Highheels Stories

39 results
Orientation
Length
Source
Infinite Scroll

Finishing School For Ladies Ch. 10

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Ten - An Offer You Can't Refuse Valerie strode confidently down the hall towards the Deputy Headmistress' study. Sitting outside the study waiting for an audience were Billy Butler and Alice Corinda. Valerie winked at Billy and opened the door without knocking and strode into Lisa Meakins' office. "How dare you come in here unannounced Miss Swindo...

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

Willkommen in der Sexworld

by JeffStarkmann on Jan 9, 2018
Group Sex

Helle Blitze reißen Andreas aus seinen tiefen Schlaf. In seinen Zimmer schießen aus alle Ecken blaue Blitze. Panisch duckt er sich, aber als in dennoch einige Blitze berühren, merkt er das diese keine Schmerzen verursachen. Als er sich wieder gefasst hat rennt er nur in Boxershorts gekleidet aus seinen Zimmer um nach den Rest seiner Familie zu schauen. Andre...

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Biker Bitch Ch. 07

by MicheleNylons on Dec 31, 2017
Transsexuals & Crossdressers

Chapter Seven: Tradecraft Cassie Rode back across the border to Mexicali and let Diego call in some Cartel guys to pick him up. "Those fucking Devil Dogs Cassie! Why would they do that?" he was angry but also confused. "That fucking Miguel Rodriguez was obviously a rat. Did you see him waving at those Feebee fucks!" Cassie spat. "I thought he was going f...

Emergency Cast Member

by spandexman on Aug 22, 2017
Fetish

The Play Is The Thing 1 Cordville Occupational College is known for business, computer, and secretarial classes, a decent sports program, and even a fair automotive department, but not drama. I was one of about twenty students, ironically there were twelve boys and only eight girls in the program. I soon became the second in command, behind Roxy Hart, the 5...

Donna's AMEX Christmas Party

by sharedhousewife on Sep 17, 2017
Loving Wives

AMEX X-Mas Party Dan's Version to Scott Donna and Dan had gone together to an employee Christmas Party for American Express, where they both worked. Spouses were not invited, because it was for employees only. When Dan got to our house, he saw Donna's attire. A short black cocktail mini-dress that pushed her 36DD's almost out of the dress and matching ankl...

Buttsex with a Hooker

by shadoblivion on May 21, 2019
Anal

Although I've been a member of Literotica for a long time, I've never made a submission until now, mostly because the stories I create are for my own entertainment and I was terrified of sharing my own deepest fantasies with anyone else, let alone strangers. This story is something I wrote many years ago when my writing was much simpler and more crude than i...

Pillow Talk Ch. 05

by MicheleNylons on Sep 11, 2018
Transsexuals & Crossdressers

Chapter Five - Braciole The first plate whizzed past Frank Caputo's right ear and crashed into the wall, closely followed by a second that skimmed off his shoulder and shattered on the floor. "For fuck sake Michelle if I wanted this fucking drama I'd go home to Benedetta," Frankie whined, but he was laughing drunkenly. "Why don't you then? You can fuck he...

Biker Bitch Ch. 05

by MicheleNylons on Dec 29, 2017
Transsexuals & Crossdressers

Chapter Five: Fuck The Business! "What the fuck was that!" Dale was shocked and angry. "Shut up and lookout to make sure we aren't followed while I concentrate on driving," Cassie was driving at high speed to the arroyo where she had parked her BMW. Cassie pulled off the short blonde wig she had worn as a disguise and Steve ripped off the salt 'n pepper w...

Sisi

by leofist2 on Apr 21, 2020
Non-English (dated)

Sisi, die Reha Die fiktive Geschichte handelt vom Ehemann Leo, 54 und seiner optisch, anziehenden Ehefrau Sissi, 48. Beide sind für ihr Alter, aufgrund sportlicher Aktivitäten und gesunder Ernährung, sehr gut in Form. Sissi ist, egal was sie anhat, ein Hingucker. Wenn Leo zu öffentlichen - oder auch Benefizveranstaltungen eingeladen wird, ist sie noch immer...

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