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Chapter 9 by RachelDaws RachelDaws

What does Trent wake up to?

It isn't Wednesday, but apparently he was still going to wear pink

(Author's note here! I am loving seeing everyone favorite and like this story. I'd love any kind of feedback or messages from all of you that are reading this. Especially if it is a mistake or something of that nature. Comments are fantastic as well and I try to reply to every one. XOXO - Rachel)


“Tiffany hunny, wake up baby-girl. You are all done.” Deedee’s voice came from lips that were close enough to Trent’s ears that he could feel the warmth of her breath. Trent’s eyes fluttered open. The fluttering was more pronounced as the long fake lashes that were now attached to his eyelids weighed them down. While that was the first thing noticed, there were so many odd feelings coming from his body that his mind couldn’t register more than one or two at a time.

As humans so much of our senses are dominated by our sight, so when Trent’s eyes fluttered open again he looked ahead and could see Ashley and Sara standing there in front of him. Ashley’s cool eyes studied him with an almost condescending look as she perched on her platform boots, one hip cocked out to the side. Sara’s look was more caring, but much less caring that he remembered it being. The next thing that occurred to him was that his hands were bound to the arms of the beauty chair that he sat in. Of course that meant he looked down at his hands.

This caused his mind to spin as he realized that the bondage on his arms was the least of his concerns. Looking down at his left hand he realized that each digit of his hand had been extended almost a full inch. The almond shaped nails had a classic white tip and pink polish on all but his ring finger. That nail was fully pink, but with a prominent glitter in it that caught the light and made it easy to notice. Looking at his right hand, it was exactly the same. The long nails elongated his fingers and gave them a dainty appearance. Following the hand up to his arm, he saw the black leather cuff that held his arms immobile.

“I see that you are taking it all in Tiffany.” Sara walked up, her bubbly attitude diminished from before. “I have to say, I was surprised that you changed your mind about the procedures. I have to say, you came out much better than any of us expected.”

As Trent’s lips parted for the first time since waking up, he felt this sticky feeling to them. His tongue inadvertently flicked out to slide over them. The taste that assaulted his senses was an overpowering strawberry flavor. Although, something about the way his lips felt as his tongue slid across them was off as well. Finally able to find his voice, he spoke up for the first time. “What the fuck did you do to me?”

“Only what you asked for, Tiffy hunny.” Deedee’s voice was farther away now, but still coming from right behind him. “After your massage, you and Sara came out and told us that you wanted to do this. You doubled down on what you said last night. I knew it was likely you would have this kind of reaction, but I also knew that I would be a terrible girlfriend if I hadn’t acquiesce to your request.” As Trent recognized that each person speaking to him had used a feminine name, he continued to look over his body. His eyes tracked back across his body as he tried to take in all the changes, suddenly two very large ones stood out. The double d breasts that showed through the cleavage of his pink dress suddenly filled his eyes.

“Oh fuck.” The words whispered from his lips as the newly feminized man realized that this had gone far beyond anything he could have feared originally. “You turned me into you.” As the words left his lips, Deedee turned the chair around slowly, finally letting Trent see his new appearance fully for the first time. Suddenly, a number of other feelings that he had not understood started to make sense.

Looking in the mirror, he could see his entire body from feet to head. Freezing in place as his foggy mind tried to take it all in, he slowly took inventory. On his feet were a pair of pink suede stiletto heels, the 5 inch heel **** his foot up at an arch that felt even more off than the heels he had worn into the shop. Turning his foot to the side, he noticed the telltale red bottom of the shoes. A memory of Brittany gushing over this exact pair surfaced in his mind. He had looked at buying the shoes for her, but the $675 price tag had been out of his range as a college student.

Sliding up out of the shoes, his legs were encased in a pair of nude stockings. The shimmer of the light reflecting off them was the first clue that they were not his natural skin, the other came as he fidgeted in the seat and felt the lace top of the stockings rubbing against his now completely hairless legs. The sensation threw a twinge into the pink cage that was still locked on him. He could even feel the garter straps that would keep the stockings up when he stood up. Those seemed to lead up to his waist. In the mirror he took in the pink dress that was belted around his now tiny waist. A deep breath caused his new breasts to swell even more as he realized he must be in some sort of corset or something. The pink dress that covered the lingerie he had on was a soft pale pink that matched his shoes perfectly. The dress had cap sleeves, a deep v-neck that just barely didn’t reveal the corset he had on. Lace covered the top half. A wide belt separated the top and bottom of the dress. The flowing skirt only came to a few inches above his knees, revealing much more of his body that he would have preferred.

From there, the second most surprising change was his face. The easiest part to notice was that 24” hair extensions had been sewn in. The dirty blonde of his hair had been softened to a pure blonde to match the extensions. Falling in loose waves past his shoulders, it was impossible to tell that it wasn’t hair that had grown from his head. Past that came the makeup that adorned his face. Finally understanding why blinking felt like such a chore, he noticed the long feathery false lashes that had been glued to his upper and lower eyelids. Those were surrounded by soft pink eyeshadow. Over his eyes a pair of arched eyebrows looked back. The delicate formations gave him a slightly surprised look. Against his bronzed sun kissed skin, the pink of his eyes and the darkness of the lashes stood out and brought your attention to them. Of course his lips also tried to get in on the action of drawing attention. The plumped bubble gum pink heart shaped lips looked like they belonged on a porn star actress more than on his face. Of course, none of the new look felt like it should belong on his face.

