Ready for An Overnighter

My wife and I both enjoy extended anal sex. One of our favorite things to do is to put an X-rated movie in the VCR, lube up, hook up, and watch the whole thing start to finish. I usually cum at least once, regularly more than once. A couple of times lately, one or the other of us has fallen asleep before the movie ends. Not wanting to wake the sleeping one, whoever’s awake just hits the power button on the remote and takes a nap. When the sleepyhead wakes up after an hour or so, we separate, shower, and go to bed.

We’ve been fantasizing about just staying “connected” until it’s time to get up the next morning. I don’t seem to have any problem with a priaprism (prolonged sustained erection), as her anus is fairly relaxed the whole time. My cock goes from nearly flaccid to nicely erect once every ten minutes or so while we’re connected, reportedly even when I’m the one asleep. We both like deep anal penetration, and keeping my cock in all the way to the base probably also has something to do with good blood flow out.

So, should we go ahead and spend the night locked in an anal embrace? We’ve tried this vaginally, but the lack of a sphincter muscle means that when I go limp I fall out. Her anal sphincter, and the vacuum effect of such a tight seal seems to be just enough to prevent that from happening during extended anal sex. Also, we’ve found a position (spooned, with both my legs wrapped around her bottom leg — impossible on anything but a waterbed), that keeps the penetration deep enough to help hold me in.

–Ready for An Overnighter

I must commend you on one of the most creative letters this Anal Advisor has ever received! It sounds like you’ve already experimented with staying inside her ass during short naps, and it’s worked pretty well. It sounds like you are blessed with the ability to go from soft to hard fairly easily, which definitely makes the situation easier. I am impressed that neither one of you moves during these naps, which would certainly break the connection.

As for trying this for an entire night of sleep, I am not so sure it’s a good idea. First, surely one or both of you will shift during the night, which could result in an awkward position or worse, you could hurt the other. Second, I can’t imagine that for several hours you’ll be able to maintain an erection (even for ten minutes at a time), which will make prolonged penetration very difficult. Third, if you did achieve the kind of “vacuum,” as you called it, the risk of cutting off or decreasing the circulation in your cock is too great. Hey, you’ve made these catnaps work, which is more than most people can do, so I say, keep having those short, fun encounters and don’t be greedy!