I met Sean on Tinder like a year ago. He was very adamant about spelling it ‘Sean’ and not ‘Shawn’. He wasn’t terribly handsome but he was right up my alley. It helps that I prefer to be the more attractive person in a couple. We had a ton of sex, and it was nice that he is older than me, as he also owned his own house. We fucked in his bed, on the floor, even in his car. He had a wonderful dick, not the biggest one I have seen, but perfect for me.

So Sean and I played a fair amount of Dungeons and Dragons. It may sound like a euphemism for something sexual, but he actually was my dungeon master! After one party, he and I were making out, removing our clothing, the usual stuff. I believe we were talking a little about fantasies. He mentioned that he had an unused bottle of lube from when his previous girlfriend said they could do anal, but nothing ever came of it. I had never done anal before, but as long as he was gentle and listened to me, I didn’t really see the big deal. We talked some more, I told him he must listen to me, if I said to stop, he had to stop. Immediately. Things I said would be commands, not suggestions. Only after he agreed to all this did I say I was okay with it.

We did not do it that night, instead we waited until our next date. He never usually let me pay for anything, which was a little irritating, but I didn’t mind too much. For this date, he took me to a local, independently owned restaurant. It was really good, and as I still drank then, we were feeling a little bit loose. After the meal, he bundled us into his car and we went to his house.

I was aware that he had an intense dislike for condoms, but being inordinately afraid of sexually transmitted diseases, I insisted on them. It started like most of our sexual rendezvous, with kissing and a bit of oral. His dick was quite long, but thankfully not very thick so I figured I could handle it. Every time I thought about doing anal, it was like my sphincter contracted, as if to refuse anything entry. Until this decision, it had been an exit only capacity.

Sean was really excited, never having done this himself. He knew my pussy was tight, but didn’t know how tight my virgin ass would be.We began. Our preparation consisted of showering together and getting the lube out and putting it on the bedside table.Finally, we were really ready to start!

He first used his fingers to stretch me out a little. I had, of course, done some research and read that smaller insertions first are ideal. He used his fingers and while it felt strange, it was also quite nice. Not being a man, I don’t have a prostate, so the chances of cumming from this were very slim for me. However, I still wanted to try.

I got on all fours, which was rather a familiar position for me. What wasn’t familiar, however, was feeling a large cock head pushing against my puckered anus. He got the head in and at the same time rubbing my clitoris, he sank several inches deeper inside my ass. It didn’t hurt really, or feel bad. It just felt different. I felt very full. He kept pushing, asking me with every inch if I was okay. When he was as deep as he could be, balls slapping against the back of my thighs, he let out an exclamation, saying, “Your ass is so tight. I can’t last long”, and with that I gave a shove back, entreating him to really let me have it.

Suddenly, I really felt like I had to go to the bathroom. To do a poo. I told him, and despite his protestations, he dragged his hard cock out of my ass and got off me, clearing the way for me to get off the bed. I raced to the bathroom, but with the absence of his long cock, I immediately felt like I no longer had to poo. Still, I sat on his toilet for a bit and tried to bring that feeling back. When nothing happened, I went back to the bed and kissed him, enticing him to start fucking me again.

And did he! Within a few seconds, I was on all fours, my ass lifted up to him and his cock. He gave a groan as he sank all eight inches back inside my ass, my sphincter closing around him and squeezing him as tightly as I could manage. Still, he went slowly, several more thrusts were about all he could take before he shouted out “Oh fuck, I'M cumming. Oh god, oh fuck, feels amazing”. I knew I wouldn’t come from penetration alone, so I planned to make Sean spend a bit of time on his knees in front of me.

With one final, rather quick and rough thrust, he let out a yell and slapped my ass, cumming as he did so. However, he wasn’t quite done with me yet. He immediately grabbed me under my arms and flipped me over, bringing his head down to my pussy. He knew exactly what I wanted, and how to give it to me. His tongue, licking my clitoris, was amazing. Then he got his fingers in on it and was using them to thrust in and out of my tight little hole. It only took a few minutes of this, but I started cumming pretty hard myself.

After that, we cuddled and slowly fell asleep, him performing very well as my big spoon.