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A is for Anal

Category: Anal Sex
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Jackie had always considered herself an open-minded fairly uninhibited woman. At five foot nine, she could have easily gone into modeling, with both a face as well as a shape for doing just that. Long auburn hair falling well past her shoulders, aqua blue eyes that looked sometimes green if she happened to wear that particular color, and full sensual lips that more than one person had actually commented on.

Jackie felt her long shapely legs and ass her best features however, though her small perky breasts held enough allure that whenever she’d worn one of her more revealing bikinis, she’d received enough appreciative glances at them to make her smile, though demurely so, whenever she passed by anyone blatantly looking at them.

She worked in a small boutique close to her apartment. Something she shared with Rachel, her ‘very’ wild and sometimes almost too promiscuous roommate. As she headed home from having just finished her shift, she was already wondering if Rachel would have one of her many boyfriends over at the house when she arrived there. She hoped not. She was tired, wanted to take a nice hot bath, preferably a bubble bath, sit and relax and let the “Calgon moment” sweep her away. The last thing she wanted, was to sequester herself inside her bedroom, trying to muffle out the sounds of Rachel’s ardor, which she was prone to vocalizing at the top of lungs whenever she really got carried away.

Once again, Jackie reflected on the fact she really wasn’t a prude, was certainly open-minded for the most part, and usually wasn’t all that bothered by most of Rachel’s wild shenanigans. But…there was a time a place for anything, and sometimes the timing and place were more convenient for Rachel than it was for her.

She thought she was home free. Entering her apartment, Jackie stood just inside the doorway listening. All was quiet. She smiled inwardly already beginning to unbutton her blouse as she stepped into the hallway headed towards her bedroom. That’s when she heard it, or rather heard Rachel, and knew she wasn’t alone. Her fantasy of scented candles, plenty of bubbles, and a nice hot steamy bath suddenly being replaced by secluding herself beneath a pair of headphones listening to music instead.

“Oh yeah fuck me! Fuck my ass!” Rachel cried out in that near ear-piercing scream that had become her trademark.

“Damn!” Jackie thought silently to herself. Though annoyed she wouldn’t be able to do what she’d been hoping to do, it was Rachel’s words that froze her dead in her tracks just outside the not fully closed door of Rachel’s bedroom.

“Fuck my ass?” Jackie repeated silently.

That was one of the few ‘lines-in-the-sand’ Jackie had drawn and never crossed for herself. Though up until a month ago, she’d also thought she’d never touch another woman either. But Rachel had teased her sufficiently into dangling her toes over that particular line anyway. They’d gotten a little tipsy over a good bottle of wine, had been watching a rather racy movie together where two women, close friends not unlike themselves, had fallen into bed together. From there, Rachel had begun teasing Jackie unmercifully about being horny, (which she was) and finally convincing her to let Rachel get her off using one of her many toys. The fact that Jackie had finally relented had been surprise enough. That she’d then masturbated Rachel with a vibrator had been another.

But this, well this was something else entirely! This was a line she would NEVER cross, this was a line she would never even dangle her toes over unlike the touching another woman thing. Even her ex-boyfriend had found that out in a hurry. He’d been going down on her, something Jackie admittedly did love. And just as she was nearing the sweet throes of orgasm, Darren had placed the tip of his finger at the opening of her ass as some sort of surprised enhancement to her pleasures. Well he had been the one to be surprised as not only had Jackie slapped his hand away from her, but she’d also bolted out of the bed as though being struck with a branding iron. She hadn’t seen him since!

“Oh baby, that cute little ass of yours feels so fucking good! So tight around my big, hard, cock!”

Jackie grimaced. She recognized that voice. Brian. She’d had, or rather still had a bit of a crush on him. And though Rachel had told her repeatedly to “go for it!” the thought of letting Brian bed her while still sleeping with Rachel wasn’t something she was sure she could handle.

“Tight little ass-fuck isn’t she?”

