Chapter 11
by RachelDaws
Time for lunch and answers
Tiffany plays with sausage and Deedee enjoys her meat
(Author's note -I don't know if this is the best way to keep getting feedback for you all, but I tseems to be working so far! :P In this story I play with pronouns a lot. My goal is always to try and show the pronoun of what the character interacting with that person is viewing it as. I know, it is probably gauche of me to give you all the formula, but I wanted to see if this particular thing was landing. It is a difficult situation as I have two characters that tend to fluctuate how they see themselves and how others see them. I want to make sure that I am honoring that. Anyways. love ya'll and all the feed back. Keep it up! Rachel)
It was a simple matter for Deedee to lead the stunned woman on her arm into the restaurant. “A booth please, for two?” Was all Deedee needed to say before the pair were led deeper into the establishment. Stepping up to the table, Deedee helped Tiffany slide into the booth, although the new woman had some difficulties with her skirt as sitting in such a short one was very new to her. Slipping down alongside her, Deedee smiled up at the hostess and accepted the menus. As the woman walked off, she set them down and looked over at the feminized man next to her. A soft smile spread across her face as she looked over just how pretty Tiffany actually was. What had been boyish and weak on Trent was cute and gorgeous on Tiffany. Without even thinking about it, Deedee reached up and pushed a strand of hair back behind Tiffany’s ear with her long nails. “You really are beautiful.”
Swallowing deeply, Trent sat there feeling like a deer in headlights. His mind spun as he realized that he had been stunned like that most of the day so far. It seemed like every time he managed to find some kind of footing that something would derail him. Either it was Deedee or even the world itself, it seemed like everything was conspiring against him. Even that thought had more questions in it. When had he started to think of Deedee as her? Wasn’t this his father? And yet sitting there next to her, smelling the heady scent of their perfumes mingling together, looking at her beautifully made up face as it sat over those large and prominent breasts, it was difficult to think of her as anything else. Still, he had to fight back somehow. Ducking his head away from her gentle touch, he tried to scoot deeper into the booth. His mumbled reply angled down into the table so much that Deedee had trouble hearing it. “I don’t want to be beautiful.”
The sigh that came from Deedee was equal parts exasperation and understanding. “I am sorry to say dear, that what you want is not important at this time. In the future, I promise that I will provide everything you will dream of, but right now I need to teach you some lessons.” Reaching down to pick up both menus, Deedee slid them over to the edge of the table to inform the server they were ready at any time. “I need you to accept that for right now this is your reality. Life is not always fair or easy, dear. I have done my damnedest to make your life easy and fair up till now. All that got me was a set of tits and a tirade of hate speech from the person I love the most in this life.”
Shrinking back from the words that came from the woman next to him, Trent’s stare bored into the table top. “So now what? Am I just some barbie doll for you to play with? Are you gonna turn me over to the bitch who did this to you? How the fuck am I supposed to live my life like this?” The questions tumbled out as frustration started to rise up in him again. Anger began to flare as he clenched his fists at his side, the nails once again stopping him from forming any kind of actual fist.
Deedee’s reaction surprised both parties as she reached out and not so gently took Tiffany’s chin in her hand, pulling their gazes together. The fierce and angry look on Deedee’s face informed Trent that he had misstepped somewhere and upset his father. “You will not speak of her that way Tiffany. I will stand here and let you say what you want about me. But you will never say those kinds of things again about her. Am, I, Understood?” The pause between each word was punctuated with a moment of added pressure in the grip that held Trent’s face. Seeing that the person in front of her wasn’t responding, Deedee released her former son’s face and closed her eyes in an attempt to get her emotions under control. “First lesson. When I ask you a question or give you an order, you will respond.”
Deedee’s tone held that icy anger that Trent was beginning to fear. Each time he had heard that tone come from his father’s made up lips, his life had somehow gotten worse. Reaching his hand up to rub along his jaw where her grip had been moments ago, Trent tried to think of a way to navigate the minefield he had somehow found his way into. “Look, I’m sorry. I won’t talk that way about…her. I just don’t understand this. I… I just…I…” Trent’s heavily made up eyes squeezed shut as the frustration of trying to express himself without digging an even deeper hole made the questions jumble up in his mind.
“You might be surprised at this Tiffany baby, but I understand what you are going through.” Reaching down to rest her hand on Tiffany’s stocking covered knee, Deedee smiled softly and continued. “Right now you are fighting with everything you have to find a way to get out of this. Your mind is rebelling at all the sights, sounds, and feelings that are assaulting your every sense. The fear is making your heart beat faster and faster. The shoes hurt, the corset hurts, the air on your legs between your dress feels alien. I have been through all of this.”
