Dildo Training

Lily and Macy - Big Sister Fucks her slave while Little Sister watches and Learns

Macy and Lily are two wealthy heiresses. The girls have collected several “servants” from off the streets. They do not pay the servants, but they are given some meals and shelter. Macy has been largely responsible for keeping the servants submissive, but today she wants to show her younger sister how it is accomplished. Macy selects a skinny punk boy that they found playing guitar outside the mall to demonstrate on. The skinny punk sees Macy’s strap-on and knows that ass fucking is a punishment. He protests that he did nothing wrong. Macy tells him she knows, but she is going to punish him with the strap-on anyway to show Lilly how it’s done. Lilly watches her big sister fuck the skinny little formerly homeless boy. “I’m sorry, I’m sorry,” the little punk cries. It’s all in vain. Macy tells him that if he doesn’t submit to her sexual aggressions he will be right back out on the street. Macy fucks the skinny boy in piledriver. The boy must look at his chastity key dangling between Macy’s expensive breasts while taking it in the ass from her. Little sis, Lilly, holds the boy’s legs back so her sister can get the dildo in his ass ever further. Macy makes the punk boy lick his own ass juices from the dildo. She asks him if he would rather go back to living in his car, busking for spare change, or continue to live in a mansion with two hot blondes. The homeless boy sucks Macy’s cock with renewed enthusiasm. He doesn’t want to go back to the life he lived before. As cruel as the girls are it’s better than homelessness. (11:31 long)

Lily is Macy Cartel’s REAL sister!

 

 

Runtime: 
11:31
Rate this: 
4.157895
Average: 4.2 (19 votes)
Brianna - Mother Straps Dildo to Sons Face and Fucks it in Frustration when Date Cancels

Brianna is mad that her date canceled on her. She will have to rely on her beta-son for an orgasm now. Brianna straps a dildo to her son’s face. The dildo is not as big as her lover’s cock, but it will do. Her beta-son is locked in chastity, of course. His little penis would never do to satisfy any woman. Brianna has her son lay on the bed so that she can use the dildo strapped to his face for an orgasm. She thinks about her lover while riding the dildo strapped to her son. Using her son for an orgasm is ok because he is in chastity. She explains to her son that it is ok to fuck mommy with the dildo so long as he remains locked. The chastity cage bounces and jingles while Brianna’s son fucks mommy with the dildo. After Brianna has climaxed, she makes her son kneel beside the bed with the dildo still strapped to his face. She wants to take a little nap. One orgasm may not be enough. She may want to use him for another when she wakes. (8:37 long)

 

Runtime: 
8:37
Rate this: 
3.444445
Average: 3.4 (9 votes)
Brianna and Kat - Punishment Fucked by Mom and Sister

Ellis must always obey his younger sister. If he disobeys, Mom has given her daughter the permission to punish fuck her brother. Kat will be allowed to fuck her brother as punishment whenever he deserves it. Ellis must serve his younger sister and all her friends, doing whatever they say. If he refuses, Kat will fuck her brother’s ass more and harder! Brianna, Kat and Ellis’ Mother, shows her daughter a few tips on how to fuck a beta like her brother into submission. The state has ordered all beta’s to be controlled by their Mothers until such a time as they can surrender to a Keyholder outside of the family. Kat fucks her brother’s mouth with a dildo while his Mother fucks his ass. Ellis squirms and makes a fuss. The fuck hurts, but he doesn’t have a choice. After the fuck Ellis must thanks his Mother and sister for his beta training. (12:08 long)

 

Runtime: 
12:08
Rate this: 
3.666665
Average: 3.7 (12 votes)
Macy Cartel - Fucks the Cockiness Out of her Bitch

Macy is upset with her little bitch. He’s been acting too cocky lately. Macy has decided that the best punishment would be for her to get a little too cocky, too. She puts on her biggest strap-on. Macy’s bitch looks terrified. The dildo is WAY too big to go in. Macy disagrees. It will fit. No matter how much the little bitch protests he will have to take it. Macy’s little bitch squeals as she works the giant cock into its asshole. He complains that it hurts. Macy likes that it’s hurting him. She reminds him that he did this to himself. Macy doesn’t like all the whining and complaining, and so she fucks him harder. She makes the bitch hold its legs in the air while she fucks it deep. The bitch’s little chastity bounces while she drills him. If he continues to act cocky, Macy’s going to invite all her girlfriends over to run a train on him with their giant cocks, too. She reminds him that she is going to always keep the giant cock nearby from now on. Whenever he acts up, she is going to punish fuck him hard and deep with it. Macy’s boyfriend is on his way over. Macy reminds her bitch that an order from him is just like an order from her. The little bitch is going to have to obey orders and do whatever Macy’s boyfriend says. If he doesn’t obey him, things will only get worse. (15:19 long)

 

Runtime: 
15:19
Rate this: 
3.64706
Average: 3.6 (17 votes)
Alexandra - Cocksucking and Erection Reduction Training

