High Heels, Bra Stories

250,180 results
Orientation
Length
Source
Infinite Scroll

My Own Heaven Ch. 01

by DaniSub215 on Sep 12, 2017
Exhibitionist & Voyeur

This story is fiction based loosely on people, places and events mostly from my life. I love feedback, comments, criticism and ideas for future chapters; it will help me improve my writing, enhance the story line, and encourage me to continue writing. Also, take a moment and vote, your vote tells me how I'm doing. Enjoy, DaniSub * My name is Heather a...

My Strap-on Tales

by domina heel on Jul 14, 2020
Loving Wives

Before my marriage, I had many sexual encounters with my sister-in-law. While my brother was out on a trip, she used to sleep with me and often we used to kiss and fondle each other. My sister-in-law was beautiful with full lips, large pointed breasts, full round buttocks, and a plump pussy. Occasionally, both of us would dress up, she in very high-heeled sh...

More Slutty Wife Behaviour

by Annatartywife on Sep 19, 2017
Group Sex

I was recently involved in a nice sexy gang bang. It was organized by my elder lover Frank, following a sexy discussion with me. He placed an advert in a local newspaper advertising a lingerie party for men looking to buy gifts for their wives at Valentines. He said in the advert that an evening of demonstrations of glamour wear could be organized within...

Learning to Crossdress Pt. 03

by crossdressme70 on Sep 15, 2017
Transsexuals & Crossdressers

I had just had the most amazing first time sexual experience, with the most beautiful erotic lady, I could have ever have imagined, who would introduce me to silk, satin, nylons, and then cover me in lipstick and lip gloss and have me cover her breasts in more and more lipstick kisses before losing my virginity. We had been "relaxing" together for about an...

Marion Turns Me Round Ch. 03

by jomar on Sep 16, 2017
Transsexuals & Crossdressers

You might want to read the earlier chapters for a bit of context.... On the other hand, you know what you're in for here. I hope you enjoy the kink, baby. ***** Early the next morning I stood in my shower, water cascading over me, a razor in my hand. Things were accelerating rapidly now and I figured I'd go along until I was uncomfortable. After all, I co...

Mrs Potter Ch. 02

by Ilbfita on Sep 16, 2017
Transsexuals & Crossdressers

"Oh come on, Mister. Don't look so mortified. A few days ago you were so desperate to dress as a girl that you got caught sneaking around in your mother's bra and panties. Here's your opportunity to take your time and dress up properly, in clothes that will fit, and with an expert to assist you. Yes, I understand how you might feel a little embarrassed, but...

S is for Selena

by BethanyJ on Sep 12, 2017
Transsexuals & Crossdressers

*** Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** "His name is Ken," my friend Isabella had told me as she recounted her own encounter and that of her friend. "I got to first base with him that first time he came in the club. Just a quick snog and then he seemed to...

Fixing The Car Ch. 02

by pup12 on Sep 16, 2017
Transsexuals & Crossdressers

As I had mentioned in the first story about my adventures with my friend Ross and his wife Barbara, that the rest of that first story would be continued and so here it is. After I had cleaned all of the fuck juices from Ross's shrinking cock we all laid back on the bed to rest and I started to think about what we had just done, this was all new to me as I h...

Door to Door

by showitall2u on Jan 20, 2020
Mature

Retirement! I was hoping it would be a great thing. Lots of time to do what I want, read lots of Literotica, walk in the park (who knows who might be there), visit the gym (all those naked bodies), but most of all maybe some time to dress up and see what happens. So finally, my wife gives me a few hours alone, and of course I dive for the bras and panties....

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...