“So why are you making me go through it?!” The same question kept coming up, and while Deedee had answered before, that answer wasn’t sticking to Trent’s mind. It was like some part of him knew that there was no way he deserved or wanted this.
Deedee’s long nails lightly played along the soft stocking on Tiffany’s thigh. The sitting habits of a young man had Tiffany’s thighs open and allowed for her fingers to slip along under the skirt and towards the small pink cage. Trent’s sharp intake of breath showed Deedee everything she needed to know. “Because of the rest of the feelings you are feeling right now. The ones you don’t want to admit to.” Leaning closer to whisper into Tiffany’s ear, Deedee slowly continued to tease her son’s inner thighs with her nails. “You don’t want to admit that you felt special the first time you saw yourself. That for the first time in your life you didn’t look insignificant. I know how scared you were when Steve was looking at you like a rack of lamb, but that fear was just a thin covering for the real feelings you had.” Deedee’s fingers traced up along the lace of the stockings and slipped up to tease the bare flesh.
“What…what are you d-doing?” Stammering and stuttering, Trent sat there as the **** on his senses continued. Only now it wasn’t just the feelings of the outfit, his pinched toes, crushed waist, or the new and heavy weight on his chest. Now it was the cognitive dissonance that the gorgeous woman who had her hands creeping closer to his cock also happened to be his father. The man who had provided for him and protected him his entire life. The spark of lust that ignited into a glowing ember in the pit of his stomach felt wrong, and yet something about it also felt right.
“I’m showing you that there aren't just bad parts to this baby-girl. There are a lot of pleasures to be had.” Deedee’s fingers finally reached their way to the lace panties that covered Tiffany’s cage. Her nails flicked against the hard plastic that was now restraining Tiffany’s clit from growing to its full size, not that that was much larger than it was now.
It was at this time that the waitress chose to appear. With Deedee’s hand shoved up Tiffany’s skirt and Tiffany sitting there chewing on her bottom lip with half lidded eyes as he tried not to let the feelings of lust overtake him. “Hi! Welcome in! My name is Krysta, I’ll be your server today. Can I get you some drinks, or are we ready for some appetizers?”
“No need hun, we are ready to order. For myself, I will take a filet, medium rare with a side salad with vinegar and oil on the side, and veggies for the side to main please. And my cute little girlfriend here will have just a side salad, no dressing.”
“Of course, what about drinks? Soda, iced tea?” Krysta’s gaze was easy for both of the people in the booth to read as it locked onto what looked like a sexily dressed milf who had her hand up her much younger date’s skirt. Her professionalism and desire for a good tip kept her customer service look in place, even if it was clear that the sight made her more than a little uncomfortable.
“Could you bring us two white wines please? House white is fine. Thank you hun, that will be all.” As the waiter walked away, Deedee was surprised at herself. She had ordered the wait staff around so easily. It seemed that playing with her new toy like this was causing a number of old feelings to surface. Feelings she had buried for the last year. It felt good to be in charge again, and even better to be doing it as who she was now. The widening of the waiter’s eyes as she saw this gorgeous pair of women enjoying each other, the look of surprise as Deedee had ordered for them both, each had been intoxicating to Deedee. That feeling of control that she had been missing in her life. Looking back to the woman who writhed slightly under her ministrations, she continued. “Now, where were we hun?”
Trent did his best to sit there perfectly still. His eyes were once again locked onto the table after having looked up and realized that Krysta had obviously seen his father’s hand shoved up under the skirt he had on. Embarrassment, and something else, caused a flush to slide up his chest and onto his cheeks. Of course even looking down like that wasn’t any safe haven from the oddness of his predicament. Jutting up into his view were a pair of reminders that he was in a different world than the one he had gone to sleep in. The large breasts on his chest looked perfectly real, until he realized that the flush he knew was covering most of his body did not extend to them. Sighing in relief, a fear that he had not even realized he had had managed to disappear. The breasts on his chest weren’t actually his. Sure, he could feel them as he moved around, but they weren’t flesh and blood like his fathers. “Stop touching me like that.” Even to his own ears, the demand seemed weak.
“No.” The simple answer had more finality to it than any of the previous interactions between the two. Slipping her fingers into the leg of the tight panties around Tiffany’s crotch, Deedee slipped the pad of her finger over the slit in the cage. With the feelings she had been providing for the sissy next to her, she knew his engorged clit would be pushing up against the cage and trying to bulge through any part it could. Her soft finger stroked along that flesh softly as she spoke again. “You don’t make the rules Tiffany, you follow my rules now. If I want to play with your little caged clitty, I will.”
