A Tale of Two Sissies by Satinslip

She locks the door behind her, and now there is almost no room left. I feel vulnerable next to her bulk. Small and submissive.

She grabs my shoulders and turns me around. I can feel the satin of her bra. Her massive tits pressing against my back as she reaches around me and grabs my tiny cock with both her wrinkled hands.

As unappealing as she is, I can’t help wishing this was my first sexual experience. Sadly, at eighteen, my first sex was sucking a black boy’s dick.

Why couldn’t I tell her no? Cause a commotion?

Maybe I didn’t want to be further humiliated. Found naked in the women’s lingerie changing rooms.

“Ooh, you don’t have much to work with there do you?” She asks as, in spite of the situation, I was getting erect. Her chubby fingers pinch my tip and pulls painfully as far as my little nothing will go.

I squeal softly at the pain. Clenching my teeth to try and keep quiet. Tears in my eyes.

Chuckling, She gives my little pud a few soft slaps. “Why, you’re just a little sissy boy. Aren’t you?”

“Y…yes, ma’am.” I answer submissively. The old woman roughly squeezes my tiny penis.

Then she actually takes my measurements. Turning me around so she can use her tape everywhere.

“Try these.” Her old hand gropes my sissy crotch, as she hands me one of the panties I had picked out. A soft satin pair. Solidly blue with pink bows on the hips.

They fit quite nicely, even with my small bulge.

“There. They look quite fetching on you young man.”

She continues to rub my little bump through the panties. “Now I think it’s time for you to properly thank me.” She says pulling her own panties down. Revealing a forest of grey pubic hair surrounding a damp, wrinkled cunt.

She pushes me to my knees and puts one foot on the bench behind me. Spreading her legs, and opening her pungent, wilted flower. With one hand she flips her big bra up and begins playing with her floppy tits. With the other she grabs my hair and forces my face against her crotch.

Tentatively I start to lick at her hairy pussy. It’s moist, and tastes salty and sour.

The old woman moans as I caress the folds of her fuck hole with my teen tongue. “Mmn, deeper.” She orders. So I stick it as deep inside her cunt as I can.

“Ooh! That’s it you cross dressing Nancy-boy.” She gasps above me.

She doesn’t last long before her pale, fleshy thighs tremble against my head. Her juices flowing onto my face, in my mouth, and down my chin.

“Oh, you naughty boy!” She says happily. Once she finishes gasping her orgasm.

She puts her panties back on and fixes her bra. Then she steps out of the small cubby.

I quickly dress and leave the dressing room. But when I head out to pick out some panties in the size she told me, the old woman follows.

She escorts me up and down the isles. Making me stop to brows periodically.

When we do she rifles through the lingerie on the shelves with one hand. Ordering me to feel the lingerie. With her other hand she pulls me close in a hug, and shoves her hand down my pants.

She starts to pick out pairs of panties for me, while pinching and roughly tugging on my hard little dicklet.

She hands me panties that are much more girly than what I had planned to buy. Frilly, lacy, and delicate. I can’t imagine wearing these.

Finally she takes me back to her counter. “I can check you out here honey.” She rings the pile of women’s underwear up.

It’s expensive, but she only charges me for around half of it. Then she sees me off with a smirk.

I go home, feeling ashamed. Humiliated.

Needing relief I masturbate in front of my computer. I have some sexy videos of beautiful women on, but it’s just background noise. I can’t get the image of big black cocks, and fat old women out of my mind.

Finally I finish and crawl into bed for a nap before my mom gets home.

The next day is Thursday. Shamefully I put on a pair of pink, silk, panties before dressing and heading to school.

My little penis keeps getting hard rubbing against the smooth cloth all day. Shivers of humiliation and excitement running up and down my spine.

I find myself rolling my hips as I sit in my classes. As if I’m trying to fuck the air. My little penis throbbing in my shameful arousal.

Gym comes and goes without incident. Vic and I have to slow down to let other boys finish changing so they won’t see what we wear.

Alone, we strip off gym shorts. I notice he has on black lacy panties with hearts.

Perhaps that is part of the abuse. Never knowing when they would assault us.

Then Friday passes with nothing as well.

Over the weekend I am happy to wear normal underwear.

Then Monday comes.

They wait till after school. As I am closing my locker I find Jarome and another boy standing behind me.

“You’re coming with us, twink.” He tells me.

I’m not sure I have ever been so scared as he leads me to the gym. To a back room used to store mats for wrestling.

Vic is already there. Naked except for pink lacy panties. His body shivers, but not just from the cold. His arms are crossed over his chest.

“Strip bitch.” Clayton demands, smirking at me.

Soon I am down to my own frilly green girly panties.

“Gonna really make you my bitches today.” He says. “Lay down on your stomachs.” He gestures at some mats piled on top of each other.

“N…no! Oh god no!” Vic says. The big black boy grabs him as my friend tries to run. Easily wrestling him down to the mat.

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.

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