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Will the real thing feel better?

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I'm a 20 y/o male, only recently stopped being in denial about being gay, so still a virgin. I'm eager to get out and live a little, find a boyfriend, have sex and all that, but the prospect of bottoming worries me. I mean, the idea of it really turns me on, but I've messed around with using fingers and small objects as makeshift dildos and it doesn't live up to expectations at all. There might be a brief spurt of pleasure here and there, but mostly it's just nothing, or that awful "shit got stuck half-in/half-out" feeling. Is this really what anal sex is supposed to feel like? I mean I could barely even tolerate "thrusting" it in and out because it's so uncomfortable, and mind you a finger isn't even half the size of a dick. I'm hoping the real thing really is just that different somehow, but I don't know, right now I don't see how I could ever do this.
 
When you were learning to ride a bicycle, did you set out on day 1 to ride in the Tour de France? Probably not. You probably started with a tricycle and worked you way up to where you enjoyed riding and you might be an enthusiast... but probably not a professional bicycle racer.

What you're focusing on is something that is a relatively small part of a gay relationship. There are gay men who fuck like rabbits but there's also gay men who have active sex lives that don't involve putting things up their ass. The thing that both groups have in common is that they got out there and tried different things until they found what they liked and didn't like.

At this point in the game, you're a virgin. The focus should be on finding someone to get naked with and explore. That exploration is emotional, it's sexual and it's as much an exploration of who you are as much as it is an exploration of another man's body. So, don't worry about whether you're going to enjoy playing hide the sausage and instead focus on finding a nice guy that you like who is attached to that sausage.

Returning to the bicycle analogy, expect that you're going to ride with training wheels until you get the hang of it. Expect that you're going to fall down, skin your knees and land on your ass. Expect that you're going to pick yourself up and try again until you get it right. In the meantime, the questions about specific sex acts and all that stuff will work itself out.
 
I appreciate the response, but with all due respect, that doesn't really do much to put me at ease. I know that there's more to a relationship than just the sex, and honestly I probably care less about it than most guys do. I'm much more interested in finding a guy I like than rushing to lose my virginity. But if and when I do find someone, I'm sure sex is something that'll come up eventually, and I don't want to go into it a nervous mess who's hesitant to try anything because my only idea of what to expect comes from a few awkward fingering sessions, which is where I'm at right now. I know you should be patient, work your way up, etc., but if I can't comfortably simulate the fucking motion with something as small as a pen after a half-dozen to a dozen times, it just seems like I'll never be "ready." It freaks me out because I really don't want to live the rest of my life exclusively as a top or just doing oral or whatever, but if I can't get used to bottoming, that's pretty much what I'm looking at, which would totally suck for me and probably for whoever I'm with too.
 
Desire, either yours or your partner's is important in terms of what you are describing. Also, penises have more "give" so to speak than most objects and dildos. A partner also is in a different position and angle than your self-stimulation. And, if you don't want anal you don't have to have it, but you'll need to find someone who is ok with that. My husband and I have been together over 30 years and we've been more oral than anal.

Over time, if it is something you wish to pursue you'll learn to relax. The anus is sensitive with nerve endings and inside the pressure against the prostate feels good for most guys.

There can be a hang up due to the bm function or to the idea of being "taken." The pleasure factor usually overrides those issues. Be careful also of assuming that pornography depicts the only way things are done. Taking a hard pounding from a hung power top is not for everyone and certainly not for someone new to sex.

I think the best advice I can give is to cummunicate with any and every partner, practice safe sex and only do what you are comfortable doing. Even versatile people usually have a preference of what they like doing.

This time and stage of your life ought to be full of fun and experiment. If you'd like to practice more anal stimulation but a small dildo bit will be the right shape. Lube it and yourself well. Turn yourself on by whatever means you find hot. Out it in and just let it be there without movement until you get used to it. But, again, if it's not for you don't worry and don't let it stop you from doing it to someone who wants you in them.
 
