The Official First Time Anal Sex Thread.

Discussion in 'Sex With a Large Penis' started by jeff black, Dec 11, 2007.

  1. jeff black

    jeff black <img border="0" src="/images/badges/gold_member.gi

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    Well, in another thread, Jason made the comment about how he lost his 'how to have anal sex' post. I figured I would help him out.

    This is something I found on the net a while ago. It's pretty detailed. Good luck folks, please consider safe sex.

    Enjoy,
    Jeff
    PS, it's in two parts.

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    No one every answers this thoroughly, so let's see if I can do something a little different this time. :)

    Contrary to what a lot of people seem to think, anal intercourse (when done correctly) should be pleasurable for both partners. A good top can make it fun even for a virgin bottom, but there are things a prospective bottom can do before being fucked that will make it a lot easier for both of you -- no matter how much experience the top has. (Good subject for a separate memo.)

    This is what a typical, successful session is like:

    We've already been making love for half an hour or so. Hugging, kissing, stroking, undressing, jerking together, sucking, maybe 69ing or even rimming. You may ask if I'm ready to fuck you, or I may ask if you're ready to be fucked, or I may simply move you into position without a word. There are three main positions that are good for fucking, plus a few exotic ones that are cool but don't work quite as well. They all have in common that I need to be able to enter you comfortably, thrust inside you, and jerk you off after I cum but before I pull out. (Some very submissive bottoms don't want the top to make them cum, but usually a good top will jerk off the bottom before he pulls out of him.)

    The easiest position is you on your left side and me behind you -- spoon style. (The reason it's your left side is because I'm right handed and I'm going to want to reach your dick with my hand. If the top if a leftie, this will need to be reversed.) In this position, you'll pull your knees up at a right angle to your body (fetal-style). For some reason, this causes your rectum to be at the right angle for me to thrust comfortably inside you. Otherwise, I can end up hitting the rectal wall, which is painful for both of us. This position has several advantages: it's the least athletic position, so neither of us will get tired out too soon; for the same reason, I can really take my time on the entry, so I'm much less likely to rush it and hurt you; the penetration is the shallowest, so the risk of "hitting bottom" is lower; you can move your legs to control the angle if it is uncomfortable; we can lie together and cuddle for as long as we want afterwards. A drawback is that I can't see your face. Also, as you get more accustomed to being fucked, you'll want me to be deeper inside you. Likewise, this is the position where I am most likely to pop out of you accidentally and have to reinsert. Nonetheless, this is the ideal beginner's position.

    The most submissive position to be fucked in is doggie-style. You get on your hands and knees and I mount you from behind. Lots of bottoms love this position because it is so submissive, and submission is a big part of the pleasure of being fucked. I can easily reach your dick if I want to, and I can rest most of my weight on your hips, so I don't get tired as fast. Your legs may get tired, however. Drawbacks include: it may be hard to enter you if our relative heights don't match up right (some spreading of your legs may be required); we can't sustain the position for long after we both cum.

    The most intimate position is missionary-style. You are on your back with your legs spread. I face you to enter you, possibly resting your legs on my shoulders. This is intimate because I can kiss you while I fuck you. It's also the deepest. And when I jerk you off after I cum, I get to see you shoot. But it's the most athletic as well (for the top). If I take too long to cum, I'll run out of breath and have to stop. If you take too long, my legs may get cramped. Still, this is my favorite position, and I've used it successfully even with virgins.

    The most obvious position -- flat on your stomach -- isn't really very good because the legs are straight out which means the rectum is at the wrong angle. Unless the top has a very short dick, this will be uncomfortable for the bottom. The top-of-the-world position, where the top sits indian-style
    and the bottom faces him and lowers himself onto the top's dick is useful for a very apprehensive bottom because it lets him completely control the pace of entry (although bottoms can also be guilty of wanting to go too fast and then feeling pain). The touble with this position is that the top can't thrust at all, and if the bottom tries to pump himself up and down, it's easy to end up bending the top's cock, which hurts a lot. If the height is right, there's a variation on the missionary position where the top stands at the edge of the bed and holds the bottom's legs up. This can work very well if the geometry works out. Likewise, the bottom can stand and bend over and the top can enter him from behind. Again, this requires just the right match of height between top and bottom or it won't work. Other, stranger, positions (e.g. where the top holds the bottom up in the air) are mostly for pictures. Almost no one can cum that way.

