What what, in the butt

I fucked someone in the ass for the first time over the weekend. It was pretty cool.

It was Furby, my old friend and a regular partner of Master's now that she's in the same city as him. She looooves ass play (in fact, I think she's the one who first told me that hey, girls can like it too), so when she was with Master and me we decided to double-stuff her because I'd brought my little ass dildo along.

At first I was pretty scared, because my own ass is very tender and I have to be very careful with anything going up there (though I usually love it once it is). But I made sure to use plenty of lube (and a condom, natch), and she was having a grand old time, and soon I was too. I've watched her get fucked in the ass before, and the noises she makes when she comes from it are unmatched. I mean, goddamn that woman has a set of pipes.

Once I got over the initial fear of hurting her, it really wasn't that different from using a strap-on for PIV stuff. I can't really feel anything, but there is a psychological thrill to eliciting such strong reactions from someone. I always worry that I'm tiring too quickly because my muscles aren't used to moving that way during sex, but afterwards Master always comments on how hard I was going to town on whomever I was with, so I guess it's not really a problem.

I think the one thing I didn't like about it was the smell. Which I know is kind of inevitable with buttsex, but it's still unpleasant when it occurs.

Master asked me afterwards if I wanted to peg Ume, because Ume had expressed passing curiosity in it in the past. I'm honestly not sure. I can see myself doing it for his sake, as a sort of fun experiment, but I have to admit that the thought of it doesn't actually turn me on. It's kind of a sure, why not thing. It doesn't help that Ume is so much taller than me, so I have a harder time imagining the logistics of it.

Frustratingly enough, I still can't take Master in my ass - not even one of his fingers. Even though I can take my ass dildos, which are bigger than his fingers; it's one of my new favorite ways to masturbate, in fact. I'm not sure what the problem is; maybe Master isn't using enough lube? I think he's trying to do the in-and-out motion too quickly, because when I masturbate I slowly get the whole dildo in before doing any in-and-out. (And even then, I usually don't do very much.) And dildos don't have body heat! I think that has something to do with it too. Also performance anxiety.

Sigh. If we were able to be together more often I think I'd be able to manage it.

Square peg, round hole?

Master and I have reached a meeting of the minds, as it were, with our old friends Ume and Gene, and now we swing together* whenever our schedules allow.

We have a planned rendez-vous later this month, and last night I chatted with Ume about what we'd like to do the next time we meet. Eventually he brought up that, though this month's meeting would be too soon for comfort, sometime in the future he'd be interested in perhaps trying pegging.

I've considered whether I'd like to try pegging before, and I must say that I find the idea a little weird, though not so much that I'm unwilling to try it. However, I'm trying to determine what the source of my disinterest is.

Part of it is that I'm not confident in my ability to avoid hurting Ume - it's the same reason I'm hesitant to anally penetrate anyone, male or female. However, there does seem to be something to woman-on-man penetration that I find mildly off-putting in a way that man-on-man, woman-on-woman, and man-on-woman penetration are not. This makes me think that my discomfort is a result of socialization.

This doesn't quite make sense to me, even though that's where the evidence points; after all, I enjoy fem dom/male sub as much as any other permutation of genders and power dynamics. And even then, penetration doesn't always equate with domination anyway - so why does the specific scenario of a woman penetrating a man cause this reaction?

My frustration with the irrationality of the whole thing makes me more keen on trying it at least once, to see if I can overcome the socialization that I believe is affecting me. However, I think this does raise a larger question: how do we find the balance between owning our sexual preferences and working to undo sexist/racist/whatever conditioning? For example, while it's okay to find, say, Asian women attractive, it's not okay to fetishize them as "exotic" or anything like that. How do we discern what is a genuine and/or benign preference and what is a problematic mindset? (And that doesn't even get into the post-structuralist idea that there is no such thing as "genuine" sexual attraction or gender expression. (Yes, I've been reading Judith Butler lately, how did you guess?))

In any case, as I said, pegging is something I'm willing to try. Maybe once I'm actually performing the act I'll find out it's actually awesome; maybe I'll grow to love it, like I did with spanking. Or maybe I'll just be "meh," but at least I can say I tried it. There are very few sexual practices that I'm willing to dismiss offhand.

*I get the impression that "swinging" as a concept has something of a sour flavor for the poly community in general, but that really is the best way to describe what we do, I think. However, I'll save that for another post.

teh analz

Master and I have experimented with anal play in the past. It was easier when we lived on the same campus, since we saw each other all the time and could work on it regularly. But then he graduated, and both of us bounced around the country (or the world, in his case) for a while, which isn't conducive to a regimen of any kind - especially a sexual one.

But now we've both settled down, at least for the medium-term, and so it's time to start once again. It's a little bit trickier since we're still in separate cities (albeit only 3 hours apart), but it was an obstacle easily overcome with TECHNOLOGY! I.e. silicone.

I found an awesome feminist sex shop in town and went to them for guidance. It was there I learned that anal training isn't about "stretching" anything - it's not even about getting used to something of that size up your butt. Instead, the goal is simply to become more aware of your muscles and to learn how to consciously relax them. I was glad to learn this, since the Master's-penis-sized toys they had available were a lot scarier (and pricier) than the smaller ones. I ended up purchasing one that's somewhat larger than an average man's middle finger, and in a very pleasant purple that matches the very first dildo I ever bought.

I wasn't expecting to accommodate the entire toy on my first try, but I did it with much greater ease than I ever managed when Master played with my ass. I think it's a combination of being more relaxed on my own - no performance anxiety! - and I was already somewhat used to the sensations. When I was with Master this past weekend, however, I started tensing up again, and it wasn't as easy. I'm also not able to handle any in-and-out motion yet. But I'll keep working on it!

