Heels Stories

80,885 results
Orientation
Length
Source
Infinite Scroll

The Girls College Ch. 09

by TF2123 on Jul 31, 2018
Fetish

The sun had risen over London, birds were excitedly chirping as many people started their daily commute. It was Wednesday the sixth of September, the summer holidays were over. As the bright rays of sunlight kissed the glistening windows of London Girls' College for the first time that day, Paul Edwards was already wide awake. He had been, quite rudely, awo...

My Life as a Secretary

by MissYellowPanties on Nov 25, 2017
Transsexuals & Crossdressers

After the night before. Charlie and I had been given adjoining rooms, that was going to be very handy, now that we were both secretaries we could spend the night together without getting our asses reddened by a punishment spanking, and I sensed the promise of many long nights of fun ahead for us. It took me all morning to pack and unpack my things, after...

What If?

by funtungnfrog on Sep 13, 2017
Loving Wives

OK, this is pure fantasy. Like many guys the idea of having an open marriage has always been intriguing. Now that is not the same opinion as my wife. So this is a bit of my fantasy that opens the doors in a way that she takes the steps to increase the opportunities of the road to extended pleasure. What if she really wanted to have another guy? What would th...

Another Football Season... Ch. 03

by R_U_Romantic on Sep 14, 2017
Erotic Couplings

I slept til noon the morning after Barry and I had made love during the fourth quarter. Slipping into my fluffy white robe I made my way to the kitchen. "Morning Margaret." Barry said not even lifting his eyes from the sports section. "Good morning Barry." I replied. I poured myself a cup of coffee and sat down across the table from him. I let my robe f...

A Gift for Simone

by geronimo_appleby on Sep 17, 2017
Loving Wives

A Loving Wives piece from me. As ever with LW I'm looking forward to any comments the piece may garner. It's always an experience. Simone wants Jake, but he's married. Oops. GA -- Benissa, Spain -- 24th August 2013. One "Look at her, the fat cow." Alison paused with a cherry tomato halfway to her mouth. She blinked and lowered her fork, replying with:...

April's Vulgar Arousal

by sweetkarolina on Sep 17, 2017
BDSM

Part 1 "And Janice would you please get me the municipal proposals' summaries from last month," said April Dowze emphatically to her new secretary for the third time that day as they walked down the hall, Janice helping April with her Jacket and her coffee and her stack of files. April had a meeting with the C.E.O of Cellucorp, a cell phone company located...

My New Neighbours Ch. 02

by csm1967 on Dec 19, 2018
Transgender & Crossdressers

Apologies for the time it has taken to write this second chapter. I went on an overseas holiday and when I returned had to move house. Still settling in so hopefully, this won't be too disjointed as a result. ***** I closed the front door behind me and leaned back against it, eyes closed. My mind was swirling with what I had just been through. It was witho...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Tiffany's Deal Ch. 02

by MicheleNylons on Jun 24, 2019
Transgender & Crossdressers

Chapter Two - The Flop Tiffany's earliest memories are of her as a young boy growing up in the Midwest. To say that her upbringing was difficult would be an understatement. Although not particularly small for his age Tom Robinson was very lithe and almost effeminate in manner. From the outset Tom knew he was different. He began to feel trapped in a body in...

Girlfriend with Testing Device Ch. 06

by Razmagurk on Sep 11, 2018
Transsexuals & Crossdressers

Author's Note: This is part six of my smutty romantic comedy series. This chapter is the final chapter of the Mall Arc, and while it's not the sexiest, its got lots of crazy swaps going on. The next chapter marks the beginning of the Strip Club arc, where things start to get way sexier. =-=-=-=-= Warning: this chapter is rated a swap-happy R and includes (...