    So I get you into whatever position I want you in and I begin to lube your hole. If we're doing this missionary style, I'll be able to suck you while I lube you. I'm always slow and gentle when opening a guy up like this, and it should feel warm and pleasant as my finger slowly has its way with you. I
    don't mind if this takes a while -- it's very important that you be loosened up before I try to enter you -- and this can be fun in its own right. If you seem to be real tense and not loosening up despite my best efforts, I'll switch to missionary style, where I can lube and suck, and I'll let you know that I'm going to suck you off instead, but that I want to keep fingering you. That'll take the stress off and guarantee that you remember being fingered as a pleasant experience, so maybe next time it'll work better. In no event will I try to fuck you if I can't loosen you up. (But I succeed about 90&#37; of the time -- even with virgins.)

    Once you're relaxed and my finger slides easily in and out, I ask how you feel. Typically, you feel great, and you're ready for the real thing. If not, we'll skip it. A big part of the pleasure of fucking you is that I know you want it too. Conversely, you should steer clear of anyone who you think
    would pressure you into something you don't really want to do.

    If we're having safe sex, we'll be using water soluble lube -- Like Wet or ID -- and I'll pull out a new condom. Before I put it on, I put a drop of lube on the head of my dick. (This increases sensation -- which is very important.) Then I leave a small gap at the end to hold the cum and roll the rest of the condom all the way down. Then I lube it thoroughly from the head all the way down to the bottom. If we're not having safe sex, we're probably using something like Vaseline, and I just lube my naked cock directly. In either event, I press the head against your hole and hold it there. (Note, the only way we'd be having unsafe sex is if we're in a committed relationship; my risk is fairly small [although not zero] but you're literally putting your life in my hands every time we do it like that, so it's unwise to do it with a stranger.)

    Entry -- especially of a virgin -- is a slow and delicate thing. The pressure of my cock against your asshole should be intensely pleasurable, and you moan and urge me on. I'll ask to be sure it feels nice, but this part always does. Then I increase the pressure slightly and coax you repeatedly to relax. As the pressure increases, the pleasure builds up too
    -- up to the point when my penis actually starts to open you up. When I feel it starting to move into you, I immediately back off on the pressure. It needs to slide into you slow and easy. Otherwise, you'll feel that pleasure suddenly turn to a sharp pain -- a pain too intense to tolerate. If that happens, I'll have to pull out of you, and it'll continue to hurt for about 2 to 3 minutes (although it will seem like forever). If I'm so clumsy as to do this, I'll hold you and speak soothingly to you and we'll wait until the spasm is completely over. Curiously, after a spasm like that, it's usually a lot easier to enter you, but it may be hard to get you to let me try again, unless you are a very determined bottom. Again, if you don't want to, we'll just do something else.

    ONTO PART 2

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  2. jeff black

    jeff black <img border="0" src="/images/badges/gold_member.gi

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    But if I'm doing my job right, the pressure and the pleasure go together, and as you try to relax to accommodate me, you feel me slowly sliding into you. There is a sensation of being opened up that is neither pleasure nor pain, although it can be quite intense, and you may want me to pause and let you get used to it (even though it doesn't really hurt). Once the head of my cock slips past the entry to your asshole, the hardest part is over.

    Your anal canal is actually an inch or so long, and you feel the head of my dick as it works its way along it. Again, this is intense and pleasurable, and I'll go very slow and easy. Once the head clears the far end and enters your rectum, I can slide the rest of my dick into you fairly easily, although the sensation of it sliding into you is still strong. This part of
    the entry is intensely stimulating for me too, since your asshole grips my dickhead very strongly.

    Once I'm all the way in you, I check on how you're feeling again. We pause a bit to give you a chance to get used to it, and to relax a bit more. If we're face-to-face, I'll kiss you while we wait. If this is your first time, you'll be powerfully conscious that you're not a virgin now, that a man is fucking you, and you'll find the whole thing almost impossible to believe. The feeling of submission is very strong, and very pleasurable too -- just as the feeling of dominance is for me.

