Uncovering the Sissy Beneath Pt. 07

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

This is part seven of my previous work. Be sure to read parts 1-6 if you wish to understand the background of this section.

Three days had gone by, since Sherry and I had our intimate session together. We had practiced multiple times after that night, and while I was struggling to get used to the increasing sizes of dildos used, I was becoming much closer to her. I loved making out and feeling her body against mine when we would cuddle. Whenever she wasn't around me though, I was required to wear a butt plug to keep me stretched at all times. Just like the strap on, I had to keep increasing the size.

David was absent quite a bit of the time, and said he was busy with work. Occasionally though, he would come down and make one of us suck him off.

The extra time Sherry and I had together in the cell, gave me a chance to work on my makeup technique and learn how to pick outfits for different occasions. Dinner, sleepwear, and sometimes something special to impress a guy. I must admit, the more I practiced, the more and more my memory of what I looked like as a hairy masculine male, was fading. Little did I know however, today would be the day that truly changed me forever.

David came in and woke us up. He asked Sherry to leave and go to the den to watch tv. After Sherry was gone, he looked me up in down with a sinister look. I was freaking out, I thought I was in trouble for something. He began grabbing my cheeks tightly and feeling me up with his other hand. Slowly his hand worked its way under my panties and between my crack. He was checking to make sure I was plugged up. "Good girl," he said. "Getting that pussy all ready for daddy are we?"

"Yes daddy," I reply as my face turns red.

"Good, cause we need to talk... Tonight you will have officially been here a week with us. You've come a long way in such little time. However, I'm hosting an event here this Saturday as I'm sure you are aware. There's going to be a lot of horny men, and a lot of sissies like yourself. Each of you will be assigned specific tasks to keep these men happy, but I still don't quite know where I should put you for your first time. I also however, need to see how well you can handle taking a big dick inside you. So since tonight is a special occasion, I've decided there's no better opportunity than to take your virginity and fuck every last bit of masculinity you have stored in that confused head of yours, sound good?"

His tone was stern, and left me stuttering, "y..yes daddy."

"You don't sound too enthusiastic about it now. Maybe you need a little reminder of your first night here? Because make no mistake, I may be a busy man, but I will always find time to yank this belt off and teach a little brat like you a lesson. Now do you wanna try that again?"

"Sorry daddy, please, I want you to take my virginity, please. I want to feel you inside of me, please."

His tone softens again. "That's a little better, but I want you to understand something. You get yourself ready. Make sure you're perfectly clean and put on something nice. Show me how much you want it, and depending on how well you do. I might just be gentle with you for your first time. Don't impress me at all, and I promise you won't sit right for a month, understood?"

"Yes daddy, I'll dress up very sexy for you tonight."

"Perfect. Madam Victoria will bring you up to me at five o'clock on the dot, be ready." He smacks me on the ass and walks out of the room.

The day couldn't have come faster, I was freaked out, but soon, Sherry returned. I told her the situation and she immediately started working on getting me ready.

We looked through all the possible outfits. We decided on a matching pair of Panties and bra. They were soft satin purple with a floral pattern and ruffles on the sides. They were full back with one exception, there was a wide opening giving access to the ass. Almost like crotchless panties, but these were assless. The bra fit perfectly, and we stuffed it with gel padding to look like I had a solid set of breasts. To top it off, the panties had four garter straps. We found a nice matching pair of purple seamed stockings to attach as well. The icing on the cake though, was the elegant black dress that sparkled with silver and purple accents. To match the black. Then a highly arched pair of stilettos which I practiced walking in for awhile, to get my strut looking suggestive.

We spent forever on my make up, changing the contour and finding the right shade of lipstick that wouldn't rub off quickly. We even decided to pierce my ears. Surely that would show him my commitment.

We had about an hour to kill until it was time. I made sure my hole was perfectly clean all the way through, and lubed up well. After that, we sat and talked to keep me calm until Victoria came in.

