A is for Anal

by Thesandman

Caution: This Sex Story contains strong sexual content, including Anal Sex, .

Desc: Sex Story: Jackie learns that some lines are actually meant to be crossed

Many Feathers

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.

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