I left John looked at me very seriously and asked if I would agree to be his girlfriend. Of course I said yes and he told me he would call me Katie, the sissy name I've used ever since. He also insisted that in the bedroom I must always obey him without hesitation and told me would also introduce me to other men who like himself secretly enjoyed cock. For the next 5 years or so until I moved away from the area for work reasons, Katie met John for sex often and also regularly serviced a group his friends, all older local men, but that is another story.
Of course all this happened a long time ago and memory can become hazy! While the basic facts of what happened to me are real, meeting John, being taken to his house, him dressing me and having sex en femme for the first time, but in the interests of telling a good story I have filled in some of the detail from my imagination for which I hope I can be forgiven. I hope you enjoy reading this and I would love to hear other crossdressing sissy's stories of the first time they had dressed sex. |
