She must have slept, because when she became aware again it seemed like an hour had passed. It was close to 11 now. June giggled as she realized that the two vibrators were still buzzing insistently. She turned off them off and swung her legs shakily out of bed, managing to pad over to the master bathroom for a pee. She grinned at herself in the mirror and splashed cold water on her face.
Feeling refreshed, she walked back into the bedroom, shedding her robe as she went. Her body tingled, her nerve-endings on fire. She was ready for even more wickedness, but now she was feeling truly naughty. She pawed through the jumble of goodies on the bed, and found the item she was after.
June had never experienced anal sex with any of her partners, not with her two boyfriends in high school, nor the four in college (two short-term flings and two pretty hot and heavy) or with her ex-husband. Bill (her ex) had tried several times to coax her into trying it, once sticking his finger uninvited into her ass, and then alternately begging and demanding that she let him fuck her there. But she'd rejected the idea in no uncertain terms. The idea of something as large as a penis (and Bill's eight-incher certainly qualified as large in her book) entering her tight ass just seemed absurd. Each time he'd tried, her whole body had gone rigid, ending any amorous feelings for the evening. At the time, Bill's obsession with screwing her anally had seemed so infantile, and that period may have marked the beginning of her realization that the two of them--despite having produced two children--were fundamentally incompatible sexually.
Lately, though, June had begun exploring the idea of anal sex in her online chats. One online acquaintance--a Denver woman named Sally, given to particularly earthy language--had extolled the joys of anal strap-on fucking, so much so that June had become intrigued. She'd started playing with her ass while masturbating, and had come to like the feeling of having a finger--or even two--pushed deep into her tight musky hole.
She eyed the object in her hand, the butt plug. It was made of clear silicone, and had a smooth tapered end and a wide flat base. In the middle it swelled out, like a pear. Again, June felt a momentary qualm, wondering how she would ever get this thing into her small hole. But she remembered more of her conversation with Sally, how she had counseled the liberal use of lubricant. June looked down on the bed and spotted the tube of k-y jelly, "free with any purchase."
Feeling a bit silly, she walked over to her full-length mirror, bent over, and looked at herself through her legs. She almost cracked up at the sight that she saw: a red-faced woman staring at her ass upside-down, her long brunette hair escaping from its tight bun to fall to the floor in a tangle, her large breasts hanging down pendulously. Oh well. Might as well get on with it, she thought. She grabbed hold of her butt cheeks and spread them, revealing her crinkled, reddish-brown hole. Was it just her imagination that it seemed even tighter than usual? She stuck out a nail tentatively and scraped it carefully around the center of her hole, probing at the tender bud. Pushing a bit, she managed to ease past the tight outer rim into the softer pinkness of the interior. Emboldened, she pulled her fingertip back out and coated it with some of the k-y jelly, and this time it slid in easily. She watched through her legs as her middle finger entered deeper into her ass and, to her surprise, realized that she was actually enjoying the sensation. For the first time, June realized that manipulating her ass like this created sympathetic sensations in on the opposite side of her perineum, and she felt herself beginning to get aroused. She glanced down at the floor at the butt plug, though, and still felt skeptical that her hole could stretch to accommodate it, at least without damaging herself. What if she tore something? Pretty hard to explain at the emergency room.
It occurred to her, though, that it was pretty pointless to have bought all these toys if she wasn't going to be brave enough to try them. She picked up the plug and began coating it liberally with the jelly. She could feel it warming in her hands as she prepared it, and she got more and more excited about the idea of having this thing inside of her. She started feeling as if she could do this.
June got down on her knees, and looked back over her shoulder at the mirror. She could see her target; her anus glistened wetly with the jelly. She aimed the tip of the plug into the center of her hole and began applying pressure.
