Cum In Heels Stories

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The Garage Sale

by Iamhypnobyheels on Dec 2, 2019
Fetish

I enjoy going to garage sales. It's something to do on a quiet Thursday or Friday afternoon when the wife is still at work. And you never know what you may find. For me, old baseball cards, usually thrown into a box without thought. For 5 bucks, you may get $500 or more in value. The owners just want them out of their house. Last Thursday I was doing what...

Chris & Nina

by cbf316 on Sep 16, 2017
Anal

Nina was pissed as once again her boss Chris was using his power to make work more uncomfortable for all the females. For the past 2 years females have to dress up every Friday or be fired. That meant wearing 5 inch heels to work. Nina didn't like to wear heels to work as she had to walk around in them all day as Chris would not allow the woman to kick off...

Chris & Kim

by cbf316 on Sep 11, 2017
Fetish

Kim was pissed as once again her boss Chris was using his power to make work more uncomfortable for all the females. This time the females has to dress up every Friday and that meant wearing 5 inch pumps to work. Kim didn't like to wear heels to work as she had to walk around in them all day as Chris would not allow the woman to kick off heels, they must be...

Chris & Cindy

by cbf316 on Sep 16, 2017
Exhibitionist & Voyeur

Cindy who was a teacher at Chris's school was none to happy with him. About a month ago out of the blue, he broke up with her niece Lisa and Cindy was none too happy in the way he did it. He blew her off a week before her prom and Lisa had taken over two months to recover from the blow. Now Chris didn't know that Cindy and Lisa were cousins. Cindy was a f...

Always Read Before You Sign Ch. 03

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

"Wakey wakey sleepy head," Paula said. Samantha groaned. "What time is it?" "It's seven in the morning," Paula replied. "It's time for your boosters." Samantha got up slowly and yawned. She felt the two pricks on her arm. "All done," Paula said. "I would let you sleep for longer. But I've got to go out." "To the office and do shopping, yeah?" Samantha r...

It Started with the Shoes

by onedreamer56 on Sep 14, 2017
BDSM

Or how my wife became a Shoe whore and Exhibitionist. It all started with the shoes. My normally sensible and conservative wife and I were shopping. We walked past a top end shoe store where she spied a pair of 6-inch designer jeweled high heels. She was all gaga over them, which was normal. "They're too tall for you, as the highest pair you claim to b...

Ms. Jay's Shoe Store Encounter Ch. 01

by jojo23456 on Sep 16, 2017
Transsexuals & Crossdressers

Ms. Jay woke up thinking it would be a fine day to miss work and go shopping for that new pair of high heels she so desperately wanted. After eating breakfast she prepared to go looking as sexy as she could, she wanted all the men to turn their heads to watch her hip movement. Arriving at her favorite store," Bells shoes for Large Women," she noticed anoth...

The Fetish Shoe Shop: Nita

by fantasyboy on Sep 11, 2017
Fetish

Rob telephoned The Fetish Shoe Shop to make an appointment for his wife Nita. It was her birthday soon and he wanted her to visit the shop as a surprise birthday present. Nita has a serious shoe fetish and loves nothing better than having her toes sucked while she has a cock in her mouth. We weren't sure whether Nita had any bisexual tendencies but Mrs. Wyle...

Some Hotel Fun

by antooine on Sep 13, 2017
Erotic Couplings

We meet in the lobby of the hotel- I'm wearing dark jeans, nice boots, a collared shirt and a leather jacket, and I see you, leaning against the wall, watching and surveying the room, waiting for me to come in the main doors. I came in the side, so you don't see me as I sneak up to you, and put an arm around your waist. I whisper into your ear, asking if you...

High Heels and Stockings Tryout

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

High Heels and Stockings - First Time I blame Literotica, or credit it, as the case may be. I've always been excited by women's sex clothes -- high heels, stockings, panties, and skirts, and have shot lots of loads fantasying about how hot women look all dolled up. Then I came across Literotica, and started reading all the nasty, filthy stories about cross...