The Window Ch. 03

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Jen learns something new.
1.3k words
4.31
12.4k
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Part 3 of the 5 part series

Updated 09/22/2022
Created 06/03/2004
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Standard obligatory disclaimer: They’re all 18+

When Jen woke later that afternoon the TV was hissing at her and the tape had long since rewound. She didn’t care; she had things to think about. The memory of her own voice begging to be fucked in the ass filled her mind. It wasn’t that the thought bothered her, it was the mechanics of the act she was concerned about. She knew her ass was sensitive, and the visual images, and perceived feelings of getting a cock jammed up there made her wet. The trick, she thought, was to get used to it first. A warm bath, she thought would relax her, and the bottle of wine she had hidden in her secret stash couldn’t hurt… she’d been stealing Dad’s bottles for years, and she had a respectable collection; she’d never bothered to drink any of them barring a shot or two.

The more she went over the video in her mind, the more she knew she HAD to have Johnny, and in every way possible. She had discussed sex rather frankly with August, and reading her diary had learned more; the video was just the frosting on the cake. She knew for sure that people could cum from oral sex, both getting and giving… and that her ass was also an erogenous zone. She had cum that way before with her fingers, was looking forward with glee to using toys, and with absolute delight to the time Johnny would take her that way. She couldn’t wait for that. It took a fast few minutes with her fingers on her clit to gain some clear space to think and plan.

* * *

Jen rearranged her room somewhat. She had found a couple of Cheval-styled mirrors in the attic, and used them to complement the mirror on her closet door. Moving the dresser and vanity gave her two more angles of view: shifting the bed and putting up two folding screens gave her a private theater. The old videocamera was a welcome addition. Jen intended to enjoy every single moment of her self-exploration, and the pleasure she had already enjoyed watching herself in the mirror, she thought, might be increased by video. Recording her evolution into a sexual being also appealed to her intellectual and aesthetic side; she could eliminate positions that didn’t seem graceful and appealing.

Jen fortified herself with a glass of wine, and took the time to lovingly shave every inch of her crotch, from navel back up past her cheeks. She then had another glass of wine and two soapy enemas; she was horny not nasty. A warm bath and another glass or two of wine relaxed her further. She walked nude into her bedroom, swiveling her hips with the same proud arrogance and sexual open-ness that August had; Jen was already wet with anticipation. She set up the mirrors and cam for the best possible view, brought out the toys and lube, and made sure the wine was easily reached from the bed. She knew the big dildo was too large to use first but she fondled, licked and sucked it while she used her lubed fingers to ready herself. She was thinking of Johnny’s cock in her mouth, and was surprised when she came almost immediately.

Jen shifted her position so she could see her fingers sliding into herself. The golden-tanned fingers contrasted with her paler fair-skinned cheeks and the pink of her anus. She dropped the dildo and picked up the vibrator, slowly teasing it over her clit. The intense feelings this produced quickly had her hips hunching for better contact. Jen wanted more, and fast! The vibe was instantly deep inside her pussy probing again and again for her G-spot. Jen came three times in fast succession then reached for the wine as the trembling passed. While Jen was drinking the wine she examined her toys again and suddenly realized that the stubby fat object was intended to go in her ass and stay there: that thought she filed away for later thrills. She had a huge grin on her face just thinking about walking around full, stretched in public, and no person would know but her.

Jen refilled her glass, and reclined gracefully. She was positioned so that the main mirror and the cam were pointed directly between her spread legs. It took only moments to re-insert the vibe into her still-wet pussy. She watched avidly as it slid in and out, then after a few minutes she pulled it out, covered it with lube and slid it slowly deep into her ass. There was minor discomfort, but that passed almost immediately. Waves of pleasure coursed through her body as she pushed the vibe in and out, her other hand was circling her clit, and her hips bucked into another orgasm. Jen lay back for another sip of wine, holding the vibe inside. The tingling feeling it produced was somewhat distracting, but that was part of the exercise. She leaned over to grab the dildo and lube and refilled her glass. Jen clamped her ass muscles to hold the vibe while the fingers of one hand played idly over her clit. The other hand held the dildo as she examined it closely, wishing it was Johnny’s cock. A few licks and sucks weren’t satisfying, so she used both hands to lube it up, getting it very slippery; She then slipped it slowly but surely deep into her pussy. Jen started thrashing as she worked the toys in unison into herself, then a bit of syncopation, then in tandem. She’d never felt so full. The laughter that thought drew almost stopped her from cumming, but the intensity was new and awesome. She kept laughing afterward; the only experience she’d had was her “training sessions”. Jen watched for a while as the toys stretched her openings in and out… She lost interest fast though, as she began to wonder just how that big dildo would feel in her ass: she’d never had it in her pussy before either, and that hadn’t hurt.

Jen decided that food wasn’t a bad idea, and after turning the cam off went downstairs to get it. Running around the house nude felt delightfully naughty, and she made sure to sit in both of her parent’s chairs and then rubbed her ass all over the couch. She laughed on her way back up the stairs- so much for being Miss Goody-two-shoes! A sudden thought stopped her cold, and she went back downstairs. It took only moments to open the back door, and since it was dark enough she slipped outside, then ran around the house, back inside, and giggled all the way to her room. That fast little adventure had given her some very interesting ideas for later on.

She felt a slight ache deep inside, but decided that was from a long-needed stretch, and there was no way she was stopping now. Jen took the time to turn the cam back on, for a glass or two, turned on some music she found to be romantic, then went back to the bed. The dildo was still slippery from the combination of her juices and the lube, so she lubed it up some more, positioned it vertically on the bed, made sure it was pointed right and sat on it before she had second thoughts.

It hurt, more than she had hoped, less than she had thought. The feeling of being jammed full was very interesting. Jen took another glass while she got used to having her ass crammed full. As she felt herself relaxing she began moving up and down, fucking herself on the dildo and imagining the entire time that she finally had Johnny buried deep in her ass. It didn’t take terribly long before she was having another multiple orgasm that left her limp and sprawled out on the bed; she didn’t even have time to turn the cam off before she fell asleep.

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