Chapter 3: Anal Orgy

Kit desperately wanted to hold Jack’s hand as they walked down the hotel hallway from her room to his. There was no way to describe how elated she felt. Jack understood her needs, no, more than that, he exorcized the restraints holding her back. Pent-up sexual urges were freed and she rejoiced in being “normal” again. He was incredible, exactly what she needed and wanted. Now she had to keep Jack satisfied and interested in her. That’s how she lost her first Master.

At the age of fourteen, Kit became involved with her first Master. Mr. M. was her next-door neighbor, an older man in his fifties. With the intent to show her something special, she thought it was strange but she trusted him. He led her by the hand down wooden stairs to his basement “playroom.”

Kit’s eyes went wide when she entered a sealed-off soundproof room. His wife was naked and hung from metal hooks in the ceiling joists. Ropes attached to her wrists kept her arms over her head and a metal bar attached to her ankles kept her legs apart. Mrs. M. smiled at her and looked at peace. Momentarily dazed, Kit stood there taking it all in instead of immediately running away.

“Hi, Kit,” she said. “Don’t worry, I’m fine.”

“H-hi, Mrs. M.”

Kit’s eyes raced up and down her neighbor’s naked body. Mrs. M’s breasts were smaller than hers and she didn’t have any hair between her legs, she was a big woman, and rolls of fat waterfalled down. Kit jumped when Mr. M. used a hand on her back to push her closer.

“Go ahead and touch me,” Mrs. M. said. “I want you to.”

“She’s still a child,” Mr. M said judging Kit’s reactions. “But I think she wants to learn more. Isn’t that right baby girl?”

Kit’s hand was guided up to Mrs. M.’s breast. She squeezed the soft flesh and her hand was then directed to Mrs. M.’s hairless slit. Her finger eased into the folds, finding moisture. Kit looked at her hand as Mr. M. moved it into his wife’s pussy. She watched as her finger disappeared inside and then came back out. Her fingers were coated in a thin secretion.

“Smell her juices,” Mr. M. ordered. He lifted her hand to her nose.

Kit took a deep breath. When it touched her lips Mr. M. told her to suck her finger clean. Kit’s mind swirled in confused excitement, she liked the taste.

“I want you to lick her cunt,” he said. “I know you want to.”

Kit hesitated. Mr. M.’s eyes hypnotized her. He came across as a dominant man sure of himself, and she found herself drawn to his aura. They spent many hours talking about sex and she told him she was still a virgin.

Mr. M. moved Kit’s face closer to his wife’s mound. With a hand on the back of her neck, he firmly pushed her forward. “Use your tongue in her cunt.”

Kit closed her eyes. The earthy smell was intoxicating, the tip of her tongue touched her pussy lips and her nose touched her fat belly. The taste was sweet and a little sour. Her tongue slid easily up and down, parting her labia. When her clit was exposed Kit felt his hand return to her head. Only then did she realize she wasn’t being forced.

“Suck her mini cock into your mouth, baby girl.”

Her lips surrounded the hard button and she sucked, making Mrs. M. moan. Kit felt a rush, her heart racing. Her knees went weak. Her body was tingling all over. She wrapped her arms around Mrs. M’s bum to stop her from swaying.

“Oh yes,” Mrs. M. gasped, “just like that!”

Kit sucked and licked until Mrs. M. screamed, “Don’t stop! Oh gods don’t stop!”

Kit didn’t and a gush of liquid poured into her mouth. Mrs. M.’s pussy tightened against her tongue and Kit held her in place, her arms squeezing the woman’s large bottom.

Mr. M. reached down and pinched Kit’s hard nipples through her thin top as his wife exploded. “That’s it, baby girl. Eat that cunt! Make her squirt!”

The orgasm lasted a few seconds but to Kit, it seemed to go on forever. Her breathing became faster she didn’t stop licking until Mr. M. pulled her head back. Her chin was covered with Mrs. M.’s juices. She licked her lips and swallowed, savoring the flavor.

“Thank you, Kit,” Mrs. M. exclaimed. “I can’t wait to return the favor.”

“You’re a natural,” Mr. M. praised. “Look at the size of your nipples, you loved being a sub.”

Kit didn’t know what a sub was. “Uh ... um ... I don’t know.”

