Sex with a man. It’s a fantasy some straight guys have but few act on it. For quite a while I have thought about going through with it. I didn’t really have a fantasy guy picked out, except for one aspect… his cock. My fantasy guy had a big cock. I figured if I was going to go through with the fantasy I would go big or go home. I would talk to guys online and it would get me hot, but as soon as I blew my load that desire to try it out for real slipped away. Heather and I had talked about these fantasies at length; the idea of me hooking up with another guy was as big of a turn-on to her as her being with another woman was for me. Sometimes we would bring ass play into the bedroom and I went as far as buying a strapon for her to wear. Still, nothing happened beyond talking. I had pretty much concluded that it was always going to remain a fantasy, one not to be acted upon.
All that changed last week. Last week I decided to finally fulfill the fantasy. I’m catching up to 30 and if I’m going to experiment I better get moving on it. So, I started as I had so many other times by chatting with guys online. There were a couple of guys that I had talked to on multiple occasions so that’s where I started.
Jake was one guy that I kept getting drawn back to over the years. He was always willing to talk to me about my fantasies and encouraged me to go through with them when I was comfortable. We just seemed to click. Plus the pictures he had on his profile were quite nice. I don’t really have standards of judging a man’s attractiveness, but he was pretty good looking. And his cock? Big. A solid 8 inches long and almost 2 inches across. Like I said, my fantasy was for a guy that was hung and Jake certainly filled the bill. One thing that really reassured me about him was a few of the comments on his profile. All signs pointed to this being the guy that I was going to lose my anal virginity to.
Allright, enough background. That isn’t why you are here. Last night Jake and I made plans to meet up at his place. I was nervous as all hell as the clock ticked down to the time I had to leave. A quick shower to freshen up didn’t decrease that nervousness at all. If anything, it made me more nervous. So I hopped in my car and headed up to his place.
I think I was shaking a little bit as I walked up the stairs to his apartment. He opened the door as I approached and we shook hands. How often do you start off a hookup with a shaking of hands and introductions? It was slightly awkward, but I don’t quite know how it couldn’t be. He offered me a beer and we headed into his living room to get to know each other in person a little. We had some small talk about our interests and such before we moved the conversation in a sexual direction. Like when we were chatting online Jake has a way of making you feel comfortable.
After we finished our drinks it was time to make things happen. I hesitated a moment, so Jake made the first move for me. Jake leaned over towards me a moved in for a kiss. Kissing another man wasn’t really part of my fantasy, I mostly thought about the cock. Making out for Jake was very aggressive. The roll reversal of it all was strange since I’m usually the one that is more dominant. He had some stubble on his face which was a bit scratchy, not exactly the smooth skin I’m used to making out with.
He stood up, unbuttoned his shorts, and let them slide down his legs and stood directly in front of me. His tight boxer-briefs outlined the length of his semi hard cock perfectly. It was now or never, so I reached up and pulled his briefs down his legs and freed his cock. Still sitting on the couch, his cock was at eye level to me. It looked just like the pictures I had seen. Long and thick, with a well defined head. I reached up and put my hand around it, slowly stroking it back and forth. This must be how a teenage girl feels the first time she pulls out her boyfriends cock.
I kept stroking it slowly as I took in the sight of a now very erect cock in front of me. I saw a small amount of precum starting to leak out of the tip and did what came naturally; I leaned in and licked it up. I kept licking around the head before finally taking it into my mouth. Jake moaned as I started to suck on his cock. I started bobbing my head up and down on his shaft, taking a little more with each push. I had gotten most of the way down when my gag reflex started to kick in. I tried to push past it but it wasn’t really working out so well.
Jake started to take more charge here, and started to force my mouth further down his cock. I could feel his cock as it pushed into my throat a bit and immediately set off my gag reflex. Jake kept repeating this, holding my head down until I couldn’t take it anymore. I don’t know how many times I had done this to Heather in the past, but she seemed to like it. Me, not so much.
Jake stepped back from me, looked down, and told me to get naked since he already was. He must have taken his shirt off sometime when I was sucking his cock and I didn’t notice it. So I did as I was told. As I stood there Jake knelt down and took my cock into his mouth. He got me nice and hard and then put a ball stretcher on me. Not sure what the point of it is but whatever. He has a bit of a nipple fetish and brought my head up to suck on his. He really enjoyed it, but it didn’t really do anything for me. Plus he had a somewhat hairy chest which didn’t help any.
