We’d been dating three or four months, keeping it deliberately casual. It was one of those classic opposites attract set-ups: I was older, she was younger; she was a medical student, I was an ex-punk rocker and construction worker turned nurse’s aide. I going to night school to become an RN, she was just about to start her residency. I was a bad boy doing my level best to straighten out, and she was a good girl experimenting with her naughty side.
It was, of course, not quite as simple as all that.
We had fun. We knew it wasn’t going to last, but we genuinely liked each other. And we did a lot of really excellent fucking in the meantime.
We got it on every time we got together, which was most days. It was good, old fashioned basic sex, ham-and-cheese sex; a lot of vigorous screwing with a little bit of sucking and licking thrown in now and then as an appetizer. Nothing kinky in the slightest. A couple times when we were fucking I’d slipped a finger between her ass cheeks and started playing with her butthole, and she had silently and firmly moved my hand away. I could take a hint.
She had a killer body. Slim and petite. Lithe, muscular legs that she ran half-marathons with and liked to wrap around my back while we fucked; flat tummy, exquisite little breasts. And an ass to die for, the kind of butt that I could have spent hours worshipping with my tongue. If only she’d let me. But I was sensible to leave well enough alone.
She sucked me off now and then; one time in a nearly empty movie theatre, and one week when she had a wicked yeast infection and couldn’t fuck, sometimes when she had her period, though mostly we just screwed anyway, mess be damned. I went down on her frequently: before sex, as an appetizer, or after sex if she wanted another orgasm; flicking her pink little clit with the tip of my tongue while she squirmed and sighed and melted on my face in the most satisfying way, but I always assiduously avoided the nether regions. Mostly we fucked. She loved to fuck, and she always, invariably came on my cock. We had dispensed with condoms early on, we were monogamous and I had a vasectomy, and I loved to feel her tight little pussy squeezing my cock as she orgasmed underneath me. Or on top of me, depending on the position. It was ham and cheese sex, but there was lots of it, and it was pretty damn good sex.
What she saw in a burned-out old punk rocker technically old enough to be her father I’ll never know. She was a nice girl, smart, and a horny little bunny rabbit; but to all appearances straight as a ruler. Appearances, however, can be deceiving.
We were lounging around in bed in my apartment, mostly naked, getting ready to get it on. It was mid-morning, I’d just come off a gruelling 12-hour night shift, and I was wired and tired. My dick was already half-hard, and her cute little boobies jiggled around like a pair of luscious peaches, juicy-ripe and ready to be plucked.
“What’s the deal with anal sex?” she asked me, straight out of the blue.
“What do you mean?”
“Why are guys so fascinated with it? Does it feel different? Have you ever done it?”
“I have done it before,” I said, “Once or twice. It feels a little different, I guess. But mostly I guess it’s hot because it’s kind of naughty, forbidden, risky-feeling. It’s very intimate,” I added.
I don’t know if she noticed, but my cock had sprung from half-hard to stiff and fully erect as I spoke.
“I think I’d like to try it,” she said. “With you.”
I started out by going down on her. It was always a pleasure to eat her pussy, and she certainly enjoyed it. Normally, I would aggressively lick her clit until she came, and then slide my cock up her wet pussy and fuck her to another orgasm; but this time I kept backing off each time she seemed to be getting anywhere close to a climax. I licked up and down her labia, teasing her clit, until she was wetter than wet, and my face was completely soaked in her slippery juices. Her cunt was wide open, lips swollen, clit straining. This whole time I had been purposefully avoiding my ultimate target, her crinkled little anus.
At a nudge from me, she rolled over onto her tummy, and I spread her delicious firm butt cheeks. It was the first time I’d had a good look at this part of her anatomy. Her butt hole was tiny, pink and tight. It was hard to believe something so small could open up enough to let a poop out, never mind accept a full-sized cock. I stuck my face into her cleft, tongue extended, and started licking, up and down, all around her anus, darting down to her drooling pussy, then back up to her asshole. She moaned, pressing back hard against me.
“Oh my God, that feels so good! I can’t believe we’ve never tried this before!” The tip of my tongue darted up against her sphincter, and I felt her straining back against me. Her own fingers were busy with her pussy, rubbing her own clit. I had never seen her masturbate before, and she got all shy and blushy whenever the topic was raised; she must have been turned on beyond belief at this point.