About ten minutes before five, Victoria opens the cell and signals for me to follow. I walk slowly, working on my stride, then we work are way up to his bedroom.

"You look very pretty tonight Tricia," she says as we make are way up the second set of stairs. We stop at the bedroom door. "Here's where I leave you, just knock on the door, and wait till you are called in."

"Yes Ma'am," I respond. Then she turns around and walks back down the stairs. I pause facing the door, and take a deep breath, then lightly, I knock.

"Who is it?" I hear him ask from within the room.

"It's me, Tricia," I reply.

"Come on in Tricia, I'm in the walk-in closet."

I slowly open the door, then put on my sexiest walk as I approach the closet. He's sitting on the bench in the closet, in a full suit, taking off his tie and shoes. "Hello Daddy," I say as he makes eye contact with me.

"Well look at you, Tricia," he says. "Looks like someone spent a long time getting ready tonight. I think you're really looking forward to this, huh?"

"Yes Daddy, I am."

"Good, and I can see from the camera footage you've been practicing quite a bit. Have you been thinking about Daddy's cock inside you a lot?"

"Yes Daddy, I have"

"I bet you have you little slut. Now why don't you do a little spin so I can see what I'm working with."

I spin around slowly, sticking my breasts forward and my ass out to make me look as shapely as possible.

"Very nice Tricia. You should always want to look good for your daddy. You could work on those butt cheeks a little though. Have Sherry show you some squats. That'll help give you more of a desirable figure. For now though, why don't you come over here and help daddy get out of his work clothes."

"Yes Daddy," I respond as I walk over to him at the bench. I help him take off his jacket, and hang it up. Then I come back and drop to my knees. I reach up to his collar and unbutton his shirt. Staring directly at his hairy, muscular chest. Then I unbutton his pants. After I get the zipper loose. He grabs the back of my head pushing my face towards his crotch. I knew just what he was signaling me to do. So I rest my mouth on his bulge and begin fiddling my hands through the side of his underwear. I rub my face side to side then get a good grip on his shaft and pull it out through the side.

I watch as he slowly becomes erect. With my left hand fondling his balls, I begin kissing it softly. Occasionally he would hold my head back and slap me in the face with it, getting little drops of pre cum on my makeup.

Eventually, he aims the tip at my lips. "You know what that thick purple lipstick tells me?" He asks, and then I look up at him. " It says you like sucking cock. It's like a sign on your face that reads, insert dick here." He chuckles at his witty comment. "I mean that's why you wore it right?"

"Yes, of course Daddy," I reply.

"Well then, be a good whore and accept my offering."

I open wide and work his cock into my mouth. Keeping my lips pressed out to let him see my lipstick as it rubs up and down his thick shaft. This time however, I know there is no point in overworking myself as he clearly has no intention of cumming without fucking me first.

I work my mouth all over him for about fifteen minutes, and then he stops me. "I know you're not trying to make cum now and save your little pussy from what's coming are you?" He asks in a serious tone.

"No daddy," I reply as I look at him with concern.

"Good, because that ass is mine tonight. In fact, I think it's about time we get to it. Enough of this foreplay, I don't want you getting the wrong idea and think that this is something special. You're just another little cock hungry whore to me, and nothing more. It's time you make good on your promise and show me just how much of a sissy you really are. Now finish taking my pants off."

"Yes Daddy," I quickly reply. His voice was so demeaning and I started to tear up a little. I was hoping he would be calm and take it easy, but I could see he wasn't fooling around. I pull his pants all the way off. He yanks them from my hands and throws them on the bench next to him as he stands up.

He reaches down and pulls me up from under my armpit. "Up you go now, get over there and stand in front of my bed.

I quickly march forward almost tripping on my heels. I stop at the foot of the bed and wait as he follows behind and takes a seat on the edge of the bed.

"Alright whore, I know you didn't get all dressed up just to keep those clothes on all night. Strip for me. Wiggle that ass and slide that dress up off you.