Jake had me lay down on the ottoman in front of the couch with my head hanging off the back of it. He crouched by my head and lowered his cock into my mouth for me to suck on. He only let me go at my own pace for a few minutes before he began thrusting. He started slowly at first, pushing in until I started to gag before pulling back. Each thrust was held a bit longer than the previous time. Before I knew it he was face-fucking me, his balls slapping against my nose with each push. Each time he bottomed out I gagged.
Eventually Jake moved a little higher up and told me to suck on his balls. I stuck my tongue out and licked his sack gently before bringing one of his balls into my mouth. I gently sucked on one ball and then the other, switching back and forth. I ran my tongue around each one as I sucked on it. He moved up again and said he wanted me to lick his ass. I dove right in and started to tease his ass with my tongue. I heard him say he was surprised at how good I was. I told him I used to do it to Heather all the time. He grunted happily and ground his ass onto my face again. I kept rimming his ass, going deeper with each push of my tongue.
With his cock still hard as a rock, Jake came around to the other side of the ottoman and lifted my legs up on his shoulders. He moved his head down and asked if I had ever been rimmed before. I told him that I hadn’t. His responded by saying then enjoy it and he leaned his head down and sucked each of my balls into his mouth before moving lower. Again I felt his stubble rubbing against me, this time it was my taint and hole. Like everything he had done tonight, he dove in and started licking my asshole aggressively. It felt really good having his tongue working the sensitive nerves at the entrance to my hole. I wish Heather had done this to me as I’m sure I would like it better without the scratchiness of a beard.
Jake stood upright and asked if I was ready to get my ass fucked. I was. It was finally going to happen. I got on my hands and knees on the ottoman with my ass up in the air. He told me that he was going to loosen me up with a couple toys. First I felt a medium sized butt plug being slid up my ass. I’ve played with toys enough times that I was able to take it with ease. He came around the front of me and put his cock to my lips while he reached back and worked the plug in and out of my ass. He switched it out and grabbed a bigger butt plug and worked that one in. This one was tougher to get in and stung a bit as the biggest part slid past my sphincter. Once it was in place Jake just let me get used to it. He slowly worked the plug around my hole, stretching it out and relaxing the muscles.
When I said I was ready Jake put his cock to my lips again to get another taste. I hungrily licked and sucked his hard cock. I took it as deep as I could without gagging getting it nice and wet. When I pulled my head back I picked up my camera and got a shot of his hard cock knowing in a minute it was going to be deep in my ass. He had put on a cock ring and his cock was even harder than before. His veins bulged and pulsed with his heartbeat. He moved behind me and told me to reach back and spread my ass cheeks apart. When I did I felt him lay his cock on my ass crack and saw the flash of the camera. He showed me the picture, and there was his big hard cock against my white ass. It looked so big compared to my hole but I couldn’t wait to get it inside me.
Jake lubed his cock up and lined the tip up with my waiting hole. Slowly he pushed forward, letting the head pop past my resistance. It felt so hot sliding into my ass. Feeling little resistance Jake kept pushing his cock deeper into my ass until he bottomed out. His cock felt so much better in my ass than any of the toys I had tried. It was warm and slightly softer than them. And it pulsed inside my ass rhythmically.
Jake realized that I wasn’t having any trouble taking his size so he sped up his fucking. He varied his speed from hard fucking to a slow deep rhythm. Feeling his hard cock filling my ass was better than I expected it would be. Jake started to spank my ass a little, telling me how good I was doing taking his cock. He couldn’t believe that this was my first time taking a real cock. I couldn’t believe it either. I knew that I could take a larger cock from the toys I’ve used, but I didn’t think I could take the real thing so easily. I wanted as much of his cock in me as I could get. I kept pushing back against him when he would pull back.
Jake said he was getting close to cumming and asked me where I wanted it. I knew there was one thing left that I wanted to try with a man for the first time, so I told him I wanted his cum in my mouth. He pounded my ass harder, slapping his hips against my butt cheeks before he abruptly pulled out and moved around in front of me.
I took his cock into my mouth without even thinking that it had just been buried deep in my ass. I sucked on the head has he stroked his shaft and in a few seconds he was grunting as my mouth was flooded with his cum. It didn’t taste as bad as I was expecting, I don’t know what women always complain about. I swallowed of course.
And that was the end. Jake and I talked for a little while after we finished as we both cooled down. Did I enjoy it? Yeah I did. Would I do it again? Probably. It was good to try it out, now I don’t have to wonder about what it would be like anymore.
Source: reddit.com/r/eroticliterature/comments/ccwoex/fulfilling_a_fantasy_mm_first_time_anal