    Then I begin to pump your ass, taking short, deep strokes. You are still quite tight, and if I pull back very far, your anus will squeeze me out. If that happens at this stage, I have to repeat the entry almost as slowly and carefully as the first time. If we both have a good sense of humor about it,
    that's not a big deal. Another reason to start slowly is that the lube takes a little while to distribute itself properly. At first, you feel my dick dragging along your asshole on each stroke, but after a few strokes it slides freely. At that point, I start taking longer, faster strokes.

    I settle into my usual fucking rhythm. It's nice and pleasurable, and I enjoy the feeling of your body against me even as I take my pleasure up your ass. You have a certain feeling of being used, and, depending on our position, my weight against you puts you ever more firmly in your place.
    Most experienced bottoms really love this part and want the top to go on for a while. Newer bottoms may need the top to cum faster, especially if the lube was inadequate, because they may feel a burning after a while (in which case you can relube and try again or stop and do something else). In all cases, if you feel pain or discomfort, TELL ME! I can't read your mind, but if I know something's wrong, odds are good I can figure out a way to fix it. If not, I'll know when to call it off.

    After a while, I decide I'm ready to cum. If I'm wearing a condom, that's not so easy. The trick to making that work is to take shorter, shallower strokes. I can only do this after I've been fucking you for a while, because until your ass is completely relaxed, you'll squeeze me out if I slide back
    too far. But once I've been pumping you for a few minutes, I can slide almost all the way out and back in on each stroke. Because your anus is so much tighter then your rectum (still), it stimulates the head of my dick very strongly. Even though the condom, it makes me cum after a dozen strokes or so. It also increases the stimulation for you enormously and it can even make you cum without me touching you, although that's rare. (I have done this twice as a top and twice back when I was a bottom).

    As I cum, once I'm past the point of no return, I thrust deep into you, taking quick, hard strokes, pumping either your ass or the condom full of sperm. Lots of people claim to be able to feel their partner shoot inside them, but don't expect to. I think this is a matter of active imaginations. After all, you can only barely feel an enema, and that's 100x as much volume. Anyway, when I'm spent, I slide all the way up into you and rest for a bit.

    At this point, I take a bit more lube, apply it to your dick, and start to jerk you off. Cumming with his partner inside him is one of the best parts of being fucked for most bottoms. If you're so submissive that you really don't want me to make you cum, you should tell me before sex so I know, but you probably still want to jerk yourself off before I pull out.


    Once it's all done, I'll pull out of you and we'll go shower together. Contrary to popular belief, I almost never encounter any shit when I do this. This is true even though I may have felt the end of a turd when I lubed you up. It just goes further up inside you and stays there. You may audibly pass gas when I pull out, though, and if you do, I'll just laugh and tell you it's okay. (Lots of bottoms like to using a small enema about an hour or so beforehand. If you do that, use the little bottles from the drugstore [e.g. Fleet enemas] but discard the chemical contents and just use warm tap water.)

    The next time you visit the john, however, you should do it sitting down -- even if you only need to piss. The reason is that when you squeeze to pee, you'll probably squeeze some of the lube out too, and if you're not sitting, it'll run down your leg. You'll also squeeze out some of the air I pumped
    into you, and that'll make some noise, which can be embarrassing. To avoid that, take some toilet paper, make a pad, press it against your hole, and THEN squeeze to pee. That'll muffle the noise and collect the lube at the same time.

    As with anything else, practice makes perfect. If we do this often, the entry will be second nature. I'll know just how hard to push, you'll be expert at relaxing, and I'll be able to enter you in under a minute. Done right, this doesn't cause you any harm, and it won't wear out your asshole or cause you hemorrhoids or anything like that -- even if we do it daily.
     
  3. jeff black

    jeff black <img border="0" src="/images/badges/gold_member.gi

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    There you go, folks. I didn't write it, but it sounds pretty darned helpful.:smile:
     
  4. matt121matt121

    Gold Member

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    Awesome description of a Virgin Anal Sex experience, and so true, its suppose to be pleasurable and not painful, I hate when I've heard that tops aren't happy if it doesn't hurt there bottoms. I'm glad that now 99% of the time, after my first two or three times that there isn't any blood after I get fucked, that was the most scary part of loosing my anal virginity was afterwards when I went to the bathroom and found blood.
     
  5. torychristoph

    torychristoph New Member

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    i always wonderd, hows shit dick caused hahaha
     
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