First Time In The Back Door

I was about 35 when I first had a**l sex. I’d had the odd finger up there and I’d used dildoes there too, the reason I was a back door virgin wasn’t because I didn’t want to do it, I’d just never been with anyone who suggested it. A girl friend of mine was complaining about a guy she had split up with after a few years of dating, saying one of his faults was that he was a bit “pervy”, that he had wanted to do a**l with her, but she was horrified at the thought.

I still saw him around town at the weekend and one night, Dutch courage on board I got talking to him and I wrangled the conversation around to my friend. He said that weren’t very “compatible” anyway, which usually means one thing; “In the bedroom?” I asked. “A little” he said. “Such as?” I could tell he was somewhat reluctant to discuss it so I went all in with “That either means she didn’t swallow or she didn’t take it up the ar*e”, “Oh, she swallowed” he laughed. “Do you have a massive cock, is that why she didn’t want it up the bum?” “I’ve had no complaints but I don’t think that was the reason” “I guess some girls just aren’t into it” “Are you? You’ve always struck me as somewhat filthy”. Filthy? Cheeky git lol. “I’ve never done it but I’d be up for it” “Why have you never done it?” “No one has offered and you can’t exactly ask” “Why not?” “Because...you know, it’s slu**y” “So?” “It’s a girl thing” “I’d love to pop your brown cherry” he said with a wink.

Long story short, that night we ended back at mine, I had a clean to prepare for the potential activities ahead and he was clearly on the same page, getting his cock out and telling me to suck it. I *do* like a forceful man, I’m quite submissive :) Before doing as asked I slipped in a lubed-up butt plug then got to work on his cock with my mouth. He wasn’t massive which I was glad of, but he was still a good size and I enjoyed having him in my mouth, enjoying even more his dirty talk, telling me he was going to fu*k all three of my holes.

I slipped a condom on him and got into doggy position while he wasted no time getting into hole number two, and with some enthusiasm, fucking my pussy while he pulled and played with my plug. “Are you ready?” he finally asked. I told him to get the lube on his cock and to get it up my ar*e. The plug plopped out, he applied lube to my butthole and also his cock which slid into my butt, somewhat prepared and relaxed by the plug made this fairly easy. I’d had dildoes up there, bigger dildoes even, but this was something else, this was a guy actually fucking me, I was on all fours taking it up the ar*e while being called a filthy b*tch, a dirty sl*t, that his cock was balls-deep in my sh*t hole...the things coming out of his mouth... It wasn’t painful, just uncomfortable occasionally but I was actually enjoying it, not just tolerating it. I knew I was submissive, but this was a new level and he was a great dom.

After doing it doggy for a while he put me on my back, spread my legs and slid it back up my ar*e, “lovely c*nt” he told me, rubbing my clit with his thumb and he continued to enjoy my butthole, and having my clit rubbed really elevated things, was I actually going to orgasm? With a cock in my a**?

Sadly no - all good things come to an end as with a loud groan the condom filled with his cum, him exclaiming how much he had enjoyed it. In the morning there were a few condoms left so we used them for some regular sex but even there he was quite dominant, holding me down, putting me in various positions, explaining in great detail the filthy things we had got up to the previous night, and I was loving it lol. He was very giving too, making me cum multiple times, going down on me, all sorts. Most importantly though it was mission accomplished and I was no longer an an*l virgin.