 Goddess Alexandra want to make sure that her nephew, Ellis, is sucking cock skillfully. She wants to make sure that his dates with “gentleman callers” are going well and that the men are leaving satisfied with his work. Auntie Alexandra makes her nephew suck a cock in front of her and assesses his skills. She laughs as she fucks her nephew’s throat vigorously with a dildo. This is Ellis’ performance review. Alexandra makes Ellis deepthroat the cock and hold it there for a while. Later, she decides to let her nephew out of chastity. She assesses her nephew’s body and is pleased with the amount of shrinkage. Alexandra tests her nephew to see if he can still get aroused by her body. Ellis has shrunk to about one inch from his chastity regimen and cannot get hard, not even while looking at his auntie’s panties. Alexandra is very pleased. She knows that her nephew is now ready for his sexual reassignment surgery. (11:29 long)

 

 

Runtime: 
11:29
Rate this: 
3.53846
Average: 3.5 (13 votes)
Brianna and Ivory - Locked then Fucked by the Department of Beta Control

Brianna and Ivory work for the Department of Beta Control. In the new world order all males are measured by the Female run State. Male anatomy measuring less than six inches erect is classified ‘beta’ and locked in chastity. After being locked into a State controlled chastity device (which is illegal to tamper with or remove) the beta’s ass is then trained. They have a saying in the DBC, “Less than 6 gets you 9 inside.”

Brianna and Ivory break in their newly locked beta by fucking him from both ends. It’s very humiliating for the beta male to be fucked by two dildos significantly bigger than his own cock. It didn’t have to end up this way for this particular beta, though. Size-wise he is actually on the cusp of penile regulation. Until recently, he was living with a girl who had claimed him as her boyfriend. But the girl decided to break up with him and so he was sent to the DBC for evaluation. After his assessment the department determined that he is in fact beta, and so they removed him from the dating pool. If only his girlfriend hadn’t tossed him out. He may still be enjoying more relative freedom.

The DBC makes the beta do ass to mouth. He thought he was a good and loving boyfriend. Now the state will introduce him to all sorts of new levels of depravity. “Who owns your balls?” They ask. The beta doesn’t know the answer. “The government.” They reply. After the fucking, the key to his chastity will be kept in a government office. Once a year he will return to the state for assessment. The officers change the male’s name. The paperwork will be filed, and the male’s name will be changed. After the male has been dismissed, Ivory remarks to her superior, Brianna, “I can’t believe this is standard procedure.” Brianna replies, “It’s not. I just like to do it.” The women laugh. (11:50 long)

 

Runtime: 
11:50
Rate this: 
3.2
Average: 3.2 (10 votes)
Brianna - Mother Teaches Locked Son how to Pleasure a Woman (4K)

This clip is in 4K Ultra HD! If you cannot play clips in 4K, get the 1080 HD version instead!

4K Ultra HD Brianna wants to show her son how to pleasure a woman. It’s about time he finally learned. After today he will to do this for his mother and sisters. Brianna’s son has already been locked into a very tight chastity cage. He won’t be pleasuring anyone with that little nub. Instead, Brianna straps a dildo into her son’s mouth. It will be one of her son’s responsibilities from now on to make mommy cum. Brianna’s son does not like the gag, but mother straps it on anyway. The dildo is a nice decent size, unlike Brianna’s sons locked-up little parts. Brianna’s going to be so proud of her son when he finally learns how to get a woman off. Brianna has her son lay flat on the bed and sits on his face while riding the dildo. Mommy climaxes on her son’s face while he remains locked in his little cock cage. Brianna then teaches her son another position. This position, the one with him kneeling at the foot of the bed, is the position his sister favors for her orgasms. Brianna enjoys a second climax in this position. Very satisfied with her son, he decides now is a good time to bring up some of his problems at school. Brianna’s son confides in her that one of the teachers does not approve of how he dresses. Brianna assures her son that she will go to the school and have a talk with his teacher about the feminine clothing she prefers her son to wear. (7:37 long)

 

Runtime: 
7:37
Rate this: 
2.625
Average: 2.6 (8 votes)
Brianna - Mother Teaches Locked Son how to Pleasure a Woman (1080 HD)

1080 HD Brianna wants to show her son how to pleasure a woman. It’s about time he finally learned. After today he will to do this for his mother and sisters. Brianna’s son has already been locked into a very tight chastity cage. He won’t be pleasuring anyone with that little nub. Instead, Brianna straps a dildo into her son’s mouth. It will be one of her son’s responsibilities from now on to make mommy cum. Brianna’s son does not like the gag, but mother straps it on anyway. The dildo is a nice decent size, unlike Brianna’s sons locked-up little parts. Brianna’s going to be so proud of her son when he finally learns how to get a woman off. Brianna has her son lay flat on the bed and sits on his face while riding the dildo. Mommy climaxes on her son’s face while he remains locked in his little cock cage. Brianna then teaches her son another position. This position, the one with him kneeling at the foot of the bed, is the position his sister favors for her orgasms. Brianna enjoys a second climax in this position. Very satisfied with her son, he decides now is a good time to bring up some of his problems at school. Brianna’s son confides in her that one of the teachers does not approve of how he dresses. Brianna assures her son that she will go to the school and have a talk with his teacher about the feminine clothing she prefers her son to wear. (7:37 long)

 

 

Runtime: 
7:37
Rate this: 
3
Average: 3 (8 votes)
Brianna - Mother Trains Son to become Daughter with Chastity and Pegging (4K)

This clip is in 4K Ultra HD! If you cannot play clips in 4K, get the 1080 HD version instead!

