LATE NIGHT SHOPPING

Frank and Stephanie smiled at each other as they stepped out of the car. It was about 10:30pm when they arrived at the ‘Guilty Pleasures’ adult superstore. Frank opened the rear-door of the car, reached inside and took hold of the leash hanging around their unwilling captive’s neck. With a few yanks of the leash, their unwilling sissy slave stepped out of the car. Clinton shuddered as the cold, harsh night air hit his scantily-clad body; the black corset, pink skirt and fishnets offered little protection against the weather. His wrists were tightly bound behind his back with rope, and a second coil of rope hugged his chest and shoulders. A ball gag wedged firmly between his teeth muffled any attempts at speaking.

“Ready to go shopping darling?” asked Frank cheerfully.

Clinton had been held captive by the couple for two weeks at this point, and it was his first time outside of their house since he was kidnapped. The kinky couple, both in their late 40’s, had subjected the 24-year old to a wide variety of sexual torment. Clinton had been forced to become their sissy, a feminine slave subject to whatever filthy desires the two had as they engaged in their psychotic roleplay. Whenever they weren’t using him for their own pleasure, he was confined to his ‘bedroom’ – a sensory overload of pastel pink walls, satin pillows and fluffy stuffed animals, not to mention the wardrobe full of girly outfits they liked to trot him around in. Tonight however, the couple were looking to take their twisted games to the next level.

The pair looked their slave up and down as they stood out on the sidewalk, inspecting every aspect of his appearance. Stephanie had worked meticulously to ensure his makeup was perfect, and his thick brown hair was now finally long enough to be styled into two small pigtails. Frank checked the ropes to ensure none had come loose during transit, and that the gag was still firmly secured in place. Not that the couple weren’t well prepared for any potential emergencies, with spare ropes and a pair of handcuffs stashed inside Stephanie’s handbag. They each took a deep breath before entering the building, both of them equal parts nervous and excited for what they were about to do.

Stephanie stepped through the door, followed by Frank dragging their captive by the leash. The store was empty at this time, aside from the young woman working behind the counter. Her friendly expression changed to one of confusion as she noticed Clinton reluctantly walk through the door.

“Good evening.” said Stephanie warmly towards the young woman.

Clinton let out a panicked cry for help, although the words were mostly gibberish as they filtered through the thick plastic ball in his mouth. The woman gave a friendly wave, despite her initial shock the store was no stranger to exhibitionists looking to act out their kink in public. The saleswoman approached the couple and extended her hand.

“Hello, my name is Lisa, how may I help you today?”

She asked in a polite tone, not quite sure what to expect from these interesting customers. The couple shook hands and exchanged pleasantries, apologizing in advance for any of their ‘little girl’s’ potential poor behavior.

“This is our sissy Annabelle. It’s her first time here and she would like to get some fun new toys to play with.” said Stephanie. Clinton shook his head wildly, enraged and humiliated at being called Annabelle in front of the pretty young employee.

“Well Annabelle, we are thrilled to have you here tonight. I hope you find something you like, and if any of you need a hand don’t hesitate to ask!” Lisa was always happy to play along with customers to ensure they had the best possible experience inside the store.

Clinton whimpered as Lisa walked back over to the counter, seemingly unfazed by his desperate pleas for help. His attention was quickly drawn back to his captors as Frank tugged on his leash and led him down the first aisle. Clinton had never been inside one of these kinds of stores before, so the assortment of exotic toys adorning the shelves was an intimidating sight. First was the bondage aisle, where Frank picked out a studded leather paddle. Next came the costume section, where Stephanie gleefully inspected every garment before settling on two pieces of lingerie: one for herself and another for Clinton to wear.

Lisa watched on curiously as they made their way through the various sections of the store. The pair looked like a normal everyday couple, both well presented and neatly dressed, but she couldn’t help but feel like something wasn’t quite right. Clinton’s acting felt way more believable than anyone else she had seen role play in the store. The couple were more than 20 years older than him. And the way he was bound seemed overkill for typical BDSM, like they were concerned he might get loose. Still, she told herself she was just being paranoid. If this truly was something sinister, there was no way they would risk bringing him out in public like this.

After leaving the costume aisle, the trio then briefly went their own separate ways: Stephanie made her way towards the back of the store to browse the range of sex swings, whilst Frank dragged his thrashing victim into one of the private booths. Clinton fought hard and protested as loudly as the gag would allow, but he was no match for the much-larger man who pushed him inside and closed the door behind them. These booths were designated primarily as change rooms, however the assortment of condom and lube samples inside suggested the store was well aware of what patrons got up to in there.

At the other end of the store Stephanie made friendly conversation with Lisa, who was helping her reach the expensive swing she had carefully chosen. Clinton emerged from the booth about 10 minutes later with a disgusted look on his face, and Frank followed swiftly afterwards. He briefly stopped Clinton to straighten his skirt and check that the ropes were still secure, before marching him over to where Stephanie was waiting for them. The group continued their journey through the store, stopping briefly to pour through the assorted clearance bins in the middle of the aisles. Here they filled their basket with even more naughty novelties: nipple clamps, cherry-flavored lubricant, and a multipack of ball gags in assorted colors.

