Being Prepared.

I visited Judith on Thursday night. We went out for dinner (which is unusual), then back to her place. I've always had in the back of my mind that anal sex is a possibility with her. She'd never done it before, but quite liked having a finger in there when she was nicely aroused (and sometimes requested it), and I'd made no secret all along of the fact that it was on my agenda.

So Thursday night, we had sex. Vanilla, but as always with Judith, very satisfying. Afterwards we were lying in her bed, cuddling, she facing away, me behind her. I love that. I find women's backs very erotic (actually, I find pretty much everything about women erotic, now that I think about it.)

"Kiss my back", she said, and I did. I started kissing her on her upper back, her shoulder blades. She was still pretty excited from the fucking, and I noticed that kissing her back seemed to really turn her on. I continued, naturally, and I started getting more and more aroused. I moved down, kissing and teasing her flanks and lower back... same effect, but more. By this stage, as you can probably guess, I was starting to form a plan.

I ran my tongue down between her buttocks and she made a sound that I hadn't heard before from her; lower, more intense. I kept going.. I rimmed her (which we'd already established she loves) and played with her pussy, and then she said:

"I've never felt like this before..."

I stopped what I was doing for a moment, put my head next to hers and whispered in her ear "I'd really like to fuck you there...". She said "I've never done that before..?", which of course I knew, but said it in a way that suggested that she thought this condition of never-having-doneness was looking a bit shaky.

I thought for a second, sat up and asked her "do you have any lube?". She shook her head.

I did. In my jacket (as I've recreated in the pic above, for dramatic effect). And for a split-second I was torn. What sort of message did it send, that I had secretly brought a tube of lube with me? Would she be angry or upset? But if I didn't get that lube right then and there, I might never have an opportunity this good.. if I chickened out now, would I always remember this as The One That Got Away?

I said "hang on a sec.." and went to rummage around on the floor, looking for my coat. I got the tube of lube out and went back to the bed. Then, while I was playing with her pussy with one hand, I somehow managed (and it's amazing what you can do when you really have to) to open the tube of lube, realise the safety seal was still on it, unscrew the cap, remove the seal and then screw the cap back on all with one hand. And in near-darkness. She knew I was up to something. "what have you got there?". I squeezed some lube on my finger, "this might be a bit cold", I said.

So I fucked her in the ass. I was, as always, very gentle (I didn't remind her, although I could have, that in my former life as a gay man I've been fucked many many times, so I do know what I'm doing).

Afterwards she asked me about the lube. Had I just brought it this time, or did I have it in my jacket all the other times I'd been over to her place? Good question, I thought. I told her I had always had it with me, just in case..

She called me yesterday to see if I wanted to hook up again last night. I like that - it means I must be doing something right.