I decided to take it to the next level. Wetting a finger, first with my saliva, then with her joy juice, I circled her butthole, savoring the appreciative sounds she made as I tickled her anus. Gently, carefully, very slowly, I slipped the tip of my finger up inside. Her asshole clamped down on finger as the first knuckle slid past the tight ring of muscle.
“Ow! Ow! Stop! Take it out!” she squirmed away from me, pulling back in a panic. I removed the offending finger, and she clamped her hands over her butt, eyes squeeze shut.
“Sorry,” she said after a long minute. “I guess anal sex really isn’t for me.”
“It’s ok,” I said.
“Do you still want to fuck?”
I did. And we did. And when I shot off, she came right along with me, her whole body shaking as I squirted my semen deep inside her pussy. But it wasn’t without regrets, not on my part anyway.
“Tell me one of your fantasies,” she said.
We had been watching porn together all afternoon. I had turned her on to the stuff. She’d never looked at porn before, besides one or two giggling glances in high school or college with her girl friends; she was at least as surprised as me to discover she loved the stuff.
She had very specific taste. It had to be amature, no pro stuff at all; with attractive performers, but no surgically enhanced bodies. And she wanted to see them fucking: there had to be good, explicit close-up shots of penis sliding in and out of vagina. That is what turned her crank. We’d be watching together, and I’d slide my hand down her panties, and find her pussy all slippery, juicy and wet. We’d finger and pet and tease each other, and the invariably, we’d end up fucking in front of the computer monitor.
She admitted to me that she masturbated “once in awhile”, but she wouldn’t go into any more detail than that, and I didn’t press her.
“Go on,” she said, “Tell me a kinky fantasy. Don’t be shy.” On the screen, a couple was fucking, hard and fast, a bearded guy was screwing his big-breasted girlfriend from behind, making her tits swing like a pair of wrecking balls.
“Well,” I said, “I’ve always wanted to have a threesome….”
“I think,” she said, “that we could make that happen.” And then she slid her sweatpants and underwear down, and her pussy was glistening and ready underneath her fluffy little patch of blondish pubic hair, and we started fucking in sync with the couple on the screen, and that was that for a while.
After we were done, when we were cuddling, a sweaty and sticky mess, she turned to me, looking serious. “If I set up a hot threesome for you, with another girl,a super hot girl, one who really likes anal, would you do something for me?”
“Sure,” I said. “Anything.”
“Anything, for you.”
And that, in a nutshell, is how I ended up, a few days later, in bed with Elijah. His skin was the brown color of chocolate milk, and perfectly hairless, except for a hint of stubble on the cheeks and chin. We were both a little drunk, and naked to the waist. She was draped across my sofa, dicking around with the laptop, trying to find some appropriate porn. She was a little drunk too.
I don’t know where she found him. I don’t know how old he was, or what he did for a living; I couldn’t even get a vibe from him as to gay or straight or somewhere in between. He was cute though. She had good taste in men, I’ll give her that.
She finally found a video she liked, a cute, chubby tattooed redhead taking it vigorously in the pussy from her well-hung boyfriend. Me and Elijah started kissing.
I’d never kissed a man before, not seriously, and I have to admit I kind of liked it. His lips were rough, his tongue more aggressive than I was used to. I like the way he tasted, and the slight scratch of his stubble. I liked his hand on my chest, in my hair, stroking my cock through my pants. I liked feeling his hardness as well.
The pants came off. I was aware of her watching us, but I was much more aware of him, his body, his hands, his male parts. His cock, I was gratified, and slightly disappointed to discover, was smaller than mine. He was shaved or waxed clean, and circumcised, and hard as ice. Hot ice. We kissed and jerked off together, enjoying putting on a show, touching and caressing, pinching and stroking, each of us daring the other to take it just a little further.
By unspoken, mutual agreement, our hands found each other’s cock. It felt good, strange but good, to have another man’s erection in my hand. His grasp felt nice on my dick, softer and stronger than I would have expected. We kissed, letting our tongues dance and explore, as we slowly stroked each other. I glanced over at the couch, and she was staring intently at us, mouth slightly open, biting down on the tip of her tongue, blondish-red locks a beautiful mess, hand stuck down her own pants. The video on the laptop had come to an end, and she hadn’t bothered refreshing it.
