Message: What Happened to My Stamina?

Asstronaut: I have currently been with my girlfriend for 6 years. At the beginning of our relationship we had one amazing anal experience(her first) she had an orgasm so intense she said her toes went numb…. The sounds she made…. On the other side of the coin, I had purchased her a tail plug which caused her a lot of pain. Long story short, after seeing that I had hurt her I didn’t ask again until last month. She is very receptive… But it’s been so long(almost 6 years)and her ass feels better than anything I’ve ever experienced in MY LIFE that I can not last any longer than it takes to get the head of my cock past her inner ring. The moment that I’m inside of her I cum….. Stamina is only an issue when we have anal. Any ideas?

I’ll start by saying that while anal certainly shouldn’t hurt and definitely doesn’t have to, encountering a painful experience once doesn’t mean you should just end it altogether. Pain means someone simply isn’t warmed up enough or prepared for what they’re doing, or the plug in question may have been an uncomfortable shape for her. Going forward, if there’s pain I’d say to stop and reassess in the moment but not give up on anal entirely.

Getting to your question, however, I suspect that it’s a combination of extreme tightness for her and your excitement about getting anal again. That excitement is understandable, and there’s not too much you can do about that, but the tightness you can work on together with some anal training and helping her better relax and open up for you. If it’s taking effort to get inside her, she could probably stand to have some more training and warmup before sex to help her relax.

If it really is just that it feels so much intensely better than anything else you’ve ever done, you may need to practice more to build up that stamina, which can mean more regular anal sex. Perhaps start with a lot of anal play for her and get her close to the edge, then switch out for yourself and finish there while getting her off at the same time, and over time work to last longer.

See also this past answer to a similar question: How to Last Longer With Anal

Perhaps some other readers could offer their suggestions as well.

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