I have only had anal sex with one person in my life, which is my wife (and we plan to keep it that way). So I thought it would be interesting to hear what others have to say.
In our relationship, the foreplay tends to dominate the sexual experience. Whenever we have sex, I always drive up her arousal to staggering heights by overloading her with a battery of “lighter” orgasms first. When she can’t take it any more, she’s usually on all fours, begging me to fuck her. By then, she is almost gaping open; when I finally penetrate her there is never any discomfort, just a great relief for her; she often moans “how is it SO good?” or something to that effect.
I am extremely fascinated (and turned on by) by the wide range of mechanisms I can use to make my wife have anal orgasms, and I was also surprised by their diverse natures. I thought I would dedicate this thread to those techniques…
The light touch
Generally this is how we will begin, lying in bed facing each other, kissing. Instead of reaching between her legs, I will reach around her buttocks and go directly for the anus. She will lift her leg a little accomodate this. With the palm of my hand, I will pull a little on her buttocks, spreading her just a tiny bit.
Very gently, stroking her sphincter and the area around it with just a finger is then usually enough to make her cum in less than a minute, depending on the level of arousal. (I remember once having to check if she wasn’t secretly stroking her clit, because I first couldn’t believe the ease with which she was climaxing from my touch alone…)
I would describe this as a clit orgasm light; her breathing will turn ragged, and she will convulse slightly while climaxing, sometimes squeezing her buttocks together to push my fingers away if the feeling gets too intense. Unlike a clit orgasm, this typically leaves her only wanting more! With some lube, the extra-light touch can advance to some harder stroking and a little fingering, it depends on the mood.
Anlingus
This has also become a staple of our foreplay. Eating her asshole is probably the best thing I know in the whole world.
There is so much subtlety to this, it should really merit its own thread, but here are the main points… I always start with her on all fours. Broadly speaking, I tend to alternate between shallow licking with the tip of my tongue, and deep, penetrating motions. When I sense an orgasm coming I tend to slow down considerably, “coaxing” it out of her. Sometimes she will start to push back and jiggle her butt up and down, desperate for me to let her cum.
The actual orgasms are similar to that of stroking with fingers, but much, much more intense! She will moan and pant, convulse violently, sometimes collapsing onto the bed, clench her cheeks, or pull away from me. If I can feel it’s a really big one coming, I don’t let up, and will grapple onto her, pushing my entire face into her, and keep licking for king and country while she squirms, riding out the wave. I once got a nosebleed this way, from pushing down way too hard haha.
If I keep this up, she will usually have enough orgams for us both to lose count after a while, with varying intensity. It is not uncommon that she lets out a lot of vaginal flatulence during this, which embarrassed her a little in the beginning, but I just find endearing.
This typically ends by her tossing me the bottle of lube and begging me to fuck her… Sometimes I plug her up instead, then keep going for a bit, licking around the base of the plug, sucking and pulling on it with my mouth, being careful not to snag her delicate skin between my teeth and the base.
Good vibrations
Another foreplay favourite is the vibrating buttplug. On our honeymoon I gave her an app-controlled Satisfyer Power Plug that she absolutely adores! Sometimes I give it to her on all fours, but often I let her wear it while lying on our sides, facing each other. I lock her in a tight embrace, and kiss her while I control the intensity of the vibrations with my smartphone. It usually doesn’t take long until she reaches climax here either. Turning on the “boost” mode just as she does is a great way to really make her squeal…
Unlike the external techniques, she can build up a sort of “vibrator fatigue” after only one or two orgasms. Typically, it always ends with her pleading me to fuck her instead.
The “deep tissue” massage
When talking about anal orgasm, this is probably the one most think of; repeated thrusting inside the anus, achieved using a toy, penis, etc.
By now, I have gotten familiar enough to make my wife cum anally during foreplay by inserting only my middle finger and pushing up on the right spots inside her anal canal. However, this is by far the most difficult technique. It is also the least “sustainable” since we find that fingernails can easily irritatate the sphincter and the walls of the anus. That said, it can be surprisingly effective, and extremely intimate. Locking eyes with me while she lets me finger her asshole to climax is definitely one of her most vulnerable moments.
I find that she feels more comfortable orgasming this way with toys instead, preferrably hard plugs, made from glass or metal. I just apply directed pulses with my hand on the base of the plug, and the effect is more or less the same.
However, as she has often admitted, no toy is as good as the real deal, and when it comes to eliciting this kind of orgasm, nothing compares to good old-fashioned assfucking. Depending on the arousal level leading up to it, and my performance, she will usually cum a couple of times before I do; she once explained that when orgasming without her clitoris, she is almost immediately ready for another after the climax subsides.
This kind of orgasm is more focused, less full-body, but still more intense somehow. She once tried to explain it as “on the verge of painful—but still only pleasurable”. The intensity of it can still surprise her sometimes.
The finisher
Finally, when she feels me reaching my peak, as I ejaculate inside her, she typically finishes herself off one last time by rubbing her clitoris—usually doesn’t take much—until she reaches a final, earth-shattering climax. Then we collapse onto each other, panting, covered in sweat, lube, and whatever else… This usually marks the end (for a while at least), since both her and I need some time to recover our vigor.
The exception to this is when we have done AO-April, where she never really reached such a “conclusive” climax. She described it like her crotch was on fire from the clit denial…
Closing thoughts
Sorry for the really long post, guess I really wanted to share with you all. Had lots of fun typing this up! Would love to hear what your experiences are, both from women and MSW. Cheers!