Sissy Sessions Ch. 02

Note to readers: Sissy Sessions is a collection of anthology-style short stories. I plan to write them so that each one is unique. I'll re-use characters in more than one entry from time to time. The plan is to write these stories so that you can read each one on its own. No need to read the series in order. I hope you enjoy, and if you do, please star and comment!

"The steak is excellent tonight," said George.

"Give the chef my compliments," he followed up without looking up from his plate.

"Yes, sir," the waitress responded as she curtsied.

The girl walked away from the table and towards the kitchen. Her patent leather black high heels clicked against the dining room floor. Jeanine's eyes wandered up the girl's legs. She admired the delicate outfit, from the black stockings up to the little black dress. It was a standard waitress uniform at the club. The girl also wore a rose-gold anklet around her left ankle. Her black bob haircut was the perfect length. Her hair stopped below her chin and rested above the black collar around the girl's neck. The tag on the collar is the shape of a plate with a fork and spoon on either side. All the waitresses wore the same tag. It lets the patrons know the girls are wait staff.

Wait staff are off-limits during working hours. Club rules.

Jeanine sipped on her wine.

"Darrell did a good job with that one," Jeanine said to her husband, George.

"I'm surprised he's not here tonight. I thought he loved this part of the initiation," she continued as she looked around the room.

"He's too busy with his latest bitch," George replied.

"The tenant?" Jeanine asked.

"Yeah, he thinks she'll be ready soon," George said as he reached for his glass of water.

The first Saturday of every month is Initiation Day at the country club. It's the only day prospective staff members can progress up the corporate ladder. All prospects are on their best behaviour on Initiation Day. You can see the eagerness in their eyes. They cannot afford any strikes on their record. Three strikes, and you're out.

This month, there are three prospects on the docket to perform. George and Jeanine missed the matinée. The daytime performance drew smaller crowds. Most club members are too busy during the day. The membership turnout for the matinée sits at around 30 percent. The dinnertime show draws around 55 percent of club members. George only has enough time for the dinnertime show tonight. He and Jeanine aren't able to stick around for the main event. The main event usually draws 70 percent membership turnout, at the least. It's not uncommon for upwards of 80 percent of club members to make an appearance at the main event.

The prospects' performances are like graduation events. Graduating from a main event performance means prospects can become full-fledged staff members.

Ellie is headlining the dinnertime show tonight. George fancies her. He cleared his schedule to make it to this show. He's had a thing for her since her introduction at the club. It was a coincidence that George happened to wrap up a game of tennis with Darrell when Max brought her in. It was George's load she swallowed to earn the first trinket for her anklet. Max and Darrell signed off as witnesses.

Little Ellie has an outstanding mouth. She's 5'2" and weighs 125 pounds. Her fiery red hair stood out against her pale white skin. George couldn't resist the sight of her freckled face looking up at him as she swallowed all 8 inches of him. Seeing her on her knees was almost as intoxicating as seeing her taut little balls. The way they hung between her legs while trapped in the chastity cage drove George wild.

It's been three months since George first met Ellie. He couldn't wait for her to strut her stuff out on the stage tonight. He was almost getting impatient.

"Ladies and gentlemen, please give it up for Max and Ellie!" Elena's voice filled the room from the microphone at the stage. She's the dinnertime show coordinator.

The lights in the dining room dimmed, and a spotlight shone on Max. All 6'2" of him walked down the designated laneway leading up to the stage. He wore a fancy robe with the club's initials emblazoned across the left side of the chest. You could hear the soft sounds on his slippers with each step.

Close behind Max was Ellie. The sound of her steps sounded distinctly different. A familiar click with each of her steps.

Jeanine took another sip of wine. She couldn't contain her smile.

Max stood at the top of the steps leading to the stage with his hand reaching down to help Ellie up.

Click. Click. Click.

Ellie's sparkly silver heels shone in the spotlight. It's all she wore. Well, other than her white chastity cage and butt plug. Ellie also has her anklet on. The white cages are standard for prospects. The pink plug means Ellie is deserving of headlining a dinnertime show.

Accompanying Max and Ellie on stage was another prospect, Maggie.

