Shopping for Jessica

by Gospodin

This work is licensed under a Creative Commons Attribution-ShareAlike 3.0 Unported License

BDSM Sex Story: This was a story I wrote for a competition run by a latex forum site I used to participate in. The story won first prize. Jessica discovers one day that the gifts from her anonymous on-line master become far more daring than ever before. Does she continue with the dare?

Caution: This BDSM Sex Story contains strong sexual content, including Ma/ft   Consensual   Reluctant   BDSM   DomSub   MaleDom   Light Bond   Humiliation   Safe Sex   Oral Sex   Sex Toys   .

Jessica stared at the blank tunnel wall as the green line streetcar plunged underground. The other passengers, had they been paying attention, would likely have chalked up her refusal to make eye contact as nothing more than standard "T" etiquette. Jessica herself was acutely aware of the self-conscious way in which she pretended that she was the only person on the train. In fact, she wished with every fiber of her being that she was.

It would be incorrect to say that none of the other passengers paid attention to her. A young accountant across the car from Jessica had occasionally turned from his copy of the Globe to soak in the beautiful strawberry blonde with glances that he hoped were short enough to be considered nonchalant. The cut of her chin and the fullness of her lips warranted a few passes, and her smart business suit with the leather skirt earned his admiration.

But the majority of his attention was directed at her legs. Jessica's shapely legs peeked out from beneath her skirt, dark stockings accenting the curves and shadows of her knees before vanishing into a pair of zip-up black leather boots above her calves. They were the kind of legs that always walked in an alluring strut, thanks to the excellent set of hips they were anchored to.

Had the tastefully-gawking man gone so far as to stare outright, he may have noticed the occasional anomaly in her outfit. Jessica herself kept her knees pinched tightly together, and clutched the hem of her long suit jacket as though she feared it might fly away at any moment. Each jolt and jostle of the train sent her heart pounding as she pulled and stretched the fabric out of shape.

The young man allowed his eyes to follow Jessica as she climbed out of her seat at Copley station. He puzzled as he noticed what looked like silver buckles peeking out beneath her jacket, at the back hem of her skirt. He blushed slightly as she held her briefcase behind her to cover it from public view before teetering down the stairs.

The man's face was a mere pink glow compared to the beet-red grimace on Jessica's face. She proceeded out of the station in a tight-kneed shuffle, the briefcase still shielding the backs of her thighs from view. Her other hand held the front of her jacket together at the bottom, in the manner of a woman who finds herself in a lightweight dress on a blustery day.

The reason for her caution was the skirt she wore, which had been advertised as a "leatherette spanking skirt." This meant, in practical terms, that it had no material covering her ass cheeks, and it was held together by a pair of buckling straps behind her upper thighs that created a push-up effect for the globes above.

Having waited for all the other passengers from her train to leave ahead of her, Jessica shuffled out of a black iron staircase shelter onto the city streets above. She had a short walk ahead of her, but it was made to feel longer by the latex "clit stimulator panties" she wore. They had been squeezed into a thong arrangement so as to honor the intention of her skirt, but the soft nubs still rubbed against her clitoris as she walked.

The obscene squicking between her legs was almost enough to help her forget the humiliation of walking the streets of Boston in an assless skirt. The shame that did manage to catch her attention was just enough to arouse her further. She teetered on the edge of horror and orgasm, trying as hard as possible not to think of what it might feel like to just throw down her jacket and crawl the rest of the way on all fours. She felt herself on the top of a precipice, steeling herself lest she step off into the abyss.

She had worked her way to this point slowly enough, and initially with some degree of innocence. One day after swim class in high school, she had been mortified to discover that one of the other girls had broken open her locker and stolen her underwear. Since she couldn't wear her soaking wet bathing suit beneath her uniform, she had been forced to improvise.

Jessica's imagination was well-matched to her skills. Cutting two circles from strategic locations in her swim cap, she had fashioned a crude brassiere (barely large enough for her growing teenage breasts) held on by the strap of her goggles. She had then put her legs through the holes in the cap and worn it as a misshapen pair of panties. This arrangement protected her modesty neatly, despite the occasional tickle from the loose folds of rubber between her legs.

