Uncovering the Sissy Beneath Pt. 06

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

This is part five of my previous work. Be sure to read parts 1-5 if you wish to understand the background of this section.

Sherry and I sat on the couch for a while watching fashion shows again. There was no discussion about what had just happened, she just acted like everything was normal. She genuinely liked these girly shows too from what I could tell. She seemed to get excited about certain outfits, commenting on how she would love it if Daddy bought them for her.

The only thing I could concentrate on though, is how the remains of cum and saliva from Sherry's tongue were slowly drying and crusting over on my face.

After watching tv for a while, Madam Victoria came downstairs. "Sherry, can you pause the tv for a second," she asks.

"Yes Ma'am." She says then pauses the program.

"Thank you Sherry. Tricia, I need you to follow me."

I stand up slowly and follow Victoria into the hallway, and she tells Sherry to stay put and keep watching tv. She opens a door to a room I have yet to see. It is dark when we first walk in, but then she turns on the lights. As though I should expect nothing less, I am once again freaked out by what I see. It's basically a storage room of various cages and restraints. Some look like dog cages, and others took shapes of different human body positions.

She takes my hand and leads me over to a square cage with wheels underneath that looks like it could fit a medium size dog. "So Tricia, Master David tells me you're struggling with your posture. He has asked that I help you correct it so you can arch your back better. So here's what's gonna happen. You're going to get on your hands and knees and crawl into this cage."

Concerned, I drop to my knees slowly, and look up at the cage wondering how I'm supposed to fit.

She quickly raises her voice, "I said crawl!"

I start making my way into the cage. Her tone frightened me. I had never heard her yell until now. I begin squeezing my shoulders in, and slowly work my way through the door. Surprisingly, I'm able to get my body in, but it's a snug fit with no room to move my arms and legs. After my feet pass the door. She slams it shut, slides the hatch, and puts a lock on it. Then she walks over and grabs a box. I can see her pulling these long wooden poles out of it.

She comes over to me and shows me one of the poles. "This, is how we are going to correct that posture." She takes the pole and slides it under my upper chest, keeping my shoulders raised high. "Go ahead and relax your shoulders."

The pole was actually kind of nice as it took pressure off of my arms to hold me up. She then takes another and slides it through the bottom, locking my elbows into place. Making any arm movement impossible. She then does the same with my knees, restricting any movement from my legs.

"Now, this is going to get a little uncomfortable, but I want you to arch your back as much as you can and lift your butt up in the air."

I raise my butt up and she slides a pole under my crotch, keeping it as high as possible. She then quickly takes another pole and presses it down on my back, bending it down as much as possible. I could feel so much pressure on my spine to stay that way, and after the pole was in, relaxing my back did nothing, it held me tight in that position. I start moaning in agony.

"No whining now, we can stop that too. Here, let me give you something to suck on." She takes a small dildo out of the box. Quickly she shoves it into my mouth muffling my cries. On the opposite end of the dildo there is a metal piece, which she mounts on to one of the bars in the cage. I am completely stuck in every way possible.

She begins rolling the cage back out into the hall. Leading me right back into the den. Sherry says nothing when I show up. She leaves the cage in front of the couch facing me towards the tv.

"Okay girls, have fun watching the rest of your show." She says as she walks back up the basement stairs.

After the room is clear Sherry stands up and walks over to me. "Aww, oh no, I guess Daddy wants you to work on your posture control."

I try to respond, but there's no way to form a sentence with the dildo stuck in my mouth.

"Don't worry, I know it feels uncomfortable, but you'll get use to it. trust me, I've spent countless hours in the cage. It works though, your back will be sore afterward but all that stretching is good for you. Try not to focus on it too much. Let's just enjoy the show for now."

I tried to concentrate on the show, but it was hard to distract myself from the aching of my back being bent. On top of that, the dildo kept gagging me and I was drooling everywhere.

I was stuck in that cage for at least an hour, and then finally Madam Victoria came downstairs. However, she didn't even acknowledge me. She just told Sherry that a couple of David's friends dropped by for lunch and that she should come upstairs to entertain.

