Sissy Training

Brat Princess - Danni Forced to Cross Dress then Fucked Part 1 (720 HD)

Danni hates being in chastity. He complains to Amadahy, Kendall and Noe. Danni asks to be released. Amadahy reminds danni that he is selfish. They own him. He doesn’t have the right to ask for things. Amadahy points out that he doesn’t use his dick for anything anyway. Nobody wants to have a baby with a bottom feeder. Nobody even wants to fuck one. Danni begs to stay home and jerk off while the Princesses are out. They won’t even have to look at him. This proposal is seriously offensive to the Princesses. Dani is reminded that he owns nothing, not even his body. They own it. The Princesses manhandle danni and make him kiss their shoes. Danni complains that his balls hurt. He is only thinking of himself. Amadahy tells danni that they can fix that by signing him up for his SRS, Sexual Reassignment Surgery. All three Princesses giggle. “I’m a boy, Princess,” danni protests. “What makes you think that?” Amadahy asks. “You’re an it. We decide what gender you are.” She states. Amadahy spits in danni’s face. The Princesses decide to make danni into a girl, just like the Kardashian sisters did to their step-dad. They tie danni down, knowing he will fight it. Danni might resist now, but soon he’ll realize it’s much better to be a girl. The Princesses play “Barbie Girl” to set the mood. They tell danni not to move. If he moves, he won’t get an SRS. Instead he’ll get a DIY at home castration. Either way, the next time he’s getting out of chastity will be to have his dick altered. The soundtrack moves to Shania Twain as danni’s face is powdered. Kendall applies his lips while Noe does its eyeshadow and Amadahy powders. The Princesses decide pink looks best on danni. Kendall produces a pink lollypop as a gift for the pretty new girl. Finally, danni realizes why he’s always been out of place. He is a much better girl. God clearly made a mistake, or cruel joke with his sad life. It’s ok. It can all be fixed by his Princesses…  (14:52  long)

Runtime: 
14:52
Rate this: 
4.8
Average: 4.8 (5 votes)
Amadahy - Chastity Slave Becomes a Sissy Slut (720 HD)

It’s been awhile since Amadahy has heard this particular slave complain about being in chastity. It’s finally realized there is no use for its dick. The slave seams to finally understand that it isn’t a real man. Amadahy feels that it’s time to feminize the slave. Every month the Princesses hold a tea party, where they are served by sissies. Amadahy can’t wait to bring this one and show off what it’s become. Amadahy dresses the sissy in her old bra and panties. The shrink ray has made the sissy small enough to wear a pair of Amadahy’s old high heels. “God, I can’t believe when you were born they kept you a boy. That’s so sad.” She says as the sissy puts on the shoes. Amadahy smothers the slave in her breasts as it struggles with the shoe straps. She suspects that the sissy is bulging in the tight panties. Amadahy makes the sissy practice walking in heels. The sissy will be trained to like cock. Amadahy lists all the additional duties the slave will now have as a sissy. The sissy will never be a real man or a real girl. It will always be a sissy slut. Amadahy introduces her feet into the sissy’s mouth. She tells the sissy that it’s going to be rewired to love cock. Amadahy makes the sissy gag on her feet. She teases the sissy’s chastity with her feet. The sissy’s life from now on will be as though it is a living sex doll. Amadahy tells the sissy to bend over and spread its ass cheeks. It does. The sissy admits, as per Amadahy’s instruction, that it’s going to love sucking cock and swallowing loads of hot cum. That’s all Amadahy needs to hear. She grabs the slut by the ear and leads it into the basement. She’s going to feed it vial upon vial of stored up cum.  (15:49  long)

Runtime: 
15:49
Rate this: 
4.7
Average: 4.7 (10 votes)
Alexis Amadahy and Jade - Sissy Strap on Training Part 2 (720 HD)

In Sissy Strap on Training Part 1, danni began his slut training by having his mouth stretched.  Now, danni’s tight pussy needs to be opened.  Danni’s buyer is super well-endowed, and the girls only have a few hours left to get him ready before he ships out.  Danni’s life has been a luxury compared to what it’s going to be.  Jade starts danni’s training with the smaller cock.  Thankfully, the small cock fits into the tight pussy.  Amadahy has danni practice bobbing on her dick while Jade fucks from behind.  Danni’s chastity bounces as Jade rails his ass.  The girls lay danni on his back.  Alexis takes a turn at danni while his feet are in the air.  Amadahy fucks its throat.  Danni looks very unhappy.  “Where’s your pageant face?” Jade demands.  Danni receives instruction to moan like a girl.  Danni will not make much sound.  Amadahy decides she’ll give the pussy a try with her big dick.  Danni’s hole takes all of Amadahy.  Danni strokes Jade’s cock while Alexis fucks his face and Amadahy fucks its ass.  The girls have to finish with him.  They have a shipment of five new fuck toys ready to be broken.  They quickly hose danni down and pack him to fill the rush order.