Elijah and I were getting hotter and heavier, jerking each other off faster, more aggressively now. I cupped his tight little brown ass, pulling him closer to me. His breath was coming in raspy little jerks. It wouldn’t be much longer now, not for either one of us.
He came first. I was surprised by the force of it. His whole body went rigid, his back arching. He made a little squeak, surprisingly non-masculine, and I felt his cock pulsate in my fist. Then he sprayed hot semen all over my belly and chest. It was really gratifying.
I didn’t have much time to revel in it though, because as soon as his dick started to soften in my hand, he squirmed out of my grip, slid down my body, and did his God-damnedest to swallow my cock whole.
I was right on the edge as it was, and his hot mouth on my meat, his tongue swirling around my cock head, his wet finger pressing against my asshole was enough to set me off. Hips bucking, I came and came and came, and he stayed with me all the way, slurping me up and swallowing every drop of my come. She came at almost the same time, hand down her pants, head thrown back in ecstasy. Sometimes she was nearly silent when she came, but not this time. She sounded like an old time steam engine, huffing and puffing into the station, whistling and grimacing on overload, ready to explode. It was beautiful to watch, as Elijah and I took it all in, basking in the afterglow of our own orgasms. The evening hadn’t really been what I’d expected, and afterward I wasn’t really sure what to make of it, or how to process it. Weird, and maybe not something I’d choose to do again, but for all that it had been really hot.
Cherry was a big girl, large in every sense of the word. Big personality. Big breasts, big body, big curvy butt, brash and aggressive. She stood a full inch taller than me, and could have kicked my ass in a stand-up fight, no fooling. She was kind of gorgeous, in a very non-traditional and idiosyncratic way. When my girlfriend introduced us, she grinned at me like a hungry she-wolf, showing off two rows of perfect white teeth.
I led the way up to my apartment, the ladies following behind me, four flights up an echoey stairwell.
“You’re boyfriend has a cute little ass!”
“Doesn’t he though?”
“Ever gotten a rim job?” Cherry slapped my butt. “Boy, I am going to lick your asshole out until your head explodes.” My cock, which had been firm and flirting with hardness since we had met up was suddenly straining against my zipper.
No sooner had the door slammed behind us then the girls were all over me, tugging my pants and underwear down, pulling off my shirt, running their hands all over my body, kissing and nibbling and exploring. Cherry took the lead, with my girlfriend taking cues from her.
“Nice dick,” Cherry said, giving my girlfriend a sisterly squeeze. “Why don’t you show me how to suck it?”
My girlfriend got down on her knees, opened wide, and started slurping, closing her lips around the shaft and doing her damnedest to take the entire length of my cock into her hot, wet mouth.
Cherry winked lewdly at me. “That’s fucking hot. Are you ready to have your mind blown?”
She got down behind me, stuck her face between my butt cheeks, and started licking, circling my asshole with her tongue, darting inside, worming her way past my anus, only do dart back out and lick my balls while up front my own girl was slobbering all over my erection.
It was utter bliss, heaven, almost sensory overload. I seriously thought I might die of pleasure. I’m not sure how long this went on, but I enjoyed it while it lasted, two beautiful girls giving me kinky oral treatment from in front and behind. I was just starting to feel the beginnings of a come percolating up from my balls when Cherry stopped short.
“OK,” she said, leaving me gasping and panting, my wet cock straining up and out, purple with frustrated excitement. “That was a pretty good appetizer, but there needs to be some female nakedness right here and now. I need to have a look at those titties, girl!”
When we’d talked about doing this, my girl had said that she guessed she wouldn’t mind making out with another woman a little bit, if it would turn me on. There were no signs of hesitation as she attacked Cherry, pulling her tank top off and exposing her big bouncy breasts, fondling her as they French-kissed. She wiggled out of her own shirt and pants, letting Cherry’s hands rove over her body, eventually unsnapping her bra and setting her smaller firm breasts free. The nipples were hard and pink, and Cherry evidently took great pleasure in pinching and twisting them, harder than I had ever dared.
