Well, of course more shopping

Suddenly, Ana came through the drapes and wrapped her arms around him. Her soft tank top began to absorb the tears as Trent sobbed into her arms. “Oh honey.” The soft words were barely loud enough for Trent to hear as he cried. Her hands slowly began to stroke his long blonde hair as she held him and let him cry some of his frustration and humiliation away. “Shhh, it’s ok.” The pair stayed like that for a few minutes while Trent released so much of the pent up emotion of the past day. Slowly his sobbing slowly ebbed away. With that out of his system, he leaned back away from Ana’s grasp.

“Like, thanks.” The valley girl tone slipped out of his mouth completely unbidden. “I, like, I needed that.” Taking a deep shuddering breath, he began to get more control over his emotions and his body.

“It is alright hun. Anytime. Now, do you wanna talk about it?” Both pairs of eyes looked up as the curtains parted and Jessica minced into the changing room. Trent shook his head to answer Ana’s question. Kneeling down next to him, Jessica reached her hand out and squeezed his bare knee gently.

With one last sniffle, he turned his head to Jessica. Realizing that he had assaulted the woman just to get away from the embarrassment, he suddenly felt very sheepish for the aggressive act. “Like, I’m so sorry Jessica, are you ok?” His concern towards her caused a sad smile to slip over Jessica’s face. Nodding, she leaned forward and placed a soft kiss against his forehead.

“Yeah, I’m good. Not the first time some pretty girl has pushed me out of the way in a clothes store, certainly won’t be the last.” Her playful tone felt slightly **** as she tried to lighten the mood. “Tiffany babes, Nikki really wants to apologize. Do you think that would be ok? If not, everyone will understand, but she feels really terrible.”

Trent paused as he tried to think the whole thing through. Looking up, his reflection in the mirror stared back at him. The mascara running down his cheeks, the slutty school girl outfit, two of the most beautiful women he had ever met were fawning over him. It was all so insane. Why was it that once he was put in a skirt and heels, that women of this caliber finally gave him the time of day? Realizing that he didn’t want the Japanese girl to feel terrible for what was obviously a complete mistake, he nodded.

Standing up, Jessica squeezed his knee again and walked out of the room. Ana looked down at him. “That’s a nice thing you are doing for that poor girl. You certainly didn’t have to let her. Do you want me to stay?”

Shaking his head, Trent didn’t quite trust his voice fully yet. “I’ll be right outside if you need me hun. I’m gonna get that other costume ready ok? We can get you all squared away so when you go home to your girlfriend you can forget all about this.” Trent’s chuckle was sad as he shook his head, knowing that nothing at home would make this any better. Ana’s exit from the changing room brought about Nikki’s entrance. Looking down at the bedraggled figure in front of her, she took a deep breath.

Kneeling down in front of him, she paused as she tried to work up the courage to say something to him. With that pause, Trent was able to really look the woman over. Her almond shaped dark brown eyes held regret as they stared up at him. Slowly, he began to notice other things about her. Her hair was so black it had that blue shine to it that can only come from a dye job. Her makeup was done flawlessly. In the store he would have said she didn’t have any on at all, but it became clear to him now that he saw her under different lighting that she was wearing the perfect amount. Before realizing what was happening, he spoke up. “Wow, like your makeup is amazing.”

The smile that greeted him at that simple statement showed just how beautiful this girl really was. “Thank you Tiffany.” Her voice was small as she accepted the compliment. With a swallow, she finally found the courage to speak up. “I am so sorry. I shouldn’t have done that. Even if…” Her eyes glanced down for the briefest of seconds before slipping back up to lock onto his gaze again. “I just shouldn’t have done that.”

The wounded girl in front of him was enough to make Trent forget about the situation around him. Seeing this stunning creature in front of him suffer was more than he was able to handle. Knowing that all it would take was some words, he smiled and spoke up. “Like, I get it Nikki. I know you, like didn’t mean to. I just…” He took a deep breath. He was about to enforce the story that Deedee had designed for him and he hated it. But if all it would take to make her feel better was a small lie that made him feel a bit worse, then he would do it. “Like, I was a total tomboy up till recently and this is all, just like, super overwhelming. I mean, like how do you even fix this?” He gestured to his ruined makeup.

Feeling the weight of the world slip off her shoulders, the young girl slumped back as his acceptance of her apology sunk in. A deep breath in and out gave her the chance to think before she spoke up and responded. “You are super brave Tiffany. Here, let me help with that.” Sticking her head back out of the curtain she yelled out to her friend. “Jenny, bring me my purse!” Looking back at the blonde hair and sun kissed complexion of the person in the chair in front of her. She stuck her head back out and shouted again. “Bring yours too!”

