Let's find out how bad this is.

The quiet hum of the restaurant enveloped the pair as the door closed behind them. Deedee’s eyes swept across the room as she tried to spot her date or Miss Jameson. A deep breath of relief tinged with a bit of anxiety escaped her lips as she finally spotted her boss. Once again, the beautiful woman was dressed down but still looked classy. The black romper had long loose pants that would cover her heels when she stood, but was cut to expose her shoulders and a hint of cleavage. On her feet were of course the cute three inch heels she tended to favor. A cruel smile twisted Chloe’s lips as she used a delicate wave to motion the pair over to her seat at the bar.

Pointing casually to the woman to show the hostess that Deedee’s party was waiting, she squeezed Trent’s hand once before releasing her grip and slipping through the crowded dining room. Trent followed along behind as trepidation once again filled him. He wasn’t sure which feeling he hated more, the eyes of all the men around him that seemed to be undressing him as he swayed through the room or the feeling of angst that seemed to be flowing off of his father. Looking past Deedee to Chloe, Trent’s lips tightened into a **** smile as he saw the cruel glint to the woman’s eyes. He could feel a pang of sympathy for his father build up inside of him, only for it to run into his own humiliation at the situation.

As the pair finally approached, Deedee once again managed to slip deeper into the role she had been inhabiting for over a year now. Her smile became broad and almost vapid as she stepped up and gave Chloe an air kiss. “Good afternoon Miss Jameson, thank you for inviting us out! I really appreciate the opportunity to show off this new outfit.” Reaching back, she hooked her arm around Trent’s and pulled him up alongside her. “I don’t think you have met Tiffany yet. Tiffany, this is Miss Jameson. She isn’t just my boss, she is more like a mentor and hero to me. She has shown me how to be the real me. Isn’t that just wonderful?”

Trent did his best to keep the shock from his face as he politely waved. Chloe’s piercing gaze locked onto his eyes and she tilted her head to the side. The cruel look never left the woman’s mouth as she nodded slightly in acknowledgement before looking back to Deedee. “You are late. Your date is waiting. Why don’t Tiffany and I get acquainted? I would love to hear more about how you two are getting along.” Trent could feel a slight stiffening in Deedee’s body as she swallowed and nodded.

“Yes of course Miss Jameson. I apologize for our lateness and I will strive for it not to occur again. I am sure that you will think of the appropriate punishment for me at work tomorrow. I am sorry for disappointing you.” The words flowed perfectly from Deedee’s lips as she turned to glance across the room to see if she could spot her date. Seated a few tables away, more than enough for the pair to see everything that would follow, a man sat at a table alone with his back to them. “Is that him Miss Jameson?”

“Yes, now go.” The curt response was given as Chloe motioned Trent to slip onto the barstool next to her.

Deedee quickly made her way over to the table, only to freeze in place once she recognized the man seated there. The pause and fear that shot through Deedee **** a sharp short laugh from Chloe as the trap had now fully closed over the feminized secretary. Turning to Tiffany, Chloe grinned at the look of confusion. “Right about now, Deedee is realizing you both know the gentleman she is going to spend the afternoon with.”

Trent turned to look at Chloe, remembering Deedee’s instructions before entering the restaurant, Trent **** his lips into a fake smile before speaking. “Thanks for like, explaining that Miss Jameson.”

Chloe’s eyes lit up with humor as she heard the ridiculous valley girl inflection from Tiffany. “Oh, now that is just precious.” A soft chuckle was interrupted by the approach of a bartender. Trent quickly ordered a soda water with lime before turning his attention back to the table.

While that had been going on, Deedee had made her way fully to the table and sat down in front of the tall dark haired man. “Good afternoon Mr. Mace.” The man sitting across from her was well built, with a short well groomed beard that was just starting to show the hints of graying.

“Hmm, is it now? I would have expected this would be your nightmare turned real… Derek.” The name hit the table like an oxygen bomb. Deedee’s controlled facade cracked sharply as she realized just how badly she had been set up by Chloe. Sitting across from her was Maxwell Mace, her ex-brother in law. Max had never been Derek’s biggest fan. From the day they had first met, the larger man had always seemed to find flaws in anything Derek did. Deedee could even find a correlation between Max moving back into town and his ex-wife’s shift in attitude early in their marriage.

