Getting dolled-up for the shoot

Feminized guy gets his whole sissy sexcapade filmed on cam by a pervy girl
My Sissy Boyfriend - Getting dolled-up for the shoot - Christine , Lilly
The right make-up and a nice wig can make a pretty girl even out of a plain looking guy. The right lighting and a sexy outfit can make wonders, so now feminized Lilly looks like a model ready to pose for her inventive photographer. Christine takes on cam every moment of the sissy’s transformation and humiliation, ordering him around and making him swallow her fake cock before pushing it up his once virgin butthole.

Sissified and brutally dominated

Sissy guy goes for kinky strapon experiments with his dominative girlfriend
My Sissy Boyfriend - Sissified and brutally dominated - Beau , Joan
Beau would make a perfect domina with her passion for domination and sadistic inclination, while sissified Joan would make for a perfect victim for Beau’s kinky sex-experiments. Tied up to the chair Joan lets his mistress Beau put on make-up and check his swallowing ability. Then it is time for some leg worshipping and cock-sucking before Joan’s butt gets impaled on a stiff strap-on dick with merciless Beau taking the most from it.

One in the pink and one in the stink

Looking like a girl sissy shares a double dildo toy with a dark-haired babe
My Sissy Boyfriend - One in the pink and one in the stink - Michelle , Joan
When there is a dolled-up sissy, a private cocktail party can go wrong. Drinking Bruderschaft, deep French kisses, sultry caresses and a hidden double-dildo can lead to a steamy fuck-fest. Whatever made Michelle and Joan horny, a glass of wine, a red leather couch or Joan’s womanly looks, it also made them share one jelly toy. On making it sloppy in their mouths, they were ready to put to work their other holes.

Funky sissy maid services his mistress

Latex clad sissy getting his mouth and ass stretched to the limit by a lady
My Sissy Boyfriend - Funky sissy maid services his mistress - Valerie , Kelly
Clad in his funky PVC maid uniform with lacy gloves and a curly blonde wig sissy Kelly is tidying up the room when his mistress Valerie comes home. Valerie finds a black strap-on dildo under the pillow and decides to use it to discipline her naughty maid. She shoves her gloved hand into Kelly’s mouth and up the ass making sure there’s enough room for her rubber dick. Then she makes the sissy suck and ride on top of her fake cock.

Rich girl’s kinks revealed

Nasty sissy involves his girl into a strap-on session getting a gaping ass
My Sissy Boyfriend - Rich girl's kinks revealed - Busy , Melissa
Rich girls have lots of kinks, and gorgeous brunette Busy is no exception. However, you won’t guess that one of her kinks includes a big strap-on dildo and a sissy boyfriend. Busy isn’t willing to admit it at first, but Melissa is a master of negotiation, so soon this strap-on is put in place and Busy is ready to probe and poke Melissa’s hairy butt until it gets loose.

Unsuspecting sissy fucked like a slut

Wearing makeup and female undies sissy forced into a pervy strapon session
My Sissy Boyfriend - Unsuspecting sissy fucked like a slut - Gloria , Hannah
Gloria feels like trying something new, so she puts some make-up on her guy while he is asleep and then rolls him over sliding her moist finger into his cornhole. The feeling makes this sissy wide awake at once, so Gloria pushes him to the mirror telling him that from now on he is Hannah and has to master his cock-swallowing skills. At last she makes him wear women’s undies for a butt-busting session she has on mind.

Special requirements for a secretary job

Nasty sissy secretary blowing and riding a fake cock eager to get a job
My Sissy Boyfriend - Special requirements for a secretary job - Myra , Melissa
Willing to play a practical joke on a job applicant, Myra tells a guy she needs a female secretary and offers him to try on a special uniform. While he is changing into sexy women’s undies transforming into sissy sec Melissa, Myra attaches her handy strap-on. Later it turns out the sissy guy knows what he has to do. He worships Myra’s legs and sucks on the fake cock before thrusting his ass right on top of it. Will he get a job after he gets off?

Sissy’s kitchen adventures

Dressed as a female sissy approached from behind and nailed in the kitchen
My Sissy Boyfriend - Sissy's kitchen adventures - Whitney , Stephanie
Whitney spotted her sissified boyfriend going about household chores in the kitchen. He looked really impressive in his blonde wig and elegant outfit with matching high heels. Being in playful mood Whitney approached Stephanie from behind and hiked up the sissy’s skirt for a hard strap-on surprise she hid in her jeans. The naughty girl pierced the guy’s bum right by the cupboard before nailing him on the table ready to be pleased in return.