Chapter 5: Daniel Martin

What should I do? 

I’m laying here naked in the arms of Jacob after he just fucked my ass and now he’s asking me if I want to embrace being his sissy. I can’t deny how amazing it felt to get my ass fucked. It hurt a bit at first, but I never imagined having another man’s cock in my ass would feel like that. Although, it’s becoming harder and harder to call myself a man as I lay here naked, with my head on Jacob’s chest wrapped in his arms with my ass plugged full of cum. I certainly don’t feel like a man right now. 

I meet his gaze as he waits for my answer. I have a deep-seated feeling in my gut telling me that I truly am a sissy and I should accept. But what would people at school say? Especially Bret. Of course, Jacob said he wouldn’t let anyone hurt me if I became his sissy. He said he’d protect me. But what about my mom? What would she think? 

He raises an eyebrow, waiting for me to reply. I’ll admit that I do like how it feels to have his arms wrapped around me. 

I should do it, but the thought of going to school dressed as a girl makes me feel sick in my stomach. Before I can answer, the door snaps open. My heart bangs against my rib cage, attempting to break out of my chest as Tanesha walks in, Jacob’s fraternal twin sister. She’s one of the hottest girls in school with thick wide hips and a bubble butt. Her skin is smooth as silk and dark as umber. 

She has a devilish smirk on her lips. “I knew it. You popped his little boi pussy, didn’t you?” she asks, placing a hand on her hip and raising an eyebrow. 

Jacob only smirks. “Obviously.”

“Damn, lucky bastard. Well, should I start teaching the sissy how to dress properly, put on makeup, and do her hair?” Tanesha asks as her eyes drift down my body and she licks her lips while I try and fail at covering myself up. 

Jacob shrugs once again. “I’m still waiting for her response. I just asked if she wants to fully accept and embrace being my sissy.” 

“Woah, hold up, can she truly make a well-informed decision without experiencing what it’s like to dress like a sissy?” she asks with an impish smirk forming on her beautiful lips. 

Jacob lets out a chuckle. “You’re right, I guess not.”

Tanesha grabs me with surprising strength, pulls me out of bed, and leads me into the bathroom. Before I know it, what little body hair I have is being lasered off. Then she drags me into the bathtub, scrubs me down with the shower hose extension along with one of those scrubby things, and a whole lot of girly fruity smelling body wash before shampooing and conditioning my hair. After she rinses me off, she rubs me dry with a towel and drags me into her room. It’s your typical girl’s room with light pink walls, fluffy white carpet, and a large bed with a lot of pillows. 

She rummages through her closet before pulling out some clothes. With a push, I fall back onto her bed. I don’t even realize what she’s doing before she puts some kind of device on my cock. It’s a pink little cage and she attaches a padlock to it. She gives me a wicked smile. “My brother really likes you and I think you’re cute as well. Jacob might be willing to give you a choice in being a sissy, but I’m not. Here’s the deal, you’re our sissy from now on whether you like it or not unless you never want your little cock unlocked. One thing you’ll learn about us is that we always get what we want. Now, stop being a tease and accept the fact that you’re our bitch.” 

I don’t even know what to say as she slides a pair of pink lacy panties up my thighs before making me scooch my butt up to cover it in what’s actually a thong. The thin strip of lace wedges deep between my asscheeks. “Look, don’t get worked up over it. It’s not personal. It’s not like I mean any harm or malice. My brother and I are super close and we not only share similar tastes but almost everything else. You’re in good hands with us.” 

She slides up white-thigh high stockings up to my thighs. “So be a good little sissy and submit yourself to be our bitch. Because we all know you little white boys need big black cocks to worship.”

I’ve never felt so emasculated. I can’t even meet her eyes. She then has me stand up before putting a training bra on me and sliding a thin, tight pink dress over my head. The thing barely covers my ass and you can see the tops of the thigh-high stockings. She has me sit back down and then attaches a collar around my neck with a leash attached. I look down to see a tag on it. “Do you know what that says?”