Trent fought to keep the feelings of lust and need from overriding his senses. Letting as deep a breath as he could take in the restrictions of his corset out, he asked another question. “Clitty?” The term was new to him. Of course he knew what a clit was, but a man like him didn’t have one.
“Yes baby, see this little thing I’m playing with. That isn’t a cock. Cocks get big, hard, they stand up proud. This? This is a clitty. I mean, you should have seen how amazed the girls at the salon were at how small it was. Ashley says she thinks your nails might be longer than it is now.” Giggling, Deedee reached over and guided Tiffany’s nearest hand to her own groin. Trent gasped as his soft long nailed hand came into contact with a monolith of hard flesh jutting up from his father’s leather skirt. “See, that is a cock.” Trent gasped loudly at the size of the dick that he had been **** to grasp. The size difference between the penises being played with at that moment was mind boggling to Trent. How had he gotten such a short end of the genetic lottery?
“Oh my god.” Trent couldn’t stop the words from slipping out of his mouth. The buzz that occupied Trent’s mind cleared with astonishing speed as the waiter walked up and deposited the two glasses of white wine on the table. With just a few comments about their food coming right up, she disappeared as quickly as she had appeared. Disentangling himself from his father’s dick, he slipped his hands up above the table to pick up the glass of wine. While his first instinct was to down the glass, the thought that this was how he ended up in this situation in the first place slowed his actions. Taking a gentle sip from the wine glass, he set it back on the table. Staring down at it, he noticed the perfect pink imprint his lipstick left along the rim.
“All done hun? I guess we can save more of that for home. Especially now that we are dating.” Giggling to herself, Deedee slipped her hand out from under the skirt it had been invading and took a drink of her own wine glass. Setting her glass down near to Tiffany’s she grinned at the matching, yet different lipstick imprints.
“That is another question.” Trent began as he finally found a space to try and figure more of this situation out. His masculine voice continued to be incongruous with the appearance he was putting forth.
Deedee cut him off swiftly. “Now, Tiffany babe, we talked about this. Unless you want everyone to know about you, you need to start speaking correctly. How about this? I will answer any questions you have from now until our food arrives, but only if you talk the way you did in the salon.”
“Are you fucking kidding me? We are alone. I’m not doing that shit.” Deedee’s face hardened a bit as Trent threw yet another small tantrum.
“Tiffany, baby, I understand why you think that is acceptable. I will tell you right now that it is not. You need to embody being Tiffany. It does not matter if we are alone or in a group of people. You will do as you are told. Perhaps a bit of a demonstration is in order.” Pulling her phone from the black purse at her side, Deedee set it on the table. Sitting flat on the table, Trent was able to see as she began to navigate through the screens. It took almost no time at all for Deedee to pull up a contact in her phone that she knew would teach her son a lesson.
“Like, like please no…” Trent instantly swapped into the valley girl accent that he had been instructed to adopt earlier. His long lashes had snapped open upon seeing the image of his girlfriend Brittany and her phone number appearing on the screen. “I’ll, like, do anything. Just please not her, please.”
Already enjoying this sort of power, Deedee could feel the swell of lust that the begging of her son gave her. “Anything is a lot Tiffany my girl. I’m going to hold you to that. Now, let’s get back to those questions, huh?” Saved by the bell, this is the moment that the server appeared to deliver the plates of food. Setting the plain small side salad in front of Tiffany, and the rest of the food in front of Deedee, the server made a few inane comments before disappearing. Reaching for her silverware, Deedee dug into her own salad.
It was bad enough that he was sitting there in a dress and heels. Even worse was that his father seemed to be sexually assaulting him, and he seemed to be enjoying it. Yet, the true feeling of indignation came from the difference in meals laid out before him. The small salad in front of him looked sad and boring, while the steak that sat there in front of Deedee smelled amazing. “Why…” Trent suddenly remembered the threat that he existed under and swapped back to his valley girl voice. “Like, why didn’t I get a steak?”
“Well dear, we noticed earlier when we were putting on your corset that you aren’t quite as skinny as you could be. So you are going on a diet hun.” Smiling to her son, she speared a small cherry tomato as it sat on her plate. Dipping it in a small gathering of the vinegar and oil, she brought it up towards Tiffany’s pink lips. “Here baby, these are your favorite.” The fruit brushed up against Trent's lips for only a moment before slipping between them. Trent’s teeth pulled the round object off the fork and slowly began to chew. Deedee’s smile broadened as she went back to eating her own salad. “See, if you are good, you get rewards.”
