Riding crop on a bare bottom
One of the breathtakingly erotic photographs published on the French site Red Charls

Spanking bottoms are, understandably, nervous about spanking implements like canes and riding whips. I had spanked one young lady with a variety of paddles, but I had not caned her. The last time I saw her (before she moved away) I brought along my evil black synthetic cane and a 24 inch riding crop. I was not planning on using these implements much, if at all. As it turned out, she loved the way they felt. To my surprise, she liked them much more than the paddles I'd been using.

My naughty girl was lying on a padded bench, naked except for a thong and I was spanking her with the crop. She was starting to sink into this blissed out endorphin haze that she got when I spanked her.

I love the way all of the forms of "to whip" sound. "She pulled her panties down and raised her bottom to take her whipping" and "He whipped her bare bottom as she cried" have this wonderful resonance for me. Between sets of smacks with the riding crop, the young lady and I were laughing about the fact that I not only have a spanking fetish, but a fetish for words too.

I told her that I had long had a fantasy about whipping a woman who is wearing those lovely tight riding pants with her own riding crop. Oddly I had not published a story on Hot Bottom Stories with this theme. As it turned out, she had grown up riding horses. I told her that the next time she rode rode a horse I hoped that she would remember the whipping I was giving her.

I think that I wrote this story a while ago. I just found it on one of my computer systems and rewrote it a bit. I think that it pretty much captures my whipping fantasy.

Lela and Josh also tangentially appear in the story A Motorcycle Leads to a Sore Bottom. Lela and Josh will also appear, along with Sol and Daphne, in a couples spanking story I'm working on.


Lela was sitting under a large oak tree, her back against the rough bark, gazing at the mountains. After a time she looked at her watch. She would be about fifteen minutes late she guessed. She got up and walked toward her horse. As Lela walked the flex of her buttocks showed through her cream colored skin tight riding pants.

As Lela had hoped, Josh was waiting for her when she got back.

"You're late", Josh told her. "I was starting to get worried".

"Oh, sorry, I just have lost track of time", Lela replied.

Josh helped her unsaddle and brush the horse. When they were done he told Lela to bring her riding crop into the main room of the barn, where the hay bales were stored. On the floor, away from the main stack of bales, was a small pyramid of bales: one bale stacked on top of three bales that formed a platform for the bale on top. There was a blanket draped over the bales.

Josh kissed Lela's hair, and leaned his head over to her ear. "What happens to young ladies who are late?", he whispered into her ear.

She stretched her head back as he kissed her neck. "They get chocolates?"

"Ah no, guess again, naughty girl"

"Hmmm. 'Naughty girl', that's probably a hint. What could it be? I bet that late young ladies get spanked by their cruel lovers."

"That's right, they get spanked", Josh said.

Josh took the riding crop from her hand. "Bend over the hay bales, please", he ordered.

Lela went over to the hay bales and knelt on the lower of the stepped bales, resting her hips on the top bale, her shoulders lower than her bottom. Josh loved the way the riding pants stretched tight over her raised bottom. He brought his hand down hard on her right buttock, then on her left. "We're going to have a lesson in punctuality", he said as he spanked her. His hand made a loud smack as it slapped the tight material of her riding pants.

"Ow. OK. I'll keep an eye on the time in the future. I was only a few minutes late. Ow", Lela protested. She threw the "Ows" in for effect. Over her riding pants and panties the spanking didn't hurt that much, but she didn't want Josh to know that.

Josh spanked Lela's bottom and upper thighs until his hand started to get sore. His hand probably hurt more than her bottom, he thought to himself. That would change soon.

Josh moved to stand by her left side. "Spread your thighs and get that ass up", he ordered. With her thighs spread and her bottom pushed up, her riding pants stretched over her buttocks like a second skin. He could see her mons outlined between her legs.