Anal wouldn't be nearly as pleasurable if I weren't a masochist, I think. That isn't to say it hurts - I'm so paranoid about damaging something sensitive and important that the slightest hint of pain signals game over for me. However, it definitely isn't pleasurable in the same way that vaginal sex is. It's intense. I kind of want to compare it to a deep-tissue massage. And as a masochist I think I tend to interpret more kinds of stimulation as "pleasurable" than the average Jane, and I'm more open to incorporating them in sexual contexts.

Nevertheless, I'm glad that Master doesn't fixate on anal as some sort of sexual "holy grail" in the way that some guys seem to. He describes it as "Dominant icing on the cake of sex," which I think is a great way of looking at it. It's a lovely treat, but it's not the be-all-end-all, which means he doesn't get frustrated when I can't take him in my ass - something that happens quite often, since I still need to work on getting over that performance anxiety.

He mentioned he might get me a butt plug with a kitty tail on it. That would be awesome. :3

Progress & expectations

I'm coming along well in my anal training. I can take Master's cock a good way past the head now, or so he says. I can't really see - but it feels like a lot! The biggest obstacle I need to overcome is the width, methinks.

Master also administered an anal douche last week. It was a very strange experience; the water was very warm, and it made me feel all full and a little bloaty. We did a bit of impromptu medical roleplay, where he was a kind, young country doctor running a clinic out of his home and I was his shy, embarrassed patient. It was fun, but I think what I really want from medical scenes is the evil!doctor - something closer to a mad scientist figure - that subjects poor widdle me to all sorts of nasty experiments.

Kind doctors aren't terribly sexy to me because they aren't a fantasy; they're the kind of doctors I meet in real life. I've had the fortune of never being subjected to immoral medical practices, so I can afford to build up images in my head of a cruel doctor without having to actually experience the terror of being medically violated.

In that way, I suppose, its similar to how/why I experience rape fantasies. Though obviously people who have similar fantasies are going to have vastly different reasons. Kind of like convergent evolution - starting from disparate psychologies, two people can reach similar sexual profiles.

"...Then came home and fucked my sister."

The brother/sister roleplay was hella fun. I was in character as soon as Master opened the door for me, and we didn't break character until we were lying together on the bed going, "....Whew!"

Master and I are both actors and we both play table-top RPGs, so I think we applied a lot of that to our playsession. The only problem is, I'm not the greatest at improv and I didn't spend a whole lot of time thinking about my character beforehand. "Her boyfriend just broke up with her... and she wants to bang her older brother," was about the extent of her characterization. Still, I think I did all right.

I also discovered that seduction is DAMN HARD. I don't really seduce very often (which is partially why Master wanted to do this scenario), and what made it even more difficult was that we both knew it was a farce; I wasn't really seducing Master, since he already wanted to sleep with me, but we both needed to figure out how many of the perfunctory motions I had to go through before he could "cave." It's a delicate balance between "LOLOK" and completely shutting my advances down.

The sex itself was... frantic. It was desperate. It was guilty. It was awesome. Throughout the entire scene the sexual tension was thick in the air, and I was wet even long before the first kiss. Though, as Master remarked afterward, "It was hard to think of something to say other than, 'Oh, Sibling-Pronoun.'" At one point I almost slipped and called him Master, but I stopped myself. :3

However, throughout the entire scene I had the weirdest urge to say something completely off the fucking wall. Like when my "brother" insisted on using a condom, I had to bite my tongue to keep from saying, "Yeah, we don't want any freaky-deaky inbred babies!" And in the middle of sex it required some real willpower to keep from saying, "Oh man, you fuck just like Daddy!" I have no idea why I wanted to say weird shit like that. I mean, yeah it would have been hilarious, but it would have entirely broken the mood of the scene. Which may have been the reason - I wanted to remind myself (by forcing Master and me to break character) that this wasn't real, that we aren't actually siblings.

Or maybe I've just heard one too many "inbred hillbilly" jokes.

You know, this is going to sound weird, but the sexual tension in the early part of the scene actually reminds me of when Master and I first started dating. (Three years ago! My, how the time flies!) Before we started having sex - before we even kissed - Master would invite me over to his room for "platonic sleepovers." We would both be fully clothed and wouldn't do anything else besides caress each other's arms, backs, and bellies, but holy crap would my panties be soaked by morning. I wanted to have sex with him so badly, and I knew that I probably could if I just asked. But I also knew I shouldn't because I was a virgin and he was the handsomest boy at school and we weren't in a serious relationship and blah blah blah. It was bad. It was naughty.

But God-damn if it wasn't hot.

(As an aside, does anyone have any recommendations for a good beginner's anal plug? I can take one finger easily now, but the jump in width between one and two is proving a little difficult; I think something more tapered (like a plug) would be helpful.)

Anal

Master has decided that I'm to undergo anal training. Currently, though I enjoy anal play a lot, I can only take one finger - maybe two. We're going to slowly work my way up until I can actually take in his cock. (Off-topic: lol dickbutt)

Training, of course, involves practice, which I have to do on my own. So I got a bit o' lube and tried it myself for the first time the other day. It was... interesting. I didn't know the inside of my butt was so soft - like a smaller, less-lubricated vagina, kind of.

Then, last night we got to play for the first time. I think it's because we're "out of practice," but I was very sensitive. I couldn't take as much of a beating as I wanted. :( Stupid butt! Anyway, Master played with my bum more, and it felt really nice. Well, that's a bit of an understatement. I still can only take one finger, but it's getting easier for Master to put it in, and I can handle it for a longer period of time. I wonder how long it'll take for me to progress to two, three, and so on...? This is the first really long-term "project" we've undertaken, so I'm curious to see how it plays out.