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Chapter 40
by RachelDaws
Does Miss Jameson follow with Tiffany? Or is our young sissy in for a different fate?
Deedee makes a decision
Chloe’s grin lit up as she heard the pair across the restaurant’s conversation through the bluetooth earpiece that hung next to an expensive earring in her ear. Meanwhile, across the room Deedee was using every ounce of her formidable training to keep the silly bimbo grin plastered onto her lipstick painted lips as she slipped her long nailed hand into the hand of her ex-brother in law. Max’s smile had a cruel lean to it as he began to lead his date across the room.
Trent watched as Deedee and her uncle glided through the crowded room. Just as he watched Deedee and Max slip out the door, his breath caught again within his chest as he saw a man walk through the door. It was easy to recognize his girlfriend’s brother. As quick as that recognition hit him, it was even faster that his mind drew the parallels between the men and their relationships. Trent’s long blonde tresses whipped around as he looked into Chloe’s eyes, a prayer in his mind that it was a simple coincidence. The evil glint and the delicate laughter that erupted from her left no doubt in the manufactured nature of his appearance.
Chloe leaned forward and spoke softly, her words audible only to Trent as the pair stood next to each other. “I can see you have drawn the appropriate inferences. What you don’t know is that Sammy there, has no idea who he is meeting. Let alone, any concept of a deep dark secret that might exist under his would be date’s skirt.” Pausing, the older woman slipped her cell phone from out of her purse and set it on the bar between them. Her finger brushed up against the speakerphone button. “Maxwell, darling. Can you hear me well enough?”
The phone’s tinny sound was difficult to hear in the crowded bar area, but certainly still easy enough to discern as Max’s voice came through. “It is. I assume this is that point where my night could change, isn’t it?”
“It is.” Chloe’s voice was commanding and imperious as she continued on. “Tell Deedee her choice.”
Trent’s mind spun as he tried to figure out the game that the demented woman was playing on him and Deedee. He knew that Chloe had manufactured this event to test or taunt Deedee, but it turned out that it might just be as bad, if not worse for him. As he tried to come to grips with the possibilities of the situation, Max began to speak to Deedee. “I’ve been told by Chloe that I am to give you a choice. In either case, we go back to my hotel room. In the first case, you and I will create a nice recording for us to send to my sister. Of course, you will have to introduce yourself. You will tell her how much you enjoy the encounter, your performance will be perfect. Any failure to do so will result in demerits, for both you and Tiffany.”
Deedee stood on the sidewalk and listened to the man in front of her as he maliciously presented the situation. Her body was rigid, almost shaking as she tried to think of a way out of the cruel and humiliating situation. The fear that came from revealing herself to her ex-wife, as well as spending the evening pleasing the man she believed to have caused the end of her marriage, made her almost miss the second option he was presenting to her. “Or, you and I go back to my hotel room and we spend the evening getting to know each other. Off camera of course. If you choose this, then Tiffany is going to get to experience an evening exactly like yours. Her little girlfriend’s brother just walked through the doors to the restaurant.”
Deedee’s eyes widened even further in shock. She knew Chloe’s cruelty was immense, but this seemed overboard even for her. Inside the restaurant, Trent’s eyes closed as he realized just how trapped Deedee truly was. His mind went back to last night, he could see the cruel look on Deedee’s face. It was a perfect mirror to the look he saw on Chloe’s face now. How could he expect Deedee to debase herself like that for him? She had put him into this situation. It was her decisions that had led the pair to this pivotal moment. Deep within himself, he couldn’t find a single reason why Deedee wouldn’t take the second choice. His eyes closed as certainty fell across him like a weighted blanket. A single tear formed at the edge of his perfectly made up eye as he resigned himself to his own humiliating night.
Being stuck in his own mind had made Trent miss the next words that came from the phone. So it took his mind a moment to catch up to the inputs it was receiving. “Of course you can video me Maxwell! What kind of kinky, silly, bimbo slut wouldn’t want such a big strong man like you to show off our session to whoever you wanted to later? I’d be honored. Do you hear me Mistress? Please.” The words started playful, even if they had a bit of a robotic sound to them as Deedee **** them out. Quickly they devolved into a pleading, begging tone as Deedee tried to address Chloe through the phone connection. The last word was filled with anguish and fear, none of it having anything to do with her own situation.
