Looks like this sub really needs to work harder on his abs – just look at his soft belly steadily growing red as his Mistresses whip it. But don’t think that they will focus on it only – they will also flog his ass and grace him with a hard tugjob!
Search Results for: sissy boy
Sissy Boy Pegging – Shae Celestine
My Sissy Boyfriend Videos (25 scenes)
Have you ever fantasized about being fucked by your strap-on armed girlfriend, while dressed up as a sissy and treated as a whore? You know your girl is probably willing to switch the roles too! We aren’t oracles, but we know your most intimate dreams.
Sissy Maid Cleans Up Our Boyfriends Mess
Princess Carmela and Princess Lilly command the sissy maid to clean up the mess that their boyfriends made at the party that it was not even invited to. LOL! To make it even more entertaining they dress the sissy maid up in slutty red high heels, lacey panties, and matching bra.
Bitch Boy – Sissy Virgin In Panties Gets It In The Ass
He is so nervous! He sent me lots of revealing photos via fetlife while we flirted but reality is a little scarier. I bet i can help him open up with plenty of bondage and prolonged teasing. Gradually, his ass starts to open up for my hands and toys and he gives up that booty cherry to me.
Girl And Friend Turn Boy Into Sissy With Help From Girl
Natalya cinches her boy into a tight corset. She and her friend, Chloe, are turning him into a sissy. Danni, Natalya’s boy, complains about what the girls are doing to him.
Mistress Ariel Caning The Sissy Slave
Mistress Ariel’s slave is a nasty boy, wearing a corset, sexy stocking and high heels, while Mistress Ariel canes his ass brutally. She wants to teach him a lesson while he is wearing these women’s clothes, working her cane on his ass.
Mackenzie Moss – My Panty Boy-Toy
Mistress Mackenzie Moss has picked out the perfect pair of pink ruffled satin panties to wrap around your sissy clit stick. She knows your life would be that much better as an owned sissy girl all dressed up for her. Now be a good slut and put on these pink panties and pull your cock out to the side. I want to see you stroke that sissy clit stick as you show me just how horny it makes you. In fact, I love you in panties so much that I think I am going to keep you like this at all times. You don’t need your ugly boy underwear any more so go throw them in the trash so you have no choice but to always be a panty wearing sissy.
Emily Willis – Secret Sissy Lover
I am going to allow you to even be my dress-up dolly and wear this pink lingerie wrapped tightly around the curves on my body. Now rip those boy clothes off and throw them in the trash as you have no use for them anymore. I am going to turn you into my secret lesbian lover kept completely under my control and made to do the naughtiest of things a sissy only dreams about. Ohhh I see your cock loves the feeling of my panties gripped tightly around it as it begins to get extra hard for me. Now pull it to the side, grab it tightly and show me just how much you love being my sissy slut bent over ready to take any and everything I give you! xxxo Mistress Emily Willis.
Isabelle Deltore – Sissy Clit Trainer
Mistress Isabelle Deltore is going to train that clitty of yours to cum just like a bitch. She has extra pinky sissy lingerie picked out just for you to dress up in and become her sissy slut doll. Now be a good girl and burn all those boy clothes as from here on out you will only wear pink. You will only cum when given permission and you will always be on your knees with your mouth wide open. Good girl!
Mistress Mara – Scissored Sissy
My lady boy sucks my cock and gets fucked from behind, above, and scissor-style. We kiss, smearing our lipstick together.
Sent Away To Goddess Snow For Proper Sissy Training
Ellis’ step-mo has sent him away to his aunt’s, Goddess Alexandra Snow, for some proper training. His step-mo would like for him to become more feminine, and fortunately, her step-sis 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 step-mo, she will be the perfect fully feminized sissy girl.
Isabelle Deltore – Sissy Cock-Hole
Mistress Isabelle Deltore needs to show her sissy just what it’s like to be fucked by a big, fat cock before she sends him out to the real boys. She bends his tight ass over and slides her big, strap-on cock deep in his fuckhole. There is no escape for her sissy from a life filled with dick as Mistress Isabelle fills him up and gives him the ride of his life.
