The Long Weekend Ch. 03

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Brunch in the City.
8.6k words
4.38
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Part 3 of the 4 part series

Updated 09/22/2022
Created 10/23/2007
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She woke first. He was curled up naked at her feet, as she had left him after she had released him from the plastic wrap cocoon last night. She had kept him in it for as long as she dared; finally removing his hood and cutting open the wrap after she had let him drink from her pussy. She had enjoyed both beating him and teasing him through the wrap, and then cutting little holes in it to tease and torment all his tender bits.

She was allowing herself to have hope for this candidate. The events she had planned for today would tell her more, a great deal more.

She glanced at the clock, and saw she had a little while to rest and reflect. She had had her way with him, and met with no significant resistance. He had desire and intelligence, but would he be able to juggle the delicate balance of personalities she required?

She needed a real man in her life for social functions and as an overall life partner. She wanted someone who could be presented with pride to her family, friends, neighbors, co-workers, and casual passers-by. He had to be a good man, fun to be with, and capable of both quick wit and intellectual discourse. He had to be helpful providing useful input for decision-making, yet ready to defer to her judgment...a good junior partner.

After months of e-mails and phone chats, she was pretty sure he was all of that.

On the other had, once they were behind closed doors, she needed him to be able to switch all that off and become trainable property, enslaved to her, completely soft and malleable, like putty in her hands. She wanted to bring out the soft and submissive side. She wanted to reach into his soul and extract his feminine side, expose it, nurture it, love it, and use it for her service and pleasure.

So far, he seemed open to that path...even willing.

What concerned her was his ability to handle the psychological stress of the process, and maintain a mental and emotional balance as the she reached deeper into his mind and soul. His missy persona might start leaking into his masculine persona, and she didn't want that. It had happened to a previous candidate, and that had ruined his value to her.

She needed both, and her slave would have to transition seamlessly from one persona to the other, almost on a moment's notice, and without leakage through the wall that would have to separate his two distinct halves.

Was he ready to handle that?

Was he ready to handle slavery? He was an experienced and skilled submissive, but was he ready to go past submission? Was he ready to be totally owned as her trainable property? Would he enjoy spending the rest of his life as her chattel? Or would it wear off after the initial excitement had died down?

Finally, could he handle an inter-racial relationship? There were all sorts of social pressures in a slat-and-pepper relationship generated by prejudice and bigotry that would manifest itself from both blacks and whites. Could he handle that, too?

Somehow, she had to determine the likely outcome to all of these questions before she collared him as a slave.

Today's events would tell her more. It was time to get things in motion.

She sat up, and gently stroked his brow. She was growing quite fond of him. She had to be to reveal so much of her own Dominant and sadistic sides. There were only a handful of men and women who she had trusted with that side of her. Sharing it with had seemed so natural, and had led her to go a lot further with him in the past thirty-six hours than she had originally planned.

She started running her fingers through his hair, enjoying the feel of it. He began to stir, and then opened his eyes.

"Good morning, pet," she said. "It's time to get up and serve your Goddess."

He smiled and nodded, and got out of bed and then knelt next to it. She had him repeat the drill from Saturday morning. He went to the kitchen to brew her coffee, serviced her as her toilet slave, delivered her first cup, and was finally released to "go potty" and brush his teeth. He returned to fetch a second cup for her, and then shaved and showered. He knelt naked as she showered, and then dried her whole body with his tongue. He helped her dress, and at her instruction, put on his street clothes over his corset, stockings and panties, after she had inserted the remote-controlled vibrating egg into his anus.

As they chatted casually about the weather and their mutual desire the read The Times and catch up on the news, they walked up to Sixth Avenue, and she led them north a couple of blocks to a discount clothing store.

"At the rate we're losing panties and stockings, we'd better stock up," she said. He laughed and agreed. She made him search through the panties and stockings for the right colors and sizes as she had fun with her remote control. He took it with grace and humor. There was just a wince and then a grin. They ended up buying a dozen panties, all in either black or red, some silky, some lacy. They bought an equal number of pairs of stockings...also black or red.

He carried the shopping bag as they exited the store and headed downtown toward her favorite sidewalk café. It was almost noon, and she decided she wanted brunch. They stopped at a newsstand and bought a Sunday Times, and in a few minutes they were being seated at an outside table. They pulled out the magazine section and began to collaborate doing the crossword.