“That’s okay,” he said, “there’s plenty of time for you to figure out what you like.”

Rather than running away, Kit watched as he punished his wife with a riding crop. Kit knew about sex, but she didn’t know sexual pleasure could include pain and submission. That was the start of her journey to the world of BDSM.

Mr. M. showed her a new world, one that she accepted with eagerness. He taught her that sex was much more than just fucking. She engaged in consensual erotic activity with a sense of enthusiasm. He gave her a safe word to use if needed, but Kit chose to never use it.

She called him Master in private and derived pleasure from him inflicting pain or humiliation on her while she was bound or restrained. Sexual penetration wasn’t expected, she had to earn his cock. Together with Mrs. M., Kit learned how to please a man and a woman.

Master took her to a sex club and she was the star of the show. Everyone wanted to get to know the extremely young girl with big tits who never said no to any perversity. She submitted to public flagellation and wild orgies. The club members cheered as her body exploded with multiple orgasms.

When she wasn’t required to perform in front of others Master M. found ways to push her further and further into submission with humiliation and pain. Kit loved every second of it, submitting to whatever his whims demanded. She opened herself up to him and found sensual pleasures in pleasing her Master. As Kit left her teen years, she entered into a lifestyle of submission with full abandonment.

One day Master M. brought home a young blonde girl to replace her and Kit’s life fell apart. Master had grown tired of her. Kit cried and begged to stay but he passed her on to a new Master from the club. This man was cruel and overly sadistic and Kit knew if she didn’t leave him, he would kill her. And so the journey for a new Master began. Man after man and even a woman, but none of them were the right fit.

As a submissive woman, Kit derived sexual pleasure and emotional gratification from relinquishing control and sexually satisfying her dominant partner. She needed to be obedient no matter the type of sex act that was forced upon her or she had to commit.

Thinking she could abolish her demons with a decent man, Kit married a guy she met in college. She tried to be a good wife, but the boring sex drove her crazy. She longed to be taken with force, to obey commands, and to experience true lust again.

Separated from her husband, Kit returned to the sex club to find relief at the hands of others. But deep in her heart, she yearned to find a new Master, one who would love her and control her.

Kit heard the rumors in school about Jack from her female students. His prowess and cock size made him a legend. But mostly it was the talk of how aggressive he was in bed that drew her to him. Kit didn’t care if it was wrong or illegal, and she set a plan in motion. But Jack caught on and quickly took control.

And now that she experienced his passion and aggression, she was hooked on him like a junkie. Jack was her drug of choice and hopefully her new Master.

Kit knew in her heart and body that Jack was her destiny. He was exactly what she needed and craved and she would do anything to stay at his side. Even if that meant losing her job as a high school teacher.

Jack walked slightly in front of her and she felt naked in his wake. They were headed to the outdoor common pool down in the hotel courtyard. She was about to be exposed to all her students, along with her secret life. Her nervousness only added to her sexual excitement of exhibitionism.

Jack ordered her to wear the small white bikini she bought as a joke, never thinking she would wear it. Her massive breasts were mostly exposed with only her hard nipples covered by tiny triangles. The bottom was just as small and Jack roughly yanked it up and wedged the material between her ass cheeks and pussy lips. The cover-up she wore over the tiny white bikini was see-through, and all it did was emphasize her assets.

When they arrived at his room, she followed Jack in like a good little sub. Neither of them expected what greeted them. Jack’s best friend, Logan was on the bed with Sylvia. Kit knew Sylvia was head over heels in love with Jack, but he didn’t feel the same about her. They were naked on the bed, and Sylvia’s young mouth was greedily sucking on Logan’s cock.

Both of them shrieked out at the surprise. Jack’s laughter quickly followed their worried looks.

“Well, this is a surprise!” Jack exclaimed. He walked closer to the bed, and Kit hid her body behind him. Everyone felt uneasy, except for Jack; he was loving the moment. Logan and Sylvia were trying to cover up their nakedness from Coach.

“Logan has a decent cock, nowhere near as big as mine, but still a nice one. Move your hands, Logan.”

Logan’s erection had diminished down to a floppy small sausage.

“What do you think?” Jack asked turning to Kit.

Kit wanted to run, bolt from the room. “It’s nice, Jack.”

