Sissy Training

Chloe – Our Sorority Needs you as a Sissy Tonight

The sorority girls want Danni to be their sissy. A sissy is dressing up as a girl and serving them. Chloe finds Danni a cute outfit to wear. She puts a wig on him and also does his makeup. He looks so cute wearing a skirt and heals. So cute they should call him Danielle. Chloe warns Danni that he must curtsey and show his chastity throughout the night. If not, he will get a dildo. Danni knows this is wrong. But he is so submissive that anything can happen.


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Average: 3.3 (19 votes)
Chloe and Natalya - Panty Wearing Danni Humiliated by Brats

The girls gave Danni a gift. Hot pink panties. Its so humiliating for Danni to always be wearing girl panties. But Danni is privileged enough to be able to help the girls get dressed for their night. He helps get them dressed but is so stupid sometimes that he can’t even do that right. Well, maybe its not because he’s stupid it’s because he can’t control himself. Danni is worshipping Natalyas ass and cums in his pink panties. He wasn’t even jerking off. See, he isn’t a real man. Real men don’t do that. Danni is so sensitive and gets so hard around hot girls. He needs to go see his psychologist. They give him a nice gift, and this is what he does. He ruined it! So now he gets to suck on his cum stained panties and go to the mall and buy himself a new pair. 


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Average: 3.7 (19 votes)
Jennifer and Sasha - Danni Sissy Humiliated by Mean Brats

The girls decide to turn Danni into a sissy!  The girls had so much fun in this clip sissifying poor danni.  The humiliation level is so high.  “We will pick you your boyfriend Danni.  Boyfriends are great!  They buy you things and tell you you’re pretty and do stuff for you.  You will love having a boyfriend Danni!”  They make Danni run around in circles humiliating herself.


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Average: 3.4 (16 votes)
Amadahy and Mia - Turn Danni into a Sissy

1080 HD Amadahy and Mia want to start sending danni on dates. In order to do that, he needs to be able to pass as female. First, the girls tape danni’s cock and balls back between his legs. This way his front will be nice and flat, just like a girl’s. His panties will fit much better and be smooth. Danni’s dates will like that. Then, the girls have him try on a bra and panty set. They want to make sure the tape looks right under the silky panties. The panties look good, so they add a bra. Once the bra is stuffed, he will look great! Just like a girl!

After danni has been taped and dressed in his bra and panties, the girls apply his makeup. The girls make him practice speaking in a high and soft voice. The girls spray danni with perfume and then dress him in a sexy dress. They add a beautiful, soft, blonde wig to complete the look. Danni makes a very pretty girl because he is already very small and slender. The look is good, but danni still needs some skills. Sashaying her hips and walking on a man’s arm are things danni will need to practice.

Finally, the girls add heels and teach danni to walk in them. Danni has a lot of difficulty walking in the heels, but very excited to start going on dates. He will try his best to look very sexy and feminine so that he can be approved to start dating men. They teach danni to sit with his legs closed and laugh gently. He is learning quickly and very soon he will be able to pass well enough to start dating. (20:45 long)



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Average: 3.9 (12 votes)
Sadie - Trains her Submissive Husband with Strap-On Sex

Sadie has been training her submissive husband to get fucked in the ass. She has been working him up to bigger and bigger cocks. Today she wants him to take the biggest one yet. Sadie’s husband complains that the cock is much too big! He does not want to take it. Sadie disagrees, she knows that she can make it fit. This weekend she wants to have her girlfriends over and they will all run train on her husband. She wants him to take the biggest cock to get him ready. It will be really fun to show him off to her girlfriends.

With her husband locked in chastity and dressed in a schoolgirl skirt Sadie starts ramming him with a big dildo. She inserts more and more fingers, stretching him out wide. Then, comes the enormous cock she’s been preparing him for. Despite more protests, Sadie shoves that inside of him, too. While fucking him Sadie lays down the rules for their marriage. She has a long list of demands for her husband and he has no choice but to agree.