Jessica began wearing the swim-cap panties once a month to help contain her menstrual flow, and reinforced their jagged cuts with rubber cement where necessary. They couldn't last forever, though, and she was soon forced to shop for a replacement. All of the products she could find for this purpose were unsuitably bulky and obvious, like adult diapers. Fortunately, a quick Internet search for "rubber underwear boston" had turned up a store that sold precisely what she was looking for.

The site, Eros Boutique, seemed to Jessica to be some sort of sex shop, but not like the pink monstrosities one finds in seedier neighborhoods. Most of those were just cheap video stores that had badly-made lingerie stretched over the mannequins in the windows. This place was in a hipper part of town, and behaved more like a fashionable clothing and knickknack store that just happened to cater to an "adult" clientele.

She had waited at home to intercept the UPS man on the day her order arrived, and ran upstairs to try them on. The difference was night and day. The swimcap had been loose where it ought to have been tight, and vice-versa. The new pair were designed for a woman's hips, and held her womanhood like a firm yet gentle hand.

She had tested the fit for a long time, admiring the way the seams rested properly against her flesh, the old swim-cap's jagged scissor-cuts notably absent. She massaged herself through the material, relishing the sensation that they somehow formed a new layer of skin. That evening she had to wash them out half a dozen times.

Jessica had, of course, come a long way since those early innocent days. She had matured into a gorgeous adult, and her star was on the rise at the office where she worked. Her sex life had been a moderate success, all told, but she never wore rubber on a date lest rumors get out. She certainly valued her reputation, though perhaps to the point of paranoia at times.

This caution with regard to public opinion would seem peculiar to the informed observer of her public walk of shame. More curious would be the dramatic manner in which she relaxed the moment she entered the Eros Boutique itself. She immediately softened the moment she crossed the threshold, her briefcase shifting to one side and her other hand ignoring the jacket in order to mop her brow.

The reason for the change was that she knew that the shop staff had been in their risqué business for quite some time, and had likely seen it all. They were professional, never snickering or prying, although that meant that they often responded to her interactions with a somewhat disappointing clinical detachment.

"I'm..." Jessica coughed, "I believe you're holding a purchase for me?"

The clerk stepped quickly into a back room and came out with a blank cardboard box, setting it on the counter.

"The buyer came in to inspect it before paying," the clerk read off a post-it, "and left it for you to collect."

Jessica looked up suddenly, surprise on her face. "You spoke to him?"

The clerk smiled politely, holding up the note. "Not personally."

Jessica had spent a great deal of time online in the past eight years or so, discussing and playing out her growing sexual fantasies involving latex, bondage, and exhibitionism. She had attracted a small following of on-line playmates, many of whom had managed to coax her into sending photos of her latex-clad body (though strictly from the shoulders down).

Recently she had set up an anonymous wishlist so that her admirers could purchase items for her to wear. She would reward them with carefully-manipulated photo sets of her modeling the items in front of a bedsheet, her head blurred into anonymity. Jessica loved the feeling of exposure, and their clumsy praise of her erotic charms never failed to arouse.

Recently, however, she had agreed to a new game. A man she had scened with in chat rooms and e-mail for a few years began buying her presents of his own choosing. She knew him only as "Darlington"; and since she would not give out her address, the items were kept at the store for her to pick up. The agreement was that whatever she was given, she would wear until she got home.

In payment, she always sent him a long and detailed description of the day's events. Often attached to the frothing and turgid descriptions of her arousal, shame, and anticipation were a few hastily-anonymized photos of the new gifts on her body just before she peeled them off and took a long relaxing bath.

The spanking skirt had been picked up during the spring thaw, and she had worn it home beneath a heavy felt overcoat. She had been fortunate enough to put on full nylon hose that day, and as a result the chill at her bottom was no worse than her calves. Darlington had ordered her to wear it to the store this morning, promising that a suitable replacement would be there for her to appear in at work.

Jessica hoped with all her heart that it would be, since she had a crucial contract negotiation scheduled for that very afternoon. She gingerly carried the package to a nearby cafe, buying a coffee and slipping into the bathroom to change. She hung her jacket on a hook and mused over what she had just learned.

It had never occurred to her that Darlington lived in the Boston area, or even on the East Coast. He always left her with the impression that he was English: he spelled words like "colour" and "honour" when he chatted, and his mannerisms were rather old-world. The notion that he could actually make a personal appearance at the boutique rather startled Jessica.

