Anal Play with Little Buttercup


“Speaking of assholes,” my secretary said to me one day, eyes twinkling, when I’d finally finished complaining to her about some jerk at the office, “I’m getting increasingly curious about what it would be like to play with mine…”

She’s on top of me, riding me nice and slow like she likes to do. My naughty nymph, lying down on me with the side of her face on my chest and slowly sliding soaking wet pussy lips up and down the length of my thick cock. Damn I love the way my girl fucks. How many guys like me are lucky enough to have a little sex-starved teenage girl fuck them whenever they want? I’m the luckiest man on earth.

I have my hands on her bottom and I’m pulling her ass cheeks open and inching my fingers down, until an index finger finds her little anus. I just simply touch it, very gently. Tickle it.

“Did you clean your bottom, sweetie?” I ask her.

“I did,” my girl answers, looking up at me with a little smile. A nervous little smile. “Nice and clean.”

“Maybe we should take a little break from sex and I can give Little Miss Sloppy some kisses, and then do the same for her little friend?”

“OK,” my girl says, although she does not actually stop her slow and wonderful fucking. She looks up at me and smiles, a little nervous smile. “Does Little Miss Sloppy’s friend have a nickname, too?”

“Sure. Little Buttercup.”

“Little Buttercup?” She giggles, still sliding her pussy up and down my cock.

“Sweet Little Buttercup,” I say, gently tickling her anus.

“And you wanna kiss your Sweet Little Buttercup?”

“I do.”

“I’m feeling kind if shy.”

“I understand. I’ll take the lead, you just do what I say.”


Little Miss Sloppy is already gushing from our sex by the time I get my tongue on her. My girl’s wonderful taste is flowing out of her and within a few seconds my chin and cheeks are soaked with her fantastic sticky girl-come. Paradise.

Then I move down, licking the skin between her vagina and her anus. She may be feeling shy, but she lifts her legs and spreads them open and reaches down and spreads her cheeks, so that my tongue can find his little friend. His Sweet Little Buttercup.

I lick my girl, a nice big tongue-on-anus lick. She lets out a breathy little moan and I kiss her, I kiss my little secret friend. She is nice and clean and tastes sweet, although Little Miss Sloppy has gushed a fair amount of come and I’m tasting that wonderful taste, too, and oh my god I’m getting fucking turned on.

I lick and kiss a few times more, then sit back and put an index finger in my mouth to get it wet. I rub my wet finger around my girl’s anus a few times, pushing harder as I circle, until my finger is inside her, only up to the first knuckle. She’s tight, so damn tight, her anus clamping onto my finger, and I wonder, even if she lets me, whether or not I can actually get my cock in there.

And she’s warm. No, she’s hot. Oh, man, she’s so hot inside her. OK, that settles it, I’ve got to get my cock in there!

I circle my finger around, very gently and carefully stretching her sphincter. She gives a little moan as I move my other finger in as well, circling it around on the outside of her anus, then pushing it in, stretching her with both fingers now, pulling and circling and rubbing.

I look up at my girl; she is looking down at me, her face red.

“Will you let me have anal sex with you, Cee?” I ask.

She nods. No hesitation.

“I get to take your anal cherry,” I say to her.

She nods again, her face even redder.

“You’re a naughty girl, Cee.”

She gives a nervous smile. “I’m a little slut.”

“A little teenage anal sex slut.”

“That’s me!”

I circle and stretch her a little bit longer, then pull my fingers out. “Turn over now, shorty. Face down, booty up.”

My girl turns over and lifts herself up onto her knees. I take a bottle of lube and squirt a bit right on her anus. I work a finger into her warm little hole, circling, stretching her tight muscle, getting her ready to accept my manhood into her.

“Keep your muscle as loose as possible,” I whisper, squirting more lubricant on her anus and squirting a copious amount on my cockhead. Then I pull my finger out and press my blunt, thick cockhead against her tiny little pink sphincter.

