My first time after waiting for months!

Hey guys! I want to keep a history of all my experiences with other men/cross dressers/transsexuals. My stories will all be true and only the facts will be included and hopefully you'll enjoy them and be able to critique my writing!

I'm a 22 year old guy, living in the UK and recently wanted to discover my bisexual side. However, due to the need of discretion, it had not been going all so well. I joined a free gay hookup site, hoping it would assist me with wanting new experiences, which simply never happened. However, as I found out last Saturday night, all I needed was a night out away from home and I would be able to have the fun I craved! Over the next few weeks, each time I am able to experience something new I will post about it, my first story, obviously, is about being with a man for the first time.

I had been looking to meet up with a man for a few months and decided that a friends birthday away from our local area may be the ideal chance to have fun, online chatting wasn't getting me anywhere and I was bored of waiting. We were heading to Blackpoll for a night out last Saturday, I made my plans in advance and hoped that it would go how I intended. My friends and me were out, having fun, but I didn't drink, as I wanted my first time to be memorable, not a drunken quickie. It was about 1am when I tactically lost my friends in a bar, I headed to the closest gay bar and decided to give this a shot. I had no idea what to expect in a gay bar, I must admit, I was happily surprised. I thought it would be dark and dodgy, but it was a really fun place to go, even if you were straight. Once in, I got chatting to a few people who were very friendly and easy to get along with, but I wasn't interested in meeting guys my own age, I wanted an older guy.

I was dancing away, minding my own business when a man who looked mid 40s approached me and started chatting away. He was very attractive, short greying hair, about 6ft1 and average build, but the best thing was that he was so easy to talk to and relaxed. We both got drinks and took a seat to chat, he informed me that he was secretly bi, but was quite experienced, I was quite happy to disclose to him that I was a virgin with guys, I had no experience with them but it was something I wanted to try.

He asked me how i'd got in the bar discreetly and I told him how i'd snuck away, to which he found amusing, but clever. We chatted briefly in the bar for about 20-25 minutes, before he simply said 'well, I've got my own place if you want to try something with me'. I froze, I couldn't believe that after all the waiting, I finally had a chance to do something that I'd craved for months. To say I was shitting myself would be a bad choice of words, but I was incredibly nervous. I replied 'yeah ... Yeah sounds good', we both stood up and left. Once outside, he told me his apartment was about 15 mins away walking, which at the time I wasn't too happy about, but it turned out to be really helpful as we could talk more and this made me feel so much more comfortable about what I was committing to doing.

We joked about stuff but with the time of the morning (2am) we could openly talk about what we wanted. He told me he was top which made my day, I wanted to be strictly bottom and wanted to know how it felt to be a man's bitch. He said 'don't worry, you'll know by the end of the night what it's like' to which I just laughed, how else do you respond to a guy you fancy stating he's going to smash you all night? I then told him about how I wanted to do it bareback.

Over the few months of deciding I wanted to meet men, I decided condoms weren't something I wanted to use in this scenario, there's no risk of pregnancy and I was happy to take the risks that followed. I wanted to be as intimate as possible and having rubber up my arse simply didn't do it for me.

As we approached his, my heart was racing but I was rock hard at the thought of what was going to happen, I steadied my nerves, told myself that if I didn't do it now, I'd regret it and I would have wasted both our time. We got into his place, which was nicely decorated for an older single guy, he told me where the living room was whilst he was locking the front door and offered me a drink to which i declined, I didn't want anything other than cock, no alcohol would do. His living room was standard single guy, big TV, laminate flooring and one of those L shaped couches. I sat down and he came and sat next to me still chatting about what I may or may bot want to try.

I decided to make the first move, by sitting him back onto his couch, climbing on top of him and kissing him. His hands worked their way round to my arse and I rubbed his dick through his jeans. I was still nervous, but I didn't want him to feel as though I wasn't keen to do this. I unbuttoned his shirt and got myself undressed and climbed back in top of him again. I was straddling him in my boxers, rubbing our dicks against one another whilst his hands caressed my arse and legs. I stood up slowly, bent over in front of him and peeled my boxers off in front him and then spread my arse cheeks. He told how beautiful I looked and I said 'are you going to take what's yours?'. He grabbed me closer and I kissed down his chest and pulled his shorts down to reveal his throbbing cock.