Swallowing audibly, Deedee did everything she could to pull the shattered pieces of her mental state back into place. A deep breath bought her enough time to try to find a way to respond to the question. “O-of course, sir. Anytime I can sp-spend making sure that Miss Jameson’s clients are happy is a good time.” Starting shakily, the words began to flow more naturally towards the end of the ridiculous statement.

Shaking his head at the pathetic display in front of him, Max allowed his eyes to take in Deedee’s full appearance. He took his time to investigate each part of her. His lips pursed in thought as he let his gaze slip over her heaving breasts. The smirk on his lips grew as he watched the feminine mannerisms that were baked into the core of her actions. The silence stretched on as Max sat patiently and studied her.

Across the room, Trent and Chloe watched as a waiter approached the table. Unable to recognize the man that she had told him he knew, Trent allowed his eyes to gravitate towards Deedee.They were too far away to make out the words, but easily within distance to see the body language. He could see her stuttering and fumbling with her speech. Her jerky motions were nothing like the smooth and elegant movement he was used to seeing from her.

For her part Chloe seemed a bit bored as she sipped at a cup of white wine. Turning to look at the gorgeous blonde beside her, she looked over his outfit and allowed the smug satisfaction to radiate from her. “You walk well in those heels. Our little Miss Hoover seems to have trained you well. Or, did you perhaps already enjoy trips to the softer side? You seem to have taken to it rather quickly.”

The distraction of trying to figure out who the man seated at the table might be, along with worry over the looks on Deedee’s face, made it impossible for Trent to stop the answer from slipping from his lips. “Like, no, Miss Jameson. I never did this before.” Turning to look at the woman next to him, he raised an arched eyebrow. “And like, what do you mean Miss Hoover?”

“Oh, she didn’t tell you?” Chloe let out a full throated laugh. Even the woman’s humor seemed to have a sinister sound to it. “I certainly wasn’t going to let her keep that silly name of hers. Did you think Deedee was her real name?” The woman continued on without allowing him to answer the question. “That pretty little sissy sitting there has an ID and birth certificate that read Donna Jo Hoover. Deedee was just a cute little pet name I gave her that seemed to stick. I gave it to her when she chose to have those Double D implants put in. I was only going to make her get C’s.”

Trent had no idea how to respond to the litany of revelations that the woman kept revealing. Her happiness seemed to grow as he was unable to stop the looks of shock from taking over his face. “But, I’m sure she will tell you all about that later. I know all about good old Double Dee over there. You are the one I want to know about. So, let’s play a game shall we? I’m going to ask you a question. Each time your answer isn’t what I want to hear, I’m going to press this button.”

Looking down on the bar, Trent saw Chloe’s phone sitting open, a large red button sitting in the center of the screen. There were a number of sliders and selectors available. The settings appeared to be set fairly low at the moment, but Deedee’s earlier warnings and the threats that seemed to come off of this woman told Trent that they likely wouldn’t stay that way. “Now, let’s start easy. Are you wearing all your proper accessories today?”

The question was obviously a trap, there was no way for him to know if he was wearing the correct accessories. He felt like he wore the correct jewelry and such, but with only a few days of femininity to his name it was impossible to know for sure. Experience with bullies through highschool had taught him that saying ‘I don’t know’ wasn’t an option either. Much like the law, bullies never saw ignorance as innocence. No, seemed to be the worst option of all.

“Too slow. Let’s see if Deedee has hers on..” Reaching out, Chloe pressed her finger against the button and held it as she looked across the room at the other table. Trent’s eyes followed her gaze and watched as Deedee suddenly sat bolt upright in her chair.

“Oh no.” The words were breathy as they were pried from Deedee’s throat by the vibrations buried deep inside of her. Her hands gripped the edge of the table as she tried to ride out the waves of sensations that radiated through her while the waiter dropped off a pair of red wine glasses.

“You actually like that don’t you? Having that toy buried deep inside of you and vibrating away.” Max shook his head and leaned back in his chair to sip at the wine. “I knew that you weren’t good enough for my sister when I first met you, but this is a whole different level. Tell me the truth Deedee, you love who you are now don’t you? And remember, Chloe is listening in.” Turning his head to the side, he pointed up at the small black bluetooth earpiece in his ear. “We wouldn’t want to disappoint her now would we?”

