This story involves Cross Dressing and sexually explicit material, if you are under the age to legally read this in your area please go no further. If you are old enough please enjoy. This story is totally fiction, any names or actions are totally coincidental.
This story is copyright andrea_tas@hotmail.com. It may be freely distributed and hosted on free websites or USENET so long as the content is not changed or the author and copyright removed.
The Conference by andrea_tas@hotmail.com
My name is Andrew and I am a married guy in my early thirties. I am fairly slight of build but quite good-looking though not overly masculine in my appearance. I have very little body hair and have a fairly small cock. I have been cross dressing in private for many years though it has eased up considerably since being married as my wife is not at all supportive - in fact she is totally opposed to me dressing. I am bisexual in my tendencies but am normally attracted more to guys when I am dressed as a girl than when I am not. I have never had the chance to explore my sexuality with another guy but have played quite a bit with dildos when dressed.
I had an opportunity come up to attend a 2 day conference (with expenses paid by my firm) in a city several hundred kilometres away from where I live. Even though I would be busy during the days I knew I would have most of the evenings free as well as an extra day and a half after the conference. So I decided I would easily have a few good chances to indulge in my liking for cross dressing. I purchased some additional clothing and make up to update my limited wardrobe . It was particularly limited as it had to be hidden away and I didn't have much chance to use it or add to it so it was a pleasure to be able to add to it with the knowledge I would have the chance to use them.
On the first day of the conference I shaved my legs and underarms. I figured if my wife made a fuss about that it was too bad and as I was not very hairy anyway and we didn't have sex that often figured she might not even notice. I decided to wear some lacy panties, stockings a bra and camisole under my male clothes for the conference.
It felt great having them on underneath and knowing that I would have a chance to explore later. I had gone to the toilet at morning tea time and realised that my fly was undone and was worried about whether anyone might have seen my feminine attire.
For the morning of the conference I was sitting next to a guy called Greg who I seemed to hit it off with really well. I found him quite attractive as well though I had no plans on doing anything about that.
We talked some more over lunch and then sat together through the afternoon session. At afternoon tea he pulled me aside and said that he knew what I had on underneath and pretty much instructed to meet him in the bar of the hotel we were staying at after the final session. I was a little apprehensive about him knowing at first and then thought that it was done and there was no point concerning myself about what might happen.
The bar had some booths which were fairly private and which the table covered the view of anything under the table unless someone bent down to look underneath. I was still a little surprised when after we were sitting with our second drink - and him having said nothing more about his earlier comment - he put his hand underneath and deftly undid my fly.
"Mmmm that certainly feels like a nice sexy pair of panties you have on" Greg said in a quiet voice. "What else have you got on under there?"
My dick had reacted quite favourably to the feel of his hand through the panties which was quite distracting in a lovely way but I managed to say "I have stockings, a bra and a camisole as well."
"Lovely" he said. "Do you have any other clothes along with you? Or make-up?"
"Yes I have a small selection of clothes and make-up."
"Ok. I will see you in an hour and a half in your room. I want you wearing something really nice and sexy, but not too slutty. And make sure you have done your make up as well. What is your room number?"
I told Greg my room number and then finished my drink and went up to my room. I couldn't believe that I just let him tell me what to do, or that he would just do that. I then thought how sexy it was to have someone just take charge in a simple way like that. I was pretty sure that I was going to be expected to have sex with him at some point, probably tonight, and that was an exciting prospect.
I had another shave to get rid of any regrowth on my face, then had a shower and paid extra special attention to make sure my ass was as clean as possible. Then I prepared to dress and put make up on. After I glued my silicone breasts in to place making me a lovely 34C, I selected a little black dress, with stockings, black satin panties and a bra and camisole. I then did my makeup and chose a medium length brunette wig. I had just finished getting ready and I heard a knock on the door. I sprayed some perfume on and nervously went to open the door.
"Wow, you look amazing and so sexy" he said.
I thanked him and then he told me to sit down. He poured me a wine and we talked for a few minutes, with him throwing lots of lovely compliments my way. There was another knock on the door and he told me not to worry it was just dinner. He went and got the dinner stuff in.
After we had dinner he asked me to dance. He was a lovely dancer. Even though I hadn't danced in a female role before it was so easy because he was such a strong leader that I slipped easily into it. We danced for a while and then a very slow song came on. He pulled me much closer and pressed his crotch into me. I could feel him get harder and harder as we danced and as he started to kiss my cheek and then my lips. Then the dancing stopped and he kissed me long and passionately. He broke the kiss to ask me whether I had done this before. When I said no he told me not to worry he would make sure I really enjoyed it.
Again without giving me an option, not that I even thought of objecting, he led me into the bedroom. He kissed me some more and took my shoes and dress off. Greg then told me to undress him. I took his top off and marveled at his well defined chest with a nice sprinkling of hair. Not too hairy but enough hair to be a man's chest unlike mine.
I then took his shoes off. There was a slight pause and Greg said "Go on baby, keep going and just relax."
So I undid his belt and then his fly and eased his jeans off. I then knelt down and lowered his jocks. I hadn't seen many other guy's cocks up this close because of being inexperienced but the sight of this was heaven to me. It was jutting out strong and proud, not so long that I would be concerned about doing anything with it but a very healthy length and girth. I couldn't resist and planted a kiss on the head of his cock and then brought my hands up to feel his cock and balls.
Greg guided me over so that he was sitting on the bed. I knelt down in front and knowing automatically what he wanted I took his cock in my mouth and starting sucking him lightly stroking his cock and balls with my hands. It didn't take too long before I could tell he was about to come. I took just the head of his cock in my mouth and used my hands to finish him off. I was rewarded by a very large serve of his beautiful tasting cum. I think at that point I already knew I was going to be hooked on guys from then on. I let Greg's cock out of my mouth and he pulled me up to him and gave me another long passionate kiss before pulling me onto the bed with him.
Greg then started kissing and touching me all over, making me feel wonderfully sexy and horny. He took my panties off but left everything else on. He made me lay on my front and then worked his way down my back, kissing and touching, then skipped over my ass and worked his way up my legs. This time when he got to my ass he started rubbing and kissing my ass and then spread my ass and started licking my hole. God it felt wonderful having his tongue poking its way into my ass. After a little while I felt something a little cold and moist and realised he was using his fingers to thoroughly lube me up.
He then told me to get up. I did and saw that he was on his back and wanted me to sit on his cock. He said that was normally an easy way for the first time and that it meant I was in control of the penetration. I eased myself onto his cock. It was a little uncomfortable at first but I had used enough dildos over the years that it wasn't too hard to adjust.
When I felt my ass touch him I started moving up and down on him. After a minute or so he lifted me off him and got me on my back before pushing his cock back inside me. He then started fucking me hard and deep. It was absolutely wonderful. After a bit of fucking I realised I was about to come and then suddenly I sprayed my come all over my chest. He fucked me for a little longer and then pulled out, ripping the condom off and then jacking himself off onto my cock and balls.
After I had lain in his strong arms for a while Greg said it was time for him to go. He told me that he wanted me to get rid of all the hair around my cock and balls and to make sure that I was wearing sexy underwear under my clothes again the next day. Getting rid of my pubic hair was not something that my wife would miss seeing but I wanted to please Greg so much I decided to do it. I think I knew that major changes at least would have to happen with my marriage or the marriage would be over anyway.