Regarding anal ... too painful

[Chris88]

Hi everyone

As a bisexual male anal sex is probably something that will come up in one relationship or another, but having never done it I have a major problem...

The few times Ive tried pleasuring myself anally, its immensely painful....
Ive tried tips and tricks that Ive read on sites similar to this, and Ive asked a few people for advice to try and make it less painful, but to no avail!
I don't understand what Im doing wrong but 1 finger is the most I can get up there, and once I try to pull it out its pretty bad >.< The same goes for any movement once its up there. The only part that doesnt hurt is sliding it up in the first place. Any larger objects or more than one finger is just way too much.

Ive tried relaxing and doing it, I always use lube but....I really don't understand it!

Does anyone know whats wrong with me/what Im doing wrong and how I can fix it? Id hate to say no to a potential boyfriend simply because "its too painful"

[DVDBear]

For starters the two things you'll hear over and over . . . if you think you've used enough lube, DOUBLE IT. And you may want to stick with a thicker type like KY for now. Doctors use it for a reason. Secondly, go very slow, both in AND OUT until you're more used to the sensations. You may want to try the smallest butt plug available, about the size of a thick finger, SLOWLY insert with a lot of lube and leave it in for awhile while you lie down and relax. Hopefully your muscles will do so as well.

If this still doesn't help you may have to resign yourself to the fact anal may not be for you. Some people simply can't overcome the problems you're experiencing. If that's the case practice being a good top . . . . they're always in demand. LOL

[Chris88]

Hehe, thanks for the reply, I'll definatly give those methods a try.
I do hope that I don't have to give it up, could be dissapointing >.<

[shaved bi]

I agree DVDBear! Start small and slow with a lot of lube. I did years ago. I can take 1 1/2" diameter now and it is very enjoyable.

[Tommyhot]

Here is a short tutorial I typed up a while back. It's how *I* learned..

The key to this is to take your time and go slow. You learn how to control your butt and schincter muscles. You learn how to RELAX THEM and you get used to the feeling of it all.

Anal play for beginners

Disclaimer: I am NOT a doctor and I do NOT play one on TV. This is the way *I* learned how to discover anal play. As usual care needs to be practiced. GO VERY SLOWLY.

First start off with a TRIMMED index finger. You may even want to put on a latex glove first to help make it even smoother. Use KY or the drug store brand of KY and lube the finger well. Place it VERY GENTLY near the anus and lightly circle the hole with the finger. DON'T INSERT YET. Just circle it for a few minutes. After a few minutes without insert, just put the finger over the anus and gently press a bit without entering. Just apply a bit of pressure.
Do this over and over a few times and after a few minutes SLOWLY begin to insert JUST THE FINGER *TIP* in about a quarter of an inch then take it out. Do this a few times then go a LITTLE further in. Repeat this until you have you whole finger in. DO NOT FORCE IT, IF HE OR SHE OR YOU SAYS STOP, STOP!

Within a week or so of trying this the person should be fairly used to the finger and inserting and pumping it in and out should become easy. Also try moving the finger around while inserted, back & forth,etc. Orgasms ARE VERY VERY INTENSE when you leave your finger or butt plug or dildo in.

Soon you will want to try something slightly bigger than your finger. Try your middle finger or graduate to a SMALL butt plug. Same rules apply to the new toy as did with the finger. Start off using the finger as usual then after getting loose begin with the plug.
Plugs have flared bottoms to prevent them from going all the way in. If you graduate to dildos later get ones with a flared base or ones that have the balls at the bottom. This prevents them from slipping all the way in. You don't need a trip to the ER to retrieve it, that would SUCK!
After a while you will become very used to anal play and you won't need much time to prep for your session. You'll loosen up very quickly after you learn how to relax your anal muscles. It takes me less than 5 minutes to go from start to riding a 8 inch silicon dildo like a bucking bronco!
GITTYUP LITTLE DOGGIE!

The key to learning anal play/sex is to TAKE YOUR TIME.

[Ephemera]

A friend of mine is gay and he's only a top - he doesn't like anything large being put in his anus, just like you. Maybe you just won't enjoy being penetrated. It's not a big deal if so.

[dancingdoc2]

"Playing Ball" and How To Tips for Prostate Massage

The information in the above link should also help to solve your predicament.

[Rawbob]

To be honest, its probably more of a mental thing than a physical thing!

As others have said, get lube, use it and use LOTS OF IT!

No bull****....you can't use enough when you're starting out.....its also VERY difficult to really "finger" yourself and get the same sensation you get when its done by someone else.

You might want to hire a gay male massuse who specializes in prostate massage - cause trust me, anal sex is NOT about the penetration..its about the stimulation of the prostate!

You might want to buy a soft 1" thick dildo and try that or better yet, buy one of those "prostate massage" instruments...here's the site: http://www.aneros.com/category.php

I have one and its a great tool, it dosn't hurt to put in and you'll immediately feel how it hits your prostate!

Also, find a bi buddy and explore together! That's always a fun way to explore your sexual self!