"Unnnnghhh," she grunted, feeling a sharp twinge as the plug began stretching her. She almost stopped, but, again, her conversation with Sally surfaced in her mind. "You just push out, like you're takin' a shit," Sally had said, and June snorted with laughter at the memory. She concentrated, bearing down like she wanted to push the plug out (which wasn't far from the truth) and suddenly she found the opposite occurring: the plug was sliding farther into her tight ass. She groaned deep in her throat and almost tried to pull it out, but suddenly she got past the widest part of the plug, and the rest of it popped inside, until the base was tucked up nice and tight against her hole. She put her head down on the rug and stayed motionless for a minute, catching her breath. She was coated with nervous sweat, but she had done it!
After a bit, she raised her head up and looked back over her shoulder. She could see just the round base of the plug tucked up against her anus, and she reached back and ran her fingernail around it, tracing it on the rim of her ass. It felt amazing. Slowly, moving gingerly, she raised herself up until she was standing in front of the mirror again. She could feel the plug worming its way even deeper into her bowels. The feeling was odd but not unpleasant, and she found that she could move around even with the plug inside of her. She grinned at how she looked in the mirror. God, she looked like a sexy slut now, having cum all those times already and with her body now coated with a fresh sheen of love sweat. Her nipples were hard and beet-red, and she had to admit that, for a woman on the back end of thirty, she looked pretty hot. She certainly felt sexy, sexier and more beautiful than she had at any time since before she was married. She reached up and began rolling and pinching her nipples. It felt exquisitely good to tug on them like that, and then she got a truly wicked idea. She crossed over to the bed and picked up the nipple clamps. Each one opened on a hinge and clamped over the nipple, then there was a separate device that tightened them, squeezing the nipple a little....or a lot.
June unclasped one and fit it over her right nipple, then snapped it shut. She sucked in her breath tightly as it closed onto her nipple, but it did not really hurt, just pinched a little. She quickly fastened the other one, and then admired how she looked with the chain hanging down. Smiling evilly, she gave the chain a little tug.
"Oooooh," she moaned involuntarily. Now THAT hurt a bit, but it still left her with a bit of a tingle.
Moving stiffly, conscious of the plug squishing around in her tight behind, June walked back over to the bed and grabbed the DVD, slipping it into the player under her TV. She clicked it on, and while it was loading she busied herself with some other toys. The ben-wa balls she tucked inside her wet pussy, and was a little disappointed when she did not really feel much effect at all. Oh well. She knew something that would feel nice. She re-strapped the hand vibrator to the back of her hand, switched it on, and began rubbing her slit. Suddenly, she began shaking, as the ben-wa balls responded rather dramatically to the vibrations. It felt like the two balls were fucking her from the inside out and she couldn't believe how wonderful it felt. Voices from the screen made her snap her head up and she began watching the movie.
The "plot" of the movie, if you could call it that, was laughably lame, something involving a female executive and her new female intern. But when the intern--rather predictably--messed up, the movie got decidedly hot. The older woman insisted that the young girl meet her that evening at her house, a house that was equipped with a full-fledged dungeon in the basement. For the next hour, June watched in slack-jawed amazement as the woman put the young girl through the kind of pleasurable tortures that she had been dreaming about lately. First she stripped the screaming girl naked and inserted a butt plug into her ass (oh yes! June knew just how lovely that felt) and then tied her facedown on a bench. Mercilessly, the executive (who remained dressed) flogged the girl with a cat o' nine tails, until her ass was a bright shade of red. As the girl lay there sobbing, the executive, who by this time was sweating profusely, peeled off her own clothes and donned an evil-looking strap-on, very similar to the one June had purchased. Screaming at the girl to get up on her knees, she began fucking her pussy relentlessly, all the while keeping the plug buried up the poor girl's behind.
June lost track of how many times she came while watching this salacious display. She seemed to almost be having one long orgasm, yet each cum only acted to heighten her pleasure. She reached a point where she only had to touch her clit briefly with her vibrating hand to bring herself off, sometimes tugging on her nipple chain as she came. Her pussy was drooling cream in a steady river that dribbled down her butt crack and onto the sheets. She thought idly that she would have to make sure and wash them before going to bed that night.
