For years, I swore I’d never have anal sex. I believed that it would have to hurt, and that it couldn’t possibly be pleasurable for the receiver. I saw it as degrading and icky and altogether something I wanted no part in. Then, this year, I started reading sex toy reviews and sex blogs. I found that anal play could be painless and enjoyable. But I still didn’t think I’d want any part of it. K was curious about anal sex, but he never pushed or even asked me to do it; he just let me know he was curious about it, and that was it.
Soon after I started reviewing sex toys, I discovered that I’m submissive in relation to K. One night, while we were playing, he threatened to fuck me in the ass if I wasn’t good. The threat frightened me, though I knew it had no teeth. He wouldn’t do something to me I wasn’t ready for. But I realized something else: I wanted the threat to have teeth.
When I told K I wanted to work up to anal sex, he nearly fell over in shock. In less than a year, his woman has gone from no sex drive to insatiable sex drive to masochistic submissive “slave” to wanting anal sex. He was totally down with it, of course. We did plenty of research online: GoodVibes’ guide to anal sex and Tristan Taormino’s site were particularly helpful. Soon, with the help of plenty of Maximus lube, K had his finger in my butt.
Having something up my butt was a very odd feeling. Slightly uncomfortable, though not painful at all. Gradually, my muscles loosened, and I was able to encourage him to move around more. As soon as K’s finger entered my rear, I went full-on submissive, though we had planned this experiment as a rare vanilla encounter, since I was still nervous about it. So I don’t know if it started to feel good. The submissive state it threw me into, plus the weirdness of having something in my butt, drowned out any physical sensations.
After K had put his finger in my butt a couple times, he put a finger in my vagina at the same time as in my butt. The orgasm was huge; I heard myself making some pretty weird sounds. Soon, I told K I thought I was ready to work up to having a slim dildo in my butt. I expected to be able to take just a bit more than the head. However, the head felt so good, K was able to ease the whole thing into me. Its smoothness felt much better than a rough finger while he moved it inside me; when he commanded me to come, I pretty much came forever. A couple nights later, he fucked me vaginally with the dildo still in my butt. I had never felt so full.
The next visitor to my posterior was a butt plug. It was shorter than the dildo, but wider, and therefore actually a little more difficult to take. With a little work, K popped it in me, after he’d spanked me thoroughly. As he took me from behind, the plug moved in my ass in time to his thrusts. Dually penetrated by him, I felt completely owned. After I orgasmed, I reached that submissive place that is beyond orgasms. It’s not quite the floating detachment of subspace. You know how you feel immediately after you have a huge orgasm? Imagine that, drawn out endlessly. Then add sexual desire and a feeling of being used, and your purpose being fulfilled by this particular person using you. Nirvana.
When K had come in me, he told me to fuck myself in the ass with the plug. I could barely move it. He told me to take it out, we’d try the dildo instead, that would be easier. I grasped the plug’s base and pulled, but couldn’t remove it. I told him I couldn’t get it out, which he found most interesting. I can’t physically get anything into my butt, and once something is there, I can’t get it out. Only K can put things in, and only he can remove them. This means he owns my ass even more than he owns the rest of me. Need I mention how much weight this adds to his domination of me?
A couple days later, we were ready to try the full monty: his dick in my ass. Ready, willing, and unable. I wasn’t warmed up enough, K applied too much lube, we couldn’t find the right position. We tried for quite a while, but failed miserably. K just couldn’t get it in. As I told a friend, we were apparently too dumb for buttsex.
We were determined to try again after our pride had recovered. Well, after K’s pride had recovered; we both very much enjoy my humiliation. I didn’t know when it would be, but I was ready any time. Yesterday, he put the butt plug in me and made me keep it in for a while. I did laundry, I served dinner — all very slowly. The plug brushed against my G-spot as I moved and sat, and the constant reminder of K’s dominance inside me made everything muzzy. I moved slow, I thought slow. The plug was sometimes uncomfortable, but never painful. And it made me want him to fuck me, desperately. It was constantly arousing; a kind of sexual torture, for about an hour.
