His fingers, the tip of my pinkie

We set up the Liberator Ramp and Wedge on the bed, then draped the Throw over it. It was a luxurious black mess, a satin throne for me to sprawl upon. I spread my legs and lay back, into the comfortable and firm foam. After a bit of oral — sweetening me up with watermelon-flavored lube — he began fingering me. It was high time he witness me squirt, and he wanted coax it out of me with his fingers.

I’ve never been one for fingering. Not once have I fingered myself for masturbatory purposes, so I don’t crave it from him most of the time. But this time, laid out and helpless before him, I wanted to be finger-fucked. Hard. And I wanted to come.

He kept asking if he was doing it right, as if my facial expressions didn’t make it apparent — he was doing it perfectly. But G-spot stimulation causes a different reaction in me. I get lost in it. I become almost comatose with pleasure. I could feel my orgasm on the horizon. I grasped fistfuls of the Throw. “Faster,” I said. He started sweating. “As fast as you can,” I begged. He tried. I came so close, but he couldn’t move his fingers fast enough.

I had the Ella waiting beside me, so I picked it up, slid the G-spot end into my vagina, and fucked myself as hard as I could. I came quickly, hard, feeling the come coat the dildo and soak into the satin under my ass.

I looked up at him. I was hoping his face would read “OMFG,” but alas, he said he couldn’t really see my come. My come doesn’t spurt out, it just sort-of dribbles. I think the strange contortions of my face are probably more interesting to watch than my vagina. Nonetheless, I felt like being a show-off, so I asked, “want me to do it again?” and proceeded to make myself come a second time. He was impressed.

But that wasn’t the only accomplishment of the night. On the same night, out of the blue, my boyfriend asked me to touch his asshole. Both of us know that he has a serious aversion to even the thought of buttplay (for physical reasons), but he also knows that I would love to one day be able to fuck him. So when he brought it up, I wasted no time in bending him over the Ramp/Wedge, putting a condom and lube on my pinkie, and very lightly teasing him.

It was worse than I thought it would be. He would not stop clenching. In fact, he would twitch whenever my finger began brushing his skin again. I promised him, over and over, that I was not going to do anything without telling him first. But he could not relax. Not even for a few seconds. It was disheartening and strange for me to witness. He regards his asshole as a foreign area separate from the rest of his body. He has never, ever touched it, and he has always thought of it as a dirty place meant only for poop. It is very hard to change someone’s mindset when it comes to this, even if he wants to change his mind.

After much time, I was able to insert the tip — just the very tip — of my pinkie into his ass. It was not easy, but we did it. And both of us feel that we have made some progress. It is likely going to take a long, long time before he is comfortable with buttplay. Unfortunately for me, the experience of finally touching his asshole for the first time only served to remind me of how much I want to play with his ass on a regular basis. I must restrain myself.