4K Ultra HD Brianna never wanted a son. She had two lovely daughters before he was born. She expected the third to follow suit and come out into the world the preferred gender for her progeny. Brianna knows that she can make this right, undo this mistake. Brianna has decided to make her son into her third daughter. Three beautiful girls, that is what Brianna wants. In order to transform her son into her third daughter, Brianna has locked her into a very small chastity device. She makes her gender-transitioning offspring wear nylons and garters, to train her to appreciate such feminine things. Brianna’s son fusses and complains. None of the other boys dress like this, but Brianna’s son is not going to remain a boy, and she reminds him this. Brianna is very frustrated that her son put his sister’s lingerie in the dryer and shrunk it. Wearing lingerie will teach him to appreciate lingerie. It is a very special type of garment and requires special care from gentle hands. Brianna tells her son that she is going to start fucking him, because girls get fucked and learning to get fucked hard will aid with his full transition.

Brianna starts to fuck her least-favorite daughter. Brianna’s daughter begs her Mother to stop, but inside the metal cage her little clit is throbbing. Her third daughter must learn that the other two siblings, who were born the correct gender, are allowed to fuck all her holes as well. Mother also reminds her son that soon she will be wearing dresses all the time, even to class. Wearing a dress to class would be so mortifying! He’s a boy! No, Brianna corrects her son. Once they put in the work no one will be able to tell the difference between him and all the other girls. Brianna’s son cries. He doesn’t know why he was born this way and doesn’t understand why his mother seems to hate him so much. Brianna knows that she is only doing this for her daughter’s own good. Prom is close, and she wants her youngest daughter to be ready for her prom date. Once she starts wearing some of the bright lipsticks Mommy has picked out for her, the boys are sure to start to notice how pretty she’s becoming. Brianna’s third daughter starts to make a lot of fuss, but Mommy assures the girl that everything is going to be fine. In fact, she thinks she may send her youngest away this summer to work in the family business, Auntie’s Dress Shop. Once her third daughter has been fully transformed, she can model all the dresses in the shop for Auntie’s wealthy clients. (13:47 long)

 

Runtime: 
13:47
Rate this: 
3.42857
Average: 3.4 (7 votes)
Brianna - Mother Trains Son to become Daughter with Chastity and Pegging (1080 HD)

1080 HD Brianna never wanted a son. She had two lovely daughters before he was born. She expected the third to follow suit and come out into the world the preferred gender for her progeny. Brianna knows that she can make this right, undo this mistake. Brianna has decided to make her son into her third daughter. Three beautiful girls, that is what Brianna wants. In order to transform her son into her third daughter, Brianna has locked her into a very small chastity device. She makes her gender-transitioning offspring wear nylons and garters, to train her to appreciate such feminine things. Brianna’s son fusses and complains. None of the other boys dress like this, but Brianna’s son is not going to remain a boy, and she reminds him this. Brianna is very frustrated that her son put his sister’s lingerie in the dryer and shrunk it. Wearing lingerie will teach him to appreciate lingerie. It is a very special type of garment and requires special care from gentle hands. Brianna tells her son that she is going to start fucking him, because girls get fucked and learning to get fucked hard will aid with his full transition.

Brianna starts to fuck her least-favorite daughter. Brianna’s daughter begs her Mother to stop, but inside the metal cage her little clit is throbbing. Her third daughter must learn that the other two siblings, who were born the correct gender, are allowed to fuck all her holes as well. Mother also reminds her son that soon she will be wearing dresses all the time, even to class. Wearing a dress to class would be so mortifying! He’s a boy! No, Brianna corrects her son. Once they put in the work no one will be able to tell the difference between him and all the other girls. Brianna’s son cries. He doesn’t know why he was born this way and doesn’t understand why his mother seems to hate him so much. Brianna knows that she is only doing this for her daughter’s own good. Prom is close, and she wants her youngest daughter to be ready for her prom date. Once she starts wearing some of the bright lipsticks Mommy has picked out for her, the boys are sure to start to notice how pretty she’s becoming. Brianna’s third daughter starts to make a lot of fuss, but Mommy assures the girl that everything is going to be fine. In fact, she thinks she may send her youngest away this summer to work in the family business, Auntie’s Dress Shop. Once her third daughter has been fully transformed, she can model all the dresses in the shop for Auntie’s wealthy clients. (13:47 long)

 

Runtime: 
13:47
Rate this: 
3.77778
Average: 3.8 (9 votes)

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