Archive for the “Trannie Stories” Category

Mistress Annabelle Vintage Crossdressing Videos

Lady Annabelle is a lifestyle dominatrix who trains and dominates her sissy slaves and makes them dress in genuine nylon stockings, retro-style underwear and heels.

Bringing a touch of real class to transvestite porn, Lady Annabelle indulges her passion for vintage styles of clothing and underwear, forcing her sissy slaves to dress up in female garments, and subjecting them to punishments using whips, canes, dildos and fucking machines.

Lady Annabelle is the embodiment of female perfection, and her beauty alone will have you begging at her feet to become one of her devotees. She even encourages those willing to submit to her commands to contact her for personal training.

Meanwhile you can watch her weekly videos and get a taste of what you can expect when you enter the world of Lady Annabelle at Vintage Crossdressing, where all your crossdressing dreams cum true…

Vintage Crossdressing With Lady Annabelle

Click here to enter Lady Annabelle’s World Of Vintage Crossdressing

 

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Tranny Slut in Stockings Fucks Her Ass With Huge Dildos At Kims Anal Heaven
Sometimes it only takes a soft pair of gorgeous stockings to really get this tranny cock of mine feeling nice and hard. The moment I put on my stockings, I feel my body start to shiver with excitement, and my tranny dick just goes so hard.

All I want to do is play all day long in my sexy stockings, teasing my cock to the point of cumming. But I’m not going to waste this opportunity to get my monster dildo’s out, and really go to town on this tight ass of mine.

I’m really starting to get so fucking horny now, and my fingers claw over these slutty stockings as I feel the whore in me wanting some cock.

There’s only one thing for it now, I’m going to have to go to my toy collection and pull out the biggest one I can find, then lube it up slowly and ease it into my tranny ass.

I want my body to shudder and shake as I fuck myself up the ass and take it like a dirty whore. Then I want to wank my clitty cock and shoot a hot load of sperm all over myself and just lay back completely satisfied.

Can you think of a more perfect way to spend the day? I know I can’t!

CLICK HERE TO SEE MORE OF KIM FUCKING HER ASS WITH HUGE DILDOS

 

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Tranny Sluts Fucked By Female In Threesome Orgy At Zoe Fuckpuppet

I recently invited a new crossdresser and his girlfriend to join me for a threeway fuck party and had a fucking good time!

He’s not really a tranny girl, but more a boy who gets very hot when he’s forced to dress up.

He wanted to be forced to suck my cock, and then to watch while I use his girlfriend’s pretty body for my own pleasure.

I made him dress in stockings and heels, to help him feel a little more girly while he sucked my huge tranny cock.

It was his first time tasting tranny dick, which he sucked enthusiastically, licking and swallowing my throbbing cock like a proper whore as he prepped me for the climax of our naughty, little rendezvous.

His girlfriend fucked him up the ass with her strapon cock, as I fucked and filled his willing mouth with the fullness of my tranny prick.

Then I mounted his girlfriend, and we kissed and grabbed at each other’s tits, moaning against each other as we fucked, two sluts craving a hard cum! We all got off so good that day!

SEE MORE OF MY SEXUAL ADVENTURE WITH GUYS, GIRLS AND TGIRLS HERE AT ZOE FUCKPUPPET

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Mrs Lovings Wanking Off Two Crossdressers In Stockings Suspenders and Panties Video

If you watch this movie carefully, you’ll see Mrs Loving gets very excited and turned on when she plays with her sissies, Allyson and Monika.

She begins by telling them to kiss and feel each other up, and soon their cocks form big bulges in their dresses that Mrs Loving must explore and expose.

Mrs Loving watches, instructs and guides her sissies as they explore oral sex and suck each others stiff cocks in turn.

Mrs Loving gets so excited seeing them pleasure each other, she instructs them to worship her panty crotch, making them and sniff and lick her womanhood through the damp cotton of her panties.

While she is sucking on Monika’s clitty cock, she jerks off Allyson who suddenly cums due to all the erotic excitement of the situation.