Deedee winced at the words that Max so casually threw at her. Hearing her ex brother in law bring up her ex wife and all of the wounds that came with that hurt more than the humiliation of actually being turned on while knowing she would be **** to please this man later. The landslide of different thoughts and emotions combined with the waves of pleasure that had just now disappeared made answering difficult. “Of course I do. Anything to satisfy Miss Jameson, or her clients. I love making people happy.” The words were stilted and robotic sounding to them both. It was an old script, one of the first that Deedee had memorized as Chloe punished her with more and more humiliating situations.

“Not good enough.” Pulling his own phone out and setting it on the table, Max pressed down on the red button that was clearly visible in the center of the screen. Deedee tensed as she expected the vibrations to kick back up, only to look up at the bar in shock when the feminine shout of surprise came from Tiffany.

At the bar, Tiffany could feel his own plug come to life. The surprise had **** a half moan half shout from his lips as he jumped off the barstool and stood on his tall white heels. “Like, what the hell?” Trent closed his eyes as he stood there, not used to the feelings as they radiated through him. Just wearing the plug felt alien to him, but the deep wave-like vibrations that strummed through his body were making it impossible for him to control himself completely.

Chloe reached out and pushed him back onto the barstool. “Sit down, and stop making a spectacle of yourself. Unless of course you want that?”

Sitting down suddenly only made the sensation worse as Trent’s lips parted and a softer moan slipped out again before he could gain control and answer. “Like, no, Miss Jameson. I totes would rather stay quiet but like, this is like, new to me.” He paused as he panted and tried to get control only for the sensations to cut off suddenly. The sudden lack of pleasure was almost as shocking.

At the table, Deedee and Max were both staring up at the bar where the sudden sound had come from. Max chuckled as he saw the gorgeous young blonde. His eyes narrowed slowly as he spoke. “She looks familiar.” The words sent shocks of fear through Deedee instantly.

“Tell me more about how I disappointed you Mr Mace. Maybe I can find a way to succeed… now that I am clearly in a more fitting position in life.” The words leapt from Deedee’s lips as she drew the man’s attention back to her. The emphasis on the words succeed was not lost to either of them as Max shook his head and turned back to her.

Trent turned to look into Chloe’s eyes as he recognized the man at the table. “Uncle Max? You’re gonna, like, make Deedee fuck my Uncle?!”

“Well, certainly not here in public. And likely I’m going to let your Uncle fuck Deedee. I know it is slightly pedantic, but the meaning is very important. You see, Deedee hasn’t been allowed to use her little tool in a very long time. I’m sure she plays with it at home, but that is nothing like the feeling of having someone else pleasure it.” Turning to look into Trent’s eyes, Chloe smirked. “Not that I hear you get to do either.”

Trent’s cheeks flushed scarlett as his mind shot back to the blowjob of the evening before. The memories were still fuzzy and painful, but slowly they began to make more sense. The interactions with Chloe were slowly showing Trent just how badly messed up the world Deedee seemed to exist in was. Remote controlled vibrating plugs, sudden dates with strange men, humiliating circumstances designed to drive her self worth down, they all seemed like shockingly normal situations that his father now found herself in. Turning away from the table, Trent picked up his glass of soda water and sipped it slowly, using the action to buy time before he was **** to interact with Chloe yet again.

Shaking her head at the clearly lost sissy next to her, Chloe turned her attention back to the other two as she watched and listened in on her own bluetooth earpiece.

“Disappointed is a good way to put it. You ruined my sister’s life. She gave you a son. She gave you a perfect wife and family. How did you repay her? You fucking ignored her because you weren’t man enough to really be there.” The words tumbled from Max like they had been rehearsed over and over. It was clearly a litany of hatred that the man had practiced in preparation for the event. “But clearly, you think that whoring yourself out to me will somehow make this better. Somehow you sucking my cock is going to give my sister back the best years of her life that you stole from her.”

Deedee closed her eyes and let the vitriol pour over her. The last few days had brought her wife back into her memory more times than the past year had. Each memory was like a needle jabbing into her skin. They were painful, but certainly bearable. A deep breath in and then back out gave her time to galvanize her thoughts as she struggled to find a way to keep Max from realizing just who the stunning blonde really was. “Mr Mace, sir. Would you like to go somewhere more private?”

Deedee stood up and held her hand out towards the man. Her eyes pleaded with him as he stared up at her. Standing up out of the chair, Deedee was once again struck by just how large he truly was. Towering over her, even in her tall stilettos, she looked up into his eyes and saw the hate and anger there. His voice was level as he responded. “I have a hotel nearby.”