It was about 6 inches in length but quit thick, I had no idea how it was going to stretch me. I got on my knees and licked his balls whilst I began to wank his dick. He moaned with pleasure and told me to play my dick also, which I did gladly. I kissed and licked my way upto the head of his dick and began to tease him by licking it, waiting for him to beg me to put it in my mouth. I took a deep breath and swallowed his cock as deep as I could and he began moaning so loud as I bobbed my head up and down, sucking his cock deep into my warm slobbery mouth.

After a few minutes of this, he lay down on his sofa and I lay on top whilst we did a 69. I continued to tease his hard dick, whilst he briefly sucked mine. I'd never had a guy suck my dick before but he wasn't lying when he said he was experienced. It felt great and then without warning, I felt his tongue piercing my tight little arsehole. Again, a completely new experience to which I helped out to with pleasure as he invaded my arse with his tongue and fingers. I'd prepared myself for this, and wanted him to keep eating my arse. I spun around and began to sit on his face whilst he tongued me deeper and quicker, I was moaning like a little slag and I wanted all he could give me.

I begged him to be inside me and he instructed me as to where he wanted me. I lay on his couch, with my legs spread wide and my arse awaiting his cock, he positioned himself, I wrapped my legs around his waist and he slowly pushed inside me. It hurt initially, but he was thrusting slowly and my arse was welcoming more. I moaned for him to be deeper inside me and he thrust inside me as hard as he could. I screamed in ecstasy awaiting more. I lay on my back, with my legs around him, kissing him whilst he fucked my tight little hole, after a while of this, I told him I wanted to be done doggy style on his floor.

I got up and knelt on all fours, waiting for his meat to he deep in me. I had my face down, my arse up and my boy pussy filled deep with him thrusting hard and moaning loudly. I begged for him to go faster, he told me to 'be a good slut and take his dick like a good slave'. I said 'yes sir' and he grabbed both my hands and placed them behind my back whilst he fucked me ragged and I screamed out like his bitch. I knew I wanted to cum with him inside me, so I sat him on the couch again. I briefly sucked his cock so I could taste my arse on it and I climbed ontop of him and slid his dick deep inside me. I was riding him as if I were a girl and I wanked my dick furiously before whilst we kissed.

Then I got the strongest feeling in my cock and began shooting my load on his chest and stomach, he told me I'd been a good boy and I began licking my cum off of him. My arse was so tight around his dick, I begged for his cum to be inside my arse, I told him how bad I needed it and he began moaning so loudly and thrust as hard up my arse as he could. I was kissing him whilst he came inside me, I could fe his dick shooting rope after rope of thick juicy sperm. I sat straddling him and kissing him for a moment. As he had wood flooring, I got off him and sucked his dick whilst I pushed his cum out on the floor, he told me I was a good little whore and his dick was delicious. As his cum came out of me on his floor, I could see just how much there was! I knelt down and licked it all up and he then picked me up and kissed me again. We walked upstairs to his bedroom and both fell asleep ad it was nearly 4am.

I woke up, about 09:10am and also woke him up, we'd slept in late and his battery on his phone had died, hence why we missed his alarm. He told me that his kids would be their very soon so I got ready to leave. I got dressed and we continued to chat about the night before, wed both had fun and he wanted to do it again so I gave him my number, before I left, I told him there was one more thing I wanted to try before I left. Although I'd had a man fuck me, I'd still never given a man a proper blowjob. He smiled and sat down on his sofa again, I undone his dressing gown and got on my knees again. I whipped his hard cock out and started sucking straight away! He lay back and moaned, calling me a slut and telling me he was going to use me more and more, I swallowed his meat deep in my throat, give him a sloppy suck. I then focused on the tip of his cock and he started to moan louder and fuck my mouth. He then let out a loud yelp and filled my mouth with his cum, again, I could feel his dick shooting spurts of sperm in my mouth and it tasted gorgeous, I craved more and swallowed like a good slag should. I stood up, kissed him and told him we should do it again. The night after in the pub, my friends asked me were I went, I made up a story about meeting a girl, little did they know that I'd been mans bitch and loved it!!!

I hope you enjoyed reading this as much as I enjoyed living it, when I have more fun, I'll update once again! Any feedback is welcome guys, thank you!!! :)