Living in the projects of Chicago is exactly how it sounds. A nightmare. To make matters worse, my mom’s usually fucked up on whatever drug she can find half the time, doing some unsavory things in order to maintain her fix.
We’ve all had to do things we’re not proud of to survive in this hell hole, myself included. Being a small, pale skin, “sissy” white boy in a place like this has made me an easy target. Especially without a dad to protect me, he left a long time ago.
It’s bad enough that I’m constantly confused for a girl, but being the son of a whore doesn’t make matters any better. Don’t get me wrong, I love my mother, but she’s hard to be with. Constantly degrading me and always fucked up. Bringing home assholes who treat us like shit.
Some of them would have easily had their way with me if it wasn’t for the deal I made with Nekeisha. I know many of them would have forced themselves on me. Nekeisha isn't someone you want to mess with. She’s runs everything around here.
Drugs, guns, hookers, you want it she’s got the hookup. She can even have someone killed off for the right price. Everyone fears her. Maybe the fact that she’s got a bigger dick than most men might also have something to do with it.
All I know is that I’m under her protection as long as I keep up my end of the deal.
It can be a bit degrading, doing the things she wants me to do, but it keeps me safe from everyone else.
As I put on the white cotton panties she likes so much, it’s not really all that hard to rationalize it. What’s a couple of degrading acts if it’s what keeps me from the other animals that would do far worse.
Besides, Nekeisha quite fearsome and ruthless most of the time. I’ve experienced my fair share of her to know how cruel she can be. I used to be so scared of her.
I slide on the white stockings over my freshly shaved legs and put on the short skirt she gave me. After I put on a training bra and button up the white shirt, leaving the midriff bare, I start putting on makeup.
After I’ve applied the lip gloss, blush, and some eye shadow, I hardly recognize the beautiful girl in the mirror. Her golden blonde hair is tied up in a ponytail with blue eyes full of despair.
“Going to whore yourself out again?” my mother asks as I walk out of the bathroom in my heels. “You’re pathetic, you fucking sissy.”
Her words sting, but I’ve grown used to them.
I don’t even give her a reply as I grab my bag and leave. I make my way up to the top floor, getting the wrong kind of attention from every guy I pass. I hear a slew of catcalls, solicitations and endure few attempted gropings.
Eventually, I get to room 1612, Nekeisha’s room. There are two big black men outside guarding her apartment.
One of them knocks on the door. A giant black man with arms bigger than my body answers it and takes one glance at me. “Nekeisha, your whore’s here.”
“Well, let her in. I need my dick sucked.”
He moves out of the way and lets me through. Nekeisha’s sitting on the couch with a joint in her hands. Her hair is done up in braids. She’s got a mean look on her face. Even though her face is always in a scowl, she’s still very beautiful, in a rugged kind of way. She motions me to get on my knees in front of her as she takes a puff. I can tell the air is thick with tension.
Obediently, I do as I’m told, walking over to her and dropping to my knees. Without another word, I fish out her big black 8-inch flaccid cock and give it a kiss. “That’s it slut, get to work.”
I slide her thick head between my lips, it’s almost too big to fit. I have to strain my jaw open to get it in.
She pushes my head down, forcing more of her cock in my mouth. “Swallow it, bitch. I want my dick down your throat.”
I take down a big gulp and her shaft sinks down my throat, clogging up my windpipe. She starts thrusting, giving my face a good fuck. I can feel everyone watching me as she thrusts her fat anaconda all the way down my throat. My nose meets her pubes. The musky scent of her sweaty crotch fills my nostrils.
“That bitch is a natural cocksucker,” one of the guys sitting at the table across the room says.
“What’s the word on that shipment of AKs?” Nekeisha asks as she grabs my ponytail and starts pumping my head up and down on her dick.
“We’ll get them to the buyer and get our cash before the end of the night,” another man sitting at the table quickly says.
“You fucking better! If I don’t get my money, someone’s gonna fucking die.”
“Don’t worry, Nekeisha, we’ll get that paper,” Jerome says.
“And what about the coke? Have we sold through our remaining inventory?” she asks.
“We’ve got a little bit left, but we’ll get the rest out.”
“It better be replaced with paper by the end of the night,” she growls.
“It will,” says the guy at the table.
“So, when will we get to take a turn on that sissy’s bubble butt?” he asks. I quickly look up at Nekeisha, pleading with my eyes. Please don’t let them touch me.
“Touch my bitch and I’ll paint my walls with your brains. Now, everybody out. I’m going to fuck her tight ass and hit the sheets. It’s been a long fucking day…”
Everyone leaves but Jerome, he’s Nekeisha’s right-hand man. She pulls her cock out of my mouth. “Come on, baby. Let’s go to my bed and continue where we left off.”
She grabs my hand and leads me into her bedroom. Once we’re behind closed doors, she pulls me into a deep passionate kiss. Her tongue explores my mouth as her hand reaches up underneath my skirt and grabs a handful of my ass. When we’re in private, she shows me her softer side. A side I desperately want more of.
“None of those motherfuckers hurt you, did they?” she asks as she places her hand on my cheek, stroking it with her thumb while she looks deep into my eyes. “I swear, if anyone even so much as lays a finger on you I will kill them.”
I smile at her. “No… no one has hurt me.”
Once again her lips are on mine. She pulls down my skirt and moves her hand up to my shirt, slowly unbuttoning it while her tongue wrestles with mine. After she gets my shirt off, she takes off her own shirt, revealing a set of breasts the shape of giant grapefruits with a set of rock hard abs underneath. Her right arm is covered in tattoos. She pulls down her baggy tattered jeans. Then she pulls off her spandex briefs. Her monster of a python dangles free down between her legs.
