I started chatting to John on Gaydar for about a week when he asked me if I would like to meet up with him. I am 33, but I am young looking and petite for a guy, being only 5'3". I had not seen a picture of John, nor he of me, but he informed me he was 56 years old, married, and a rather tall 6'3"! I said that was cool, where, when and all that. He said he was coming to my city (Basingstoke, UK) on business and had a hotel room for a couple of days, one of those faceless money making chains, and when he got there he would text me the room number and I could come up, have a chat, maybe a drink, maybe something else if everything went OK!
The day of reckoning came, and that morning I got a text from John telling me the hotel and the room number, and to meet him later that evening. Obviously I had butterflies in my tummy; this was a guy I had never met, never even seen or spoke to, yes I was so excited, so nervous. Maybe nothing would even happen, maybe he wouldn't even be there... so many thoughts went through my head, some good, some bad, some horny!
During out chats I had told John that I was not a virgin but I had been with just a couple of guys before him, and that I was straight acting, and that I liked to wear womens underwear, which he said he liked and wanted me to do. He asked me for total discreetness, him being married, and I told him that was fine with me I wasn't looking for a relationship anyhow. I also told him I was only passive; I have no desire to put my little cock into some mans arse, I only have the desire to have a cock in my own arse. There; we had the groundwork, anything else we could talk about when we meet.
I had a serious shower, dried myself and put on my new pair of undies; a lovely small black lacey thong, with flowers on the front, and diamontes at the back on a small chain. It turned me on just to put it on. I had a small rucksack that I packed a pair of fishnet stockings, a suspender and a pair of black size 5 stilletoes. Then I dressed myself in normal guy clothes; jeans, a shirt, trainers, jacket. There is no way anyone could tell I had on this tiny sexy thong on. But I knew.
After a short train journey I got to the centre of town. I was so nervous, nervous like you wouldn't believe! I walked to the hotel, but every step I was getting more and more apprehensive; could I go throught with it? I had to, I had come this far. When I got to the hotel I just walked in, and straight past the reception like I knew where I was going! In reality my head and stomach were doing cartwheels! I was hoping the receptionist wouldn't stop me, and he didn't, and I was hoping he couldn't read my mind either.
I got in the elevator and went up; I remember it clearly. Room 334. My heart was pounding. Everything was pounding. There it was; the door in front of me now. I lifted my hand to knock, and hesitated; then knocked three times. By now I thought I would die! What if I had the wrong room? What if the guy didn't like me? What if what if what if! The door opened.
A well dressed man stood before me. He held out his hand "Hello James. I'm John. Would you like to come in?". Of course I bloody would. "Yes" I replied and shook his hand. He was pretty much as he'd described himself; he was tall, he was well built but not fat, and he had thinning grey hair, not bad for his age. He had a decent room, as decent as they can be. There was a living area with a couch, table and TV, and a separate bathroom and bedroom. On the table was a beer John had been drinking. "Would you like something?" he asked. Only your cock in me. "Do you have any wine?" I replied. He went to the fridge as if he had read my mind and pulled out a cold bottle of white and proceeded to pour two glasses, all the time he was looking at me. I could tell, yes he liked me. He wanted me.
We sat on the couch, and made some small talk. He was looking intensely into my eyes; I didn't know where to look! This went on for about 15 minutes, by then we had finished the bottle of wine, and he took out another and returned to the couch. As he sat down his hand rested on my leg, quite deliberately. I didn't move. As he poured more wine, he talked more. Then he lent over me as to get something imaginary on my right, and as he did do his lips met mine, and his tongue went into my mouth. I reciprocated this intense, slow, kiss, and his hand moved up and started to unbutton my shirt, and he opened it, and started to slowly rub my nipples. I was going crazy in my head, my little cock was so hard! Slowly he took off my shirt. I could see that he had a hard on and I knew he wanted to use it on me.
"John" I said "I have things to put on, we talked about them you remember?" He remembered, his eyes went wider! I went into the bathroom. I looked at my rather pissed self in the mirror; and took off my guy clothes. I still had the thong on; I think I'll leave that for John to take off. I put on my suspender belt, and rolled my stockings up my legs and attached them. I put on the shoes, and as soon as I did I knew I'd have difficulty walking out. I'm not a tranny, these are for bedroom use only, and don't get used nearly enough. Anyhow, when I was ready after about five minutes, I stumbled out in my heels. John was standing there, naked, and his cock was pointed straight at me! He looked at me as if for my approval. I smiled, and he smiled back, and sat down on the couch.
