Shopping? Count me in!

Meanwhile at the mall Trent’s feet were already starting to hurt, and they had only just crossed the parking lot. Trent shivered in his short dress as he and Jessica crossed the threshold into the mall, the air conditioning shooting down at the pair of them. The sounds of two pairs of high heels strutting through the mall on a Saturday morning drew a number of people’s eyes to them as they began to make their way in amongst the shops. Trent could feel the gazes of men as they traced over his body. He shivered again for an entirely different reason then before and turned to speak to Jessica as she strode through the space confidently.

“Like Jessi? Do we have to do this? I like, I want to hang out with you. But not, like…here.” Inwardly he cringed at the way that he was speaking. It almost made him feel like his IQ was dropping just from the way he had to think to phrase things. Not only that, but he hoped if he could get Jessica somewhere private he could figure out how to get her to take him back home. The last thing he wanted was Deedee and Brittany together.

Jessica giggled and just kept right on walking along. “Don’t worry your pretty little head Tiffany dear. We won’t be too long. I just think it would do you some good to give Deedee some space. I can tell the poor dear is just so stressed right now.” Trent followed along, not wanting to be left behind dressed as he was. He couldn’t help but shake his head as heard Jessica mention how stressed his father was. The corset crushing his ribcage at that very moment was more stressful than anything Deedee was dealing with at that moment.

“Like, you are so sweet.” He knew he had to keep playing the part of the ditzy blonde valley girl. Deciding to try and take a different tact, he switched to another topic. “So, like, you said yesterday that you used to interact with Trent a lot? Like, what was he like? Was he cute?” He hated the way it sounded when he asked that last part, but he had always wanted to know precisely what Jessica thought of him. As odd as the situation was, he had the chance to get her unvarnished opinion of him.

Rolling her eyes, Jessica stopped for a moment to look at a dress in the window of a boutique. The pink mini dress seemed to take her attention for a moment before she seemed to discard the garment and continue on. “He was a boy. Not just in the fact that I’m sure had a peepee between those legs, but more in the fact that he wasn’t a man. He was never going to be a man either. Deedee loves him, but she spoiled him rotten.” Stopping in front of another mannequin, she appraised it through the front of the store as well. “I mean, can you believe I would invite him over all the time and he never once tried to do anything with me? He never kissed me, never even asked me to coffee or something else lame like that.”

Trent’s eyes almost bulged out of his head as he listened to his crush go on about him. Thankfully, she was continuing to judge the soft green dress in front of her, instead of looking at him. His mind shifted back to all the times that he had tried to ask her out, all the times he felt like he had tried to kiss her. Each time had been rebuffed so politely, so adeptly, that he had never felt fully rejected. Anytime he would try for a kiss, her head would slip to the side and he would kiss her cheek. Everytime he would ask her to do something like dinner, she would just assume he meant as a family or with her friends. All thoughts of Deedee and Brittany being alone together disappeared as he tried to defend himself. “I’m like, sure that he did those things. Like maybe you didn’t notice?” Fidgeting with his purse and moving from one heel to the other, he tried to give his aching feet a break.

Jessica’s large breasts bounced as she shrugged and wrinkled her nose, finally mentally discarding that outfit as well. “Maybe. Honestly though? I think he’s gay.” Turning on her heel she looked up and squealed. “Ohh, Saks!” Her free hand reached back and wrapped itself around Tiffany’s wrist before she hot off like a high heeled rocket. “I heard the new 2024 fall and winter stuff is in!”

Trent struggled to keep up in his heels as his brain tried to wrap around the fact that Jessica had just said she had thought he was gay. He couldn’t understand how she would say something like that when he had spent so long trying to have her help him find a girlfriend. All during highschool she had been the one he had gone to for advice. The sound of the two pairs of heels clicking off the hard tile floor was making it hard for him to think. “Like, wait!” Trent had to **** her to stop suddenly so he could ask her what she meant.

Jessica stopped, surprised, and looked up behind the feminized man. Giggling, she shrugged as she spoke.. “I mean, if that is the kind of shopping you want to do, that is all you had to say hun. We are sex positive up in this bitch!”

Trent’s sculpted brows rose as he struggled to realize what she meant, until he saw where her eyes were pointing. Turning his eyes took in the small boutique that Jessica was walking up to. The simple sign above the store read ‘Ana’s’. Confused as to why she would react like that, he followed Jessica as she pulled the solid door open. Unlike most stores in the wide open mall, this one had a closed frontage along with its opaque solid door that customers had to open to get in. The one thing Trent did notice before following Jessica inside was the sign next to the door that read ‘18+ only’.

