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Chapter 5 by RachelDaws RachelDaws

Does Trent wake up happy?

Hell no!

The clock on the bedside showed 7:36am as Trent’s eyes opened up. A wince instantly covered his face as the pounding in his head from his substance **** of the day before. The feeling in his throat and his parched lips caused his tongue to flick out and run over his lips. A slightly salty taste that he couldn’t quite pinpoint teased his tongue as Trent fought against the headache that occupied the majority of his partially awake mind. Groaning, Trent sat up on the bed slowly, his hands cradling his head as he sat there. Only the incessant need to urinate was strong enough motivation to stand up and make his way to the bathroom.

Stepping into the bathroom it took Trent a moment to remember why the countertop was covered in makeup and hair products. Shaking his head at the insane situation that he had come home to, Trent hooked his fingers in the waistband of the side of the underwear he had on and tried to pull it down so he could piss. With his eyes half closed, Trent fumbled with the panties. The elastic waistband of the lingerie caught on the lock of his cage and made it so that pulling the panties off was more difficult than it should have been. Finally opening his eyes fully, Trent looked in the mirror and took in the panties around his waist, as well as the bright pink cage locked around his small dick.

“What the fuck?!!” The words rang out into the house as he yelled. Wanting to stop and figure this out, his body didn’t give him the chance. The need to urinate that had only been a desire moments ago swiftly became a biological imperative. Finally extricating himself from the underwear, Trent collapsed down onto the toilet seat and began to release his bladder. The groan of release as his body drained itself echoed out through the open door as he leaned back against the back of the toilet, finishing his urination. Thinking that he needed to somehow clean himself, Trent reached down and wiped himself quickly.

“Feeling better baby-girl?” Deedee’s feminine voice spooked Trent as his gaze lanced up to see the beautiful woman his father had become standing there watching him use the toilet while what must have been her panties now sat gathered around his ankles. Again, his father stood there looking like an extra from any of the porn movies that he spent hours watching. Deedee’s casual outfit was something that most girls would consider date worthy. Perched in white 4 inch, Deedee’s taut legs were covered by a pair of skin tight skinny jeans. The oversized pink crop top she wore sat off of one shoulder showing a bra strap of her pale pink lingerie. Dedee’s tight toned stomach wouldn’t have looked out of place on a girl half her age.

“What the fuck happened to me? Why is this thing on me? Why am I wearing panties?!” Trent’s voice grew louder with each question as he stared up at the woman in front of him. The pounding in his head made it hard to remember the night before, and even parts of the day seemed foggy and missing. Trent’s eyes finally took in just how sexy the feminine form in front of him was as he sat there. Even knowing this wasn’t a real woman, even knowing that this was actually his feminized father, Trent’s cock tried to harden in its small plastic enclosure. Something about the way she stood, with one hip cocked to the side and her long nails and perfectly made up face just seemed to scream sex at him.

“Oh hunny, did you forget what we talked about when I got home last night? I know you were kinda drunk but I didn’t realize you were that drunk. Maybe we should have waited to enact some of the changes you begged me for…..” Deedee let the sounds of her words fall off as she moved out of the room. “Well, done is done. If we are going to make the appointments you begged me to make, you are going to need to hit the shower. I can’t take you in there smelling like sweat, ****, and looking like you spent all night playing with that caged clitty hun.”

“Appointments? Changes?” Standing up, Trent reached down and pulled up the panties. The string settling into his ass crack made him remember just what was going on. Pushing the lace object back down he stepped out of them and moved into the bedroom. “What the fuck are you talking about?”

Deedee shook her head and giggled softly, her raven locks bouncing around and framing her face in soft waves today. Continuing to move about her bedroom and lay out clothes on the bed she glanced up at her son momentarily before speaking. “You really don’t remember? Well this is gonna be interesting” The lie came out of her bubblegum pink stained lips easier than she expected. “When I got home last night, I found you laying in my bed crying and wearing my panties. You can keep those by the way.”

Trent’s face scrunched up in thought as he did his best to remember his day after beginning to go through his father’s bar. The anger had pushed him to drink excessively throughout the day. Ignoring even lunch and dinner, he had consumed **** with only the drive thru breakfast he had managed to grab on the uber ride from the bus station. The whole day after about noon was blank to him as he stood there stark naked.

“Look, just get me the key for this fucking thing.” Looking around the room for his clothes, Trent’s eyes widened more and more as he realized they weren’t in sight. “And what the fuck did you do with my clothes?”

Deedee laid out a white sweatshirt much like the one she had on next to a pair of black leggings on the bed. Of course a pair of black lace thong panties sat alongside. The outfit was something she had worn before her surgery for working out, before she had converted her garage to the home gym it was today. “I didn’t do anything with them hun.” This time Deedee kept her gaze pinned on anything but her son. She knew that the next hour was going to be crucial. Plus, they really did need to leave soon to make their scheduled appointments. “You took them out last night and dropped them in the trash cans. I did my best to stop you, but I’m not as strong as I used to be. The truck picked them up at about 5 this morning.” Thankfully that part was true. There was not a chance in hell of her son’s clothes coming back to this house. “Now, I need you to get in the shower and clean up. I’ll bring you in some water and some aspirin for that headache I know you must have. Let’s get you cleaned up and we can figure the rest of this out after ok?” Moving up to him, she gently pushed him back towards the bathroom.