In no time at all, a pair of hobo bags were shoved through the curtain by Jenny. Grabbing the bags, Nikki ransacked both for makeup and went to work fixing the destroyed style that Deedee had applied that morning. In half the time it took Deedee to do his makeup that morning, Nikki had not only cleaned up and repaired his look, but managed to make it even better. To do that, she had been **** to go with a heavier night time look. Wiping off his soft cream lipstick, she handed him a tube of deep red stain. “I know this is kinda different from what you had, but trust me. If you are gonna go home and seduce your girl, this will be way better.”

Helping Trent stand, she moved to the side and allowed him to step closer to the mirror. Looking back, he could see that she had gone with a true evening look. His bright green eyes shone out from under dark smokey eye makeup, the wing of his eyeliner looked sharp enough to cut, and with the dark red lipstick the whole look just screamed seductress. Trent shook his head, his blonde hair bouncing around his bare shoulders as he took himself in. There was something there as he saw himself in the mirror. Feeling it welling up inside of him, he quickly shoved the feeling back down into the deep recesses of his psyche.

Shaking his head to ward off the thoughts. He turned back to Nikki and wrapped his arms around her. The unexpected hug threw the girl momentarily, but she leaned into it and squeezed him back. Stepping back, she smiled up at him as he stood over her. “Jessica got my number. She said you didn’t have your phone with you. So look, just text me and we can go get lunch or something. Maybe do some makeup lessons? How does that sound?”

Trent nodded, knowing he would never take her up on the offer. “Sure. That could be like, totally amazing.” Moving out of the changing room, Nikki waved bye. Listening carefully, he could hear the sounds as the foursome of women made their way out of the store. Jessica appeared a moment later. Without a word, she began to reach up and help Trent pull off the costume. In short order the slutty school girl outfit was clenched in her hands and he was once again left standing naked except for the high heels he was somehow still wearing.

Coming back a moment later, Jessica had a pair of bright red items in her hands. “This matches your new lipstick. Let’s try it.” Even Jessica, who had been unflappable, was in a much quieter mood after the girls left. Trent nodded along resignedly, just hoping to get something on his body. First the pleated latex skirt slipped up over his wide hips. Marginally longer than the school girl skirt, Trent was confused with the white lacy apron attached to the front of it. Before he could figure it out, she was helping him squeeze into the top. The red short sleeved crop top left nothing for the imagination with its low cut neckline.

Stepping back, Jessica looked him over and nodded her approval. “You look amazing!” Trent’s eyes glanced at the mirror and he couldn’t help but agree with her. The bright red matched his makeup almost exactly, while his tanned skin and blonde hair contrasted against it perfectly. Seeing the outfit fully on, he now understood the white lacy trimmed spot on the front of the skirt.

Shaking his head, he turned back to Jessica. “Don’t you think the maid thing is a little over done?”

Rolling her eyes, she didn’t even dignify that with a response and instead pulled him back out to see Ana. Upon seeing him enter the sales floor, Ana spoke up. “Ohh, I know the perfect shoes. What size do you wear hun?”

Trent froze as he realized that was an answer that even a tomboy would know. “Uh, same as Deedee?” He prayed that either her or Jessica would know what size it was, because the last thing he wanted to do was tell her his mens size. He didn’t think the questions that would bring up would be fun to go over. Luckily, that seemed to work as Ana moved off to gather the heels up. While she was gone, Jessica stepped up behind him. Moving his long blonde locks to the side, she wrapped a white lace choker around his throat.

Ana came striding back, a pair of tall red patent leather platform heels with a silver chain that functioned like an ankle strap in her hand. Only as she set them down, did he notice that the heels on the 6 inch tall platforms were a silver material to match the chain. Knowing what was expected of him, Trent stepped out of the slingbacks his father had put him in and sat down on a nearby chair to slip into the new shoes. The feeling of the rough material on the seat of the chair brushing up against his hairless ass reminded him that he still hadn’t been able to get a pair of panties to slip into yet. So he was once again completely exposed should his skirt pop up.

Jessica grinned over at Ana as she kneeled down in front of Trent. A sad smile crossed his face as he realized that here he was, not wearing underwear, with his beautiful crush kneeling in front of him, and he couldn’t do a thing about it even if she would let him. Jessica’s hand slipped up his calf slowly as she slid the first heel on. The silver strap was chilly on his bare leg as she wrapped it around his dainty ankle. Hearing a faint clicking sound, Trent looked down at the side of the heel under the guise of seeing how they looked. The sound had been exactly what he had feared, a lock closing on the chain. By the time he had realized the situation, Jessica had already finished with the other heel.

