First time bottoming

[young_n_horny]

Well there's this guy I've known and have sorta been seeing for a little over a year now and the sex is great, only thing is he's a complete top while so far I've only been a top but I honestly think I'd love being a bottom a lot more. The only problem with that is not only am I a bottom virgin, but I'm also EXTREMELY tight back there. To somewhat describe it further, the last guy that fingered me had trouble trying to get even just his finger all the way inside me. It also seems to hurt like hell after it gets so far inside. Rimming is fine though and it drives me wild.

The guy I've been seeing for a while too also has a pretty damn big cock. As in bigger than mine for any curious about it. I don't think it helps with him being so big and me being a bottom virgin, but I'd love having his cock inside me. The times we've tried I can just barely have him push in past his head before it feels like he's killing me.

So with that being said, any advice/ideas on how I could go about loosing up? I've tried fingering myself and it just feels weird/awkward like trying to tickle yourself, it only works when someone else does it. I've been thinking of just having him slowly force himself in while I deal with the pain, but it seems a bit scary to be honest.

 

[mandoman]

I'm an anal virgin, and I know that that is the worst idea.
You absolutely need to relax. As long as there is tension, there will be pain. Where there is pain, the sex sucks.
What comes out, is much bigger than anything you are going to allow to be put in there.
It rarely feels bad exiting. You need to either become accustomed to loosening yourself up with your own fingers, or allow him to enter with a pinky, and plenty of lube. Once you are convinced he's not going to hurt you, your first sphincter will relax.
I find the second one more difficult to relax. Tried the wife's dildo, and it took about 10 minutes to relax enough, for it to go in and out easily.
Too much lube is never enough. Other than that, it's a matter of trust, and relaxation.
I hope somebody who actually knows something about it will answer you with some helpful information. Good luck with it.

 

[basque9]

I have broken in a number of first timers and it is rare that a guy is still having pain after I have gotten in once and fucked him thoroughly! Second time around is always better and from then on it just gets better. I did meet one sexy guy , though , who never was able to take my cock..ever! I think you need to get a dildo and practice stretching out your butt, if you want to be all that your top expects!

 

[young_n_horny]

I'm an anal virgin, and I know that that is the worst idea.
You absolutely need to relax. As long as there is tension, there will be pain. Where there is pain, the sex sucks.
What comes out, is much bigger than anything you are going to allow to be put in there.
It rarely feels bad exiting. You need to either become accustomed to loosening yourself up with your own fingers, or allow him to enter with a pinky, and plenty of lube. Once you are convinced he's not going to hurt you, your first sphincter will relax.
I find the second one more difficult to relax. Tried the wife's dildo, and it took about 10 minutes to relax enough, for it to go in and out easily.
Too much lube is never enough. Other than that, it's a matter of trust, and relaxation.
I hope somebody who actually knows something about it will answer you with some helpful information. Good luck with it.

By what comes out being bigger than anything I'd allow in I take it you're talking about pooping? I don't get how I'm able to poop though and have no problem with it yet the minute he sticks his cock's head in me I feel like I'm gonna die.

Is relaxing really all there is to it? I know that I do tense up quite a bit when his cock even grazes my ass since as I mentioned before it's big and while I'm turned on having something like that in me, it makes me a bit nervous too.

For me fingering myself is like tickling/hugging myself as in I don't get any pleasure from it and it just doesn't feel...right (for a lack of a better description). It's like how hugging yourself feels nowhere near as good as having another person hug you tight.

 

[Florida Boy]

The two of you will overcome that entry problem. in the meantime you have an absolutely gorgeous body with a cock to die for. more photos please.

 

[deleted300444]

Bottoming 101: The Bottom is Always in Charge".

 

[young_n_horny]

The two of you will overcome that entry problem. in the meantime you have an absolutely gorgeous body with a cock to die for. more photos please.

Hahah thanks. I haven't posted any other pictures because I feel like posting more would be like repetitive and boring for people to look at. I mean it's just my same body in the same mirror since my computer broke so I can't use my webcam. Well except my phone's webcam but I can only use it as a webcam with that, not a camera (if that confusing sentence makes any sense).

As for the bottom being in charge, yeah that's how things have been with me and the guy I want to bottom for too. He really wants to fuck me but doesn't want to force himself in me knowing I'm in pain. I've noticed though that when he pushes with his cock opposed to his finger we get slightly further in. I guess since I'm a bit eager to have it in me it outweighs my focusing on my asshole for a bit.

 

[MeinTeil]

Is relaxing really all there is to it? I know that I do tense up quite a bit when his cock even grazes my ass since as I mentioned before it's big and while I'm turned on having something like that in me, it makes me a bit nervous too.

Well, OK, you're going to have to get over that. Yes, relaxing is really all there is to it, with a side of being in the right mental place.

I'd recommend that you guys play around backstage with the understanding that you are NOT going to fuck. NOT. So he can tease you with it, finger you, stick it between your legs, play play play all with the understanding that he is absolutely NOT going to fuck you.

You'll be begging for it in no time.

 

[770236]

Take a shower together and start with him eating your ass out. Works everytime (in my experience).

 

[B_thickjohnny]

One thing no one mentioned is that when he's about to enter you - as he's got his head against your hole - you should do what you do when you take a dump. Give a little push and at the same time push against his cock. Don't let him push into you but you back onto him. That works for me and makes it easier. You're in control until you get going and then you can let him take over.

