First time Anal advice

Ok, so first off, how much older are we talking about here? How did you meet this person, and how certain are you about your safety in this situation?

Beyond that, there's no particular reason it needs to hurt. There's this idea out there, often in gay porn, that anal is automatically hugely painful when the top is first entering the bottom and then somehow morphs into this tremendous pleasure as the top keeps thrusting. This is pretty much BS in my experience.

The first guy I ever bottomed with wasn't as big as you're describing, but definitely on large (8 in or so) side. And it barely hurt at all and only until I learned to relax properly.

The key thing here is learning to relax, which can be tricky if you're excited and nervous and expecting it to hurt. Ways to help do this:

1) Lots and lots of foreplay and fingering. Better yet, anal play with toys (real toys, designed for anal play), starting small and working up over days or weeks to something of human dimensions/the size of the top (if you know what that is ahead of time). The point being that if you are having fun with the toys and associating them with feeling good, then making the jump to a penis is a lot easier. Also, you can experiment with toys in private and without feeling any kind of pressure from having another person there. However, if you don't have access to toys, then we go back to 'lots of foreplay and fingering'. Also having the top penetrate you with fingers first, working up to several over time, so you can get used to having something penetrating you.

2) Lube - you can never use too much. Especially early on. Eventually, you'll figure out an amount that works best for you and balances easy of entry with whatever amount of friction you enjoy. But start out with lots of lube and re-apply as much and as often as necessary.

3) Starting position - I generally recommend starting out on your side with the top on their side behind you. That way neither of you is fighting gravity. It can make thrusting awkward once things get going, but you can always shift positions once you're used to having your top inside. A close second for early on positions is the top laying on his back while the bottom lowers himself down onto him. This way the bottom controls the speed and depth of penetration. Or course there is that pesky gravity thing this time, which (if you lose balance) can result in penetration happening faster/deeper than desired.

4) Take it slooowww - at least to start. Again. porn usually shows the top thrusting away like a jackhammer. While that is humanly possible, that is not the only option, and certainly not the best option when you're new at this (or have gone a while without doing it). The thrusting speed the top uses should always be based on what the bottom is enjoying. There can be some discussion around that, but if the bottom is hurting, that's definitely out of bounds.

5) Last, but absolutely not least - Condoms!!! Condoms!!!! Condoms!!!!!! The absolute base rule that supersedes anything else is practicing safe sex.

My 2c worth - assuming you go thru with this. Which in my mind is very much predicated on your answers to my initial questions.

Todd

 

Wasn't this posted a few weeks ago in the sex & health advice forum?

 

AKTodd basically covered everything sex related. Now it's onto the question of how much older this man is and where you met him. Don't rush into sex with an much older man you haven't met in person. There's so many ways he can take control of you and you just don't know what kind of diseases he can be hiding from you. I'm not saying you can't do this, but you have to be extremely, and emphasis on extremely, careful.

 

My one recommendation is to use a butt plug for a while so that you can get used to the actual insertion and begin to relax with something in your butt.