I think we have more important things to worry about

It was hard to miss the moving truck out in front of the house across the street that had not been there when they had left. Jessica’s car swerved between it and the white car that still sat parked in front of Deedee’s house. The pink Mustang came to a halt at the edge of the sidewalk in front of the driveway, “Super fun shopping trip babes. Sorry it got cut short. But when Rachel calls, I come.”

Recognizing the name of Jessica’s boss, Trent nodded in understanding and opened the door. Carefully pulling himself out of the car, he did his best to make sure that he didn’t give anyone a show. Trent barely managed to grab his purse before the door closed as Jessica’s car shot off into the distance. Standing there watching her drive down the road, Trent shook his head, never having seen Jessica so flustered.

Looking up, he realized that he was most certainly not alone on the street. With the moving truck, came movers. The large young men had all stopped to stare at the long legged latex clad beauty that stood in the street. Before he could turn to run into the house, a woman’s strong voice rang out. “Boys, do you think we could keep moving? The pretty girl isn’t there for you to ogle.”

Trent turned his gaze to see who the voice belonged to. The beautiful redheaded woman stood there, clad in a pair of leggings and an oversized crop top. Her hair was bundled up in a Rosie the Riveter style bandana with just her perfectly trimmed bangs showing. Even in the obvious moving clothes, her hair was clearly done up and Trent could see more than a hint of eyeliner. With a wave she shouted out across the street and apologized for the men. “Sorry about that hun. You know how they can be. Love the outfit!”

Trent waved back reluctantly to her parting form as she walked inside her house.The men grumbled at the orders but bent themselves back to work. Seeing that he was relatively free of the stares, Trent turned and quickly click clacked his way up the driveway. With the distraction caused by Jessica’s haste and being visually devoured by a handful of men, Trent only noticed Brittany’s car just as he reached the front door. Laying his hand on the knob, he paused before turning the handle. His mind began to spin up all the possibilities of what he would find inside. Thoughts of how Brittany would react to seeing him like this froze him in place. With the woman having been gone for a moment, a catcall rang out from across the street and galvanized his decision to open the door.

Before he could act on that decision, the handle was stolen from his grip as the door opened up in front of him. There standing in front of him was the very girl he had feared to see just seconds ago. Only, this wasn’t quite the girl he had expected. Standing in front of him was a more grown up and sexy woman. When he had seen her before she entered the house that morning, she had stood in his exact spot as the meek girl he had been dating. Instead, perched on a pair of purple heeled sandals that laced up the ankle with a wide satin bow, was a more mature, more glamorous vixen. His eyes traveled up from the heels and saw her nylon encased legs. The light reflecting off of the hose brought out every curve. The black mini dress she had on was the precise definition of a classic little black dress. The capped sleeves and a square neckline worked perfectly for Brittany’s girl next door looks.

The pair of feminine figures locked eyes on one another. A hint of what could have been recognition began to appear on Brittany’s face, her eyebrows knitting together in thought. As she opened her mouth to speak, Trent responded in the only way he knew how that might postpone his being outed to her. “Like, hey! I’m Tiffany.” Sticking his feminine hand out, he tried to remember how women shook hands. His other hand clenched at his purse in tight grip as he silently prayed she didn’t recognize him.

“Oh! Well that explains it! Hi, I’m Brittany.” After realizing who this familiar looking woman was, Brittany’s smile lit up like a ray of sunshine on a cloudy day. Reaching forward, she grasped Trents hand. Brittany’s tiny hand looked far less feminine when compared to the exquisitely manicured hand of Trent. The brief handshake allowed Brittany a chance to look over Tiffany in her own inspection and comparison. Her eyes widened as she realized just how tall the heels the other girl had on were. Then her gaze took in the tiny red skirt and crop top combo, quickly realizing that Deedee’s girlfriend had come home to surprise her with some fun times. “Wow, you look amazing. Well, I don’t want to interrupt.”

