Uncovering the Sissy Beneath Pt. 05

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 1-4 if you wish to understand the background of this section.

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Dinner might've been the most normal thing I had experienced at this place. A little awkward at first, but when Sherry came up, she acted as though everything was normal.

Other than having trouble sitting down, which I'm surprised she was able to do at all. I mean, my bottom was still sore to sit on, and it had been a good 24 hours since I had my whoopin.

After dinner, Madam Victoria took us back down to the cell. As we walked in, she whispered to Sherry, "Daddy's gonna let you two sleep together again tonight, even though you were naughty. He's trusting you to help Tricia as she transitions into this new chapter of her life. You can watch some TV, but lights go out at 11, understand?"

"Yes Ma'am."

"Good, okay goodnight girls."

"Goodnight Madam Victoria," we reply.

After Victoria leaves, I turn to Sherry to apologize. "Sherry, I'm so, so sorry, I didn't know what to do. I forgot to call him Daddy this morning, and he questioned me."

"It's alright, Tricia," she says trying to calm me down. "You did what you had to do, and it was also the right thing to do. However, in the future, we have to make sure we correct each other, because we will both be punished no matter who tells on who. We have to tattle on each other though if it comes down to it. He will always find out the truth one way or the other, and you definitely don't want to be caught in a lie.

"Okay," I respond with a concerned grin.

She leans in and hugs me. "You look good by the way," she says. "Did the waxing hurt? You did have a lot of hair..."

"It wasn't as bad as I thought it would be," I respond. "A couple areas did hurt though. It's so weird, I'm not use to this at all. My legs are ridiculously smooth."

She chuckles, "Ha, ya it definitely takes some time, but I think it feels great being free of all that."

"I can see that, I guess." I skeptically reply.

Sherry interrupts, "Hey, let's get changed into our pj's so we can cuddle and watch tv."

We begin going through the drawers to pick out something out. Sherry hands me a lace piece of lingerie. "Here, this is called a teddy.

You should wear this to compliment your new hairless look. It'll make Daddy happy, I'm sure."

It was basically a one piece, I stepped into it, and began pulling it up. The back of it went up like a thong, and that felt weird. I was not use to having underwear ride up my crack like that. I pull the bra straps over my shoulders. Sherry helps me make sure everything is snug, and then hands me a matching nightgown.

"You look hot!" She tells me. "Take a look in the mirror.

Frightened by what I looked like, I slowly peak into the mirror. Other than my short hair, she was right. I was actually looking very feminine with it on.

She puts on something nice herself, but a little less risqué. We hop under the covers and she clicks the TV on with the remote.

I didn't recognize any of the channels she was flipping through. "Is there anything normal on here?"

"No, Daddy blocks most stuff on these TV's. Everything is pretty girly. A lot of fashion shows, and such." She turns on a runway competition show. "Here, this is actually good. I learned a lot about make up and everything watching this."

I should've figured he was doing absolutely everything possible to brainwash us... we laid there quiet and soon enough, eleven o'clock hit. So we turned off the TV and drifted off to sleep.

The next morning, after the alarm went off, Sherry pulled me out of bed. "Come on, we have to get ready. I'm gonna do your make up today as well, so no time to waste."

I had trouble waking up. I was having several nightmares, after seeing what happened in the punishment room. I kept thinking I would wake up and this was all just a bad dream, but sure enough the nightmare continues in real life.

I have a seat by the dresser. Sherry pulls out a variety of different things. Most of which was un familiar with, but she explains what everything is and shows me in the mirror the basics on what to do. I learned about foundation, we even put on fake eye lashes. She also gave me a quick manicure and pedicure. The final touch was, getting a wig on my head. We decided I would do dark brown hair which was also my natural color.

We were just about to pick out some outfits for the day, but the door to the room started to open. It was Daddy, "Good morning girls."

"Good morning Daddy", we reply.

He stops and takes a look at me with my new look, I felt ridiculous, but I started to see a stare I had never seen from any guy before. It wasn't aggressive, it was lustful. "Well well," he says eyeing me up and own, slowly sliding the cell door open. "is this your work Sherry?"

"Yes Daddy." she responds.

"Good job princess. I mean, if i didn't know any better, I wouldn't even be able to tell there was a wannabe male beneath all that."

Sherry looks over at me, as if I'm supposed to say something. I nervously respond, "uh,... thank you Daddy."

"Oh, learning some manners are we? Your attitude surely is changing quickly. See, your old daddy should've taken the belt to you when you needed it, but I'll make sure you get the discipline you need."

I started blushing, so many feelings were coming over me. I was scared, confused, embarrassed, yet somewhat aroused. I had never experienced someone, much less a man, treat me like this. It was different than anything I had felt before.

He looks over to Sherry, "Sherry, I want to spend some alone time here with Tricia. Why don't you go to the den and find something to do for a little bit."

"Okay Daddy," she replies.

Sherry, exits the cell and the room, closing the door behind her. David slides the cell door closed.