In a state of shock, Trent allowed himself to be led. The hot steamy water poured from the rainfall shower head and began to soothe the boy’s headache slightly. “Soap and loofah there on the right. Don’t worry about shampoo and such. They are gonna do our hair today too.” Turning around and bending over at the waist, Deedee took a moment to collect the lace panties her son had slept in. Unable to miss the perfect heart shaped ass that was being presented to him through the clear glass doors, Trent stared at his father’s cheeks and once again winced at the swelling against his cage.

As he slowly began to clean himself, Deedee went out into her bedroom and collected the already laid out glass and handful of pills. While it certainly held a number of pain pills, nestled among them was also a pair of valium and some of the pills that Deedee herself took each day to help with her figure. Taking the **** and water back into the bathroom she opened the door to the shower. “Give me your hand.” It felt odd to Deedee to be commanding anyone. It had been over a year since she had felt like she had a position of power over any human being. The surge of adrenaline as her son complied without thought was intoxicating.

Looking down at the pills in his hand, Trent didn’t recognize most of them. Before he could do anything, his father was speaking. “I brought you some vitamins too. They should help you with the hangover. Trust me, I know.” Winking to her son, Deedee handed him the glass of water and stood there waiting like a patient nurse. Unnerved by the complete insanity of the situation and wanting nothing more than to silence the pounding inside his head, Trent slipped the pile of pills into his mouth and drained the glass of water. Deedee’s manicured fingers gripped the glass easily and moved away. “Now hurry up, we still have to get you dressed.”

As the warm water soothed his muscles and the pills began to course through his system. Trent began to feel better. Soaping up his body and ridding him of the stale booze induced sweat that covered him brought a semblance of life back to him. Yelling over the door of the shower and hoping his feminized father heard him, he spoke up. While he couldn’t refute his father’s story, there was no way that he had done all the things that Deedee kept saying he did. Turning off the water, he stepped out to find that the only visible towel certainly wasn’t large enough to wrap around his body. Drying off with it and leaving it laying on the floor. He stepped back into the bedroom and faced his father.

“Look Dad, I don’t know what the fuck is going on. But it stops now. You did something to me, **** the booze you had here or something. I don’t know. Just give me back my fucking clothes and I’ll go stay with a friend or something. Cause I’m not doing this. Just because you are some sissy freak, doesn’t mean that I am too.”

While yesterday this kind of outburst had shocked and frightened Deedee, today it did nothing to her. The sight of her son standing there naked, his caged clit dripping a bit of water was enough to make her giggle. Fighting back that instinct she thought for a moment. “Hunny, your clothes are gone. You did that. You put that thing on.” Stopping for a moment she spread her legs and looked down at the incredibly skin tight jeans she had on. “I certainly don’t wear one, especially not that small. You’d be able to see it in these.”

The flush of embarrassment crept up Trent’s cheeks as he realized that his feminized father had just said he had a small dick, if not in those words. His eyes locked onto her crotch and he realized that she was right, there was no way to hide the plastic nub in those jeans. Especially with the lock attached to it. “Still… I… need my clothes.” The shame of the whole situation was suddenly crashing down on him. What was worse was that he kept looking up at his father and feeling things towards her that he should only have felt towards real women. “Can’t you just go get me some?” What had been statements of anger and demands moments ago were slowly shifting more towards the whining and pleading that Deedee was used to coming from her son.

“You got rid of them. Not me. It is bad enough that you came home yesterday and said the things you did to me. Let alone the fact that you dropped out of school!” Slowly Deedee was beginning to enjoy this feeling of power. Her mind raced and her lust swelled as she pushed harder and harder against Trent’s sense of self. The lies and half truths came easier as she went. “You told me this is what you wanted? You begged me to take you to the salon today. Hell, I had to talk you out of wearing a skirt!” Her eyes widened as she realized that she might have gone too far with that last statement. Pulling back the exaltation that rose in her, she tried to slow the situation back down. “Look. Just put some clothes on and let’s go. The salon is at the mall. If you don’t want to do this by the time we get there, I’ll give you my card and let you pick out some clothes on your own.”

Finally Trent felt like he was getting somewhere. The idea of him asking to wear a skirt felt insane, even with all the ridiculous things happening around him he felt like that was something he wouldn’t have done. Still, his father seemed so relaxed about all of this. So matter of fact. It didn’t help that even as his headache began to subside and the **** surged through his system, he still couldn’t remember any parts of the latter half of the day before. Looking down at the clothes on the bed he sighed. “Is this seriously the best you have?”

