Buttsex: The First Flight

This week, Girl On The Net offers up three anecdotes of being a guy’s first time receiving a strap-on up the arse. The first and third are awesomely hot, the second one, as a counterpoint, is entitled “The disappointed” and is a story of how it didn’t quite work out as planned, and thus was not quite as hot, but a useful caution: not all fantasies turn into hot sex when you try them out. (It does have a happy ending, via handjob, though).

Two things struck me about the post, that are related in a subtle way (arguably one of those things is really two different things, so there’s three things in total; but those are much more closely related, and less subtly, so they count in my mind as one thing. With me so far? Good)

The thing is, I love anal play of all kinds. I love doing it to my partner, and I have experimented with self-insertion and so on and loved that, too. So naturally, I want a partner who’s going to be willing to get a strap-on and give me one. Indeed, my favourite F/m (female-Dominant/male-Submissive) porn typically has a guy taking a strap-on up the arse. It’s an experience I am enthusiastic about at least trying out (bearing in mind that it might not be all I hoped for, see that second story…). I would like to be, at least in attitude, like her third story:

With the third guy, I knew he’d been wanting it for a while. Playful conversations about me fucking him had led not to giggles or ‘maybe’s but to a very open, certain ‘yes please.’

I couldn’t ever give, “A bold declaration that he knew this would be good” the way he did before a first time, though. Ultimately, for my first time I will need something different than what GOTN celebrates. (Obligatory statement of “YKIOKIJNMK”.)

The first problem I have is one of language. The term GOTN uses to talk about the activity is “pegging”, which I accept is in common usage and have seen generally used. Unfortunately, I find this term to be very uncomfortable, and it doesn’t sit well for me with the way I want to conceptualise or experience the activity.

While I enjoy the graphic metaphor of the term, somehow for me it also carries disconcerting connotations of belittling, humiliation, or contempt for the recipient. (I hasten to note that I have no belief that GOTN feels anything like that about her partners in the anecdotes she gives, and nothing about them gives me any reason to say she would.) It has the same feel in my mind as words used to denigrate female sexuality, or femininity in general. (This is why I hate the language surrounding male-sub crossdressing, such as “sissification”. Whether I’m top or bottom, if I’m going femme, I’m proud, not ashamed, of my femininity.) I don’t know if others see those same connotations, and don’t know for sure why I feel this way. Maybe this is just a quirk of my mentality. All I know is that the same type of discomfort and unpleasant sensations run through my brain when people talk about pegging, as when they use disparaging language about other sexual behaviour, especially sexual behaviour by women.

This leads into the second aspect (or two inter-related aspects). All three of GOTN’s anecdotes put her partner in a Submissive or bottoming role:

Guy #1 “He obeyed immediately. Quivering with lust and nervous about being fucked for the first time, he stroked himself slowly, not wanting to come before I’d had him.”

Guy #2 “The fucking itself was pretty hot – feeling the power of being above him, on top of him, controlling his pleasure with every inch of my fake cock.”

Guy #3 “He was blindfolded, strapped by the wrists and ankles to the bed frame.”

I want to be able to take it as a Submissive act, but I don’t conceptualise it as intrinsically that, in the same way that I don’t attach any humiliation, lowering, or belittling to it either. It’s about the pleasure, the contact, the sensations. What roles you lay over that (as with any sex or BDSM act) is up to you. It bothers me a little that the feedback described is all top checking in with bottom, and not spontaneous two-way talking (of course, it may be that the third guy’s feedback is covered by, “Instead of wincing, however, he urged me on – more, harder, deeper.”)

As much as I would like to be like GOTN’s third guy, all “Wahey, let’s go!” and ready for “a first time pegging that was full-throttle”, that’s just not how it could happen in r/l. My first time, I’m going to be the one in control. The slightest move without my say-so, at least to start with, would feel like a huge violation and that’s going to bring it to an end immediately. Needless to say, there’s going to be no blindfolds or bondage that first time. (For one thing, bondage is a huge headfuck for me anyway, so probably not healthy to mix the two for the first time.)

So the scene in my head, the way it would have to unfold for me to have the best possible experience that first time, starts with me getting her ready. I help her into the strap-on, help apply the lube, instruct her to lube me up. The image in my mind is that we do it standing up. I bend over, leaning on a chair back or the edge of the bed. I’m going to do this by feel, I want to concentrate on every last sensation and listen to my body and communicate to her how to respond. I don’t care how experienced or not she may be, it’s my first time and I need to teach her how it works for me.

Picturing the scene, I imagine feeling that lubed-up cock nudge against my buttocks. Sight isn’t going to help me now, but I’ll probably stare at the duvet rather than close my eyes. I tell her to push gently, slowly increasing the pressure. At the same time, I’m willing my sphincter to relax. When I’ve played with buttplugs or dildos before, it’s always taken time to get that to happen. So at some point, I’ll just know that I need her to stop pushing and just work on my own determination, and push backwards to meet her cock rather than have her come forwards with it. Here, reality would probably involve the cock slipping off up between my thighs or my back instead of inside. So we try again, I tell her to hold it in her hand, keep it steady, we go through the build-up of pressure again, until, again, I stop her and work on it myself. In my mind, it works perfectly first time: there comes the awesome moment where the muscle gives way, the tip enters.

“Yes! There it is,” I say. Maybe she gasps or reacts as well (she can see what’s happening, I guess). We both hold it for a moment. I’ll settle my weight forwards, I want her to do the work now (again, reality probably involves “oops, it slipped out again!” and fiddling around getting it back in; the fantasy is much smoother). I want her to fuck me, and I’m going to tell her how.