Finally they reached the store’s most popular section; on the wall closest to the counter sat an enormous collection of butt plugs, dildos and vibrators.

“Alright Annabelle,” said Stephanie. “Which toy would you like?” Clinton shook his head and mumbled; he had no desire to play along with their twisted game. Frank reached for a beaded purple butt plug that caught his attention and gestured towards Clinton.

“This looks fun. It’s quite a different shape to your other plugs at home.” Clinton again shook his head in defiance, his high-heels clicking on the polished floor as he angrily stamped his feet.

By this point Stephanie was getting annoyed.

“Listen sweetie, it’s getting late. If you aren’t going to behave yourself and pick something, we will just have to choose for you”. She turned and motioned towards the counter. “Lisa dear, could we borrow your expertise for a moment?”

Lisa happily strode over to meet them. Clinton made another desperate attempt to convince her of his situation, pulling away from Frank in her direction and desperately screaming for her to help him. This surprised Frank who almost lost hold of the leash, before violently yanking back on the leash and aggressively scolding him. Lisa’s friendly expression briefly turned to one of concern. Clinton’s visible displeasure of the scene was difficult to ignore, and Frank’s sudden outburst was the first time he seemingly broke character since they arrived.

Before she could process what she just saw, she was interrupted by Stephanie. “What would you recommend as a suitable toy for our darling Annabelle?”

She paused for a moment, drawing on her previous sales experience. “Well we certainly have a lot of great options to choose from. I suppose it depends; how experienced is he with anal play?”

Before Stephanie could respond, Frank chimed in. “I can assure you, SHE is very experienced.” he said with a wink as he placed his hand on Clinton’s shoulder. Clinton whimpered as he spoke, clearly evoking some unhappy memories.

“Of course, she, my apologies.” Lisa corrected herself. “In that case, we have a few things that I’m sure Annabelle will love”.

Lisa picked out a few different items from the shelf. “If you are looking to get a butt plug, the ‘Colossal XL’ is the largest we carry. It’s a traditional shape, but what it lacks in innovation it makes up for in size. We only recommend this for the most experienced shoppers.” Clinton’s knees trembled at the sight of it. “Of course if mechanical is more her style, this vibrating weighted plug is also a top seller.” Stephanie and Frank cooed in delight at each of the various options, as Clinton watched on in horror.

“Of course we also have some excellent dildo options.” she said as she reached for the hot pink monster known as the ‘Bunny Breaker’. “This is our deluxe rabbit vibrator, it has a motorized shaft, 10-hour battery life and is ribbed for additional pleasure. This one is a little on the pricier side, but the reviews speak for themselves.”

Stephanie turned to face Clinton. “Well darling, which one would you like?” This time he didn’t even respond, only staring back at her with his furious, piercing eyes. Stephanie smiled before turning back to Lisa. “Fine, we’ll take them all”.

Lisa was stunned. “All of them? Are you sure? That’s going to be pretty expensive.”

Stephanie nodded. “Nothing’s too expensive for our little girl. Ring them up”.

Lisa obliged, and the group made their way over to the counter. Clinton was mortified as he watched Lisa ring up each item the pair had diabolically chosen for him. Even more frightening than anything though was the price. “Alright, with the toys, the swing, the lingerie and everything else, all up your total comes to $491.60. How would you like to pay?”

Stephanie opened her handbag and rummaged around for a moment, eventually retrieving a brown leather bifold wallet. Clinton’s heart instantly sank; it was his. She swiped Clinton’s debit card on the machine without hesitation. A successful ‘ding’ followed shortly afterwards. All of his savings, gone in an instant. It was this last act of cruelty that finally broke him. Tears began to stream down his cheeks as he bellowed into his gag, violently shaking and tugging against the leash. Lisa locked eyes with him. This definitely didn’t feel like a role play anymore. This felt real.

“Honey, take her outside and put her in the car. I’ll be out shortly once I finish up here.” Stephanie spoke in a commanding tone. Frank nodded. He grabbed his panicking captive by the waist and hoisted him up over his shoulder. Clinton locked eyes with Lisa one final time, howling in pure desperation as he was carried towards the front of the store and disappeared out the door. Stephanie smiled at Lisa as she picked up the bag. “I’m so sorry for that little tantrum. I’m sure she’s just a little tired from all the excitement.”

Lisa could only muster a nervous smile, Clinton’s muffled screams still ringing in her ears. “Thanks for all your help this evening. We promise to come again real soon.” With that, Stephanie turned and made her way out onto the street. Lisa remained frozen in silence behind the counter, still trying to process everything she had just witnessed.

By this point, Frank had just finished strapping their kicking-and-screaming sissy into the car. The couple embraced each other, sharing a passionate kiss under the glow of the neon sign above them. “That was so much fun!” Stephanie’s nose crinkled as her face beamed with joy, and she leaned in for another kiss.

“The fun is only just beginning my love.” Frank replied seductively.

The two shared a final glance towards the store as they climbed back into the vehicle. Frank pulled out from the curb and began the 20-minute drive back home, as Clinton sobbed in the backseat. Unfortunately for him, he knew that was only just the beginning of what they had in store for him that night.

Also read: Sissy Pegging Stories