A gay story: First Time Ass Fucked I’ve already told the stories of my first time sucking cock and the first time that I fucked another guy, this is the telling of my first time getting ass fucked. After fucking another guy in the woods and seeing the absolute pleasure, I knew I needed a cock in my ass. After I thought about it good and hard, I knew who best I had a shot with.
There was someone that I worked with many years ago that I was still in contact with on social media. To protect his identity (and mine) I’ll refer to this friend as Brian. When I worked with Brian, he was single, young, Chinese and fairly good looking. I noticed over the years, Brian had become a bit more flamboyant and I suspected he was gay. Then, over the last year or so, he started to share photos of who I am suspecting was his boyfriend as he seemed to be about his age and began traveling with Brian.
Brian would often post about being drunk, sloppily drunk even…he really seemed to like to party. We would always message about getting together for a drink or dinner next time I was in town for travel and I thought I’d take him up on the offer. I really wanted to set this up so began messaging back and forth with him regularly. As we were going back and forth, he admitted to me that when we worked together, he was a closet gay and decided to come out about a year ago. I told him I admired him and that it takes confidence to be who you really are and be with who you really want to be with. As our messaging continued, I admitted to Brian that I had always wondered what it would be like to be fucked by another guy. This was a difficult leap for me as he was still connected with some on social media that I still work with. I admitted that I used anal toys when masturbating but always wondered what the real thing would feel like. Again, our messaging continued, telling me how good it feels, what a turn on it is to be fucked by another man, flirting with each other, my visit was coming closer and closer. He never said the words, but it really seemed like he wanted to fulfill my fantasy. I thought I had a real shot. Honestly, I would masturbate often to our messages and as I read them more and more, they really were a bit flirty and obvious.
Now, with my other first experiences, I ended up going farther than I had planned, each time. I thought and planned for it all this time, I was going to go for it. My trip was here and as I was getting ready to leave the next day so I did some mascaping, trimmed nice and neat with a little landing patch (my favorite look) and completely shaved my asshole and ass crack clean, not a single hair. When I arrived the next day, I went straight to the store and purchased an enema. After giving myself the enema, I continued to refill the enema with bottled water and douched my rectum clean. Now I was ready, time for one quick shower before meeting Brian in the hotel lobby bar for a drink.
As I got dressed, I really couldn’t believe I was about to do this, my heart was racing with anticipation. As I met Brian, honestly, it was a bit awkward. I hadn’t seen him in years (except for social media) but our relationship matured so far over messaging, but now I know so much more about him than previously. I had the feeling that Brian had been pre-gaming our meeting a bit as he already seemed a bit tipsy, which I believe is why he began flirting so quickly. We were about our second cosmo into the evening when Brian said “look, I spoke with my boyfriend, I told him of your fantasy and desires to be fucked by another guy.” He continued “actually, I told him that I wanted to help you with your desires and he agreed.” Brian went on to tell me that he and his friend had occasionally brought others into their bed but it has been quite some time. We shared our recent experiences and that we both had (as well as his boyfriend) tested recently and were given clean bills of health, so nothing to worry about.
As we finished our drinks, Brian asked me if I was ready to go to my room, to have my fantasy lived out. As we proceeded to make our way to my room, I was rock hard and Brian certainly noticed and smiled. As we entered the room, I turned the lights on dimly and closed the curtains on the window. I walked over to him and reached in to kiss him when he stopped me. Brian said that he and his boyfriend always had the same deal when with other partners, there would be no kissing involved, no feelings, just pure, raw sex. I was a bit surprised, a bit disappointed but completely understood.
We began to undress and as mentioned, I was at full attention as was Brian. I was really excited and didn’t really know how to start since kissing was off the table and he broke the silence with a very clear “now, I’d like you to suck my dick, get me nice and ready.” I obliged by dropping to my knees, taking his cock in my right hand and sucking on the head, licking around, pushing my tongue on the hole, getting a little taste for sure. He had a bit of a small dick, but it was very nice and hard. I was able to take him all the way into my mouth, sucking hard while cupping his balls. Brian also was mostly shaved, which makes sucking cock so much more enjoyable. I could tell I was making a bit of contact with my teeth as he would pull back a bit but what could I say, I was a bit new at this. Then he said “that’s good, I’m good and ready to stick my cock in your ass.” He helped me stand back up and turned me around pushing me on the bed, with my knees right at the edge.
