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Birth of an Obsession

Category: Anal Sex
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She started slowly. It was something she didn’t think she’d try at all, actually, so the fact that she did so was a bit surprising. Men would bring it up, a sly interest in their voice as they tested the waters. She wasn’t having it, though.

“That’s out only. Nothing going in there,” she’d say, and some part of her would be revolted by the very thought. It was dirty, and she imagined, quite painful. Utterly not appealing.

But she was curious despite herself. Everyone else seemed interested. Or, at the very least, men seemed interested in having her become interested in it. But, no way was she going to let some guy stick his cock up her ass. Oh, he could fuck her from behind… she was a big fan of that. Impersonal was best, actually. Not that she was using them. Not really, because they got off without much hassle from her. She was a no strings attached kind of girl, and not surprisingly, many men appreciated that.

The interest continued to grow, though. So she started to experiment. At first it was a finger. Dry, because at the time she didn’t know any better. But it didn’t hurt, so it didn’t matter. A finger was small, just enough to tease without giving her what she knew would be the full sensation of being penetrated by something much larger. And it was easy, wriggling her finger past her tight little sphincter, so she didn’t think it would be too difficult to move up to something a little larger.

She had a vibrator, but moving from her finger to that was simply too big of a jump. She wasn’t ready to invest in any other toys, though. Investing in a toy seemed almost as if she were committing to the idea of enjoying assplay, and she was definitely not ready for that. So she did the only thing she could think of… improvise. At first it was an unusually thick tube of lip gloss, but she learned, much to her surprise, embarrassment and near panic, that things like that seemed to have a bad habit of migrating upwards. When it disappeared, she had horrible visions of emergency rooms and smirking doctors, but a little pushing worked wonders and she soon found herself realizing the value of objects upon which she could keep a firm grasp.

Cliché as it may have seemed, she tried what she could only imagine as the next logical step… a carrot. Not a well thought out plan, because straight from the fridge to her anus was a bit of a shock. And, she found, midway into insertion, that she simply couldn’t do it. Not that she couldn’t insert it, of course, because it wasn’t an overly large carrot. Just, she couldn’t handle the thought of herself kneeling on the bed, vegetable halfway up her rectum. It was… well… it was embarrassing. And, try though she might, she simply couldn’t find anything else in her house, short of an unsatisfying highlighter or two, to test out.

So, to the internet it was. She found a site with a far broader array than she’d ever thought possible, and after quite some time of looking at the various toys with varying interest, amazement, and revulsion, she settled on two. A small and a medium butt plug, one in black and one in tan just for the variety. She felt a dirty little thrill when the mailman delivered them, wondering if he had any idea about what was in the nondescript plain brown package. Wondering if he could see it in her eyes as she signed for them, the excitement that she couldn’t quite hide. Excitement that baffled her, really, because she didn’t know when she had moved from interest to anticipation.

She’d bought lubricant. The website had advised it and she decided that it only made sense. No natural lubricant there, after all.

The small plug was first up on her list. It was Saturday, and she felt a little odd stripping in the middle of the afternoon, digging out the tube of lubricant and ripping into the package, but she didn’t have the patience to wait. She wasn’t good about things like that. Besides, she figured she’d had to wait long enough for it to arrive, so there was no need to delay things further. The lubricant was thick and cool, and she smeared it on the dark silicone of the toy liberally. In person, the small looked just like it should… small. Still, it was thicker than her finger, and the slight bulge before the tapered bottom looked promising.

It slid into place easily. Perhaps a little too easily, she thought, and though she couldn’t deny that it felt impossibly good as she eased the toy into her, it just simply wasn’t enough. It was a tease, and much to her disappointment, she felt it start to slide out as soon as she let go of the base, her body’s natural reaction causing her to expel it.

Irritated, she put it off to the side, resolutely grabbing the medium plug. It was, in her opinion, significantly larger. The difference between small and medium was a little bit daunting. Exciting, but scary, but she was on a mission now.

A tingle of excitement ran down her spine as the cool tip of the medium plug pressed against her, and she couldn’t help but grin as she slowly started to press the toy inside of her. It was a grin that went away quickly. The difference between the two plugs was even more pronounced when it came to feeling them inside of her. Whereas the small had slid in easily, the medium soon introduced a great deal of discomfort. Discomfort that came fairly quickly, judging from the large volume of the toy still outside of her body. She knew that she hadn’t even come close to reaching the thickest part of the toy, yet she was already stuck. She didn’t want to give up yet, but she couldn’t press forward either. It hurt too much, and even though it felt like she was exerting pressure, the plug didn’t seem to be moving.

Taking a deep breath, she paused, letting her body become accustomed to the feeling. She closed her eyes, taking in the sensation. It felt like her heart was racing, like every nerve in her body was attuned to the slight throbbing in her anus. It was exhilarating.

That, in and of itself, was terrifying.

At the thought, she pulled the plug free, gasping as it left her. Without it she felt a little empty, as if something were missing. It was odd, how her body seemed to crave the penetration again even though it had just begged to be released from it. She was tempted. Tempted to try again, even though some part of her was deathly afraid of how much she seemed to be enjoying it all. It wasn’t a good thing, surely, to want to do this to herself. It couldn’t be right.

But it felt right.

