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Dramatic asks,

I was wondering, when I guy has sex the first time and he's on the bottom, how much would it hurt when the other man enters him? Would it tear skin, cause bleeding at all? Who would get the orgasm first, the one on top or bottom? I suppose top, but...


Dear Dramatic,

The pain a guy feels the first time he bottoms depends on a bunch of factors. How comfortable is he with the idea of getting fucked? How comfortable is he with the other guy? How scared is he? How horny? How drunk? All these, and more, will have a profound effect on how much pain he feels - if any.

If he's comfortable, and turned on, and relaxed, he may feel no pain at all. If he's tense, or nervous, or conflicted about the act, he may feel too much pain to complete the act.

It's not like a woman's first time - where the hymen gets broken. There is no *physical* reason why a guy can't enjoy his first experience of anal sex - it's mostly psychological. The more tense a guy is, the less his anal sphincter muscles will be able to relax and allow penetration. The more relaxed he is, the more control he'll have over his own body, and the easier it will be.

As for the orgasm, there's no way to tell who will pop first. It depends on what's going on. Is the bottom enjoying himself? Is the top prone to pop quickly, or can he last all night? Too many factors to predict with any accuracy

-- Minotaur




Darran asks,

I have two questions: how long should a penis be? And can I do oral sex if I'm only 15 years old but i really want this?


Dear Darran,

The average length of a the male penis is 6 inches. I don't know how long that is in centimeters. Some guys have more, some guys have less. I know that having a big dick is impressive, but when it really comes down to it, it's not the size that matters... it's what you do with it.

As for doing sex at 15 years. Nobody can tell you when you are ready to have sex. You have to look inside your own heart, and listen to your body. If the only reason you are thinking about having sex is because your friends are, or because you think you should, then you're probably not ready. If you are unsure about having sex, or worried about it, then you're probably not ready. If you feel pressured, or think that your friends will respect you more if you have sex, then you're probably not ready.

But if you have found someone that you really like, someone who makes you feel special and treats you like the wonderful person you are, and if you have spent some time exploring your own body, then maybe you are ready.

If you decide that you are ready to have sex - remember this.

NO GLOVE, NO LOVE.

In this day and age it is vitally important that you learn to practice safe sex. This means never making love without a condom. You are young, you have your whole life ahead of you - don't make a mistake now that will haunt the rest of your life.

-- Minotaur




PDD asks,

We're writing a story with a rather set dynamic- a young (18), exceedingly inexperienced (with either gender) bisexual man and a very experienced, older (31) gay man. For long, complicated reasons we've decided the younger of the pair will be on the bottom for their first time, but what we're running into problems with is the position. The younger man is definitely tense at the beginning of the encounter. There's a huge level of trust between the two, but...

We're thinking of a missionary position for the first time- but we're wondering how easy it will be for the bottom to relax in this position. (We're assuming the top would stick a few pillows under his hips.) The bottom definitely has issues with a doggy-style penetration. What would be the best position for a first time for this pair so that the bottom can relax a bit? Is there anything physical the top can do to relax him more?


Dear PDD,

Well, I think the best actual position for first time is face-down - not really doggie style, but face-down with butt slightly up, like with a pillow under the hips. This allows the bottom to completely relax - he doesn't have to make any effort at all to keep himself up, and can spread his legs wide. This allows full relaxation of the muscles, and the top has to do all the work. With missionary position the bottom has to keep his legs up, and can get cramps from an unfamiliar position (grin).

The top can help by doing everything he can to relax the bottom - from massage to comforting words (if that's what he's like). There's also rimming - this will not only get the bottom used to the anal stimulation, but it's also very arousing in and of itself. If the top is experienced, he's probably done rimming before.

-- Minotaur




Rosa asks,

1) Does anal sex hurt the first few times (due to tightness), do you lose sensitivity/pleasure and tightness after many times, is it ever too hard to get the dick in the ass?

2) Do gay guys get feces on their penis after anal sex? Is it necessary to wash your penis after bareback sex? How did gay guys manage the problem of getting shit on their dicks before condoms?

Oh yeah, and I saw a comment on your site about motor oil used as lube, and once read a Final Fantasy 7 fic with Cid/Vincent and the oil one of them uses to polish his gun, strikes me as unlikely, how many people would like this sort of stuff on their genitals/up their ass? is this really safe?


Dear Rosa,

1) It can, though it really depends on the guys and the circumstances. If the bottom is relaxed, and NOT AFRAID or tense, it can be quite pleasurable. If he's uptight or nervous, it can hurt like hell.

If by "after many times" you mean "many times in a row", sensitivity actually increases, while tightness can temporarily decrease. But remember that the anal sphincter muscle's whole reason for existence is to stay closed, it never loosens up too much.

And yes, sometimes you're just not really in the mood, and no matter how much lube you use, or how relaxed you are, you just don't want anything up there tonight, and nothing he can do will change that.

2) It does happen, but if you know your own body and how "empty" you are, and if you take normal care with your cleanliness (like showering before you go on a date), it won't happen often. When it does happen, you just excuse yourself, go to the bathroom, and clean up. You normally clean up after anyway, as lube is nasty to sleep in (grin).

3) That list was of stuff that could be used in a pinch, not what you'd use everyday. Gun oil is actually a mineral oil (I think), and would therefor be NOT a good thing to use on a regular basis, but for a one-time, necessity-is-the-mother-of-invention kind of thing, it would work...

-- Minotaur