My Sissy Boyfriend Incredible crossdressers take part in hot female domination scenes from My Sissy Boyfriend.

Corporate punishment for the intruder

12.24.2010

Dolled-up sissy getting his throat and butt cleared right in the office
My Sissy Boyfriend - Corporate punishment for the intruder - Mary , Elisabeth
Mary was more than surprised to find a cross-dressed guy at her working place after she went out to make herself a cup of coffee. Pissed off with a cheeky red-haired sissy she pored her coffee right onto his yellow blouse. Still Mary was willing to punish feminized Elisabeth even more, so she grabbed her handy pink strap-on and bent down the intruder pushing her tool up to the hilt into his rear and cleaning his throat too.

One unforgettable experience

12.24.2010

Sissified guy swaps roles with his spoilt girl getting fucked as a female
My Sissy Boyfriend - One unforgettable experience - Selma , Kathleen
Selma is a spoilt rich girl and she can do whatever she pleases with her older acquaintance. Today she’s decided to turn him into sissy Kathleen, so she applies some make-up and dresses him into a long gown along with black lacy stockings and pumps. Then she takes out her black strap-on and fits it on while stripping to her undies. Now Selma is ready to give her sissy friend an oral-anal lesson that he won’t ever forget.

Red hot sissy training

12.24.2010

Submissive sissy disciplined and banged up the brown by his spoilt girl
My Sissy Boyfriend - Red hot sissy training - Chris , Dennis
On changing into a scarlet dress with black stockings and letting Chris fasten his collar and cuffs, Dennis turns into a cute submissive sissy. His spoilt girlfriend teases him with a strap-on dildo and makes him obey and go down using a bright red flogger. So watch Dennis readily putting his ass up in the air for some proper flogging and strap-on fucking after showing his outstanding oral skills.

Kept on a leash and treated like a femme

12.24.2010

Obedient sissy guy goes for some raw play getting his mouth and bum filled
My Sissy Boyfriend - Kept on a leash and treated like a femme - Michelle , Hannah
What makes a good sissy? Michelle knows how to make a good sissy out of her boyfriend. You need a wig, a nice dress and a pair of stockings and high heels and here you are – meet our girl Hannah. What’s more, a good sissy is an obedient sissy, so a collar with a leash and a crop will come in handy. Now sissy Hannah will obediently take any punishment and humiliation dished out by kinky Michelle even if it’s a toe or a strap-on shoved up the ass.

Obedient sissy gets rewarded

12.24.2010

Kinky sissy puts on a wig and female clothes eager for some strap-on treat
My Sissy Boyfriend - Obedient sissy gets rewarded - Teonna , Veronica
Teonna knows what kind of treatment her sissified boyfriend needs. Armed with a strap-on she makes him worship and pleasure her before he can get even a taste of her extra equipment. Finally getting fully dressed sissy Veronica gives proper head and spreads ass cheeks for the full-on hardcore anal. The raunchy sissy takes it from behind and jumps on top thrusting his ass on this rigid fake cock.

Pajama party went wrong

12.24.2010

Drunken sissy pleasures a babe eager for the feel of a strapon up his butt
My Sissy Boyfriend - Pajama party went wrong - Emily , Hilary
Emily and Hilary were having a pajama party, and after a few glasses of wine and drinking Bruderschaft they got to deep mouth-to-mouth kisses and the party went out of control a bit. When blonde sissy Hilary changed his blue nighty for a red-n-black stripy dress, the things got even hotter. Emily took out her massive black strap-on toy and made Hilary beg for the feel of it while pleasuring her in every which way.

Fisted and strap-on fucked sissy

12.24.2010

Fiery sissy guy gets his lubed asshole fisted and impaled on a hard dildo
My Sissy Boyfriend - Fisted and strap-on fucked sissy - Ellie , Anna
Gorgeous redhead Ellie finds a strap-on dildo on the shelf and can’t help testing it with her pussy. When a sissy guy comes in wearing a bright stripy dress and a red wig while eager for some strap-on treat, the girl makes him open up his ass first. She puts on gloves, applies some lube and starts fisting sissy Anna’s butt until it gets loose enough for her rubber dick. Then Ellie makes Anna swallow this strap-on cock and impale his bum on it.

Coffee and strap-on for breakfast

12.24.2010

Turned into a girl sissy gives head and thrusts his behind on a rubber cock
My Sissy Boyfriend - Coffee and strap-on for breakfast - Sarah , Stephanie
Sarah brings her cross-dressed lover breakfast and offers him to change his sexy yellow sleepwear for some smart outfit. She helps her sissy toy Stephanie into black suspender tights and takes out a pink strap-on dildo from the bedside-table. Sarah makes this unwilling sissy blow the fake cock like a good girl, then she orders him to fondle her nipples before she can start working his nicely lubed asshole.