Sherry is now gone, and I am left all alone watching shows geared towards women. After a few hours had gone by, I thought for sure they were going to leave me there all day. My emotions went back and forth, from sad to angry, and sometimes breaking down crying. Just adding to the pile of slobber at the bottom of the cage.

After hours of waiting, I start to hear David and another male's voice coming down to the basement. A man who I haven't seen before appears around the corner with David.

"Well, what do you think?" David asks the other man.

"Oh wow," he replies while staring at me in the cage. "She's already looking her part Dave. You said she's only been here a couple days? Great job man"

"Right!" David says "Although, I have to thank Victoria for helping of course, and Sherry too. She's been helping her, and It's nice to know she has someone to talk to now. I've been waiting a while for another to come around.

"Is She good to go yet?"

"Not quite yet, she's still a virgin, and needs to learn a few things. You know what though, she's learning to suck cock pretty well."

"Oh really? Mind if I take her for a spin?"

"Sure, why not, but she'll have to do it through the cage. I'm not ready to let her out yet.

Looking right at my face, the man replies, "even better. Won't have to worry about her moving around too much."

"Nope, she's not going anywhere. I'll leave you two alone though, I'm gonna take care of a couple things down here in the basement." David then walks away towards the basement hall.

"Well well," the man says as he leans down face to face with to me. "Looks like it's just you and me. Let's just see how good of cocksucker you really are. I see you got a little rubber cock you're sucking on right now, so you must like it.

He stands back up straight to undo his belt buckle. I can see the bulge in his khakis growing. quickly, he pulls down his pants and underwear. His cock springs up in front of me, and he begins to stroke it.

"You like the look of that?" He asks, knowing I can't answer.

Well let's get that fake cock out of you so you can get a nice thick tasty one to suck on."

He then takes his cock and slides it through the cage holes poking me in the face with it. I can feel his pre cum hitting my cheeks as he laughs at me. Then he bends over and starts unscrewing the joint that was holding the dildo in my mouth.

There's a quick sense of relief as he pulls the dildo out of my mouth. Then he asks, "Are you ready for me fuck your throat little girl?"

"Yes," I reply not knowing what to call him.

"Yes sir you mean?"

"Sorry, yes sir."

He looks at me with a angry grin, and then takes a deep breath. "That's okay, you're new so why would you know that right? Just do a good a job with my cock and we'll keep that mistake our little secret. Misbehave though, and I'll be cheering David on while he gives you a good spanking. Understand?"

"Yes sir, I'll be good sir, promise," I reply eagerly.

He puts his cock in front of my mouth, I open wide, as he has a lot of girth. Shorter than David's, but definitely thick. He shoves it right in, causing me to gag for a second. However I quickly gain control and relax my throat. He begins pumping in and out of my mouth. Fucking it slowly as if it were a pussy. I couldn't really move my head or anything, so the only thing I could do was let him fuck my mouth.

"Oh yes," he moans out. "Look at those pretty sissy lips of yours. Those lips were meant for sucking cock. It's a shame you've been putting them to waste all of these years. Let me feel that soft tongue too."

I keep my lips wrapped tight, and start to work my tongue on his head and shaft.

"Such a soft mouth too. Let's see just how far we can get this in there."

He then shoves his dick as far down my throat as he can. I fight my gag reflex as much as possible. Then he pulls out. I breathe heavily for a second, but he slams it right back in. Grabbing onto the edge of the cage he starts thrusting in and out of mouth as hard and fast as he can. At times I felt like he was going to hit my brain or do some kind of damage.

"Oh fuck yes, suck on this juicy cock you little whore." He shouts as he slows down a touch, allowing me to grip my mouth around him better.

I work my tongue the best I can and wrap my lips tightly around his shaft. I had to make him cum, my throat was getting sore from all the thrusting.

"That's it," he moans. "Oh yes, I hope your hungry bitch. I've got about a weeks worth of cum in here."

I start to freak out a little as I have no control over his dick, and as someone who has been dry before. I know how much a weeks worth can produce.

"Here it comes baby, get ready," he shouts, and leaves his pulsating cock halfway in my mouth. Then after a couple moans, I feel a forceful shot hit the back of my throat. It was shooting out like a squirt gun. Rope after rope, it kept filling up. It was getting to the point where I thought some of it was going to dribble out of my mouth, but I managed to stuff it in the sides of my cheeks.

