Good Sport

“Promise you’ll be a good sport?” asked Gem as she held her boy’s chin in her slender hand and looked down at his radiant eyes.
“Yes, Mistress,” he answered evenly, not moving a muscle.
“You know the rules,” she continued.
“Yes, Mistress,” he replied.

She slid her hand around to the back of his head, feeling his bristly hair barely making it past her fingers and leaned down to whisper in his ear: “Don’t give up too easily.  Have fun, and be a good boy.  And remember: this is not for you.  This is for me.  Your pleasure is my pleasure.  I’m so looking forward to seeing my friends enjoy you the way I do.”

She stood up, and he followed.  She turned to face three of her friends who had been watching the conversation. “Well, ladies,” she said, smiling a Cheshire cat smile and clasping her hands together, “I believe you know the rules, too!  Be kind to my boy and have fun yourselves!  I’ll be watching from up here.”  Her friends broke into their own nervous but eager grins, slung their backpacks over their shoulders, and nodded in assent. She turned back around to face Boy and told him he had a five minute head start.

“Go,” she said.

He started walking out of the room briskly, breaking into a run as he approached the stairs.  They all watched his graceful body sprint onto the lawn from a floor to ceiling bedroom window upstairs.  Soon, he had disappeared into the hedge maze below.  Gem looked at her friends, their smiles belying their anticipation.  He was beautiful and so eager to please.  A few minutes later, they wandered down into the entrance of the maze together, separating shortly thereafter to take different paths.

Susan was the first one to spot him.  He was walking slowly along the ledge, creeping silently.  Like a cat, she tiptoed up behind him and lightly tagged him on the shoulder.  “Looks like I’m first!” she exclaimed with delight.  “What would your trophy be, then?” Boy asked.  “I was thinking about how satisfying the silk of your shirt would feel against my skin –” she said, “but instead I think I’ll have your trousers.  I want to be the first to see the outline of your lovely cock.”

Dutifully, he removed his shoes, then unbuttoned and slipped off his trousers before handing them over.  “Thank you,” he said.  “May I continue?”  “Of course,” she replied, looking him up and down.  He walked off quickly and slipped around the corner while Susan waited patiently.

He’d been carefully avoiding cul-de-sacs the entire time, but now he found himself trapped in one.  No matter – he stopped and could hear nothing but his own shallow breaths.  He was alone, he was sure.  Coming out of the dead end, he felt a hand stop him before he saw the artfully manicured nails on his chest.  Lilia.

“So,” she purred, looking down at his boxer briefs.  “I see someone else got to you first.”  “Yes, ma’am,” he replied.  “What trophy will you have?”  “I’ll take your shirt, darlin’,” she said with joy.  He started unbuttoning; she stopped him.  “No – let me,” she said, continuing to unbutton his soft shirt languidly.  “You have nice shoulders,” she said, running her hands over them briefly.  “Thank you, ma’am,” he replied, his heart racing, now down to his undershirt, briefs, and running shoes.  “May I continue?”  “Sure thing, love,” she said, and swatted his bottom as he made his way down the lane.  Upstairs, Gem laughed as she watched him scurry away.  She could see what he couldn’t: that being so distracted by Lilia’s comments, he wasn’t watching where he was going, and that’s when he ran smack into Susan once again.

“Oh-ho,” she said, “I’ve found you once again!  I’ll have that undershirt if you don’t mind – I think it will look quite nice on me, especially paired with your pants.”  He blushed and removed it, one hand on the chest and one on the back.  He handed it to her, avoiding eye contact.  “Looks like it’s almost time,” she said.  “Be more careful – you don’t have much left.”  “Yes, ma’am,” he replied, and he was off.

A solid five minutes had passed; he was hidden in the middle of a hedge, completely convinced that he was invisible from passersby… until he heard a voice whisper into his ear, “Think you’re clever, do you?” as a hand reached in and grazed his hard, smooth stomach.  A warm hand attached to a reassuring voice.  A voice like bells.  Yuna.  She drew him out of the hedge.  “I believe I’m now the proud owner of one pair of black boxer briefs,” she said, smiling at Boy.  He started to slide them down. “Wait,” she said.

She opened her backpack, took out a double duvet, flung it upward with two hands so that it opened onto the ground, and sat down on it, looking at him expectantly.  “Now,” she said.

He once again took off his shoes and slid the briefs over his growing cock and down to his ankles, carefully removing them one leg at a time before handing them to Yuna, who patted the duvet next to her.

“Your turn to watch,” she said.  He sat in the middle of duvet and looked at Yuna as she stood up, his eyes briefly darting to the window above to see if he could catch a glimpse of his Mistress.  He couldn’t, but he could feel her eyes on him.  He could always feel her eyes on him.  Yuna was wearing a simple flowered summer dress, tied in the back; she pinched the strings of the tie between her thumb and forefinger and pulled, her dress falling to her waist, exposing her pert breasts.

She looked down at Boy.  “I want you to take my panties off for me – with your mouth,” she said.  He got up to balance on his knees and lifted her skirt up, and nuzzled his face against the lace of her crotch.  Her breath was barely audible, but deep.  He grabbed the top of her panties with his teeth, sliding them down a few inches, before darting his tongue over her clitoral hood, holding it there momentarily, and drawing it back.  He gripped her panties once again and slid them down to her ankles.

She stepped out of them and eyed him hungrily.  “On your back, please,” she said, getting a condom and cock ring out of her backpack.  He obeyed; she slid the condom down onto his now rigid cock and stretched out the disposable cock ring to place it around the base of his scrotum and the top of his dick before turning both switches on, making everything vibrate.  She blew a small silver whistle she was wearing around her neck before taking it off and flinging it to the ground.  Still wearing her dress, she hitched the skirt up and kneeled above Boy before slowly lowering herself onto his cock, then gently rocking back and forth.  He moaned, imagining his Mistress touching herself, watching from above.

“Don’t enjoy this too much,” Yuna said in staccato, finding it difficult to talk and fuck at the same time.  “The others are on their way.”

Gem, now soaking and wearing only a tank top, looked down to see Yuna straddling Boy while Lilia and Susan approached quickly from either side of the maze.  She mounted a dildo in the window seat and stared, enthralled, her hands pressed to the rapidly steaming glass, thinking: AirBnBs couldn’t possibly get better than this.