Never

The other night, I don’t know, we’ve been fooling around so much this holiday week that I’m having trouble keeping track but I’m pretty sure it was Thursday night, it was getting to the end of the night, it seemed.

It was a night that we had planned ahead to be careful around our back doors, because she’s run out of the antibiotic, cephalexin, that she takes as a prophylactic against UTIs. It was on auto-renewal for a while so we had a lot piled up because even we don’t fuck 30 nights a month, but then of course we turned off the auto-renew and months later weren’t paying attention when it ran out. (As a reminder because who knows how long it’s been since I talked about this, she tends to get UTIs pretty easily and those mainly come from touching the front after touching the back). I reminded her about it and then said “I’ll stay away from there” at the very same time she said “be careful.”

Well, I don’t really trust myself to be careful when I’m high and in the kind of completely turned-on state that causes some people to, you know, come inside despite lacking protection and risking unintended pregnancy. Which I have never done, by the way. So despite her permission, I decided to stay away from there.

Except it’s really hard to stick to those decisions. So, like I said, it was getting to the end of the night and I was beside her, on her right with her on her back, using both hands. Left hand pinching her clit, right hand massaging, thrusting, etc. I looked in for a closeup and her little ass cheeks looked so cute that I had to slide back there and tease her a bit … I didn’t touch anywhere risky I thought, but she flinched a little, and out of caution I pulled my hand away. She said “it’s OK, you can touch there” and I realized the flinch was actually a shiver of surprised pleasure. I lubed up my right hand with silicone and started into her ass with my middle finger.

She pretty much always likes the the tickling around the outside, and when I put a finger just a little way in. If she wants more, I can tell from her body language, and she was moaning and cooing and squeezing my finger with her ass, so I went to town … thrusting deeply, gyrating it around and stretching the muscles to get them to relax. As soon as I could tell it was safe, I added my index finger and then my ring finger. Squeezed into a triangular arrangement, they’re thinner than my dick at the tip, but thicker as I push in, and I can spin them a little to stretch all sides of her with the longer dimension at their bases.

If I take too long, she gets worn out or desensitized or something; on the other hand, I can’t go too fast; assholes need to be stretched out and warmed up if you’re going to put anything big in there. This time it was working perfectly–she was really into it and I was ready. In her ear I whispered “let’s get that tight little ass ready for my cock” and she smiled sluttily. I grabbed the silicone lube (Wet Platinum) and dosed my cock liberally. There are two keys to anal, as far as I can tell, and they are 1) stretch out that ass first 2) use gobs and gobs of lube. She said something about “this way you won’t fall out and hit a bad place,” meaning that if my cock slipped out, it wouldn’t fall on her pussy (because she was on her back). I didn’t say anything; fucking her ass from the front is usually better anyway, because I can see her face and understand what she’s liking or not.

This time, she liked it a lot. Damn, her ass is nice, and I was fucking it excellently. My cock big and hard, I worked her at a few different depths with short thrusts, and when it was clear she was ready, took her deep. OMG. At first she was rubbing her clit and she came over and over for the first couple minutes. She moved her hand away, and I pinched it with my left hand for a few more. Then she waved me off and just enjoyed the fucking. But like I said, it had been getting to the end of the night, I thought. This can be tricky; I don’t want to wear her out before I finish but neither do I want to come too early and deprive her of more orgasms. So I said “let me know when you’re ready for me to stop” and she replied “never.”

Do you know how awesome it is to have a hot, hot wife, and you’re fucking her perfect little tight asshole between her perfect little round ass cheeks while looking down at her beautiful face and her perfect little pussy and her perfect tits, and she wants it never to end? I cracked a huge smile and pounded away at my little slave (oh–somewhere not long before all this we had a really good punishment/discipline session and she was still feeling thoroughly submissive) for a couple more minutes. Twice she lurched in orgasm, putting her hand over her mouth to stifle the squeals. Finally I couldn’t handle it anymore and asked “are you ready for my cum?” She looked right into my eyes and said “give it to me.” I started the rhythmic hard thrusting that leads to the inevitable conclusion and exploded in her tight ass. Holy shit, I went into outer space–no, I was outside of time for a few moments. I pumped that little ass full of my cum and as my dick softened, pulled it out and rolled away to enjoy a moment or two of afterglow. Before too long I cleaned us up a little and went to the bathroom to wash up.