I can barely make out the upside-down words, but Tanesha doesn’t wait for me to answer. “Sissy bitch, because that’s what you are. I’ve actually been saving this for you because it was only a matter of time before we’d make you our sissy bitch.” 

She starts to apply makeup to my face. I couldn’t even tell you what she does, but soon she’s doing up my hair. “There, all done. Now you look like a proper sissy. Let’s go show off to your daddy.”

She grabs the leash and gives it a jerk, forcing me to stand up as my heart races and I feel such deep humiliation. She leads me out of her room and into Jacob’s. His eyes go wide. “Damn, I thought you were sexy, but fuck me. You look like a goddamn model.”

“I told you I’d have him looking fine,” Tanesha says with a smirk, then her eyes glide over to me. “Now it’s time for my payment.” 

I look at her, wide-eyed. What does she mean by that? Jacob only shrugs. Tanesha then plops her big perfect tush into Jacob’s computer chair, pulls up her skirt, slides her panties out of the way, and my jaw drops as a large black cock flops out. She has a dick and it’s bigger than mine!

“Come on sissy, let’s see those pretty painted lips get to work on my dick,” she says with a grin. 

I hesitate, completely caught off guard by this new revelation. A snap of Tanesha’s fingers brings me out of my shock and without thinking, I drop to my knees and crawl up between Tanesha’s legs before taking that big thick black cock into my mouth and getting to work. It’s not as thick or as long as Jacob’s, but it’s still pretty big and I have to keep my lips over my teeth to keep from scraping against her cock. 

She runs her hand through my hair as I slowly take more and more of her dick in my mouth before sliding back up and twirling my tongue around the tip. She gives out a soft moan. “Fuck, this little white sissy sure knows how to suck dick.” 

“Fucking natural, isn’t she?” Jacob asks. 

“You got that right,” Tanesha says as she urges my head back down her shaft. 

I start bobbing up and down her dark black dick as her hand which has a firm grip on my hair guides my motions. Her other hand grips the base of her dick before she pulls it out of my mouth and slaps it against my lips. 

I’m tugged back down as she thrusts her big fat cock straight to the entrance of my throat, making me gag in surprise. “There are still some things we can work on.” 

She starts thrusting her hips, fucking my mouth as spit drools down her shaft, connecting strings to my chin. She slowly pushes her dick against the entrance of my throat, unrelenting. Finally, with a pop, it forces its way down my throat, clogging up my windpipe. I latch onto her thighs as my nose smashes into her pelvis while her balls rest against my chin. Her cock is fully lodged down my throat and she gives out a guttural moan. “Fuck, that’s so tight.”

Finally, after I struggle to breathe, she lets up and her dick slips from my mouth entirely, allowing me to breathe. She still has a firm grip on my hair as she smacks her dick against my cheek. “We’re going to have so much fun with this little sissy.”

“Don’t get too carried away, I like her,” Jacob says as he rests on the bed, watching.

Tanesha only shrugs as she pulls my mouth back onto her cock and starts pumping my head up and down on her shaft. I try my best to breathe and suck as I’m bounced up and down her cock like a basketball. 

She then sinks her cock back down my throat and stands up with her dick still lodged all the way down my windpipe. She starts to fuck my throat, ramming deep and quickly. Her balls smack against my chin with each thrust as spit drools down, dripping onto my chest. “Oh fuck, here it comes, bitch.” 

She pulls out, leaving the tip as she furiously strokes her cock. My eyes go wide as my mouth is filled with cum. I try to swallow, I’m filled up with another load before she pulls out and covers my face with her spunk. “Fuck, that felt so fucking good. What a cocksucker you are. Guess what, tomorrow, after school, you’re coming here and I’ll get you ready for the party after the big game. We’ll go to the game together and no one will recognize you because you’ll be the second hottest girl there. Next to me of course. Got it?” 

I nod as I lick the cum off my lips. “Good girl. Then at the party, you’ll be our little cock slut.”

