Sissy Training

Brianna - Mommy lets Sissy Son out of Chastity before First Date (1080 HD)

1080 HD Brianna is so proud that her son is wearing the new bra and panty set that her daughter picked out for him, but she reminds him that soon he will have to choose his lingerie on his own. Brianna decides to unlock her son’s chastity device, just so that she can abuse his penis and balls. This is to remind him that his penis and balls no longer matter. She slaps, pulls and squeezes them as her son cries out. Brianna threatens to take him to the doctor and have them removed. Her son’s gender is now female, Brianna has decided. Her son’s penis is now useless and from now on he will be getting fucked in the ass by Mother’s big strap-on. Brianna will teach her daughters how to fuck with the strap-on as well, so that they can help Mother train their brother. Brianna’s son just can’t seem to help but keep leaking. Brianna takes her son’s pre-cum and forces her to swallow it. She is going to need to practice because her prom date is going to want her to swallow. Brianna’s son puts up a fuss, but Mother makes her do it. Brianna’s son objects. She does not want to be trained to swallow for her prom date. Mother grabs her son’s balls and hits them harder. Brianna’s son is displaying the wrong attitude. Good girls learn to swallow. Brianna’s son cries, but it’s all for her own good. (9:04 long)

 

 

Runtime: 
9:04
Rate this: 
2.25
Average: 2.3 (4 votes)
Kimber and Raven - Mom and Daughter train Sissy Slut with Huge Strap On Cocks (1080 HD)

 1080 HD Raven never wanted Marcello. She always wanted to have two daughters. Instead of a second daughter, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her daughter, Kimber. Kimber has always wanted a sister. She’s happy to help her mom make Marcello into the sister she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.

The mother and daughter are ready to help prepare Marcello for his new life as a girl. To continue his training, he will be shipped away to Raven’s sister’s house. Raven’s sister runs a home for sissies, where to earn their keep they are whored out on dates. In preparation, generously, Kimber and Raven are going to help Marcello learn how to take very big cocks. Because Marcello does not have the proper number of fuck holes for a girl, they will have to train her ass to function for men like a cunt.

First, the mother and daughter play dress up with Marcello, who will now be referred to as “Marcy.” Kimber is very excited to share her clothes with her new sister, Marcy. Kimber’s clothes are very provocative, but Kimber tells Marcy that men like provocative clothing on girls. In his new role as a sissy slut, his function will be to please men and do things that they like. Learning to wear revealing clothing for men is just a start.

Kimber and Raven are really pleased with Marcy’s transformation. They’ve spent enough time on Marcy’s new look, now, it’s time to train her to get fucked like a girl. Kimber and Raven spit-roast Marcy. She must learn how to suck cock while getting fucked from behind. This kind of sexual multitasking is foundational for a slut’s training. Raven begins the ass fucking with a large dildo.

Marcy’s new sister has an extra-large sized dildo, even bigger than her mom’s! Kimber thrusts the enormous dildo deep into her sister’s “pussy.” Marcy cries out. It’s too big! But Kimber and Raven insist that Marcy must learn to take it. She will thank them for the good solid training once she is earning her keep as a whore. Good whores do as they’re told. Marcy must learn to be a good whore. With Marcy flat on her back, Kimber fucks her ass while Raven fucks her throat. Her pink chastity is in full view. Marcy is well on her way to becoming an excellent sissy slut. (17:34 long)

 

 

Runtime: 
17:34
Rate this: 
4
Average: 4 (7 votes)
Astro and Lola - Jane gets Ready for a Sissy Contest (720 HD)

Astro and Lola decide to enter Jane into this year’s Sissy contest.  The sissies are evaluated in 3 categories.  Tightest chastity tube, best cock sucking skills, and best dressed are the areas of interest for the judges.  In this clip, Jane undergoes the humiliation of being prepped for the contest.  Astro and Lola will split the money from the contest.  Jane is forced to admit that he is not a man but a girl.  His penis is too small to be a man.  Jane is dressed in a ridiculous sissy outfit.  The girls teach him how to curtsey.  Next they put of Mary Janes on Janes stocking feet.  They instruct Jane that when she curtseys she must show the judges her chastity tube.  The girls then put makeup on Jane.  She is so pretty!  Next the butt plug.  The girls think the judges will love the butt plug and earn extra points.  Jane lifts her sissy dress and the girls stuff his ass with a pink butt plug.  The girls then instruct her how to walk like a girl and practice her curtsey. Sissy Jane is all ready for the contest.  The rest is up to her.  She has to want it!   (7:00 long)

Runtime: 
7:00
Rate this: 
4.2
Average: 4.2 (5 votes)
Astro and Lola - Cucumber Reaming for Sissy Jane (720 HD)

