Anal Orgasms

In the previous three days, I'd been watching porn and generally thinking a lot about sex, but hadn't masturbated. As you can imagine, I was feeling pretty horny. Almost anything would make my cock drip precum. Anything. I didn't have to be hard or even start to get hard. Some random thought would just cross my mind, and then I'd suddenly be aware that my panties had a wet spot on them.

I almost never wear male underwear. That is one way in which my feminine side manifests itself. A lot of the clothes I wear are female clothes, as well, though you'd not necessarily know it by looking at me. I'm "stealth" when I'm out of the house. But most of my jeans are women's jeans. I have a lot of women's shirts, and some sweaters. I even have a couple pairs of shoes that look 'European', but are really women's shoes. So there are times I can actually go to work wearing nothing but women's clothes, though no-one is the wiser. And even if I'm wearing a men's shirt, in the cooler months, I'll often be wearing a camisole, or a women's tank top, underneath it. And I frequently wear lipstick, of a shade carefully chosen to match my natural lip color, and sometimes a clear mascara.

When I'm at home, I can be more myself, and I will often dress in more obviously feminine ways. When my wife is away, especially, I'll take the opportunity to wear whatever I want, without having to worry about what anyone else might think. She's incredibly supportive of my gender struggles, but she sometimes thinks I just look kind of silly in women's clothing. I understand her point of view and even agree with it, to some extent. It's not so much how I look but how I feel that matters to me. So I try not to push it with her, but let myself explore my feelings more freely when she's out of town.

I'd been dressed this particular day in a long gray skirt and a light, cable knit cotton sweater, also in gray. Underneath, I was wearing black pantyhose over purple panties, and a purple camisole under the sweater. I love purple! My shoes were simple black flats, from Payless (which, by the way, carries a good selection of inexpensive women's shoes up to size 13). For jewelry, I had put on a pair of small diamond in-out hoops, which are one of my wife's "go to" pairs of earrings. And I made myself up: Combination foundation and powder, mascara, eye shadow, blush, and lipstick. To complete the look, I put on a pair of size 6 foam breast forms from Transform. Just looking at my body, I thought I looked pretty good. My face still looked like that of a guy wearing makeup, but, as I said, it's how I feel, not how I look, that matters. And I felt great.

By the time I went to bed that night, I was feeling very comfortable, and I was very ready to make love to myself. I wasn't sure what I was going to do, as I was pretty tired, so I decided to take it slow. I put on a while satin camisole and refreshed my lipstick, but otherwise got naked. I started with a fairly thin butt-plug I bought many years ago. It has three "bloops" which are not round but square in shape. It is made from a very pretty red and black silicone. It's about four inches long, and the largest of the bloops is less than an inch in diameter, so it's very easy to insert and wear.

So I put it in and decided to just lie there and fantasize. I've been fantasizing a lot lately about having my wife spank me. We'd done it once, but not since. So I lay there and imagined the conversation we might have if she were to decide she were willing to do it again. I often find myself fantasizing not about an actual act, but about the prelude to that act. For example, instead of thinking about fucking some imaginary lover in the ass, I'll think about our conversation beforehand. About what she says to me, and what I say to her, and I'll find myself intensely focused on the crucial moment, as my cock is poised at the entrance to her lovely butt and starts, ever so slowly, to slip inside her. I never get past that moment, but replay it over and over. And so tonight, I think about my wife as she talks about spanking me, and we talk about the details of what we will do.

That fantasy got me very aroused very quickly, and I could feel my ass starting to quiver on the little invader within. I was ready now for something else. I'd brought to bed with me the Peridise devices made by Aneros. These are thin, hard plastic probes that are about 3½ inches long, with a small bulb on the business end, a much smaller bloop right below it, one more little bloop on the other end, and a small handle to keep it from getting lost. It doesn't sound like much, but it is magic once you figure out how to use it.

