Ya'll knew it was gonna be school girl first right?

Trent stood in a changing room in front of his biggest crush while wearing a corset, thong, high heels, and a dress. The whole situation felt surreal as he thought it through. How had he ended up like this? His thoughts distracted him for long enough that Jessica just reached over and began to pull the incredibly short dress up and off of him. Spurred into action, Trent helped her as best he could. With the tight corset and not quite being used to his newly expanded bust, he was less than useful in the endeavor.

“Damn girl, usually people don’t fight with me to get them naked!” Jessica giggled as she folded up the dress neatly and took in Tiffany’s lingerie. “Damn girl, you went full girly girl didn’t you? You got it bad for Deedee to be dressing like this every day.” Reaching out, she spun him around on his heels. Spinning around, Trent could feel his balance in the tall footwear failing him. Seeing the wall, he bent over at the waist slightly and shot his hands out against it to keep himself from falling.

Jessica giggled at the ass he presented to her. “Damn girl. I didn’t even have to tell you to assume the position!” Her hand whipped out and playfully slapped his round ass. The flesh jiggled pleasingly as she watched it bounce around. “You got a booty on you babes.” Reaching up, she swiftly began to undo the knots. Trent heaved a sigh of relief as he felt the corset’s crushing grasp begin to slowly fade away. Once she had divested him of the black lace corset, Jessica folded it and set it on top of the dress he had worn in.

Turning back to see him still standing there with his ass out and his hands against the wall, Jessica slapped his ass again. “Stand up babes, we don’t have time for that!” Standing up quickly, Trent realized what it would look like with him leaning up against the wall like that wearing only a thong and the high stiletto heels he had on. Hoping that he could get a few minutes outside of the shoes, he sat down on the chair and reached down to slip the shoes off.

“Nope! None of that Tiffany. You need to model these in heels, or else we won’t get the full effect. We can pick you out a cute matching pair after we narrow it down. Now, get those panties off, there isn’t anything there I haven’t seen before.” Jessica stood there with her hands on her hips and one hip cocked to the side. “Chop chop.”

Standing slowly, Trent could feel his hands start to shake as they reached up and hooked into the sides of the miniscule panties he had on. Squeezing his eyes shut so he didn’t have to see Jessica’s face as he revealed the locked cage, he dropped his panties to the ground and stepped out of them as they lay pooled up around his high heels. “Wow, that is so cute and tiny! Nothing like Deedee’s.” Trent’s eyes shot open as his hands moved to hide his genitals. The fear and humiliation on his face was evident as he stood there frozen.

Looking up, Jessica saw the hurt in the young man’s eyes. “Aw Tiffany, baby, I’m sorry. I thought you would like that. Please please, you have to forgive me.” Tears began to form in Trent’s eyes as his crush just accidentally eviscerated his masculinity. It became worse when she wrapped her arms around him to try and comfort him. “Shh, baby, shh. It is ok.” Wiping away the tears before they did too much damage to Tiffany’s makeup, Jessica stepped back.

“Let me go see what is taking Ana so long.” Trent nodded and closed his eyes again, praying that the world would end his suffering. Of course that meant that he completely missed Tiffany gathering up his clothes as she exited the changing room. The anguish at what had just happened washed over Trent as he stood in a women’s changing room naked and wearing high heels that his feminized father had made him wear. The worst part was, his dick was as hard as the cage would let it be. Trent stood there and waited with nothing to distract him from the thoughts and feelings that his humiliation generated.

A few minutes later, someone stepped into the room with him. Opening the eyes he had sealed shut so he didn’t have to see himself in the full length mirror, Trent was surprised to see Ana and not Jessica. Ana’s smile was soft as she spoke to him in a hushed tone. “It’s alright Tiffany. Don’t worry about it. Never be ashamed of who you are. That is the first rule of dressing like a stripper.” She chuckled as she stepped up and slipped finger under his chin. Lifting his gaze up to meet hers, she spoke again. “Now, here. Let’s get you dressed in this and see how it fits ok?”

Pulling out a tiny pleated tartan skirt, she kneeled down and opened it up for him to step into. Realizing he had and that anything he did now would only draw more attention to him, he stepped into the micro skirt and let Ana slide it up over his hips. “See, fits you like a dream. Hides that cute little bundle you got too,” Turning around, she missed the pang of humiliation that shot across his face as yet another woman called his caged package tiny.

Helping him get the top on was slightly less humiliating, but entirely more distracting as it was impossible for her to do so without rubbing up against one or both of his sensitive nipples in the process. The crop top halter top had a keyhole cutout to emphasize his aforementioned titties. Pulling them up and acting almost like a bra, the top made an impressive chest, even more attention grabbing. The last piece of the obvious school girl costume was a small tartan colored tie that hung down and rested in the valley of his breasts, but didn’t quite make it down to his belly button.

Pulling open the curtains, Ana stepped out only to look back and see Trent frozen in place. “But like, I’m, like, can’t we like, do it in here?” The edge of the microskirt just barely passed his cage. “Like, what about panties?” Trent hated to ask such a thing, wanting nothing more than to never put another pair of panties on. Yet with the length of the skirt he felt like he had at all.