Next, Mrs Loving makes her sissies kneel and bend while she prepares their arses with her fingers, and then fucks one of her sissies from behind with her strapon.

After the fucking, Mrs Loving sits on the couch with their stockinged legs draped over hers, then she begins the long slow milking of their cocks that releases more sissy cream than you can imagine.

CLICK HERE TO SEE MRS LOVING MILKING HER SISSIES IN THIS VIDEO

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Pantyhose crossdressers wanking each others cocks video

Only another crossdresser knows how to satisfy your need to dress up in nylon pantyhose and have wild pantyhose sex. Which is why Monika and Allyson got together for a lustful afternoon of mutual crossdressing, and uninhibited pantyhose sex as seen in this video at Panty Club For Men.

Crossdresser’s Monika and Allyson love dressing up in dresses, lingerie and fabulous nylon pantyhose, and became very aroused while helping each other to dress up in their pretty dresses and panties.

They were soon both sporting huge erections which bulged at the front of their tight pantyhoses, which elicited them to begin touching each others cocks through the nylon screen of their hose.

They soon found themselves in a close pantyhose embrace, masturbating each other through their sexy hose, and rubbing their cocks together which made them slippery with girlie pre-cum.

Pantyhose crossdressers mutual wanking togetherand spunking in nylon hose video

Pulling their pantyhose down to their thighs, they got into a 69 position with stretched pantyhose gussets close to each others faces, indulging in an orgy of shared cock sucking and ball licking.

They mutually masturbated each other with hands inside the other’s hose, then they finished by stroking their own cocks and shooting thick white cum through the nylon mesh of their sexy pantyhose.

CLICK HERE TO SEE MORE CROSSDRESSING UPDATES AT PANTY CLUB FOR MEN

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Tranny Slut Kim In Black Stockings Stuffing Two Dildos Up Her Tranny Pussy

There really is something very sexy about black lingerie, isn’t there? I’m a big fan of beautiful black nylon, and I love they way these patterned stockings cling to my gorgeous legs, they look simply fantastic!

I have this fan who wanted to see me wanking in my stockings, so I started off slowly with just a few teasing shots of me masturbating and spreading my gorgeous long legs open.

The thought of this filthy fan yanking his erect shaft, made me feel the need to have my arse stretched wide open, and I fantasized about having an over-sized cock deep inside my ass.

Being the total anal slut that I am, I lubed up my favourite massive dildo and rammed it up inside my ass, and straight away my tranny cock started dripping with pre-cum!

I’m such a greedy girl, the thought of having two cocks in my ass seemed like my idea of heaven. So I grabbed another dildo and stuffed it up my tranny fuck hole, stretching my anal pussy to accommodate this lovely second cock which fit so snugly up my arse.

I knew it wouldn’t be long until my cock shot my warm cum.. I’m such a horny tranny slut, I hope this fan realizes how lucky he is!

CLICK HERE TO SEE MORE OF KIM FUCKING HER ASS WITH HUGE DILDOS

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Strapon Jane Fucks Stocking Transvestite Up The Ass

I get all kinds of transvestites and crossdressers of all shapes and sizes visiting me for a good ass fucking.  So it was nice to get my hands on this curvy tranny slut, as I hadn’t had a fuller figured tranny for a while.

It turned out that this tranny whore was a real filthy girl who liked a little bit of BDSM. So I immediately popped her in the cage and tormented her by pushing my strapon cock through the bars, letting her know exactly what was going to happen to that tranny ass of hers.

This transvestite slut begged and moaned for me to release her, as she was so eager to get her tranny ass fucked by my monster strapon.

I bent that tgirl fuck toy over and spread her big ass wide open, then filled her tranny arse with what she’d been craving for… My 10 inch strapon!

This tranny bitch yelped like a little dog at first, but then that soon turned into loud moans of pleasure as I stretched and widened her tranny fuck hole with my big erect cock!

What a filthy crossdresser fuck slut she tuned out to be, and after thoroughly I’d punished her tranny arse she left smiling. Well, smiling and limping anyway.

