Uncovering the Sissy Beneath Pt. 04

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional.

This is part four of my previous work. Be sure to read parts 1-3 if you wish to understand the background of this section.

After we reach the bottom of the stairs, Madam Victoria leads us back into the cell. She locks the sliding bars, and before stepping out again, Informs us that she'll be back a little later to spend some time with me.

As soon as the main door closes behind her, Sherry begins to cry. Embarrassed, she lays down on the bed with her face in the pillow.

My male instincts sink in and I feel the need to comfort her. Despite her being really being a boy, she looks very beautiful as a girl. "What's wrong I ask?"

"I'm sorry," she replies. She sits up and wipes her tears. I take a seat next to her, and she starts to hug me tightly. "I hate Mike, I fucking hate him, he's such an asshole."

Knowing what I had just seen upstairs, I was already feeling sympathetic. I was wondering how she even managed to hold in her tears till now. All I could think to say was, "I'm sorry you had to go through that."

"Ha!" She chuckles, "trust me, that was nothing. He must've been in a good mood today or something. I don't mean to scare you or anything, but I'll explain it the best way I know how. Mike is a sadist. An evil sadist, who only wants to torment me and whoever else crosses his path. He is completely heartless, and Daddy knows it too, but that's his brother, so he lets it happen. I'm sure you heard him mention last week. So last week, I accidentally, just slightly used my teeth while blowing him, and he... uh, well I'd rather not re-live it, but come on. How can I not use teeth. He's fucking huge! Look, I have had some harsh punishments from Daddy, but at least Daddy actually cares. I'm sure that must sound crazy to you right now, but he does."

She finishes wiping her face dry, and smiles at me. She can see I look frightened from what she just told me, so she gives me a peck on the forehead, which must have been the most comfort I had felt since I mistakenly showed up at that place.

"Anyways," she says. "Daddy wants me to teach you about cleanliness, and while showering and everything else that I'm sure you're familiar is important. There's a lot of extra work that goes into being a sissy. The number one thing you have to remember is that Daddy, Mike, and whoever steps foot in this house, are not into guys. They are attracted to young, clean shaven, slutty girls that can't think for themselves and care about nothing but looking pretty. Madam Victoria will help you get rid of your body hair and keep it smooth. She's a professional, and it doesn't even hurt when she does it."

"Okay..." I respond awkwardly wondering what I even look like without any body hair.

"Listen, I'm sure regardless of what they're making you say, you still think of yourself as a straight male. You need to channel that, look at yourself in the mirror, and make yourself into your ideal woman. Does that make sense?"

I respond "Um... It's an odd thought, but I guess it makes sense."

She continues, "like when you pick out your outfit, pick out what you would want to see a sexy girl in." She pauses for a second, "However, I think what Daddy wanted me to show you was how to handle our privates. That's the tricky part..."

"How do you mean?" I respond.

"Well, you have to keep in mind that we are sex objects to them. We must remain ready to be used as such at all times, and unlike genetic women, we get dirty down there, and that is not okay to them."

I ask, "you mean like when we go to the bathroom?"

"Correct," she says. "There's no avoiding that obviously, so we have to make sure we keep it clean down there before and after we go potty, and after we have sex."

"Other than wiping, what do you mean?"

"We need to regularly douche, and when that's not enough, give ourselves an enema."

She sees my face light up.

"Don't worry, it's not that hard, but you want to make sure you get it good and clean. I've messed that up a few times and the punishment is always a very unpleasant enema on top of whatever else they see fit. This is going to be embarrassing for me, but I have to clean up now after any mess Mike might've maid. seeing as we don't have a private bathroom in here, I'm sure we're gonna have to get use to using the potty in front of each other."

It was just like prison in the movies, I remember thinking.

She reaches behind the toilet, there was a hose with a spout connected to the plumbing. She demonstrates a few sprays into the toilet, and then squats over the toilet. She wipes off then points the nozzle up towards her hole and sprays all over. She explains, "right now, I'm just getting the outside good, but once you do that, you want to make sure you get your hole open as wide as possible, and get the water up there as far as possible."

She washes with the hose for a good minute and then stops. She grabs something from the drawer. This I was familiar with, as I had seen it in porn but never in real life. She pulls out some anal beads that are all on one solid string. She then takes a bottle of lube and covers the beads in lube. Slowly, she inserts them one by one until they are all in there.

"These beads are special because they go real deep. This will help us check to make sure nothing is there that'll get us in trouble."

I look away in horror.

"Umm, you might wanna keep watching what I do here, because it's about to be your turn!"

"What?"