Standing up, Jessica offered her hands to help him stand up. Taking his crush’s hands, Trent carefully stood up out of the chair. With the small one inch platform, the six inch heels **** his feet into an **** arch that was even worse than the first pair of heels he had worn, but not by much. Bringing his knees together, Trent mentally ran through the instructions he had spent so much time practicing yesterday afternoon. With one tentative step, and then another, he slowly began to make his way over to the mirror, his stride steadily improving.

Staring back at him was the sluttiest french maid he had ever seen. His eyes roamed over his body with disbelief. He had thought he was becoming used to seeing himself in this manner. That his femininity was becoming commonplace. The image reflected back at him disabused him of the notion instantly. He could feel himself becoming aroused by his own image. Thoughts of a woman who looked like this serving him drinks, and then serving him in other ways made his heartbeat quicken.

The sound of Jessica’s phone going off startled everyone in the quiet space. Not realizing what had caused the noise, Trent was afraid that another person was walking into the store and looked over as he got ready to mince into the dressing room. Seeing no one there, he glanced back at Jessica to see her reading a text message. A frown coming over her face. “Like, what’s up Jessica?”

“We need to go pookie. I know I promised more shopping, but a work emergency just came up. I need to get you home asap.” Looking around frantically, Jessica spotted the purse he had carried in and moved to collect it. Handing it back to Tiffany, she went to collect the rest of the outfit he had arrived in.

Sensing how hurried Jessica had suddenly become, Ana moved over to the register to begin the checkout process. “Tiffany, how do you want to pay for this hun?”

Trent tried to catch up to the situation that had suddenly sprung up around him. Seeing Ana at the register he walked towards her. Moving with any kind of haste in these heels **** him into a mincing gait. The bouncy walk gave his breasts and ass a reason to bounce every which way. He could hear the small silver locks on his heels click with every step as they clinked against the thick silver chains.

Stepping up to the desk, he reached into the purse he had been given and began to look for any sort of card or cash that Deedee might have slipped in there. Of course all he found was the feminine products he had seen before and his oversized cat’s eye sunglasses. Looking over to check with Jessica, he could see that she was now on the phone. Her conversation sounded clipped and urgent. Seeing that she would be of no help, he turned to Ana. “Um, does Deedee like, have an account or something?”

“She does, but I can’t just let you use it without her authorization hun. I know Jessica said you were her girlfriend, but I can’t risk it.” Trent’s sigh of frustration and impotence tugged at Ana’s heartstrings. “Can you call her? Or I can call her on the store phone?” Seeing a way out of the sudden predicament, Trent nodded quickly.

Dialing the number in the database, Ana’s voice was much more professional when he heard Deedee pick up. “Hi Deedee, this is Ana. I have a girl named Tiffany here and she wants to make a purchase using your account. The total would be $215.12” She paused as Deedee responded. Trent could hear Deedee’s voice, but not what she was saying. “Uh huh.” Reaching out with the phone in her hand, she offered it towards Trent. “She wants to talk to you hun.”

Trent tried to smile as he reached out and wrapped his hand around the phone. “Like, hey.”

“So, what are you buying baby-girl? Something for me, or something for yourself?” Deedee sounded pleased to hear from him. Her voice held a note of huskiness to it that Trent did not expect.

Hearing giggling in the background of the call as he went to respond, he suddenly remembering that his girlfriend had been at the door to his father’s house as they had left. “Like, something for me. Um, like, is that Brittany I hear?”

There was a soft chuckle that came through the phone into his ear. “What was that babe? Oh, Brittany? No, the girl who showed up here earlier is long gone.” Another giggle followed Deedee, clearly the sound of another woman in the background.

“Like, uh, ok. So, like, can I get the stuff?” Fear was beginning to take its toll on Trent as his mind conjured up a million horrible possibilities. He wanted to believe Deedee, but something told him that she had just lied to him. Knowing there was nothing he could do about it at the moment, he decided to try and move forward with the purchase just to be able to get home quicker.

“Sure hun, hand me back to Ana.” Reaching out to take the receiver from Trent’s hand, Ana listened for a moment then began to type away at the computer.

“Bye.” Ana’s reply to whatever Deedee had said was short and to the point as she hung up the phone. “Ok girly, you are all set. Now, let’s get you changed.”

