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.