I place my hands on her ass cheeks and my girl buries her head in the pillows, nervous about what’s going to happen. I move the fingers of both hands down until they are on either side of her anus and pull her open, stretching her anus open, at the same time pushing my cockhead in. I have to let go of her ass with one hand to grip my cock to provide a little more stability, but that’s all that it takes and I’m in.

My girl’s an anal virgin no more.

It’s quite something to see, especially from my vantage point behind her with both hands on her ass again. Her tiny little sphincter is stretched wide to accommodate my thick cock; my head’s inside her completely, her muscle clamping around my circumcision scar.

She is so warm. My head is in heaven inside my girl’s rectum.

I watch as I pull slowly back, the crown of my head passing out through her anus. She lets out a little moan, a sound of relief perhaps as her sphincter gets to close a bit with only the soft tip of my head inside her. But then I push back in, and she moans again as the muscle is forced to stretch open around my cock.

I pull back and push in, back, and in, my head passing in and out of her anus. This is what I like to do when I have anal sex; I like to give myself head with the girl’s anus. It’s an unbelievable feeling, the tight little sphincter clamping down on my head as I slide it in and out.

But eventually the heat of my girl’s rectum beacons me in, and I push deeper, half my cock now buried in her virgin asshole. I hold myself there and I move a finger down and begin to gently rub Sweet Little Buttercup, massaging the poor abused sphincter with my finger.

She moans, high-pitched and soft and sweet, as I rub her poor little asshole.

It is obvious why the man enjoys anal sex. It feels incredible, how wonderfully tight a girl’s anus is as it grips onto cock. And then of course there is the warmth. Add to these the dominating role that the man plays in the act, and it is obvious why he enjoys it.

But for the woman, I wonder sometimes why women enjoy it as much as they do. Part of the enjoyment must be the act of penetration. Women must necessarily enjoy being penetrated, it is their role, whether it is their mouth or their pussy or, new for my girl, their ass.

But I have also had it described to me by one lover as the ultimate act of anal fixation, in the classic Freudian sense. Freud, in his infinite strangeness, believed in various stages of “psycho-sexual development,” of which the anal stage was the second stage, where the anus becomes the primary erogenous zone (tied to “toilet training” at this age). Under this theory, women enjoy anal sex because it reverts them to a childish state in which the anus is the primary focus of enjoyment.

Indeed, even without anal sex, the anus is often stretched wide. As wide or even wider than it is during anal sex, but only for a few seconds. Most of the time we never think about this at all; we never think about whether or not we like the feeling–it might never even occur to us that it is something to be liked or disliked. According to Freud, however, there was a time during our sexual development when this was a feeling that gave us great erotic pleasure. And anal sex allows–forces?–the woman to return to that childish anal fixation and enjoy the feeling of having her anus stretched open.

That’s how it was explained to me once at least, and it is obvious to me that my girl is beginning to understand. I can tell, because she begins to tighten her sphincter muscle around my cock, squeezing, squeezing, in rhythm with my thrusts.

“Ohhhh,” she moans into the pillow, squeezing and squeezing.

“You likin’ this, Cee?” I ask, thrusting and thrusting.

“Ohhhhh, yeahhhh!” she moans, squeezing and squeezing. “Your cock is so big, David! So big!”

“Oh fuck Cee!”

“Oh David fuck my tiny little fuckhole with your great big penis!”

“Oh fuck Ceara I’m gonna come!”

My girl reaches between her legs and cradles my balls. “Come in me, David! Make me take it all!!!”

My legs are shaking hard as I slam into her all the way, her anus at the base of my cock now, my balls up against her pussy.

And I hold myself there as the first shot fires out, deep into her.

“Ohhhhhh!” I shout as I orgasm.

“Ohhhhhh,” she moans, feeling the hot wetness of come filling her.

I rear back and slam in again, and again, unloading.

When I pull out, my girl collapses onto the bed.

“Oh, fuck,” she says quietly.

“You OK?”

“That was… That was incredible.”

I give her a little peck on the cheek and go in the bathroom to clean up.