Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

New Management Ch. 03

by 510col on Apr 15, 2020
Fetish

Chapter 3 Monday PM When Helen and Greg returned to the office some party food and bubbly had been laid on to say goodbye to Dave. It was as if nothing had happened and the day went on as usual with the slightly tipsy workforce a bit more vocal than usual. Dave was pleased with his send off and even more pleased with his promotion. His wife, Trudie, came...

Maid in Charge

by Dazzle1 on Sep 13, 2017
BDSM

Caroline was entertaining her neighbor Susan. Caroline a tall beautiful woman who lived a lavish lifestyle. Susan was a buxom Nubian divorcee who won a big divorce settlement. "More tea, " Caroline asked. "Yes, thank you." Suki her petite maid came over. "Mmm, Susan sighed in appreciation. "Where did you get this?" "It's a home blend", Suki created." "...

Voyeurs

by Ariel797 on Sep 14, 2017
BDSM

I've wanted this for so long. I finally got the courage to find the right domme to help me, met her for an interview, explained what I wanted, what I needed. Oh yes. Needed. I sit in a cubicle during the day and dream of the time coming soon, soon, and look at my calendar and mark the days. I sit in a cubicle and act demure and petite and smile and think "J...

Barcelona Vacation Ch. 02

by Jack_Love on Sep 11, 2017
Group Sex

After a lobster dinner, Melody was ready to fuck. You should have seen her turning heads in the restaurant. Her massive tits, busting out of her short, black tube-dress, her long, cascading platinum-blonde hair, black fencenet stockings on her long, slender legs, shiny black six-inch stiletto-heels. Some guys were literally almost tripping over when they saw...

When the Balls Drop; A New Years Tale Ch. 01

by LuciousBi-Writes4U on Sep 25, 2017
Transsexuals & Crossdressers

Chapter One- Alone Again Mason walked up to the bar at Mickey's and placed an order for a draft. As he waited he began to look around at all the people wearing crazy hats and things for the New Years Eve party…he thought…why am I here? Another boring party—another shitty year to follow no doubt… It was early still, around 9 pm and there weren't too many p...

Friday the 13th Pt. 03a

by Slave_Georgina on Sep 14, 2017
BDSM

Part 3a continues from where Part 2a left off. Once again my thanks go to SlaveGirl70 and LunarSirius. ***** After she left, I lay as positioned for some time but my ski sock 'breasts' were pressing into my chest and becoming somewhat uncomfortable. With some difficulty, my knees attached as they were by the handcuffs to the foot of the bed, I managed to...

Dealer

by The Pharoah Acitore on Sep 14, 2017
Erotic Couplings

Afternoon sunlight leaks through closed curtains. She fights to stay awake, sinking into the recliner's supple leather, bare feet brushing the rug. Remote in hand snaps the widescreen television on. CNN's prim-voiced newscasters are a welcome break in the apartment's quiet. Luxurious and still, the empty rooms had been napping with her. In her state of exhau...

I Meet My Mentor!

by mairi923 on Sep 17, 2017
BDSM

I was happy with Catherine and over the next few weeks I spent much of my spare time with her, which delighted her as she couldn't do enough for me. I started to get her to change how she dressed, getting her to buy garter belts and more modern knickers and bra's, particularly under cup and push-up bras, as I told you she was plump and had such lovely tits....

Birthday Present

by Osiris18 on Sep 13, 2017
First Time

"Jordan, wake up!" shouts Ron. "Ugh, go away, ass!" say I, still half asleep. "Jordan, are you going to spend your 18th birthday asleep or come see what is in store for you?" Suddenly I jump, realizing just what day it is. I am finally 18! "Ron, what time is it?" I mumble. "Dude, it's nine." Shit! I am late! Rachel is going to be pissed! I hurry an...

Modelling

by corsetheelscollar on Sep 16, 2017
Transsexuals & Crossdressers

I owed him part of the rent. The agreement had been clear when I'd taken the room that I would pay 30% of the rent and bills for one room and use of house amenities. But this month I'd been hit by a cut in overtime and some car repairs. I won't talk about money here. It's always a source of depression. My flatmate's name was Carl. We sat at the kitchen tab...