 

[young_n_horny]

One thing no one mentioned is that when he's about to enter you - as he's got his head against your hole - you should do what you do when you take a dump. Give a little push and at the same time push against his cock. Don't let him push into you but you back onto him. That works for me and makes it easier. You're in control until you get going and then you can let him take over.

So I'm guessing by that you mean start off in a doggie position? And thanks for the advice on pushing a bit. I'm thinking maybe MeinTeil might be onto something with having sex a few times with the understanding going in that he's not going to fuck me. Seems like it might make me a bit more comfortable with his cock.

 

[B_Nick8]

Bottoming 101: The Bottom is Always in Charge".

Well not always but for newbies, it's a good idea. :wink:

 

[hot-rod]

Well there's this guy I've known and have sorta been seeing for a little over a year now and the sex is great, only thing is he's a complete top while so far I've only been a top but I honestly think I'd love being a bottom a lot more. The only problem with that is not only am I a bottom virgin, but I'm also EXTREMELY tight back there. To somewhat describe it further, the last guy that fingered me had trouble trying to get even just his finger all the way inside me. It also seems to hurt like hell after it gets so far inside. Rimming is fine though and it drives me wild.

The guy I've been seeing for a while too also has a pretty damn big cock. As in bigger than mine for any curious about it. I don't think it helps with him being so big and me being a bottom virgin, but I'd love having his cock inside me. The times we've tried I can just barely have him push in past his head before it feels like he's killing me.

So with that being said, any advice/ideas on how I could go about loosing up? I've tried fingering myself and it just feels weird/awkward like trying to tickle yourself, it only works when someone else does it. I've been thinking of just having him slowly force himself in while I deal with the pain, but it seems a bit scary to be honest.

You've got to clean yourself out thoroughly. Lie down in the bottom of your tub with a hose of warm water hooked to the shower-head. Do this for a good 45 min. Also, the warm water will really relax everything down there. Then go for it!....lol

 

[young_n_horny]

You've got to clean yourself out thoroughly. Lie down in the bottom of your tub with a hose of warm water hooked to the shower-head. Do this for a good 45 min. Also, the warm water will really relax everything down there. Then go for it!....lol

I'd have to go out and buy a hose then. Normally when we're in a bed naked together it's at his second house about 2 hours from where we both stay so we'd have to find one that fits too. I might be able to do it without a hose though. But the warm water up there would feel good.

Oh any tips on how to shave your own asshole? I'm not exactly hairy back there since I'm almost naturally hairless everywhere except my legs and armpits but there's a small amount of hair back there that I'd have to shave before he'll rim me. Been thinking about just getting waxed, but having hot wax back there makes me cringe just thinking about it. Not to mention having it ripped off.

 

[770236]

After hearing the horror stories from guy's who have shaved their asses, let me recommend you don't. A trim is fine - anything more, and you'll be regretting it for weeks.

 

[D_22]

I've shaven my ass a few times, had no problems.

 

[B_thickjohnny]

I don't think you necessarily need a hose to clean yourself but prepare a day or two in advance if you know it's coming. I'd take fiber pills to help bulk up what you pass. You'll know when you wipe - the less on the paper, the better (cleaner) it is up there. Regarding shaving your ass crack, if you're already naturally smooth, I wouldn't worry about it. The little hair you might have there might be fun to play with. If you really want to go totally smooth, either go get waxed or use Veet (CAREFULLY!). Put a cloth over your hole as that skin is very sensitive. Put the cream on for no more than 5 minutes (instructions say no more than 8 minutes) and then scrape it off. You can then shave the leftovers. Sure wish you had some photos to share!

 

[D_Upsy_Daisy]

Is relaxing really all there is to it? I know that I do tense up quite a bit when his cock even grazes my ass since as I mentioned before it's big and while I'm turned on having something like that in me, it makes me a bit nervous too.

It's part of it. I know that when I'm alone, I can take a fairly good sized dildo/etc. But when a guy is about to penetrate me with his cock (which is way smaller than my toys), I get really nervous/tense and he can't even get in without pain.

 

[damnimbi]

It's part of it. I know that when I'm alone, I can take a fairly good sized dildo/etc. But when a guy is about to penetrate me with his cock (which is way smaller than my toys), I get really nervous/tense and he can't even get in without pain.

I had this problem initially. But it all comes down to relaxing. The best way is to find a partner with whom you share great chemistry. The natural vibes will turn to natural passion. Mixed with trust, you'll learn to relax properly.....and enjoy a great time!

 

[young_n_horny]

I don't think you necessarily need a hose to clean yourself but prepare a day or two in advance if you know it's coming. I'd take fiber pills to help bulk up what you pass. You'll know when you wipe - the less on the paper, the better (cleaner) it is up there. Regarding shaving your ass crack, if you're already naturally smooth, I wouldn't worry about it. The little hair you might have there might be fun to play with. If you really want to go totally smooth, either go get waxed or use Veet (CAREFULLY!). Put a cloth over your hole as that skin is very sensitive. Put the cream on for no more than 5 minutes (instructions say no more than 8 minutes) and then scrape it off. You can then shave the leftovers. Sure wish you had some photos to share!

Photos of my ass? I could take a few more. I have one or two in my photos I think. As for the little hair I have, my friend wants all the hair gone before he'll rim me. And seeing as how just making out with him has made me cum before I'd love to see what he could do while rimming me.

I think I'm fine on the bowel movements part. Never had any problems being messy in there so I'll be fine.