My ass had been private territory until I met Francine.
She had conquered all of my body by our first month together. All of it, of course, except for the space between my lower cheeks, the sensitive spot her hand sometimes grazed as we made out, naked, on her futon. Or on my teeny little bed. Or on her couch. Or on my kitchen floor. Almost every surface in our homes had been conquered by then, by…well, by our lust.
We’d even done it in public once, one hot summer night. She went down on me while I lay on a blanket on the sand, the waves washing over the beach as the orgasms washed over my body. For once, I didn’t try to find the constellations I knew by heart, instead letting my eyes flutter open and shut as I bit back moan after moan, gasp after gasp. She had come up for air after a few minutes, and I watched her as she smiled at me, and she watched me trying to catch my breath.
“Good job, Fran, you made me come for days just then.” I’d patted her on the cheek, and she’d laughed, and then I’d grabbed her and pulled her up, up to my lips, and onto them, for many, many well-deserved kisses.
But it was in our fifth month when she suggested we try something new, something which involved some very unexplored territory.
We were both on her couch, me on my back, and we’d been making out for an entire episode of some trashy lesbian reality show. “Really? I…I don’t know, sweetie,” I told her, staring into her bright green eyes. Her bright green, expectant eyes, their expectant stare now joined by a slight, subtle smile.
“It’s just that I’ve wanted to try it, ever since I saw it in this one porno, one I watched while you were in Mexico after we’d been together a month or so. It was so fucking hot, you know. Just amazing. I watched it again and again, and then I shut it off and pictured us doing it instead.” Francine brushed some hair off of my forehead, then leaned in to kiss me again. But I stopped her, pushing her up a little, and asked, “What kind of…anal stuff were they doing? Was it like, strap-on anal stuff? Or was the woman licking the other woman’s ass?” I wanted to know exactly how far my girlfriend wanted to go with me, exactly how far she wanted me to go.
“It doesn’t matter what it was, really, does it?”
“No, no, I guess not. What matters is what you want to do with…or, actually, to me.”
Now I was the one with the expectant expression, staring up at her and waiting for her to tell me what she was picturing us doing.
“How about we start with just a finger?”
“Or two,” I joked, but Francine looked very serious as I said this, and she didn’t laugh.
“Let’s go into the bedroom,” she said. “That’s where the lube is, and I know we’ll need some.”
“I suppose we will.”
Francine got off of me and stood up, and I pushed myself up off my back, slowly getting to my feet. I was nervous, of course I was, but I was a little bit curious, too. What did a finger feel like, back there? Did it feel…or would it feel good? There had been a few surprises in our sex life before, like how easy it had been for her to get her entire hand inside me, and how I’d gushed after a number of well-positioned thrusts of her wrist, her fingers pushing hard against my newly discovered g-spot. We’d each only been with one other person, and so much of this–so much about sex, and so much about relationships–was brand new to both of us.
So was this, so was getting ready to explore anal sex for the very first time. And I was definitely nervous, but by the time we got to the bedroom and Francine reached for the lube, I was ready, too.
“Go slow, OK?” she said, and Francine got onto her back, spreading her legs.
“I’m…you’re…I thought you wanted to do it to me,” I said to her, and I grinned at the surprise. A few giggles escaped my lips, and Francine laughed, too.
“You can go next, if you want, but it was me I was picturing getting penetrated.”
“Sounds fine to me,” I told her, the silly grin still on my face. Francine handed me the bottle, and I squirted out a little lube, then told her to lift her feet off the bed and to grab the backs of her thighs. She did this, and I had the clearest view of her asshole I’d ever had–the clearest view of anyone’s asshole I’d ever had. I got onto my hands and knees and placed my free hand on the bed, then began to reach out the other.
“Are you ready?”
“Yep.” I figured she was ready, at least mostly, but her voice still shook a little as she answered me.
“OK, I’m going to do it now,” I told her, and I placed my middle finger, the one with lube on it, up against her asshole. I started by rubbing it a little, flicking my finger against it. And fuck, touching her there was really, really turning me on. I felt my cunt grow wet, much wetter than it had been when I was still on the couch, and I watched Francine’s get more flushed, more aroused, too, each of us getting wetter the more I touched and teased her ass.
Then I started to push in–slowly, of course–and she grunted above me as I did, a deep, sudden sound of pleasure. So I slid my finger in deeper, halfway in now, and then she shook a little. “You like this, don’t you?”
“Yes, yes, I do. I do!”
I took that as a suggestion to put the finger in the rest of the way, pushing it in until the whole thing was gripped tight by her ass. “Play with yourself,” I told her. “Play with yourself while I fuck your ass with my finger.”
She placed a few fingers on her clit, beginning to rub the lower left side of it–her favorite part of it, I had learned by now. And I began to fuck her ass with my finger as she did, matching each flick of hers with a thrust from mine, both of us going faster and faster until she gasped and began to shudder, and I watched my girl come harder than she had in months.
“Your turn, now,” Francine said as she let go of her thighs and began to sit up.
“You mean to be…?”
“Yes, if you want to. I can recommend it highly, now. Very highly.”
“I think I’m up for it.”
It only took five days more for both of us to work up to the strap-on. And only one day after that before I suggested we try the bigger dildo. You know, to see if I could take it.
And fuck, could I ever.