After dinner, K took me to the bedroom and told me to take off my clothes. He removed the butt plug and applied more lubricant to me. I had an odd feeling of being stretched, of having a much larger opening than usual. As with our first foray into anal play, we hadn’t planned on our first full anal sex venture being a d/s experience. But as he attempted different positions to get into my ass, “sir” and “master” tripped out of my mouth on their own. He told me to lie flat on my stomach, and penetrated me with the tip of his penis. It felt just slightly uncomfortable, but at the same time, better than anything else in my butt ever had. I desperately wanted him to get in farther, but in that position, he couldn’t.
I was using a vibrator on my clit to help with arousal and relaxation. We tried different positions, failing at each one, and the vibe got misplaced somewhere along the way. Finally, we found a position that worked. K slid into my ass smoothly, about halfway at first. He asked me if I wanted him to go farther, and I told him yes. (“Please yes, sir,” to be precise.) I begged him to be gentle at first, and he was. There was some discomfort as he took my anal virginity, but I didn’t care.
People usually think submission is passive. Submissives often think of ourselves as passive too; we are the ones being beaten, fucked, tied up, ordered around. A submissive is the object of the sentence, not the subject. But having K’s dick in my ass threw me into a frenzy of submission. This was not passive acceptance of what was happening to me. I was being used by K in a way I had thought for most of my life was degrading and shameful, and it fulfilled me utterly. It also felt pretty damn good. His dick was smoother than a butt plug or dildo, softer on the outside, but much harder. I was surprised at how similar it felt to vaginal sex.
I wasn’t about to orgasm just from anal sex, though. It feels good, it arouses me like crazy, but unlike vaginal sex it does not, by itself, make me come. K ordered me to use the vibe on my clit again while he fucked me, but we couldn’t see it, and we weren’t about to get out of position and have to fumble into it again to look for it. So he commanded me to use my hand on myself until I came — a command I’ve always found more humiliating than to use a toy, for some reason. Of course I did it.
I let K know he could fuck me harder without hurting me. I was surprised that now, I felt no discomfort at all. Even when they feel great, fingers and toys always cause me some level of discomfort in my ass. K’s dick is much bigger than anything else that had been in my butt, and I expected it to be more uncomfortable, but it felt purely good.
I came, and he came. I didn’t feel sore at all. He said it had hurt him a little, because my ass was so tight. I had believed nearly all my life that anal sex hurt for the receiver and was only for the pleasure of the penetrator. One more myth blasted.
Neither of us likes anal sex as much as we do vaginal sex, physically. It’s fun to have in our repertoire though. Best of all, it makes me feel owned, totally submissive, completely used. It makes K feel powerful, dominant, strong. He can now fuck me without giving me an orgasm, something we found impossible before. And now, when he threatens to fuck me in the ass, I’ll know he means it.
I am so inspired by how easily you were able to get into teh buttsex. You have the added benefit of the d/s element of it, which sounds totally awesome. I will be interested in if you can ever have an elusive anal orgasm.
So cool. I guess it proves how true that we should never say never.
I’m glad you had fun, the only time I had tried with a partner, it was way before I knew anything about anal sex, and things were not fun. He penetrated me before any warming up or lube. Yeah, it was painful. I think he just watched too much porn… If he had only knew what he was doing, he’d have discovered I like it. 
I always said I would never never have anal sex. I tried it a couple times, it hurt, I hated it, and that was one of my hard limits. After I was anally raped, I decided I had to reclaim that for myself and I had a very similar experience with adjusting to anal. I found that when I did it the “right” way, I really liked it.
I’ve only had 2 partners that like anal.. I’ve had a couple of others that tolerated it..One lady would only let me have anal with her after she used a strap on on me.. Found out I liked it.. But so far it has only beeen with her and we don’t see each other since3 I got married..