“Stroke his cock, Sylvia, show Kit how big it gets.”

“I’m sorry, Jack,” Sylvia said. Her eyes stayed on Jack while her hand reached out. “You’re not mad at me, are you?” Even though she loved Jack, he only used her body whenever the urge hit him. She didn’t mind being a convenient slut for him and hoped one day that would change. “Logan and I just...” She couldn’t finish the sentence.

Jack gave Logan a hard look. “No big deal,” Jack responded but he was disappointed in Logan. Sylvia was already beating herself up, so he didn’t need to scold her more.

Now that Logan was over the shock of being discovered, he noticed what Coach Chatham was wearing. “Holy fuck! Coach is almost naked!” he blurted out.

Jack was proud of Kit, she obeyed him without complaining. With a smile on his face. He brushed her hair off her red cheeks and gave her a wink.

Kit blushed; the attention was intoxicating as Logan and Sylvia admired her body. But it was Jack she wanted to please.

“Take off your cover-up and show them your sexy body.”

Kit hesitated briefly. Her eyes fixed on Jack’s. He was her new Master, and she had to obey him. The thin top dropped to the floor, and she waited for his next command.

“See!” Jack spun Kit around so his friends could see both sides. “Have you ever seen a more beautiful woman? And this ass is so firm!” he boasted as he gave her a hard slap. He turned her back to him and looked into her eyes. “I haven’t fucked her ass yet. I’m saving that for later tonight.”

Kit lost herself in his deep brown eyes. “I can’t wait,” she whispered. The desire to feel Master’s large cock buggering her ass was overwhelming.

Logan’s cock hardened, this time from staring at his teacher. “You fucked her?” Logan asked in disbelief. If not for Jack, he would still be a virgin. He owed Jack for all the leftovers and sloppy seconds that came his way. In Logan’s mind, Jack was a god.

Jack drew Kit into his arms and she melted against him. “I got to know some of Coach’s secrets. And, yes, we fucked!” Jack’s hand reached down to her barely covered breast, and he pinched her nipple. “Isn’t that right, Kitten?”

There was no escape plan; Kit brought this on herself by throwing herself at Jack on the bus. But she didn’t want to escape, she wanted to continue and see where he took her. “Yes, you know more about me than any other man.”

Jack raised Kit’s chin. Her soft dewy eyes showed nothing but obedience. “Don’t worry, we are all friends here.”

“I believe you,” Kit answered. She knew it was dangerous being in a hotel room barely clothed with students from her school. But she couldn’t disobey her Master.

“What do you say?” Jack challenged, directing his words to Logan and Sylvia. “Do you promise to keep this a secret?”

Sylvia never guessed Coach Chatham would fall for Jack’s charms and cock. She wished he looked at her like that. She lowered her arms exposing her tits and pussy. “I promise not to say anything, Jack.”

“Me too!” Logan echoed unable to tear his eyes away from Coach’s mature sexy body. He had never seen a live near-naked “woman” before, only on a computer.

Kit sighed in relief; she had to trust them. Her life was now under Jack’s control. “Thank you,” she said.

Sylvia admired her teacher. “I wish my tits were as big as yours!”

“Yours are very firm, and you have long nipples,” Kit replied.

Sylvia grabbed her tits and tried to give them a shake, “I bet yours shake and sway.”

Jack stepped behind Kit and groped her tits. He took control and bounced them up and down. He pulled the tiny triangles of material down, exposing her full breasts to Logan and Sylvia. “Kitten likes it when I pinch her nipples hard. I mean really hard.” Jack’s kisses on her neck melted Kit, and she closed her eyes. She liked to have other people watching and joining in. She hoped Jack would fuck her in front of them. His fingers manipulated her sore nipples, making her body come alive and her hips swayed seductively.

Logan reached over and rudely pulled Sylvia closer. “Wow! Suck my cock, while I watch.”

Sylvia looked at Jack for permission; she laid down in Logan’s lap after Jack nodded. Half-heartedly she performed oral more interested in pleasing Jack than Logan.

“Sorry about Sylvia and me. It just happened.” Logan confessed. “She was horny and wanted to come up here.”