When we orgasm, one thing that happens is that the muscles in our pelvic regions contract in various ways, and those contractions are one of the things that feels so damn good. What the Peridise does is set off some of those contractions, particularly a series of "peristaltic" contractions in the muscles surrounding the rectum. These are the contractions that cause the familiar "winking" of the anus during orgasm. So if you can set those muscles to doing their thing, you get a lot of the feel of a full-blown orgasm. Or, to put it differently, you get to focus very intently on one group of the feelings you have during a more traditional orgasm. Note that this does not involve the prostate, so it can work no matter which kind of body you have. But a particular advantage for people with penises is that this sort of "peristaltic" orgasm doesn't involve ejaculation, so there is no refractory period, so you can have as many of these orgasms as you like, and you can still shoot some jizz later.

I lay back and started with the larger of the little probes. I got just the initial bulb into myself and then pulled it in deeper by grabbing it with my PC muscles. I never can get it all the way in like that, so I pushed it in the last inch or so. I then relaxed, resumed thinking about my wife, and started doing Kegels on the probe within me, just enjoying how smooth and firm it was, marveling at how much I could feel it.

I then got down to business. The method here is the "clenching" method that is used with many prostate toys. The idea is to contract the rectal muscles on the toy, squeezing it, but not all the way. Just half way or so. You can't actually hold it just that way, so the muscles twitch back and forth. With prostate massagers, this causes the device to move within the rectum and, in particular, to dance back and forth over the prostate. With the Peridise, it causes the rectal muscles to grab onto the little balls on the probe and try to pull it, or push it, or something, through the anal canal. It thus moves back and forth a bit, pleasurably massaging the sensitive tissues just inside the rectum. But since the probe is held in place by the last bloop, which sits almost right between the two sphincter muscles, it can't really move that much. So it seems like the rectal muscles get kind of frustrated, and they go into peristaltic motion.

You can feel this as it starts to happen, feel the muscles start to clench and release on their own. It's like going up a little hill, then down again, then up a slightly bigger one, and down again, until you go up a really big hill, and then, suddenly, contraction follows contraction and you are swept up by waves of sensual pleasure that seem as if they might never end. And, amazingly, they do not end, not nearly as soon as one might think they would. I had an orgasm recently that lasted, I will guess, nearly a minute, and it only ended when one of my cats jumped on the bed and broke my concentration.

I enjoyed three or four orgasms this way, imagining my wife beside me, reading. I imagined her being ignorant, at first, of what I was doing, and then realizing, as a soft moan escaped my lips, that I wasn't just lying there, and asking me what I was doing. I answered, quietly, "cumming". And then she leaned over and kissed me gently, looking into my eyes, and reached around to hold me as I rode it out. It was a great fantasy.

I was ready for some prostate play. I got out my NJoy Pure Wand. I have written about this little miracle before, so I won't go into that part of my evening in any detail. I decided I wanted to have a couple prostate orgasms before I tried to draw out some prostatic fluid, so I did. I inserted the smaller ball, thinking I'd give my ass a rest, and moved it back and forth over the part of my prostate closest to my anus. That brought me to orgasm quite quickly, and then I had a couple more orgasms the same way. By then, I was ready to taste myself, so I inserted the Wand deeper, pressed it up against the very back of my prostate, and slowly pulled it out. Nothing. So back in, and back out, and finally a little drop of prostatic fluid emerged, which I scooped up with my finger and inserted into my hungry mouth, holding it on my tongue and savoring its sexy, earthy sweetness. I kept that up for some time, extracting maybe ten little drops of fluid, though I was a bit disappointed there didn't seem to be more. But there wasn't, and there was nothing to do about it. As a consolation, I gave myself a couple more prostate orgasms.

By now, I was thinking maybe I was ready to ejaculate and be finished. But earlier that night, I'd watched the movie Hotel, directed by Jincey Lumpkin for her studio Juicy Pink Box. The movie features what is, by all accounts, extremely realistic lesbian sex, and I'd found it very arousing indeed. One of the interesting features of the movie is that two of the four couples practice safer sex, using rubber gloves when penetrating one another. I'd occasionally used a (non-latex) glove myself when engaged in anal play, mostly for cleanliness, and decided I'd do so tonight, as well, imagining that one of the beautiful women on the screen was massaging and penetrating my anus. Another nice thing about using a glove is that lube seems to last much longer, and the glove is smoother than just my skin.