That was Jerry, Rachel’s ‘main-squeeze’ as she referred to him. But where Brian was, usually so was Jerry as they were best friends. Another reason why Rachel was always trying to hook the two of them up together so that they could perhaps “party” one evening. And though tempted, Jackie wasn’t sure she could get into a group thing either. Though that at least was something he actually might consider doing under the right circumstances.

She found she was actually holding her breath. She stood just outside the door to Rachel’s room, the door having been left ajar, which she wasn’t all that suspicious of in Rachel’s leaving it that way on purpose. And though Rachel couldn’t have known Jackie had gotten off work earlier than usual, she still wouldn’t put it past her to leave such a temptation waiting for her either. If Jackie had one real weakness, one real Achilles’ heel, it was her voyeuristic fascination with watching other people having sex. And as such, the ‘invitation’ whether it really was one or not, was too much of a temptation to pass up.

“At least for a minute or so anyway,” Jackie mused, trying to justify her pushing softly and quietly against the door so as to offer herself a naughty little peek into the room. She literally had to catch her breath, as what greeted her was something far beyond anything she was prepared for, or even anticipated seeing.

Nearly exact opposites of one another, Jackie caught her breath at the sight of Rachel’s slightly plumper five-foot four inch frame sitting upright on Jerry’s prick. With short blonde hair that was almost too short, as she’d sometimes actually been mistaken for some kind of a lesbian lover whenever the two of them had gone out somewhere together. Something Rachel always found amusing, especially as she didn’t have any hang-ups about girl-girl sex, and was in fact probably considered more ‘bi’ than heterosexual. Still, it wasn’t seeing that so much, as it was seeing Brian kneeling behind her as she sat, ‘his’ cock obviously sliding in and out of Rachel’s ass as she was simultaneously fucking and being fucked from Jerry below her.

“Oh yeah, fuck me baby, fuck my sweet tight little ass!” Rachel moaned deliriously.

Before she realized she’d even done it, Jackie felt her own hand gingerly teasing the hard taut nubbin of her left breast through the blouse she had partially unbuttoned earlier. Standing in the doorway, but with the hallway darkened, she felt fairly secure in her ability to continue watching them all without anyone actually being aware of her presence. Especially as involved as they were at the moment, with Jerry content to continue to lie there prone, his hands joyfully kneading, sometimes squeezing Rachel’s much larger breasts. But it was Brian who knelt behind her friend that both repulsed her, yet at the same time fascinated her so. It was impossible for her to tear her eyes away from the decadent, degrading scene as it continued to unfold. Holding onto Rachel’s twin spheres, Brian was thrusting in and out of her ass with a rapidity that seemed impossible to achieve, especially as it was her ass he was actually fucking! She couldn’t imagine, nor even begin to imagine having anyone, or anything thrusting in and out of her ass the way Brian was doing to Rachel’s.

“Harder you fucking bastards!” Rachel cried out once again, fuck me harder! I’m almost there!”

Mesmerized, Jackie stood secretly behind the door, peeking through the slightly wider crack that she had carefully created. Continuing to stand there caressing her breast, she had now added the additional stimulation of slipping her hand down between both hems of her skirt as well as her panties. Finding her well-oiled pussy eagerly awaiting the touch of her probing fingers, which she had now begun to gingerly stroke, allowing the excitement and pleasure of her curiosity to replace the initial revulsion of seeing Brian’s cock sliding in and out of her girlfriends vulnerably exposed ass.

Rachel had already begun to do “The Tasmanian” as Jackie had teasingly referred to it. Suddenly whipping her head back and forth, side to side, all the while gyrating her entire torso almost spasmodically, arms flailing about her, breasts swinging wildly to and froe as she came. She’d seen Rachel come like this before, and knew that when she did, she was letting out all the stops, totally and completely letting herself go, no matter how weird or bizarre it might seem to anyone else seeing her climax like this. She could care less how she looked, and said so. All that mattered to her was how it felt. And it felt…”fucking fantastic!” she would always exclaim afterwards.