Sadie pounds her husband’s ass long and hard with the enormous cock. She taunts and verbally humiliates him while she pounds him. Sadie reveals to her husband that she is going to submit him into an underground ass fucking contest and she expects him to win. This is why she has been so insistent he take the biggest thickest one. First prize is a $100 gift certificate to a chain restaurant. Sadie can already taste the victory. (22:54 long)


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Average: 3.1 (10 votes)
Brianna - Uses Nephew to Help Train Son to Become a Better Sissy Part 2

Brianna’s nephew reapplies her lipstick after she has finished sucking her aunt’s strap-on. Brianna’s son works hard to live up to his cousin’s cock sucking example. After Brianna’s son sucks her strap-on, it’s time for him to get fucked. Brianna’s nephew continues to fix her makeup while they fuck on the couch next to her. Occasionally she glances over and gives her cousin suggestions. “Wear more lipstick, the boys like to see lip marks on their cocks.” And “Try bouncing on it more!” Brianna’s son moans with pleasure while taking his mother’s strap-on. Brianna is pleased. Soon her son will be as lovely a sissy as her nephew. After having fucked them each in turn, she sends the girls to the mall for a shopping trip. Brianna expects them to come back from the mall with new dresses and other pretty things to complete her son’s transformation. (9:36 long)


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Average: 2.6 (7 votes)
Brianna - Uses Nephew to Help Train Son to Become a Better Sissy Part 1

Brianna’s son is not shaping up into the sissy that she wants him to be. Brianna’s sister has made good progress with transitioning her boy, so Brianna invites her nephew over to show her son a good example. Brianna’s nephew arrives fully decked out in pink frills and curls. By comparison, Brianna’s son’s look is very bland. Brianna wants her son to look just as pretty and polished. They have got a lot of work ahead. Brianna’s son protests. Being a dedicated sissy seems like a big commitment, but Brianna won’t take no for an answer. She examines the boy’s chastity devices side by side. Again, her son disappoints. Brianna decides that she will use her nephew to help train her son to suck cock. She makes the boys suck cock side by side. Her nephew is truly an exemplary cocksucker, again an excellent illustration for Brianna’s boy. Next, Brianna pulls up her nephew’s skirt and begins to fuck her. Her son must suck a dildo while watching. Briana’s nephew obediently lifts her skirts and moans with pleasure no matter how hard his aunt trusts. Brianna lifts her son’s chin and softly but sternly says, “Let this be a lesson to you. You’re next.” (16:29 long)


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Average: 2.4 (5 votes)
Amadahy and Mia - Turn Shrimp into a Sissy

1080 HD Amadahy and Mia use their little fool, danni, for foot worship. They plan to turn the little shrimp into a sissy. Danni is not very good at being a boy. He is very small and effeminate. Maybe he will make a better girl. The girls plan his transformation. Being a girl is great! Girls get presents all the time. It is definitely better than being a boy, as danni will soon find out. Amadahhy keeps the key to danni’s chastity device on her ankle. She can’t wait to gaff danni so that his front is very smooth, just like a girl’s. Danni is very distracted by all the feet in his face. He’s not even sure what’s happening. The girls are completely in control. They can’t wait to get danni to the mall so that they can cross dress him in girl clothes. (7:32 long)


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Average: 4.4 (10 votes)
Alexandra - Son Sent Away to Goddess Snow for Proper Sissy Training

Ellis’ mother has sent him away to his aunt’s, Goddess Alexandra Snow, for some proper training. His mother would like for him to become more feminine, and fortunately, her sister is an expert sissy slave trainer. While away at Auntie Alexandra’s, Ellis will be fucked with a strap-on every day. Ellis’ boy parts will be locked away in a little pink chastity cage and auntie will hold the key. When Alexandra sends Ellis back to mother, she will be the prefect fully-feminized sissy girl. (13:56 long)


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Average: 3.7 (10 votes)
Brianna - Mommy lets Sissy Son out of Chastity before First Date (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 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)


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Average: 1.6 (5 votes)