Well it seems i’m continuing on my journey of sexual exploration. I have been hooking up with those two roommate guys I have been writing about more and more often, and almost every time we hook up they seem to have something new for me to try out. Lately every time they fuck me they keep telling me that my asshole looks so tight and fuckable. One of them was railing me from behind the other day and he took his thumb and started teasing it while he pounded me. He kept asking me if he could try fucking it and I kept telling him no because I was too afraid.
I get that it looks and seems hot but honestly it just feels so tight to me and I had a hard time believing it was even possible. As time went on though I started to feel more comfortable with the idea. A few days ago while he was teasing the outside of my asshole with his thumb I decided fuck it. “Put your thumb in my ass” I told him. He pressed his thumb against my hole and it popped in.
He used it kind of like a handle to fuck me even harder and when he came he pulled me as tight against him as he could to make sure it got as deep into me as he could. It was after that session that I told him I would be down to try anal. He looked so fucking excited ahah. Not gonna lie I was too.
The next day we finally did it. The night started off normally and we ended up starting to hook up on his couch while we were watching a movie. He started eating me out but this time instead of just focusing on my pussy and clit his tongue went lower. He started teasing the outside of my asshole with his tongue and he used a lot of spit to get it all wet. It was actually feeling really fucking good and I got more and more excited to have him finally fuck my ass.
He went into his room and when he came back out he was carrying a butt plug in his hands. I had no idea he even owned one but I felt a sense of relief because I figured that would warm me up and make things hurt less for me. He also brought some lube. He had me bend over and he licked my asshole again for a few minutes before lubing up the plug and sliding it slowly into me.
Once it was inside he pulled out his cock and started fucking my pussy. It felt fucking amazing i’ll tell you that. Feeling the plug in my ass while he pounded me from behind was so satisfying I loved it. He started pushing the plug in and out of me while he fucked my pussy and the same time and after a few minutes I started to cum. My orgasm shook through my body and I came harder than I ever have before.
When my orgasm was finally over he asked me “Are you ready?”. I moaned in affirmation and he pulled the plug out of me and pressed the tip of his cock against my ass. I told him to go slow and he promised that he would. All of a sudden the tip popped in and holy fuck it felt big inside me. He went really slow and used even more lube and it took at least five minutes for him to get all the way inside me.
He held me by the hips and started to stroke in and out of me. Over time he started fucking faster and faster and he started spanking my ass with every stroke. It had hurt a little bit at first but over time it started feeling better and better and I started to feel intense pleasure.
He started fucking me even harder and I was moaning like crazy at this point. All of a sudden I started to cum again and I was practically screaming from how intense the orgasm was. I started to beg him to finish inside me. “Please cum inside my fucking asshole!” I screamed. He grabbed my hips and pulled me tightly against him causing his cock to fully enter my asshole. He started to cum and we moaned together as he came inside me.
When we were done he held me in place for a few moments while we caught our breath before he finally pulled out of me. I felt his cum drip out of my ass and he grabbed the plug and pressed it back into my asshole to hold all his cum inside. It was kinda gross but also kinda hot at the same time.
We cuddled and talked about the experience afterwords and he brought up the idea of him and his roommate fucking me together. He asked if I would be open to having my pussy and asshole fucked at the same time. It was a crazy thought but I realized I would actually be down for it. Just thinking about it and writing about it right now is getting me all worked up and I can’t wait till they invite me over again so I can get double fucked for the first time in my life. Will def update you guys once it happens haha.