“Well, she means you’ll be my little girlfriend. At least to everyone there, but in private you’ll be our cock slut,” Jacob says as he gets up. “Now you can leave, Tanesha, Danielle, and I have actual homework to do. I wasn’t lying about that when I first got you over here. I still need to maintain my GPA and now that I’ve got the only person who’s got a better GPA than me, I might as well get some work done. Especially with that Calc exam coming up. I need at least 96% to maintain an A and keep myself with the second-highest GPA score. But let’s be real, I’m shooting for a hundred and I will be number one. There’s no reason I shouldn’t get it, we’re just dealing with derivatives. This is easy shit, am I right?” 

He turns to me with a grin. “Although, I do find it sexy that my only true competition is my little sissy girlfriend. Really makes me want to fuck you.” 

Tanesha sighs and pulls up her panties before she walks out. “Fucking nerds.” 

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I posted about it on my social media accounts, but no one cares. As I search the internet for something, anything, I get a message from one of the social apps I used for gaming. 

“I read about your situation and I can offer you a solution,” Masterdom says. 

I click his profile, and a brute of a man greets me. He’s ripped like a bodybuilder. I pull up a shirtless pick and he’s got several tattoos up his arms and one across his rock-hard abs. He’s got a rough 5 o’clock shadow with short, dark brown hair. A lot of his pictures are of him with other men. There are a few pictures with several cute girls, but mostly other guys. Some with a few guys and a girl. He showed a snap of a room that looked like a dungeon. What the hell could this guy possibly want? 

“What’s that?” I reply. 

“I’m looking for a new submissive slave. I’ll give you a place to sleep, 3 meals a day, and pretty much anything you want. But you’ll be mine as long as you stay here and service me sexually, doing anything I want.”

Wow… Should’ve figured. I’ll pass. Although, I should hear him out. It’s not like I have any other options. “And what would I have to do as your slave?”

“You’d be servicing my cock of course. Sometimes you’d be tied up, sometimes not. You’d always have a collar on to mark that you’re mine. And of course, I’d decide what else you’d wear. I can promise you, I’m not into pain or anything. Just need a good cocksucker who can take a few dicks. Of course, after I’ll train you properly, I might let my friends get a turn.” 

I shiver goes down my spine as I imagine a life like that. “Umm. Thanks, but no thanks. I’m not gay.” 

I continue to search, online but he messages me back.

“Suit yourself. When you change your mind. Here’s my address.” He sends me an address to his place. Yeah, not likely. 

I spend hours at the library, searching for someplace to stay. Anything. But I come up short. This can’t be happening. How is it the only offer I got is from a gay guy trying to turn me into his fuck toy? 

As the library goes to close. I find myself in a desperate situation. I’ve got nothing. No place to go, no home to sleep in. Nothing. 

—

I can’t believe I’m doing this, but what other options do I have? God… I’m so nervous. My heart is beating so fast, I feel as if it’s having palpitations as I find myself walking up to a rather large apartment building. I slip inside as someone walks out. As I walk up to his apartment, my mind runs wild with all the gay things he’d do to me. I’ve never even touched another man’s cock let alone sucked one. I’m not even going to think about taking one up my ass. 

I can’t do this, I turn around and go to walk out. But where else can I go? I have no other place…

Fuck! Life is not fair. Shit, what should I do? Find an underpass to sleep under? I can’t do that. I don’t think I can suck a cock either. Shit… Shit, shit… Shit!

God. There’s really no other choice, is there? I find myself turned around and in the elevator, heading up. My hands are sweating profusely. As I reach his floor, I mindlessly walk to his door. Moment of truth. If I knock on his door, there’s probably no turning back. 

Spend the foreseeable future sucking this guy’s cock or sleep under an underpass with a bunch of crackheads? I’ll probably end up being forced to suck cock there too. There’s no good outcome here. 

My knuckles bang against the door. It feels like forever, standing there waiting for him to answer. I can feel my stomach tie itself into knots. The sound of the locks coming undone makes the hair on the back of my neck stand up and sends goosebumps all along my skin. 

Suddenly, I’m greeted by the hulk of a man in nothing but a towel. A devious smirk on his face. “Can’t say I’m surprised.” 

He looks down the hall in both directions before pulling me inside. 

