Sissy Training

Christina - Sissy gets made up and taught he is no longer a man

1080 HD:  Sissy Brenna undergoes a transformation.  Christina teaches the sissy chastity slave how she expects her makeup to look every day.  The former boy humbly sits in the chair as Christina puts her hair in pig tails.  Next the eye makeup is put on.  Sissy is finding out it is hard to be a girl and he has to put this on every day!  Christina starts talking with Sissy just like she is a real girl.  She talks about boyfriends and upcoming dates.  “Every girl has to wear lip gloss!”  Christina makes him stand up and twirl.  She then shows off to the camera her pink chastity tube.  She then rubs up against the tube teasing it.  Christina then tells the poor sissy slave all of her house holds duties and what the girls will expect of their sissy.  Christina can’t wait to use the sissy like a real life doll.  The girls will practice putting makeup on and dressing her in silly humiliating outfits.  This clip is mostly about makeup and sissy training with some chastity teasing and training.  (16:45 long)

Runtime: 
16:45
Rate this: 
3.4
Average: 3.4 (5 votes)
Bella and Christina - Sissy is Beaten for Breaking a Rule (1080 HD)

Sissy Brenna is caught breaking a rule.  The sissy has to be dressed properly to serve the girls at the sorority house.  The sissy was told the rules and now she has to raise her dress for a whipping.  Christina delivers a powerful whipping while Bella verbally assaults her.  Bella is very demanding.  She wants to be taken care of properly.  The girls inspect her pink chastity tube and laugh at her predicament.  The former boy stands naked except a chastity tube while Bella decides more punishment and goes through the house rules for sissy.  CLIP CONTAINS:  SISSY DOMINATION, HUMILIATION, CB 3000 HUMILIATION, WHIPPING, and VERBAL HUMILIATION.  (10:39 long)  BONUSE FOOTAGE!  This clip contains sneak previews to “Bella and Christina - Ball Kicking Brutality (No Remorse)”, and “Gia - Open your Mouth when I Masturbate Over You”.

Runtime: 
10:38
Rate this: 
4.4
Average: 4.4 (5 votes)
Torie - Cuck Gets made up for his first date (BJ Lesson) Part 2
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Previously unreleased.  Torie humiliates a cuckold in this unreleased classic. Contains:  ass worship, cuckold humiliation, Princess dressing, and putting makeup on cuck.  She teaches her cuck how to suck cock.  They are both going on dates tonight!

Runtime: 
6:24
Rate this: 
3.42857
Average: 3.4 (7 votes)
Brat Princess - House Sissy Trained for Tea parties and Dates (Part 3) (720 HD)

In Part 3, the girls discuss Sissy Brenna’s first date as a girl.  The girls make nervous Sissy Brenna curtsy one more time.   The rest of the clip is the girls explaining to Sissy Brenna what it is like for a girl her first time with a man.  The chastity tube will make it very hard for Sissy Brenna to cum during intercourse.  Sissy Brenna has to learn to cum while in chastity just from being pounded by a real cock.  Sissy have to learn to cum passively just like a girl.  The girls describe in detail how long and how many dates he will have to endure until he is loosened up enough to enjoy it.  The deflowering will remove any sense of manhood Sissy Brenna has left.  (6:56 long)

Runtime: 
6:56
Rate this: 
3.333335
Average: 3.3 (3 votes)
Brat Princess - House Sissy Trained for Tea parties and Dates (Part 2) (720 HD)

The girls continue to train poor sissy Brenna.  The girls now teach Sissy Brenna how to curtsy for the ladies. When Sissy Brenna messes up, she is whipped.  The girls taunt her while she is beaten.  ‘Left foot forward first, left foot forward fist, left foot forward first”, shout at the sissy as Christina whips her harder and harder.  The Sissy falls during curtsy training and Christina is enraged!  Sissy is whipped hard by Christina and the other girl’s laff at Sissy Brenna during the beating.   (10:48 long) 

 

Clip contains: Christina, sissy whipping, curtsy training, brat girls, verbal humiliation, chastity humiliation

Runtime: 
10:48
Rate this: 
3.333335
Average: 3.3 (3 votes)
Brat Princess - House Sissy Trained for Tea parties and Dates (Part 1) (720 HD)

Sissy Brenna is going to be serving tea for ladies at formal tea parties. Sissy Brenna first gets his makeup put on and is instructed how to put on her own makeup.  Sissy Brenna is struggling with learning how to be a girl. Some of the girls have caught her cleaning floors without her heels on.  Sissies have to be fully dressed and as feminine as possible at all times.  The girls decide that Sissy will be wearing locked heels for now on.  Sissy Brenna is not a real man and is not a real Princess either.  She is a sissy.  The girls humiliate the sissy by making him pull up his dress and pull down her panties.  The girl’s laff at his pink chastity tube.  Sissy Brenna has lost his Pantie privileges. She is allowed only to wear skirts and a chastity tube.  The girls adjust her pig tails and make cruel comments about how much of a mess she is.  Princes Christina decides to whip poor Sissy Brenna.  The other girls laff and giggle at Sissy Brenna’s beating.  (11:19 long) 

 

Clip contains:  Putting on makeup for a sissy, verbal humiliation, chastity humiliation, some sissy whipping, and putting a sissy into pig tails.

Runtime: 
11:19
Rate this: 
3.333335
Average: 3.3 (3 votes)
Torie - Cuck Finds out about his first date
0

Torie is training her cucks tongue.  The cuck is forced to stick his tongue out while Torie wipes her shoes on it.    She pushes hard on the tongue with her shoe to exercise its tongue.  The stronger its tongue then the better the ass licking.  A cuck sometimes has to lick his Princess for hours so it needs to have a strong tongue.  Then Torie lets the cuck knows that Torie has a big double date planned for the cuck.  The bull’s are excited knowing they are going to get blow jobs for sure.  The cuck resists but Torie lets him know that she will be making him up and sucking cock tonight.  This clip introduces forced bi training to a resistant cuck and explores the moment that a Princess decides to feminize her cuck.  The cuck is sucking and licking her feet as Torie casually informs it about his first date.  The cuck will put out and Torie is very excited about doing his makeup.   Tories’ tone goes back and forth from girly and excited talking to a girl friend and going into bitch mode yelling at the cuck.  FOOT WORSHIP, FORCED BI, HUMILIATION. (8:16 long)

Runtime: 
8:16
Rate this: 
3.555555
Average: 3.6 (9 votes)

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