Jane is back from the Sissy contest with bad news.   The judges said her chastity tube was too big.  They thought that her butt plug was too small.  Jane is humiliated as the girls inspect her chastity tube and butt plug.  They start her cock sucking training with a small gherkin.  Astro shoves the gherkin down Jane's throat.  They need to get rid of her gag reflex.  Next they move to working out and stretching her ass.  The girls start off first with a small gherkin up her asshole.  Jane is humiliated.  Jane has this distressed look on her face as she is violated with the gherkin.  They move on to the much larger cucumber.  Jane bucks against her ties.  Jane is upset her ass hole is being stretched out with a cucumber.  Pretty soon the girls are reaming Jane's ass hole out.  Her hole is getting so big!  Astro then takes the cucumber and start thrusting it harder and deeper into her.  Lola feeds Jane a gherkin while Astro fucks her hole with a cucumber.  Jane bites into the gherkin while she watches her hole being stretched out from Astro’s thrusting.  Jane is being stretched!  Jane is given snack while Astro fucks her ass.  Eat your cucumber Jane!  Jane is completely humiliated.  Astro bangs Jane’s ass from behind in a deep grudge fuck.   This clip also has highlight video at the end as well. (19:34 long)

Runtime: 
19:34
Rate this: 
3.666665
Average: 3.7 (3 votes)
BP - Sister and Friend Turn Brother into Sissy with Help from Mother (1080 HD)

1080 HD Natalya cinches her brother into a tight corset. She and her friend, Chloe, are turning him into a sissy. Danni, Natalya’s brother, complains about what the girls are doing to him. The girls laugh at him and do it anyway. Danni is almost fully transformed. The girls have made her wear a long wig, and pink garters with a matching collar, in addition to her usual chastity device. But Danni really does not want to be humiliated any longer by being dressed up this way. She puts up a stink, and Natalya responds by calling their Mother into the bedroom. Brianna enters to find her daughters quarreling. Brianna must reinforce to Danni that there are no males allowed in the household. She must go along with Mother’s rules and be a good girl. Brianna makes her son put on the satin panties that started the argument between the siblings in the first place. The females finish dressing Danni to fully-transform the awkward young man into a pretty girl. They complete the transformation with a lesson in poise, and taunt Danni with hints at what will come next for her… (14:00 long)

 

Runtime: 
14:00
Rate this: 
4.2
Average: 4.2 (5 votes)
Brianna - Mother Encourages Sissified Son to Appreciate Stockings with Over Knee Spanking (1080 HD)

1080 HD Brianna has been training her son, Danielle, to become a sissy. She has selected romantic fiction for Danielle’s reading material. Appropriate literature is part of Danielle’s mental development, as he grows into an ideal sissy for his mother. Brianna calls Danielle into the room. Danielle has been dressed, head to toe in complete sissy garb. She wears a pink satin corset and pink garters to hold up her stockings. And of course, Brianna’s son has a pretty chastity to match the outfit. Brianna observes her son’s stride in high heels as she approaches. Danielle kneels beside mommy, and mommy pulls back her son’s wig to inspect the makeup application. Danielle has neglected to apply lipstick. Mommy corrects Danielle and reminds her that lipstick is very important for a good girl to wear. Brianna moves on to inspecting her son’s chastity. Danielle complains to her mother that she has been in chastity for a very long time. Brianna makes her son thank her for keeping her in the device. It’s for her own good. Danielle understands that mommy knows best, but doesn’t like that she must wear head to toe pink. She is especially frustrated with the pink stockings, which are sometimes itchy.  Brianna is disappointed that her son has not yet learned to appreciate stockings. Brianna encourages her son to appreciate the softness of mommy’s stockings by massaging her feet. Danielle massages her mother’s feet. Brianna encourages her son to inhale the smell of her feet and kiss them. She reminds her son that training is necessary, because Danielle will be sent to her aunt, Alexandra for the summer. She wants Danielle to perform well at her aunt’s parties. Danielle complains. She hates spending summer with Aunt Alexandra. Alexandra spanks her, and it hurts. Brianna brushes aside Danielle’s complaints and starts to read to her from the romance novel. The novel helps mentally groom Danielle to be attracted to men. Danielle will appreciate the preparation once his mother and aunt start sending her out on dates. Danielle brings up the spanking again and complains to her mother that one-time Aunty Alexandra bent her over her knee and spanked her very hard. Danielle was upset and couldn’t sit for days. Brianna tells Danielle that she just needs to get used to receiving a hard spanking. Brianna pulls her son over her knee. She begins to strike her sissified son’s bottom one hundred times, compassionately, to prepare her for more extreme punishments from her aunt. (8:08 long)

Runtime: 
8:08
Rate this: 
4
Average: 4 (2 votes)
Cali and Kenzie - Double Handful for Besties Shared Bitch (1080 HD)

1080 HD After we filmed “Cali and Kenzie - Sissy Trained to Take Cock with Machine Fucking,” Kenzie wanted to see if she could get her whole hand inside Marcello. Cali’s had some experience with making meat puppets out of sissy faggots, so she guides her best friend, Kenzie, through the process in this behind the scenes clip. Pretty soon Kenzie is wearing Marcello like a glove! When Kenzie pulls out, Marcello’s left with an anal gape. Cali finger fucks Marcello’s ass while his little dick swells in tight chastity.  (4:37 long)

 

