Day 30 Orgasm 34

Ruby Ryder

He bought the gloves for her one night after dinner. They were walking along Main Street and impulsively stopped in a thrift store, open late. They'd been talking about leather gloves. He loved them. He loved all things leather.

"Can I help you find anything?" The salesgirl approached as soon as they came through the door.

"We're just looking for one thing, leather gloves." She smiled at him when she said it.

"Well if we have any, they would be over there." The salesgirl gestured to a display against the wall. And there they were. The sheer improbability of them made it all the more fun to see the shocking pink fingers peeking out from behind the rest.

She pulled them out from the pile and slipped them on. They fit snugly; her hands were not small. Elbow length. They fit well. The leather was smooth and the gloves were lined. Despite the garish color they spoke of quality. The tag said $6.

"What do you think?" He stared at the gloves on her hands as she held them up, examining them, flexing her fingers. He envisioned them around his cock.

"Well, they fit. And they're nice." 

"Six bucks!" He countered.

Seeing the wisdom of his point, she acquiesced and he paid for them at the register. They walked to a bar up the street. They sat at the high tables and drank. She had fun putting the gloves on despite the warm summer evening. She ran her fingers up and down his arm as he fidgeted and shifted on his stool while his swollen cock grew uncomfortable. Downing the rest of their drinks, they left for the hotel.

The moment they walked into the room she put the gloves on. Kissing him, her hands were on the back of his neck, pressing his lips to hers. Those hands with the gloves, they took his clothes off with a sense of purpose and intention. Soon he was naked. The belt came out of her jeans and she used it to tie his hands together in front of him.

She turned him around and started slapping his ass hard with her gloved hand while he stood there.

"You like leather?" Smack.

"Ah! Yes." Smack.

"Yes I do. Ah!" Smack. His cock was hard. He was loving this.

She gestured towards the bed. "On your hands and knees!" He climbed onto the bed and put his head down into the pillow, offering her his ass for more spanking. More leather.

Instead she walked up to the side of the bed, reached under him and grabbed his cock hard, making him jump. It felt good but almost hurt. She knew where that line was. The feel of the leather on his cock was exquisite. But she spanked him hard with her other hand, surprising him. He moaned and twisted in pleasure and pain. She used his cock as a handle while she punished his ass. He didn't know what to feel with the contrasting sensations. His ass throbbed with pain at each hit of her hand and then he felt her squeeze his cock, which throbbed in pleasure. She kept this up until his ass was on fire and his cock desperately wanted more action.

She abruptly went to her purse and retrieved a small bottle of lube. He smiled. She was the kind of woman who would carry a bottle of lube in her purse.

His ass was hot and sensitive as she pulled his cheeks apart and slipped a well-lubed gloved (!) finger into his ass.

"Oh! Honey - the gloves." She knew he was lamenting the use of her pretty pink gloves. They'd be ruined.

She pulled her finger out of him and spanked him even harder, the lube getting on his ass and the sound changing to a wet one. Smack! Smack! Smack!

"Six.....bucks....Sweetheart!" Each word punctuated with a slap of her hand as he groaned.

She eased another finger into his ass and he spread his legs to accommodate the invasion. He was new to ass play, but loved it.

"Count to ten, and when you get there, start over and keep counting!"  What was this about? He started counting.


The first ten she kept her fingers still in his ass and stroked his cock - heaven! The second ten she gripped his cock hard and fucked his ass with her fingers, ten strokes. The third ten she gave his ass well-placed wet slaps with that strong leather-covered hand, making him wince and squirm. And then she started all over again.

"Be still!! You want leather? I'll give you leather. Keep counting!" He thrilled to the sternness in her voice.

Oh, his cock, his ass and the spanking! Pleasure, pleasure, pain. Feeling the pressure build, feeling her fingers on his prostate and then feeling the sting of his ass cheeks, getting more and more sore each round. The spankings weren't allowing him to quite get there, and she knew it.

And then he felt her third finger, slowly pushed into him while she slid her leather glove over his cock for another ten strokes. He thought he would explode right then, but it took one more round. When she fucked his ass with 3 fingers, he was transported. He hardly felt the spanking that came next, he was still flying high from the finger-fucking. And when she started stroking his cock, she knew how close he was and she thrust her fingers into his ass at the same time, wrenching his orgasm from him, leaving him no choice.

He stopped counting at number 5 as his spasms began.

"Oh fuck! Oh Jesus!"

"Keep counting!!" What? She was serious!

"AH! Six! Fuck! OH! Seven!" Come was already spurting out of his cock and she was determined to get to ten.

"Count, damn it."

He realized he'd better count fast.

"EightNineTEN!! Oh fuck, oh fuck!" Though he'd rushed through the last three, she took her time with them, stroking his cock hard and over the head, pushing her fingers deep inside him to feel his pulsing prostate. Overwhelming him with too much sensation as he cried out for everything to stop. When she did stop, he was trembling, gasping for breath. His whole body still pulsing with pleasure.

The hotel guests in the nearby vicinity likely paused for a moment when they heard his reaction to nine and ten. The sound was of a man in pain...and pleasure.


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