CLICK HERE TO SEE JANE FUCKING MORE TRANNY SLUTS WITH HER STRAPON

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mrsloving milks a sissy cock in panties until it spurts cum video

Sissy Lauren loves looking up women’s skirts to get a peek at what they are wearing. Sissy gets hard at the sight of damp panties, stockings tops and garterbelts, in fact all the secret things that ladies wear under their clothes.

With this in mind Mrs Loving makes Lauren lay down on the bench, and lifts her skirt so she she can straddle Lauren’s head.

‘Get a good look at my panties,’ says Mrs Loving, as she lowers herself over Lauren’s face and gives her a perfect view of her damp knickers.

‘Smell my scent, sissy’, Mrs Loving commands, as she moves her nylon panty gusset over Lauren’s nose. ‘That’s it, inhale my womanly fragrance!’

Sitting on sissy’s face, Mrs Loving pulls Lauren’s panties down to expose her clitty hard cock and takes it in her firm grip.

Rubbing her moist panty gusset over Lauren’s nose, Mrs Loving begins the milking with her expert hands.

Lauren licks the damp gusset of Mrs Loving’s panties, as mistress tugs and teases the cum out of her helpless sissy plaything.

Pumping Lauren’s cock until she spurts her sissy cream, Mrs Loving smiles as she catches it in her hand so sissy can lick it all off!

CLICK HERE TO SEE MRS LOVING MASTURBATING HER GIRLIE SISSY BOYS

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CROSSDRESSING SLUTS IN STOCKINGS AND SUSPENDERS SUCKING AND FUCKING WITH STRAPON THREESOME ORGY

Mistress Helga got herself two naughty little crossdressers to play with the other day, and made them suck each other off while she fucked their tranny whore arses.

Dressed in their favorite slutty clothes, one in an open-bottom girdle and nylons, the other in sissy pink satin, stockings and suspenders, they both looked ready for  a good fucking.

This horny pair loved being ordered about, told what what to do, and when to do it, and Mistress Helga made sure they both sucked each others hard tranny cocks in turn.

Mistress Helga then fucked their tight tgirl assholes, making sure one tranny whore gave oral service to her friend, while she took the other one up the ass with her strapon.

Mistress plunged her cock into the first crossdresser’s arse, stretching her tranny fuck hole to the limit, as the little tranny bitch sucked enthusiastically on the others throbbing clitty cock.

These tgirl sluts sure learned who was in charge, and they took everything Mistress Helga gave them, loving every second of it as their slutty mouths and arses were filled with her monster strapon cock.

CLICK HERE TO SEE MORE OF MISTRESS HELGA AND HER SUBMISSIVE TRANNY SLUTS

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lucy may bound bondage transvestite crossdresser wanking in suspenders and stockings

Every time I dress up in my tranny slut clothes, my cock gets so erect and I can’t stop giving it a good tug. This time my master caught me at it, and decided it was time I was punished.

I’ve been such a dirty crossdresser slut lately, dressing up in my stockings, panties and body-shaper with the cupped bra. My cock gets so hard in my panties when I look at myself in the mirror, I like to stroke it as my erection strains against the material of my knickers.

All the more reason for my master to punish me for being a naughty tranny whore, so he’s decided to tie me up so I can’t play with myself.

He ties my hand to a top beam and makes me look at my tranny self all dressed up in the mirror. My cock gets stiff in my panties, and I can’t even spread my legs. I’m aching to get my cock out and be a filthy transvestite slut again, so he lets my hands free.

I release my cock from the tight confinement of my panties and give it a good wank. I think he secretly enjoys seeing me wanking as I stand in my stockings and panties and stroke my rod, gripping the shaft in my fist as I tug myself off and watch me release my tranny cum.

CLICK HERE TO SEE MORE OF LUCI MAY’S UPDATES

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strapon-sex-stockings-transvestite

My reputation as a dominant precedes me and I recently met this transvestite slut at a fetish club which was hosting a tranny evening. This little whore approached me looking for a fucking and begged me to take her home and ream her arse with my strapon.

I got her home as soon as possible where she posed for me, bending over in her tranny stockings and showing off her round tgirl tush like a little tart.

