So I've been involved with this guy for about two months now and in that time we've become closer and closer everyday. We've kissed and done lots of heavy petting, but we haven't actually had sex yet. It came pretty close to happening on Friday night and after talking to him this morning, we both decided that it was the right time for us to take it to the next level.

He should be over here in just a few more hours and I'm starting to get a little nervous. I'm a virgin and haven't had any anal play yet. My boyfriend is a really big guy. He's very tall, pretty chunky, and he's pretty big down below. I'm really short and skinny and narrow hips and I'm concerned about anal being very painful for me. I want to make him happy and he said that I could be the pitcher first. It's no worries for him though, he's not a virgin and he's got a huge ass! I'm a little guy and average at best, so he doesn't have any pain to worry about.

Should I go to the store and buy some lube or what? I've got some vaseline and cooking oil that have both worked fine for masturbation in the past, but is there something better I could use? Any advice or words of support?

Thanks!

Thats gay.

Sorry at first I thought you were a girl and I was going to ask why you'd do anal before vaginal penetration.


Anal sex... ick.. I've allways found it painfull and horrible, but that's because I do alot of leg excersize. I can barely get my little finger up there, let alone a dick.

..So when I have to give my boyfriend anal sex I take a shit load of paracetamol before hand. I dont know if it works but I can pretend it does. I also take something relaxing like a valium.

When the time comes, try to be relaxed. If you're tense, your ass muscles will be tense, which will make it painfull.
YES get lube, but make sure it's one that is okay for use..internally. Some arent, and they can hurt a little.If you cant find any specific massage oil is quite good.

Get him to use his fingers first, build up from one to two and so on. And tell the bastard not to be rough and just shove it in.


good luck.

Thanks yoyobek. I don't think I'll be able to get any drugs today, but I'll try to take it slow like you say. I might have to work my way up to it.. I do a lot of exercise myself. :)

If you're looking for lube get ky-jelly.

I'm a guy and anal sex is definitally not the next level its more or less one of the last ony thing after that is all the crazy shit. Stick to vagina sex. If you haven't been broken you definitally wouldn't want your asshole to be the first.

He does not have a vagina. Haha.

USE A LOTTA FUCKING LUBE.
And I wouldn't let him stick in your ass the first time you guys have sex, I'd let him to anal play the first time and then you guys could have sex a different time or something I don't know

You probably should just try anal play first, not anal sex. That would most likely hurt alot unless you've explored it before.

Relaxation is the key. HAVE a couple of stiff drinks before hand or smoke whatever shit you crazy kids smoke these days.

Lots of lube and play before hand and most importantly of all

The idea of it most turn you on...i mean REALLY turn you on...the thought of him taking you. Does the idea of it make you hard? Does imagining it make you feel good?

If not, don't do it.

Strange nobody mentioned poppers yet. Yes, terribly stereotypical, I know.

i thought you were a girl at first :(

this thread is gay

ask ur gay buddies what position hurts the least

That = good advice.

A lot of lube. A lot of lube. A lot of lube. I cannot emphasize this enough. I'm straight and I still have to use a lot of lube on tight girls, and their bits are self-lubricating already. Your asshole is not. Don't risk damage to yourself. Pain, well... that may happen anyway.

For Christ's sakes, use a condom. We don't need one more "I was gay, and got AIDS" poster boy ruining the American conceptualization of homosexual relationships as unique and beautiful things. It's a pity most of our citizens are such twats about gays.

And most importantly, never go ass to mouth. Just.. don't do it. Never go ass to mouth!!

(By the way, for all of the pricks out there who will undoubtedly get their panties in a twist because I defended gay people, watch this video: http://www.youtube.com/watch?v=TgBIUiSWRVY OP, you might get a laugh out of it, and for the rest of you, well, I hope it makes you feel like the assholes you are.)

use actual lube, not vaseline. there's something in vaseline that breaks down condoms and makes them not as effective.

Didn't occur to you to just ask your boyfriend?

For Christ's sakes, use a condom.

This, and:

use actual lube, not vaseline. there's something in vaseline that breaks down condoms and makes them not as effective.

All oil-based things do this, actually, but the point remains. Someone mentioned KY earlier - that's waterbased, so it's good.

Lube. Lots of foreplay. Be relaxed. Listen to ketch(I still read your name as jackktech). And DON'T use lube with that 'warming feeling'.

Good luck.

Whoever he is, he is the luckiest man alive.

Yep, use LOTS of lube! Anyone here ever read Tucker Max?
Make sure you use plenty of lube.

lol

OP is a dude.