Dressing Room Punishment

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I immediately knew I wanted the plain black sweater on the closest rack to the left. It was cut off at the belly button, but it looked warm and cozy. It clung tightly to the mannequin, the breasts noticeably perky under the fuzzy fabric and highlighting the curves inward to the hips. Tight sleeves came down about halfway to the elbow. It wasn’t particularly revealing, nor sexy, but it was effeminate. I loved the girlish and soft look to it, how it would smooth out my body and emphasize my small chest. Moreover, I liked the thought of holding it up to myself in the mirror, trying it on with various pants and skirts, seeing what looked the cutest: a dark pair of skinny jeans, a black leather miniskirt — maybe even just a pair of cute panties, if someone was coming over. My cock was growing right out of the thong hidden under my jeans, imagining the feeling of squirming around on the couch underneath someone, their body rubbing up against my sweater, slipping their hands underneath to toy with my little titties…

I stopped myself — I could feel the precum on my cock already — just from a little black sweater! I was already getting my panties wet. I felt like I was a bit luckier than many girls. The only thing that gets them wet when they dress in pretty clothes is the thought that every guy will want to bend them over and use their pussies raw. I, meanwhile, almost cum from just getting to play dress up — teasing hard cocks are just an extra fun perk.

I grabbed a medium sweater from the rack and kept looking. It was early in the morning on a weekday, and the store I was in, A Girl’s Delight, was nearly empty. A young woman stood behind the counter, and another woman hovered near the dressing rooms. I was the only man in the store, which wasn’t surprising. I was certainly delighted — I could browse the store freely, pulling out various items without too much trouble — at least, that’s what I thought. Today I was in for a sweet treat.

The lingerie section was larger than most stores. Part of the reason why I chose this location was for its adult section: a few aisles devoted to what you would normally see in a sex shop. While it was nearly all novelty items, nothing was too expensive and the cheap material and scandalous coverage felt just right for the naughty girl I liked to be.

A hot pink embroidered push-up bra caught my eye, outlined in red lace frills and locking at the front, each cup had a cursive “suck my titties, baby” just over where the nipples would be. My cock practically grew another inch as I thought about the reaction I’d get from taking my top off — if I even wore a top with it. I grabbed an A cup.

An older woman, maybe 40 years old, down the aisle looked at me suspiciously. She was dressed elegantly in a white blouse and a tight black skirt, clearly taking a break from work. if she didn’t look so offended, I would probably find her attractive. However, I was dressed in men’s clothes carrying a whole load of young women’s dresses and underwear, so she probably thought I was some sort of pervert. Sure, I could be a dirty slut on occasion — I giggled to myself — but there was no need for the rude looks she was giving me. I decided to tease her, and pulled out the pink titty sucking bra I just picked up. Holding it up to my chest, making sure the words were emphasized, I went up to her and gave her a girly pout.

“Do you think my boyfriend will like my new bra, ma’am?” I wiggled my chest from side-to-side, puffing my chest out. I continued, slipping into baby talk. “Sometimes my wittle titties get ignored.”

“Excuse me!” she gasped, and rushed away. I laughed. Perhaps it was a bit over-the-top, but it felt good not to hide what I was doing. I gathered up the clothing, and continued looking through the lingerie.

I tried to decide what I would have to wear for the upcoming weekend. If I was lucky, I’d have company. My two female neighbors, being aware of my girlish fetish, would occasionally come over after an uncomfortable night out at bars, angry at guys trying to sleep with them. To feel better, they would pretend that I was one of those guys that used a cheap line, and to punish me, would feminize me. The trashier the lingerie, the more humiliating. They would always be delighted to rip a seam in whatever tiny outfit they forced on me with their strap-ons, and I was always too submissive to say anything but apologize for being a man — my thoughts ended as I was interrupted.

“Excuse me, sir?” I turned around and saw the pretty blonde girl from the counter. “Sorry, but apparently you’ve been bothering another customer of ours.”

I frowned. This was annoying. “Oh, well she was –“

She cut me off, stepping closer and holding a finger up to my lips. I froze; she was less than a foot away from me now. I suddenly became very aware of just how attractive this girl was; her plump breasts pushed out her top and showed ample cleavage against the taut fabric. She was wearing a blue and pink polka dot dress that flared out and ended mid-thigh. Bronze legs balanced on beige high heels; her bright pink toenails popping kayseri escort out and matching the finger that was currently muffling me. The dress ended in little ruffles on the shoulders, and most of her collarbone showed, only blocked by a small blue necklace that matched the dress. I broke away from her gaze and followed her arm down; her body curved in around narrow hips and back out to an ass that popped out perfectly.