He swung the riding crop in a flat arc, bringing the shaft across her bottom. Josh gave the whip strokes across her ass from the tops of her thighs to the upper curve of her cheeks. The crack of the whip across Lela's bottom was echoed by her cries, which sounded more heartfelt than before. Josh counted out twenty strokes silently to himself.

"OK, young lady. You can get up and get undressed, now", Josh told her.

Lela stood up and undressed slowly as Josh watched, sitting on the hay bales to remove her riding boots and then peeling the tight pants down over her legs. She stood up and pulled her white turtle neck over her head. She unhooked her bra slowly, letting it slide off her shoulders as he gazed at her full breasts. Wearing only her panties, Lela knelt on the hay bales again. Josh could see the globes of her buttocks through the sheer white material of her panties. Lela reached back and slowly pulled her panties down to the middle of her thighs. She rested her head on the rough wool of the blanket, pushing her bottom up. Her buttocks were blushed pink from the spanking. Josh thought that Lela looked beautiful, naked except for the panties around her thighs, her ass and pussy offered, surrendered to him.

Josh started whipping her again. The crack of the whip against Lela's bare bottom, uncushioned by her pants, was louder now and the whip left a red mark each time he brought it hard across Lela's bottom. After Josh had given her twenty strokes he stopped and caressed her bottom. He caressed between her cheeks, sliding his fingers down to her vulva, moving his index finger across her lips, which were slick with wetness. He parted her lips and slid his finger inside her.

"You're very wet, you naughty slut. You seem to forget that you're being punished. I can see you need to be spanked harder."

Josh moved his finger inside Lela's pussy, fucking her with his thumb and caressing her clit. Lela moaned.

"Stand up and undress me", Josh ordered. Lela stood up, her panties falling to her ankles and then the ground as she stepped out of them. She unbuttoned his shirt and took the riding crop from his hand, laying it on the hay bales. Then she slipped off his shirt and unbuttoned his pants. She squatted down as she took his shoes off, pulling his pants down over his thighs. Josh stepped out of his pants, his cock was very hard and straining against his bikini briefs. She carefully moved the briefs over his cock, pulling his briefs down so he could step out of them. As Lela knelt she kissed Josh's cock and took him in her mouth.

He gently moved her head away. "You can have that later. I'm not done whipping you yet", he told her.

"Please, Sir, I've learned my lesson. I'm very sore. Please don't whip me more. I'll never be late again, I promise." She moved her mouth back to his cock.

Josh moved away. "Naughty little slut. Now be a good girl and take your whipping."

Lela sighed. "Yes, Sir", she said, as she stood up. Lela handed Josh the whip and bent over the hay bales again, her thighs spread and her bottom raised.

Josh started whipping her again, the strokes harder than before, the shaft of the crop leaving welts from the upper curve of her ass to the tops of her thighs. Her cries, elicited by each stroke of the whip, melded together as he punished her, the cheeks of her buttocks becoming more and more sore, until she was crying steadily, her body lightly sheened with sweat. After he had given her another twenty strokes he put down the whip and slipped his cock into her pussy. He pushed deeply into her, her hot ass pressing against his lower belly. She pushed up against him, starting to move.

"Stay still, naughty girl", Josh told her

"Please fuck me. Please fuck me hard"

"I'm not done punishing you yet" Josh withdrew, his cock shiny with Lela's wetness. "If you want to be fucked, you have to take your punishment first. Ten strokes, extra hard, count them out."

"Yes, sir"

Lela pushed her ass up, offering herself for the whip.

"One", Lela cried out, after Josh gave her a hard stroke across her crimson cheeks. Soon Lela was crying again, counting out the strokes as he whipped her. Lela was still crying when Josh moved behind her, parting her vulva with his finger. She was even wetter than before. He slipped his cock into her and began fucking her hard, slamming his hips into her sore welted ass. Lela pushed her ass up, taking Josh deeply inside her. He reached around in front of her, putting his finger on her clit. She shook with her orgasm and he came inside her.

January, 2008

Case Wintermute