When the waiter came by with two menus, she asked him for a third because she expecting another guest. He looked at her with a raised eyebrow, and she smiled sweetly and said "It's a surprise, baby."

A few moments later, Cheryl arrived and joined their table. She joined their joint effort at the crossword until the waiter arrived. Deborah ordered for all three of them. It surprised him that she ordered an omelet for him, and even a Bloody Mary. She glanced at him as she handed the menus to the waiter and said, "I'm full of surprises, aren't I?"

"One after the other," he replied, and they all laughed.

"You will find that virtue is always rewarded by me," she said with a significant smile. Cheryl giggled, and he smiled and nodded.

They ate and drank and laughed and worked on the crossword together. He was amazed by how much good, clean fun he was having. He was feeling a bit high from the effects of the Bloody Mary...ironic choice on her part...which she had insisted that he gulp down almost as fast as if it were a glass of pure tomato juice. On his empty stomach from his 36-hour forced-fast, and given the physical exertion of that period, the alcohol hit his bloodstream fast and hard. He knew enough by now to know that she meant him to get tipsy, and she had a reason for wanting it.

The waiter came by to suggest dessert, but Deborah waved him off, telling them that they would have dessert at her place.

On the walk home, she led them to a fresh produce store. She gestured to him and Cheryl to take a plastic basket from a stack at the entrance to the store and follow her as she selected melons, bunches of bananas, apples, pears, oranges, grapes, tomatoes and peppers. When she stopped at the cucumbers, she took extra care in their selection, and smiled sweetly at both of them as she placed one cucumber into each of their loaded baskets.

He got to carry the heavier bags of produce and Cheryl was assigned the shopping bag. The two women walked ahead of him arm-in-arm, whispering confidences and giggling together. He had no idea what was in store, but knew damned sure he wanted to find out.

Once they got to Deborah's place, he was ordered to put the bags on the kitchen counter, remove the tablecloth from table, and move the table to the center of the kitchen. Deborah told him to remove his street clothes and panties, and told Cheryl to "take it all off". Deborah then went into her bedroom.

He was a little disconcerted being alone with Cheryl as he undressed. Yes, she had seen him in his outfit the day before, but somehow having Mistress absent made it humiliating all over again. Cheryl wordlessly took off her clothes and sat in a chair, looking at him with a little smile.

Mistress Deborah returned with an oversized black handbag, which she put on the floor near the table. She was dressed in her black corset, stockings, panties and boots, and was obviously in a good mood. She reached into her bag and removed a cock cage and harness. She secured it around him, making certain the cage was snuggly imprisoning his flaccid penis and testicles. She grabbed a second kitchen chair, positioned it a few feet from the table, and beckoned him to sit in it. From her bag she removed three sets of cuffs. She used them to bind him to the chair...hands behind the back of the chair, and each ankle secured to the chair's back legs.

"We should make you pretty for our guest," Mistress said, and produced a tube of lipstick which she quickly applied to his lips. This caused him to blush, and both women laughed at his discomfort.

"You climb up and lie on the table," Deborah told Cheryl, who immediately and silently complied. The small, round butcher-block table top allowed her to rest her head at one end and her ass at the other, perpendicular to his line-of-sight. Her legs dangled over the edge, and her feet did not quite touch the floor.

Using leather restraints, Mistress Deborah bound each of Cheryl's wrists to the opposite ankle, which bent Cheryl's legs up, with her knees pointed outward, in a position resembling a trussed turkey waiting to be put into an oven. Deborah brought the first bag of produce from the counter to the table. She began by taking a small apple and inserting it between Cheryl's teeth, and then began arranging the fruit and vegetables on the table around Cheryl's bound and gagged body.

He realized that Deborah was recreating the painting they had seen at the Museum of Sex on Saturday. Cheryl had a passing resemblance to the model in the picture and it was close enough to be very arousing. That caused his cock to begin to grow...grow into the fine metal mesh that constituted the cock cage. He winced at the pain, which caused his erection to subside. However, the pain was not his main concern. He was miffed that it was Cheryl on that table, and not him. He very much wanted to be the centerpiece for Mistress' feast.