“If you could follow me, sir.’ I panicked in my mind, trying to think whether the truth would be the most plausible explanation, when she poked my chest. I met her eyes again, and recognizing what she wanted, started walking down the aisle when she paused impatiently.

“Bring what you’ve picked out, obviously.” She pursed her lips and gestured at the few bags of clothes, bras and layers of tulle and velvet overflowing.

I picked the bags of clothes up and caught up with her. She was walking toward the back of the store, saying nothing, and I took my chance.

“This is all a misunderstanding; I didn’t mean any harm, and I really am going to pay for all of these clothes. It’s just that I like…”

The salesgirl grabbed my hand and looked back at me, threading through the stands of clothes and jewelry displays.

“Oh, of course you’re going to pay for those clothes. But you were harassing a customer — you need to learn some manners before you get the privilege of shopping here again.”

She stopped near the employee entrance and dressing rooms.

“Put your bags down. Security will be here soon, but for now, we have to keep you here.” She pulled my arms around my back. I obeyed, curious as to what she would do, and I felt as she snapped handcuffs around my wrists.

“This is store policy, of course,” as she walked around to my front, brushing her finger around my arm and to my chest. She came close to me again, and I pulled back as she leaned in close to me, bending my back awkwardly. I felt two soft hands grab my waist from behind.

“This, however, is for our pleasure.” She whispered into my ear as she brought her hands up to my face, pushing something hard into my mouth.

“Hey! What –” I yanked my head back against someone’s shoulder. Whoever was behind my back gripped me securely; I tried to weakly wiggle back and forth, looking down and realizing that the blonde salesgirl now was holding a bright pink ball gag, pressing it against my closed lips.

She clutched the back of my neck, forcing her body up against mine and squeezing my face against the gag.

“We’ve just got to make sure you don’t upset any more of our customers! Now open those dirty lips of yours nice and wide. We don’t mind if you’re a bit uncomfortable while you wait! Caroline, help him cooperate.”

I felt Caroline, the girl holding me from behind, reach out and — fuck, she put her hand in my pants, and started to squeeze. I almost immediately relented and obeyed, whimpering just barely as the gag slid swiftly into my mouth, pushing my tongue down. I felt as it was tightened around the back of my head and the pressure below eased.

“Well, that wasn’t so hard, was it?” I heard Caroline behind me laugh and she spoke, still holding my dick loosely. “Steph, what are we going to do with this one?”

The salesgirl, Steph, stepped back and appraised her work.

“Well, we obviously can’t have such badly behaved customers! Ma’am, what do you think we should do with the naughty boy?”

The woman I insulted came into view from my left. She was taller than me with her heels, and looked down as I quavered in Caroline’s arms, hands still bound together.

“This, this child needs to be taught a serious lesson about manners. Acting so inappropriate, thinking that behavior like that is funny — I won’t stand for it.”

Steph came forward. “Ma’am, it might help us if you told us what he said to you.”

She looked away, refusing to answer. “It’s too embarrassing to repeat.”

I felt Caroline perk up behind me. “We’ll, why don’t we have the little miscreant tell us himself!” She withdrew her hand and started to push the backs of my knees.

“Kneel down — you’re not going anywhere. I’m going to loosen your gag, and you’re going to repeat what you’ve told Ms. Jensen here. Understand?”

I looked up at Caroline as she circled around, helping me kneel to the floor. I felt my face blush. Caroline was an attractive young girl, probably only 20 or 21, with a round face and long dark hair. A sparkly blue top that met at her neck, wrapping around like a collar, exposed her arms and shoulders. I could see her belly button, the top ending before it met her tight white jeans. It would be too humiliating to share what I had said.

“Of course, I can keep persuading you, if you’d like.” Caroline and Steph stared at me as I glanced nervously between them. “I don’t mind touching down there if it’s for justice, of course.” She giggled. Ms. Jensen, as I now knew her, looked down at me distastefully.

I felt Caroline tug at the strap behind my head. “Now tell kayseri escort bayan Steph what you said.”

I felt my jaw ache as she pulled the ball out of my mouth. I immediate tried to apologize.

