A Tale of Two Sissies Ch. 01

I feel butterflies in my tummy, but when Jarome steps forward, I obediently lie down.

I watch in fascinated dread, as Clayton pulls Vic's panties down. Just far enough to uncover the smaller teens ass. A cute ass all things considered. Feminine cute, though, not masculine.

One of the other boys hands their leader some lube, then they all begin to strip. Four strong naked black men. Standing over me and my best friend. Emasculated in our women's panties. Completely at their cruel mercy.

"Now you don't wanna make this harder than it has to be do you?" Clayton asks, straddling the sobbing boy's legs.

He dribbles some of the lube down Vic's asscrack. Then pours a generous amount on his hand.

He smears it on his big black cock.

I watch, dazed, Clayton's dick glistening from the lube as he slides a couple fingers between Vic's ass cheeks. Rubbing, almost stroking the blonde teen's anal flower.

"I'm gonna lube your insides, just a little. I want you to thank me though." All he gets from Vic is sobs. SMACK! He slaps the prone boy's ass. "Thank me!"

"Unh. Unh. T...thank you." Vic stammers between sobs.

"For what?! And you call me daddy from now on." Clayton demands.

"Th ... thank you daddy. Fuh...for lubing my asshole." Vic moans in despair.

"Hm, yeah. That's a good sissy bitch." His 'daddy' tells him.

Then Vic groans loudly as the black boy pushes a finger in his asshole up to the first knuckle.

"Oh, yeah! This is goin' be good. You nice an tight, bitch." The black bully tells him.

One of the other boys shoves a rolled up pair of the black teens underwear in Vic's mouth. He doesn't want to accept it, but then he didn't want to suck black dicks either. It doesn't matter what we want.

Satisfied that the boy's ass is lubed, Clayton spreads Vic's butt cheeks and presses the tip of his big dick against the boy's little pucker.

"Ooh, this bitch is tight!" Clayton grins at his friends. I watch as the dick slowly pushes its way into Vic's ass. My friend moaning around the underwear forced in his mouth, and pounding his fists against the mat from the pain and violation.

Slowly the black fuck stick disappears into Vic's rear. First the purple tip, swallowed by my best friend's ass. Then inch after inch of giant black fuck stick. Slowly driving into the hysterical teen. Until finally Clayton's balls come to rest on the boy.

"Mmn, how's that?" The black teen asks. All Vic can do is make garbled painful grunts. "Good, good. You gonna love this next part."

With no gentleness, Clayton pulls his cock most of the way back out before swiftly ramming it back in.

Vic's eyes go wide, and he goes silent. As if the air was knocked out of him. or maybe his soul.

Uncaring, Clayton begins fucking my friend's ass fast and hard. Vic grunts with every thrust, but it's as if the light in his eyes have gone out.

Something in my best friend has permanently broken.

Clayton fucks him energetically for a couple minutes. Laughing and joking with his friends as Vic passively grunts with each thrust. Then the black bully pulls his big dick out of Vic's ass with a slight 'pop!'

The big teen moves over behind me.

"Ok, bitch, your turn." I feel his strong black hands tug my panties down, just barely uncovering my own round ass. The cool air against my revealed skin sends shivers through me.

One of the other boys gets down on Vic. Laughing and quickly shoving into the violated boy's ass.

I feel Clayton's lubed fingers probing at my own anus. Rubbing and circling my virgin flower.

"What do you say." He growls above me.

"Thank you daddy." I whine. I can feel the slightly painful, unwanted pressure as he pushes one finger inside me.

Then it's out. But my relief is short lived as something large and unyielding presses against my tight bud.

I clench my eyes against the white hot pain, gripping the edge of the mat. Clayton's big dick slowly pushing deeper and deeper in me.

After what seems like an eternity I finally feel his balls against my rear. His curly black hairs tickling my taint.

"Mmn, you tight too bitch. Best thank me for fucking you." He whispers in my ear. His dick deep inside me.

A man's dick is inside me.

Beyond the pain, I feel...I feel strangely full.

I would have thought having another boy's dick up my ass would have removed any sense of my manhood. But it wasn't anything on par with what was burned away when I whimpered, "Mmn, thank you daddy. Thank you for fucking me."

Clayton laughs at my humiliation and pushes my face against the mat as I feel his dick slide out. Only for it to slam back in.

"Unh! Unh! Unh! Unh!" I grunt as he fucks me. Sounding more like a girl with each thrust.

My face rubs against the mat as Clayton jackhammers me. My little penis hard beneath me.