Tiffany’s outfit

Stepping past Trent she giggled and stage whispered to him. “Don’t let her work you too hard!” Trent watched Brittany walk away, slightly unsteady on her four inch stilettos. Two things came to him as he watched her walk. The first was that he did not think he had ever seen her look sexier. The second thing he noticed was that not only did he now manage to walk in heels better than his girlfriend, but his were also higher than hers. The fact that his outfit was a magnitude sluttier only made the whole comparison between the two that much worse. Deedee’s voice floated past him as she walked up and took his hand in hers. “Britt baby, heel toe, chin up!” The responding enthusiastic wave from Trent’s girlfriend as she slipped into her car was friendly. Deedee turned her attention back to the display of sexiness that had been delivered to her door. “Well, that is certainly worth the price of admission.”

Trent stood frozen in place as he felt emotionally crushed between a rock and a hard place. The fact that his girlfriend Brittany, he refused to think of Deedee as his girlfriend, had completely mistaken him for a woman hurt his pride in unspeakable ways. However his elation at not being discovered lifted a weight that had settled onto his shoulders earlier that morning when he had first realized she was at the house.

Pulling Tiffany inside, Deedee closed the door behind him and took her time looking over Tiffany as he inadvertently modeled the outfit she had paid for. Her eyes immediately went to the bright red latex outfit and locking heels, but her curiosity became piqued as she noticed the new makeup look he sported. Reaching out she ran her nails over the exposed skin of his tight stomach just beneath his crop top. Trent could feel the touch like soft coals running along his skin. The feelings that her touch inspired added to his emotional exhaustion. With so many feelings attacking him from every different angle, he found it harder and harder to control himself.

Deedee stalked around behind Trent, her fingertips grazing across his skin. He stood there, feet together, hands clasped in front him holding his purse. He was like a deer in the headlights before her penetrating gaze. She slowly traced her nails around to his back, and slowly down towards the curve of his plump ass as she inspected him like a prized cut of beef. In a playful tone, she addressed the question that had been on her mind all day. “So tell me baby, were you a good girl for Jessica and Ana?” Leaning in, her lips brushed against his ear and her voice took a darker tone. “Because I know you were very naughty before you left the house today.” Standing up, she pressed her body up against him from behind, one arm going around Trent’s waist, the other slipping around his shoulders as she pulled the two of them together.

The feeling of Deedee’s warm and soft skin against his sent a jolt of heat up his spine. His sharp intake of breath came not just from the pleasure of her touch, but in the myriad of other thoughts that spiked into him suddenly. Knowing exactly what she meant about being a bad girl, his mind went back to the thoughts of his earlier refusal of the plug and doubt crept into his mind if it had been the correct choice. The doubts began to push more questions towards him that he didn’t want to answer. Had it truly been that bad the day before? The feelings of fullness and it bouncing around inside of him had given him small jolts of pleasure after he had become used to the plug being buried inside of him. The spiral of thoughts continued down as he began to question why any of this was stoking the fire of pleasure that was slowly beginning to build up inside of him.

The thoughts roiling along in his mind took up all of his concentration. Even though Deedee could not see his face, she could tell that he was **** to answer. With his continued silence, she continued her interrogation. “No excuse for that? Interesting. I expected at least a small token resistance. Some excuse about not seeing it at least. Anything at all to stand up for yourself. Or are you already gone?”

Trent’s eyes shot up as he stared across the living room, his plump lips parted in surprise at the accusations of weakness. Pulling in a sharp breath finally allowed him to wrest enough control of his emotions to respond. “Like, I thought, like…” The condescension he had heard in her voice made the powerlessness in his that much more apparent. Suddenly, his mind shot back to the moment in the store earlier. The continued humiliation of the day built to the point that he had **** but to apologize. Hoping that it would mollify Deedee as it had everyone at the store, he spoke softly. “Like, I’m sorry Deedee.”

“Are you now? Tell me Tiffany. What are you sorry for?” The scorn in Deedee’s voice was not entirely fake. Internally she was beside herself with how little effort her son was putting forth to defend himself. Having only her own experience to fall back on, she assumed that Trent would have continued to kick and scream. The lack of fight was fueling that seed of anger in Deedee that had blossomed while speaking with Brittany.