He walks over and begins to fondle me while I stand there. He then whispers in my ear. "Well, don't you look extra slutty in that lingerie. If I didn't know any better, I'd think you were craving a nice large cock inside you" He grabs my ass tight, "are you looking for a nice hard cock to fill your soft little sissy holes with?"

I gasp a little as I don't know what to say, but he interrupts me. "haha, don't you worry, I know you're still a virgin, and I'm not gonna take that from you yet, but I do want you to get it on your mind. Maybe ask Sherry to teach you how to use some toys so you'll be ready. Because I'm not gonna wait forever, understood?"

"Yes Daddy," I respond, but in my head I'm scared as I can't even imagine the torment it'd be to have him penetrate me.

"Good girl. For now though, I need you to keep this cock drained somehow, and I know your slutty little mouth can take it. So why don't you get down on your knees and give it some attention."

I hesitate for a second, but he raises his hand back to slap me, and I drop to my knees immediately.

"You can act a little more enthusiastic about it whore! you know you want to suck it again so unbuckle my pants and pull it out. Unless of course you wanna go wait in the punishment room, and I'll get Sherry to do it?"

I shake my head, "no Daddy, please, l'll do it! I'll suck it."

He calms down a little. So I reach my hands out, to undo his belt buckle. "Look familiar?" He asks. "I believe thats the same belt you got your bratty little ass whooped with the other night."

I gulp, noticeably as I continue pulling down his pants. As I start to bring them to his ankles, he grabs my head and pushes it towards the bulge in his briefs. My instincts kick in and I rub my face against it like he had me do before.

"My my, you really are eager to get your lips wrapped around this big dick aren't you?"

I Nod my head yes as I look up at him. I'm trying to remember how Sherry did it with Mike. I thought that maybe if I just went along with his game, then he might just finish faster and it'll be over with.

"Alright Tricia, that's enough teasing. Pull it out now and get to work."

I grab the elastic on his briefs and yank them down. His dick sprung out of the front and hit me on the chin. He laughs at me, "ha, you like having your face slapped with Daddy's cock?"

I try to open my mouth, but he pulls his dick back and slaps it across my cheek. I flinch as he does it a few more times.

Finally, he holds still and I'm able to wrap my mouth around the tip. I can taste some of his pre cum and feel a little bit of wetness left on my face from wear his tip smacked against it. I figured I had him going pretty well from the moment he saw me in my lingerie, so I slid it down my throat as far as I could. I was determined to get it over with as quick as possible.

I began bobbing my head back and forth, occasionally moving my tongue around the the tip and sides. I was loosing balance though, so I had to do something with my hands. All I could think to do is was what I had seen in porn before. I held on to his butt. Then he moans out, "that's it, grab onto it. You like the way Daddy's ass feels?"

I nod my head and yell with my voice muffled by his cock, "yes Daddy." The feeling of my vocal chords on him must've nearly made him loose it. He pulls out of my throat for a second, and I see his cock throbbing in front of my face, dripping wet with my slobber.

He grabs my cheeks together pulling at my mouth "Trying to make me loose it? I know you wanna be Daddy's little cum dump, but I'll give you this nut when I'm ready understood?"

"Yes Daddy."

"Good, now hold still for a second." He walks over to the bed and has a seat on the edge.

"Now slowly, crawl on all fours over to me. Keep your back arched down with your ass up."

I put my hands on the ground, and bend my back lifting my ass as high as possible. I slowly crawl on all fours, trying my hardest to keep my back arched.

He shakes his head in disappointment. "That's the best you can do? We're gonna need to correct that posture young lady."

Once I get in front of him he starts to play with my lips again. "So you like the way my muscular, hairy ass feels in those soft little girly hands of yours? Well that's what a real mans ass feels like, and you're gonna learn to worship it whore."

He lays on his back down on the bed and pulls his legs back towards his chest. I can see his hairy hole looking right up at me. I'm shocked and horrified at the sight. Then, he orders me to kiss both of his butt cheeks.

Reluctantly, I give into his orders, and begin to kiss his cheeks back and forth. "Good girl," he says. "Now all that's left is the middle."

With my lips on his right cheek, I freeze in place, hoping he was joking.

"Did I stutter?"

"No Daddy."

"Well then pucker up and start kissing that asshole. You know, I'm getting a bit tired of all this hesitation from you. The next time I tell you do something, you get to it right away or you're gonna be bent over this bed in tears while you get another good strapping Missy."

I close my eyes tight and go in for the kiss. I had never even done this with a girl, much less some strange man, but I give him what he asks for. He tells me to keep going, so over and over I again, press my lips onto his hole.

"That's it," he moans out. "Now let me feel you lick it."

I dared not hesitate this time, so I stroke my tongue through his crack, passing his hole. I gagged a little, but it didn't actually taste bad, it was just the thought of what i was doing that got to me.

"Oh come on slut, don't play that gagging bullshit with me, you know you like how it tastes. Now wiggle that tongue on it. Get it in there nice and deep."

