Akward Question- How do you actually 'Do it' properly

Having come out recently , it is likely that in the near(ish) future i will be sexually active for the first time.

I feel stupid asking this at 25 but how do you do it properly, how do you prepare youself, how do you know if you are pleasing the other person, and how do you endure the pain of anal etc etc

Any tips would be appreciated, i only have porn to base this off of and i don't think it is very reliable.

I feel dirty just asking these questions...

 

No...you're fine in asking. What I would suggest is getting hold of instructional books such as; "Guide To Beginner's Gay Sex or instructional DVDs. Also, check out some gay porn videos ...in this respect they can be very informative from a learning perspective. Good luck and Best wishes...JS

 

Well first off, sex isn’t suppose to be painful. If it hurts you’re doing something wrong. Second, you can ask the person does it feel good, or what do they like.

Get into the habit of foreplay, it prepares your body and mind to be “into it”. I also find that taking a shower beforehand helps, but others may like the natural smell of a man. You won’t know till you ask.

I’m terms of doing it properly I assume you’re taking about anal sex; you have people that either like it or don’t, and bottoms or tops (or both). One of the things you gotta do for anal is having a bowel movement beforehand. Some people at this point like using enemas to make sure the inside is clean, or the top can also wear a condom for safety and cleanliness purposes.

“Properly” is subjective because not everyone likes sex the same way. My boyfriend and I are quite vanilla when it comes to the bedroom, while others are into more kinky stuff.

 

There are books and instructional DVD's?! I'm far behind the times, i feel like porn videos aren't really accurate and the porn actors are just 'putting it on'?

Is there a way to make anal sex less painful over time, like building up an immunity to it?

 

I've heard that the position really matters, like missionary is supposed to be less painful than doggy, I'd suggest looking into that kind of thing.

 

Yes there is...actually there are videos on YouTube that talks about the painless anal sex experience. One guy in particular you should check out is Davey Wavy. He just recently uploaded a video about this topic.

 

Yes, there’s a way. I personally enjoy bottoming more when I know I’m clean inside. Positioning matters to me. For example, I don’t feel very comfortable on my back while my boyfriend is standing on the edge. You’ll have to figure out what position works for you.

 

Hey NGJon,

So far this thread has basically focused on anal sex. For additional information along those lines, I would direct you to the EC Resource Health page to find information on Anal Sex, Gay Safe Sex, STDs/STIs, etc.

http://emptyclosets.com/home/pages/resources/health.php

But I would also recommend that you research and understand other forms of male-male sex that don't include anal penetration. Beside the fact that some guys are pretty much exclusively tops, others bottoms and still others are versatile, not all gay men care to engage in anal sex. Don't ever let someone elses' preference(s) dictate your own, especially when it comes to your own level of comfort. Sex is about mutual pleasure and if you agree to tolerate or endure someone elses' preferences when it comes to sex, how much pleasure are you getting out of it yourself? Sex is a two-way street. (Absolutely NO anal sex pun intended.)

So, perhaps do some research on fellatio (oral sex), mutual masturbation, frottage, and intercrural sex. Sometimes, just "being" with someone that you are strongly attracted to and getting off together in an intimate setting/environment is the point.

 

Not a gay guy myself but know a bit about anal.

Shouldn't hurt if done right, but the problem is that people rush. It's best to work your way up to an actual penis. Have your partner use his fingers or smaller sex toys on you first so you can get used to the sensation, then insert the dick once stretched. This especially helps for the first time. Make him go slow, anal is a lot different than vaginal penetration and you cannot just ram in at once or else it -will- hurt.

 

LOL! I wasn't going to expound on anal sex, since that has been so much of the topic of this thread, but @Creativemind brings up some important points. First, as she said, anal sex should not hurt from the bottom's experience. Second, as she indicated, foreplay - normally long foreplay with the bottom's anus - is extremely important. Focusing on the bottom's point of view, if you think about it for a moment, you have probably expelled large turds through your anus from time to time without pain. Thus, the size of something (a dildoe, multiple fingers, a penis) coming back up through the anus should not technically hurt. Something to keep in mind, however, is that your anal muscles have to be relaxed. Pain (unless the object being inserted is of unusual girth) comes from the anal muscles being held too tightly closed. There are two separate sets of anal muscles. An outer ring and an inner ring. An experienced bottom learns to relax both sets of muscles prior to penetration.

The point of all of this, of course, is to allow his partner's penis to penetrate at least far enough (at least an inch or two) into the anus in order to stimulate the prostate gland. Prostate stimulation (whether it is done with fingers, as dildo or a penis) creates a separate level of sexual stimulation and can lead to a completely different orgasm than penile ejaculation.

However, back to the point of painless penetration of the bottom by the top, the main issue/point is really all about foreplay. The top can do various things (as can the bottom for himself) in order to relax the anal muscles before any attempt at penile penetration. NOTE: All of these methods require the use of copious amount of lube (lubrication), since the anus does not self-lubricate to any degree similar to a stimulated vagaina). These include stretching of the anus with finger (fingering). Normally starting with one finger. The 'rule of thumb' is that when you can get three fingers in, the anus is ready to receive a penis. Fingering, however, isn't only about 'sticking' them in, but also about stretching and pulling (not painfully) the anus more and more open over time. In addition, if the top is willing to rim (lick the anus) of his bottom partner, that not only feels pleasurable to the bottom, but can definitely help to open up the muscles of the anus. And, of course, using dildoes (starting with one of smaller girth initially) can help loosen the bottom's anus for painless penetration.

Of course, all of this mostly presumes that the top's penis is within a reasonable girth and length. Average girth (according to my information) in about 4.6 inches (about the maximum width of a tube of toothpaste) and the average length of an erect penis is about 5.2 inches.

Just saying...

 

I agree with all of the advice given here. I will add my experience as well.

I am fairly new to bottoming, and have only bottomed in the last year. My experience was that it was painful to begin, simply because of my nervousness and anxiety over the pain. When you are not relaxed, you automatically tighten your sphincter muscles. Unfortunately, you can't simply tell yourself to relax - that didn't work for me because your body will react regardless of what you tell you mind.

All of these suggestions of relaxation techniques, such as foreplay, and using lots of lube did help. What also helped for me was for me to be fully aroused (and erect) prior to being penetrated. Although I don't need it as much now, early on it helped me because the penetration was more arousing than painful - and the endorphins being released by my arousal helped to convert what would be deemed painful into actual pleasure. So, by masturbating myself during initial penetration, I was able to easily take the penis with no pain, but in fact lots of pleasure.

That's what worked for me.

 

Relax and practice. Relax and practice. Over time you'll find it gets better with experience and you'll try all sorts of things. Some you'll love others not so. But if you don't try you'll never know. No one is perfect the first few times. My legs shook at first but once my nervesness went I realised just how enjoyable it all was.

 

Someone mentioned the how to videos, but there is a Gay guide to anal sex porn vid I had downloaded awhile back. I was a very late comer to anal sex and in my mind I just assumed it would hurt and I was just making sure that if I was giving I wanted to do all I could to make it feel good for both parties. The first time I had full on anal sex with a guy I was 25 myself. I have only ever bottomed twice but when I did I was on top or riding because I felt it would be the easiest for me to control it. When I did try bottoming the 2 times it did not last very long, I top more often and enjoy doing that. I kinda want to try to be a little more versatile, and maybe will in due time. But all in all that Gay guide to anal sex video is a pretty good one. Also, all the others have provided some pretty helpful tips and advice too.