Anal sex and simultaneous orgasms might not often be thought close bedfellows. One man comes into the other, right? And that other – well, his pleasure is different; if he wants to come too, if the prostate stimulation alone doesn’t do it, he’ll just have to wait his turn. There’ll be a lot of times when this is fine, but if, as the bottom, you consider those times when your top’s lying next to you, spent and preparing to snore, and you’re still hard, or if, as the top, you recall your partner’s wandering hand toying with your one-shot-per-hour, now flaccid penis, then you might think simultaneity is worth a try.
Being the bottom can feel significantly better if you haven’t yet come. The prostate stimulation is more intense, and the feelings of fullness and friction more richly satisfying. In other words, the answer for the post-ejaculatory-top dilemma is not for you to come sooner, rather than later. Your orgasm will also tend to be a lot more intense if he’s still inside.
One solution is for the top to take time out from pumping and concentrate on working on his partner’s erection. For the top, in the heat of the moment, that can be easier said than done.
Bear in mind, that while receiving anal sex, the bottom can tend to reach orgasm very quickly when his own penis is being aroused. While it can be good throughout sex to stimulate his penis, the more intense pleasuring is best left until towards the end, when the top is approaching climax. Unfortunately, this can be the point when the top least wants to stop. He’s going guns, and it’s too late now.
The top might well want to continue to move and strain – in which case, a shift in position can allow him to feel he is still working while lessening the stimulation of his penis.
If you’re in missionary, kneel back and lift your partner so he lies arched over you. Gravity will pull him down on your penis, and you’ll still be able to feel you’re pushing upwards, but your movement will be inhibited, allowing you to pace yourself while you and/or he stimulate his erection.
If you’re standing or doing it doggy, pull his upper body towards you, so you’re leaning back slightly, and you’ll be able to feel you’re still being active while having full access to him.
Either way, seek to match your thrusts with your hand moves, maintaining your own level of arousal without yet tipping over the edge.
Rather than attempt absolute simultaneity, you might wish to err on the side of caution, in which case, if you’re the top, aim to delay his orgasm until fractionally after your own. This way, after you’ve come, you’ll still be hard and enjoying the afterglow inside him, which will help to intensify his orgasm, and he won’t find himself spent and ready to relax yet. Then, as the bottom comes, withdraw. Having your penis pull out of his anus during the seconds of orgasm should feel great.
Individual tastes will vary, but if you experiment you’ll find a way of coming together which doesn’t feel like a compromise for either you or your partner.