Category: Sissy training

Sissy Training Reaches Its Climax

sissy training

 

The door opened, and three massive men walked in, their eyes instantly locking onto the sobbing, painted mess on the bed. I stepped back, crossing my arms and sliding my hand down into my own panties, my fingers already slick.

 

“He’s all primed for you boys,” I purred. “Do whatever you want. He’s a mindless sissy.”

 

The first man didn’t waste a second, ripping the lingerie off him and flipping him over. He slammed his thick cock into the son’s stretched ass with a brutal thrust that made the boy scream. Another man grabbed his hair, pulling his head back to shove a thick shaft deep down his throat, choking off his cries. The third man knelt in front, rubbing his cock against the son’s trembling thighs before spitting on his chest.

 

I watched with hunger, my fingers working my clit frantically. “Look at him!” I shouted over the sounds of slapping flesh and guttural moans. “Look at how he takes it! You’re such a good little hole, aren’t you, son?”

 

The men grew more aggressive, swapping positions, gang-banging the shivering sissy until he was covered in sweat and saliva. As the men all groaned, unloading thick ropes of cum across his face, chest, and deep inside his ravaged ass, I felt my own orgasm peak. I screamed as I squirted violently, my juices soaking my thighs while I watched my son break completely under the weight of the men’s seed.

Sissy Training My Younger Brother

Sissy training When I caught my youngest brother dressed in my panties, I knew he needed Sissy training. If he wants to dress like a girl, he will be the sexiest girl. I will teach him everything I know. He will be the hottest sissy in our town; all the guys will want a piece of his tight ass.

Finding the sexiest lingerie I own, I dressed him in a sexypeach colored crotchless one-piece, lace-trimmed satin number. Put his cock in a little cage; he won’t be needing that anytime soon.

Once he is dressed and sexy, I bring him down to my playroom where two big dick horny guys are waiting to tear into his tight virgin ass.

As soon as they laid eyes on him, their eyes lit up and their cocks stood up at attention, grabbing him by the neck, sticking their dicks in his mouth almost simultaneously, that little faggot tried to stuff both cocks in his mouth, greedy bastard, I stepped in and told him one in the mouth and one in the pussy, they took turns railing his asshole until he was stretched out and leaking cum. That’s the day my brother became my sexy sister.

Sexy Mommy Says “Open!” You Say “Ahhhhh!”

 

sexy mommy

“Open wide, sissy,” I commanded, shoving a thick, ribbed dildo deep into his tight ass. He gasped, his back arching as I slammed the toy home. I didn’t give him time to adjust; I started pumping the dildo violently, stretching his hole to prepare it for the onslaught.

 

“You’re so tight, it’s disgusting,” I mocked, leaning in to whisper in his ear while I reached around to slide a smaller plug into his prostate. “Real men are going to tear you apart. They aren’t going to be gentle with a little whore like you. They’re going to treat your holes like trash cans for their cum.”

 

I swapped the dildo for a larger, flared-base plug, forcing it in with a heavy shove that made him cry out. I left it there, stretching him open, while I used my fingers to ruthlessly stretch his mouth, forcing him to gag on my hand.

 

“Your body isn’t yours anymore,” I sneered, watching the plug disappear into his flushed, shaking backside. “You’re just a vessel for seed. By the time the night is over, you’ll be leaking white slime from every single opening.”

Sissy Training Begins Now My Little One!

 

 

sissy training

I smirked, gripping my son’s chin tightly as I smeared a thick layer of glossy red lipstick across his trembling lips. He looked pathetic, shivering in the sheer, lacey lingerie I’d forced him into. The black stockings hugged his thighs, and the push-up bra gave his flat chest a ridiculous, feminine silhouette.

“Stop shaking, you little slut,” I hissed, my voice dripping with contempt. “You’re not a man tonight. You’re just a piece of meat I’m selling to the highest bidders.”

He whimpered, tears smudging the heavy mascara I’d just applied. When he started to hyperventilate, terrified of the men coming for him, I decided to calm him down in the most degrading way possible. I knelt before him, ripping open the lace panties to reveal his tiny, useless cock. I wrapped my lips around his shaft, sucking hard and fast, not out of love, but to remind him who owned every inch of his body.

“Look at this pathetic little nub,” I mumbled against his skin, glancing up with a cruel smile. “You don’t need this. You’re a sissy. Your only purpose tonight is to take whatever those men want to shove inside you.” I gave him one last, aggressive suck before spitting on his head, leaving him drenched and shivering in his makeup.

Kinky Phone Sex With Food

Kinky phone sex Kinky phone sex with me is never boring. I have no limits, anything goes on a call with me, I am down for anything, I can be daddy’s dirty slut that has a fetish for drinking his cum, or the shy, quiet girl next door that turns into the biggest whore when she drinks.

One of my callers, a really fat, hungry pervert, loves to fuck me with fruits and vegetables. We started with bananas and cucumbers. He would tell me to suck a banana like it was his cock and fuck my tight pussy with a big cucumber, talking me through my orgasm. 

After a while, he said he wanted to try something bigger. He wants my tight hole stretched out, he wants me to fuck a big ass eggplant while he listens, and he gives detailed instructions on exactly what he wants me to do.

Rub that swollen clit as you slide the eggplant in you inch by inch, he says, then when it’s halfway inside, I want you to ram the rest of it in your pussy, fuck your pussy hard and fast until you squirt for Big Daddy.