Runtime: 
14:59
Rate this: 
4.714285
Average: 4.7 (7 votes)
Alexis Amadahy and Jade - Sissy Strap on Training (Part 1) (720 HD)

Danni has finally been sold.  Today is the day he will be packed in a box for his buyer.  Alexis, Amadahy and Jade dress danni so he can be shipped out.  They want him to be ready to play with the instant his box is opened.  The girls dress danni in powder blue ruffled baby doll panties.  The outfit comes with a matching garter belt and stockings.  It also comes with a blonde wig (not shown).   Alexis puts danni in a pair of her heels.  Amadahy adds the eye shadow and Jade paints its lips.  “SOLD” is written on danni’s chest.  Next, they have to stretch out every hole for the new owner.  Nobody wants a new toy that isn’t ready to play with.  Amadahy stretches danni’s mouth with her big black cock.  All three surround danni.  Alexis fucks danni’s face while the other two restrain him.  The girls train danni to stroke Alexis’ and Jade’s cocks while sucking Amadahy’s.  Danni will have to be ready for anything in his new life.  He’ll have to do whatever necessary to please his buyer and can never say no.  He needs to learn to keep at least three dicks hard, but possibly more. They are satisfied with the first hole.  They force danni to bend over and get ready for his next hole to be stretched…

Runtime: 
10:14
Rate this: 
4.6
Average: 4.6 (5 votes)
Amadahy and Jennifer - Domestic Training and Humiliation for Sissy (720 HD)

Amadahy and Jennifer love hang a new sissy at the sorority house.  She is still getting use to chastity and her boots.  The girls inspect her chastity tube and make sure it is tight enough.  Jennifer will be her chastity coach.  She will help her throughout her chastity training. Jennifer will make sure it is tight and secure.  Jennifer is an experienced chastity coach and asks the sissy a series of questions to make sure she is getting used to it.  Next the girls make the sissy walk.  The girls instruct the sissy how to walk.  One foot in front of the other!  The girls show sissy how to walk like a girl in heels.  Next it is time to learn how to sweep!  The girls teach sissy that whenever a Princess or an Alpha male walks into a room she must curtsy.  The girls make the sissy curtsy over and over.  The sissy is learning that she will be kept in chastity and working at all times. 

Runtime: 
12:43
Rate this: 
5
Average: 5 (3 votes)
Penny - Sissy Maid Dresses Princess (1080 HD)

Danni is finding life as a sissy maid difficult.  “Do you think Princesses dress themselves Danni?  Do you?”  Penny makes Danni help her get dressed for her date.  Penny mocks Danni and compares him to her date.  He has a huge cock, Danni does not.  He is not in chastity, Danni is.  Danni wears makeup and gets on his knees.  Her boyfriend does not wear makeup.  He has a huge ego and cock.  Penny tells Danni that he will be eating her pussy later after her boyfriend fucks it.  He will have to clean her.  Penny makes Danni present items on a serving tray.  Danni is learning that being a sissy is hard work.  Danni dresses Penny and is spanked several times when mistakes are made.   (14:32 long) 

Runtime: 
14:32
Rate this: 
4.5
Average: 4.5 (8 votes)
Lola - Makes a House Sissy Worship Her Feet (1080 HD)

Lola enjoys being in charge for a change.  She loves to be mean and cruel to the house sissy.  She can make the sissy do anything she wants.  Lola whimsically eats strawberries while the sissy bobs her whore mouth on her feet.  (10:19 long) 

Runtime: 
10:19
Rate this: 
4.2
Average: 4.2 (5 votes)
BP - Danni Dressed Like A Girl (Part 2) (1080 HD)

 In Part 2, the girls finish his makeup and start working on his voice.  They put him a wig on him and give him some heel training.  They keep telling him how he is a failure as a man so he should try the girl thing.  It’s for the best.  The girls try teaching him how to dance like a girl.  They give him heel lessons.  Danni will begin a new life as a sissy.  His balls will eventually be removed.  (11:57 long)

Runtime: 
11:57
Rate this: 
4
Average: 4 (2 votes)
BP - Danni Dressed Like A Girl (Part 1) (1080 HD)

Jennifer asks Danni, “Have you ever noticed that you are not like the other boys?  Have you noticed how much bigger they are than you in the locker room.  Why don’t you try the girl thing?”  The girls decide to give Danni a makeover.  First they tape his cock and balls between her legs so he has a girlish crotch.  The girls then use Danni like a play doll.  They make him wear panties and give her a complete makeover.   (12:08 long)

Runtime: 
12:08
Rate this: 
4.5
Average: 4.5 (2 votes)
Penny Barber - Step 1 Sissy Training (720 HD)

Penny Barber is an expert Sissy Trainer.  Little Danni has been assigned sissy training so he can learn to better serve the girls in the Brat Princess Sorority house.  Penny is very strict. She first teaches Danni how to stand like a sissy.  No more standing like a little army man!  He will stand like a girl that he will become.  Penny ties some bells to his chastity tube so he can answer yes or no questions by ringing his bells.  1 for yes and 2 for no.  This means less talking from sissy.  Danni is placed in a posture collar and has to wear stockings!  She locks some high heels into place so she cannot remove them.  She will learn to walk in heels!  Danni is then put in a humiliated sissy dress for him to wear for the girls.  Penny puts some makeup on Danni as well.  Danni is going to make a great sissy or else!  Penny places Danni over her knee and uses a hair brush on her ass.  Danni winces from the pain and humiliation from the beating.  Sissy Danni is learning what happens to a sissy when she fails her duties.  This is a great clip for sissies! (27:18 long) 

Runtime: 
27:18
Rate this: 
4
Average: 4 (7 votes)

Pages