"Ya, I'm not sure if he just wanted me just to show you or help you do it, but I certainly wouldn't want to take the risk for your sake and for mine." She informs me while she slowly removes the beads from behind. She takes a look, "all good." she says then proceeds to wash them in the sink. "Pull your panties down and pop a squat on the toilet, and don't worry. I'll help you, it'll be fine."

Hesitant, I pull down my panties, exposing her to my chastity device.

"Oh look," she interrupts, "that looks like my first chastity belt. As you can see, mine is much smaller than that. over time, your clit will get smaller, and you will also stop getting erections, so the devices need to be downsized from time to time."

She was teaching me so much, this was all so brand new to me, and so scary.

I take the hose from her hand and have a seat. I spray and it makes me jump. The flow was so strong, and it felt so weird. I had never used a bidet before, but imagined they were pretty similar.

"Try to stretch it a little bit, and get in there as good as you can."

After a while she tells me I can stop. She then holds the anal beads in front of me and asks, "do you want me to do this? I probably should so I can show you how to relax."

I shake my head puzzled, but agree.

"Why don't you lay down on your back and pull your legs up."

Embarrassed, I assumed the position.

She told me to breathe and relax my muscles as though I was releasing. After applying the lube, she began putting the first bead in which was the smallest. My first instinct was to tighten up, but she quickly corrected me, and told me to relax so it doesn't hurt. I can feel more beads going in while there is a moment of relief after each one passes, but then they kept getting bigger.

She also informs me that the increasing in size will help open me up a little for whatever may enter next. I think for a moment about the thickness of Mike's cock, and how that must've been at least three times as thicker then the biggest bead. I could barely handle a small bead, how could I possibly handle that!

The last bead was in and I could feel them all deep inside me. It was such a weird feeling. There was a pressure from the internal stretching, but it also pressed against my prostate, and I could feel my pre cum moving up into my shaft. There was something slightly relaxing about it.

"Are you ready? I need you to relax again." She begins to pull on the ring at the end of the beads. As my opening begins to stretch again, I push to assist and little by little they start to come out one by one. The feeling of them exiting was blissful, almost like a tension and release.

She pulls the last bead out and looks at the beads for any signs I might not be clean.

Thankfully, it was okay. I certainly did not want to experience a douche or an enema.

"Okay," she says. "The last you thing you want to be mindful of is making sure you are always lubed up. We don't have female anatomy so we can't get wet on our own. That's why it is important we keep it that way by applying often. Trust me, these guys do not want to take the time to lube up when they want it right away."

I double check to make sure there is still a good amount of lube there. Then all of the sudden the door to the cell room opens. It's Madam Victoria. "Have you two finished cleaning yet?" She asks.

"Yes. ma'am," Sherry replies.

"Wonderful. Well, Tricia, I'm gonna have you come with me for a little bit. Sherry, you stay here and wait on Master David.

Madam Victoria lets me out of the cell to follow her. We walk about halfway down the hall and then she opens a door to a room I have not been to yet. It appears to be a salon of some sort, with a massage table in the middle.

"Okay Tricia, I'm going to help get rid of all this body hair. Have you ever been waxed before?"

"No ma'am" I reply.

"Well don't worry, it's not that painful, I know what I'm doing. I'm going to need you to strip down all the way and then I want you to lay down on the table face up."

I take off all of my lingerie and do as instructed. She Started with my face, using a hard wax. I felt pressure at times, but it wasn't that bad. Slowly, she worked her way all down my body. All of my facial hair gone. All of my chest hair, gone. She then moved to the crotch. I guess she must've gotten the key from David, or had her own copy, so she removed my chastity device to get all the hair down there. I was scared, but I must say. She really knew what she was doing. It must've taken more than an hour in total to strip me down of all the hair except my head. Even flipping over and getting between my crack.

When it was all over, she had me stand up and look in the mirror. I nearly fainted. It was as though I was a kid again, I had no hair at all. I couldn't believe it, but my long legs, all bare, looked so lady like. She helped me get the chastity belt back on, and then told me to get dressed.

"We're gonna meet up with Master David and Sherry in the punishment room for a little bit. Don't worry, I don't think you are in trouble, but he would like to ask you some questions. Plus, we can show him your new look."

I didn't understand, If I was not in trouble, why were we going in there. I had yet to even see this room. Surely enough though, I followed her out into the hall and into the punishment room. My eyes lit up in horror when we stepped in. There were all sorts of strange devices and implements. I could hardly tell what anything was, but it looked like some medieval torture dungeon.