Of course, I do exactly what he tells me to do, and boy, did I cum super hard. I came so hard I got a cramp in my pelvis. Big Daddy was so pleased, he gave me a one-hundred-dollar tip, he said it was because I was a good little whore for him. Can’t wait for our next call, he wants me to fuck a pepperoni log.

Incest Sex With My Pretty Panty Boy

 

incest sex

 

I walked in and there he was, my pathetic little panty-sniffing pervert, standing in my bedroom with my silky black thong stretched over his tiny cock. “You disgusting little shit!” I screamed. “What the fuck do you think you’re doing wearing Mommy’s panties, you worthless panty boy?”

He froze, face red, but his cock twitched like the filthy slut he is. “Look at you, you nasty little cumrag, humping my underwear like some desperate whore. Does it feel good rubbing your sad dick in Mommy’s dirty panties, you perverted fuck?”

I grabbed his chin. “You’re nothing but a panty-obsessed loser who gets off on his own mother’s scent. Get on your knees and sniff them while I watch, you sick little bitch. That’s right, breathe it in deep, you panty-sniffing faggot.”

He whimpered as I laughed. “Mommy’s going to make sure you never forget what a disgusting, panty-wearing slut you really are.”

Teen Phone Sex Girls and Their Mothers Love Sissy Boys

teen phone sexTeen phone sex girls seem so fun to play with. But sometimes men need mature women too. Teen girls often lack the knowledge of certain kinks and fetishes. But I like to think my girl is a bit different from the typical teen girl because I trained her. She understands a lot of kinks and fetish well beyond her years.

In fact, she brought home a guy she met in one of her psychology classes. She told me she picked up some sissy vibes from this boy. She knows all about sissies. We talk to them all the time on the phone. And we’ve even played dress up with a few sissy boys she went to high school with. So, this boy came over last night and we enjoyed an open and honest conversation about what he likes. He admitted he calls sissy phone sex lines when he can afford it.

He feels torn between his upbringing, which apparently taught him men are the head of the household, and men wear the pants, plus men make the decisions… All that sexist religious bullshit. Then he watches porn, realizes his dick appears tiny and that all he really wants to do is wear panties and suck cock. So, my daughter and I told him his secret is safe with us. We can help him. And we want to help him.

Morgan and I Love Sissy Boys

First thing we did was fuck his ass with a strap on. Morgan and I took turns using his tight little ass. And we did this with him dressed in some of my sexy lingerie. Truly, he looked more like a girl than some genetically born girls. Perhaps he should consider being trans. We turned him into a beautiful girl. And we fucked him like a girl too.

My daughter and I enjoy sissy training. And since sissies come in all shapes and sizes and all ages too, we will continue to work with her sissy school friend. We know he wants to suck cock so that’s going to happen the next time we meet. Male college student by day sissy bitch by night just like most sissies he will lead a double life. And we will make it happen for him. We can make it happen for you too.

Sissy Training to Turn my Son into my Daughter!

Sissy Training

I think my little fag needs some Sissy Training.

I keep catching my little Jordan rummaging through my lingerie drawer again.

He thinks I have no idea, but that little sissy doesn’t look half bad in it

. I always knew my baby was a little faggot, but trying to look at hot as Mommy is a whole different story.

I think I should turn Jordan into my precious little whore daughter. 

If that’s what she wants to be so badly!

I’ll make sure her hair and makeup are just right, a little smudged black, the classic whore look.

Wear my skimpy little outfits and tuck that little clitty into a pair of black lace panties and a little bra to match.

All you need is a pair of heels, and I think you’ll be ready to get fucked like my good little whore daughter

In fact, I have a whole long list of men who would love to use you like a little fuck hole, and nothing else.

Use and abuse you until you’re screaming for mommy to have them stop.

But they won’t stop, baby, that’s what being a good whore is all about.

I can’t wait to pimp out your tight little hole for any big cock that wants you!

Only my beautiful girls get fucked as mommy does!

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Sexy Mommy Lilly is Going to Force my Panties on You!

Sexy Mommy

Sexy Mommy Lilly is going to force my panties on you!

I just think your tiny shrimp cock would look so cute in my pink silk panties.

With the black lace thigh-high stockings and a garter belt to match!

I see you snooping in my closet, trying on my bras, and sniffing your mommy’s undies.

You are being awfully naughty, sissy boy, and Mommy might have to punish you!

I’ll put thick black makeup on your eyes and bright red lipstick.

I want to watch the tears stream down your face as I spank your bare bottom for stealing my clothes.

You’re lucky I won’t take my huge dildo to your ass as punishment! 

You want to be as sexy as your mommy, huh?

Well, I’m going to dress you up and fuck you like the good little girl you are!

 

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I love Sissy Training with little Johnny in his panties!

Sissy Training

I love Sissy Training with little Johnny in his panties.

I keep catching him wearing my thongs, shoving his tiny cock inside, and prancing around the house.

He swears he’s not a little sissy fairy, but even his own wife won’t fuck him anymore!

She needs big black cocks just as bad as you do!

Her boyfriend, Marus, is a strong motherfucker who makes fun of and bullies your chubby ass!

He loves watching you on the treadmill, looking at your ass jiggling in my little panties.

Marcus fucks your fat ass, watching his fat cock slide in and out, stretching out that tight boy pussy of yours.

You love watching Marcus remove his cock from your ass and sticks in right in your wife, giving you a front row seat to Marcus plowing your submissive whore wife.

You both are slaves to his Big Black Cock, now get back down on your knees.

 

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