I bent that little slut over and pulled her panties down, grabbing her tranny cock and milking it with squeezing motions with my hand.

Then I made her suck on my latex cock, pushing her head down and she greedily sucked on my black rubber penis like a filthy whore.

I lubed up my massive strapon cock, and making her lie on her side I pushed it into her cock hungry ass. She was backing up onto me, her ass eager for more rubber cock as I forced my latex dong up her tranny fuck hole, stretching it wide with every thrust.

I gave that slut everything she wanted and more, finally jerking her off with that latex cock fully inserted up her butt hole.

SEE MORE OF MISTRESS JANE FUCKING CROSSDRESSERS AND TRANSVESTITES

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luci may

Transvestite Lucy May Bound And Wanked Off By Her Mistress

Lucy has a very imaginative mistress who thinks up some kinky ways to punish Lucy’s transvestite cock.

She wraps Luci up in a garbage bag and binds her hands, telling her she is ‘going to treated like the trashy tgirl’. Her transvestite cock now belongs to her Mistress and is hers to do as she pleases.

With her hands tied, Lucy just lays back on the sofa and waits for her Mistress to decide what to do next.

Luci’s transvestite rod was so hard, her Mistress she could see the bulge beneath the tight layers of plastic wrapped around her hips and thighs.

Her Mistress rips away the plastic bag and starts to squeeze her tranny cock. It drives Luci wild and her Mistress wanks her cock even faster, calling her a tranny slut.

Lucy just smiles as she knew she was so close to cumming and she didn’t want her Mistress to stop.

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Karen TV Slut Fucking Her Tight Ass With Big Red Dildo

Karen TV Slut Fucking Her Tight Ass With Big Red Dildo

Dressed in her beige nylon stockings, Karen TV Slut fucks her tight trannie ass with a big red dildo.

After a long day at work as a receptionist, I couldn’t wait to get home, dress up in my slutty, transvestite office clothes and sexy high heels, and relax.

Wearing my beige nylon stockings, white suspender belt and pink ‘fuck me’ heels, made my crossdresser cock so stiff. I pranced around my apartment in my slutty heels, but my feet felt tired and need a nice long foot rub.

Laying down on my bed I massaged my heels and ankles slowly, but firmly, and while rubbing my tried feet through the nylon I felt my cock getting hard through my knickers.

I needed a cock up my arse, so I pulled out my favorite dildo from my special toy draw, and forced it into my mouth to make it nice and wet. I teased my anus with it, imagining it was a cock wanting to enter, and then pushed the tip of the dildo up my tight, tranny tush.

I worked that dildo up my hungry ass and felt it stretch my dirty fuck hole, sometimes sticking my fingers up there, then sliding the dildo back up.  Opening my stockinged legs wide like the dirty tranny slut that I am, I fucked my arse with that cock until I shot my hot tranny jizz all over my stomach.


Karen is a slut, a slut that likes to fuck women and other tgirls! It’s just pure slutty pleasure for this tranny slut!

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This pretty little sissy maid caught me on a day I was feeling very horny. I’d gone hours without being fucked, and this little sissy doll turned up.

First I pulled this femme cd fuck dolls frilly little skirt up, and made her show off her panty-covered ass. Then I whacked her tight, round cheeks with my riding crop, until she had lots of pretty marks.

I pushed her down on the the floor, onto her knees, and I showed her what she’d done to my panty-covered cock. It was all big and swollen, and it needed some sissy maid attention.

She licked my cock with her sissy mouth and sucked on my shaft with her red, painted lips. I forced her to suck me deeper and deeper until I finally blasted my sperm into her mouth, and all over her pretty, subservient face.

Next I forced this tranny whore to bend over the toilet and I pulled her knickers down. I instructed her to wank her cock and as she was rubbing herself off, she slipped a dirty, little finger up her own ass!

As she finger fucked her pink hole she started to cum all over the place. Little sissy whores have to clean up their own messes, of course!

Karen is a TV slut, who likes to suck and fuck! Come see her plough her way through women and tranny sluts who require kinky fun! It’s just pure slutty pleasure for Karen TV Slut.

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