Chess

"You're not going to like this." Jason said smirking. Holding his bishop, delicately between his index and middle fingers.

"That's what you think." Rachel said back. "I know I can win this time!"

"Really?" Jason raised an eyebrow, "Because I know for a fact that once I make this move, I can check mate you in three more turns. But, I could always..."

"No!" Rachel interrupted. "You're not allowed to lose on purpose. I want to win fair and square."

"Fair and square?" Jason chuckled. "I think your little distraction tactics have already negated 'fair and square'." He looked down between his legs. Under his pants and underwear, Jason had a small vibrator rubbing against his prostate and a vibrating ring around the base of his cock. Both of them were controlled by remotes which were held by Rachel.

She had been fiddling with and changing the setting throughout the six games they'd played.

Currently, the one in Jason's butt was vibrating on the highest saiding, while the one around his penis was gently pulsating. Rachel had found this to be a rather effective combo, but it hadn't stopped Jason from winning.

Rachel angrily blushed, turning the vibrations on Jason's cock up, causing him to grit his teeth and make that "hnnng!!" sound she thought was so hot.

"I may have given myself a bit of a handicap," Rachel answered, "But that's different from you letting me win. Now make your move!" she ordered.

"If you say so," said Jason, moving his bishop to take her queen. Just as Jason had said, it only took him three more turns to win the game. "Check Mate." he announced, grinning.

"Dammit!" Rachel said, grabbing her hair. "How are you so good at this?"

"Years and years of practice." Jason responded, leaning back and putting his hands behind his head. "Oh, and because I'm a genius." he added smugly.

"That's it." Rachel said, grabbing Jason by the collar of his shirt. "That's enough chess. Bedroom. Now."

Jason smiled and blushed. He knew this might happen and was honestly looking forward to it. He eagerly followed Rachel to their room. Rachel ordered Jason to take off all of his clothes as she did the same. He'd been wearing a sweater vest and a tie over a pink, button up shirt and a slim fitting pair of khakis. as he took them off, he gently folded them before placing them on a chair. She was wearing a white t-shirt and cargo pants. When Jason and rachel were both naked, she told him to remove the sex toys she'd put on him for the game then wait on his hands and knees on the bed, while she got the supplies ready.

Rachel went to the closet in their room and took out a strapon with a thick, six inch, pink dildo attached to the end. She put it on and grabbed a large bottle of lubricant. As she approached the bed, she looked over Jason's naked body. He looked so vulnerable in that position. His body was completely hairless. He had always shaved his body hair more than most men, and when he got involved with Rachel they both decided that he would keep his entire body completely smooth and hairless at all times.

Jason glanced back at Rachel, his penis getting stiff looking at her. She had a curvy figure, average breasts, long and flowing dark brown hair, and although she was not particularly muscular, something about her poise made her appear very strong, especially when she wore one of her strapons. Squirting out a dollop of the lube onto her finger, Rachel got behind Jason.

He shivered as she rubbed the lube on his cute, pink hole. Both from the cold sensation on his anus and the anticipation of what was going to come next. Grabbing Jason's thigh with one hand, and her strapon with the other, Rachel slowly inserted the strapon inside Jason. He moaned and gasped, feeling a sharp pinch as the dildo was inserted.

The pain quickly subsided as the dildo began to push against his prostate. Rachel leaned in until her breasts were pressed against Jason's back. She loved the feel of his warm, shivering body pressed against her own. She reached around his chest and began playing with his nipples. They were so soft, she couldn't resist rubbing, pinching, and twisting them every chance she got.

"Not so cocky now, are you?" she whispered, her lips so close, Jason could feel her warm breath on his ear. He wanted to respond with a witty retort of some kind, but he was so overwhelmed with pleasure that he could only respond by sighing and moaning in pleasure.

"Good boy." Rachel cooed, patting his head. Jason's cheeks were turning a bright shade of crimson. Jason's precum started dripping on the bed. He was grabbing at the sheets so hard his knuckles were white, resisting the urge to touch himself.

Rachel had made it a rule that he was not allowed to play with himself at all when she pegged him. She wanted to be the one giving and controlling his pleasure when she fucked him. Sometimes she would be generous and firmly grab and stroke his cock. This time, she was doing him no such favors. She wanted him to cum from the sensations in his ass and from his nipples only. His penis wasn't going to get any direct stimulation this time.

It took nearly twenty minutes of hard pegging for Jason's cock to finally erupt, shooting thick ropes of cum onto the bed sheets. The orgasm shook Jason's whole body. Rachel slowly pulled the strap-on out of him, took it off, and sat at the head of the bed.

"Now it's your turn to give me an orgasm." Rachel said spreading her legs. "Get over here and put that tongue of yours to some good use."

Jason crawled forward until he was in the right position and laid on his chest. He put his mouth up to her labia. She's already soaking wet. He takes his time at first, slowly licking up and down. He gradually ups the intensity, licking faster and deeper, flicking her clit with his tongue. Rachel grabbed the back of Jason's head pressing him harder against her. After a few minutes of him passionately licking, Rachel had an intense orgasm, her whole body shaking.

Jason persisted, giving her orgasm after orgasm until they were both worn out. When he was done, he crawled up next to Rachel and lied down beside her. She lightly stroked his hair and looked into his eyes, telling him what a good boy he'd been.

"What do you say we take a quick nap, then play a few more rounds of chess." she asked him.

"Sounds perfect." he replied.