A Guide to Great Anal Sex

Celeste and I called this series "A Guide to Great Anal Sex" and not "A Guide to Great Anal Intercourse" for a reason. It's because so much of great anal sex doesn't involve intercourse itself.

We think that, with a few exceptions, one of us should be focused on giving pleasure to the other, that there should be a giver and receiver. Trying to be both at the same time confuses things. This is a section on outercourse for me, just as we did one for Celeste. My orgasms turn her on a much as hers do me, particularly when she can see or taste them.

(Celeste: I think it's because his body can make me feels so good that I just love everything about Jimmy's crotch. Maybe it's a fetish, but just thinking about it makes me damp. When I bury my face in it, I love that mansex smell. I love to roll his big, soft nuts around in my mouth, making him twitch. I love his dick and even have a photo I took of it with a drop of precum dangling from its tip hidden in my desk at the office in case I need a pick-me-up during the day. I love his asshole and running my tongue around its rim. I love running my tongue through his pubic hair, licking his treasure trail up to his belly button, and sucking his cum out of his inny where it pools when he cums. I love licking the cum off his body after he shoots. I love the warmth and the force with which he cums in my mouth and ass. The taste is okay, but not my favorite. It's a little salty and reminds me of the smell of salt air and seaweed when you're at the beach. His precum, however, is just delicious. It's so sweet; just like liquid sugar.)

Celeste would tell you that I have four orgasmic triggers in my body and two are located in my ass. When she stimulates any two of these, I'm almost sure to cum. Make it three at the same time and she is liable to get a "gusher." The four are my 1) sphincter furrow, 2) prostate, 3) frenulum, and 4) nipples, especially their tips.

We've talked about the sphincters before. When we're rimming, Celeste and I both aim for the furrow between the inner and outer ones with our tongues. The pleasure is so intense that rimming is probably our favorite sex act.

The prostate is a small, nut-shaped gland that secretes a component of semen. It's located in almost exactly the same spot on a man's body as the g-spot is on a woman's, although the woman's is on the outer wall of the vagina and the man's on the outer wall of his anal canal. (It is interesting that two of the most intense pleasure centers on a both a man and woman's body are hidden inside and most easily gotten to through our asses.)

Some guys may find having his partner inserting her finger in his butt beyond his comfort zone and won't want her to do this. I, however, love having Celeste's finger (lubricated and with a trimmed nail—sorry about that ladies, but the same rules apply to you as they do to guys. Sharp nails are lethal weapons in the ass.) pressed against my prostate. Just as Celeste can decide how much pressure she want the head of my penis to apply to her g-spot, I can decide how hard I want to fuck myself on her finger.

The frenulum. You may not know the name, but you'll recognize what this is: the fold of skin on the underside of your penis that seems to connect it to the shaft. There are no nerve endings in the shaft of a guy's penis and very few in the head; they're almost all located in the frenulum. When you masturbate or when your partner gives you a blowjob, it's the stimulation of this fold that provokes your orgasm. If you doubt this, take your frenulum between your thumb and forefinger and rub. For me, the sensation is immediate, too intense and not particularly pleasurable. On the other hand, nibbling, gently licking, or softly stroking it are wonderful. Many sex experts will tell you that all orgasms for women involve the stimulation of the clitoris. You could almost say the same for men and the frenulum. I can cum without it being touched, but it's not easy.

My nipples. Unlike Celeste, who thinks her nipples are a distraction from her pleasure, I really get off on nipple play. I don't know enough about our nervous systems to explain the wiring involved, but for me it's just like toe sucking is for Celeste. When she licks my nipples sucks them, takes one between her teeth and shakes her head, or flicks them with her finger tips, it sends jolts of pure pleasure directly to the head of my penis.

There are many possible combinations from these four triggers although only three can be used simultaneously. Obviously, Celeste can't rim me and massage my prostate at the same time, so that an either or situation. Beyond that, the intensity of the orgasm I want determines whether I ask Celeste to touch one, two, or three triggers. It's like ordering off a menu of pleasure with endless possibilities. Here are a couple of my favorites.

Celeste must give one of the best blowjobs in the world. She holds my dick and cups my balls while she nibbles my frenulum, teasing it with her tongue. When I get rock hard and my precum starts to flow, she takes its head into her mouth and runs her tongue over it and along my frenulum. I have a wonderful cum in her mouth that she usually swallows. I'm tempted to say nothing could be better than that, but that's not true if I want a more intense orgasm. If I finger my nipples while Celeste has me in her mouth, the intensity probably doubles. If I finger my nipples and Celeste also sticks her finger up my ass and I fuck myself on it during the blowjob, the intensity is off the charts. (Sometimes, Celeste doesn't swallow my cum but brings it up and drips it into my mouth. We snowball with it, passing it back and forth until it's a frothy mass. I spread part of this on my dick and the rest on her hole. We frot and Celeste strokes herself to an orgasm. We both end up having orgasms with the taste of my cum in our mouths.)

We've talked about rimming and how sensual it is. However, rimming by itself doesn't let me orgasm. If I assume to doggy style position, Celeste can rim me and stroke my frenulum at the same time. This leads to a great cum. If I lie on my back and throw my legs over Celeste's shoulders, I can stroke my nipples while Celeste rims me and plays with my frenulum. The result is an even more intense orgasm.

There are many combinations that work well, but you can see from these two examples how the stimulation of one, two, or three triggers affect the intensity of my orgasm.

There is one other orgasm that Celeste taught me about that I want to mention. Even though it doesn't have anything to do directly with my ass, it is unique. This is when she slowly flicks the tips of my nipples with her fingers, and that's all she does. This just drives me crazy because every time I approach my p.o.i., she stops, waits until I have relaxed, and then starts slowly flicking again. The rule is that I'm not allowed to touch myself while this is going on. In fact, I lie with my hands under my butt cheeks so I won't. My whole body shakes during this and sometimes tears roll out of my eyes, not because I'm sad but because my entire nervous system is so aroused. Finally, after ten or twelve minutes of this torture, Celeste takes me through my p.o.i. by not stopping her flicking and an amazing thing happens. I have this feeling that I have to pee in the worst possible way and I cum, but it isn't an ejaculation, at least it doesn't look or feel like one. The only way I can describe what happens is to say that I pee cum. A steady stream of it just flows out of my dick for ten or even fifteen seconds and I feel incredible relief, like the feeling you experience when you finally take the piss that was going to burst your bladder. My whole body convulses three, four or five times after this and all I want to do is turn over and go to sleep, which is what I usually do.

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(The section on sequential orgasms doesn't really fit with this. We think it's important, so we're going to post it as a short, sixth part. Part seven will then be games, rules, and Celeste's goodbye.)