Jul 212012

Beautiful Sissy Boy Fucked In Stockings By His Girfriend Up The Ass With A Strap-On Dildo In Strapon Sissies Video

Denise is very understanding about her boyfriend’s need to crossdress and they love to play sexy games where they dress up together.

One Sunday afternoon they were dressed up in vintage attire resembling two respectable ladies in dresses attending a tea party, when her sissy boyfriend produced a strap-on dildo which he wanted Denise to wear and take him up the ass.

Denise stripped out of her dress and strapped on the dildo, and sissy got down on his knees and wrapping a gloved hand around the shaft he took the thick cock in his mouth sucked on it hard.

Denise then made him kneel on the couch and lifted his green-n-white gown to reveal he was wearing a pair of elegant gartered nylon stockings. She then pulled down his panties to leave them stretched around his thighs, and sticking out the tip of her wet tongue she rimmed the puckered ring of his ass in preparation for what was coming next.

Getting behind her sissy slut she grabbed the cheeks his suspendered ass as she eased the thick cock up the tight ring of his sissy butthole. Thrusting her hips forward she felt the cock gradually slip inside her boyfriend’s shitter as his sphincter relaxed to allow deeper penetration.

Denise then pushed her sissy boyfriend forward on the couch and laying on top she began to ride his ass with increasing thrusts. As she pumped that thick, hard cock, ever deeper inside his sissy cunt, her boyfriend lay there submissively and moaned with pleasure at being fucked like a girl.


Jul 122012

Mrs Lovings Mature Female Fucking Sissy Crossdresser In Stockings Up Ass And Wanking Cock To Orgasm Video

You may recall Sissy Lauren had been sent to Mrs Lovings because she had been caught wearing and wanking in her auntie’s panties. It was her first time being fully dressed as a sissy girl, and she was just so excited that day the session ended with Sissy Lauren squirting her sissy cream into her panties.

Sissy Lauren has learned to become much more feminine and docile, and Mrs Lovings felt she was ready for further training as a sissy maid, which can be quite an intense experience.

Mrs Lovings requires that all her maids learn to serve dinner and cocktails, while staying focused on the task at hand as she shows off their stiff clitties to her invited girlfriends.

She tests them by stroking their the sensitive parts of their sissy cocks while she making them pour out wine with a very steady hand. Some manage to perform their tasks, while others get too excited and require punishment.

Mrs Lovings likes to put silicone cock rings round the base of their testicles and penis, and loves how it makes their sissy clitties extra hard and throbbing, and their girly balls look tight and swollen.

For the most part Sissy Lauren did rather well in her test, and she was rewarded by Mrs Lovings who wanked off Lauren’s cock while she fucked her sissy maid up the ass!

Sissy Lauren was so overjoyed while being fucked by her mistress, she thanked her over and over again as she felt herself cumming fast and hard while being fucked in the swing.


Sep 012010

mrs lovings fucking sissy crossdresser up the ass

Sissy Christine’s pussy is lubed up by Mrs Loving’s finger, and she slides her fingers right into sissys ass, opening her up and getting her ready for her strap on cock. Mrs Loving makes Sissy Christine get into her fucking sling, and Christine’s legs are spread wide open and restrained so she has access to her sissy pussy.

Now that Sissy Christine’s ass is ready for Mrs Loving, she gets her strap on cock lubed up and ready too. Mrs Loving gently begins to work the dildo into Sissy Christine’s ass, making sure to be slow and careful. She tells Sissy to relax her pussy fuck hole and then the dildo slowly slides into Christine’s ass pussy and then the fucking begins.

Sissy Christine feels Mrs Loving’s cock fill and stretch her sissy fuck hole and she wanks her cock as her mature mistress teaches her ass.

Mrs Loving loves to fuck her sissy’s and it really shows in this video here at Mrs Lovings.

Aug 142010

I felt so pretty today in my sissy white boots, I just wanted to be taken care of and pampered.

My tranny friend was coming to visit me later on so I rang and told her to wear something pretty so we could appreciate each others sexy bodies. She didn’t let me down and arrived in a short skirt, stockings and suspenders.

I started to feel hot and horny the moment I saw my transvestite slut friend, with her gorgeous blonde hair to match mine and a really horny lingerie set.

She suggested we go somewhere comfortable to relax and of course I took her up to my room, where we both lay down and started rubbing each others legs.

As naughty fingers rubbed over soft underwear and around the tops of thighs, both of our tgirl shafts started to rise to the occasion. But it was my day to be pampered, so I fluttered my eyelids at my CD girlfriend and she knew I wanted to feel her soft lips on my sissy shaft. I really am a naughty little sissy tart!

My friend slid her fingers inside my transvestite knickers and started to play with my growing member. I moaned like a little sissy tramp as she played with me on the bed with my ass in the air.

She pulled my little knickers down with her teeth and then all of a sudden my hard transvestite cock was being teased by her tongue. She stuffed my white panties up my sissy pussy and pushed them inside, then pulled them out again.

Then my friend stood behind me in her stockings and suspenders and pushed her cock inside my sissy fuck hole, fucking me gently and slapping my ass cheeks as she took her pleasure.

She then flipped me on my back and her shecock went even deeper into my tranny fuck hole as she fucked and used me like a sissy whore.

I felt like such a princess today, I deserve to be treated like one. Even though I’m a very slutty tranny princess!


Oct 192009
Rita Fucks Trannie Husband With Strapon Cock

Rita Fucks Trannie Husband With Strapon Cock

Trannie husband in stockings fucked in the ass by wife with strapon cock in this movie from Strapon Sissies.

Maurice is fortunate to have an understanding wife like Rita, who loves to see him dressed in feminine clothes and underwear.

They especially enjoy their dressing up games when it involves strapon sex, as it takes them to heights of sexual ecstasy beyond anything else they have tried.

Rita enjoys taking Maurice up the ass with her strapon as it gives her a sense of power, and he loves it when she fucks him in his seamed nylon stockings and gives him a real good ass fucking.

Rita gets her crossdresser husband to suck on her strapon cock, then she makes him lie back, open his stocking legs and enters him as she lies on top.

Rita fucks his ass hard, stretching his sissy fuck hole with every stroke of that plunging shaft. Maurice loves being fucked like a dirty whore in stockings and lets Rita ream his ass.

She works him over and burying that cock deep in his asshole she makes him feel like a true sissy fuck doll. After all, that’s what sluts are good for..

See more crossdressing sluts get the fucking of their lives at strapon sissies.

Apr 072009

Curly haired slut gets fucked by Femdom

‘This is one my favorite little sissy kittens, and every time I call her over to play, she gets a brutal pounding from my massive shaft.

‘She dresses oh so femme for me, with her long curls and sexy lingerie. This little minx doesn’t play shy or innocent. Oh no, she’s far too much of a whore to even pretend. Those slut eyes look up at me as she rubs her face all over my plastic meat, licking and begging with her tongue.

‘I put my black boot between her thighs and rub it up into her panties. She rubs back against the black vinyl until she creams herself all over my heeled boot. Such a fucking filthy slut!

‘I force this little tranny cunt to stroke her hard cock, and then to lube up my big black dildo with her creamy hand. Then I viciously pull her up onto a piece of my fuck furniture and pull those teasing panties to the side.

‘”You asked for it bitch!” I give her a cruel look as I position my artificial cock against her sissy hole. I go in smooth and easy, and she whimpers and moans and begs me to stop as I turn this pretty tgirl into another one of my tranny fuck toys.’

Strapon Jane is ready to give out the punishment!

Can you take it!

See Strapon Jane using her strapon like only she knows how to do…