Jackie felt her own ‘mini’ climax spread in a less than satisfactory wave of pleasure. More a pleasing tingle of sweetness than any kind of earth-shattering explosion, certainly nowhere close to what she was seeing Rachel enjoying at the moment. But it was the fact that Rachel was having such a tremendously powerful climax, obviously so…with one cock in her pussy, and the other in her ass that held Jackie spellbound to the spectacle before her, far longer than she should have stayed, precariously so, lost in thought for a moment, wondering.

“Well? You just going to stand there playing with yourself? Or are you finally going to come in and join us for a change?” she heard Rachel asking, stunning her back to the present with no where to run…or hide the fact that she’d been caught, especially as the door suddenly flew open with Brian standing before her, his cock still rock-hard rigid, the smile on his face wickedly pleased to see her standing there.

Only then did Jackie realize that she still held one hand on her breast, and the other unashamedly down between her legs.

She felt her face burn crimson, even more so when she found herself lustfully gazing down at Brian’s condom-covered prick. Just the sight of the condom itself suddenly seeming wicked, “naughty” she thought silently to herself, realizing where it had been, where ‘it’ had been. Brian’s cock, Brian’s hard stiff condom-covered cock so brazenly sticking out between his legs, bobbing up and down with eager anticipation.

Jackie couldn’t even speak, suddenly feeling herself being pulled into the room, though it was more like she was floating rather than being half-dragged, half-carried towards the bed. She caught a momentary glimpse of that line below her, saw herself floating above it, crossing it, then the feel of many hands upon her as the last shreds of her clothing were removed.

“She ok?” she heard Brian asking as though his voice had come from thin-air. “She looks like she’s stoned or something.”

Jackie heard Rachel laugh. “No, not stoned, not quite. Just buzzing, she got that way the first time I fucked her with my vibrator,” Rachel explained.

“Damn, I’d love to have seen that!” Jerry countered.

“I’ll bet you would,” Rachel snickered, turning then to address her roommate as Jackie only then began to shake herself from the fugue she’d suddenly found herself in. “So Jackie honey, which one of them would you like to take that virgin ass of yours? Jerry? Or Brian?”

Jackie found herself glancing back and forth between the two men. Both of them with rigid hard cocks, though Jerry’s obviously the larger. She could feel and sense herself smiling, wondering briefly how she looked with what must have been an almost idiotic expression on her face. Though the choice was still an easy one, even if Brian had had the large of the two cocks.

“Brian,” she near whispered. “I want it to be Brian.”

“Shit! Well, at least I get to finally fuck your roomies cunt!” Jerry spoke to Rachel.

“Yeah? Well you’d best be gentle with her Jerry, it might be the one and ONLY time that you do, especially if you get too rough with her. And that goes for you too Brian, especially you!”

Jackie heard a rustle as Brian fished out a new condom, too embarrassed to look over to confirm it however, still dream-like as she felt Rachel leading her over to the edge of the bed.

“Climb on up honey,” Rachel told her. Put that sweet-slick pussy of yours over my Jerry’s cock. That’s it baby, that’s it…just like that.”

Rachel had held onto Jerry’s cock, fitting it, then removing her hand just as Jackie allowed herself to slide fully down the length and girth of him until fully, yet comfortably impaling herself.

“Why don’t the two of you do a little pre-emptive fucking for a moment while Brian lubes himself up, and while I make sure you’re all nice and ready,” Rachel told her.

It had been well over two month’s since Jackie had been with anyone, so the feel of Jerry’s cock, even if it was Jerry, still felt good to her. She felt a tentative tickle near the opening of her ass, in reflex, clenching herself tightly.

“Relax baby,” Rachel said soothingly, “I’m not going to hurt you. If anything, I just want to make sure that Brian here doesn’t hurt you either. So relax, let Jerry’s cock stroke you a little, excite you some while I do this.”