I appreciate the response, but with all due respect, that doesn't really do much to put me at ease. I know that there's more to a relationship than just the sex, and honestly I probably care less about it than most guys do. I'm much more interested in finding a guy I like than rushing to lose my virginity. But if and when I do find someone, I'm sure sex is something that'll come up eventually, and I don't want to go into it a nervous mess who's hesitant to try anything because my only idea of what to expect comes from a few awkward fingering sessions, which is where I'm at right now. I know you should be patient, work your way up, etc., but if I can't comfortably simulate the fucking motion with something as small as a pen after a half-dozen to a dozen times, it just seems like I'll never be "ready." It freaks me out because I really don't want to live the rest of my life exclusively as a top or just doing oral or whatever, but if I can't get used to bottoming, that's pretty much what I'm looking at, which would totally suck for me and probably for whoever I'm with too.

hi buddy,

i was in your shoes once. i didn't even try bottoming until several years after hooking up with guys. i even found it disgusting in the beginning to touch even my hole. lol.

but like karabulut said, you're just starting out. don't expect to be an expert right out of the gate.

but let me get straight to the point.

i don't want you to experience the bad experience i had when i bottomed for a guy. he basically forced me to bottom for him without much preparation. bad decision.

so, first of all, don't expect the first guy you meet to go into a relationship with you. the most likely outcome is he just wants to hook up with you. which is well and good since i bet you want sex too just as badly as he does. it's just the way guys are made, i'll understand if you're a lesbian. so there's nothing wrong about getting off and having a one-night stand with another guy. at least, you'll hopefully learn to kiss. maybe suck dick or get sucked.

but onto your problem. when done correctly, bottoming can be a great experience. just like a vegetarian having his first steak, it's an acquired taste. but once you learn to appreciate the flavor and texture of it, you'll keep coming back for more. fingering yourself with a bare finger, yours or others', WILL HURT your anal linings. avoid doing it with bare fingers.

anyway, when you're alone and have enough time, empty the tank. or you might want to buy an enema bottle and perform an enema yourself. don't use the chemical that is sometimes included in the bottle. dump it, rinse it and fill it only with warm CLEAN TAP water. i repeat, warm water. NEVER HOT OR YOU'LL END UP IN A HOSPITAL. Stop when the water is no longer cloudy. 3 flushings is usually more than sufficient.

lube your ass. get a condom and put it over your finger. lube it and play with the entrance of your hole. get familiar. get comfortable with the idea. AND DON'T FORGET TO LOCK THE FUCKING DOOR! ass play is as much physical stimulation as psycho-sexual stimulation and release. play with your bud by running circles or pressing or whatever, just make yourself familiar with that part of your own body.

insert slowly. BREATHE. RELAX. apply constant pressure to your ass when inserting your condomed finger. do it slow. be comfortable with it. keep it lubed. insert your finger until it is all the way in. then start fingering your hole in and out slowly. do it as long as it is comfortable. when you feel pain, stop. the idea is pleasure, not pain. finger yourself and explore the sensations. enjoy it.

when you have been comfortable with playing with your ass with a finger inside a lubed condom, put in 2 fingers inside the condom this time. do the same process. when you have become comfortable with the sensations, try to stretch your hole a little with your two fingers.

do this exercise a few times to be comfortable with yourself. i don't advise 3 fingers. find a Real Cock find a versatile guy, not a top. a gay guy who is hiv- and into vanilla sex and not a straight guy. This will take the edge off the initial experience. AND FIND SOMEONE LESS THAN 6 inches. you'll thank me for this. preferably with a slender dick. thick dicks hurt. everyone loves a big cock. but it's not fun when you are just starting out to bottom.

bottoming is a great way of getting and giving pleasure to your partner. just make sure you play safe. know your status.

sex is 1.3 billion years old. it's not your fault. it was meant to be enjoyed. do it safely with others.
 
I think both of you might've misunderstood me a bit, in that I'm not really experiencing pain in the conventional sense as much as discomfort. I haven't had any trouble with insertion or anything (not that I've tried anything big yet), but once it's in it just feels like I'm in the middle of a bowel movement. Usually that's when (I assume) the sphincter isn't fully relaxed, but then when it is, there's pretty much no feeling until I pull out/push in, when it then feels like crapping again. I know I'm actually not, so it's not a mental hangup, it's just not a pleasurable feeling.

I guess what I'm wondering is if that's actually what anal is supposed to feel like. Like, does that sensation dissipate over time, or differ with actual sex? Is it something you just have to learn to tolerate? Or is that what's actually supposed to be feeling good? I didn't really conceive this as a generic "what does anal feel like" thread but I guess that's kinda what it is. Thanks for all the advice though guys, it should be helpful.
 
Well like I said it's an acquired taste. It takes time to be comfortable with the idea and the sensations. But you won't really understand unless you do it with someone. Hopefully someone you are really into. It makes a big difference.
 
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