Cum In Heels Stories

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Infinite Scroll

9 Stone Cum Queen in the Club

by 9StoneCumQueen on Sep 18, 2017
Group Sex

(This is my second story for Literotica.) * Here I am. I am sitting on a toilet, in a club, in a basement, in the centre of London. I am fully clothed. I am wearing black opaque tights over my long legs. I am wearing yellow court shoes with three-inch heels. I am wearing the tightest, highest denim shorts you have ever seen. I am wearing a simple black...

Carol's Mom Ch. 02

by shoeslayer on Sep 16, 2017
Fetish

Sure enough, the next morning Carol says, "Well Harry, today's the day I help you cum my mom's heels, her nice patent black heels, we are going to cover the bow and mess the insides up for her, what do you say?" "What do I say? It's a great plan, but you have to really get me turned on first, are the heels here or do you have to get them?" "Right here, Har...

What a Way to Wake Up

by lrwriter on Sep 17, 2017
Loving Wives

There has always been one thing that has turned me on more than anything else, and that's a woman in stockings and high heels. I don't mean pantyhose. I mean real stockings attached to a garter belt, or stay-up thigh highs. And I don't mean clunky high heels or so-called "stripper shoes" with the platform soles. I mean old school, stiletto pumps or sexy sand...

What's Love Got To Do With It? Ch. 05

by jessikab on Mar 30, 2020
Fetish

The boys couldn't have been gone more than 5 minutes before the doorbell went. I hadn't even had the time for a cup of tea, but walked carefully to my room preserving my boyfriend's treat in my panties and sent my dishevelled, spunk-spattered flatmate to the door in nothing but panties and a T-shirt. I too was a cum-covered mess: it was in my hair, my mouth...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Alex Struggles to Accept who He Is

by Shy_n_bi on Jul 29, 2019
Transgender & Crossdressers

Alex never thought he'd be living in this moment, a desire that he kept buried ‎deep within for his entire life and now a near reality! His eyes locked on her every move as his heart raced like he had never felt it race before and the battle between pleasure and guilt had all but began leading from his mind to the pit of his stomach! There he was, nervousl...

Twins in Mind and Body 01

by KaereniSister on Oct 11, 2017
Novels and Novellas

This story is copyrighted 2016 by Kaereni, may not be excerpted, reprinted, reproduced, or reposted in any form without the express written consent of the author. Visitors to this web site may read or temporarily download pages but are not permitted to modify or re-distribute them. The story may contain sexual activities and situations that are to be read o...

High Heels and Stockings Tryout Ch. 03

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

My night of CD sex with Samantha and James had been so hot, it was practically all I could think about the next week. My wife and I had fantastic sex, with plenty of backdoor fun, including my wife sliding a lubed finger up my tight ass while sucking me, until I flooded her mouth. I also had her dress like a slut and slowly drove my cock into her bottom, pou...

Recruiting of a Sissy Maid Ch. 14.5

by Sissy_Chantel on Dec 16, 2017
Transsexuals & Crossdressers

Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it. ***** Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story Friday night, I've been feeling a desire to dress up as Bailey all fucking day...