Hi I'm Adam 21years old. This is going to be a part of a series BUT each story can be stand alone stories. All of the stories I am going to be making are completely true. -Any feedback is welcome. **Toronto, Ont** this is part 1
When i was in my early years I started getting into the idea of being a girl. I would go online and go to straight chat sites and pretend I was a girl and ask guys what they would do to me if they were with me. This would always get me off. Most of the guys talked about how they would dominate me and I like that idea. But being so young I didn't know much. I went onto a gay chat site and began talking to guys that were from the Toronto area (which I live close to). I would talk to all kinds of guys and even opened an msn account too add the guys I thought were good enough to meet so we could continue to talk. I added about 15 guys and had planed to meet a few but all flaked out last minute except one.
The only guy that didn't bail out was about 27-32 years old guy named Steve (not his real name). He was hesitant to meet because of my age but after some teasing for a few weeks he said yes to meeting. I told him I would meet him outside a local diner at 9pm and I gave him a description of what I was wearing so he would know it was me. I had on a sweater and track pants, underneath my track pants I was wearing a red thong (because I'm into that kind of stuff). I was so nervous/scared waiting for him to show up. It being my first time doing anything face to face with someone knowing what was intended for the night. Also not knowing what he was going to do to me. I was waiting there for about 20 minutes then I heard someone come up behind me and call my name. I was so scared at this point. I turned around to see him for the first time and he was about 6 foot 175lbs black hair with stubble for facial hair. I said Hi and he asked me if I knew anywhere we could go. I said I have a few ideas and got up where he lead me to his car.
We drove to a retirement home that was being built just outside of town. During the drive my heart was racing and I was still scared not knowing what he was going to do to me. We didn't talk much on the ride. We finally arrived and it seemed like a good spot dark, secluded and quiet. He parked and asked me what I wanted to do. I was almost too scared to answer but I said "whatever you want your to do". He smiled and we both got out and walked to the rear of the building. I told him this would be my first time so please be gentle. He agreed. We started with some soft kissing while he was running his hands all over my body turning me on. the reached down my pants and felt the thong I was wearing and he asked if I could show him. So I slowly slid my sweat pants completely off revealing my thing. He greatly approves as he pulled me closer for more kissing and groping.
this went on for about 5 minutes until told me to take off my thong. While taking the thong off he laid a blanket down and told me to lay on my back. I did as he asked still scared not knowing what was in store. I told him me had to use a condom, he agreed. He undid his pants revealing his 6 inch uncut cock and about 2 inches wide. He knelt down got between my legs and put a condom on and covered it in lube and started massaging my virgin asshole while I lay back and look at the stars praying it doesn't hurt. I didn't find out until after but while I was looking away he pulled off the condom and re-lubed his bare cock. He started to push with more force against my hole until the tip slowly slid inside me. He paused and said "damn you're really tight". Trying not to scream I just nodded. Steve then slowly worked forward and backward until he was all the way inside me. I felt like I was going to pop.
Trying to Lay completely still hoping the pain would pass (it didn't) Steve fucked me slowly for a bit which felt good but the pain was overbearing. After about 5 minutes Steve started fucking me harder and faster, I could feel his balls slapping against my ass. I could help but moan/scream in pain/pleasure. After about 15 minutes of his continuously pounding away at my ass he said he was going to cum. All I could think was finally it's almost over. Steve said "I'm going to cum inside you!" I just nodded thinking the condom would catch his cum. Steve let a groan of pleasure and his cum shot deep inside me. He slowly pulled out and Sid it was great. At this point pain, shame, relief it was over and empty because he wasn't inside me. Not knowing I was full of cum, I put my thong back on, we cleaned up and went back to his car. I asked him to drop me off where he picked me up. On the way back we talked a bit more just about anything really. When we got back to the diner he dropped me off said thanks then drove off.
I got home and layer down in my bed thinking about what I just did (Steve told me about a year later that he never ever actually used a condom when he fucking me). It was about 3 weeks later when I got the courage to message him to see if he wanted to meet again. He was completely for it. But that's another story. --Go to my profile to see all our stories should be in order.from first to latest meet.
Thanks, there will be more stories about mine and Stevens encounters.