“Oh sugar, don’t you worry. It is just the three of us alright? We both have already seen it. Just come on out and let us get a good look at you in the good lighting out here. Not to mention, I can’t sell used panties so I can’t have you trying them on hun.” Ana reached in and pulled Trent out onto the shop floor. His breast bounced around in the tight top, the feeling of walking around without a corset on completely different than he was used to.

Tiffany's school girl costume

Seeing that he had exited the dressing rooms, Jessica made her way back towards them. Her eyes grazed over Trent as she cocked her head from side to side. “I like this, the little play on the fact that Deedee is a cradle robber. It is cute! Put on some Mary Janes and call it a day.” Ana nodded along with everything Jessica said. Just as Ana was about to say something else, a beeping sound went off as four girls swept into the store.

“Ana! Bitch! Where are you?” The playful yelling came from a tall blonde girl, her daisy dukes, crop top, and flip flops giving the exact impression of a dancer who had the day off. Behind her, the other three were clearly following her lead into the store. None of the four girls looked lost in the sea of heels and lingerie, each moving to look at something different while the vocal one strode back towards the gathering in the back. “There you are! Hey, I need to order another pair of heels like the ones you sold me last week. The black Mary Janes.”

Trent winced realizing that she was likely talking about the exact style of shoe that he had apparently been about to put on. Ana chuckled and spoke up. “What happened? I know if they broke you would be in here crawling up my ass for a refund.”

The new girl rolled her eyes and walked up to a comfortable conversational distance. “Oh, some perv came all over them and then wanted to keep them. Something about wearing them at home and thinking about me.” She shook her head sadly. “I made like 500 off of it though.” Her eyes glanced across Tiffany and Jessica and she frowned. “I don’t recognize you two, you new in town?”

“Nah, I’ve lived here for a while. But Tiffany here is. She just moved in with her girlfriend next door to me.” Jessica walked up and wrapped her arm around Tiffany’s shoulder to keep him from retreating back into the dressing room. “We came in to get her something sexy to show off to her woman with.” As Jessica spoke, Trent finally realized why something had felt off about the woman in front of him. Even in her flip flops, she was taller than he was standing there in the 6 inch heels he had on.

“Let me go get those ordered, we will probably have them next week Jenny.” Ana stepped over to the computer and began to type away.

Jenny smiled over at the other two. “Sorry, where are my manners?” Stepping forward, she reached her hand out. “Hi, I’m Jenny. And you two are?”

Jessica had one arm wrapped around Tiffany’s shoulder and the other holding both girl’s purses. Using the arm around Tiffany’s shoulder, she nudged him to reach out and accept the shake. Reaching up to try and shake the girl's hand, Trent misjudged the distance. Where he had tried to give her a firm and masculine grip, instead his hand fell just short, so just the tips of his fingers fell into her palm. Chuckling, the tall blonde ran her fingers over the back of Trent’s knuckles softly. “Nice to meet you. That is a great outfit. I think it is the one NikKi wears. Yo, Nik!” Turning her head she called out across the store.

The loud shout drew all three other women to approach. All three women were stunning in their own rights. Nikki turned out to be a stunning Japanese woman, her black hair long and straight. A black tank top and a pair of pink shorts matched Jenny’s vibe. The other two were a pair of redheads. Only when they got close could Trent tell that they were actually twins. Both girls had naturally flaming red hair in tight curls around their smiling faces. Both wore blue tank tops and denim shorts.

Nikki sighed with frustration as she stepped up to the group. “Sorry about my friend here, she wasn’t raised with any manners and just yells whenever she wants.” Turning her gaze to Jenny momentarily she shook her head. Jenny’s tongue slipped out as she made a face at the dark haired girl. “Now, what do you want?”

“That’s the outfit you got last month right? How is it working? Tiffany here is trying to seduce her girlfriend.” With the attention of the gaggle of women now centered entirely on him, Trent’s breathing began to speed up.

The next few minutes would forever be locked in Trent’s mind. It seemed like everything happened in slow motion. Stepping closer, Nikki reached her hand out and lifted the front of the miniscule skirt that was the only thing keeping Trent’s modesty intact. The world froze as all four women stared at the pink cage. It felt to Trent like he was frozen in time as his body locked up. The next few seconds felt like an eternity.

Then Jenny spoke, her brash voice shattering the freezing effect. “Nikki! For fucks sake!” Nikki’s hand shot back like it had been scalded, the mini skirt falling back into place.

“Holy shit, I am so sorry. Oh my god. I was just checking to see if it was the same set I wear. There is a similar set that has different panties and I can never remember.” It was clear she held no malice and that it had been an accident. Trent finally found the power to move his body. Trying to shrug off Jessica, he finally snapped and shoved her back off of him. His high heels could not carry him back into the changing room fast enough. Turning, he searched for the clothing he had entered the store with, only to discover the room was empty. Frustration bubbled over as he sat on the cold chair, tears beginning to stream down his cheeks and ruin his makeup.