If I had a sex bucket list, an item would be crossed off.

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 aย 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?”

He did.

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 actuallyย 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.ย 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.

40 thoughts on “If I had a sex bucket list, an item would be crossed off.

  1. Ha! Fun. So glad it was enjoyable for you both.

    You were amazing for your first time (seriously, pegging takes skill and practice, just like PIV sex). Also don’t give up on having him on his back: doing it face-to-face is hugely intimate-hot-awesome. Also you might just need a longer dildo for that position.

    I always feel like a debbie downer with this, but I cringe every time someone says ‘gel’ or ‘jelly’ toys. Google ‘toxic sex toys’. Then replace it with silicon.


    • My friend Madame said the same thing to me about talent – she was surprised when I described what I was able to do and how quickly I got into a rhythm. She said it’s unusual – I was rather proud of myself.

      Definitely need a longer dildo. I literally had no clue how to get my body into a position where I could do that face-to-face! I suppose I could have had him prop his ass up. But I was clueless.

      I did check out what you suggested; this toy is from Doc Johnson which is an American brand that seems reputable, and it is phthalate free…which I think is the big concern, right?

      • Ha! You SHOULD be proud of yourself :).

        Two things with jelly materials: Yes, phthalates, but also porosity which makes them hard to clean.

        Read this (about Doc Johnson (allegedly) lying about the composition of one of their toys) and this (good links and information about toxicity but also info about porous toys and cleaning), both from reputable sex bloggers/educators.

        Chances are you (and he) will be fine. Lots of people use those toys and never have a problem. But I wouldn’t stick them in my body, or my partner’s: the risk just isn’t worth it.


  2. Hey! Why didn’t I see this post in my reader? And where the hell is the like button?
    I have to admit that pegging has never appealed to me. But I’m sure that, with the right partner, I would be willing to try it, for them. And who knows, I might even find that I like it ๐Ÿ˜‰
    Good for you though!

  3. If you ever need a stand in sex partner (like you’re ever wanting for company when you want it, lol) I’ll be happy to volunteer!!

    I’m so happy for you, and jealous that you’re having such fun exploring. I too have been worried that my wife would see me in a different way if she were to peg me, so I’ve been really reluctant to suggest it, even though we’ve done just a little anal play on me here and there.

    I’m not sure just how small the dildo you were using was, but it really shouldn’t matter in terms of him laying on his back. The key is him getting his ass up in the air high enough to line up with your dildo. Unlike when you lay on your back and simply put your legs on his shoulders for vaginal, his asshole is further back, so him just putting his legs up won’t do. He could use you as a brace, but you really have to lean well forward so that you force his knees up towards his shoulders/ears. I have been with a guy who had a headboard on his bed that had a perfect groove on the underside of it. I could get my legs up and sort of lock my toes in the groove and it put my ass on the perfect level for him to enter. And I have to agree that for hotness and intimacy (especially since you don’t feel it) there is nothing better.

    Most women seem to have a hard time with doing the fucking, because they don’t feel it, and they don’t know how to move. It can be a little disappointing as a guy, but with a little practice I’m sure you’ll be awesome!

    • I will definitely let you know if I need a stand in ๐Ÿ˜‰

      Fox is 6’4″ so I’d worry about my ability to take his weight with his legs on my shoulders! I will figure it out – I am pretty sure he wants a repeat.

      You should ask your wife of you are curious. I think if you direct traffic per se, topping from the bottom, then it’s less submissive, right?

      • You’d only be supporting the weight of his legs really, so it should be something you can manage, even if he’s bigger and outweighs you by a lot.

        I’m working on working up the courage to breach the subject with my wife. Wish me luck.

  4. I smiled quite big when I read this as I remember the first time I pegged B. It was all kinds of awkward, exciting, fun and erotic. Kudos to you for trying something new. ๐Ÿ™‚

  5. i really love that you don’t have a sex bucket list, and your reasoning behind it. i additionally love that you are celebrating something that you were able to do under the right circumstances for you and Fox…

  6. I agree with your idea of a list being limiting. From my point of view that defines things. Chances are, if left to my own devices without a list I’m likely to get more creative. I guess a mental list is ok, but as long as someone isn’t rigid about it. (insert your own “rigid” themed joke here)

What do you think?