Jackie did. She found herself grinding against him, enjoyed the feel of his massive member filling her too long forgotten pussy. This time, when she felt Rachel’s delicately probing finger, she did relax, relaxed well enough anyway that she didn’t flinch as the tip of her friend’s finger actually penetrated, the lubrication she was using already coating most comfortably the insides of her virginal fuck-tunnel.

“Feel good?” Rachel asked softly. “I’m not hurting you in any way now am I?” she asked.

“Nnnn, No,” Jackie stuttered for a moment finally finding her voice. “No, doesn’t hurt…feels good,” she stammered still, the feel of Jerry’s thick hard cock continuing to slow-stroke into her as Rachel’s much thinner, even more delicate finger continued to probe, massaging the tiny puckered opening of her ass.

“Ready Brian?” Jackie heard Rachel asking. “And remember, easy…slow and easy. You let her tell you when it’s ok to go any deeper ok?”

“Will do,” Brian replied. And Jackie could hear the etched excitement in Brian’s tone of voice, easing her tension somewhat, realizing as she heard him speak that he was just as anxious, just as excited as she was. That, and the caring tone he had used, giving her some measure of assurance that he wasn’t just going to spear her ass and wait for the pain to finally subside before fucking her even more enthusiastically without any care for her pleasure or discomfort, whatever the case might be.

“Don’t worry honey,” Rachel continued assuring her. “I’m not going to let Brian put any more of this inside you than either one of us are comfortable with ok? And he knows, should he even try without our say so, I’ll break the mother-fucker in half too!”

Jackie laughed in spite of her nervousness. “Anything you say sis,” she said affectionately. “I am trusting you…” she left off saying.

“And as for you Jerry,” Rachel cautioned, “You can hold still now until I say so. Go ahead and let your cock do the happy dance inside her if you want, but nothing else. Not until I tell you it’s ok got it? Oh…and one another thing, when you’re ready, when you can’t hold out any longer, I’m the one who has dibs on all that stuff floating around inside your ball-sack got it?”

Jerry merely nodded his head. He knew better than to argue with Rachel, especially over his “pearly-prize” as she called it.

Jackie felt the tip of Brian’s prick pressing against the sensitive opening of her ass. Simultaneously, she also felt Rachel’s fist as it too rested against her, ensuring as she did that Rachel was indeed in control of any sudden movements by Brian.

“Easy does it now,” Rachel instructed, “slow and easy, just say when,” Rachel stated turning towards Jackie. “You let both of us know how it feels honey.”

It felt good. But Jackie couldn’t speak the words at the moment, too focused, too concentrated as she felt the bare-ended tip of his prick suddenly press through the virginal opening of her sphincter.

“Nice baby, nice…you handled that really well. He’s got the head in you now, and I must say baby…it looks wonderfully wicked!”

Jackie was surprised. It did take a moment or two to become accustomed to the sudden intrusion, and though there had been a momentary stab of discomfort, it hadn’t been like anything she’d expected, or anticipated feeling.

“Rest easy there sport, we’re in no hurry here!” Rachel continued her warning towards Brian. “Jackie will let us both know when she’s ready for any more of that prick of yours!”

By way of an answer, Jackie felt the muscles in her ass loosen, taking that moment and opportunity to push back against him, forcing a good inch to slide in behind the head of his now comfortably enclosed prick.

“Ohhh,” Jackie moaned, but it was a pleasurable moan, and one that Rachel well knew and took satisfaction in hearing her utter.

Jackie took her time, gradually, slowly, she felt Brian’s long hard prick eventually enter her fully until she felt the base of his cock-stem nuzzle comfortably against the firmness of her ass. By now of course, Rachel had removed her hand, placing them on her roomies breasts where she now tweaked and pleasured her nipples, intensifying the sweetness and pleasure of her virginal ass now thoroughly filled, and wonderfully pleasured.