The first boy has finished with Vic. Then he too is replaced. Cum leaking out of my quiet friend's gaping asshole.

Finally daddy's dick twitches. I can feel it all up and down my abused hole as he fills me with his hot jizz. He groans loudly above me as he orgasms.

Then he swiftly pulls out. My ass clenches over and over. As if it wants to be filled again.

I don't have to wait long. Jarome climbs on me and easily sticks his own massive dick up my rear.

I lay there and take it. Degraded, as the big black teen fucks me.

Minutes pass. I can see his friends getting dressed. Vic looks unconscious. Yet still the big black teen fucks me. His big dick grinding in and out of my sore rear.

Finally he grunts, "Bitch! Yeah!" As he fills my ass with his hot cum. Emptying his balls into me with a few final hard thrusts.

All I can do is lay there, my ass twitching over and over. My mind spinning, I feel dizzy and sick. I don't even notice when the black boys leave.

Finally I sit up, only to find my little prick had drizzled it's own cummies in my panties.

I should have taken them off, but used and ashamed I simply pull them up. My cum, and my bullys' cum smeared on my body.

I shake Vic till I see some signs of life. Finally he moans and sits up. He seems really out of it.

I help him dress, and put on my own clothes. Then we make our separate ways home.

Black boys' cum leaks out of my ass, into my frilly panties for the next hour.

The next week passes slowly. Mom can tell something is wrong. I tell her I'm getting bullied a bit at school. But when she asks what she can do to get involved, I just tell her to keep out of it.

Vic recovers even slower than I do. Missing a couple days and seeming distant even when he is at school.

The next Friday when I get to school something feels different. Kids are looking at me. Laughing behind my back it seems.

By lunch it was in front of my back. And people are calling me names in the halls.

Finally someone showed me. Pics have been posted to a message board a lot of students use.

Apparently that morning it was just a couple pics of me and Vic in our underwear. Later, a picture of us lightly kissing. Then by lunch it was of us making out, with hands down each other's underwear.

That was it then. My reputation, such as it was, was ruined. But now the abuse could end.

Or so I thought.

After school Clayton's boys bring Vic and me back to the gym.

My blond friend is very docile. He keeps his eyes downcast.

"This is over." I announce. Trying to sound strong.

"Ain't nothing over, bitch. This was never about the pictures." Clayton says casually, sitting atop a pile of wrestling mats. He makes a motion.

Jarome grabs me and forces me on my tummy across Clayton's lap. I struggle, but can't stop him from pulling my jeans down. Then my blue lace panties.

WHAP! He begins spanking my ass hard. Again and again. The sting of his strong black hand against my tender rear. The other boys laughing at my painfully delivered lesson.

With my ass feeling like it was on fire from the vicious spanking I beg, "Please, please daddy! I'm sorry. I'm so sorry. I'll be good daddy. I...I'll be a good girl." I don't know why I said that last part. It just sort of came out.

He stops and pushes me to the floor. I rub my burning rear with tears in my eyes.

"It's time for your next step to becoming sissies." The black teen looks down at me. "Shave everywhere below your eyes. On Monday you will wear a skirt. Something above the knees. To show off your new smooth sissy legs. And a pretty top. Maybe a silk blouse or something. You will figure it out. Now make daddy happy." He sneers at me.

Sniffling, like the little sissy I am, I lean in and pull out his big black dick. I can hear Vic drop to his knees behind me to please the other boys.

Soon we have both swallowed a couple loads of black boy juice.

I wipe jizz from my chin as the chuckling bullies walk away.

Over the weekend I start to panic. I need some girl's clothes, but am almost broke after buying a bag full of panties.

Not sure what else to do I tell my mom. Not the whole story, just that my bully was demanding I wear girly clothes to school.

She demanded to know who it was, and finally I told her. Knowing it was a mistake immediately.

Looking him up, she calls Clayton's parents.

"They are coming over to talk things out." My Mom looks smug when she hangs up the phone.

But when she answers the door an hour later four teen boys push in past her.

Clayton and his gang were in my living room with me and my mom.

"You ratted on me, little bitch?" He asks seeming only a little angry as he and his boys look my mom up and down.

She is wearing slacks and a button up blouse. Her brown hair tied back in a bun. Still she is lovely. Curvy with E-cup breasts and a big round ass. She has a tummy and is quite a bit thicker than in her youth, but she carries her forty three years quite nicely.

"Look we talked on the phone but you're not Mr..."