Chewing through the fruit, Trent reached down and attempted to pick up his own fork. The long nails on his hand made gathering up the silverware difficult. It only took a moment before Deedee took pity on her and reached down to scoop up the utensil. Holding it made it so that Trent’s fingers could easily warp around the utensil. “Thanks.” His mumbled reply was soft, it was clear that he felt off for thanking Deedee for anything at that point. Spearing a few leaves of lettuce of his own, he started to take a large bite.
“Second lesson. We do not take big bites like that. You can’t risk getting food all over yourself.” As if to show Tiffany what she meant, Deedee’s own fork held only a small single leaf of lettuce. Trent grimaced for a moment before letting the frustration in him out with a small breath. Sucking air in up through his nose, Trent lowered the fork and scraped most of the food off of the utensil back onto the plate.
Spearing a similar sized bite to what Deedee was eating, Trent replied in the way that any sullen teen has mastered. “Whatever.” Taking the tiny bite, he chewed as he thought over everything he had experienced. The next few moments were silent as both of them sat there eating. Deedee’s eyes kept traveling up to Tiffany’s face to see if he wanted to say anything. After a bit, Trent finally managed to calm himself down enough and think through the questions he needed answering. “Like, ok, um, two things. Why do you keep, like, calling me your girlfriend? Why not your daughter?” It was frustrating enough that he wasn’t being referred to as Deedee’s son, but this whole fake relationship was just confusing. “And two, like, how long are you gonna make me do this?”
“Both good questions. I’m glad to see that you are finally thinking with more than just your ego.” Done with her salad, Deedee had progressed onto the steak in front of her. The aroma of the beef permeated the small space as she cut into it. “To answer your first question, it is simple. The things we will be doing with each other are not things that a mother and her daughter do together. While it might be cute to do some roleplay sometimes, while out in public, I want you to treat me like you would any partner. I’ve seen how you are with girlfriends, they lead you around by your balls. Just keep being that little beta girlfriend to me.” Grinning and taking a bite of her steak, Deedee chewed it carefully then continued. “As for your second question, well that is going to be up to you. You asked for this, remember? You begged me for this last night. It is so like an ungrateful child to beg for something.Then when they finally get it, they are upset that it wasn’t exactly what they thought it would be, so they throw it away. This is just like when you wanted to learn MMA, so I enrolled you in those classes.” Rolling her eyes she held up a single finger. “One class. All that gear, all those prepaid lessons. You refused to do anything with it. All it took was some man throwing you around for you to quit.”
Trent winced as his father brought up a memory that haunted him to this day. With his size Trent had never really been able to do any sports at school. Thinking that weight classes were an answer, and hoping he could avoid any of the kids at school, on his 18th birthday he had asked his dad for lessons. His father sent enough money to cover everything he would need, shin guards, helmets, gloves, special shorts, even a tight shirt to keep the rest of the guys from seeing his chubby chest, all of it. Trying to emulate his favorite fighter, he had selected incredibly tight fitting trunks. There had only been one piece of gear he had forgotten, a cup.
It didn’t take long for that mistake to become evident. Moving through all the cardio had been fairly easy for him. His legs were always the strongest part of his body and most of it was jogging and running around the room. Finally it came time for him to learn to roll. For the next ten minutes he learned the moves and slowly began to practice them against the instructor. The person teaching this class was a large man who was training as a heavyweight for a semi-professional fight. So it was with ease that he maneuvered Trent around. Slowly, the closeness with another human, the feel of a pair of bodies rubbing up against one another, it all started to get to Trent. After a particularly close move as his coach showed him how to lock in a rear naked ****, it became apparent to everyone around him that he was excited. The tight shorts and close proximity with his coach made it so that even his tiny dicklet stood out and was visible to everyone in the class. Of course Trent had never returned. Thankfully for Trent it was just after that that he managed to meet Brittany and start up a relationship with her. Spending time with his amazingly gorgeous girlfriend allowed him to do his best to forget that experience.
His lips opened and closed repeatedly as he felt the flush of embarrassment of that whole event again while he tried to think of what to say. Seeing that Tiffany would be unable to respond, Deedee went on. “So, you are going to do this till you learn your lesson. You think it is easy for me to do this? You think that I wanted this? So, to teach you your lesson, you will keep doing this until you can spend twenty-four hours straight being the perfect woman. I will be the judge of it. Any mistakes made will render that 24 hour period null. So each day if you make a mistake it gets wiped out. Midnight to midnight, if you can do that even once, I will call this off. Until then, you will be Tiffany.”
Really, two chapters for one lunch?
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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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