Maggie is 5'8" and weighs 165 pounds, but you can't tell as she kneels at the foot of the bed in the middle of the stage. She's wearing black heels and stockings. A matching black crop top covers her flat chest. No panties. Her butt plug is visible. It's purple.

Ellie and Maggie both have three trinkets on their anklets. They're not allowed to be part of the dinnertime show without them. Neither of them has a collar. They haven't earned them yet. If all goes well, Ellie will have hers by the end of the night.

Littered throughout the room are various other prospects. They're not visible, though. You can only tell if you know where to look. Their knees are visible under the tablecloths. It's evident what their task is from the growing smiles of the men and women seated at the tables. In fact, Josephine is the reason Jeanine couldn't contain her smile. The girl is working wonders with her tongue. Jeanine will be happy to sign off on a job well done at the end of the show. It will be Josephine's seventh positive approval. Three more, and she'll be able to replace her blue butt plug with a purple one.

Back on the stage, Maggie is sucking on Max. It's her duty as tonight's on-stage assistant. She's making love to the tip of Max's cock. It grows inch by inch in Maggie's hand as her tongue swirls around the mushroom-shaped tip. George is familiar with Maggie's talents. She's not as good as Ellie.

The other patrons are talking amongst themselves. Some are enjoying their meals; others are watching.

George is staring at Ellie.

"Oh, that's new. It looks like Max moved up to the charcoal-coloured ring. When did that happen?" asks Jeanine.

Max's charcoal cock ring is in full view, with his erection now standing at full mast.

"A couple of his girls left an impression here at the club over the last couple of weeks," said Elena. The show coordinator is now standing over George's shoulder, holding her tablet. She taps the screen a couple of times before looking back at George.

"You're up next, sir. You can make your way back to the prep room whenever you're ready," she told him.

"Excellent. Thank you, dear," replied George as he stood up.

"Are you okay here by yourself?" George asked his wife.

"Of course, dear! I have Josephine to keep me company. Go and have your fun, sweetie," Jeanine told her husband.

George patted his wife on the shoulder. Her hand met his for a quick embrace before he walked off to the prep room with Elena.

Jeanine turned her attention back to the stage as Josephine continued to lap away at her pussy. Maggie is now off to the side of the stage, near the steps. Max is taking Ellie from behind, as she's on all fours. He has a fist full of her red hair in his right hand. Her back arch is immaculate. Excellent form.

The room fills with the sounds of the sissy's moans. It escalates from a whimper when Max pulls out to a yelp whenever he bottoms out in her. As the one to introduce her to the club, Max is the first to use Ellie tonight. George is next up due to his status.

Every time Max bottoms out, the clapping of flesh echoes throughout the room.

Jeanine's fluids are flowing out of her pussy now. She loves Initiation Day.

Ellie is making eye contact with Jeanine. The sissy holds her gaze for as long as possible before it becomes too much. Max is holding her head down on the bed as he relentlessly rails her. It's too much to handle now, as she closes her eyes to revel in her pleasure. Her mouth forms a round O shape. Her body shifts forward a bit with each of Max's thrusts. He's putting his weight into it. He always had strong hips.

"Spread your cheeks for me, sweetheart," he says between grunts.

"Yes...ughh... Daddy mmmph.. oohhhh," replied the sissy.

Her hands darted out. She reached back and placed a palm on either butt cheek. Her fingers grip the tender flesh as she spreads herself open for Max.

"He's close," Jeanine thinks to herself. She's trying to hold back her own moans as Josephine ramps up her efforts.

"Slow down, bitch," Jeanine said with an annoyed tone.

"I want this to last," she continued. Josephine's pace slowed again. Jeanine did not care if the bitch was tiring.

While she was giving out her orders, she almost didn't notice George was now on the stage. His robe hung open, and Maggie was now between his legs. His hand was under her chin. It looked like he was petting her. It's almost like someone would scratch the chin of a dog. The gesture amused Jeanine.

"Uuurrhhhhh, fuck yeah, bitch," Max roared to a round of applause from the patrons. Jeanine joined as well.