So I put a glove on my left hand, lubed myself up, and softly massaged my anus. I put a finger inside myself and firmly massaged those wonderfully sensitive tissues just inside me. But as nice as that felt, it wasn't that comfortable. It is annoyingly difficult to get my fingers properly inside me, to reach deep enough, and still to have some freedom of movement. So I tried several positions. On my side. On my back with one leg pulled up. On my back with my legs spread. On my back with my knees tucked against my chest. I ended up, this night, thinking that the best position was on my back, with with my hips rolled over to the right, my left leg over my right, and then reaching around behind myself.

My intention had been to massage my anus, luxuriate in those sensations, and then rub my cock for my last orgasm of the evening. But, for some reason, I suddenly wanted very badly to be filled. Two and then three fingers went into me, and then a fourth, as my ass begged to be opened. I pressed my hand in as far as it would go, almost to the last knuckles, spreading my anus wide and then, briefly, inserting my thumb as well (though that had almost no additional effect). I kept at that for some time, pulling my hand out and then putting it back in, just a couple fingers at first and then building back up to four. It felt wondrously decadent, and I wondered what I must look like. I started to fuck myself hard with my hand, as hard as I was able to in this unnatural position.

I needed to be fucked. That was the obvious lesson of what had just happened. And I needed really to be filled. So I went and got the biggest dildo that we have. It's got six inches of useful length, and starts out at over an inch and a quarter, growing to an inch and three quarters, which is big for me. I put a condom on it, as I've learned now that the dildo itself isn't terribly smooth, and has a strange tendency to stick to the skin, even with lube. So, with the dildo sheathed, I lay back, spread my legs, and started pressing it into me. It went in pretty easily, but it took a few tries, back and forth, before my anus relaxed enough for me to get it all the way in. Now I felt full, very full, and I just lay there for a bit and enjoyed it. But I still needed to be fucked. I can only really fuck myself with the first few inches of this one, so I pulled it out and started the process. Mmm, was it good. But I really wasn't getting what I wanted from it. It's just too big. So I pressed it deep back into me and enjoyed that feeling again before pulling it out and setting it aside.

I grabbed the smaller black dildo I used the last time I did this kind of thing. It's about seven inches long and about an inch and a quarter around, so very comfortable. As open as I now was, it was going to slide in and out of me very easily. I put a condom on it, too, slathered my anus with lube, rolled my hips up, pulled my legs wide apart, and thrust the fake cock hard into my ass. Oh! Now that's what I needed. "Fuck me!" I screamed, and that's exactly what my imaginary lover started to do, hard and fast. The sensation was so intense that I couldn't maintain the position I was in and also manage to move my arms. So I rolled over onto my side and let myself have it that way for a while.

I was now crazy with lust and arousal. I got up onto my hands and knees, lying my head on the bed. I find this position probably the easiest. It's pretty stable, not requiring much effort from me to hold it, and I can reach around behind myself for access to my ass. I lubed myself up a bit more and plunged the black dildo back into my butt. I gave myself a good, solid fucking with it. Unusually, I was now very hard. I very often don't have erections when I'm receiving anal sex. But I did now, and I suddenly had what turned out to be a very good idea.

Thinking ahead, I put a paper towel on the bed underneath me. If I rested my weight mostly on my head, then I could get one arm free. I'd been using my right (stronger) arm to fuck myself, but I now reached around with my left arm to grab the dildo, leaving my right hand free for other purposes. There was too much happening for me really to fuck myself with my left arm, so mostly I was just holding the dildo inside me, though I was able to move it around a bit. I started to rub my dick furiously with my right hand. I was hard, and I was wet with precum and lube. I spit into my hand for moisture, as some of the lube had started to dry, then went at my cock with abandon. I was moaning loudly, occasionally screaming with pleasure, grunting the odd "Yes, fuck me!" from time to time. I don't know what else. I was lost in that moment, consumed with what was happening in and to my body. An orgasm took me suddenly, without warning, my hips jerking towards the bed, and stream after stream of beautiful cum landed, mostly, on the paper towel.

I rolled over onto my side, breathing heavily, my body quivering with the aftershocks of a truly earth-shattering orgasm. Regaining my senses, I removed the dildo from my ass and set it down, on another paper towel, along with the other toys I'd been using, and rested a bit more, the heady smell of freshly ejaculated semen slowly filling the room.