Anal Playtime

Carrie was a high-spirited, competitive kind of a girl. I had seen her plenty of times running for victory across the lacrosse field in high-school, had teamed up against and with her for those late night “Scrabble” marathons at the shore house our parents shared and had compared grades with her in college even though we had both studied for different majors. Along the way of course we had done the ‘booty call’ thing (if they even still call it that these days) and I seriously thought she kept coming back cause I could keep up with her insatiable sexual appetite. She’d visit me late nights after being out with her latest date, which hadn’t even come close to satisfying her sexual needs, and more often than not Carrie’d want something kinky…and more often than not I was into it. Her big brown eyes would get wild and even wider, I’d add a wrinkle to a suggestion and off we’d go.

Like me, Carrie was a bisexual woman. We spoke about the men we dated (this aspect of our life we never compared) but she, nor I, had ever introduced or spoke about a strap-on. I guess we were both getting enough dick we didn’t need or want a fake one, but Carrie “was” into penetration with me…anal penetration. On the few occasions the petite blonde had mentioned anal sex with men, she said it hadn’t been the thing for her. Sure, sometimes she’d get into it-Carrie really was sexual so almost anything could turn her on-but like me, the times she let a guy take her ass had been few and far between. But between us girls…well that was a different matter.

Carrie had lubed up her fingers and spread my cheeks, I had licked her sweet little starfish to drive her wild, but when it came to anything ‘back there’ Carrie ‘took’ more often than not. I mentioned she was wildy sexual and competitive, but man, she became as gentle as a lamb, almost submissive, for ass play.

“I need you to try this,” Carrie said, after she had knocked, come down the flight of stairs to my studio apartment, plucked the two items from her bag and began to strip. I was used to her whirlwind entrances, and I loved to see Carrie naked, but this was unprecedented.

“Interesting,” I said holding out the thin dildo she handed me.

“Made just for lesbians,” she informed me, out of her bra and kicking her sneakers off.

“Are there any lesbians here?” I joked.

“You know what I mean.”

I did. The thing I held was a woman’s sex toy, made mainly for two girls to use on one another (though how you could really make a distinction between gay or straight in anal sex play, I had no idea). I guessed that those huge dildos I had seen or those fat fake cocks could scare someone, especially when it came to putting one up your ass. And indeed this toy in my hand (the other thing Carrie had given me was a new bottle of lube) seemed softer and gentler somehow.

“This is thin but it looks like it’s gonna go deep,” I said, squirting more lube down the toy.

“Definitely,” Carrie said. Completely naked then, she walked up to me, kissed me hard on the mouth then got down on all fours.

“You really are all about the romance, huh?” I snickered and went back to lubing her new toy.
“Jesus Kim, Mark got me all hot like he always does,” Carrie explained under me, wiggling her fine little ass, opening her thin thighs as she spoke. I really was torn with continuing doing what I was doing and getting down there on the floor with her.

“Tonight I was trying to angle myself across him, give him my ass, back up to him, ya know? And all he does is finger me. I just wanted a little swat while he did that, ya know, but he never gets it. I send him all these signals but he never gets it!”

“You should just tell him what you want,” I said, really glopping lube down the long little toy.

“And not come over here for a good ramming? Never!” she said, looking up at me.

Carrie really did look so sweet there on all fours looking back and up at me. Who was I to deny her her deepest wish? I knew I’d get her ass filled, she’d start to quiver and mew and I’d be able to angle myself in front of her. She’d be into licking my pussy like she always did-and Carrie could lick pussy like a pro-and we’d come over and over as I plied her ass deeper and she’d clutch and surrender to me.

I guess, in some ways, we all fulfill a purpose for our lovers, sometimes it can be all encompassing and sometimes it’s only a certain aspect of their desire we speak to; lesbian, straight, bi, it doesn’t matter.

The anal toy was as wet as I was gonna get it without it slipping out of my hands and I got down on my knees as Carrie smiled even wider.

The snap of the glove made Mary’s eyes fill with tears.

Stan stood behind her as she pressed up against the high wooden edge of the bed, her bare back arched, her legs spread and teetering on three-inch heels, her hands behind her spreading her cheeks as far as she could. So far the only sound had been the quick “Squiq a’squip” of Stan’s repeated application of lubricant on the bare fingers of his right hand, the moaning they both made as he had lubricated her pruned anus and then the retort of Stan snapping on the glove to his left hand.

Mary had been shaking when Stan had kissed her on entering his apartment and told her what he had planned, quivering when he stripped and bathed her, shaking fully as he walked her to stand naked against the bed’s edge, mewing as he bade her pull her cheeks apart, clutching when he applied the lube to her ass and now crying with the realization that, with the glove on, Stan was about to ply her asshole.

Of course Mary wanted nothing more in all the world for her boyfriend to finger-fuck her ass, in fact she was opening up as much as she could right then to prove to Stan that she could eventually take his cock up her. Sure, she knew they had to start small, with Stan’s finger, maybe two. Then, if all went well, Mary’d ask for a toy or two, something thin maybe, but strong, a toy made specifically for ass play; maybe even a plug, dildo beads…or all three!

Mary fantasized about it all.

Was anal like the classic pot to heroin conundrum? Did you take something small and thin at first, like Stan’s finger, then ache for something bigger eventually, say a giant thumpingly thick dildo to spread you ’til you ached? Christ, Mary nearly swooned then as she imagined it!