Isabelle Deltore – Sissy Tongue Bath
Mistress Isabelle Deltore loves to own sissy boys as she knows they are much more in-tuned with the female body. Sissies will always work their hardest to please their Mistress as they are never selfish when their cock is made useless by the form of strict chastity. Mistress Isabelle unlocks her sissy from its cage and put’s the bitch’s whore mouth to use. If her sissy does a proper job and makes his Mistress cum all over his face then a big, fat cock will be waiting to use the bitch boy’s fuck-hole!
Amadahy – Sissy Danni In Chastity Serves Princess In Bath
Goddess Amadahy loves to tease chastity slaves and rive them crazy with lust. In this clip she enjoys a bath making Danni wash her. Danni is further humiliated with his pantyhose he is made to wear. His chastity tube sticks out and he has a pink bow around his tube. Danni is always to wear a bimbo blonde wig. Amadahy calls her hot boyfriend and talks sexy with him. She nonchalant plays with Dannis chastity tube.
The Two Hole Sissy Slut Surprised By Ms And A Rubberguy
Sporting a nice black rubber strap-on, Mistress Susi is ready to use both her her sissy’s holes. Starting with the mouth, the sissy struggles to suck her cock deep enough. Soon after the German Dominatrix plows her sluts helpless ass but brought back the rubber guy to keep his mouth trained. Watch as Slut Candy takes Susi’s cock in his ass as he sucks the rubberboys cock too.
Feminized – Mistress Sissy Training
TS Mistress Marissa is training a new sissy. She plans on teaching the sissy how to be a proper woman, and that starts with looking the part. She has told sissy repeatedly “NO BOY CLOTHES IN HER HOUSE!”. Mistress strips off sissies offensive boy clothing and gives her a good spanking for disobeying strict orders. Once sissy looks the part it is time for dildo training. Mistress Marissa throat fucks the sissy with a pink dildo making her gag on the cock, no mercy for this slut in training. Next Mistress Marissa takes the dildo to sissy’s ass.
Subby Hubby Video Collection 1
Sissy maids & sissy boys – a sexually inadequate husband who accepts his wife’s pussy is her solely property and she alone decides which men she will fuck, husband denial, official sissy maids at Subby Hubby.
Girls Abuse Guys – Take Me Mistress
Johan has always fantasized about being fucked up the ass by a woman and today his mistress is going to take his anal virginity. She begins by stroking his dick to get him excited and then bends him over and inserts a finger into his bumhole. As he gets used to it she inserts a second finger and begins slowly finger fucking his ass. Johan is enjoying it now and his mistress flips him upside down on the sofa so his ass is sticking straight into the air, totally exposed to her. She takes a big rubber dildo and starts pushing it into his anus making him cry out as she does so. He takes it all and she starts fucking him with the dildo in several positions. To finish off her newly-created bitch, the mistress puts on her strapon and bends him over for a proper sissy boy ass-fucking.
Mae Ling – Cock-Whore Lessons
Miss Mae Ling’s slave has a very tight ass and needs to learn how to be a proper cock-whore for his Mistress. She makes her slut lube up her cock with his spit as she slides it in and out of his throat. When her cock is extra sloppy from fucking his mouth she takes it out and mercilessly pounds his tight hole. Her sissy boy just wants to please his Mistress’s dick and takes every inch no matter how rough and hard she gets. Miss Mae Ling doesn’t hold back as she makes sure her slut’s holes are loosened up and ready for the next size up!
Sofie Marie – Black Cock Stretching
Sofie Marie gets her tight little snatch stretched out by big black cock. She loves getting fucked in front of her captive sissy boy.
Marley Brinx – Born To Be Fucked
If there is one thing Mistress Marley believes is that all men were put on this planet to be fucked! She straps on her biggest black cock and pounds her sissy boys ass turning him into the fuck-hole he was born to be.