Runtime: 
4:37
Rate this: 
4
Average: 4 (6 votes)
Cali and Kenzie - Sissy Trained to Take Cock with Machine Fucking (1080 HD)

Kenzie flips through a publication while her sissy is fucked by machine. The sissy has been strapped into a stockade and is completely helpless as its ass is pounded by the motorized dildo. Kenzie ignores the sissy’s whimpers as she reclines on a pink chaise. Cali drops by to visit. She’s equally interested in the magazine Kenzie’s been leafing through and joins her friend on the chaise for a cuddle. The friends chat about the publication and talk about nail salons, completely ignoring the sissy in training. Kenzie shows Cali how she’s been wearing the sissy’s chastity key for two months as part of its training as well. Cali thinks it’s great! To impress her friend and show off what a slut her locked up sissy has become, Kenzie turns up the speed on the fucking machine. The sissy complains that the adjustment hurts, but the Princesses just laugh. It’s chastity rocks and bobs between its legs as it gets pounded by the machine. Cali shows it some training material from the magazine while it gets fucked. The Princesses gang up and taunt the helpless sissy. They play with and vary the speed of the huge cock violating its tight asshole. Kenzie shoves her fist into the sissy’s mouth and makes it gag on its own taste. Cali takes the controller and cranks the machine up to maximum speed. She finds a blonde wig and puts it on the sissy’s head. Cali makes the sissy kiss her shoes while wearing the blonde wig and getting fucked. Kenzie leaves to get ready for her nail appointment and asks Cali to supervise the sissy for her. Once Kenzie leaves the room Cali cranks the machine way up. The sissy starts to cry out and make a fuss, but Cali tells it very firmly to shut the fuck up. (14:13 long)

Runtime: 
14:13
Rate this: 
4.42857
Average: 4.4 (7 votes)
Amadahy, Noe, Slut Jane, Female Domination, Sissy Sluts, Strap On, face fucking, sissy training, chastity

Amadahy spits on the strap on cock that sissy jane has just sucked. She commands jane to bend over the kitchen counter and present her ass. Noe gags jane with a lollypop while Amadahy enters her. Jane’s chastity bobs as Amadahy fucks her from behind. Amadahy plans the slut’s dates for the week while she fucks her. Noe sadistically giggles and holds jane’s head while she forces her to suck the lollypop. When the Princesses are done having their way with her, they make jane kiss their shoes. Noe puts the sweet back in jane’s whore mouth. Jane looks such a mess, and sucking things always seems to make her feel better. The Princesses leave. Jane sits against the counter and is very sad. She eats the lollypop and looks as though she might cry. (8:18  long)

Runtime: 
8:18
Rate this: 
4
Average: 4 (5 votes)
Brat Princess - Danni Forced to Cross Dress then Fucked Part 2 (720 HD)

Danni is gagged with the pink lollypop while Amadahy applies more blush. Noe applies heavier eyeshadow on their slut. Kendall tells danni to suck on the lollypop gag like a cock. Amadahy holds up a hand mirror so that danni can see his dick sucking lips. This is what his life will be like as a girl. Each day, an endless barrage of cock will breach the barrier of danni’s mouth and fill her body. This will be for the rest of her life. Again, danni protests that he’s a boy. Danni still isn’t getting it. Kendall tells danni to be still while Amadahy applies his mascara. They don’t want him to lose an eye, because no one would talk to a one-eyed girl. The Princesses decide that later they will get the strap-on and teach little danni how to suck cock properly before turning her out. They can make danni look like a girl, but they are not sure if his tiny male brain can handle thinking like a girl. But, they can train him the best they can. Noe holds the mirror and forces danni to look at herself while Amadahy applies a blonde wig. Amadahy tells danni that as a boy he’s just a useless virgin, but as a girl he’s much better. The Princesses re-name danni “Jane,” because she is such a “plain Jane.” They put frilly white socks on their “plain Jane.” After the white socks, the Princesses give Jane mind control shoes. The mind control shoes will turn plain Jane into an instant slut. “Everyone is going to want to use you.” Amadahy states. With the mind control shoes in place, Amadahy cuts Jane free of her bondage. The Princesses present Jane with new lingerie. Jane doesn’t know how to put a bra on. She hasn’t been a girl very long. Amadahy teaches her. Jane’s boobs are so little. She’s probably going to need implants. “Jane, smile don’t pout. Pout gives frown lines. You don’t want to be an ugly girl, do you?” Amadahy asks. Jane smiles. The Princesses teach Jane how to walk. Jane walks like a slut. They make Jane twirl. Jane twirls until her dick flies out of her panties. The Princess notice and make Jane tuck it back in. The Princesses take a selfie with their new girlfriend Jane. Jane looks sad when she sees herself in the selfies. As a girl, Jane is allowed the privilege of sitting on the bed. Amadahy poses Jane for a photo with the lollypop and her hand down her panties. The Princesses prepare Jane for her next lesson. She’s going to have to learn how to suck and fuck like a girl… (14:22  long)

Runtime: 
14:22
Rate this: 
4.8
Average: 4.8 (5 votes)

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