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StrapOnSessions.com Toby Toby came over telling the Strap On Princess that he likes to bottom AND TOP. She quickly reminds him there will be no topping from the bottom tonight! Strap On Princess is in total control of his mouth and his ass hole. She starts off by lubing up her hands and stuffing her fist up his big ass bung-hole and then breaking out the anal toys. Glass dildos, prostate massagers, and more fingers get plunged deep into Toby's man pussy until the Princess is ready to fuck! With her giant black strap on she pounds Toby rough up the poop shoot and then makes him turn around to suck off the ass foam it creates! The Strap On Princess loves this big fat baby and lays him down to fuck his fatty booty over and over again while he strokes his tiny wiener. When the Princess becomes bored of this, Toby cums all over himself and she makes him eat it!

Video Length: 20:09 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com David David came to the Strap On Princess wearing a body suit and panty hose, which already made the Princess laugh. She tosses him up on the table and discovers he is also wearing a chastity cage around his tiny cock. The princess becomes ENRAGED when David tells her he cant get hard or cum for her. Some other dominatrix has the key to this infernal device and this is unacceptable. The Strap On Princess decides to give this peasant some extra abuse by wrapping him up in a Straight Jacket! She whips out her big black fake dick and goes to town plunging it deep into David's "virgin" ass hole. She makes him taste his ass juice quickly before stuffing it back up his dirt shoot! Out of nowhere David starts to squeal like a piggy! This lightens the mood and the Princess is happy happy. Watch her peg this lunatic hard and fast and choke him with her big ass Strap On! She sends him home with both holes sore and arms still wrapped up in a Straight Jacket covered in his own juices.

Video Length: 20:47 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com Griffin Ben from Dover came over to get his ass rammed hard by some girly cock tonight! The lovely Strap On Princess and her cute friend the Duchess of StrapOn are more than willing to stuff this peasant's holes FULL! Watch Ben gag on their big fake dicks and get thrown onto the bed to receive more tough love deep up his hairy ass hole! They put his sissy ass in pantyhose and give him some pretty pretty lipstick. He cries out "I'm a sissy!" while his holes are being violated with mean girly cock-meat, and these two peggers giggle with glee! When they're done fucking Ben every which way they throw him on the floor and boot his slave ass out the house!

Video Length: 24:16 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com Justin Justin and Alissa are a submissive couple that love to be told what to do, and what to shove up their ass! They definitely came to the right place today. The Strap On Princess was very happy to oblige their but hole submission fantasies. The Princess wastes no time and immediately places a ball gag into Alissa's mouth to ensure no bitch back talk! Justin encourages her while she gets boned in the ass by the Princesses toys, and then her BIG BLACK DICK! When she gets bored of Alissa's tight asshole the Princess moves onto fucking Justin's mouth and his hairier looser rectum! She pegs his but hole so good he cries out "Fuck My Pussy!" Soon she lines them up in an anal train! The princess stuffs her huge black fake cock into Justin's shit shoot while he stuffs his tiny cock into Alissa's dirt box. After some incredible ass fucking, and being slapped around by the Princess, Justin blows his load deep into Alissa's cornhole and everyone is pleased. The Strap on Princess will definitely see these two submissive lovers again.

Video Length: 21:00 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com Bruce Bruce is a biker dude who loves to have things in his ass. He started long ago by shoving his finger up his but-hole, and soon it was onto bigger and better things. Today Bruce comes by for some good ol fashioned pegging! The Strap On Princess and her new apprentice Dixie cant wait to get started. They yank on his beard and stuff their plastic cocks down his throat, making him gag. Then they throw him up on the bed and start fucking his hairy man ass! Dixie fucks his mouth with her little pink dildo and the Strap On Princess fucks his ass with a big black dildo! Bruce is a grade A spit-roast to these hungry fake dick wielders. Dixie then gives Bruce a real treat, she can lactate at will and squirts him in the fucking face with her tit milk. Dixie sprays her momma juice all over Bruce's beard, head, back, and yes even directly into his mouth. Bruce leaves today with a stretched out throat and anus, and doused in nasty wet breast milk. It is a night he wont soon forget.

Video Length: 19:30 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com Jim Ms. Chloey is 19 and never used a strapon before, so I decided it was time. I called fat boy Jim over to get pegged. I take control of the situation immediately getting fatboy sissy baby naked and we start fucking his ass! I have Ms. Chloey fuck his face and she makes him gag on her cock very well. As I fuck his ass this old dirty fuck whines like a baby. I find it funny and ironic that he is the oldest person in the room but whines like a baby. Bossing fat boy around amuses Ms. Chloey and I so we laugh in his face. I make him bend over and smell the flowers, we peg him and I whip his balls till they turn red! We have our fun teaching this big old baby who is boss. When we are bored with him I make him crawl to the bathroom to clean up.

Video Length: 23:00 Minutes Download -  FULL Video Cost: 5 Tokens

StrapOnSessions.com Griffin I met this kinky couple at a sex toy shop. Mistress Sara and I quickly struck up a conversation about dominating men in the bedroom, and just how amazing it is! I invited her and her bitch boy Griffin over for some Strap On fun! We quickly got Griffin naked showing off his hairy little body, and extra furry but hole! Mistress Sara and I take turns pegging his tight ass with our fake dicks. She used a small anal toy called a "feeldo" but i stuck with my favorite Big Black Girly Cock. We filled his manhole over and over, as I was having a fantasy about fucking a "Hairy Justin Beiber" in the ass! Finally we let him shoot his pathetic cum all over our plastic cocks and made him eat it off our cocks!

Video Length: 27:03 Minutes Download -  FULL Video Cost: 6 Tokens

StrapOnSessions.com Kevin Kevin is a web site member of StrapOnSessions.com. He emailed me begging me to turn him into a real girl. So I start by introducing him to Mistress Tosha and we start right away by applying some cute makeup on him. Kevin looks good in a bra, panties, and red lip stick. We both smear his red lip stick while he sucks our strapons. He looks so pretty and feminine getting pegged with his pink dress on. We stretched out his pussy ass real good. When his ass started to bleed, we showed him how it feels to be a girl by shoving a tampon up there!

Video Length: 25:03 Minutes Download -  FULL Video Cost: 6 Tokens

StrapOnSessions.com Roger I just showed my HOT girlfriend Ms Mila how to use a Strapon for the first time! She loved dominating Roger and pegging his tight ass! Roger is a tan construction worker that has had that ass tapped before. We turned him into our meat puppet by taking turns fisting him. He came on our girlie cocks and then he licked them both clean. Roger really looks good with cum on his chin, do you think his coworkers would agree?!

Video Length: 26:54 Minutes Download -  FULL Video Cost: 6 Tokens