And this is kind of where the related issue kicks in. It’s one of expectation. I’ve started to sketch out a fantasy of how I might get someone to bugger with a strap-on, but already I’ve talked about ways in which it’s going to be unlike a fantasy when it happens for real, because human bodies and physics and stuff are complicated and awkward and not likely to behave exactly as we want straight away. And I’m a little clumsy. So, you know.

GOTN writes:

#1 “I stroked his prostate, very gently, and felt every muscle in his body tense as he tried not to come. I’d never been so powerful. ‘You’re going to come when I fuck you.’ … ”

#2 “I wanted this next guy’s reaction to be the same. A wide-eyed ‘oh God it hurts but please don’t stop’ building to a shuddering, twitching, frowning climax and spunk plastered liberally over the head of the bed.”

#3 “The best is a guy that takes that enthusiasm – that desperate horny lust – and begs for more of it until I can fuck him with power and force and the kind of all-out brace-yourself energy that he’ll aim for when he’s fucking me.”

I haven’t found a way with solo play to get myself to come from anal penetration; typically, when I’m playing that way, I don’t even get an erection. Maybe with someone else there to do it to me, I would find a different result but being on the end of a buttfucking is not, in my mind, about coming, or even orgasm (at least, not as it’s usually conceived for male-bodied types; more data needed to say whether there’s an alternative orgasmic-type experience involved). So far, it has all been about what GOTN calls, “exactly that ‘filled’ sensation”. And that’s such a good feeling, it’s enough to make me want to try with a partner.

I’ve never stimulated my prostate or knowingly had anyone else do it (on purpose) either. I don’t know what to imagine or expect. I don’t know what sort of response, if any, my body would produce when I get to try it. My assumption is that it’s probably not going to be as amazing as I’ve heard (in the same way that, to date, PiV has not been amazing, and orgasm hasn’t been a primary concern for me during sex).

For me, the first time ever is absolutely going to have to be experimental. I just want to find out how it works, establish a baseline for future exploration, by figuring out my own body with the enthusiastic aid of a woman who wants to fuck me in the arse. As I said, PiV has not been a big hit with me so far, but when it comes to sex with a partner I feel a lot of pressure to have an orgasm with her present, at least. To feel that same pressure when I’m only interested in exploring, and when i don’t know what my body even does with the stimulation we’re planning, would undoubtedly put a sour veneer over the whole enterprise. “I’m going to make you come”, “I’m going to play with your prostate and make you feel wonderful” – what if I don’t? What if, for me, prostate play is “meh”, what if however much I enjoy being buggered, it isn’t that sort of pleasure? What if I let her down? What if what she expects to happen means she ignores at the final push what I am actually getting out of it and spoils things by trying to produce an effect that isn’t going to happen?

I don’t want expectations for this. I want my partner as excited by discovery as I am, where any outcome is a good outcome because we found it together and it’s new. So I’m going to say I’m ready, ask if she’s ready, then it’s “Okay, start pushing. Slowly, now. Unf! Steady, steady.” Maybe pause for me to breathe deeply. “Okay, a bit more. A bit more. Yes, like that. Oh, that’s good. How does it feel for you?” And so on. We’ll see just how deep I can take it on that first go, rest a while with my rectum filled, talk some more about how it feels, how we feel, what she can see.

“Okay,” I’ll say at last, “Start fucking me slowly. Ease out and ease back in again.” “Yes, Sir.” I’ll give her constant feedback, whether verbal or just vocal, and I’ll want feedback from her, too.

I don’t know the rest. That’s why I want to do it, not just try to imagine it. If I want my characters to have anal sex (there’s an anal sex scene I just loved writing in my novel, for instance) I can use what I’ve already experienced, combined with others’ descriptions, to build a vivid picture. But what my body does might be different.

* * *

This is just about what I need from my first time. My second or third might end up being very like the scenes GOTN describes. I certainly want there to be a time when I am bottoming, in a submissive headspace (even if I wanted to go there, I couldn’t on the first time because that wouldn’t be fair on my partner who is expecting me to be in charge for that scene). When I’m comfortable with a partner and the deeds, bondage would be a real experience to try with it. And so on. GOTN’s scenes worked for the guys she was with, and for two of them, it was pretty awesome. This post is just using seeds planted by her post to let me write about me, how I relate to the act, and what would work best for someone who wanted to do me that way (a lot of it goes for gay sex as well, incidentally).


About ValeryNorth

I overthink everything.
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2 Responses to Buttsex: The First Flight

  1. kdaddy23 says:

    I hope you eventually find out what it’s like and then come back and share it with those of us who’d be interested. I’ve had the real thing in my butt (too many times) and while I once found it damned enjoyable, I’ve never had a woman break out a strap on and want to do me like that; I’ve asked a couple of women and while they thought it sounded like a good idea, nothing ever came of it.

    I’m not a fan of the word “pegging” but I guess it had to be called something. I know a couple of guys whose wives peg them on a regular basis and they say it’s better than the real thing – and I just have a hard time believing that. I did find it odd that they would enjoy their ladies banging their butts but wouldn’t consider having the real thing inside of them…

    • ValeryNorth says:

      Thank you kindly 🙂

      Assuming by “real thing” you mean “biocock”, I think different strokes for different folks. I am sure there are bi women who prefer biocock and those who prefer strapon cock, for example. The same will be true of men and varieties of buttsex. I am sure the sensations from various materials of sex toy will differ greatly from the feel of engorged erectile tissue (and yes, I would like the opportunity to research these differences!)

      I’m sure if I ever get to try receiving anal with a partner of any gender and equipment, I will eagerly blog about it the next day. But just because it feels a certain way to me, doesn’t mean anyone else would have the same experience. Which is kind of what the OP is about.

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