Deborah brought over the second bag of produce and began fussing with the arrangement of the fruit around Cheryl. When she finished, she took a digital camera out of her bag and began taking photos, first of Cheryl from every angle and range, and then a couple of shots of him bound in the chair wearing his corset, stockings, cock cage and lipstick.

"Speech restriction is loosened, slave," she told him, "but you may only give a direct answer to anything I ask you."

"Yes Mistress," he replied in a loud hoarse whisper, looking downward.

She walked over and lifted his head by grabbing a handful of his hair.

"Oh no," she said. "I want you to see this...all of it. Understood?"

"Yes Mistress, you want me to watch everything."

She let him go and walked to the side of the table opposite from where he sat. She wanted him to have a clear line of sight, and wanted to observe him throughout the scene.

She began by selecting one of the cucumbers and inserting it into Cheryl's pussy in one quick motion. Cheryl's quivered, her back arched slightly, and she groaned through her apple gag. He heard himself gasp, and then a sharp pain made him grunt as his sensitive cock head crushed against the wire mesh of his cage.

Deborah laughed. "Having sympathy pains, missy?" she asked, and pressed the button on her remote control, causing him to twist and shift his ass in the seat as the vibrating egg inside him shook his anal canal.

She clicked off the egg after a minute, and returned her attention to Cheryl.

"I want to devour you," she told Cheryl as their gazes locked. "I'm going to eat you alive, but first I'm going to tenderize you." Cheryl's eyes widened, and that made Deborah smile.

Deborah tucked one arm under Cheryl's raised legs and pushed them higher to better expose her buttocks. She began to spank Cheryl, starting soft and slow and gradually raising the speed and force of her blows. Cheryl closed her eyes and moaned past the apple gagging her.

He watched with growing fascination, in spite of the episodic pain caused when his penis began to stiffen and pushed the sensitive head against the cage's wire mesh. He desperately wanted to be in Cheryl's place, yet, it was almost hypnotic to watch Mistress inflict erotic pain on Cheryl. He had originally been ordered to watch; now, he could not tear his eyes away from the sight.

Deborah finished her spanking of Cheryl, and paused only to lean down and remove a wooden paddle from the bag. It was two feet long, with a six-inch handle, and made of hardwood into which a few holes had been drilled. When Cheryl saw it, she turned her head toward him and closed her eyes. He knew the sweet mixture of fear and anticipation that she must be feeling. He wished it were him in her place.

The paddle caused a loud "crack" when it landed on Cheryl's ass, causing her back to rise off the table and a cry of pain to penetrate her gag. As the strokes continued, he could see a small tear leak past her closed eyelid and slide down her cheek, followed by another, and another...and then he could hear her sobbing.

The paddling ended, and Deborah leaned over to gently kiss Cheryl's tears from her cheeks.

"Do you think she needs more tenderizing?" Deborah asked him.

"No, Mistress."

Deborah walked around to inspect Cheryl's buttocks, and nodded in agreement. She took a couple of pictures, and then removed the cucumber from Cheryl's pussy. It glistened with moisture. She walked it over to him and told him to clean it. He did.

"Taste good?" asked Deborah.

"Yes Mistress," he replied.

"Ummm, let me see," she said, and returned to the table. She leaned over and began to lick and suck and even chew lightly on Cheryl's pussy. Cheryl's body writhed sensuously, and her sobs turned to heavy and rapid breathing. Deborah began using her fingers to thrust into Cheryl's pussy as she simultaneously flicked her tongue lightly and rapidly across the exposed and helpless clit. There was a muffled scream and a shudder, and Mistress stopped.

Deborah then went to the refrigerator and returned to the table with a jar of chocolate syrup and a can of whipped cream. She smiled at Cheryl and said, "After all, you are supposed to be my dessert." She began with the syrup, pouring the thick brown liquid on Cheryl's bare skin in a line from her chin to her pussy lips, and then a circle around each nipple. She then made two circles of whipped cream closer to the nipples, and selected two cherries to crown the whipped cream and cover the nipples.