The problem with that thought is that it absolutely looked like it belonged there. While Trent had always been a bit of a pretty boy, Sara and Ashley’s ministrations had taken him from pretty boy to beautiful woman. Gone was his boyish charm, in its place sat a smoldering and sexy woman. Swallowing softly, Trent could only sit there. He wanted to rage against the injustices that had been levied against him. He wanted to scream and shout to tell these three bitches to take it all off and let him go back to normal. He could feel those feelings inside of him, even acknowledge that they were there. The emotions he wanted to portray felt trapped in his mind as he felt the cocktail of valium, hangover, and complete surprise had left him unable to express himself.

Finally tearing his eyes off of himself he looked up to lock eyes with his father in the mirror. Standing behind him, Deedee had also managed to change clothes. The cheetah print halter necked sleeveless blouse was tight enough to show off her breast implants, the nipples of which showed clearly through the thin material. Below that sat a black asymmetrical leather skirt with a diagonal zipper that went from top to bottom. Ending just at the top of Deedee’s knees, the zipper was unzipped enough to show a large portion of her inner thigh in a look that screamed MILF. Of course she was also perched on a pair of over the knee black suede platform stiletto heeled boots. Her own raven locks had been pulled back into a high ponytail, yet flared out to cascade down her upper back. The subtle makeup of the morning had been replaced with a dark smokey eye look that matched well with the dark almost black matte red lipstick.

Leaning down to her son’s ears, Deedee spoke into them again. Her breath tickled off his neck and earlobe as she spoke. “Here is the deal Tiffany,” The emphasis she placed on the name that they had all been calling him was heavy as she continued on. “you asked for this to happen. Now, perhaps not in the way that most would think of. But coming into my house like you did yesterday?” She paused and shook her head. “That will NEVER happen again. You are going to learn exactly what it is like to be a freak as you called me.” Kissing his ear gently, she switched to a much **** tone as she continued. “Plus, look around baby-girl, this whole salon is full now. If you start yelling about things, everyone is going to know what you really are. My little caged sissy girl.”

Trent’s eyes widened as he listened to the words that poured into his earring clad ear. Twisting his head caused his now longer hair and long dangling earrings to bounce around as he took in the fact that the whole salon was indeed full. There were at least 12 other stylist chairs that were filled with clients, and an equal if not greater number of stylists spread through the large salon. Fear caused Trent’s eyes to widen as he gritted his teeth. The feeling of his plump lips pressing against each other caused a grimace as the plump process had made them even more sensitive than previously.

Seeing that she had his attention, Deedee continued with her whispered verbal ****. “So here is how this is going to happen. You are going to be Tiffany until I say otherwise. Unless you want everyone to know exactly what you have on under that dress.” Grinning, she kissed his ear softly again, this time grazing it with her teeth. The feeling of her teeth scraping across his skin sent a shock of passion through his body. Not towards Deedee, but Trent had always had always loved having a girl kiss his ears like that. The surge of passion inside of him ran up against the wall that was the cage that continued to bind up his small cock. While Trent was dealing with those feelings, Deedee had pulled out her phone and was holding it up. To an outside observer it looked like two women taking a selfie after their makeovers. Instead, it was Deedee queueing up the picture she had taken the night before. In the picture a cock that dwarfed his own rested against his cheek, precum oozing out. Deedee’s thumb swiped over again and a closer image of the cockhead disappearing into his very visible face appeared. The next image to show up was a full body image of him laying there asleep in his panties, the pink of the cage more than visible in the dim light. “It would be a shame if I had to show these to everyone on your phone now wouldn’t it? I have that at home by the way. It is sitting in my safe, all nice and unlocked. It would be so easy to just blanket your contacts with this. Of course that would be more than a little illegal, but I certainly wouldn’t be the one doing it would I… Tiffany?”

Trent could feel himself quivering in fear as he realized how well and truly screwed he was. None of this made any sense to him. Yesterday he had been a normal college drop out. Today he sat there feminized with his feminized father kissing his ear and threatening to out him to everyone. Trying to breathe deeply to calm the fear that was beginning to take over his mind, he could only draw short shallow breaths. The corset that was giving him such an enhanced feminine form was keeping him from being able to draw a full breath in.Turning to look at Deedee, he asked the only question he could in that moment. “Why?” The words slipped from his lips so quietly that he wasn’t even sure Deedee could hear him, but it was clear what he wanted to know.

Reaching up, Deedee pressed a knuckle gently against the outer corner of her son’s makeup-covered eyes. She could see the tears welling up and while she was sure that the girls had used the best in waterproof makeup, she wanted to be sure that Tiffany continued to look as beautiful as possible. “You need to learn Tiffany. You need to learn that you aren’t who you think you are. That asshole that came into my house yesterday and belittled me for doing everything I could to make his life safe and prosperous? The abusive piece of shit that called me hateful names? Is that really who you think you are? You may not be Tiffany, but if you are going to pretend to be someone, it might as well be someone I am actually willing to spend time with.”