“No time for that.” Jessica’s voice cut through to both of them as she strode up to the counter herself. “I need to leave now. Hand me bag up her other things please Ana?” Turning to Trent, Jessica’s face was crestfallen. “Look, can you please just go with this. I really need to get going. My boss Rachel just hit me up and I have to get to work, like yesterday.” Waiting for his response, she quickly placed his previous outfit into it, shoes and all.

Trent tried to think of any possible option that did not involve him walking through the mall in this outfit. Looking to Ana for support, he could see concern in her eyes, but she also seemed unable to offer any help. Chewing nervously on his bright red painted lip, he thought about taking an uber. The realization that his phone was missing so he wouldn’t be able to call one came a short moment later.

“Please?” Again, Jessica used the patented pout on him. Closing his eyes, Trent reached into the purse and slipped the large sunglasses over his face, hoping that they would provide him with some anonymity. His actions made it clear that he would do as she asked. Reaching over to take the large white bag from Tiffany, Trent held it in front of him to try and give himself some semblance of coverage from prying eyes.

Grinning from ear to ear, Jessica hugged him for a moment before heading directly for the door. “Thanks Ana! You are the best!” Ana’s response was lost in the sounds of the mall as the pair began their quick march through the crowded space. Trent knew that one of the important instructions Deedee had given him for walking in his heels was to keep his chin up, but the feelings of his body as parts of it bounced around every which way combined with the feeling of being nearly naked **** his gaze down to the ground. His cheeks burned red as he did everything he could to get out of the mall without being noticed.

Still, the trip to the parking lot went surprisingly well, until the very last moment. Just as they stepped out of the doors, a voice cut through his thoughts. “Dayum, ya’ll look good.” A group of three young men happened to be walking into the mall at that exact moment. Trent’s eyes shot towards them and his worst fears became realized.

Standing in front of him were three of the people he had graduated highschool with. Darren, Colby, and Eric were all kids he knew and who knew him, but were not what he would have called friends. Even as he recognized them, the three boys moved to intercept Jessica’s path to the car. “Where you going so fast babe, I’m right here. No need to go lookin for Mr. Right, I’m Mr. Right now.” The chuckles from the other two only spurred Colby forwards.

Trent’s eyes rolled behind his sunglasses at the trio’s actions. All three of the rich white boys had spent all of highschool trying to portray themselves as thugs from the hood. Still, the fact that all three had been on the football team and came from money meant they had enough hangers on that no one had ever confronted them on their style and speech. Jessica’s voice was less than forgiving as she spoke up. “You look like more of a Mr. Right Hand I think.”

Colby’s face turned red as the anger and embarrassment from the cutting remark hit him square in the ego. “What did you say you skanky bitch?” The loud words of hatred sent a shiver through Trent as he realized just how **** both him and Jessica were at that moment. All three of these men could have beaten up Trent, let alone high heeled wearing Tiffany.

“Ladies, do we have a problem here?” A confident masculine voice rang out, stopping Colby in his tracks. Stepping out of the doors, the hulking forms of the security guards Steve and Jimmy became visible. “Jimmy and I would really hate to have to do the paperwork on a problem, wouldn’t we?” Jimmy’s only response was to cross his massive arms across his chest and grunt in affirmation.

The three youths slowly began to back away from Trent and Tiffany. “Nah man, no problem here.” Eric’s voice spoke up as he moved over to push Colby back. “We were just on our way inside and ran into these two. No reason for anyone to get involved.” Eric guided Colby and Darren through a door farther away down the wall.

Trent’s eyes tracked them until they disappeared through the doors. Heaving a sigh of relief he turned around to see Jessica already stalking off towards her car. Her voice rang out. “Boys, typically I would be so down to thank you personally, but I really need to get going.”

Trent could see the recognition appear in Steve’s eyes as their gazes met momentarily. “Let us walk you to your car at least then?” Motioning for Tiffany to move forward, Steve spoke up as the group headed across the open lot. “We keep running into each other like this and one might start to think it was fate.” He chuckled softly as he walked along beside Trent.

“Like, yeah, fate or something.” Trent was completely distracted by knowledge that guys he had gone to highschool with had just seen him dressed like this. Even though they hadn’t recognized him, it had been a close thing. “Thanks for showing up though, you totally saved us.”

Both men grinned as they finally approached Jessica’s bright pink Mustang. “All in a day’s work.” With Jessica and Trent safely in the car, the security guards headed back inside as Tiffany put the car in gear and sped away.