Trent did his best to keep any sign that his stomach was flipping in knots hidden as he moved up next to Jessica and looked around. Fear settled into his heart as he realized the trap he had just accidentally sprung on himself. Stacked along the walls was lingerie in all forms and shapes. The back wall was dedicated to high heels, although none as expensive as his father’s collection. Dominated instead by clear lucite platforms, he realized that he had just inadvertently asked Jessica to take him shopping in a store that catered to strippers and gogo dancers. “Like, oh, my, god.” The words came out in a whisper as he stood there, all questions about his sexuality driven from his mind.

“Isn’t it amazing! Ana moved it in last year, apparently there was an opening here and she is friends with Ashley at the salon. So Ash got her a smoking deal somehow.” Moving off away from the frozen in place Tiffany, Jessica began to look through the racks of lingerie, costumes, booty shorts, and general stripper attire. “I’m surprised you knew about this place, they did a really good job of keeping it on the DL. Mostly only dancers know about it.” Pausing, she looked up from the pink PVC shorts in her hands. “Wait, are you a stripper?!” The question came out in a squeal of excitement.

Looking down at the floor, he tried to hide the blush that crept across his cheeks. He couldn’t believe that the woman he had crushed on for years thought he could be an exotic dancer, and not the kind from Chippendale’s. Staring down at the floor, his large breasts came into view. The fast walking and stress of the situation had his chest heaving in short shallow breaths as he tried to deal with the infernal corset cinching his waist down. “No, I could never do that.” His voice lacked the valley girl accent that he was trying to keep up, but instead had become so meek and soft that it still had a feminine quality to it.

Stepping back up to him. Jessica wrapped her arms around his waist and pulled him into a crushing hug. The scents of her perfume and her leather dress assaulted his senses again as she pressed her body up against his. He could feel his caged dick trying to come to life as she held him. “O, M, G, you could so do it. You are totally hot, and those legs? Come on!” Trent couldn’t believe this was happening. His crush had her tits pressed up against him and was trying to comfort him, and he could feel his locked cage making it completely pointless.

Another voice broke in and interrupted the pair. “She really could. She puts a number of the girls that come through my doors to shame.” Trent swallowed as he looked up at the woman who had just said he would be pretty enough to be a stripper. The brunette walking up to them was a middle aged woman, likely a few years older than Deedee. She still radiated beauty in a different way than Jessica’s girl next door turned pornstar, or Deedee’s corporate MILF energy. This was a woman who knew exactly how beautiful she was and had no problems with it. “Hey Jessie.”

“Ana! I swear, I was gonna come find you in a minute. I def wasn’t just looking through your new stuff without saying hi.” Tiffany set the hanger that held the pair of shorts she had been looking at down in a completely different spot than she had picked it up from. Stepping back, she pulled her body away from Trent and introduced the women. ”Tiffany, this is Ana. Ana, this is Tiffany. She is fucking awesome. Her and Deedee are dating.”

Ana’s eyes sparkled as she looked Trent over. Her deep brown eyes seem to devour him and expose every secret he had. Trying to shake the feeling, and not wanting to get caught staring at another woman after just having his fake relationship outed like that. Trent smiled and nodded. There was something about the older woman that drew him in, and he couldn’t quite put a word to the feeling.

Chuckling softly at her friend’s antics, Ana reached down and collected the pink booty shorts, moving away to put them back where Jessica had collected them from. Watching her replace the clothing, Jessica spoke up again. “Me and Deedee know Ana here through Ashley. Ana used to be a dancer, but then she retired and started this place.” Jessica couldn’t stop a giggle. “Now she puts clothes on other people!”

Ana’s exasperated sigh was one of long standing sufferance. “That joke never gets old, really.” Stepping up to Tiffany she began to look her over. “So if you aren’t a dancer, what can I do you for then hun? You look a mite bit classier than most of the girls that come in here and wear my stuff. Present company excluded of course.” Jessica giggled and waived off the insult as if it was expected. Jessica moved away farther into the shop, her attention grabbed by some other sparkly outfit.

Speaking over her shoulder as she searched the racks, Jessica explained why she thought they were here. “She and Deedee just started dating. Deedee has all that work stress, and this dumb thing with her stupid kid, and she just needs something to take her mind off of it. And Tiffy here used to be a tomboy so she doesn’t have the saved up sexy outfits like the rest of us. You think we can find something to help her make Deedee’s day better?” Jessica’s voice interrupted any chance that Trent had to tell Ana that he didn’t need or want anything from this store.

