Cum In Heels Stories

360,326 results
Orientation
Length
Source
Infinite Scroll

Stockings and Heels

by PornoPriestess on Sep 16, 2017
Transsexuals & Crossdressers

Shelia kisses Gavin lightly on the knee cap as she slowly pulls up the second black silky stocking up his long pale leg. Gently she straightens outs the seam along the back of his leg and then levels out the lacy tops around his quivering thigh. Shelia crawls backwards to allow Gavin to stand and take everything in. Gavin had never done anything like this b...

Parlor Panties Pt. 03 - The End

by Sanyo81 on Dec 2, 2019
Transgender & Crossdressers

I felt like the sharp nails were going to draw blood. The firm grip was so threatening. I could feel her hot breath on me as she whispered into my ear. "Shhhh, so pretty. Close eyes" More demanding than asking, I did as she commanded. Tingly brushes on my cheeks and hard presses on my eyelids. I dared not open my eyes for fear her nails would rip me apart....

Mistress Chantel, Tranny Dominatrix Ch. 08

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eight: Kerri's First Night at Our Studio. 7:30am. my alarm clock goes off and I awake a little bit groggy, beside me I realize from my fog of sleep that Kerri is asleep with me. I smile as I can't believe it's true. I stare at her, yes from the face up she is in drab at the moment. I have to get use to knowing the girl I am in love with is a genetic...

A Ride with a Stranger

by SkarlitKarson on Sep 13, 2017
Interracial Love

Fiona walks through the hotel lobby toward the elevator. She's had a long day and wants to get some rest before the conference the next day. She especially wants to get out of her heels and take a long bath. "Being a businesswoman can really suck, sometimes." She thinks to herself. "These heels are killing me!" Her 4 inch Christian Louboutin heels are stun...

Sissy Hubby gets a Birthday Treat

by sissychelsea on Sep 15, 2017
Transsexuals & Crossdressers

One of the greatest nights of my life started with a simple request for my birthday. When my wife Madison asked me what I wanted to do, I told her that I wanted to go out with her and have a night of dancing and drinking as "Chelsea", my girly-side. I had been cross-dressing for most of my life and just recently my wife has become more accepting of it. She h...

Let's Be Twins

by manditv on Sep 19, 2017
Transsexuals & Crossdressers

"oh..baby..I'm cumming!! ah!" I pulled out of her nice round ass quickly, so my hot cum would squirt on the pearly white skin of her back and if I shot just right I might get it into her beautiful blond hair. "You asshole! Now I'm going to have to take a shower!" Success, my cum was now pooled in nice white blobs from her ass all the way up to her hair....

Ryan & Tracy's Chicago Weekend

by dcrane1978 on Sep 19, 2017
Anal

It had taken too long, basically all day, to get to Chicago, and the last two hours were brutal, covering 12 miles or so. Seriously. But to the hotel, and into our suite. An added bonus was having a deep, Japan-style spa tub, and it didn't take long for Tracy to plunge right in. She invited me to join her, but it wasn't really conducive to seduction: a two...

Signature Required

by Brian70 on May 29, 2018
Transsexuals & Crossdressers

I was enjoying a rare Saturday alone. It was a cool Fall day. My wife had to work until 4pm to meet with clients that were heading out of town in the evening. So I immediately started to do what I do when I have time alone. I dress, cross dress, become a sissy, whatever you want to call it. She had left early in the morning to do the final preparations leavi...

Turning My Wife into a Hotwife

by Hornyhusband2017 on Dec 24, 2019
Loving Wives

The idea of turning my seemingly innocent hottie of a wife into a Vixen; or a Hotwife as some would call it, was a fantasy that I had been toying with for quite some time. I had no idea how she'd react to me telling her to do sexual things with other men, regardless of if I was watching or not. The thought of this would get my blood pumping and my cock would...

My Mistress - My Wife Ch. 01

by Toby_dog on Nov 18, 2019
Transgender & Crossdressers

A man wants a good woman to love, in his life. One that is smart, as well as, beautiful. One who is he feels is his soulmate. But sometimes, he finds one that has a stronger persona then him. What happens then, if he is weak, is that his male persona is further subjugated by his past. He then finds himself the submissive in the relationship. Thus is the pl...