I turn and aim my ass in his direction, my eyes watering and beginning to tear. I tried my hardest to dance a little girly and shake my ass around. I slowly lifted the bottom of my dress up to my butt cheeks, and held it tightly as it went up to my hips, revealing my garter and panties.

"Wow, look at that little sissy ass in those panties. You are such a whore, wearing those open back panties giving me access. You want to keep those on while I fuck you, don't you.

"I do daddy," I reply as I pull the dress completely off, and drop it to the floor.

"Why don't you drop down and give daddy a little lap dance. Let me see you work that ass."

I lower my butt onto his bulge. Half of him is still in his underwear, but the head is poking out the side. I move my ass back and forth on him as he hardens up once more. I hold on tightly to his knees and lean my head back onto his chest. He takes his hands and cups my breast around my bra.

"That's it Tricia, show Daddy just how much you want this dick inside you," he orders softly in my ear. "Now I want you to understand something."

"Yes Daddy?" I ask.

"Tonight, I'm gonna take your virginity from you. Now once you get a real man's cock deep in that tight little virgin hole of yours, do you know what that means?"

"What does it mean, Daddy?"

"It means there's no going back. You will forever and always be a sissy. Whether you enjoy it or not, you will never get your manhood back no matter how hard you try. So I have to ask, are you ready to officially become the person you were truly meant to be?"

I was so frightened and taken back by his words. No way was this really going to make me feel any different... I respond though, "yes Daddy, I'm ready to become an official sissy."

"I'm glad you're ready, not that you have a choice, because that ass belongs to me either way. Now lay down on the bed and pull your legs up over your head. Present that tight little asspussy to me," he demanded as he pushed me up off of him, rolling me onto the bed laying on my back.

I pulled my legs up just like I did with Sherry, but this was so much scarier. I was almost as scared as the last time I was in his room. Just being in their was making me flashback on that brutal spanking he gave me the night that I showed up. I began to cry.

"Aww," he says in a condescending tone. "Don't worry, you don't have to enjoy it, you just have to accept it. I could care less if it feels good for you, and you shouldn't care either. Remember, your only concern should be pleasing me. So cry all you want, just keep those legs spread open and do your job, because that's what a good whore does."

I spread my legs wide for him, leaving my hole well exposed. He takes his underwear off and strokes his cock, paying attention to nothing but my body. Then, he leans forward grabs my legs, pulling my entire body to the very edge of the bed, and it begins.

He first works his penis in between my cheeks rubbing the tip up and down on my anal bud. Eventually, he starts easing the tip past the opening. Thankfully he wasn't being too aggressive with it.

Little by little, stroke by stroke he eases his way into me. He was much thicker than any of the dildos that Sherry and I had played with, but so much more natural feeling. Every time I thought he was all the way in though, it just kept going. He was most certainly harder than usual.

He started poking my prostate, and each time I moaned in a strange sense of both agony and relief. Once he was all the way in, he began to pump back and forth. I remained as relaxed as possible, just like Sherry had taught me. The more and more I relaxed, the easier it was to take it.

He started to make degrading comments about my uncontrollable moaning. "That's right, you know you like it. You know this is what you were meant for. Just lay there and take it, because there's no going back now. I told you little girl, once you get this cock inside you, you're a sissy for life. Your tiny little clit will never see the inside of a pussy again. So you better start learning to enjoy good dick, because that's all you're getting for the rest of your life."

As his words became more vulgar, he started pumping harder and harder. His cock was jammed so far up my ass it was unbearable. At the same time though, my mind was becoming blissful. I was becoming numb, as if he was fucking all of the free will away from my soul. To be honest though, the more it happened, the more I accepted what was happening.

He calls me out, on what I was feeling. "You like that don't you?"

"Yes Daddy, it feels good."

"Good, don't fight it, focus on my cock stretching your tight little boipussy. Think about how natural it feels to be fucked by your alpha male."

All of the sudden, he pulls out. Then he grabs me by the hips and flips me over. "Up on all fours," he demands. "Get your ass up and your face down.