Deciding to give Trent some space, Deedee stepped away. Moving over to a pair of pink and black purses, she busied herself in making sure they were both stocked correctly. At that moment Ashley and Sara stepped up, each one going to one of the cuffs that went around his soft hairless arms. Speaking up almost loud enough for someone else to overhear her, Ashley began to give him her own speech. “Now Tiffany. I know that Deedee just showed you some pictures. They are very sexy if you ask me. What I want you to know is that she isn’t the only one that has evidence. You have been here for over four hours. We have images of you sitting quietly as we did each and every procedure. The best part? We were even able to copy your signature over to all the release forms. So if anyone ever comes poking around, it will really look like you wanted all of this.” Stepping back as she and Sara finally released him completely she smirked down. “Now Tiffany, you have a choice. Either I can call the cops and have you arrested for lack of payment, or you can beg Deedee there to pay for you.” Raising her eyebrow, she looked down on him and grinned. “Well?”

The rapid fire barrage of information, ****, and overwhelming sensations had left him reeling as Trent sat there. Looking around the room, he could feel his long wavy hair fluttering around as his head moved back and forth. His mouth opened and closed a number of times as he tried to think of anything to say. His mind raced a mile a minute in an effort to find a way out of this feminine hellscape. Each route ended in an even more humiliating experience. With no identification, he had no proof that he wasn’t who they were saying he was. With no masculine clothes to go home to, he saw no end in sight. The police felt like an even worse possibility. Imagine being found dressed like this and taken to a men’s jail. Even if they dressed him in a jumpsuit he would still be covered in makeup and long hair with nail extensions. He would be someone’s bitch within the first ten minutes of entering a cell. Every route appeared worse than the next, so he had ****.

His first attempt at standing in the much higher heels was almost disastrous. Falling back onto his naturally plump rear end, he changed tactics. Getting his feet closer to his center of gravity, he leveraged himself out of the chair. Sara stepped up to offer her arm in the way that he had seen men offer their arms in older television shows. Gritting his teeth at the feeling of needing this tiny girl to help him even stand there, he tried to take a deep breath again. Cursing the restriction that limited to such shallow breaths he closed his eyes for a moment before opening them again. “Dad…I mean Deedee, I would really appreciate it if you would pay for my salon trip.” The masculine tone that came out of his mouth felt off when he spoke. The sound of a man coming out of this vision of femininity was just wrong. Seeing the nearer customers look at him with a raised eyebrow, or leaning to gossip with the woman next to them, Trent froze. Even this would reveal his situation. Looking down at Sara with fear in his eyes he froze as he silently begged her for help.

“Speak softer hun. If it helps, try an accent. Maybe like a southern accent or a Valley girl?” The smaller girl was being very helpful, even if he could see the entertainment in her bright eyes. “You have that valley girl slash Barbie look. And with a name like Tiffany, wouldn’t you expect a girl that looked like you to be a bit of a Valley girl?” The grin on her face told him that she was enjoying immensely.

Seeing no out other than to take her advice, Trent spoke up again. “Like Deedee, do you think I could like, get you to pay for this?” The softer valley girl accent cleverly hid his harsher tone. The **** inflection of the words and the differing speech patterns effectively drew attention from the fact that his voice was deeper than it should have been.

Deedee perked up and stepped over. “Of course baby-girl. What kind of girlfriend would I be if I didn’t treat my favorite little wifey to a salon trip every two weeks?” The grin when she said every two weeks flooded Trent with another wave of fear. His mind raced as he prayed that she was just messing with him. Walking back up to Trent, Deedee stepped up close enough that her breasts just barely grazed against the protrusions from his chest. With both of them wearing tall stiletto heels, it was more the difference in height that gave Deedee the ability to look down into Trent’s eyes. “Let me go pay for this, then I can take you out for a late lunch hun. Why don’t you try walking around here a little bit and get used to those new shoes.” Stepping away, she turned back to look at him. “Remember, short steps, heel then toe, walk a straight line. Thankfully your corset is handling your posture, but we can work on that more later.”

With that Deedee stepped away and paid for the expensive salon trip. As Deedee was gone, Trent took her advice and began to try to walk around slowly. At Sara’s suggestion, he used the back of the rotation chair as anchor point and slowly walked circles around it. Deedee’s advice was echoed by the helpful salon assistant as the boy struggled to learn how to walk again. In only moments Deedee was back, but in that short time he had managed to at least figure out how to walk slowly without the help of an anchor point.

“So, let’s go babe. There is a steakhouse just on the other side of the parking lot, we can go get you a nice salad there.” Reaching out, Deedee handed Trent perhaps the most embarrassing item of all, his own pretty white purse. The golden CL initials across the front were unmistakable. Realizing that he likely was wearing a single outfit that was more expensive than all of his old clothes combined, he took Deedee’s long nailed hand in his and did his best to follow her out the door.

Does Tiffany put meat in her mouth for lunch?

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