Sylvia made a face and shook her head no, she wanted to find Jack, that is why she suggested coming up. After sucking his cock on the bus and eating his cum, she wanted to feel him inside her again. Then Logan got her worked up and they ended up naked on the bed. She didn’t mind fucking Logan now and then, but she only did it to stay close to Jack.

Jack wasn’t amused at Logan’s excuse. “You should have asked me first,” he said harshly. “You know I think Sylvia is special.”

Logan shrunk at being admonished, but Sylvia came alive at Jack’s words. She sucked Logan’s cock with gusto, but her eyes never left Jack’s.

Jack had a finger in Kit’s pussy and a grip on her nipple. She leaned back into his body and he kissed the back of her neck as Sylvia performed for him. The thought of having both girls worshipping his cock excited him.

“Move over, and we will join you on the bed. Kit, finish taking your swimsuit off.”

Sylvia stopped sucking Logan’s cock to watch her teacher and track coach get naked in front of them. She saw the significant love mark on Coach’s left tit. Jack did that to every girl he fucked, it was his way of branding them. In the showers after the gym class when a girl proudly lifted her breast to all the laughing girls it was proof Jack had claimed her pussy. Every girl wanted to be the next one to fuck Jack and his incredible cock.

Kit stood naked in front of everyone and, with a deep breath, did her best to relax. Her body ached sweetly from all of Jack’s abuse and she felt herself getting aroused and wet.

“Put one leg on the bed and show them your swollen cunt,” Jack ordered.

A bite mark was visible on her inner leg. “Did the bite hurt?” asked Sylvia.

When Kit submissively shook her head no, Jack laughed, “Kitten likes pain. She screamed like crazy but loved every minute.” Jack reached between Kit’s legs and explored her folds. “She loves my big cock in her tight cunt!”

The humiliation of being fingered in front of Logan and Sylvia made her leak. Kit celebrated the bittersweet circumstances. She had longed for Jack to fuck her, and to take control. Her fantasies came true. Except her submissiveness now included others who could destroy her life and career.

“Your turn, Sylvia,” Jack motioned. “Come sit on the edge of the bed.”

Sylvia looked at Jack in shock. She had never touched another girl down there. The beauty of her teacher’s pussy captivated Sylvia as she approached.

Kit cooperated by thrusting her hips forward. “It’s okay, Sylvia; I want you to.” Kit thought back to the first time she fingered Mrs. M.’s cunt, she was even younger than Sylvia.

Jack nuzzled Kit’s neck and played with her nipples. “Hmm, you sexy, woman,” he murmured.

Sylvia’s fingers gently touched her teacher’s pussy. The only other pussy she felt was her own. “Wow, it feels so soft!”

Jack and Sylvia jointly elicited moans of pleasure from Kit. Sylvia smiled at Jack, and he blew her a kiss.

“She likes this Sylvia; she likes the attention,” Jack claimed. “Use two fingers.”

Kit’s eyes met her students. “Yes, Sylvia, that feels good! Go deeper! Curl your fingers up!”

The moment stretched on as they manipulated Kit’s body. Encouraged, Sylvia concentrated on her teacher’s swollen flaps. Rather than being repulsed, Sylvia found herself curious. The smell wafting towards her joined her other senses.

Sylvia had touched a girl’s breasts at a slumber party as a dare, but this was different. She looked into her teacher’s eyes in disbelief, barely comprehending what was happening.

Kit’s mind wandered from daydreaming to self-reflection, to worry. Her sacrifice for physical pleasure and mental serenity left her vulnerable to Jack and now his friends.

Jack wanted to push Sylvia further. “Stand up and feel Kit’s breasts.”

Sylvia smelled her wet fingers and tentatively tasted them. Noticing the taste was similar to hers. Standing, she stood eye to eye with her teacher. Sylvia lifted each breast, surprised at how heavy they were. It made her think maybe she did not want big tits after all.

“Kiss them for me,” Kit urged. “Suck on my nipples.”

Sylvia looked at Jack and then at her teacher. No one said anything.

Jack smiled when Sylvia obediently lowered her head. He sucked his index finger, getting it nice and wet, then reached down to Kit’s ass. He pushed in slowly.

“Fuck!” Kit cried out, “Jack has his finger in my ass!”

“Enjoy it, Kitten; soon, it will be my cock!”