Eventually it started to slow down, and the drops became smaller. I was struggling hard to keep it in. On top of that, the taste was much more intense and it was much thicker than what I had experienced so far.

Finally, he pulled away from my mouth. I almost dropped some, but managed to slurp it back up.

He laughs at me "Whoa now, don't drop it. That is a lot though, I won't make you gargle it, but let me see you swish it for me.

I close my mouth and swish it like it was mouthwash.

"Are you able to open your mouth now without dropping any?"

I tried my hardest to open, but couldn't open very wide.

"No, you can't," he laughs. "Alright then, give me another big swish, and then you can swallow.

"Finally," I thought. I swish my mouth again, and start carefully gulping it down.

"Good girl," he says. Then he presses his now soft penis up against my mouth. "Now kiss this dick goodbye, for now. I'm sure you'll get the chance to suck it again sometime soon."

I kiss it softly on the head, and then he puts it back in his underwear and pulls his pants up. Then I remain quiet as he goes and gets David.

They both come back into the room, and I hear David ask him if I did okay.

"She did great for not having much experience. I think she actually likes it."

"Oh of course," David replies. "She might not know it yet, but she does."

"Well maybe next time I'll get to try out that asspussy too huh?"

"Ya, she'll be good to go soon enough."

"Alright David, I'm out of here. You take care."

"Ya you too." David says as the man walks back up the stairs. He then looks down at me.

"Alright Tricia, looks like you did good there. I'll let you out of the cage now."

He grabs the cage and rolls me back into the room where all the other cages are. Once he puts the cage back where it was, he removes the pole that was forcing my back down. I was so relieved, but at the same time, I couldn't really move my back up easily. It was stuck sort of.

He slowly removes the rest of the poles, and then unlocks the door. "Okay Tricia, when you're finally able to get out of there, come upstairs. Dinner should be ready soon. I take it you know better than to try anything dumb while I leave you unattended right?"

"Yes Daddy," I'll be up in a minute."

"Good, and put this on. We have company over, and want you to look decent." He sets down an outfit on the floor, and walks away.

Slowly, I made my way out of the cage. After a few minutes, I'm able to gain a little bit of movement in my spine again and stand up. I grab the outfit that was on the floor. There is a pair of black tights with a purple floral design. It fit snug on my thighs and made my butt stick out. The top was a tight black sweater to match, which had words on the breast that said, "Daddy's girl."

I make my way upstairs, and even though I was unattended and outside of my cell. I had no thoughts of trying to escape. At this point, I felt it to be in my best interest to just go along with it. The thought of getting out of there would just bring me down, and I needed to find ways to stay positive.

I enter the kitchen, and everyone is sitting down at the table eating. Sherry is sitting on a mans lap who I have also never seen before. He is holding his fork in one hand and holding Sherry up by her butt in the other. He was very muscular and Sherry was snuggling tightly on his chest and rubbing his bulk arms.

"Well hello there cutie, what's your name?" the man says to me as I approach the table.

"Tricia sir," I reply.

"Aww, well come have a seat, Tricia." He points to an open chair next to David.

As I go to take a seat I also notice there is another girl sitting next to them. She looked asian, and was quite petite. She however, was seated in a high chair, like a baby would. I was quite confused as she also had a pacifier in her mouth and was wearing a messy bib. It was then I noticed that she and Sherry were wearing diapers. Although, Sherry had bright pink cartoon pants on over hers and a

Cinderella shirt. He was treating them like they were babies.

David introduced them to me, "Tricia, this is John and his 'baby' girl Stephanie. They have decided to join us for dinner this evening." John is very big on teaching girls like you what they missed in their childhood.

"That's right Tricia," he interrupts. "It's great to hear that you're accepting your new path but it's unfortunate that you missed out on all the lessons of girlhood you should've learned growing up."

"Whenever John stops by, or if we go over to his place, you can live out the early development you missed. You can play with dolls and watch some of your favorite Disney Princess movies. Sherry's got a favorite, don't you Sherry?