“I… I just wanted to talk and check things out,” I say, my voice trembling. 

“Is that so?” he asks as I follow him into his luxurious apartment. It’s got an overhanging loft with wood flooring and art hanging up all over. “I think you just ran out of options and now you’re getting desperate.” 

“I… I’ve got some questions,” I spit out. 

“Shoot away,” he says. 

“Can I leave at any time?” I ask. 

“No. Once you’re my slave, you’re mine,” he says. 

“What? Wait… Seriously?” I ask.

“Of course. If you decide to be my slave, you’re mine. No if, ands, or buts about it. Well, just yours.” A sly grin curls on his face. 

“I… I don’t think I can do this,” I say. 

“Now, come on. Tell me what you’re afraid of,” he says. 

“I’m not gay,” I say. 

“You will be a cock hungry slut when I’m done with you. Trust me, one day with me and you’ll be begging me for more dick.” His eyes travel up and down me, making my knees weak.

“Where will I sleep?” I ask. 

“In my bed. With me,” he says. 

“What…”

“No more questions. Decide now. You can either take off your clothes and submit to me or leave.” 

Shit. What should I do? What choice do I have? Either submit to this guy and end up as his slave or take my chances on the streets… Fuck, that’s not much of a decision. I can’t do this. And yet, I find myself dropping my duffle bag and taking off my clothes. 

“Good choice,” he says, as he slowly starts to circle me. “Naturally hairless, good. You’re quite girlish. I like that. I’m not surprised that you’ve got a tiny cock. Oh damn, that ass is a peach. You’ll make a nice sissy slut. We’ll have to grow that blonde hair out, but at least your skin can naturally tan.”

He runs a hand down my back. “And it’s smooth as silk. I’ve hit the lottery with you.” 

I shudder at his touch. “Now, let’s see how good you are a sucking cock.” 

He turns me around and shoves me down to my knees. Then he lets his towel fall to the ground and my eyes go wide. Dangling between his legs is the biggest cock I’ve ever seen, in real life including porn. That thing must be at least 7 inches flaccid. Fuck… This is like a nightmare I can’t wake up from and yet, I can’t take my eyes off it. 

He takes his massive cock in his grip as his other hand runs through my hair. Suddenly, he jerks me forward and rubs that python against my face. It feels so heavy. And it’s got such a strong musky scent. A scent that makes me convulse, but at the same time, my cock twitches. 

Before I can protest, he presses the tip of his still-soft cock up against my lips and it slips into my mouth. I’m shocked by a slap against the face. “No teeth.” 

I try my best to tuck my lips over them as he starts to thrust his cock in my mouth. God, I can’t believe I’m on my knees sucking dick right now. Never in my wildest dreams would I find myself blowing another guy. I feel so humiliated right now. He starts to swing his hips as his dick slowly gets harder and larger. I can feel it grow between my lips as it stretches out my jaw. Soon I’m choking on his cock. “Your cocksucking skills need some work, but I’ve got all the time in the world to train you.” 

His grip on my hair tightens as he pushes his cock up against my throat. I gag and revulse, drooling all over his dick as it runs down my chin. I fight back the urge to throw up. “Swallow it.” 

Tears fall from my eyes as I try to do what he says. Suddenly, as I swallow his fat cock as it pops down my throat. He continues to force all of it in as my nose meets his pelvis. I grip his legs, his thick powerful legs, desperately pushing myself away as I choke on his chode. Tears fall freely from my eyes as I gag. He finally lets me go and I collapse to the floor and cough up my lungs as spit drools down my chin. “Not bad for a first-timer.” 

He grabs me by the hair and forces his dick back in my mouth and fucks my face. Hard. I’m fighting back the urge to gag every time the head of his cock hits the entrance to my throat. I struggle to breathe with my mouth full of cock. Suddenly, he forces his cock back down my throat, clogging my windpipe. I choke and squirm as he moans out. My eyes go wide as I’m hit with a load of hot steamy liquid, erupting down my throat, straight into my stomach. He pulls out, leaving the tip still between my lips as he fills my mouth with a salty, sticky cream. I almost gag it up. “Swallow it.” 

