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Chapter 16
by
kerchek
What's next?
16: Shopping for her
Led by Sarah, they soon stood in front of a women's lingerie store.
Lingerie stores had always caught Mark's attention. Whenever he had gone to a mall or a shopping district, he couldn't help but sneak glances at the women inside, picturing them wearing something slutty and lewdly posing. While he wasn't confident to enter the store on his own, he often purchased slutty pairs of underwear for his girlfriends online. Although they weren't quite welcoming of his antics, he somehow always got his way.
Seeing the wide grin on Sarah's face brought him terror. It looked as though he was soon going to be in the recieving end.
"Hey, Sarah, why are we here?.. I just wanted to buy regular boxer briefs.. and maybe a sports bra? I think that should be enough to hide my... chest. " Mark mumbled grabbing Sarah's elblow.
"I don't think a sports bra would be enough to satisfy a slutty girl like you. Also, Mia, if you don't want them to find out what's between your legs, better speak in a higher pitch." Sarah advised dragging him inside the store.
The inside of the store looked very luxurious. With mannequins positioned in sexy poses and numerous pairs of underwear hung in stands and tabletop, he couldn't begin to imagine the wide variety of underwear they had. They seemingly had everything - from modest to slutty to just thin pieces of strings that made even him gulp imagining a woman wearing that.
Towards the end, he could even see a few women getting out of the changing room in just their underwear.
'Wait, is that Tiffany?' Mark narrowed his eyes to look closely. As soon as their eyes met, he looked away hoping she didn't recognise him.
"Hi, how may I help you ladies?" The store attendant soon greeted them.
"Hi, we are looking to get her cup size measured and maybe also something a little slutty for her," Sarah said pushing Mark forward.
"Sure, please follow me." The attendant led them to a corner of the store grabbing a measuring tape. "Can you remove your top? Oh, if that is a one piece, you can just free your straps."
"um, can we do it somewhere more private?" Mark softly muttered raising his pitch to sound like a girl.
"It's just us girls here. You don't have to worry." The store attendant assured.
"Not exactly..." Mark inaudibly mumbled.
Untying the knot, Mark carefully put his arms out of the dress straps. While the dress was still held in place by the waist clips, he couldn't help but feel it would all fall down if he didn't keep holding it.
"You know, even if you're small, you should still wear a bra to prevent it from losing shape. Or is it becuase you are naughtier than you seem?" The attendant joked seeing mark act all shy.
Wraping the tape arround him, she measured carefully. "Your bust size is 32B. Okay, now, do you want me to check your waist and hips as well?" the attendant offered.
"No! I mean no. I don't think my size hasn't changed much." Mark hurriedly insisted almost breaking character.
"Since we are here, isn't it better to get it measured, Mia? oh I almost forgot, miss, is it possible to measure over her skirt? She isn't wearing anything down there either," Sarah snickered.
"...Sure." Squatting a little, she started to meausure his waist and hips. The moment her hand accidently grazed over his crotch, she couldn't help but look up. Seeing the shy girl blushing red as a tomato confirmed her wild thought. Softly squeesing his ass, she got up pretending it was an accident. "Looks like your waist and hip sizes are 29 and 32. Let me go grab a few pairs I think you would be interested in. By the way, do you have any specific preferences?" She asked looking at the embarrassed girl putting her dress straps back on.
"Miss, there are a few." Sarah beckoned. Covering her mouth with her hand she whispered to the attendant. As her explanation completed, the attendant turned wide eyed.
"I was about to suggest a gaff but your idea seems more fun." The attendant smiled and left to grab a few pairs of underwear.
It was only when she returned, he understood why the attendant was so excited. All the bras and panties wear designed to make any man hard with a single glance. There were even a few pairs of corsets, pantyhose, stockings, garter belts and even matching suspenders. Looking at the panties he soon found an oddity: all of them were crotchless. There were even a few that went open from the crotch to all the way to the back. Even the pantyhose she had brought were open in the crotch area.
"I think I like all of them." Sarah answered delightfully checking the undergarments one by one. "Mia, wear one of them and see if it's the right fit."
Picking a black pair, Mark hurried to the changing room followed by Sarah. Taking his dress and shoes off, he stood there naked, semi hard and leaking precum.
Taking the black bra from his hand, Sarah helped him wear it, clasping the hook in the front. With the flesh on his chest now lifted with the bra, there was a clear definition of cleavage now. Taking a matching corset, she had Mark hold his breath as she tightened it around his waist. Lifting his legs, she pulled up the panties over his legs. Seeing how his now erect member gloriously poked out of his panty covered bottom made her feel wet.
"How is this even underwear.. It doesn't even cover my dick.." Mark murmured.
"Don't worry, we'll get you something else to hide your small problem." Sarah winked. Rolling a pair of black sheer stockings, she crouched down and started sliding them over his smooth legs. With the lace top firmly holding it in place, Sarah took a moment to relish.
As Mark was about to wear the dress again, the curtain suddenly opened revealing a sexy woman holding a few pair of bras. "Oh, I am so sorry. I thought it was unoccupied." She quickly apologized hurrying to close the curtain. But, seeing Sarah squatting on the floor next to Mark with his dick out and only in lingerie made her pause.