Eliza Ibarra – Step Mommy’s Demanding Feet
Eliza Ibarra has a very lucky sissy boy who is kept on his knees to always be close to her feet. Eliza has the little boy crawl to her with his balls pulled back extra tight so he can never stand up. He is expected to get every last inch of dirt off her heels before he is worthy of worshipping her bare naked soles. She makes him feel like a pathetic little wimp cowered below her as he tries to not make his Mommy angry.
Sensual Oriental Sadist – Vol. 3 – Goddess Qing
Goddess Qing is back for the third installment of Sensual Oriental Sadist. Here we see the Goddess at her best, making male slaves to pleasure each other after torturing them. Ass fucking helpless sissy boys all dressed in frills and training her useless maid to suck a big purple strap on.
Puma Swede – Nobody Fuck With Puma
Are you a powerful businessman by day and a perverted, little sissy boy by night? Do you need to be disciplined and shown your place by a cold-hearted mistress? We know that you want to be bossed around and told when and how to fuck. You want to be yelled at to lick shoes clean. Ice queen Puma Swede knows it, too. Watch as she humiliates her boss and treats him like the overpaid, disgusting pig that he is. This is how sissies like you should be treated, so watch and learn a thing or two.
Black Cock Cuckolding – Chloe Cherry
Chloe Cherry can barely fit this bulls big black cock inside her tight pink pussy. She gets stretched out than takes a load on her hungry beaver. Her sissy boy cleans up the explosion.
Alina Lopez – AnalGasms
Mistress Alina Lopez is slowly taking every last ounce of manhood away from her boy-toy without him even realizing it. He used to be such a tough, strong alpha man but now he is on his back like a bitch for his Mistress to do anything she pleases. Mistress Alina is about to show him the wonderful world of prostate orgasms but with a catch. What he doesn’t realize is this is now the only way he will be allowed to orgasm going forward. If there isn’t a great big, cock filling his ass up then he won’t be allowed to cum. He is no longer a man but just a sissy bitch who needs his holes filled for a release.
Cuckolding The Perverted Stepfather Mini-Movie
Cameron Canada realizes the boyfriend needs more sissy training, so it is back to walking in heels and learning to show off his body like a proper sissy slut. Cameron plans on whoring both of these bitches out and wants to make sure they can really take cock in their ass, so she orders both of them to fuck themselves in the ass with a dildo while she watches, masturbating to their humiliation. But these bitches can’t even fuck themselves right, so Cameron has to take over and fuck each of them herself. She truly enjoys turning the men in her life into pathetic little bitches. Now she won’t have to worry about her stepdad perving out on her anymore. Cameron has her stepfather and her boyfriend both kneel before her, naked and in chastity, so she can gloat about her power over them. Cameron orders her stepdad to lick her ass while her boyfriend worships her feet.
Jade Indica And Lexi Sindel – Panty Bitch Fucking
Lexi’s ex boyfriend has major sissy tendencies, he wears her panties and lingerie everyday when she leaves for work. Lexi Sindel brings Jade Indica over to show her what a crossdressing he has become. The girls laugh and humiliate him for getting so turned on wearing girls clothing, Next the girls fuck the crossdresser with strap-on’s to make him feel like a real woman.
Charlotte Sartre – Last Fuck As Man
Charlotte Sartre has her boyfriend, Lance Hart, bound to her bed. She dressed him in fishnets and heels. She sways her perfect ass back and forth as she tells him that she’s going to cut off his balls soon. This will be the last time he feels her amazing pussy on his cock. After this, she’s going to use him as her sissy whore. He’ll be eating a lot of cum, starting now with his last load, which he’s going to eat from her pussy after she’s done with him. He can try to stop from cumming to keep his balls longer, but it’s hopeless. She slaps him hard in the nuts while riding his cock. Even that won’t stop him from losing his last load inside her. When he finally empties his balls inside her, she smiles and sits on his face, making him lick her clean.