I stop investigating once I see Sherry. She is standing in the middle of the room with her head and hands in a stockade. Bent over a gymnastics style horse with her ass sticking out. Her panties are pulled down to the waist exposing her bare flesh, and there is a gag in her mouth.

"Come in and have a seat Tricia," David says as he places a chair right in front of Sherry. "I want you to sit facing Sherry. I'm going to ask you a few questions, and I want you to keep your eyes locked with Sherry's the entire time.

I also expect you to be completely honest, do I make myself clear?"

"Yes Daddy," I reply.

"Good, because if I don't think you're telling the truth, you will be in her position next."

Awkwardly, I remain staring directly into Sherry's eyes. She has a worried look on her face.

"Okay now Tricia, this morning, you forgot to call me Daddy, what did I say happens when you forget?"

I had a feeling that this was going to about her not saying Daddy. He did say he was going to punish her or something like that. I respond, "ummm, I get punished?..."

"Correct, but did I punish you this morning?"

I shake my head "no Daddy."

"No I didn't, I let you out of it, because you're new, but why else?"

I try to express as much sorrow as possible as I knew I had no choice, but to rat Sherry out. I couldn't lie "Because Daddy..., because Sherry was calling you by your first name and it made me forget." I can see in Sherry's eyes. She was getting mad at me.

"You're doing good Tricia, you did the right thing by telling me this. I went ahead and watched last nights recording and have confirmed this to be true. Now let me ask you this, about how many times do you think she forgot to call me Daddy?

"I have no idea Daddy, maybe five or six?"

"you're not too far off, it was seven." He turns facing Sherry. "Seven times Sherry, Seven!"

There's a long pause, then he turns to Victoria. "Madam Victoria, would you please hand me the long whip."

Sherry begins to protest, but her words are muffled by the gag. In my peripheral, I can see Madam Victoria grading a long braided leather whip, almost like it was out of an old western movie.

He takes the whip and displays it to Sherry. I can see her eyes tearing up fast as she shakes her head over and over again.

"Seven!" he shouts, "Seven it is then."

He proceeds to walk behind Sherry and distances himself a good ten feet or so away.

He then lays out the whip, and makes a couple light flicks of the wrist, I can see the whip snaking its way outward, followed by a crack in the air. Sherry flinches, trying to wiggle herself free, but she is held perfectly in place.

He looks over at me. "Tricia, you keep your eyes forward and pay attention. You need to see what happens to bad little brats when they forget their place." He then turns to Sherry, "Alright Sherry, stop moving around so much, you don't want me to miss now do you? Just hold still and accept the consequences. Let's get this over with."

Sherry tries her best to hold still. She looked so scared, and my heart was racing for her.

David cocks back his and arm and with one heavy flick, the whip flies forward, followed by a pop as loud as a firecracker. Her body jerks forward pushing against the stockade, and then a delayed scream followed, but was muffled by the gag.

There's a silence in the room as Sherry's screams become softer, but not for long as another flick of the whip cracks, and the screams maximize once more. Her eyes were barely open at all, but I know that she could see the horrified look on my face as well.

Crack after crack, seven felt like eternity with the long pauses in between. "One more to go Sherry." The last blow was by far the loudest, at least it felt like it, especially judging by Sherry's reaction as she kept screaming and screaming.

He hands the whip back to Madam Victoria, who remained silent the whole time. Then he just stands there waiting on Sherry to stop screaming. After about a minute her screams turn to moans, and her body becomes limp as though she was going to pass out.

"Tricia, what's my name?" He asks

"Daddy," I respond in fear.

He walks over to Sherry and removes her gag. A mound of drool hits the floor. "Sherry..." He says. "What's my name?"

"Daddy," she cries. "It's Daddy! I'm so sorry, please daddy, I'm so sorry.

"Come on Sherry, you know I don't want to hurt you, but you were bad, and I only punish you because I care about you."

Sherry nods her head yes, "I know Daddy." She was in a state of Stockholm syndrome, and as far I was concerned, I was soon to follow. He really had her convinced.

He unlocks and lifts the stockade allowing her to stand up. "Alright Sherry, you know what to do."

Sherry walks slowly towards the corner of the room with her panties half down making it difficult to walk. She never touches her butt once. She puts her face into the corner, and leaves her ass pointed out, just like he had me do the night before. My eyes nearly popped out of my head when I saw her ass. It was covered in welts so thick you could barely even see the shape of her ass.

"Alright Tricia, let's head upstairs and have some dinner, and Sherry, once you've had enough time to seriously think about your actions, let Victoria know and she'll bring you upstairs to eat with us." Finally, we leave that horrific room, and thankfully, nothing too bad happened to me.

To be Continued...