My wife of 35 years and I have had anal sex regularly as part of our sex life and before and during our marriage we have both had anal sex with others as well. So, if I can, I’d like to offer a couple of tips that I didn’t see in the two guides to anal sex that you linked to:
1.) clitoral stimulation, whether with fingers or a vibrator, etc., is very important, especially for the beginner, because it adds a level of pleasure and excitement before entry, it helps to distract from any discomfort once penetration begins, and, most importantly, it helps to create a link between the sensations of pleasure and anal sex in the brain (particularly if orgasm is achieved while having anal sex)–if the brain begins to perceive that having anal sex is exciting, pleasureable and can lead to orgasm, some women are able to reach a point, after a number of repetitions over time, where they can feel intense pleasure and even orgasm while having anal sex without clitoral stimulation (although, perhaps not every time, in which case, clitoral stimulation can then make the act easier and more pleasureable; and
2.) it sometimes also helps to “bear down” and push out, as if passing gas or having a bowel movement, as the man’s penis is entering the anus and then sliding up inside–pushing down with the inner muscles puts pressure on the lower part of the rectum to expand at precisely the time when pressure from the penis is trying to force that part of the rectum to expand to accomodate it and, as those muscles release the pressure, not only are the pulling back and allowing the upper part of the rectum to open up, but having just been tensed, they have been fatigued and now have less strength to resist or push back against the penis as it moves further into the rectum–in some cases, at times, this can this action of pushing out and then letting go and relaxing can create almost a sucking effect where the muscles almost seem to pull the penis deeper inside (it varies from woman to woman and doesn’t happen every time, but it usually makes entry at least a bit easier).
The amount and type of preparation needed for a woman to enjoy anal sex not only varies from woman to woman, but is greatly impacted by experience, setting and the mood/attitude/purpose one has for having anal sex at that time. Just as vaginal sex was, in general, not as good the first few times, you can’t expect anal sex to be great the first time or few times you have it either: your body has to adjust to it (and it will if you keep doing it) and you have to learn and become proficient at doing what works and makes it most enjoyable for you, even as your body adjusts to it.
How you feel about doing it and what you want/expect to get out of it will greatly impact the pleasure that you get from having anal sex. If you don’t really want to do it, feel that it’s dirty, are just doing it because your lover wants it, and you expect it to hurt in a way that you don’t want, you’re not going to enjoy it or do it often enough to give yourself or your body a chance to enjoy it. Receiving anal sex is different than having vaginal sex, not only physically, but also in emotional and psychological terms: in many ways it is the ultimate surrender of one’s body, allowing one’s partner to penetrate to the deepest, most intimate core of one’s being, and, it can be felt to be an act of submission and humiliation. If you are unwilling, afraid or unable to allow yourself to be that open and intimate with your partner, you are not going to be emotionally primed to enjoy anal sex and will perceive the act as painful, unpleasant, degrading, humiliating or, at best, with ambivalence and you’re not going to be too keen on repeating the experience. In this, who your partner is and the circumstances (when, where, mood, etc.) in which you attempt to have anal sex matter a lot and you will require the maximum amount of preliminary preparation and stimulation just to get through doing it. If you are excited by the prospect of allowing your lover to be so intimate with you and are open to surrendering yourself completely to him, your perception of the sensations and the entire experience are going to be very different and your need for preparation and preliminary stimulation will be lessened at least somewhat.
If you like to feel dominated, submissive or enjoy feeling humiliated to some extent–something that a lot of women are afraid to admit to themselves, let alone share with their partners initially, it is a lot easier to enjoy anal sex–although both body and mind still need time to adjust to engaging in the act. In this case, associating anal sex with being possessed, taken, forced to submit, or humiliated by receiving anal sex from your partner can have a huge psychological effect on how you will perceive and how much you will be able to enjoy the act. And, this will also have an impact on how much preparation and preliminary stimulation you will require. The discomfort or even pain that a woman–even one who engages in anal sex regularly–can experience not just initially, but from time to time (there are times when, for any number of reason, you or your body just may not be physically or mentally “up” for having anal sex, it happens), can actually serve to increase and satisfy the desire to be possessed or humiliated, etc., making the experience, if not necessarily the act itself, very enjoyable. In this case, you may not want or need to spend as much time preparing for penetration and may not want or need much additional stimulation (although I would recommend that beginners still find a way to incorporate clitoral stimulation into both preparation for the act and during the act itself).