CRACK! Clayton slaps my mother across the face.

"Shut your mouth, whore." He tells her. Then, looking at me, "Just remember, bitch, it was you who brought your mommy into this."

Jarome and another boy grab my mother's arms. She struggles, but can't stop Clayton from grabbing the neck of her blouse. With a grunt he tears open her shirt. Buttons flying across the room as the boys cheer.

The only thing left covering my mom's big breasts is her black lace bra. Her chest heaves and her ample cleavage jiggles.

"No! No please." She gasps.

Looking smug the big teen flips the bra up, and her beautiful tits come tumbling out. He grabs them, groping and squeezing as she moans in humiliation. His dark fingers a stark contrast against her pale flesh. He shakes and jiggles them as he grins.

I watch, fascinated and horrified. My mother is being reduced to a sex toy for my bullies. I realize that I find her big tits arousing. My sissy bump starts to twitch in my panties. Getting hard watching my mother's abuse.

Jarome reaches around and unbuttons her pants. Tugging them down as she closes her eyes and moans. Revealing sheer, black lace panties, and the fact that she has a completely bald cunny.

All the fight seems to have gone out of her as they pull her shirt and bra off. Clayton roughly squeezing and sucking her lovely orbs.

Then, grinning, he reaches down and grabs my mother's pussy through her panties. "Lets do this." He whispers. Squeezing her precious spot

Coming back to herself, Mom struggles as they bend her over the arm of the couch. "No! Oh no!" She yells.

Clayton tears her panties down. my eyes are locked on her now bare ass. Big and round, jiggling in her struggle.

The big teen pulls out his black cock. He leans in and grabs her hair by the unraveling bun, forcing her head up so she looks at me.

Our eyes lock, my mother's and mine. She silently begs me for help.

Then... "Noooooo!" She wails as Clayton shoves forward. His big black cock impaling my beautiful mother's wet cunt.

Fucking her.

My bully is fucking my mom.

She grunts with each thrust. Her eyes clenched shut now, as he slaps her big ass in time with his pounding. Her ample flesh rippling. Her big tits flopping together.

I can feel my sissy dick straining against my panties as I watch.

Time passes so slowly as he fucks my mom. Her ass turning red from his constant spanking. He lets go of her hair and it falls, sticking to her sweaty face as her head hangs down. One of the boys taking pictures on his phone.

Mom's hands grip the couch cushion tight as she moans. She looked humiliated, but I can see her obvious pleasure as the big black dick uses her.

Finally Clayton cums deep in her pussy. She gasps for air, breathing heavy as he pulls out. Giving her big ass a final slap.

Exhausted, she watches him walk over to me. Watches as I drop to my knees. My mother watches without a word as I reach up and suck his soft slimy dick into my mouth. I can taste his cum as well as my mom's juices. I grab his ass as I take his whole soft dick in my mouth. moaning like a good little bitch.

Mom groans as Jarome shoves his big black dick up her punished twat. He reaches around her big belly to find her flopping tits. She gasps as he starts to pinch her nipples. Soft at first, then harder and harder. Slapping her breasts together as he fucks her.

Everyone watches as my mother orgasms loudly. She cries out as her whole body shakes like she is possessed. Brought to the height of ecstasy by the boys' abuse.

With The black teen fucking her, she continues to shake uncontrollably for a full minute. Till she finally comes down. Panting and groaning.

After he finishes, I suck Jarome's dick clean as well. Then the other two boys. Each having a go at my exhausted mother, bent over the couch.

Then, pulling me by my hair, Clayton makes me crawl over behind her. "Clean that up, bitch." He orders, pointing at mom's gaping, soppy, cunt.

I lean in, grabbing her ample rear, and suck the disgusting creampie out of her abused hole. My tongue deep inside her. She moans, still bent over the arm of the couch.

The black boys laugh as I lick my mother's messy pussy. I stick my tongue in as deep as a can. My nose shoved between her asscheeks as I taste cum and mother's pussy juice. She pushes her wet twat back against my face. Shivering in her pleasure.

When my moaning mother is nice and clean I pull back and look up at Clayton. Mom's juices still slick on my face.

They made me strip and stand in the middle of the room. My tiny penis hard for all to see.

Then Clayton grabs my mom by her unraveled hair. Lifting her head he slaps her a couple times. Just so she knows her place. Then pushes her to the floor in front of me.

