Warning: This story contains graphic scenes depicting pain and humiliation and has one watersports scene.
This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are 18 years or older when in sexual situations.
This is Boxwood's and Mistress SWP's shared fantasy.
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Chapter Eight
He had his instructions now. The day after his video with Jennifer, Mistress Elaine had an Uber driver pick him up at noon. The wipers swished in a steady rain as he rethought the experiences he'd had. A smile crossed his face when he recalled the heartfelt thank you from Jennifer. That simple acknowledgment of his worth made all the humiliation he was subjected to miniscule in comparison to the satisfaction he felt. Whereas yesterday he was dressed like and sissy in pink panties and a cock cage, today he was wearing gray flannel dress slacks with a navy blazer and crisp blue shirt under his raincoat, like someone headed to the country club for Saturday lunch (though he was wearing the blue frilly panties and the lacy halter bra that were in the bag marked "Friday").
The car brought him north on a winding road running alongside a rushing river to a brick house set back in the dense stand of tall trees. The car pulled up next to the house. The driver ignored him as he disembarked the vehicle. The tall trees were dripping large drops of rain on him as he sought the cover of the house. He could smell the damp air, and it reminded him of the happier days of his youth and his visits to summer camp. As instructed, he found his way around to the side door. It was located on a small porch with a modest V-shaped overhang that provided a partial cover from the large drops. He rang the bell, hoping this was the right place. There was no answer for several minutes. The temporary glow of his memory was replaced by anxiety as the rain drops cascaded off the porch roof and onto the shoulders of his raincoat. He was relieved when Jennifer opened the door; she was casually dressed but angrier than the day before. He was crestfallen to see that he had clearly not won her over.
She did not invite him in, but let him stand on the porch with the rain continuing to splash on his raincoat and now his head.
"You again. Don't get your hopes up. I did make Mistress Elaine cum when she watched the video. So you did not win Mistress's little bet. I ended up getting punished severely anyway, thanks to your stupid fantasy. Here, everything off and in the basket - - and put on what's in this bag." She leaned against the door frame and watched as he stripped and put his carefully folded clothes, undergarments and then his socks and shoes in the basket, as if he was expecting to be graded on his work. The small bag (labeled "Saturday") she handed him had bright red thong panties and a matching red halter bra. She watched as he pulled on the panties. He struggled with the hooks on the bra behind him. She didn't move a muscle to assist him. It took several minutes of gyrations to finally get the two hooks into the corresponding eyes. He was now shivering as the rain was now pelting his almost naked body and his bare feet were standing in a thin layer water on a cold concrete surface. Satisfied with his appearance, she handed him the collar, leash and leather cuffs he wore the previous day. He again struggled with the collar. She was amused by his struggles and his discomfort, which were small recompense for the punishment Mistress Elaine had meted out that morning on her defenseless bottom. Once finished, she clipped the cuffs so his hands were behind his back.
Wordlessly, Jennifer pivoted and walked into a small foyer. He entered the foyer and backed into the door to shut it. He had to walk quickly to keep up as Jennifer led him down the hall of Mistress Elaine's house on the leash, awkward with his hands cuffed behind him. They turned into a breakfast room, with comfortable furnishings and a large multi-paned bay window looking out onto the rainy back garden. There was a modern kitchen beyond, and open French doors to a dining room. It was a warm country house, and the only thing out of place was him in his exposed costume.
"Here, slip these on to finish your ridiculous outfit." She pointed to a pair of shiny black high-heeled pumps on the floor, obviously in a large men's size, that showed slight wear from their previous occupants. With hands still cuffed behind him he had to work his bare damp feet into them, and once they were on he felt the odd sensation of standing on a slope with his hips and chest thrust forward. The pumps were at least a size too large, which made the effort of standing in them and walking that much harder for a novice.
Jennifer guided him to stand in the doorway, facing the garden, as she clipped the rings of the wrist and ankle cuffs to loops of cord she had wrapped around the hinges of the open French doors. In only a moment he was secured in an X position, standing in his heels, facing away from the door. He was surprised to see that his cock was erect given the position he now found himself in.
"You see, no need for a dungeon or special gear, but with the same effect. Now, pay attention!" She slapped his flank hard with her open hand, leaving his skin stinging. Jennifer knelt at the floor by his side and they waited in silence.
Mistress Elaine came in wearing a tweed skirt cut six inches above her knees, a tight thin cream colored cashmere sweater, and beige cut away pumps with three inch heels. "Ahhh . . . my two video stars, together again. I thought of you, Boxwood, as Jennifer licked me to an a quick orgasm last night. I could see that maybe there's more to your relationship with each other given Jennifer's real orgasm as you fucked her ass. So no, you did not win her services. And she ended up getting punished anyway for not treating you with respect while she was there. She was not authorized to pee in your lunch. Her bottom felt the sting of my cat for that infraction."
Jennifer glared at Boxwood when Mistress Elaine was lecturing him. He resigned himself to the fact that the goodwill earned yesterday was but a distant memory.
Mistress Elaine continued, "What you need to focus on for the next two days is learning to give, to offer your body rather than taking. I asked you to dress up today, just to heighten the contrast for you and where you are now. We'll work on those small tits of yours first."
She stepped closer to where he was spread out, cupping and massaging his breasts in the soft lace bra, then sliding her hand in to pinch and roll his nipples. As the nipples tightened, she pushed aside the bra to lick and suck them, raking her teeth and tugging on them. He shuddered and arched his back to push them toward her. Jennifer watched with annoyance.
"Lovely, you seem like an easy slut already. But I think you need to be bigger and more sensitive to really understand how to offer these. And we are ignoring your clit for now? " Mistress Elaine slapped the front of his panties and his hardening cock.
She reached into her pocket and held a small device for him to see - - a short wide clear plastic tube with a squeeze bulb. "With training we can make your nipples larger and more sensitive. Perhaps later I might decide to have them pierced and fitted with rings or bars to remind you of what you are. For now, we will just make a start in the right direction."
Fitting the tube over his right nipple, she held it in place as she pumped the bulb. He looked down as he felt the suction and saw the nub of his nipple pulled into the tube and extended. Tugging it toward her, she slipped an elastic band off the tube to hold the swollen nipple, then repeated the process on the left. She stepped back and smiled at the effect, with his two extended nipples, and flicked her finger at the right one, causing him significant pain.
"We'll just leave these on for 5 minutes now, but with repeated training you'll be able to take more and they will stay permanently larger."
She pulled his bra back up where the lace rubbed against his sensitive flesh. She ducked under his extended arm to walk behind him and as he tried to focus for a few minutes on the rain and the garden outside the windows. His attention snapped back as he felt his panties pulled down and her fingers with cold lube probe him from behind and a narrow plug pushed in. He felt the waistband pulled back up, then she stepped in front of him again holding out her phone.
