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Chapter 30
by RachelDaws
Well now, who saw that coming?
Rachel and Deedee did of course.
Deedee’s eyes were glued to the departing forms of Jessica and Tiffany. Rachel’s voice brought her back to the table as the blonde woman spoke up. “Deedee, hun, I know you are worried. You need to trust Jessica. She really does care for Tiffany, she even cared about the person she used to be. Honestly, I think she would have tried to make a man out of him if I hadn’t expressly forbidden it years ago.”
A lengthy sip of wine gave Deedee enough time to calm her nerves. Her mind turned over what Rachel had said and caught on a particular phrase. “Forbidden it? Why?”
Rachel’s hand reached out across the table to rest on top of Deedee’s, a reassuring squeeze followed before she explained her statement. “Well, I wasn’t particularly sure how he would take it. Based on my understanding of what happened the other morning, I’m glad we waited.”
Deedee nodded, her mind casting back to the argument that started this roller coaster of events. She thought back to Trent’s crushes on Jessica, all the times he had cried silently when she would find some way to kindly rebuke his advances. Each time she tried to picture him finding out about the hidden gem in Jessica’s panties. After running through a number of possible events, Deedee knew Rachel had been right. “So why now? I think I understand but I would like to hear your reasons.”
Rachel chuckled and picked through the food on the table delicately. Ending up with an olive, she popped it into her mouth and chewed before responding. “Multiple reasons. One, he can’t scream about it, because then he gets found out too. Two, with both of them in heels and dresses? I bet on Jessica to win that every day. Three? Well that is actually the fun one. From what Jessica tells me, you caged him two days ago. That cute little thing almost turned into a puddle just from Jessica toying with his cage for five minutes. I don’t know that an actual snake under her skirt would stop him from playing with her. Another olive followed the first as the beautiful woman waited to see what the response would be.
Deedee’s upcoming response would not quite be what Rachel would expect. She expected Deedee to argue, or best case scenario to agree. Instead, what she saw caught her completely off guard. Slumping back into the booth Deedee’s face took on the look of a woman crushed under her own insecurity. Mumbling something under her breath, she pulled her hand free of Rachel’s grasp and hugged her arms around herself as she visibly wilted inwards.
Rachel’s head tilted to the side quizzically as she took in the instant change in Deedee. Concern etched her face as she spoke up. “Tell me what is going on Deedee. What just happened? Jessica told me you have been doing really well with this, but it is clear something is not ok.”
Deedee swallowed heavily before forcing her eyes open. Looking up through her lashes into Rachel’s stormy gray eyes, she responded quietly as her gaze fell to the floor. “I can’t do this.” Forcing her arms to unwrap themselves from around her, she took another breath before looking back up. Rachel could make out the glistening in the raven haired woman’s eyes that threatened to turn into tears.
“I see. Unfortunately, you have a tiger by the tail. If you let go now, it will spin around and bite you.” Pausing, she let those words sink in before speaking up again in a much more friendly tone. “But, we can fix this. I have known you through Jessica for a long time Deedee. And while neither of us were fond of Derek, both of us love Deedee. Trust me when I tell you that you can do this. You just need to find your way of doing it.”
The defeated look on Deedee’s face lessened as the praise for who she had become blew some air back into her sails. Still not convinced that she could turn this situation around, Deedee allowed self doubt and guilt to continue to **** her from within. “I tried.” Her gaze shot up to stare into Rachel’s eyes. “I couldn’t even do what Chloe told me to. I had the playbook and I fumbled the bag. All I had to do was stay strong and I couldn’t do it.” Anger at herself boiled up and crept into her words.
Smiling at the signs of fire in the woman across from her, Rachel shrugged. “Of course you couldn’t. For all that I have heard that Miss Jameson is a fine dom, she certainly isn’t you. From what I understand, this wasn’t like a situation like I had with Jessica. With Jessica, I saw something in her that told me this is what she wanted. Chloe, instead took advantage of your weakness and **** you into this. I refuse to get into a discussion if either is better. Simply put, I think you need to approach this from a different way. So, let’s focus on how your situation is entirely different.”
The anger in Deedee faded slowly as she listened to Rachel’s logic. The even tone that she heard brought a sense of stability to her. The husky voice seemed to lock her attention and lull her into a state of listening. “I don’t understand. How is it different?”
Seeing that Deedee had come down from the spike of anger and was in a place where she would listen, Rachel continued. “Quite simply, neither Chloe nor I cared about our charges in the way that you do.” Deedee’s expression showed the confusion on how that would matter as she waited for Rachel to expand on that particular thought. “It was very easy for me to do things to Jessica that she hated at the time. It didn’t matter to me if it was something to make her a better version of herself, or if it was something that got me off. I was doing the entire thing for my benefit, and because I truly believed she wanted it. Which, it turns out, was correct. Chloe cares even less about you. Tiffany and your relationship is infinitely more complicated. Seeing your child tear up and beg you to stop doing something must feel like you are tearing yourself apart. Seeing the real hurt in his eyes at his perceived betrayal by you? I cannot imagine how difficult that must be.”
Deedee gasped as Rachel put into words the feelings that she had been trying to pin down. The guilt had been building up inside of her as her actions slowly drove Trent farther and farther down the path she had laid out. Hearing her feelings affirmed lifted a weight off her shoulders that she hadn’t realized was there. In her mind it should have been simple to do what she knew was successful and had been accomplished previously. Truthfully, while Miss Jameson had set the path in motion, it was Jessica and Rachel’s relationship that she truly wanted to emulate. Draining the remainder of her wine, Deedee reached out and stole Tiffany’s glass. “So what do I do? I love him, and truthfully, I think I love her as well. Which is really confusing.”
“Well, first, you need to stop thinking of them as different people. If you accomplish your goal, it will not be a combination of Tiffany and Trent, it will just be Tiffany.” Deedee nodded. She knew that she needed to stop thinking of Trent as her son, she just kept failing at it. Rachel laughed at the absurdity of her own statement. “This is simple, but not easy. It will come in time, especially once your relationship passes into a more sexual nature.”
Even the idea of a sexual relationship with Tiffany was enough to cause Deedee concern at hiding herself in the tight dress she wore. “God I can’t wait.”
“Nor should you.” Rachel smiled. “This is the part I think that will help you the most. You need to move Tiffany’s perception of your relationship into a different realm. Right now she sees you as her father and her as your son. The visuals don’t matter. But if you can make her start to feel pleasure? If you can take her out of that zone? That is where the greatest changes will start to occur.”
Deedee’s thoughts cycled through the responses Tiffany had shown to each of the different experiences they had gone through. In both situations she had been the one to break. Yes, Tiffany had said or done things that hadn’t been comfortable, but she knew that was going to happen. If she was going to get through this, she needed to stick to her guns more.
“I can see the gears winding through your mind, looks like you already know how to make that work out?” At Deedee’s nod, Rachel continued. “She needs more than one reason to keep doing this. If you make it all about sex, she will just get post orgasm clarity and you’ll lose whatever inroads you will have made. Ideally, it would be your approval. I’m not sure that will work in this case. I don’t know either of you well enough to tell you what it should be, but I think you can figure it out. Plus, if you ever need a chat like this, I’m here for you honey.”
Deedee didn’t care about the state of anything as she slipped out of the booth and stepped over next to Rachel. Wrapping the blonde in a tight embrace, Deedee fought back tears as she felt support for the first time in over a year. Her whispered words barely registered in Rachel’s ears. “Thank you.”
The conversation between the pair veered into safe and less strenuous territories after that as they waited for the other two to get back from the restroom.
Will they return soon?
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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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