"Yes Daddy, I like Cinderella." Sherry responds to David.

We sit and eat for a while, and I watch John as he interacts with the two of them. Wondering if and when I would have to play along with this as well, they mostly just kept me quiet to eat and observe.

After I finish my plate, David instructs Sherry and I to head back to our room. Sherry begins walking towards the basement steps, I follow as she struts down the stairs in her diaper. As we walk towards the cell, Madam Victoria joins up with us to lock the doors.

Sherry immediately changes out of her clothes and removes her diaper to change back into a sexier pair of boy short panties and pajamas. She then speaks to me. "So ya... That was John... He's actually really nice, but it takes some getting use to as his approach is much different than Daddies other friends. He's very nurturing though, so it's a nice break from the usual day to day here. How's your back feeling by the way?" She asks.

"Sore, but better than before," I respond.

"How did it go with Daddy's friend? I saw him heading towards the basement earlier."

Embarrassed, I respond. "Well, he made me give him a blowjob through the cage, and just kept asking Daddy about getting me ready..."

As in perfect timing to the topic, we both look down on the bed, and see two toys laid out on the bed. One was a butt plug, and the other, was clearly a dildo connected to a strap on device. Next to them was a note which read "Sherry, I'm going to be hosting another event very soon, I expect Tricia to be ready by then, I'm leaving it up to you to help her get ready for me to take her virginity, at least by the end of the week. I have left you with these two toys for the evening. You know what to do with them... P.S. I've been watching the security footage and I see the way you two look at each other. I think it's great that the two of you are becoming fond of one another, and since I know you are both safe and locked up to which neither of you can pleasure one another, I am giving you my permission to be intimate. In fact, I think maybe the two of you could start making me some tapes to show my friends;)"

My heart started racing immediately. Sherry knew I was scared so she hugged me from behind, whispering that it was gonna be just fine. I knew I was going to have to get ready for it, but this made it clear. In less than a week I was going to know what it's like to be fucked like a girl. I kept my head up though, and didn't shed a tear this time. I was somewhat relieved that the only person I could trust, was going to help see me through it.

I turn around and hugged Sherry back. She kisses me on the cheek and whispers "Don't worry, I'm gonna help you get ready. We can have fun too, it doesn't have to be scary. Go make sure you're clean though, remember, we're on camera.

I go get the beads out of the drawer, and do the bidet routine that she had taught me. I knew I would have to do it without her help this time. I was also beginning to understand just how brave she was. She had been playing along with this crazy situation for way longer, and kept her head high. In some way, I wanted to reach that level too, I was starting to admire her as it sounded like she did not have a mentor when she was at this point.

After I finish getting clean, I lube up heavily and wiggle my tights back up.

"You look hot! Come lay down with me," Sherry says making deep eye contact with me. I started walking toward the bed, and she holds her hand out to connect with mine. She scoots over, gently pulling me onto the bed to spoon with me. It is then that I can feel a little poke coming from her pajamas. It's her chastity device rubbing against my butt. Then, she begins slowly dry humping me.

Feeling slightly turned on, I begin to push my butt back more so she can rub on it easily. It's silent for a minute, but then I decide to turn around and face her. She begins to caress my face with her hands as we awkwardly stare into each others eyes. Slowly though, our faces get closer and closer till eventually, we connect lips.

After one short nervous kiss, we both realize we enjoyed it, and immediately begin passionately making out. Rubbing each others backs and occasionally down to the butt cheeks. It goes on for about 10 min, till eventually she starts stripping me down.

After my pants and shirt come off, she puts her hand down the back of my panties. Working her finger through my crack. Eventually she reaches my lubed up hole and starts to wiggle her finger on it. "relax," she says, and then slowly starts sliding her finger in. Moving it around inside. "Are you comfortable?" She asks.

"Yes," I reply, "it actually feels kind of nice."

She removes her finger, slides my panties down all the way, and then takes off her pajama bottoms. "Hold on a second," she tells me, and then stands up to grab the strap on. She struggles to figure it out, so I do my best to help, and eventually, we get it on her.

"Okay, lay on your back, it'll be easier this way," she instructs me.