It takes me everything I have to swallow his thick seed. He pulls out and paints my face with his jizz. “Good slave. Now clean my dick off.” 

I look up into those dark possessive eyes of his. So intimidating. I do what he says out of fear of punishment. I lean up and take his sticky cock into my hand and start to lick it clean. I take the flaccid tip into my mouth. The taste of his musky cream that’s still all over his dick. I slurp it up and clean his dick thoroughly. “Good slave. Looks like you enjoyed yourself.” 

His eyes drift down to my crotch. I look down to find my own little and inadequate pecker as hard as it can be, standing at attention. Humiliation washes over me and yet, I’m surprised to find myself so aroused. I lean up and take his cock back into my mouth, sucking and licking his dick clean. The taste isn’t as bad as I initially thought. I’m actually surprised to find that I’m not really all that disgusted by what I just did. I definitely feel degraded and humiliated, but that just makes me feel so hot inside, giving me this strange sense of euphoria. And the way he said good slave before ordering me around just sent shivers up my spine. 

He smirks as he pulls his cock out of my mouth and crotches down to cup my cum-covered face in his hands. “See? It won’t be so bad here. I won’t hurt you or anything. You’ll be safe with me. You’ll come to find that life as my sissy slave is pretty enjoyable. I’m not just a kinky dominant who enjoys humiliation and rough sex. I can be gentle, kind, compassionate, and romantic. I’ll indulge in your hobbies and fantasies, and even help you achieve your own goals and dreams as long as they don’t interfere with my own and, of course, only if you’re my slave.”

I swallow the leftover cum in my mouth and take a breath. “I guess that won’t be so bad.” 

His smile widens. “Oh just you wait, you will love it here. I think I finally found a perfect girlfriend.” 

I look up at him as I try to figure out what he just said. Girlfriend? “Of course, I’ve got a lot of work to do in training you. But I promise, if you be a good slave and do as I say, you’ll eventually get to see my compassionate side and you’ll love it. Now don’t let any of my cum on your face go to waste. Lick up every last drop.” 

What does he have planned for me? Compassionate side? I ponder this as I do what he says and take my hands to wipe the cum into my mouth and swallow it. The more I taste it, the more I like it. “Come slave, time to introduce you to your new life.” 

He picks me up into his big muscular arms as he takes me over to a room on the side. 

Inside is the room of the dungeon he posted about. He sets me down on the bed, pins me face down, and binds my hands behind my back before he walks over to a dresser. He comes back with a collar that says slave on it. He wraps it around my neck before attaching a leash to it. He then walks over to the closet and opens it up to reveal an assortment of girls’ clothing. What the fuck? 

“You never said anything about wearing girls’ clothing!” I say. 

“Don’t talk. Only speak when spoken to,” he says as he pulls out a pair of white cotton panties. 

“I… I’m not going to wear those,” I say. 

Wack! He smacks my ass so hard, the sting vibrates through my body, loosening tears from my eyes. Then he grabs a ball gag and jams it into my mouth, tightening it to the back of my head. Turning me on my back, he holds me down and slips the panties on me, and pulls me up to my feet. He makes me stand in front of the mirror. It’s so humiliating standing there in panties, hands bound behind my back, a collar wrapped around my neck with a leash attached to it, and a ball gag stuffed in my mouth. The worst part of it all, I look good in panties. I don’t even need makeup to look like a girl. And all the humiliation and domination keeps my little cock rock hard. It’s like my body wants to submit. But I feel so ashamed of it all. I break down and cry for the first time in a long time. 

He wraps his arms around me and brings his lips to my ear. The feel of his hot breath against my neck makes me shiver, but his rock-hard cock poking my back makes my knees buckle. “It’s okay to cry. I know this is going to be hard to accept at first, but your old life is over. You’re now my sissy slave and soon you’ll be my perfect little sissy wife. Once I train you and make you all prim and proper, you’ll be able to come out with me in public. My girlfriend at first, but soon you’ll become my little housewife. But we’ve got a lot of work to do until then.”

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