Checking the time on her watch, she tore open the box. At the top of the pile was a plastic bag from a well-known expensive clothing store. Opening it, Jessica sighed with relief as she unfolded a stylish black calf-length skirt that matched her long suit jacket nicely. The garment was obviously added to the package after the fact, as Eros never carried anything so modest.

Undoing the buckles on her skirt, she began to look at the rest of the garments in the box. A silvery rubber overbust corset, decorated down the front with black straps, lay atop a matching pair of pewter latex stockings. Sighing somewhat, Jessica unzipped her boots and peeled off her thigh-high nylons.

She took out a tube of skin cream that she had long ago emptied and filled with Eros Bodyglide, and shook a few drops into the stockings. She rubbed them a bit to spread the lubricant about, then gathered them into bunches and slid her pointed toes into the glossy sheaths.

Unbuttoning her blouse, Jessica peeled off the rubber bra she had been wearing and slid into the corset. She struggled as she sucked in her gut, and after a few minutes was able to pull the zipper up to her cleavage. Admiring her enhanced curves in the mirror, she noticed that the rings on the front straps had no connecting mechanism.

Glancing down into the box, she saw a hand-written note:

I have taken the liberty of keeping a few bits and bobs for the time being. You can pick them up from the concierge at the address below.

The address listed was a hotel in Harvard Square. He must have flown in just to engineer this stage of their little game, Jessica realized. She searched the box quickly.

Jessica lifted up the note to reveal a black leather thong decorated with silver chains, a white plastic egg with a black wire tail, and a plastic baggie full of tiny polished heart-shaped padlocks. She turned the box upside-down, but the keys to the locks were nowhere to be found.

Jessica seized for a moment, realizing that she was expected to lock herself into the corset until later that evening. Of course, she never had any opportunity to remove her items until she got home anyway, but somehow the immutability of the locks stunned her.

She worked her slackened jaw in disbelief, trying to wrap her head around both the fact that she was expected to do this and the fact that the very idea had caused her to wet the tickling nubs of her panties. Swallowing hard, she opened the baggie and slowly pulled out one of the glittery silver locks.

Hypnotized, she threaded it through the loops of the top strap. Just who was this Darlington fellow that he could go around telling girls to lock themselves into perverted underwear like this? She was an important businesswoman! Imagine the nerve!

Jessica held her breath, shut her eyes, and squeezed.

Hearing the delicate but sharp "click," she opened her eyes wide and dropped her chin to look at what she had done. Tugging at the lock merely stretched the latex garment a little, and no amount of fumbling could find an emergency release catch. Panting and moaning with a combination of fear, regret and extreme arousal, she reached her hand into the baggie and fished out the next lock.

"Nonooononooonononooonooooo..." Her mouth chanted "no", but her fingers kept on squeezing each little locking "Yes!" down the front of her shiny new foundation garment.

Having secured the erotic corset to her body, Jessica tossed the baggie with its two remaining locks back into the box and pulled out the plastic egg. It looked like one of the bullet vibes she had bought a few years ago, but no amount of twisting caused it to turn on. The batteries, she discovered, were already inside, and shaking it didn't cause any vibrations.

Recognizing that she was already committed to this dangerous game, Jessica sighed and unclipped the garters from her stockings so that she could peel off the teasing panties. She wrapped them in the spanking skirt and tucked them into the shopping bag that the more modest skirt had come in, pushing the bundle deep into her briefcase. Wetting the egg with Bodyglide, she pressed it between her labia and felt her pussy swallow it hungrily.

Recovering quickly and ensuring that the retrieval wire was within reach, she turned to the last item in the box. It was a leather thong that fastened via hasps at the top corners of the front plate. Delicate silvery chains dangled in front, so that they tinkled lightly when shaken. The hip straps fitted via thin slits to the front hasps, but seemed to have no catches of their own.

Jessica choked back a yelp as she realized that the two locks still in the baggie weren't merely extras, as she had first thought.

"Oh fine, fine!" she mumbled to herself, "All right, bastard. You win! You know I can't back out now, don't you?"

With methodical thoroughness, Jessica prepared her body for the fact that she wouldn't be able to take off her underwear all day. Cleaning herself completely, she finally tucked the egg's wire out of the way and pulled the chastity belt's straps to a comfortable tightness, snapping the locks on.