'Is that her boyfriend in lingerie? So small.. Wait.. have I seen him before?'
"Sorry, but have we met before?" she inadvertantly asked still holding onto the curtain.
"No!" Mark yelped.
"Wait, you are Mark, right? From the graduation party. It's me Tiffany." she introduced herself closing the curtain behind her. "When you bought that underwear for me, I never expected it was because you want to get kinky wearing one yourself as well."
"I am sorry, who are you?" Sarah asked still not clear of the relationship between the two.
"Oh, I work for an escort service. Your boyfriend had called me during his graduation party. Oh, I can never forget that day. But were you stuffing yourself back then?" Tiffany giggled looking at Mark's crotch.
Hastily wearing the sundress, Mark pulled Sarah wanting to leave fast.
"You guys in a hurry? Wait before you go, check this place out. I think a kinky couple like you two will definetly like it." Tiffany stopped them, holding out a card.
"Glory Circle?" Sarah took the the card, reading the title.
"Oh and my number is there on the back if you are up for something more." Tiffany grinned.
Parting with Tiffany, they soon went to the counter buying all the lingerie and hosiery. Taking out Mark's credit card, Sarah confidently paid for everything.
Their shopping trip soon continued, exiting each store with more and more bags, until they had to opt for home delivery as it became impossible to carry all the bags. With a wide range of boots, stiletto heels, clutches, handbags and clothes purchased, they were soon exhausted.
Except for a few pairs of women's gym shorts that Sarah allowed, there wasn't a single garment that gave him a sense of security his old clothes had given.
Just as he thought that the shopping spree had gotten over, Sarah soon pulled him towards a adult sex shop. If it was any other day or with any other girl, he would've been the happiest man to accompany. But with Sarah, he wasn't so sure. The corset suddenly felt even more tighter. Sensing an awful premonition, Mark nervously asked, "why are we going in there?"
Instead of replying, Sarah just gave a cheeky smile.
Entering the store, Sarah handed over her phone to the store clerk. Reading what seemed like a long list, he soon handed the phone back to her, giving a knowing look to both of them.
Returning shortly with a bag full of items, the clerk once again took Sarah's phone and one of the boxes in the bag. After a few minutes, he handed the phone back to her. "There is a trial room in the back. You can try it out now to see if it's working. Oh, not sure if you are aware, but the latest model you've chosen has built in GPS, long distance functionality and status monitoring functions as well. You can even schedule it to run automatically."
'Wait. What are we buying again?' Mark looked back at Sarah not following what was happenning.
Nodding with pure joy, Sarah took the bag with her and dragged Mark to the trial room.
"Mia, lift your skirt up." Sarah seductively whispered. Grabbing his semi hard dick, she continued to softly caress it making it stand. "Pinch it. Play with it. I want you to cum for me. Now."
"In here?" Mark nervously asked not understanding what was happening.
"Yes."
Silently agreeing he started masturbating. With his dick hard for almost half the afternoon without being able to release, he complied wanting to release as well. As soon as he felt euphoria after shooting out his load, he heard a clicking sound and a small pain from his ass.
Looking down he could see a metalic cage over his dick. The cage was so small that only his glans was visible through the rims of the cage. Touching his ass, he could feel something hard plugged into his asshole as well.
"This way you will not have to worry getting your dick hard in public." Sarah twirled the keys to the cage on her finger.
Mark couldn't handle seeing Sarah get more and more dominant. 'This has gone too far.'
Jumping up, Mark tried to whisk the keys away from her, only to stop midway feeling a strong sensual vibration. The anal plug that Sarah inserted in him was vibrating hard against his prostate, making him weak in the knees. He tried to reach for the plug and remove it with whatever strength he had remaining but was soon stopped by her.
"...And this is your punishment. By the way, this is just level 2. There are 3 more levels. Since the clerk kindly offered, shouldn't we check if it's working properly?" Holding his chin up, Sarah started to record him on her phone once again as she increased the intensity to level 3, 4 and then finally, 5.
The moment she set it to level 5, Mark orgasmed once more letting out a loud and girly moan. With his dick painfully trapped in a 1.5 inch cage and a strong pleasure coming from his ass, he cummed hard unable to maintain his facial expression. With drool still coming out of his mouth, Sarah softly slapped his face to wake him up from the pleasure.
Only a few minutes later did they leave the trial room as Mark had to catch his breath. He couldn't help but pant lightly even after. Closing his legs tightly, Mark walked out embarrassedly, red faced and head held low. He could feel the growing number of stares as they went back to the counter. Swiping his card for additional cleanup work, they finally completed all their purchases.
What's next?
Bully in Skirts
A bully bullied into wearing skirts
Mark, a former bully and freshman at Lakewood university, gets trapped and blackmailed into wearing skirts by sister of a former victim. Things start to get worse as more victims come forward for .
Updated on Apr 7, 2025
by kerchek
Created on Aug 24, 2023
by kerchek
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