So right that she felt herself pressing the plug back in, parting her anus yet another time. And this time when it started to hurt, she took deep breaths, screwed her eyes tightly shut, and continued to push. She pushed even when the pain moved to borderline excruciating, when she knew she wouldn’t be able to take much more. When the ache turned to a burning and she felt tears gather in the corner of her eyes. And then there was relief. The plug started to taper, and she felt her body close down over it with something close to delirious joy. It settled in deep inside her, the thick bulge filling her without being painful now.

It was, much to her surprise, far better than a cock in her pussy.

Fingers on her clit, she came hard. Several times. Until her body was limp and covered with sweat. Until she felt like she couldn’t move any more. Until she throbbed and her heart seemed ready to beat out of her chest, until the soles of her feet itched and her thighs ached from the strain. Until she became almost uncomfortably aware of the thick, unyielding plug still buried deep inside her.

She didn’t want to move, but knew she had to. The plug had to come out, and judging from the way her body was quickly starting to protest its presence, it had to happen soon. So, she grabbed the base of the toy and pulled… and pulled… and pulled. The end result, unfortunately, was nothing. The plug was quite firmly in place.

Heart racing now from panic, she pulled harder, sucking in a surprised breath at the sharp jolt of pain that accompanied the move. Her body had tightened around the plug, making it more difficult to remove it than it had been to insert it. And, she now realized, unlike insertion, there wasn’t a tapered point there to ease her into covering the bulge. Here there was nothing but the bulge, and her body was going to have to open up over it without much help.

She pushed, trying to use her body’s internal muscles to aid in the process. The sensation was oddly disconcerting, much like it felt when she was relieving herself. Only now, in some strange way, it was arousing to feel that slow glide of something pushing its way out of her. The feeling, as the thickest part of the bulge slid past her sphincter, had her orgasming again, much to her surprise and shame.

She felt herself afterwards, slightly disturbed by the fact that her anus was slightly distended in the wake of her experiment. But, things had returned to normal by the next morning, leaving her with a generally positive feeling about the whole thing, and she was already beginning to anticipate her next time.

A time which came a little sooner than she was comfortable with. But, by evening she was already near desperate to try again, even though her anus was still sore enough to have her wincing every time she sat down. And, even though it seemed as if the soreness would keep her from enjoying the plug again so soon, it seemed to slide in a bit easier than it had the day before.

It was some time later, perhaps after several weeks of masturbating herself to exhaustion with the plug nestled deep inside, that she began to crave more. She wanted to feel it moving within her ass, wanted to feel what it was like to be fucked.

So she pulled it out and pushed it back in.

By this point, it was much easier to insert the plug. Almost disturbingly easy, but she consciously pushed that from her mind in favor of the pleasure it gave. But this, this was different. Slowly fucking the plug in and out, feeling her body stretch, then close, then stretch, then close… it was phenomenal. So much so that she did it again, and again, and again until it became her new routine.

Until it wasn’t enough any more. She wanted the plug inside her seemingly always. She’d started inserting it and leaving it in, wearing it out as she ran errands and, when she felt particularly daring, to work. It felt naughty to have it buried deep inside her as she went about doing the mundane, and soon it became almost routine to have her ass filled and her pussy wet as she went about her day.

She needed more.

So she ordered the large plug, a little intimidated by the dimensions she saw advertised on the website. She had it sent priority mail, not trusting the 5-7 business days to get it to her quickly enough and when it came, she immediately ripped into the packaging, pulling it free.

She found it daunting. Much like the jump from small to medium, the move from medium to large was quite substantial. The large plug looked almost unnaturally large, as if something of that size should never be able to fit into her body. But, despite her reservations, she was going to give it a try.

Even though she had taken to inserting the medium plug without any lube, increasingly needing the friction and the way it made the plug feel larger than it was, she pulled it out again. For this one, she knew she would need it, and so she applied a liberal coating, jaw clenching in frightened anticipation as she noted how her fingers didn’t quite touch when she wrapped her hand around the thickest part of the bulge. Even the tip was broader, seemingly more blunt, and as she moved it to the now familiar territory of her anus, she shivered at the feel of it pressing into her.

Soon, she felt something she hadn’t felt it quite some time… pain. It was there again, that delicious feeling of stretching, of feeling as if her body would in no way be able to open up enough to take the thick intruder seeking entrance. She felt herself hesitate, pausing when the pressure grew too intense. But, she wasn’t going to give up, not when she could already feel herself growing wetter than she had in quite some time, and so she continued to push and twist, gasping in surprise when she finally closed over the broadest part.

As the plug settled into place, she lay still, heart beating erratically. Her breath came in fast pants, and it seemed as if fireworks were exploding behind her eyes. The feeling was… heavenly. She clenched around the plug, nearly cumming at the feel of its hardness deep inside her, parting her unbelievably wide. It was as good as the first time… better even.

After a month, she was sleeping in it. In fact, the only time she took it out was when it was absolutely necessary, but it always went back in immediately. It seemed as if it had become a part of her. She fucked herself with it nightly, wore it constantly. She felt empty and naked when it was not inside her. She felt incomplete.

Only, she was starting to feel as if it wasn’t enough. But then again, she’d been looking at that website again. It seemed as if they made an extra-large…

Maybe, she decided, she was going to have to invest in it.

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