“YOU,” Cherry said, “Need to lick my pussy RIGHT NOW.” She unsnapped her jeans and peeled them off, exposing her voluptuous lower half, which was sexier than I would ever have thought possible. She wasn’t wearing panties. Her legs were thick and curvy, pale and smooth. Her pussy was tidily trimmed, fat lips pouting out, purple inner labia visibly wet. She lay down on my hardwood floor, spread her legs wide, and my girlfriend, who had never expressed the slightest interest in hot girl-on-girl action, dove right in.
Cherry parted her labia with two fingers, exposing her pink clit. “You know what I want,” she said. “Lick it. Lick it good!”
I watched while my sweet, innocent little girlfriend slurped her pussy, and Cherry narrated. “Oh my God, your girlfriend’s tongue is amazing! She’s licking my clit so good! …mmm yeah, just lick that. Put a finger inside. Yeah, more… play with my asshole… oh yeah don’t stop, keep licking, yeah, just lick that… holy shit, you’re going to make me come. Oh yes, don’t stop, please, yes, I’m going to fucking come all over your pretty little face.. oh fuck yes!!”
She didn’t stop. Cherry was writhing in ecstasy, kicking her ankles up in the air, a fistful of my girl’s reddish blonde hair, pulling her deeper into her cunt. She came, tits shaking, head thrown back, belly spasming, hollering loud enough to rattle windows.
My girlfriend finally came up for air, face wet and flushed and shiny, grinning from ear to ear.
“I need to get fucked now,” Cherry announced, rolling over onto her hands and knees. “You there,” she told me, “Pick a hole, any hole!” She leered back at me, prying her asscheeks apart, revealing a dripping wet pussy and the big brown star of her anus.
I pressed the head of my cock up against her asshole, which opened right up to envelop me. The muscles of her ass squeezed my cock tight, and once again I felt come bubbling up from my balls. I clenched my teeth and curled my toes, willing myself not to shoot off.
“Don’t come yet,” Cherry admonished me, “I want to enjoy this. Don’t even move. I’ll do all the work.” She tightened her asshole for emphasis, squeezing my dick with her internal muscles.
Cherry started sliding back and forth on my cock, sodomizing herself with my erection, deeper and deeper until I was buried completely in her ass, my pubes smashed against her ample buttocks. She’d rock forward until just the head of my cock was captured inside her asshole, then slide back, impaling herself once again. All the while, she was kissing my girlfriend open-mouthed, and playing with her cute little tits while she played with her own pussy.
“Oh yeah,” Cherry said, “That’s the shit! This is going to make me come… I want to feel you shoot off inside my asshole. Fuck my ass now boy, fuck it good and hard!”
And that is exactly what I did, grabbing hold of her big butt cheeks and pounding her ass hard. After all that willing myself not to come, I was surprised that I didn’t come right away, but I didn’t. I could feel the orgasm building though, and it was not far off.
While I was fucking Cherry’s ass, concentrating on my own pleasure, my sweet girlfriend was getting some pleasure of her own. Cherry, grunting throatily every time I humped forward, had her panties pulled halfway off, and was licking at her clit, fucking her pussy deeply with two fingers, another two fingers crammed deep up her ass, all the way up to the knuckles. It’s an image I’ve jerked off to many times since then.
I can’t swear to it, but I think we all came at the same time. My own orgasm, when it finally broke through, seemed to go on and on, rising through me like a tsunami, overwhelming waves of pleasure wracking my body as I pumped my semen deep into Cherry’s hot ass. Cherry was coming like an overheated steam engine underneath me, and I could hear the familiar high-pitched cries of my girlfriend’s orgasm as Cherry finger-fucked her pussy and ass.
I never did get to fuck her in the ass. She did mine, one time, sliding a long wet index finger up my asshole while she sucked me off, a few nights after our threesome with Cherry. It was exquisite, and I think she was gratified with how thoroughly it got me off, shooting with a cry into her hungry mouth as she wiggled her finger deep inside my body.
I also feel like that night was the beginning of the end for us. I’m not sure why, maybe I had just served my purpose with her.
We broke up not long after that. It was pretty adult, not too many hurt feelings, no yelling or screaming, just two people who weren’t going to make it in the long run. I heard that she and Cherry started dating, and I’ve thought about looking the two of them up sometime, but so far I haven’t. Maybe I should. I don’t know. Sometimes it’s best to leave good memories alone.