When does anal sex become pleasurable

[Dj1990]

Whenever I masturbate I imagine a guy fucking me in the ass and that's how I cum.
And I do feel my prostate "working" when I cum....gives me an amazing orgasam.

But I've only been with two guys so far...they were both 8 inches...and obviously it was really painful for me. On top of that the feeling like I'm taking a crap doesn't help.
I didn't go back to have sex with either one for a number of reasons but they're irrelevant....so basically I've only had anal sex two times.

I'm sure those of you who are more experienced felt the same way in the beginning......especially that feeling like you are going poo poo...so uncomfortable.
Should I just find a regular guy to have sex with often and it will eventually be pleasurable?

[pellaz]

I bet your more relaxed masturbating than with another man. So may be it will get better. Better the odds tho and continue to try to improve the situation.

[Jay125]

I'm sure those of you who are more experienced felt the same way in the beginning......especially that feeling like you are going poo poo...so uncomfortable.
Should I just find a regular guy to have sex with often and it will eventually be pleasurable?

Have you tried poppers? It's a great relaxant and it also enhances sexual pleasure.

[avidcyclistMTB]

Dj, a lot of the comfort of anal is the partner you are with. Granted, you did start off rather large, but you're built to facilitate it if approached properly and a slow approach and some warmup (fingers, tongue etc.) can be real important if you're new to it.

Personally, my first experience was horrible because of the guy I was with. It was all about him and not me. My present partner is rather thick but he's so gentle and conscious of me that it has never been a problem.

All that said, some guys just don't like anal. Even if you like the idea, you may not like the experience itself. If you're determined, you might want to invest in some different sized butt plugs and work your way up. Should help.

Good luck.

[pellaz]

... I didn't go back to have sex with either one ...

some people are a natural as a top vs a receiving.

[jaxc]

well here's some advice, don't shove anything up your ass that's bigger than a fist and less loving than a dildo:biggrin:

[myapple]

Are you using an enema before all of this anal pleasure? Because if you're not, all that fecal matter packed up in there could be a major reason it hurts so much lol though anal sex is going to hurt regardless if you're not the submissive type. You should definitely relax. The more you tense up and run from it, the more it will hurt. Just breathe. Fingering and cunnilingus could also help you prepare you for it. Dildos could also help you get better at it.

[myapple]

Oh & lubricants. Definitely lubricate well. The dryer, the more painful. The wetter, the better.

[spencer]

Plenty of lube. Also I've noticed the position also depends on how much I can enjoy it but I think that will vary person to person. Ironically the one time I really enjoyed anal there was no lube involved but he didn't get to go in very far so even though I was fine he couldn't enjoy it much so it didn't go down well. Then once we did have lube the position made it hard for me to enjoy it and it was another failure. Practice makes perfect I guess.

[Bowyn Aerrow]

Closeness to the feller you are with does matter - a lot.

My first lover wrecked me for other men. He was too gentle, too sweet and too loving - as such I had very deep feelings for him. The act of sex was intimate, loving - sharing.

Wanting him inside of me was not merely sexual - it was intensely emotional - I wanted him as close to me as possible. Again, not merely 'sex' it was far much more than that. There was a rightness about it, a deep sense of not only pleasure but contentment - safety, security - and much more on an emotional level - sort of a cuddle to the tenth power

My second lover was a brute - he was too quick, far less loving and I really didn't desire him to be part of me in this intimate a way. The idea of him inside of me sort of sickened me a little. It was all about his needs, his 'getting off' - Near nightly sex was a way for him to go to sleep - not an act of love, intimacy, etc.

For my first lover the act was nearly always very pleasurable and often I ended in climax without a reach around.

For the second it felt like a chore - sometimes almost like rape. I never reached climax with him without hand manipulation. Often it was uncomfortable even downright hurtful. His lack of 'giving' affected how it felt mechanically.

While the mechanics of it all does have some bearing here - there is also a need for emotional attachment and a willingness to be part of them - them in you is not just lust - there is more to it.

Most of sex does not take place on the physical side of things. Most of sex takes place in the brain. This doesn't just apply to how 'hot' and 'excited' you get, but also how other sensations feel.

Yes there was a little bit of discomfort at the start (each session) however wanting him (My first) to be as close to me as possible resulted in my relaxing far much more than I did for my second lover (and for those two one night stands). The discomfort quickly gave way to intimacy, joy, pleasure, etc.

I think once you do find your Mr Right you will find that the act is far more comfortable and satisfying (not just sexually pleasurable, but emotionally satisfying) than you have already had.