“I’m sorry; I didn’t mean — ” I stopped suddenly as Caroline slapped the side of my head. “If the next words out of your mouth aren’t the rude things you said earlier, then I will hit harder.”

I paused. I had no other choice but to confess and hopefully leave quickly after they finished satisfying Ms. Jensen of their store commitment. I looked up at Steph and began to mutter softly.

“I asked if she thought my boyfriend will like my new bra… and said that sometimes my,” gulping before I pronounced the next part, “wittle titties get ignored.”

I could see Caroline grinning out of sight of Ms. Jensen. Steph looked at me, then Ms. Jensen, apparently pleased with my response. Steph reached into the bag.

“And this is the bra you were talking about?” Steph held the bra up to my chest, and I saw Caroline trying to hold back laughter while Ms. Jensen was visibly growing more angry and embarrassed.

“Suck my titties, baby,” Steph murmured. “Well, that is certainly something. Ms. Jensen, why don’t you come with me to the counter and we can discuss appropriate compensation. Caroline, why don’t you take our enterprising stripper off the customer floor so no one else is offended.”

Steph took Ms. Jensen’s arm gently and directed her away from me. Caroline, meanwhile, had found another accessory in my bag to test out.

“You’ll have to buy that gag, now that it’s used. Might as well try out the matching collar, right?” Caroline reinserted my gag, and fitted a leash around my neck. She started pulling and I began to stand up, only to be yanked down again.

“You’re going to have to crawl with your outfits, cutie. We can’t have another customer seeing you in your current state — talk about offending someone! Now, if you’re obedient, Steph will just call security and let them handle you after a bit of teasing. If you’re not, well, let’s just say Steph doesn’t like bad-mannered boys. Neither do I, of course, but I’m much nicer than Steph.” Caroline tickled me under my chin as she stopped walking to open a door, and grabbed my cheeks to force me to messily pout. “Believe me, you’re not the first naughty boy we’ve had in here. Every time, they eventually give a passionate apology to the girl they offended and leave with a much sweeter attitude.” She wiggled my face from side to side. “And I know you will too!”

She directed me into a large dressing room. At one end was a wall of angled mirrors, showing different views of a slightly raised stage. Large lights adorned the mirrors like in beauty salons, spotlighting the platform. The walls were decorated with magazine covers of female celebrities and lingerie ads, all showing beautiful women in tantalizingly revealing outfits. I pulled my bags in, over my legs, still wobbling on my knees as I attempted to maintain my balance and hold onto all the outfits.

“Go stand on the platform,” Caroline commanded, “and we’ll see what kind of taste in clothing you have.”

I obeyed, struggling to stand up without falling. I looked at myself in the 3 mirrors. Apart from the bright pink leash hanging down my front and gag in my mouth, I looked like a normal male in his mid-twenties. At least I did, until Caroline wrapped her arms around me and held up one of the more embarrassing outfits I had selected.

“This one is absolutely adorable,” she squealed gleefully.

She was right. Around me was one of the cutest, most girlish dresses I had ever come across. The dress was a hot pink, ending probably around mid-thigh, while still remaining supremely innocent. The top had ruffled shoulder sleeves, puffed out and ending in a frill that popped out. The ruffles continued straight across the top of the chest, limiting any cleavage but would show my bare upper chest and any necklace. A pale pink ribbon crisscrossed down the middle to the waist, just like on the back of a corset, ending in a large loopy bow that reminded me of a ballerina. The skirt was made up of 3 layers, the shiny pink fabric extending out slightly further with each layer. Two petticoats just barely showed, one pink and one white, forcing the bottom of the dress out wide to the sides and giving it a tutu effect. Caroline wrapped the ribbon around the leash to hold it into place while she unpacked the accessories I had chosen.

A matching headband had a bright pastel pink flower attached to it, which was immediately slid around my short hair. Caroline considered a choker necklace of the same baby pink color with fake roses and tulips, trying to tug it around the existing leash, but left it aside. 3″ baby pink strappy heels sat next to my feet with similar flowers on top of the toes.

“Can you walk in heels well?” Caroline inquired. I shook my head no in response, as I couldn’t make anything by a moan.

“Now, I’ve locked the door from the inside. We have cameras on the floor, escort kayseri so we have footage of you from outside. But just to be safe,” Caroline reached into my back pocket, taking my wallet and putting it in her purse, “we’re going to hold on to this for you. Don’t try to run away.”