Unable to keep his eyes aloft, his gaze drifted down to the floor as he tried to think of what it would take to appease her. He needed to find something else, to take the apology farther. An idea came to him and he knew it would work, what he didn’t know is if he was able to say it out loud. “Like, I was a…” He knew what she wanted to hear, but he just couldn’t bring himself to say the words. He couldn’t bring himself to become that yet. “I totally ignored what you said. I’m sorry.”

Deedee’s eyebrows raised as she considered what he had been about to say, even as he backpedaled from it. She worked that hesitation around in her mind, realizing that she may have finally found the place he would begin to take a stand. Still, she was amazed at how quickly Trent had almost gotten there. It had taken months before she had even come close to saying those words to Miss Jameson. “I see.”

Trent desperately wanted to understand what she meant. Even though he had not said exactly what Deedee wanted, he had expected much more of a reaction to his apology. Back at the store that morning, Nikki had melted and accepted him the moment he had uttered the words. Ana had praised his bravery for it, and even Jessica had acknowledged it in her own way. Thinking about the fact that Jessica had been among the women he had been exposed to, he was surprised he could feel even more shame than he had in that moment. His focus on Jessica brought a small thought to the surface, a thought that was buoyed by his refusal to completely break to Deedee’s will. How had Jessica known to tell Ana that he was like Deedee?

Before Trent could pull that thread of thought far enough to see the end of it, Deedee reached her hand down to grip the purse in his hands, she ripped the straps from him and tossed the handbag to the couch. The sunglasses soon joined it. Deciding that she had pushed that angle as far as she could, Deedee tried something different. “So I won’t hear any stories from Ana or Jessica about you behaving poorly on your trip? Nothing that might have happened to make you seem like anything but the perfect little girlfriend?”

Trent had to push all of the jumbled thoughts to the side as Deedee continued. He knew that while he would have to address many of those questions later, it was not that time. Thinking of her latest question, he focused on her emphasis on the word girl. It was clear to him that she had been made aware of what had happened and wanted him to tell her about it. It was also clear to him that he never wanted to talk about it again.

Trent’s lack of response **** Deedee to up the ante. Snaking her lower hand down his right leg, it slipped over the latex of his skirt and landed on his bare thigh. Once clear of the miniscule garment, she slowly moved it back up under the skirt. Deedee could feel her own arousal become apparent as she pushed herself past yet another moral and sexual boundary. Trent’s breath caught in his throat as he felt her hand move under his skirt. The stray question in his mind of when he had started to think of it as his skirt was quickly washed away by Deedee’s hand cupping hairless balls and tiny pink plastic cage.

“I’m sure a smart girl like you has figured out that Jessica already told me all about it. How you flashed those strippers your naughty little clit.” Deedee’s eyes were closed as she held him tight against her. The scent of her feminized son invaded her mind as the feelings of lust drove through her. She could feel herself slipping farther and farther down a path that most would consider evil. Yet, she could feel that it was the right path for them to take.

Indignation finally brought his voice back as Trent rose to defend himself. It had been nothing like what she had just described. More questions about Jessica’s loyalty arose in his mind as he spoke in that air headed accent. “Like, that’s not what happened. Nikki fully grabbed my skirt. I didn’t flash them. Please Deedee, you have to believe me.”

Deedee’s giggle in his ear surprised Trent as her attitude once again made a hard right turn. “Oh baby, I know. I just wanted to see what you would tell me. I wish I hadn’t had to drag it out of you.” Her voice held a playful tone as Deedee punctuated the word ‘drag’ by gently pulling against his cage. “I wish you had felt like you were woman enough to stand up and tell me about all your slutty escapades.” Her tongue flicked out against his ear, causing a tiny moan to well up from his throat. “But would you like to know what is really surprising me right now?”

Not trusting his voice, Trent simply nodded as he prayed that if he went along he could get out of her grasp. “What is really surprising to me, is how wet all of this is making you.” Her hand under his skirt rose up in front of them and revealed the damp residue of his leakage on her palm. Her teeth nibbled at his ear briefly before she continued. “You actually like this, don’t you?”