My first sexual experience with another guy was with a transvestite called Chris. We had chatted online for several weeks before I plucked up the courage to invite him to my flat.I was thirty-nine at the time which was quite late in life to start exploring my bi curious tendencies, but I thought if I didn't try it soon I would always wonder what I had missed out on.Chris was fifty-two and was very experienced and he told me he dressed fully when meeting which was what really attracted me to the idea as I didn't fancy straight looking guys at all but got very aroused by guys dressed as women.
When Chris arrived at my flat on the arranged morning I thought I had made a big mistake as here was this short, scruffily dressed guy who I had invited over to my place for sex and looking at him I didn't feel sexually attracted to him at all. I invited him in and as we had a coffee he told me about his previous experiences and whether he sensed that I was having second thoughts he very kindly said that if I didn't want to go through with this then he would understand. I suggested that if he got dressed maybe I would feel different about it.He agreed to this and said it would take him about half hour to get ready, so I showed him to the bedroom where he could get changed.I went back to the lounge and put on some stockings and panties and waited for Chris to return.
When he returned I couldn't believe the transformation. He had on full make up. a dark shoulder length wig and was wearing a long flower patterned dress, black hose and high heeled shoes.As he walked over to join me on the sofa I felt my cock stiffen inside my red, silky panties. Knowing that underneath his dress he was wearing stockings and panties with his cock ready for me to play with, was definitely a big turn on for me and I was glad that I agreed to go through with this as I was about to experience playing with another guys cock for the first time in my life.
Chris sat down and I glanced down at his stockinged legs which were mostly covered by the long dress he was wearing. Then without a word he pulled the dress allthe way up to his waist, exposing his sexy, stocking tops and black panties which showed a lovely bulge where his cock was concealed inside.He placed hishand on my panties and began to tease my cock through the silky material which got me fully erect in an instant.I followed suit and started to stroke his cock bulge, amazed at how different another guys cock felt to my own. Impatiently I pulled his panties to one side and released his hard cock. His cock was about the same size as mine but felt a lot thicker as I wrapped my fingers around it and started to wank him off.He asked me what I would like most and I answered that I really wanted to see what it was like to suck another guys cock. Obviously he had no objection to this and so I lowered my head between his hairy thighs and firstly started to lick around his foreskin before pulling it all the way back and taking his hot, engorged cockhead into my mouth. Hearing him gasp with pleasure gave me a thrill and I began sucking him off. His cock had a lovely, musky aroma and tasted slightly salty but very nice.He said he couldn't believe this was my first time as I was very good at it and as I continued to slurp noisily on his cock I got my first taste of precome asit began to leak from his cock on to my tongue. It had an odd tangy yet sweet taste to it and I was pleasantly surprised at how good it tasted.
Chris took my cock out from my panties and started to wank me off and unfortunately thewhole excitement of the situation became too much for me. With Chris wanking me as I sucked him off I couldn't hold back and spurted my come all over his hand. This seemed to spur him on and he gasped that he was about to come too and without thinking whether I was ready to accept his come in my mouth I simply closed my eyes and felt his cock twitch and jerk before several spurts of hot, sweet tasting come filled my mouth. I let the come dribble down his cock and into his pubic bush as I didn't have the nerve to swallow it down, thinking I might heave as a result.
So that was my first of many experiences of sex with another guy and very enjoyable it was too.