Caroline considered me in the mirrors, and unlocked the handcuffs. I started rubbing my wrists, but didn’t try to move. I felt the dress rustle around my chest as I moved my arms in front of me, and felt how soft the satin was on my sore skin.

“Grab the edges of the skirt, babe.” I did as I was told, and she came up to stand next to me.

“Now, for us girls, manners are very important. Why don’t you give me your prettiest curtsy?” Caroline smiled at me. “I know for very bad girls, this can be hard to do; something tells me, though, that you’ve practiced a curtsy in a cute dress before.”

I felt my face burn. She was right — and with more than one dress. I looked away from her laughing eyes and pretended to curtsy for her, spreading the skirt of my dress as I bent from the waist down, putting one leg behind the other at my ankles.

“Maybe introduce yourself?” Caroline suggested.

I swallowed my pride.

“Hi, my name is J-“

“Jessica?” Caroline interrupted. “Sissy Jessica? Sissy Jessica the slut? I’m sure you’re going to introduce yourself as a proper bad little girl from now on when you’re speaking to women.”

I looked at her meekly and complied.

“Hello, my name is Sissy Jessica and I am a bad little girl,” I pouted into the mirror and curtseyed. I felt the dress come up around me, sliding on my forearms. God, it was so silky — even the fabric turned me on. How soft and feminine it could be, how girlish it could make me feel just by being close to it. I wanted to be wearing it, to feel the air on my thighs when I stood back up.

Caroline put her arm around my waist as I finished. “Well, we have to work on your form, but you certainly have natural talent.” She rotated me to face her. “I’m confused, though. Why would such a clearly submissive sissy boy say such an inappropriate thing to another woman?”

She started running her hands along my body, and back down her own. “You should be worshiping us women. You’re lucky we even let you in a store like this, where all your girly fantasies get to come true. Am I right? Dressing up all pretty and feminine, this is something you like to do, yes?”

Caroline nodded my head up and down with her fingers, and I meekly complied. She was right. And if I didn’t nod, she could simply reach under the tiny dress to confirm with the massive hard-on I currently had.

“Well, you’re in luck. Steph happens to enjoy transforming bad boys into good girls. You won’t be her first, certainly. Or rather, she likes playing with the pretty little girls that naughty boys become for us.”

At this point, Caroline did begin to stroke my cock over the skirt, slipping in inside my jeans so I could feel the fabric. Her other hand massage my breast, constantly kneading and tickling my nipple over the dress.

“So here is part one of your punishment, at least. We’re going to finish playing dress-up, and you’re going to be a sweet, eager, proper little girl who is just excited about getting to look so pretty in pink. And when Steph comes back, you’re going to show her how much of a obedient and prim little girl you can be, ok?” Caroline increased the pressure on my cock, and I looked into her eyes in full agreement about what I would do.

I could barely hold my cock in, or believe what Caroline was doing to me. I watched myself, covered by the princess dress, a gorgeous dark-haired girl slowly bringing me to orgasm. I’d do whatever she said at this point, and when she pointed to the ground, pulling her hands away from my body, I freely sank to my knees again, ready to do whatever Caroline asked.

“Well, you will be one sexy toy for Steph. Just to make sure you don’t forget your punishment and how to properly behave, we’re going to film you getting dressed, actually. The naughty person you were earlier with Ms. Jensen — that isn’t you any more. Girls like that are focused on taking off their clothes. But a sweet sissy like you should be more focused on what we allow you to wear. Now, into the mirror, tell me what you like about the outfit, then put it on nice and slowly. Of course, your girlish excitement should be obvious: giggling, breathless, smiling, on your tiptoes, just like a pre-teen during her prom dress shopping.” Caroline stepped away, leaving me centered in front of the mirrors. “Remember, this punishment is meant to teach you to be a good girl; follow my instructions. You’re now my personal Barbie doll, sweetie. Show me you aren’t the nasty boy you were earlier by being as feminine and girlish as you can be, and you’ll be done quicker. Show me that’s what you want to be.”

I knew what she wanted. And I realized that it was what I wanted, too, in this moment. I looked at myself, a boy clearly captive and holding up the sweetest little dress. Caroline reached behind me, and undid the gag, pulling the ball out from between my lips and letting my lips come to a pout. I swallowed nervously and prepared for my girly character. Looking directly in the camera, I brought my knees together, put an arm on my hip, and put my index finger just between my lips, twirling it around as I pretended to daydream about being pretty.

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