"Suck the bitch off." He orders her. She looks up at him, then docily starts to suck on my little prick. She massages my balls and hums a little. Mom seems to be an expert cocksucker. The pleasant sensation quickly pushes me over and I drizzle my little slime on her tongue. She swallows it all.

The boys show her the pics they have taken of her. Especially the ones where we committed incest. Then they take off.

Silently, and still naked, my mom heads upstairs.

I hear her run a shower, then hear the door to her bedroom close.

She doesn't come out till the next day.

"We need to take you shopping." She tells me, after a silent breakfast. "You need new clothes. Proper sissy clothes." I shiver with a strange excitement at her matter-of-fact words.

Mom takes me to the teen girl's section of a department store.

She picks out some cute skirts and tops. Making me try them on in the changing room.

"We need to get you some training bras." She tells me. "Take off you shirt and try these on." We are standing right in an isle. People can see as I pull off my shirt. I shiver from humiliation as I try on my first bra. Right there. In front of anyone passing by.

It's a pink cotton number. With sky blue edging and a little unicorn on the band. It feels tight as I settle it on my chest. Constricting, like I'm in some sort of cage.

A wave of titillation flows through me with it on. Settling on my instantly hard penis. I feel both humiliated and vulnerable.

Oh god! I truly feel like a sissy. I can't help picturing hard, black cocks. My mouth waters.

"Now you need some cute nighties. No more boy's clothes for you." She says a little loudly.

I feel humiliated, but my little dicklet is still hard as a rock. I try on the negligees she picks out. silks, satins, and lace.

Finally we head home with my new wardrobe.

During a quiet lunch mom can't stop looking at me strangely. Afterward we heads upstairs where she helps me shave my whole body. I can't help that my tiny penis keeps getting hard.

Afterward, she heads to her bedroom.

I put on a pair of pink silk panties and a big T-shirt. I stare at the training bras laid out on my bed for a few minutes. Fascinated and shamed by the thought of wearing them.

With no pants I feel vulnerable walking around the house. Vulnerable and strangely feminine. The air caresses my shaved legs as I walk. My sissy bump keeps getting hard in my panties.

In the evening, when she comes downstairs mom has put on lingerie. A sheer white set, with little blue bows. Stockings, a short skirt that doesn't quite cover her ample ass and matching bra that barely holds her big tits. I can see that she isn't wearing panties.

"I need you to make mommy feel good, Willard." She tells me as she sits on the couch and spreads her legs. "Strip to your underwear, but put on a bra." I rush upstairs to do as told. Excited, even though I know this is wrong. So deliciously wrong.

I pull my T-shirt off. Shivering as I grab it by the bottom and pull it over my head. Like a sexy woman would do in an R rated movie. Feeling even more feminine.

I pick out a pink silk bra. One that matches my panties. I struggle to pull it on. Not used to the strange clothes. It still feels tight around my chest. Binding, like the whole world is dominant over me.

I stop and stare at my mother in the couch. Her in some slutty lingerie. Me in girly bra and panties. The whole thing feeling unreal.

"Good, now crawl to mommy." She orders, giving me a stern look. Slowly caressing her inner thighs.

I get to my hands and knees and crawl. Stopping between her meaty thighs. The awkward bra feels tight around my torso, and over my shoulders. I feel warm, there are butterflies in my tummy.

"Lick mommy's pussy. That's a good girl." She tells me.

I brush her small skirt out of the way and lean in. I kiss her bare pussy all over, fascinated by her soft, warm flesh. Excited at our incestuous play. Mother leans back and moans her pleasure above me.

She shivers as my tongue tickles it's way between her labia. She gasps when I drive it as deep as I can, tasting my mother's juices.

She whispers some advice on being a better pussy licker as she gets closer and closer to orgasm. Her hands squeezing her own big breasts. Pinching and pulling her nipples through her sheer bra.

Mom finally cries out her pleasure as I lap up her free flowing cum.

I lay my head in her lap after our...interaction. Still kneeling before her. I say, "You know I'm not a girl."

"Oh, honey." She says kindly. Petting my hair. "Of course you are. You are my little sissy girl, and I love you." My body shivers at her words, and my little prick gets hard.

"Uh, what about my needs?" I can't believe what I'm asking.

She nods, and I get excited when she leads me upstairs.

I had always thought my mom was hot, but was never sexually attracted to her. Not until I saw her get fucked like a whore. Not until she sucked on my little dick.

Now my tiny pecker was hard as a rock as I thought about what we were about to do.

When we reach my room I'm surprised when she pulls my pillow off the bed and makes me straddle it on the floor.