“Oh, I think we can find something!” Ana laughed softly and stepped up close to Trent. The ex-dancer looked up into his eyes and smiled. Trent could catch the smallest hint of a southern twang in her speech as she continued on. “So tell me hun, what do you want to do for your girl? Give her a lap dance? Maybe do a little roleplay?” Trent stood frozen as thoughts of Ana giving him a lap dance began to make the cage in his panties more than a little uncomfortable.

Jessica piped up again, not letting him have a chance to voice his own opinion. “Ohh! Roleplay, roleplay!”

Ana nodded and smiled, reaching out to touch Trent’s arm softly. “Don’t you worry your pretty little head hunny, We will find you the perfect outfit so you can make that girl forget all her problems.” Winding her arm through his, she began to lead him over to one of the walls in the back of the store. Trent followed along, completely unsure of the best way to extricate himself from the situation.

As soon as they got back to the wall of costumes, Ana separated from Trent and looked through the array of costumes in front of them. Before a single suggestion could be brought up, Jessica’s voice drifted over from a different part of the store. “Ohh! Ana, she is a special girl. Like Deedee!” Trent tried to think of what would make him special like his father. Eyes suddenly going wide he realized that Jessica had meant that he had not been born a woman.

“Jessica, like stop it!” Just barely remembered to use the valley girl accent, he yelled at Jessica in frustration. His gaze shot around the room in wide eyed fear as he tried to see who could have heard, he began to relax a bit more as he realized that it was only the three of them standing in the store. Calming his voice down, he tried to find a way to stop all of this. “Like, maybe this isn’t the right time for this.”

Taking his **** for nervousness, Ana’s soft hand grasped his bare elbow softly. Trent looked down into her eyes and saw the gentle soft smile on her face. “Hun, you have nothing to worry about here. I will protect you from mean ole Jess ok? And Jessica, you be nice to this girl or I’m gonna take away your discount!” Ana yelled the last over her shoulder. The panicked squeak as her face popped up over a rack of clothes made it clear just how threatening that actually was to her.

“Sorry babes! I just figured you wouldn’t tell her, and it could make some of the costumes not work as well.” Jessica minced over to him and wrapped her arms around him in a big hug. “Really Tiffany, you are amazing, way better than that Trent kid ever was.” Jessica's eyes went wide for a moment as she realized what she had just said. In an attempt to distract Trent from why she would say that sort of thing, she leaned in and kissed him softly on the lips.

The pairs of pink puffed up lipstick covered lips pressed against each other softly as Jessica kissed him. It felt like the cage under his skirt was shrinking as his body did its best to show just how excited he was at the touch. Sighing as she broke the kiss, he spoke up softly. “Like ummm, thanks.”

Stepping away like the brief kiss had meant nothing, Jessica looked over at the wall of costumes to find something she liked. Ana’s voice was soft as she stepped back up next to Trent. “That girl is crazy, but she really does have a big heart. Don’t let her stress you out too much honey. I can tell you are kinda that sweet soft type. I can see how you and Deedee are perfect for each other. She has been needing someone soft in her life that she can take care of.” Trent’s face blazed red as he listened to this woman describe him as the perfect submissive woman for his feminized father.

Unable to think of what to say, he just nodded and chewed on his bottom lip. His mouth quirked up into a soft smile as he realized he could still just barely taste Jessica’s lipstick. Taking his nod and smile as acceptance to move forward Ana looked him up and down again. “Perfect, I know exactly what we do. I’ll pick out four choices, then you can try them on for us ok? We will pick out the best one for you to surprise that girl with.” Not even waiting to see if he agreed, she stepped away and began to gather different costumes. “Jess! Quit browsing, you already own everything here! Take her into the dressing room and get her started. Cause unless I’m mistaken, that girl has a corset on, and you know full well none of these will work with that.”

Jessica’s hand shot out and wrapped around Trent’s wrist instantly. As she pulled him along, he pulled back and tried to separate the two of them. The dressing room was the last place he wanted to be with anyone right now. Surprisingly the blonde bombshell’s grip was unbreakable, and her ability to walk in the high heels far outshone his, making it impossible for him to stop her. “Jessica…”

“Now shush. What Ana says, goes. Plus, think about how happy it would make Deedee if you did this? I’d hate to have to go back and tell her that you weren’t acting like the perfect little girlfriend.” Hearing that phrase made Trent’s resistance fall away. He knew that this was going to be humiliating and stressful, but at least it was just the three of them. Who knew what kind of horrors Deedee would think up for him if he didn’t do as she had told him. Following Jessica back, the two of them crowded into the first of three different dressing rooms.

“Ok, strip!”