At the sound of the tiny clicks, she immediately threw her hands between her legs and began rubbing the black leather with her fingers. She was astonished by the lack of sensation in her pussy. She had worn rubber against her snatch for so long that she had become used to every movement and bit of friction being transmitted directly to her erogenous center. The feeling of arousal and anxiety took on a sharper edge as she tried not to think about how she may have just made a mistake of epic proportions.

She was interrupted from her explorations as someone who had heard her flushing knocked on the bathroom door.

"Um, just a minute!" Jessica's heart raced as she reattached her garters and threw on her blouse. Dressing quickly, she soon had her long skirt and boots on again, verifying in the mirror that for all outward appearances she was dressed perfectly normally. Taking a deep breath, she threw on her suit jacket, gathered up her briefcase and the empty box, and bolted out of the cafe.

She made good time to the orange line station and ran directly into a waiting train. She checked her watch and noted with some relief that she was on time for her morning appointments. She rode through the tunnels of Boston feeling better for her modesty, although the reality beneath her stylish business clothing ate at the corners of her mind.

As the train rolled toward her office, Jessica pulled a memo about the afternoon's scheduled negotiations out of her briefcase and began to review it distractedly. She concentrated as hard as possible to prepare herself for a normal day. Soon she was lost in facts and figures, flipping through the e-mails she had printed out before leaving home that morning.

Her focus was broken by a sudden motion in her pussy. Her fist clenched immediately in surprise, crumpling a printed-out spreadsheet as the egg buzzed in fits and spurts. Casting her eyes around the train accusingly, she saw with a start that it was pulling into her station. Gritting her teeth against the uncontrollable stimulation, she grabbed her things and hopped onto the platform.

The vibrations became intermittent again as she moved away from the station platform, disappearing altogether by the time she reached street level. Stopping to calm herself down for a moment, she realized that the egg must be one of the remote-control variety. What she had thought was simply a retrieval string was actually a wire antenna. Someone had been operating the corresponding transmitter back on the platform, and the egg had only started up once she traveled within its limited range.

Had she noticed anyone waiting there? Anyone suspicious? Perhaps someone pretending to listen to a radio or fiddling with a PDA? She shook her head as she realized she had paid absolutely no attention to anything but reaching the stairs. She had no idea if there had even been anyone else there with her.

For a while she felt satisfied that her quick exit would have made it impossible to spot her, but then she remembered that Darlington had bought her the expensive skirt that she wore. He knew that she was going to wear a long jacket and high boots. He had her description, and perhaps he now knew her face.

The workday began uneventfully enough, and Jessica managed to put the morning out of her mind. She skipped lunch, acknowledging glumly to herself that it would not be a good idea to eat or drink anything until she had the keys to her chastity belt in hand. Soon the day moved on and it was time to have that all-important contract negotiation.

Jessica glided into the conference room, walking as evenly as possible to prevent the locks and chains of her kinky underwear from jangling noticeably. She slid into her seat between her colleagues, the corset holding her back primly straight.

"You're looking very well today, Jess." commented David, a director from the floor above hers. He was a well-meaning and friendly man, and quite attractive in his own way. But his square jaw and blue bedroom eyes were often ruined by an eager-beaver attitude in the office.

"Well thank you, Dave." Jessica smiled politely, "Think it'll help?"

David simply smiled awkwardly for a moment, then caught his composure and lamely chirped, "Well, I think that it's a sign that we're all feeling very positive today!"

The portly VP next to David rolled his eyes and punched a button on an intercom, calling in the other company's representatives so that they could begin. Four Englishmen filed into the room, shook hands all around, and sat down.

The negotiations went well at first, and Jessica felt confident and outgoing. After a while, however, the men on the other side of the table began to flood them with numbers, obviously hoping to confuse the bargaining in their favor. Things began to spiral downward, and Jessica's team showed weakness and lost crucial ground.

Finally sensing that they had the advantage, Jessica's opponents wrote out a complete offer that was decent, but not what her team had planned on. As they passed the paper toward her side, she suddenly felt the egg within her buzz into life. The transformation in her head was instant: one moment she was a smart and powerful businesswoman engaging in crucial negotiations, the next she was a body of sex and rubber trying to hide beneath a uniform. She gasped loudly, sucking air into her lungs as her eyes bulged with surprise.