There have been times over the years when I have spent well over an hour preparing a woman to have anal sex with a tongue bath, eyelash stimulation, oral and manual clitoral stimulation, a vibrator, rimming, and plenty of lubrication before attempting anal sex with her. There have been other times when I have had women beg me to have anal sex with them with only their vaginal juices as lubrication and no preliminary preparation whatsoever. While some of these women were the same, they were at different stages of experience and in different circumstances (the relationship had become more intimate, the setting was different, their desires and expectations had changed, etc.) when they required the former preparation for anal sex than they were when they needed the latter. Not all women, not all women’s bodies, not all levels of experience and types of needs and desires are the same. Not only that, but it’s important to understand that these things evolve over time as well.
So, don’t give up on anal sex right away just because it didn’t work or wasn’t what you expected or as enjoyable as vaginal sex the first or first couple of times you try it. If you are trying to analyze what you are feeling while you are trying to do it, it’s not going to be as enjoyable for you as it would be if you have a sense of what you want to get out of it and focus on trying to get that out of the experience, knowing that both your mind and your body need time and repetitions to make the adjustments that are needed to give you what you want to get out of receiving anal sex from your partner or lover.
I hope this will be of some help and encourage you to continue to explore anal sex in the future.
Tristan does talk about clitoral stimulation quite a bit, but thanks for highlighting it
.
I don’t think #2 would work for me — I would just end up pushing K out. If it works for others though, great!
Using only vaginal juices as lube during anal sex isn’t something I can endorse. I realize some people like to use very little or even no lubrication during anal sex, but I will never recommend it. You can really harm yourself that way. Also, when anal sex hurts, there is real potential for serious harm. I know how tempting pain can be to we masochists, especially sexual pain, but the enjoyment of anal pain isn’t worth the possibility of never being able to have anal sex again because you damaged yourself.
Many men really love being anally penetrated too. Plus they have prostates to play with in the rear. I’m very much in favor of everyone who is at all curious trying anal penetration — and stopping right away if they dislike it.
So as tempted as I was to reply to you with “tl;dr,” I in fact did read your ridiculously overwrought comment and now have only one thing to ask: DID YOU EVEN READ THIS BLOG POST? You come across as extremely high and mighty, especially about making anal sex good, which I’m pretty sure Elodie details in this post. Why does she need random-dude-on-the-internet’s guide to anal sex when she seems to be doing fine so far? Oh right, because you want to feel superior.
Congrats!! Sounds very much like my (eventual) successful anal story. Mucho jealous that you had all those lovely props your first few times.
It is amazing what our bodies can accomplish once coerced (especially in a D/s setting).
I feel, after the last two comments, that I need to clarify something.
There wasn’t any coercion involved here, even play coercion. My body was totally relaxed, calm and receptive. While anal sex throws me into a very submissive state, that’s only because I am submissive. There’s nothing inherently d/s or degrading about anal sex itself — it’s just a psychological thing that some people can enjoy playing with. Also, even though I was being submissive, I was still letting K know every step of the way what felt good and what felt not so good. I told him “not that far, please”, “okay, go further now”, “that’s enough lube”, “I’m ready”, “not so hard”, “as hard as you want”, etc. — I just automatically added “sir” to it. You could as readily append “slave” to it instead, or nothing.
Gnostic, I’m somewhat puzzled by your comment. (And not just the bits about eyelash stimulation…) Some of the things you say seem oddly generic. Looking at comments like, “If you like to feel dominated, submissive or enjoy feeling humiliated to some extent–something that a lot of women are afraid to admit to themselves, let alone share with their partners initially,” I’m not sure how much of this blog you’ve read–and some, like your conclusion, make me wonder how much of the entry you’re commenting on you’ve read. And some of them just seem off–there shouldn’t be pain during anal sex.
Wow, this was best story for first butt sex I ever read