More Trannie Trouble takes you far beyond your most depraved erotic fantasies with 1,5 hours of bi-sexual, fetish, cross-dressing, femdom, strapon and group action. Men dress like women and fuck other dudes as well as nice-looking chicks who love role-playing games and hardcore group sex. Women take over and administer painful punishments to get their lovers ready for the kinkiest sex ever. The action is out of control and you never know what’s gonna happen in the next episode.

 Madame Caramel is a heavy black mistress who loves nylons, latex outfits and humble white slaves. She turned her crib into a domination facility packed with all the tools and accessories she needs in her depraved fetish games. She can be a pretty nurse, a dirty doxy, a evil teacher or a boss making her slaves cross-dress, suck dicks, adore her feet and do other kinky stuff, then punishing them with spanking, whipping, stretching, hot-waxing and other painful procedures.

Aiden uses Natali’s tied down body as her fuck doll, fucking the tied on strapon. Then she ties Natali on her stomache and inserts a butt hook. She teases Natali with the vibrator and punishes her feet and ass with the crop. Aiden expects big orgasms from her students, so she Aiden fucks Natali hard with the strapon. Interview included.

View this Bondage Orgasm gallery!

Natali is sent an invitation to a special private school, not knowing exactly what type of school it really is. Mistress Aiden Starr captures Natali and shows her what higher education is all about: Severe Bondage, Hot Wax, Electricity, Multiple Forced Orgasms, and Flogging. Natali can’t endure so many orgasms but they just keep cumming. She is forced to lick Aiden’s pussy to avoid more pain, but Aiden sadistically ties her up again and sucks and fucks a strapon attached to Natali’s bound body. More in part 2.

View more here

Leggy blonde, Carolyn Reece, plays Agent 34D on a secret mission. Her assignment: to capture Jelena Jensen and take her back to the agency. Only, Agent DD had tapped her phone and takes advantage of Carolyn and the unresolved issues of their past. She wants to convince Carolyn to go back to how things used to be between them. She ties her up and makes her wear the dildo gag and fuck her with it. Then for old times sake, she gets out her favorite strapon: Buck and fucks Carolyn just the way she likes it: tied up! BTS and Interview included. Full Story.

View more here

April is now tied stretched over backward painfully on the bondage horse for more teasing and torment. Natali tells her to beg for her pussy to be licked, while she bites her nipples. Natali bites and sucks her pussy lips then takes her into the dungeon to be tied spread eagle to the wood frame. She is tormented with the pin wheel, then told to beg for her strapon. After she’s happy with April’s submission, she dons the strapon and fucks her with it until she cums. Interview and BTS included.

View more here

Click here to view the full gallery

This dirty, sissy whore kept making shy eyes at me during a fetish convention, so it’s no wonder that I brought this little tease back to my place for some hardcore fun. It must have been the big, black bulge underneath my skirt that caught his eye, because as soon as we were back at my flat, he was down on his knees in front of me. He begged and whimpered like a girl at my underwear, hungry for the taste of my huge strapon. Come on, you know me? Do I ever let my tgirl fuck sluts get off that easily?

I stripped my new sissy toy, put a hot black gimp mask over his pretty face, and began the long process of breaking my new “girl” in. He whimpered as I grabbed his shaft and balls with one hand, and tugged hard on his hip with the other. My massive, black organ pulsed against his tender, little ass. I wanted to ravage this fresh piece of sissy meat, but something just wasn’t right! I always want the first time to be special for my new sissy sluts.

Yes, that’s it! Not enough pink to keep my big strap-on rock solid. A frilly one piece dress makes this new tgirl feel pretty and vulnerable. I pull her knickers to the side and torture her wet, dripping cock. Oh, she’s ready now, and I feel the sudden urge to bury my big black strapon cock right up her fuck toy arse.

Join Strapon Jane Today
See the most dominant woman on the web using her strapon like only she knows how to do. Strapon Jane is ready to give out the punishment!

Click here to view the full gallery

I’d like to introduce you to my new horny dominatrix friend, Elle. She’s as much as a bitch as i am when it comes to laying out some hardcore punishment. Her big round ass and strong legs give her plenty of power when she’s thrusting away at some  tranny sluts pussy.

We like to double up on our victims. Two dominant femdom is ready to go, our huge strapons just waiting between our legs and always ready for a pussy or sexy behind. One of us will be ploughing into our victims slutty mouth while the other penetrating a soaking wet tush and pussy. It’s time for us to find a new play thing.

Join Strapon Jane Today
See the most dominant woman on the web using her strapon like only she knows how to do. Strapon Jane is ready to give out the punishment!

Click here to view the full gallery

I had to get some of my deviant and dominant urges satisfied today so i looked through my list of crossdresser sluts and saw the number of a particually horny crossdresser slut i hadn’t banged in a long time and gave this little tranny fuck toy a call and told her to come and see me now. “Have i been bad, mistress?”. she wimpered at me. “Always!” i replied. I put on some horny lingerie and heels, along with my massive strapon cock and waited for my transvestite slut to arrive.

I paced up and down, holding this big strapon cock in my hands. My fingers toyed with the head of this 10 inch long rubber cock. Large and wide, ready to fuck my crossdresser whores mouth and tush, my horny wench is getting punished the moment she arrives. My door bell rings and i go and welcome my guest. I opened the door and saw a sexy, blonde, transvestite fuck toy waiting and ready.

A long coat covering her body but i could see some nasty nylons and sexy high heels underneath it. I grabbed her by the hair and dragged her up to my bedroom. I pushed my filthy crossdresser onto the bed and forced my massive strapon cock into her mouth. I don’t waste time punishing these filthy sluts. I rubbed my firm body all over hers, feeling her hard crossdresser rodpulsating. She begged me to let her slide it between my big tits and seeing as she took my huge strapon deep inside her slutty mouth, i let her. I should punish this one more often.

Join Strapon Jane Today
See the most dominant woman on the web using her strapon like only she knows how to do. Strapon Jane is ready to give out the punishment!

Click here to view the full gallery

I get many requests from my fans to fuck them with my big strapon and i try to oblige as often as possible. I beg and groan like little crossdresser sluts and it makes me feel powerful and sexy. This horny little tattoo’d transvestite fuck toy sent me some pictures and a begging letter and i wanted her to feel what being punished was really like.

I’ve got a nice little dungeon set up in my basement so i invited her over for her punishment. She gladly obliged and it wasn’t long before i had this little tgirl whore on her knees and taking one of my MONSTER strapon cocks deep into her filthy little mouth. Hard and fast is the only way to punish this crossdresser whore and that’s exaclty what i did.

After making the tgirl wench gag on my strapon, i got right behind her and started working on her tight asshole. Pushing my strapon in slowly at first and then thundering it in shortly after, i give this crossdresser whores behind the workout of a life time and no doubt i’ll recieve another begging letter later this week.

Join Strapon Jane Today
See the most dominant woman on the web using her strapon like only she knows how to do. Strapon Jane is ready to give out the punishment!