Chloe’s eyes widened for a brief second in surprise before she managed to control her emotions. The smile on her face receded slightly before she spoke. “Fine. Make your video Maxwell.” Reaching into her purse, she quickly dropped a pair of twenty-dollar bills on the bar and pressed the end call button. “Come with me Tiffany.” Turning, she marched towards the entrance to the restaurant. Trent followed quickly trying to catch up to the retreating woman. His quick short steps that the tall heels **** on him made his breasts bounce up and down exaggeratedly as the lacy bralette failed to contain the massive globes that had been adhered to his chest just days ago.
Outside, Maxwell simply turned and began his own walk towards the tall hotel across the street. Deedee walked quietly, her own steps shooting out a staccato sound as she did her best to keep up with his long strides in her own tall heels and tight dress. The pair were silent as they made their want into the lobby and onto the elevator. It was only when Max pressed the button for the 15th floor that he spoke up again. “So, who is Tiffany? And why are you willing to let me finally show Becca who you really are just to protect her?”
Anger and protective instincts flashed in Deedee’s eyes as she realized that Chloe hadn’t revealed everything to Max. Biting her lip, she leaned in and pressed her perfectly formed body up against his before speaking up. “Oh darling, do we really have to talk about another woman? You have me all to yourself, and all you can think about is some other girl you know nothing about? Don’t you want to spend your time thinking up more fun ways you can show me off to the camera? More way you can make me prove just how much I want this?” Her hand slid down to the front of his pants and wrapped around the growing hardon that was there. The act was coming back to her as she managed to allow her training to come back into control of her actions. She could feel her own arousal rising as she felt the large cock through the thin layer of his slacks. Licking her lips, she looked into his eyes and waited for him to respond.
“Wait till we are in the room, slut.” The last word from Max’s lips was meant to cut into Deedee. Max had filled it with all the vehemence he had stored up towards her over the long years. Only it had the opposite effect. Deedee giggled at the slur as she gave the cock one last squeeze before releasing it, but not stepping away from him.
“Yes sir.” Her voice had a breathy air to it as she fully let the subservient and whorish personality that Chloe had cultivated early in their relationship take over. “Sorry Daddy, I just get so thirsty for it.” She knew her actions would distract the man from asking more questions about Tiffany. Inside, she prayed that Chloe would keep up her end of the bargain.
As the pair rode up in the elevator, Chloe and Trent were both strutting across the street themselves. Their own walk had been silent as well. Trent stayed quiet through fear that Chloe would still reveal him to Sam, while Chloe was slowly coming to terms with the decision Deedee had made. It wasn’t often that Deedee surprised her anymore, but this last decision had been perhaps one of the most unexpected she had encountered. When they had spoken just days ago, she had heard the hurt and anger in Deedee’s voice when the woman spoke about her son and their interactions. Chloe was unable to conceptualize the situations that could have occurred where Deedee would sacrifice herself instead of letting Tiffany suffer a simple bit of humiliation that would bring the buddy girl into line.
Chloe and Trent stepped off the elevator onto the 15th floor and moved down the hallway quickly. The soft carpet muffled the sounds of their steps as they moved through the dimly lit corridor. Pulling a keycard from her purse, Chloe unlocked a door and motioned Tiffany in through it. Trent moved cautiously into the room, afraid of what he would see. Relief flooded his body as he took in the empty hotel suite.
Chloe kicked off her heels as the door closed behind her. “No idea how you two can wear those stilts for so long. Must be because you aren't real women.” The pointless barb fell short of bothering Trent, except to remind him exactly of how he was dressed. He stood in the center of the room, unsure of how to proceed or even respond to the cruel woman. “Why don’t we see what is on TV? Deedee and your uncle Max are going to be busy for a while.”
Settling onto the couch, Chloe pointed for Tiffany to join her as she curled up with her legs on the sofa and got comfortable. Picking up the remote, she pressed the power button. The television flared to life as Trent made his way to the couch and carefully sat down. The soft cushion was only slightly better about reminding him of the plug still lodged inside of him than the hard stool had been, but at least he was able to lean to the side as he crossed his legs at the knee and leaned against the arm rest. Sitting as far away from Chloe as he could, he turned to look at the TV. The scene that greeted him tore a gasp from his throat.
Chloe smiled as she turned up the volume in time for Deedee’s voice to come through bright and clear. The slutty bimbo personality was bleeding through to her voice as she emulated a porn actress, unaware that Trent was watching it all occur. “So, where do you want me, Mister Director Daddy?”
Deedee's long and hard day
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Sins of the Father
From father and son to couple.
Trent comes home to find his father Derek is now Deedee, his crossdressing sissy father. After a fight, Deedee decides to show Trent that maybe he isn't as manly as he thought he was.
Updated on Oct 4, 2024
by RachelDaws
Created on Apr 13, 2024
by RachelDaws
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