I don’t have a sex bucket list. I actually find the notion to be limiting rather than freeing.
I suppose I’ve actually already done a hell of a lot, so there’s that. I was 18 when I had my first MFM threesome.
But, I can only add things I am aware of (and I’m constantly learning of new sexual things out there). If I don’t check something off a list, not only does it run counter to my nature, it makes me feel like I’ve failed.
Also, because I’m driven to cross things off my lists and I hate to fail, it could drive me to do something just because it’s on my list, rather than because the situation and person is right.
Bottom line is, for me, it engenders the wrong behavior and has the chance to limit and hurt.
I’m weird that way I guess.
That’s not to suggest there aren’t things I want to try. They are in my head, not written down, and I wait for the magic trifecta of right time, place, and person (or persons!).
Tuesday night was one of those nights.
Fox and I had been out, separately, with colleagues. We’d both had a few drinks. When I was on my way home I texted him and he was still out – at a bar that’s pretty close to my house. It was also the place I first met Will, my ex.
I told Fox he could come over if he wanted. He did.
I’m not even sure how we got on the topic (I literally have zero recollection at the moment), but we decided it was time I tried pegging him. He was super keen and super excited. I wasn’t so sure how I would respond.
We went upstairs and I went to my toys and pulled out the two I purchased to use on him – one was a 6″ lifelike dildo and the other was a pink gel one that was slightly skinnier. He chose the latter. I grabbed my never-used harness (which I purchased two years ago when dating Ariel, who wanted to be pegged) and attached it.
Fox basically growled at the sight of me naked and bent over my nightstand fussing with the harness. He started a pretty hot session where he took me from behind, us both standing beside my bed. It was raw and not tender. He didn’t cum and eventually my legs started to give out and so I said “hey, would you like me to use this on you now?”
I put on the harness and lubed up as he crawled onto my bed face down, ass up. I kneeled behind him and needed him to adjust the height of his ass so I could line myself up properly.
I started slowly, remembering what it’s like for me when someone tries to go too fast with me anally. I could feel resistance at one point and just stopped until he relaxed. But overall he took it pretty well and pretty quickly. He immediately started moaning and saying “Ann, that feels so fucking good”.
I pumped away as he moaned and sighed and tried to also manually stimulate himself.
Being the one doing the fucking was a strange feeling for me. I was definitely the one in control. I could grab his hips and go faster or slower at my own will. I’m not sure I liked being the “top”, although it wasn’t as dominant a position as I thought it would be. He was in what I considered to be a submissive position but just 10 minutes before, he’d been very much in control.
I was worried after pegging him (just like the night he worshipped my shoes) I would see him different. That wasn’t the case I was hugely relieved.
It was also strange to not actually feel him. It was only through his reactions that I knew he liked it.
He was unable to manually stimulate himself at the same time, given the position. I tried the reach around but his body is too long and it was hard to do both at the same time. I have a new appreciation for men who can fuck and use their hands to stimulate at the same time. Props to y’all.
He asked if he could be on his back. Literally, that was impossible for me to do. Lesson learned.
So I took off the harness and gave him a blow job until I decided I wanted him in a different orifice. I put a butt plug in his ass and rode him until he had a spectacular orgasm.
I was rather pleased with myself and slept pretty damn well that night.