I barely get enough time to take her all in before she picks me up and lays me down on the bed, flat on my stomach.
Ever so slowly, she pulls down my panties, leaving my ass bare. She gives it a hard slap, before diving in. The feel of her tongue sends a shiver down my spine.
As she spreads my cheeks open, as she licks up and down the crack of my ass before pushing past my sphincter. I moan out from the sensation caused by her tongue.
“Alright, baby. Mama’s coming in.”
She scoots up and straddles my thighs. I can feel the head of her cock nudge up between my ass cheeks as she leans over and grabs the bottle of lube on the bedside table.
She squirts a big glob of it and smears it all over my tight little butthole and then she lathers her cock up with it.
Before I know it, her monster of a dick is knocking at my back door. I try my best to relax as she pops the head into my rectum. It hurts as it spreads my fuck hole wide open, but not as much as it used to.
She slowly sinks her dick deeper inside me. I grip the sheets and bite into the pillow, anything to help with the pain. “Breathe, baby. Breathe.” She leans down and kisses my shoulder as she wraps her arm around my neck, forcing my face up to hers. “Just relax and let Mamma in.”
I try to fill my lungs with air, but the dick lodging itself in my ass makes me grit my teeth.
She pulls out just a little before she pushes back in deeper. Little by little, she forces her cock deeper inside my ass. Gradually, pushing more and more of her log inside me. She gyrates her hips, spreading my butt open even more as she lays kisses on my cheek. Her hand traces down my arm and over my clenched fist full of sheets. I release the fabric as she locks her fingers in with mine.
That fat cock of hers rubs up against that sensitive spot inside my ass, forcing a moan to escape my lips. She calls it my g-spot. “That it baby. Moan for me.”
She continues to sink her dick inside me until I can feel her balls rest against mine. “There, the worst part is over, baby. I’m balls deep inside your ass.”
She lets my ass adjust to her big black dick before she gradually starts to thrust in and out.
“Urgh… Uuuuh. Awww!” Every jab of her dick sends ripples of pain mix with pleasure through my body as I moan groan and grunt with each and every thrust.
“That’s it, just take Mama's cock. You’re safe here with me, I’ll protect you. Just as long as you’re mine,” she whispers in my ear as she slowly fucks me, filling me up with her big black dick.
“Oooh, fuck… I’m always going to be yours, Mama…” I gasp as she pushes all the way inside me. My own little cock is hard. Every thrust of her hips pushes my little pecker up against the sheets.
Her pace picks up as she starts to truly fuck me. The way she slams her dick inside me makes my whole body quake.
That fuckstick of hers fills me up with every stab. It’s like having a tree trunk shoved up my ass. But the pain has all but subsided and I’m overtaken with the pleasure of that fat cock as she pummels my g-spot.
“Urh, please mamma! Make me yours! Take my ass” I moan out, completely lost in her arms as she batters my ass, plunging her cock deep down inside me.
“That’s it, baby, surrender to me.” Her speed increases as she starts to give me a real good dicking. My mind goes blank from sensory overload as she fucks me good. That dick makes me moan like a bitch each time it batters my g-spot. I’m her bitch.
My own little pecker is leaking out cum as the pleasure erupts through me. Suddenly she hilts herself all the way inside me. A hot steamy liquid erupts from her cock, filling me up. It feels so good. Slowly she starts gyrating her hips, trying to deposit all of her seed inside me.
I push my ass back into her. I want all of her cum inside me. I desperately want to be her good girl.
“Fuck! That was… Fucking amazing,” She moans as she pulls out of my ass with a pop and rolls over onto her back. “Come here and clean my dick off, baby.”
I struggle to get to my knees, I’m always weak after being fucked by her monster cock. Laying down, I slink my leg over hers as start licking her dirty cum covered dick clean. I can still taste the stench of my own ass on her pole, but I love her thick creamy cum. I would do anything for her.
It wasn’t always like this. When she first took me up to her room, she degraded and humiliated me. Forced me to become her sissy bitch. But I’ve learned that she has to put out a hard front. To maintain her power, she’s got to make people fear her. So she plays the role of a ruthless killer.
But I’ve never felt safer when I’m with her. I look up into those dark brown eyes of hers as my tongue works up and down her cock, licking up every last bit of her cum.
“Can I please stay with you? I don’t want to go back home.” The thought of going back to my abusive mother all drugged up being plowed by some asshole makes me want to cry.
Her hand grabs my chin and pulls me up to her. “Baby, you can make this bed your home, but you know my rules. If you’re going to stay with me, I want you all pretty. I want you to give up any notion of being a boy. You gotta be my girl from now on. Is that what you want?”
“Mama, I love you. If being pretty and becoming your girl is all that I have to do to be with you, then I’ll never be a boy again. I just want to stay in your arms.”
She brings me in for a deeply intimate kiss. I didn’t know I could ever feel this way, but being with her feels right. I was scared at first. She can be so intimidating around other people. And she was so aggressive at first. And the first time we had sex, it hurt… A lot, but it also felt good. And she couldn’t get enough. But we bonded. Neither of us ever expected it, but it happened. Now, there’s no place I’d rather be than wrapped up in her arms.
She rests my head against her breasts as she runs her hand through my hair, undoing my ponytail.
“I’d never imagined that I’d be falling in love with a little sissy, but, I am with you, Sarah,” she whispers. Sarah’s the name she gave me when she started forcing me into girl clothing. It used to make me feel so ashamed, but now… I love it. The name I had before, Jeff… It’s no longer mine.
I’m mama’s girl and my name is Sarah.
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