My First Real Man

My first two submissions to Literotica were my first attempts at fiction of any kind, not just the erotic. This third submission is not a work of fiction, but the true story of how I lost my virginity to a lovely kind and considerate older man. I promise this prose is 100% genuine.

I first met Roy online some months ago; I had a profile on a well known Transvestite Website. I was a little put off at first as I had stated in my profile no admirers, " Girls Only" but there was something special about this man, he was sweet and so patient with me. Roy described himself as mid-sixties fit, tanned, and a lover of "Girls". Could see from his profile he looked nice and he sent me some pictures of himself with other girls. We chatted and got to know each other a little better.

Sometime later we agreed to meet; Roy said his wife was working so he would have the house to himself. So our date was set for the following Friday morning, Roy gave me his mobile number with directions to his house, the idea was I would drive to his village and then phone him to get directions to his once.

I spent all Thursday afternoon preparing for my first "date" I shaved myself all over, and selected what I was going to wear. The next morning I was so exited and nervous at the same time, I had to see my wife off to work then prepare myself.

I started off by showering and pampering myself, then I dressed in matching bra, kickers and suspender belt with black stockings. Over which I dressed in a sweatshirt and jogging bottoms. I then packed a bag with my girl cloths, wig and jewellery, and set off on the journey to Roy's village. All the way there I was so exited, with butterflies in my stomach. I reached Roy's village and phoned him, but got no reply, I phoned about 20 times with no luck. I was so upset I could have cried, I wondered what had gone wrong.

Dejected I made my way back home. When I got back in the house I dressed in all the clothes from my bag and spent the morning watching porn and playing with my panty clad hard cock thinking of what might have been.

When I did eventually get in touch with Roy, he was so sorry, it turned out he had given me the wrong phone number! We both apologised and promised to meet again, I was just a case of trying to get time together, with one thing and another it took longer than either of us thought.

Some time later we managed to arrange a day where we were both able to meet, so we decided to try again. I went through the same routine of shaving all over the day before, the next morning showering and dressing in my sexy lingerie over which I had on a track suit. I packed my bag again and set off.

I phoned Roy as soon as I arrived in his village, he answered and we were both so pleased it was finally going to happen. I pulled up outside his door and walked up the garden path trembling. Roy opened the front door and let me in. We exchanged pleasantries, and then he showed me upstairs to where I could change. I quickly removed my tracksuit and dressed in a short skirt and white see-through blouse, I put on my high-heels and my long blonde wig, and I made my way downstairs and walked into the living room, all Roy said was "wow". We sat together on the couch and started to kiss and cuddle. I felt Roy's tongue exploring my mouth and his hand was on my knee.

Roy then asked if he could take some photo's of me, I said why not, Roy had me pose sat on the couch sowing a bit of stocking top, he said "Lovely"

We then went back to kissing and cuddling, Roy then asked if I wanted to go upstairs I agreed so off to the bedroom we went. I sat on the end of the bed with Roy stood in front of me and I undid his trousers and released his cock, I kissed the end of it lovingly then proceeded to suck the whole thing into my throat, I was in heaven.

I sucked this mans cock for some time, the only other cocks I had sucked previous to that moment had always belonged to nylon clad girlies, this was my very first man.

Roy then stood back and got undressed, he then joined me on the bed where we laid and kissed and cuddled. Roy began to undress me, I lay on the bed and Roy knelt above my head, I sucked his cock deep into my throat while he played with my nipples. I continued sucking this powerful mans big cock for what seemed an eternity I was so turned on and felt so sexy.

Next Roy lay down beside me and we kissed and he held me in his arms. He then moved down my body and pulled my sexy black knickers to one side and slipped my girly cock into his warm mouth. This man certainly knew how to suck a girl's cock I was in heaven.

Roy then asked if I was ready to give myself to him I nodded in the affirmative and positioned myself on the end of the bed on all fours. I felt his hands sliding my knickers down and caressing my bottom cheeks. He then knelt on the floor and proceeded to tongue my pussy, I felt his tongue move in and out of my pussy, this was a delightful feeling, then his tongue was replaced by his fingers, first one then two.

I was enjoying myself so much I played with my nipples the whole time.

Then it happened Roy withdrew his fingers and slipped his cock into me, at first he was very gentle, but once I was comfortable he really let rip and truly reamed me.

I was so turned on I looked down between my own legs and could see come dripping out of the end of my cock, which was not even fully hard, I scooped the come of the end of my cock and licked it of my fingers. Roy continued to fuck me, and then I felt him stiffen up and come inside me. He came in 5 or 6 spurts and I felt them all deep inside me. Roy withdrew from me and took his condom off. I collapsed onto the bed totally used, but very happy that I had at long last lost my virginity.

Roy lay on the bed next to me and I put my head on his chest, we chatted for a while and while we talked I started to play with his cock which soon started to grow, so I leaned over and started to suck his cock, I alternated between sucking him then wanking him, I was in T-Girl heaven. Once I had gotten him hard again I lay on my back and open my legs, this divine man placed my ankles on his shoulders and slipped his cock into me. I loved being fucked again, he started to ride me hard and I started to wank my cock, we carried on like this until I felt him stiffen and start to come, this pushed me over the edge and I came at the same time, my girly cock sprayed come all over my chest and I felt my orgasm from deep inside me.

I lay back totally exhausted but happy in the knowledge I was no longer a T-Girl virgin, and had just been fucked twice by a very sexy man who had used me as his slut and I had loved every minute of it.

I have spoken to Roy since that day but we have not managed to repeat it yet, we will tho and when we do I will add chapter two.