Last night we had our best night ever, again, she said. And she’s the judge. From my perspective, we’ve had so many amazing nights lately that I’m starting to feel like ranking them is hopeless. But every part of it was first-rate, and there was at least one part that really stood out.
I could title this post “Anal” but then I’m afraid it would get all the SEO for the site and become some kind of notorious post, because I’m going to tell you how to have good anal sex that works. So instead I’ve titled it as above and we’ll see if that tones down any attention it gets.
I’m not saying this is the only way to have anal sex, but it’s a way that worked better for us than any other attempt in the last eight or so years, since that year we had anal more or less every time we had sex. Without further commentary to interrupt, here’s how it went down.
- Somewhere in the course of the evening, she rolled over on her stomach and sort of lifted her perfect, sweet ass into the air an inch or two, wiggling it naughtily.
- As always, I love tickling her anus with my fingers (and I guess now my tongue, but I’m not sure that’s going to become a thing), so I asked, “do you want me to touch your anus?”.
- She kind of shrugged, as if to say “up to you,” but also asked, “with what?”. I said “my fingers.” She said “okay.”
- I can’t remember now, but I think she had a hand on her clit while I started working her asshole with the middle finger of my right hand, with a lot of lube (oil to start). It’s kind of a thicker than average finger.
- I VERY gradually worked it in further, twisting it a little, pressing and pulling her sphincter muscles. She was being pretty quiet (kids nearby), but her quivering body and stifled moans told me all was going really well.
- I asked, “if I can get you ready, do you want to have anal sex?” and she said “I don’t know yet.” I said “I’ll keep working on it and let’s see where we go.”
- Again, VERY gradually I worked her up to two fingers, and going a little deeper (up to my second knuckle I would say). It felt a bit like she could use more lube, so I switched to silicone, since that’s longer-lasting.
- Then to three fingers–index, middle, ring, arranged in a tight triangle, and eventually going deep, so her asshole was getting stretched almost to the girth of my penis. I wiggled and teased and jiggled them gently, to keep it feeling good for her, and to help relax her muscles, and I watched her to make sure she was still having fun.
- Meanwhile, I was using my left hand to keep myself crazy hard and spurting precum. She, by the way, was still working her clit with her left hand and coming over and over. Every time she came her asshole would contract mutiple times, squeezing me so tight I had to fight to keep from blowing my load a few times.
- Finally, I judged she was ready, spread a ton of silicone lube on my penis, and straddled her to enter her. From there it was just a cautious, super hot progression–pausing and restarting a couple times when I pushed her too far, too quickly–to being deep inside her with my entire rod. Like at least 5 minutes before she could take all of me.
- Shortly after that, she said “I’m wearing out, so finish up.” I asked, “may I come in your ass?” and she said yes.
- I started fucking her ass deeply and rhythmically, giving her my entire length. I said “I want you to be coming when I come.” She, whimpering, started coming immediately and continuously, and after 30 seconds of perfect heaven I unloaded in her ass, feeling my cum blast out and spread throughout her rectum as I continued to give her all my eight inches.
It was perfect. She said “you sent me to another universe. Only you can do what you just did.” I think we have this worked out now. I doubt we’ll be doing it every time, but we’ve gotten back to where we know how to do it, when we do it. It’s the communication. In the recent past I’ve struggled with knowing that it’s going to take a long time to loosen her up, and worrying that part isn’t pleasurable for her. So in my mind, I don’t know if it’s going to work out–am I going to get in her ass or not? I don’t want to commit myself to it when I know she might not get there, because then I might, in my hormone-addled state, try to go beyond where she’s ready to go. That worry distracts me, and then I don’t enjoy the warmup myself, and I get self-conscious and soften up.
But it’s about the communication, right? This time I talked to her and got her consent throughout, as well as letting her know when we were just working on her ass to see if we might get there, while acknowledging that we might not. When we were both involved in the warmup process, it took pressure off me, I stayed hard, and we got there. And then we had the most beautiful anal sex.
One time when I was talking to a bunch of old friends, like, we’d known each other a long time (some since high school, others middle school or even earlier), my best friend announced to the rest of them (two of whom were also best friends, and the other a long-time acquaintance I’d always liked) that I’d had anal sex. This was, I’m pretty sure, before I was with my goddess; I had had anal with two other people at that point. One liked it because she hated herself (heroin user, bulimic) and enjoyed the pain; the other was an anal virgin and wanted not to be. (She said she’d asked other men to take it from her, and they didn’t want the responsibility of being her first! Fucking losers. God, I’m just smiling at what they left on the table–you could have fucked a girl in the ass, her first time, and you didn’t make the most of it? OMFG. I’m sure they’ve been fantasizing ever since about what could have been.) So I said “yeah, I’ve had anal with a couple women–it’s really good, there’s a different kind of intimacy, plus assholes are just really tight and muscular so it feels different. And it’s so wrong, so taboo, that it can feel really hot too–for both of you. But it can be complicated, you know, if you’re not in the right mindset you can feel like you’re not treating her right, like you’re doing it at her expense, and that is not hot.”
They all thought for a beat, and then with perfect, but unintentional, comic timing the one I knew least well said “But don’t you get shit on your dick?”. I didn’t quite know how to answer. The literal truth is “yes, sometimes” but I can’t say I considered that possibility before the first time I was up a girl’s ass, and one of those first times when I pulled out with a little fleck of excrement and maybe a darker-colored sheen than usual, I didn’t really care. I mean, I’d just come and I’d just done something I thought I might never get to do in my life, so I was in a pretty good mental place. But whatever, you can wash it off. So I just answered “not every time,” thinking a) it was true, and b) if that’s what he’s worried about probably nothing I could say would help him feel better about it. Even so I wouldn’t be at all surprised if he jumped at his next opportunity to stem someone’s rose.
BTW, I find anal is really badly represented in porn. Like everything else in porn you only see the act, not the lead up; and of course you see it from a man-child’s perspective where what the woman thinks and feels is not important. That’s especially misleading when it comes to anal, because you REALLY have to be in the same place. Communicate, communicate, communicate. Oh, and do not be fooled into thinking ass-to-mouth and ass-to-pussy are OK. You can be sure that those girls are thoroughly cleaning out their rectums before and during those scenes. In that case probably ass-to-mouth is OK? But ass-to-pussy is a recipe for a UTI, so do not touch any part of the front with any part of you that’s been in the back.
I should add for documentary purposes that the pussy-fucking was beyond mind-blowing, and again, she sucked my cock better than ever, because she just gets better and better. And I ate her clit for at least an hour, total, and I killed it. OK. It was the best night ever. Hot fucking damn.