So it turns out that when you separate me and Tim for three weeks and we don't get to have sex, when we come back together we do EVERYTHING. In our first 24 hours together we've had sex five times and knocked a whole litany of things off of the List. This afternoon we did a schoolgirl roleplay where I was the good little Catholic girl and he was the dirty headmaster. I told him I was a virgin and he accused me of touching the other girls. It was so wicked and cute at the same time.
My hopes for the evening were pretty specific. Tim is pretty touchy about taking anything up the ass, but it's one of those things that I find incredibly hot. He's pretty much always worried about poop, which I suppose is a valid fear, but today he agreed to let me use some anal beads on him. I think that purchasing him a black face-mounted dildo clinched the deal. (Oh, kinky Christmas gifts...)
After we got back from our sex shop run, after a lot of getting up, going to the bathroom, sitting back down, getting up and getting water, and every other distraction I could think of, I got him naked and curled up behind him under the blankets with my arms around his waist. I got out some anal beads we'd bought a while ago and never used.
"You want to do it like this?" I asked him.
"Yeah," he said. Tentative, nervous. I like that.
I spread his ass cheeks and pushed the first bead inside. This convulsive shiver went through him and I stroked his back, told him how good he was. Then I reached down and did another, and another.
"Stop there for now," he said. He had that tone in his voice that he uses when he's feeling submissive, soft and gentle and sweet. It makes me want to do awful things to him.
I wrapped one arm back around his waist and grabbed his cock with the other. He was rock hard, which normally doesn't happen when I play with his ass.
"Oh my god," I said. "You like this, don't you? You little slut."
"Yes, ma'am," he said. He was gasping; I've never seen anything like it. "Yes, yes. Your little whore."
"Can you take more?"
"I think so."
I slid the next three beads in, and he groaned and rubbed his ass up against me. It turned me on to see him thrashing, grinding, begging, filled up.
I flipped him over and he tried to jerk off but I slapped his hand away.
"No," I said. "I want to fuck you."
"Oh, please," he said. "Please fuck me."
Where's a condom when you need one? I fished around in the sex box and finally came out with one, ripped open the packaging, and unrolled it onto his cock while he thrust his hips up and down. I pulled up my skirt and slid myself down onto him. I hadn't realized until then how wet I was.
Now, in order to fully appreciate what happened next, you should know that while Tim is a brave man, he's been very hesitant about his ass, especially my ultimate hope for it: fucking it with a strap-on--and more than that, he doesn't usually like the idea of gender play. So what happened next was pretty extraordinary.
"Oh, God!" He thrust up into me from underneath. "Oh god, oh--we're going to buy you a strap-on, and you're going to fuck me in the ass, and I'm going to suck your big cock!"
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