Cum In Heels Stories

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College Hockey House Gangbang

by Roxyfox_y on May 11, 2020
Group Sex

It all started on an innocent Thursday night my sophomore year. Being only 20 we couldn't go to the bars so the girls and I went looking for a house party. Sarah was dating a senior on the hockey team and said we could go over to the team house if we wanted to drink for free and hang out with the guys. Since I had been wearing out the batteries on my favorit...

Chris & Lisa Ch. 1

by cbf316 on Sep 2, 2017
Fetish

Lisa walked in and threw the bag on the bed and let the items fall out. The one item she grabbed out of the bag and threw the rest in the drawer. A bottle of silver polish was in her hand as she walked over to the closet and looked at her silver outfit. A small halter top along with silver shorts and silver heels was quite an outfit. She then sat down on...

Caught in High Heels

by BigAndy922 on Sep 11, 2017
Transsexuals & Crossdressers

I couldn't believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now. My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work and needed to leave before he'd finished, so she'd asked me to...

High Heels and Stockings Tryout Ch. 02

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2: Bi-sexual Sluts in Stilettos Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy! * After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high...

The Fetish Shoe Shop: Carmen

by fantasyboy on Sep 19, 2017
Fetish

Mrs. Wyles had a rather unusual request but after discussing it we were very keen to take it on. In fact talking about the couple in question Chris and Carmen turned us on so much that Mrs. Wyles and I ended up both wearing stockings and high heels and fucking each other. I bought her to an orgasm then she jacked me off using her stockinged feet and made me...

9 Stone Cum Queen Rides the Train

by 9StoneCumQueen on Sep 18, 2017
Exhibitionist & Voyeur

(This is my fourth story for Literotica) * Here I am. I'm riding the Circle Line tube train round and round. I have been round London three times already. I stay in the same seat. I drink Cherry Coke. Different men sit opposite me. Men come and go. They look up my skirt. I encourage them. I swing my legs high when I cross my legs. I am in no doubt that th...

9 Stone Cum Queen in the Mirror

by 9StoneCumQueen on Sep 18, 2017
Erotic Couplings

(This is my first story for Literotica.) * Here I am. I weigh nine stone. That's a perfect weight for my height. A doctor told me. That's me in the mirror. It's two in the morning. I look much the same as I did at eight o'clock this evening. The strap of my black satin dress has slipped from my shoulder. You can see my bra-strap. I have a ladder in my stoc...

My Life as Lauren Ch. 05

by Lauren_xxx on Sep 14, 2017
Transsexuals & Crossdressers

Bev let my go early and she came with me and Kate back to our apartment, to help me decide what to wear. They stripped me naked and made sure I had no body hair they even shaved my pubes. I sat on the bed naked as Kate went through my drawers and Bev my wardrobe. Bev had me stand up and try on different outfits some slutty, some very classy in the end we dec...

The Storage Bin

by gg9510 on Sep 16, 2017
Transsexuals & Crossdressers

Wednesday night was "girls" night out. Religiously, Jill went out with her friends on Wednesday, which left me with a night to do with whatever I pleased. Over the years I have grown to love my Wednesday nights "alone". Back when Jill and I first moved in together and she first started her routine mid week evenings out, I was still working towards getting...

Client Satisfaction: High Heels

by HeyAll on Jul 2, 2018
Group Sex

Samantha was worried that she'd be wobbly in those new heels when she slid them on her feet that morning. As she tightened the straps around her ankles, she wondered if she should have gone with the more sensible flats that she normally wore for work. But she was feeling a little more dangerous today. Besides, she was damn proud of these new heels. They were...