What could I do, I had no choice. Sure enough for the next 10 minutes, I was doing circles around his hole with my tongue, and digging it into him as deep as I could. How much more humiliating could it get, I thought.

Eventually, he wanted me to continue with his blowjob. He dropped his legs back to the ground and shoved his cock right back into my mouth. Pulling on the back of my head, I was starting to become use to feeling his head hit the back of my throat without gaging.

All of the sudden, he pushes my head off him and stands up. "Alright, I want you get up on your feet and sit pretty for me, like a dog begging for a treat."

Having a trained dog in my childhood, I knew what he was referring to. I moved my body up and got into position.

"Okay, now a want you to hold that position, and without using any words, beg for your treat."

He strokes his rock solid cock in front of my face, and I do my best to give him the desperate puppy eyes. I also stick my tongue out in anticipation for him to cum in my mouth again.

"No no no," he says. "Not this time. No, this time I want to cover that brand new soft face of yours. Sherry did a good job with your make up, but let's just put one more finishing touch on it. So close your mouth and close your eyes, because here comes your treat bitch."

I couldn't believe he was about to give me a facial. At the same time, I figured it was better than having to taste his nasty spunk again. So I do as told, and get my face ready.

He starts to moan with pleasure. A couple seconds later, I feel the first squirt blast me across the face. Trying my best not to flinch and keep my face still, another shot hits me right on my closed eyelid. Then another went up my nostril and began leaking down over my lips. Rope after rope of cum, he made sure to cover every part of my face. Eventually, the blasts turn into drops, and slowly but surely, he drains out every last drop.

Feeling completely degraded, I wait with my face up, breathing in the strong smell of his fresh load. I hear him rustle through his pants pockets and pull out his phone. He starts taking pictures of me.

"I wanna keep these photos for memories of your first facial. I think I'll send a pic to my buddies as well. I'm sure they'll be eager to see what our new sissy looks like. You can drop to your knees again, but I want you to remain face up. Just don't let any of it drip."

I was glad he let me drop back to my knees, I was having trouble holding myself up in that position. I felt so humiliated. How on earth could I ever come back from this. Even if he eventually let me go, I'm gonna have to live with this memory for the rest of my life, and what was I gonna do to explain why I don't have body hair anymore. I was beginning to accept that I was just gonna have to go along with everything. Thinking about the outside world and ever seeing it again, was becoming something I'd rather not think about too much.

"Okay Tricia, I'll be right back. I want you to remain just like that." My eyes are closed, but I hear him leaving the room. I wait patiently for a minute or two, and then I hear the door open.

"Take a look Sherry. Doesn't Tricia look pretty with Daddy's cum all over her face?" He had brought her back into the room to see me like this.

"She does Daddy," Sherry responds.

"Oh come on now, you're not jealous of her now are you? Don't worry, that's what I brought you in here for. You're gonna help clean it up. Why don't you go lick it off her face."

"Oooh, Thank you Daddy!"

I can hear her making her way over to me. Sherry gets down on her knees right in front of me. Next thing I know, I feel her tongue working up the side of my face. Cleaning the cum up off of my eye's and nose.

"Don't swallow yet Sherry."

Obviously her mouth is full so she does not respond. She just continues slowly lapping up every drop. Eventually bringing her lips to mine, slurping what was resting between my lips.

"Okay Tricia, I think your eyes are fine now. Go ahead and open them."

My eyelids feel sticky, but I manage to open them without a problem. I could see Sherry staring directly into my eyes as she kisses and licks my face.

"Got it all Sherry?" He asks.

She nods "yes"

"Okay then, head back, mouth open, and gargle it real good."

I watch as Sherry savors his load, gargling and swishing it around her mouth.

"Alright Tricia, your turn, mouth open."

My eyes lit up! What did he mean 'my turn.'

Sherry nudged me before I hesitated, and I opened my mouth. Then she lifts her mouth right above mine, and starts dripping her cum filled spit into my mouth. I start to gag. She began softly rubbing my shoulders to calm me down. Some how, it helped. She was very good at keeping me comfortable.

My mouth filled to the brim with her saliva. It tasted like cum flavored mouth wash, and was very frothy.

"Gargle Tricia," He ordered.

My mouth was so full, but I did the best that I could to gargle and swish it like Sherry did.

"Alright Tricia, I want you to give Sherry half of it."

Sherry, aimed her face up again, and I leaned over to dribble it back into her mouth. I did my best to eyeball what was half. It sure looked like her mouth was full, and mine still felt pretty full too.

"Okay girls on my count, you can swallow. 3,2,1."

Sherry caressed my face as we both take several gulps, doing our best to get it all down without gaging.

We open our mouths and display to him that all of it is gone.

"Good job! That's all for now girls. I tell you what, since you've been so good, you can go hang out in the den and watch TV on the big screen. Just don't watch anything you know you're not supposed to.

We both stand up and follow him into the main room in the basement, remaining quiet while we wait on him to go back upstairs.

To be continued...