Riding Boots Stories

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Riding Lessons

by Flying_low on Sep 12, 2017
Group Sex

"Ouch! Damn it Rocky, cut it out, that hurt!" Tanya's skin burned where the wet tail had slapped onto her arm and back. She was in a foul mood already and her bay gelding's uncharacteristic fidgeting was making it worse. She aimed the cool water at his tail which immediately clamped firmly between his legs. "You big baby, the water isn't that cold." She r...

Riding Lessons

by E.NonnyMuse on Sep 19, 2017
Group Sex

I had just graduated at Wesley Women's Academy and along with five other girls was taking a summer course that was a combination of horseback riding and sex education. We had finished our morning ride and were standing in one of the barns dressed in our riding gear listening to Miss Chambers our sex teacher. She was a tall woman with a broad ass and huge tit...

Victorian Boots

by nanette21 on Aug 18, 2017
Fetish

He called me on my land line and said "I'm coming over to get my boots. Tonight at 8 PM. And I want my costume cleaned and pressed and laid out on a chair." And then he hung up. My heart was pounding. But I did not know what to do - I hadn't spoken to G in a month and the last time we had spoken it was a bitter argument. He had the nerve to try to scold me -...

John's Riding Lesson

by JohnFranks on Sep 2, 2017
Erotic Couplings

I was round at my girlfriend Rachel's place one day, helping her to clean a few years accumulated clutter out of a closet. One of the items she brought out intrigued me. "Riding boots?" I said quizzically. "Oh yes, I used to ride once, not done it for a while now." She answered. She bent to rummage on the closet floor and I watched her shapely ass wiggle...

A New Way of Seeing Things Ch. 10

by BusyBadger on Sep 11, 2017
Exhibitionist & Voyeur

Natalie's gifts were hidden in an unused pair of riding boots in the back of Gwen's closet as soon as the red-eyed woman got home. She examined the lifelike black dildo for some time, absentmindedly stroking it as she marveled at how the maker's attention to detail made it look and feel like a darker, supersized, version of her husband's manhood. The weight...

Cum in Boots

by cumboots on Sep 15, 2017
Fetish

While I was going through college I shared an apartment with three other people -- one girl and two guys. For a while now Nancy and I had been noticing someone messing with our shoes, especially sexy pumps and boots. Sometimes they were moved (we thought), or there were sticky spots and white stains both inside and out. On one occasion I took a pair of black...

Messy Riding Lessons

by tarred on Sep 11, 2017
BDSM

I trembled with anticipation, the stable yard was quiet, the only sound was the snorting of sleepy horses. I crept towards the tack room, my shadow cast by the full moon above. I fiddled with the lock and swung the door open, I was engulfed with the smell of warm leather and horses, I breathed in the intoxicating aroma. I had been planning this session for w...

Messy Riding Lessons Ch. 03

by tarred on Sep 15, 2017
BDSM

Sarah had not looked shocked some hours later when she had freed me from my pastry like prison. Hilary had left the drying lamps on so the syrup and flour had set like concrete trapping my body. Sarah had first pried my body from the floor with a shovel before washing a quantity of the mess from me. I will still pretty well caked when she stood me up. "Look...

Messy Riding Lessons Ch. 02

by tarred on Sep 15, 2017
BDSM

I found the note on my tack box. It was certainly clear in its instruction, a shiver ran down my body as I re-read the text. I had a decision to make, would I follow the instructions or walk away. Although it seemed that simple this was the step into the unknown, two days ago I had been discovered, mid-self bondage session by my riding instructress Hilary. S...

A Stablehand is Always Good Help

by nikki_267 on Sep 14, 2017
Erotic Couplings

Riding Apples, my horse, all afternoon was making me tired. I decide to take Apples to the stable so I could take a shower before dinner. I walked him to his pen and opened the large wooden gate. I took a bag of his favorite oats out and placed it over his head for him to eat. I took off the saddle and reached for his brush. I began brushing Apples' main. Hi...