Jackie was swimming in a sea of unanticipated ecstasy. Even the feel of her roommate’s hands upon her twin spheres was an unexpected, but certainly delicious welcome. As the two men began to rock in harmonic rhythm within her, Jackie felt both her pussy, and for the first time her ass, begin to quiver in tingling surges of erotic, sensual delight. She could not have imagined, nor ever begun to comprehend that that particular opening could harbor such sensitivity, the kind of which was not only pleasurable, but becoming more and more so by the second.

“Oh yes, yes! Fuck me! Fuck my ass! Fuck my cunt! But whatever you two do…FUCK ME!”

Rachel burst out laughing. It was so out of character for Jackie to speak so coarsely, and hearing her do so while the sweet, stinging slap of flesh on flesh resounded within the room, that Jackie could only laugh with her, understanding as she did, why Rachel perhaps was so vocal herself whenever she was being so wondrously violated as she was now.

“Shut up you fucking cunt,” Jackie cried out wantonly, knowing full well that her verbiage would only please as well as amuse her friend.

As though to confirm that, Rachel laughed again, even louder. “That’s my horny little bitch!” she called, crawling up onto the bed suddenly straddling Jerry’s torso. Jackie wondered for a moment if Rachel would merely sit down on Jerry’s face so he could tongue her needful pussy. But no…as she quickly discovered, that hadn’t been Rachel’s intention at all! Rachel moved towards her, her long fingers reaching down to spread a part the lips of her liquefied quim, exposing the pearl-sized clit that stood out all shiny and expectant with needful desire.

“Kiss it you bitch! Go on! Kiss it! Suck it! You know you’ve always wanted to! So do it!”

She’d already crossed one line, so why not another. As a matter of fact, she’d already crossed two lines, now participating in what could only be considered a ‘group-sex’ type of encounter.

With Brian’s cock almost magically transporting her to another level of pleasure never before experienced, as well as Jerry’s thick massive cock, filling her cunt even more fully than it had ever been before, Jackie allowed the tip of her tongue to slither out, making contact with Rachel’s obscenely displayed clitoris. An electrical surge of additional lust exploded somewhere deep inside her mind, she felt her ass tighten, clenching the shaft that so boldly and freely slid in and out of her now, wanting it harder, even deeper if that was possible. Throwing caution to the wind, she wrapped her sensual lips around the tiny organ of Rachel’s rapture, drawing it deeply within her mouth, sucking it, and then much to her delight, hearing Rachel’s cry of surrender.

“Oh you beautiful cunt sucking slut you! Yes eat me baby…eat me, eat my cum-fucking pussy!”

It was too much for all of them to bare any more. As Jerry had promised, he quickly warned of his impending orgasm.

“I don’t fucking care!” Rachel screamed out. “Come in her fucking cunt if you want to, I’m cumming now too!”

The sudden flow of additional moisture bathing Jackie’s face triggered her own volcanic eruption. Feeling the jettison of Jerry’s spunk now bathing her womb, she felt Brian’s cock suddenly lurch, spewing deep within the confines of her ass as he thrust deeply into her one last time, holding it there, his balls discharging copious amounts of his semen into the barely manageable condom protecting her.

There were no words to adequately describe the intensity of the orgasmic release she now experienced for herself. The sudden presence of a thousand tiny white stars suddenly filling her head the last thing she briefly remembered before collapsing in a heap upon Jerry’s body, Brian tumbling upon her from behind.

She awoke, though how long she had been like this she honestly didn’t know. Rachel lay off to one side, spooning her from behind, Jerry spooning Rachel in a like-wise fashion. Brian, lying upon his back Jackie’s head comfortably cradled against his chest, her hand even now absentmindedly playing with his flaccid member.

She closed her eyes, smiling within her self. A brief vision of hundreds of miles of sand stretching out in all directions, and not a single line appearing anywhere, in any of it.

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