But was it really size, the big blonde wondered as she lean there and waited. What had Mary really want, beyond the fact that she was leaning and presenting her virgin starfish to this guy she had only known three months (Jesus, did she really want an ass fucking so much that she’d let Stan do this so early into their relationship?) was that Stan was so fucking confident. Mary needed, ached, fantasized about a guy like Stan, a guy who would simply know what she needed, not second-guess her decision or constantly ask her: “Are you sure? Are You sure?” A man who simply would bring the glove and lubricant he needed, tell her this night was the night, bathe her, dry her, and then get her standing ready and willing to do what she had wanted to do for so long but had never tried.

That Stan was methodically moving forward to the obvious conclusion of putting his finger or fingers up her ass now, that he had yet to say a word really after he bathed her, that he was breathing lightly, hadn’t made a move to touch her anywhere else, nor turned her, or stepped to the side to even look at her, got Mary all that more turned-on, all that more assured, all that more submissive to this act of anal sex. Though she had masturbated to just this scenario many times she had never realized how sweetly erotic the entire escapade would be when she finally got the chance to experience it.

“Hurmp,” Mary said as Stan suddenly clutched up to her. He had hold of her left cheek vertically, spreading it even more as he snaked his covered cool wet fingers deep into her ass.

Mary smacked her pussy against the hard wooden edge of the bed and felt her stomach clutch. Shit, was she gonna come this quick?

“Open,” was all Stan said and Mary pulled with her right hand, spread that cheek for Stan and his fingers spider-ed into her, his middle finger stretching, deep and true.

Tears started to stream down Mary’s pretty pale face when the tip of Stan’s middle finger tickled her hole. Weeping fully then, Mary lost her reason as Stan fed his long lubed finger into Mary’s ass, up to the first knuckle. As she came and cried Mary looked back at Stan who looked up to her and smiled.

“You are never going to be the same,” he said and pushed in deeper.

Mary bit back a yelp, rolled up on her tip toes and knew, deeper then she had ever known anything about herself, that indeed she would never be the same.

Nor did she damn well want to be.

“Mark, you’re shaking,” my best friend exclaimed from over and behind me.

If the sensation of my cock and balls pushed up against Vanessa’s bare thighs wasn’t enough; my quivering ass high on her side-by-side knees, sweetly embarrassing; hearing only her voice, not being able to see her topless over me was maddening, the anal probe she was pushing deep up into me was causing me to gulp for air.

Staring at Vanessa’s three-inch pumps before me I held onto her ankle as she continued to ply me with this anal sex toy she said was called a prostate massager.

“This is really wild,” Vanessa said.

“Ya think?” I hurmphed.

The thing in my ass felt big, thick, huge with a capital HUGE, but really I knew the toy to be more long and skinny-sure bent at the head-but really not as big as it felt up my ass. I guess it was simply that it hit the right spots that made me clutch there, whimper…and try to pump my cock against Vanessa’s warm bare thighs.

“You’re clutching, open up honey, open up,” she requested and I sighed and spread my ass as far as I could while staying balance there.

“Ohh…yeah,” my girlfriend said as she pushed the toy further up my ass and I felt my balls tighten.

“Va..va…va,” I quickly wailed, pumping down into her lap three times.

“Hold on, hold on,” she said, one hand spreading my right cheek the other tried and true on the anal probe. “Hold on, don’t come yet, wait ‘til I get this up the…”

“AH HA,” I yelled and bucked as Vanessa threaded the thick toy up me to the hilt. She managed to twist it just enough where she definitely came in contact with my prostate and a cold shiver ran up my spin.

“Ahh, very, very nice,” she said, settling, letting the pressure of intrusion ease off for the maddening tickle of the head of the thing doing its job up my anus.

Vanessa doesn’t usually make a move, whether it’s playing with a sex toy or baking a cake without making sure she has read and understood directions. For this, our latest adventure into kink, she has ready plenty about prostate massager and how a toy such as the one she had up my ass then, could bring about extreme results.
“Next time I wanna see you take something really big up here,” she said working the massager’s head forward inside me. I felt a quiver in my cock like I have never felt before. I felt like I was both going to spill and shoot at the same time.

“Vaa…vaaa,” I spat, moving across her, feeling her bare belly against my side then rolling away to the edge of her knees. She kept me in place with what she was a doing back there and I again felt such a strange sensation of being so full and wanting to leak right down across her.
My balls were on fire.

“It’s just that your ass is opening so well,” she said, pushing. I could have sworn come was flowing out of the head of my cock in a steady stream; I began to shake. “I mean why not try a bigger toy, right?”

I couldn’t answer her. I was quivering, clutching, pumping, sweating. I was going to come, spill, let loose in a way I had never done before, all with my cock pressed up like that tight under me, against the fold between her thighs. Sure getting me across her lap was good for anal exploration, but really, could I come this way?

“Ok, hold it here, hold it,” Vanessa said, leaning back. I felt pressure ease up from her pushing the toy up my ass. “Get up slow, but keep it up there, okay?”

I did as she asked, walking more with my hands about before me than actually standing to face her. I was bent half way and turned to her, the tip of my cock kinda lying on her knee as I squatted there facing her.

I had managed to keep my little anal friend in.

“Here,” Vanessa said reaching around me as her knees brushed my balls. I settled my gaze on her massive rack, faced her popping pink nipples and she began to manipulate the massager again with her hand around my ass.

“Come on my legs,” she said as I looked up at her for a second before lighting my eye on her tits again.

“Spill every last drop, I want it all.”

I didn’t have to move, didn’t even have to squat any further. I simply bent there with the purpling head of my dick on her knee cap, Vanessa pushed twisted and fed her new toy up me and I began to come.
And come.
And come.