Jessica realized with horror that Darlington must be in the building. She looked across at the Englishmen in front of her, feeling dread at the thought that one of these smug looking men could be him. She studied their faces as the vibrations coursed within her, praying that no one could hear what she felt in her loins.

One by one, the smug grins on the four men slowly sank. Coughing nervously, one of them reached over and grabbed the sheet back.

"Er, let's try again, why don't we?" he mumbled, revising the figures with a fancy fountain pen. The moment he pulled the pen's cap off, the vibrations stopped.

Jessica gulped, and her head swam as the rest of the negotiations went on without her. She performed her role quietly, fading into the background as the VP maneuvered and argued and then eventually put his name to the piece of paper next to a signature from the other side. Once the contract was signed, hands were shaken again and the four men left.

There was a long silence as Jessica and her co-workers waited for them to pass out of earshot. Finally, there was a sudden round of cheers as her co-workers took turns shaking her hand one more time.

"That was very well done, Jessica!" the VP grinned, "You really had them pegged! I guess they couldn't stand to offend a lady."

Jessica accepted the praise graciously and then returned to her office to recover from the ordeal. She knew that those four men would be back later to work on organizational details. She sank deep into her chair, realizing that the whole show had been arranged. Darlington, she figured, had toyed with her and then given her the moment as a gift. She wasn't pleased.

Dave popped his head in and chirped, "Still here? The others all went home already. C'mon, let's go get a drink and celebrate! You're the woman of the hour around here today."

Jessica looked up and realized how late it was. "Oh, I can't, I..."

"Aw, c'mon Jes! I know a great place in Cambridge. I'll drive!" Dave's face took on a playful smile, "Please?"

Jessica realized that she was ravenous, and she could stop by the hotel to get the keys. "I've got an errand to run on the way, if that's all right." Jessica caught Dave's subtle nod of assent. "All right, then I'll be down in a few minutes."

After a slow ride through traffic, Jessica hopped out of Dave's car and ran into the lobby. The concierge recognized her immediately and handed her a paper envelope, which she opened only to discover a key card to one of the hotel's rooms. Looking out the front door distractedly, she decided to let Dave wait a little longer and ran to the elevator.

A green light winked on as the hotel room door's locking mechanism slid back. Jessica pushed it open slowly, her eyes growing used to the dim candlelight. On the far end of the room was a circular table, upon which a wide three-wicked candle gently glowed.

Jessica slipped inside and walked over to the table. Spying an envelope addressed to her, she picked it up and broke the wax seal with her thumbnail.

Take off your work clothes and hang them in the closet. On the bed you will find a blindfold and a set of cuffs. Put the blindfold on and then cuff your wrists behind your back.

Jessica balked. She was tired, and light-headed from hunger, but she had had enough. She decided to burn the note and head out. She would have drinks with Dave, and then go home and call a locksmith. It would be humiliating, but maybe she could get a thrill from it if she just herself enjoy it.

She held the letter to the candleflame, and her arm jerked back quickly as she felt the egg spring to life again. Gasping, she clutched the firm leather shield over her clitoris and tried once more to move it against her flesh. She wailed with frustration as the warm flickering light and unrelenting vibration stoked her fires.

Without entirely realizing what she was doing, Jessica unbuttoned her suit jacket and walked over to the hotel room's closet. She hung her blouse and skirt next to it, her eyes rolling up in their sockets as her mouth involuntarily formed the universal womanly "O" of pleasure. She picked up the blindfold and cuffs off the bed and sat in the chair next to the table.

Unzipping and kicking off her boots, she wrapped the steel cuffs around her wrists, slipping the padlocks into the built-in posts. The candlelight made her glossy corset and stockings shine, and the metal cuffs and hanging locks glinted as they swung and tinkled. Feeling nothing but need, she pulled the heavy blindfold over her face. Groping in complete darkness, she reached behind her and did her best to fit the provided large padlock through the cuffs' D-rings. Finally, with a click, she managed to complete her bondage.

Jessica sat panting for a few moments, twisting her arms to feel the cuffs pull at the lock's loop in different ways. The egg continued its dance against her womb, slowly teasing her insides to a fury. She began to mew like a kitten as she felt herself building toward an orgasm, little whimpers keening through her nose.

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