I tried to sexily walk to him, I put a knee on the couch, and took a large sip of wine, then another one quickly after. He didn't move, and I bent down and started to lick his nipples, each in turn, and his hand went to my nipple and he started to play, and then he was rubbing my back, my chest, my arse, "I fucking love those stockings, the heels everything!" he said. I kissed him, then slowly kissed down his hairy chest to his cock. I flicked my tongue along the top of it, he made some noises, I did it some more, then I took him in my mouth; he groaned, and put his hands on my head, didn't push down though, just resting, but demanding! His cock was not too big, good thing as I have a small mouth, maybe only 6 or 7 inches at most. I sucked like a pro, well he enjoyed it anyhow, he was pushing up as I was sucking down. His hands started to move over to my arse and stay there, I felt him pull the thong aside, and he slid one finger into me. I sucked him harder, smelling that lovely ball smell, his musty scent! "I want to fuck you. I want to fuck you now" was about as romantic as he could get,
As I sat back on the couch he knelt down in front of me, and pulled off my little panties as fast as he could! He threw them and came up to kiss me again, playing with my nipples again as he did do. I could feel his cock pressing against me; as he kissed me I started to play with his cock. He was ready for me. "Do you want me to go to the bedroom now?" I asked. "No I want to fuck you here now James." "Do you have something?" "I have baby oil." He rubbed some from a handily placed bottle onto his cock, and massaged some into me arse. "You know what I mean, do you have something to use?" I said. "I'm going to fuck you bareback James, you're my little whore tonight." I was shocked at the tone, it wasn't aggressive just assertive again. Oh well, I thought, he wants, he'll have. His cock was pushing against my tight shaved little hole, he was kissing me as he was kneeling down in front of me. Then slowly he pushed his cock-head in, and stopped, looking at me, he eyes asking if I was OK. The pain was there, but I tried not to show it, dulled a little by wine. I smiled back trying not to wince, and pulled at his hips gently, He smiled back, kissed me, and pushed into me. I pulled his head into my shoulder and let out a silent gasp as I felt the length of him in me. John started to fuck me, this huge great old guy, 23 years my senior, on a couch in a hotel room in Basingstoke!
He lifted me up, whilst I was still impaled on his cock, his hands clutching at my ass cheeks, kissing me as he did so, and took me into the bedroom. He lay me on the bed and continued his rhythmic fucking. He lifted my legs up so that they were over his shoulders; wow! I felt his cock go really deep into me, pain and pleasure mixed. As I lay there he licked my nipples, sucking each one, gently biting down and then flicking with his tongue. I had my arms up above my head, as he was fucking me we were going further and further up the bed, I had to stop us somehow. After a few minutes he let my legs down (thank god they were aching!). He reached around and unbuttoned my suspender belt, and tore at the stockings. The shoes were long gone. So there I was totally naked now, no lady gear, and all this time his cock was still hard in my asshole. He rolled over onto his back, pulling me over on top of him. I felt so tiny up there resting on his cock. His hands went down to my ass and he started fucking me again, this time though it felt reallllly deep, deeper than when my legs were over his shoulders. I groaned as if felt like his cock was going to push my intestines up to my mouth, even his average sized one! Fuck I thought! Then, the first and only time I have ever felt it, and believe me, I've tried, he rubbed on my prostate. Now I know what women feel! Its hard to describe, but its like every cell in your body wants to scream out, and I screamed out, he stopped, I told him "Don't you dare stop, don't you dare fucking stop!" and then I came, god did I come, I basically blacked out for a few seconds.
When I came to he had flipped me over and was on top of me again "You like that do you James, you like my cock in you?" "Yes! Did you come?" I asked. "No. Now put your legs over my shoulders again James." Even though I was aching and not really with it I did as I was told. It didn't take long, he pushed into me a few times and I saw the beads of revealing sweat on his forehead, and he came, came bareback into my tight ass, I felt his magma hot cum squirting up inside my hole, his cock harder than ever, he was pushing into me harder than ever. He stopped, and looked at me with those 'did I do OK' kind of eyes, and I just smiled kissed him softly. He pulled out his now softening but semi hard cock from my body. I felt the cum drip down between my ass cheeks and onto my legs as I got up to use the bathroom.
I didn't stay the night; I don't think John really wanted me to, we had both had our fun. I texted him once after to say thanks, he just replied with an x and I have heard nothing since, and this all happened in October 2008. Thanks John. X.
*** This is a true story. I'd love to know if you enjoyed it, your opinion, and if you'd like to hear any more. jamie26_uk2002@yahoo.com ***