The resignation in Trent’s tone told Deedee everything she needed to hear. “Yes. I don’t know if you’ll fit any of my jeans, and it isn’t like I own a lot of pants. I tend to prefer the freedom of a skirt.”

Stepping up to the bed, Trent reached down and picked up the leggings. “Fine, but I’m not wearing fucking panties. I am not a god damned sissy.” Sitting down to slip the skin tight pants up his legs, Trent realized he was still wearing the cage. “Fuck why am I still wearing this? Get me the key for this thing.”

Here was the time that all of the acting submissive that Deedee had done for the last year game into play. “Well, hunny, you see…” Chewing on her plump pink lips, Deedee did her best impression of the apologetic slut. Squeezing her arms in front of her made her impressive tits stick out even more as she leaned down in front of her son. “See, you kinda threw it out with your clothes. You had demanded the key while we were talking about things. I didn’t realize it till I went looking for the key while you were in the shower. I saw you loop it onto your other keys, but when I went looking for them, I couldn’t find them. You must have tossed them out with your clothes.” Tilting her head down, Deedee stared up at Trent through her long false lashes. The look of innocence coupled with the obviously flirty nature of her poses made it impossible to feel like such a creature could have done anything wrong to you on purpose.

Realizing just how fucked he was, Trent fell back onto the be and screamed expletives into the air. As the anger fled his system, the Valium began to pump into it more. The frustration boiled over, but where before anger had been his major mode of expression, now came something different. Slowly, tears built up behind his eyes and began to leak out the sides. “I don’t want this. I’m not a freak.” The words were whispered into the air as the boy laid there with leggings pulled up to his thighs and a pink cock cage nestled between his thighs.

The sight of her son crying almost made Deedee reconsider her plan. It was in every parent’s DNA to try to stop their child from crying, to stop anything that would cause their child that sort of emotion. Just as she was about to step forward and end all of this, she registered what he had said. Suddenly, the part of her that still felt like his parent snapped and shattered into a thousand pieces. Derek had been his father. Deedee was not. Deedee was also not a freak, sure her life wasn’t what most people would call normal. But that was stupid, no one was normal. Deedee loved who she was becoming, and she hated the ignorance and hatred that came from that simple statement. “Shut up Trent. I told you I would help you fix the problems that you created. I’m tired of your whining and yelling. Now, put my clothes on and let’s go. I’m not going to miss my appointment at the salon just because you want to sit here and throw a childish tantrum after I gave you everything you asked for last night.” Tossing the little frilling ankle socks that she still had from a night of roleplay with one of her work customers on his chest she stalked out of the room. “I’ll find you some shoes, cause it looks like you threw those out too!”

Sitting up, Trent slowly and mechanically began to get dressed. It wasn’t until he had pulled up the leggings, slipped on the top and was beginning to pull on the frilly socks that he realized that he was simply doing as he had been told. Looking down at the socks as he pulled them on, he sighed as the frills stood out against his slim ankles. Swallowing loudly he looked up in time to see his father march back into the room on her high heels. It occurred to him at that moment that she had been moving around on the pencil thin stilettos all morning in a way that hadn’t even seen his girlfriend do. Reaching up he took the thankfully normal looking sneakers and began to pull them on, only to realize that they were far from normal. “High heeled fucking sneakers? Holy shit, how big of a fucking girly girl are you? Don’t you have any normal shoes?” The hidden 3 inch heel in the hightop pushed his calf up enough to show noticeably on his legs.

“No, I don’t. I’m sorry I didn’t plan for my son to drop out of school and need some work boots to go to the mall. I wear heels, either wear them or stay here. I’m done caring.” Deedee’s tone was clipped and harsh as she tossed a matching black ball cap onto the bed. “There, I know you don’t want to be seen with your freak of a parent. So use that to hide yourself. I’ll be in the car. If you aren’t there in 5 minutes, I’m leaving without you.”

Trent stared at the wall as he heard Deedee’s heels click along the hardwood floor of the hallway and front room. Closing his eyes, he slipped his second foot into the other sneaker and stood up. The angle of the shoes caused his legs to lengthen and tighten up. His already bouncy ass was pushed out even farther as his body tried to compensate for the new angle. The skin tight leggings only enforced this with the ruching in the back. Standing there, Trent heard the engine of the car in the driveway start. Realizing that he couldn’t be left like this, he reached down and snagged the ballcap before trying to run out the front door. Slipping the hat on and pulling it low over his eyes he stepped out into the light.

Deedee’s eyes were locked on the door as she sat there in her car. So she had a full view of her son stepping out into the morning air in her clothes. This time it was impossible for her to stop the giggle that burst from her lips as she noticed that the leggings she had given him were much more sheer than she remembered. The pink of the cage stood out through the black fabric and was easily visible. Seeing him move in heels made her wince as he stomped up to the car and slid in as quickly as possible. That was a problem for later though. Without another word she pulled the car out of the driveway and drove off down the road towards the mall.

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