Max pulled out of Ellie and snapped his fingers. Maggie pulled herself off George's cock and made her way to the bed. She started lapping up the cum seeping out of Ellie's hole. Max shook George's hand before leaving the stage. Ever the showman, he waved to the crowd as he made his way back to the prep room, where Elena stood.

Once cum no longer leaked from Ellie, Maggie took her place back on her knees beside the bed.

George crawled into the bed. You could see the affection in his eyes as he stared at Ellie, as if she were his prey. She was now seated on her bum. Her legs shifted as she crawled backwards towards the bed's headboard. Her hands were pushing herself further back. It looked like she was trying to squirm away from George. It almost looked like fear, except for the mischievous smile across her face. She bit her lower lip as she looked up at George. He's inching his way forward now.

He's leaning over her now. They're face-to-face. Nobody can hear what he's whispering in her ear as he leans down further.

Ellie nods her head.

"I said, do you understand?" George said as he raised his voice. His left hand pushes Ellie down into the bed. She attempts to get back up. She's on her elbows. George is kneeling between her legs, preventing her from closing them.

"Yes, sir!" Ellie responds before she lets out a brief shriek.

"Ahh" was the sound she made.

George had his right hand gripped around the poor sissy's balls. Her penis was locked away in the little white cage. A symbol of her former manhood. He snapped his fingers with his left hand.

Maggie's hands began to rub up and down the length of George's cock. She was slathering a generous amount of lube on him. When he was ready, he waved her off. Maggie reached for Ellie, but George stood her down. Instead, Maggie handed George the lube so he could prep Ellie himself.

He sank two fingers into her ass with ease as he took his time massaging Ellie's insides.

When she was ready, Maggie took the bottle away and resumed her place on her knees beside the bed.

Ellie placed her hands on the bed and raised her legs. She spread as wide as she could, enticing George to enter her.

"Flexibility needs some work," Jeanine thought.

In one full, slow stroke, George buried himself in Ellie's ass. All the way down to his onyx cock ring. It was Jeanine's turn to bite her lip. There's nothing like seeing her man dominate a sissy.

Ellie wrapped her legs around George's waist and had her arms around his neck as he plunged into her. He allowed her to remain in this position for a few strokes before he tore her arms off of his body. Jeanine knew this meant Ellie's hole was adjusting to George's cock.

Next, he placed his hands behind Ellie's knees to pry them open. She was reluctant to release her embrace at first. A stern look from George took away any remaining resistance. Her ankles were now in his hands as he pushed her legs back. The girl looked up in awe of George's power over her. Jeanine looked on in lust for her man.

He began his strokes again. Every stroke increased in pace until he was hammering away at her.

"Uhh, uh, uhh. nngghhh, OH!" was all the room could hear from Ellie as the patrons watched in silence. George is a fan favourite with the sissies at the club, and for good reason. Jeanine couldn't wait for her turn with his cock later tonight.

From the tip of his cock all the way down to his cock ring on every single stroke. All 8 inches. That's what Ellie was getting right now. Her eyes were practically rolling to the back of her head. She couldn't see straight. The sweat dripping off George's brow and landing on Ellie's chest brought her back to reality. This was the most intense sexual experience of her life.

She continued to moan. She couldn't stop herself if she wanted.

"Uhhh!" she exclaimed.

George hit her sweet spot.

"Ughhh" she moaned.

He hit the spot again.

One more time. The floodgates opened. The cum began to leak out of Ellie's caged cock. There was so much; it was sliding down her belly and starting to pool on the sheets.

"Elliot is gone; only Ellie now," George whispered down at Ellie.

Everyone in the crowd started cheering when they realized Ellie had cum. Everyone except Jeanine. She was too busy experiencing her own orgasm.

"Up. Good work, now go," Jeanine says as she sends away Josephine.

It's not long before George floods Ellie's newly minted pussy. Her second load of the night. George leaves himself buried inside of her. Allowing himself to soften up before he pulls out.

Maggie is fast at work.

Jeanine is there at the bottom of the stage's steps to congratulate George. She takes his hand to help him off the stage. He wraps an arm around her shoulder.

"Let's get home, baby; it's my turn," Jeanine says to her husband.