First time bottoming

young_n_horny

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I want to try my first time bottoming since I believe I really am a lot more of a bottom than a top but I have a problem or two.

Every time I've tried bottoming the guy gets in to a certain point and after that I tense up and it becomes painful as all hell to have them try to push in further. Is there an easy to to overcome this? I did once with this guy I play with sorta regularly who has a HUGE cock (he's like a mini Quercusone) and our most recent time we got to that point and then since I wasn't feeling well already before we started and had been having a headache, I guess the headache combined with the awesome feeling made me nearly pass out. But before I told him I had to rest for a sec he slid pretty far in and my cock instantly got rock hard as well. I guess almost losing consciousness relaxed me, but I know I won't be almost passing out anytime soon again.

We've tried lube and even shaving my butthole since the hair was pretty much absorbing all the lube but even then that helps only a little. I've tried with smaller guys too and had pretty much the same results. Any help is appreciated!
 
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davidjh7

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The best advice I can give you is to get a couple of progressivly larger dildos, small to as large as you want to take. Make them vibrators, to help you relax the muscle. It is like anything else, you have to train. Using the toys puts everything under your control, so you can go at exactly the pace you want and need, stop, sart, change angles, etc. Teach yourself about yourself before you bring in the other guy. I suspect you will find an ah-ha moment with the right combination, then you can teach your top, then expand from there. And more lube--use a lube that lasts longer than the pure water based, but make sure any you use with a partner, who should be wearing a condom, is compatable with latex. Good Luck!
 
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Q Vee

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Cleaning out is a must especially for deep dicked, balls bangin, anal sex.
Sometimes, it can work spontaneiously, but you run a greater risk of being messy. Also, thursting can be more painful if the dick is pushing the feces back up the colon.

So, prepping by not eating for a few hours after a good poop and/or with an enema will give you a nice clear and clean fuck chute to start with.

Being rimmed can be both very relaxing and exciting. And the more fingers that you can become comfortable with will really make the insertion of any cock more accommodating. Using a dildo (with same prep as above and lots of lube) prior to the real activity is also a favored practice by many.

And always!! Always!! Always!! Use lots of lube. Take your fingers or his fingers and get some lube up into your asshole (so it's past the ass-hair that seems to be at issue for you). And also lube his dick from tip to base, repeatedly as necessary.

Unless you are certain of his negative status a condom is required.
NEVER USE A CONDOM WITHOUT LOTS OF LUBE.
Dry condom use simply makes entry more difficult, creates burning friction with every stroke, and increases the likelihood or breakage.

Once you have a dick up your ass, as long as you still have normalcy to your sphincter muscles, there will be some pain. Relax. Breathe out. Push out as he pushes in. Try not to tense and squeeze. Sometimes, after the first ring is breached it can seem unbearable. Have him take it out, catch your breath, and start again after the pain subsides. It is amazing how less painful a restart can be.

There is a difference between the pain between your "inner rings being popped" and the pain when a thrust is hitting something the wrong way. A position change may be needed. That can depend on the shape of the dick and your own internal configuration. You just have to experiment and find what works best.

A pounding beat down is not usually the best way to break into bottoming. Going slow, taking time to enjoy the experience and working up to a faster pace can be a really great fucking experience.

There are a number of threads on here with similar and even better advice so do some searches and read what others have said also.

I hope you find someone who will give you that first great makin-love-to-your-ass experience. And I hope I get to hear about too! LOL!!!

HAPPY HUNTING!!!!
 
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young_n_horny

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That's just the thing though. I usually like having a guy there since it feels awkward if I even finger myself. Funny you mentioned a vibrator since the guy I hooked up with today used one after I told him I'm a bottom virgin and we actually got the vibrator almost completely inside me but when he tried putting his cock in it hurt. I'm guessing that might partially be due to the fact that we stopped for a good 15-20 minutes after using the vibrator since we were kissing a lot and my hole probably closed up.

I also can't practice much myself with one since I don't have much of any privacy at home and share a room (complete downer when trying to jack off).
 

CygnusKnights

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So far the advices given seem to be extremely great, but here is my personal touch to all of this.

"cleaning out" is optional as I don't really care about this. That's up to you and your top...

What I suggest you try is, perhaps a little bit of alcohol. That should relax you.. but if you have too much.. well you're screwed.. pun intended..

And I don't know what kind of lube you use, but based on personal experience, KY jelly does the trick for me. It's a bit pricey but I think it's worth it. You don't need much of this and reapplying a little amount every so often does wonders.

Now for the actual physicality of it all. How do you usually get it in? Try getting on top so you control how much goes in and the pace. Sometimes the initial penetration can set the mood for things. If the top is too eager and rushes in, the "ring" gets a bit of a shock and you'll experience unnecessary pain. Doing it right shouldn't hurt... If you prefer to be on your back.. reapply lube often.. but once again, take your time. Smear the same amount of lube you would all over the penis you'll be having inside, all over your hole and if possible some inside of you.

Virgin bottoms or new bottoms tend to get sore pretty quick.. especially if the lube dries up mid-fuck. What I suggest is you relax and slowly use shorter thrusts rather than longer, deeper thrusts. Also avoid if you can, pulling out completely and jamming back in.

Other than that.. All I can tell you is, practise stretching yourself out.. I'm sure you can think of ways :)
 

dong-in-khakis

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I have this exact experience with my new friend. I have used toys before and they went in fine. After years of watching guys fuck with ease (in vids) I had no idea the pain would be so great. Just like you, my bud got in about an inch then it was like he was pushing against a brick wall. When he pushed harder there was burning friction that hurt like hell. On our second meet when I took control, made myself relax and pushed against him he got past the "wall". He has about 7.5 and got all the way in me. It felt good and hurt. I know it was because I was tense.

I want to make a bottom for him bad. We're still talking about trying again and will. I believe what everyone says, there will be some pain, but mostly it's a miond over matter thing initially, you have to make yourself relax for successful entry.

Good luck.
 

needsmust

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That's just the thing though. I usually like having a guy there since it feels awkward if I even finger myself. Funny you mentioned a vibrator since the guy I hooked up with today used one after I told him I'm a bottom virgin and we actually got the vibrator almost completely inside me but when he tried putting his cock in it hurt. I'm guessing that might partially be due to the fact that we stopped for a good 15-20 minutes after using the vibrator since we were kissing a lot and my hole probably closed up.

I also can't practice much myself with one since I don't have much of any privacy at home and share a room (complete downer when trying to jack off).
To me this post might hold the answer to your questions. If you are too uncomfortable, mentally, to finger yourself then you probably aren't ready for anal sex period. It's not unheard of for gay men to carry some deep level shame about being penetrated or shame about the fact that it is your ass. Maybe take a look at your thoughts on whether getting fucked is linked to submission or being less of a man.
After that maybe take some time home alone, have some drinks and once you have a comfortable buzz going put on some porn and just play with your butt. Keep going until you forget the uncomfortable part and are just focused on the pleasure. Do that a few times and then invite a guy over to join you. Don't try to fuck, just let him finger you and play with your hole while you watch porn and jerk off. Maybe later move on to dildos and eventually you might work up to fucking.