"Yes Daddy," I do as I'm told and get in doggystyle position.

"Now arch that back and show me that pussy."

Luckily my back had pretty much healed from the soreness of the day they had me locked in the dog cage, and arching it became easier.

He pushes his cock back in me as he pulls me in tightly by my pelvis. "That's it, keep that ass up so I can fuck you nice and deep."

We remained in that position for about another twenty minutes. I was becoming sore and I didn't know how much longer I could handle it. I felt like I was going to pass out.

He starts to interrogate me. "Are you gonna be a good little whore from now on?"

"Yes, Daddy, I promise."

"Are you done thinking about pussy?"

"Yes Daddy, I'll never think about it again, I swear."

"That's right. Now are you ready to be daddy's property, and do exactly as I say, and accept the consequences when you don't?"

"Yes Daddy!" I moan out as he holds his cock deep inside.

"Good, cause here's what's gonna happen. I'm gonna cum deep in that ass. That's right, and you're gonna hold in every last drop. I don't want to see a single drop leek out, understand?"

"Yes Daddy, I won't let a single drop go."

"Good, because I'm about to impregnate you. I'm gonna fill that belly full of seimen and do you know what happens when a sissy gets pregnant?"

"No Daddy, I don't"

"They become loyal little sluts. Why? Because once a mans cum gets in their belly, they become addicted. They need cum to survive so they'll do whatever it takes to get a fix. Whenever a cock is presented to them, they can't say no. They take it in either hole and don't stop till they get what they need, and each time they become more and more addicted. So tonight, I'm going to plant that seed inside you. Now get ready, because this is it. No turning back now."

His words were frightening. I figured he was just talking crazy though. There's no way I could become addicted to cum... right? He was certainly digging at my insecurities.

He starts pounding me harder and harder. I start to scream out in pain "oh fuck!" Then he slaps me hard on my ass, "ahhhh!" I scream

"Beg for it!" He shouts

I cry out, "please cum daddy, I want your cum inside me, I want to become pregnant with your seed."

He starts moaning heavily, "here it comes skank, here comes your new destiny!"

He jams his cock up into me so far I felt like he hit my intestines. I cry out as he starts to squirt. I can feel each shot filling me deep inside. It lasted forever, but slowly he retracted and inched his way out.

Once the tip was out he pressed his finger on my anal bud. "Hold it in slut! Take all of it."

I clenched my butt together as hard as I could. Eventually the temptation to release dies down and I could feel his cum working it's way up into my stomach. I had a mix of feelings. It felt so strange, but at the same time I was relieved that he was done.

He steps over to his dresser drawer and grabs something. I start to feel something entering my ass once more, but it wasn't his penis, It was a plug. "There we go," he said after it slid all the way up. "That'll help keep it in there with no accidents. Now turn around and clean my dick off."

I turn and face him on all fours as he stands by the edge. With his cock in my face, I can smell a mix of my ass and his remaining cum. I try not to gag as I open up to suck everything. He was soft after cumming though, so that was a nice change.

"Alright Tricia, we're done here. Put your dress back on and go to your room. Keep that plug in for at least two hours. I'll give your ass a little break tonight, so you can take it out before you go to bed. Also, I want you to lay on your sides so it came make its way up to your stomach, Okay?"

"Yes Daddy, thank you Daddy." I hop off the bed and pick up my dress. After I wiggle it back on, I take my walk of shame back down to the basement. With my ass feeling stretched out and my tummy bloated from the massive load that was inside me.

When I reached the den, Sherry and Victoria were sitting and watching TV. I walked past them as I couldn't bare to talk to anyone. Plus, he had told me to head straight to my room. I head into the cell and lay on my side for the rest of the night. Thinking hard about what I had gotten myself into. I had become submissive to this man, and felt as though I would never go home, because now that my virginity was his, I was actually his property to do with as he pleases. He was the alpha, and I was his beta bitch. I had become exactly what he told me I was from the beginning. Nothing more than a useless, sissy whore.

The End...