As I was getting ready, I felt his tongue licking and sucking my asshole. He complimented me on my clean shaving and clearly clean asshole and that I must have been planning for this myself. Then he asked if I was ready, which I was having a hard time speaking and managed to mumble “yes.” He grabbed the lubricant that he had brought with him and lubed my ass up so good, wiping his cock, ensuring entry would not be a problem.
Then I felt it, the head of his cock was pushing on my asshole. Brian re-assured me he would go slow in the beginning to get me used to his cock. As he pushed in, yes, it hurt, it hurt pretty bad and I asked him to stop a minute. I would have this when I would use dildos, it would hurt at first and then try again and the hurt would fade. Once I felt the pain go away, I asked him to try again. He pushed in and yes, it still hurt a little but like with the dildos, the pain quickly went away. Brian was gentle, definitely going a bit easy on my ass in the beginning. Pushing all the way in, it felt so good. He kept going in and out real slow, pushing each time farther and farther. I reached back with my right hand, trying to pull his ass so he would be deeper and deeper, this was everything that I fantasized about.
Then he began pumping me a bit faster, he was really getting in to it. We were in a rhythm and while at the same time, arching my back up and down. I was really learning how to manipulate his cock inside me, where it felt good, where I didn’t care for it as much, what position gave the deepest penetration. When he stopped pumping, leaving me deep inside him and he asked me if I would turn over on my back. “YES, absolutely” I replied.
As I rolled on my back, he lifted my back off the bed by pulling me up by the back of my knees getting me in just the right position. Then, he pushed right in again. No pain at all, I was really loving getting fucked. Now, I could watch him work…he was a very passionate lover, putting everything in to our time together and everything he has, deep in my ass. As he kept fucking me, he pushed my knees further and further back, giving him deeper and deeper access. Honestly, I felt like a real slut in this position as he grabbed my ankles and spread my legs wide, while on his knees pumping away. As he lowered me back down a bit, I held my own legs open and up as it felt wonderful and clearly, that’s how he wanted my asshole. Then, he reached down and grabbed my cock that was rock hard. Brian said “I’m slowing down a bit as I want you to cum before I do” and he started jacking me off while his cock was moving slowly in and out of me, pushing deeper and deeper.
This sensation was one that I never felt before, it felt like it was building and building, stronger and stronger and then finally one last jack timed with deep push and I blew my load. This was the strongest orgasm I had ever had and it felt like it wasn’t going to stop. I was cumming like I had never cum before, the cum actually hit the bottom of my chin and all over my chest and as my orgasm faded, I knew it was time for Brian to finish. Again he raised my legs high and wide, I felt like such a slut. He was sweating and really pounding my asshole fast. I reached up and started pinching his nipples and he began to tense up. I said “I want you to cum in my asshole, I want all of it, every last drop.” Saying this and pinching his nipples was enough as he pushed deep inside me and I could feel him cumming in my ass. He kept his cock deep in my ass after he came, just absorbing the moment and he lowered his chest to my cum filled chest. We laid there for what felt like 10 minutes but was actually like 10 seconds and I could feel my asshole pulsate. As he pulled out, the cum squirted out. It was official, I had finally been fucked by another man, my friend creampied my asshole and I loved every minute of it.
We ended up taking a shower together really didn’t touch each other for the remainder of our time together. I told Brian how much I appreciated him making my fantasy come true and he commented how much he liked cumming in my asshole as we joked about it. We talked a bit about getting together again on my next trip. I asked if his boyfriend would like to join as gay spitroast porn is one of my favorite to jack off to. He said he’d talk with his friend and let me know.
We haven’t messaged for a couple of months but will reach out to him for my next trip to town. And hopefully, he can make my next fantasy come true too.
I don’t have any other experiences to write about at the moment but I will be sure to tell my story after the next chapter so it may be some time. I really love to read the comments when you leave them. Reading the encouragement, your feedback and you sharing your experiences is something that makes me real horny. So, if my story of my first time being fucked has made you hard, please let me know. If you’ve been stroking your cock while reading and especially if you’ve blown your load thinking about my experience, please let me know in the comments!