Deborah took another series of photos as he watched thin little streams of chocolate branch off and begin to creep down the sides of Cheryl's breasts and neck. He felt himself breathing hard just watching it. All he could think about was how much he wanted to be on that table, and be Mistress' dessert. He wondered why he wasn't. Why Cheryl instead of him? Of course, Cheryl had a passing resemblance to the model in the painting, and Mistress was taking photos, but.... He was growing to respect his Mistress, and he doubted that the answer was quite that simple or obvious.

His mind raced through other possibilities. Was she testing him? Yes, of course, but how and for what? Jealousy? Okay, he was a little jealous, but "envious" might be more accurate. That might be a possible reason, but what was the point of duplicating the "Cannibal Play" scene? She could have tested his jealousy in many other settings. Why this one?

As Deborah began licking the stream of chocolate starting at Cheryl's pussy and moving up her groin and belly, he thought he understood.

He had said something to Mistress at the Museum yesterday about wanting to be the girl in the exhibit picture. Was this her answer to that comment? If so, what was the answer? Was she saying his comment had been a little too obvious...too much "hint-hint"? Did she see it as an attempt to Top-from-the-bottom? Was he being punished for the suggestion? Or was she saying "you haven't earned it yet"?

He knew she would eventually tell him, but for the time being his bet was "you haven't earned it yet", and his second choice was "all of the above...and more". Deborah had now reached Cheryl's breasts. One at a time, she ate the cherries, smiling at the bound woman as she did. She began to suck the whipped cream and chocolate until she was sucking, licking and lightly chewing on Cheryl's naked tits and nipples, causing Cheryl to moan and shiver. Deborah's hand slipped down Cheryl's belly to her clit area, and Cheryl's shivers increased and soon groans replaced the moans.

He was transfixed, and even the painful prodding of his cock against the wire mesh did not distract him.

After Cheryl's orgasm, Deborah followed the chocolate trail up Cheryl's neck and chin. Deborah removed the apple from Cheryl's mouth, and began passionately kissing her as her fingers continued to touch Cheryl's groin and vagina until she achieved another climax.

Deborah left the room, leaving him alone with Cheryl. They exchanged smiles. He neither spoke to her nor looked away from her. Either would have violated Mistress' last standing orders, and he wasn't interested in disobeying her.

Deborah returned with her strap-on, and stopped by the chair to order him to lube her cock. Straining down and forward against his bonds, he licked at it as best he could. He had done oral on her cock before...more than once...but having someone else watching it embarrassed him and made him blush.

Deborah left him, and walked back to the table, positioning herself between Cheryl's legs.

"Beg for it," she said to Cheryl.

"Oh please fuck me, Mistress," said Cheryl in a low whine.

"Is that the best you can do?" demanded Deborah, giving Cheryl's ass a hard swat of with her hand. "Is that how you teach your sister slave to beg?" She added another swat.

"I beg you, Mistress!" Cheryl said. "Please fuck me with your cock! Oh, Mistress, please fuck my pussy and my ass! Please do it; I'll do anything to have you in me, please...."

"Anything?"

"Anything, Mistress...everything, please, please put it in me now."

Deborah slipped the strap-on into Cheryl softly and smoothly, and her rhythm was gentle and sweet as Cheryl continued to beg in a voice that got lower and dreamier...until the guttural incoherence that overtook her when orgasm racked her body.

He watched in envy as Mistress slid her cock from one hole and into the other. The sound from Cheryl was a loud sigh, followed by renewed begging. He could see that Mistress was close to climax herself. Cheryl's begging trailed off into soft sobbing as Mistress reached orgasm.

Mistress withdrew from her and walked around the table to give Cheryl another long kiss, and then whispered things into her ear that he could not hear.

They were both released. He was ordered to take the egg out, clean it and the strap-on dildo, and then to clean and straighten up the kitchen. Cheryl was ordered to take a shower. Mistress followed Cheryl to the bathroom. He went about his chores quickly. He wanted to be where they were, and he couldn't leave the kitchen until it was ready for inspection.

He returned the egg, dildo and the refilled oversized handbag to the bedroom. Mistress heard him and called him into the bathroom. She had stripped naked, and the sight of her curvy caramel body made his penis poke into the wire mesh again. Mistress instructed both of them to kneel on all fours, facing a low wooden stool which had been placed in front of the toilet bowl. She inserted an enema line into each of them, and placed her hand on both valves.