The Loser's Trophy - Cover

The Loser's Trophy

Copyright© 2023 by Xanzibar

Chapter 12: The Housewarming Party

Fiction Sex Story: Chapter 12: The Housewarming Party - Intense Hardcore Story, DO NOT READ UNLESS you are prepared for some messed up stuff. This story is cruel, mean,and sexy,but the universe it exist in a harsh universe. I basically let my mind go where the story takes it regardless of how dark it is and most likely,(not homicidal but definitely not romantic). A victim of bullying finally gets even with his tormentor only to find that he has already inflicted his greatest defeat before they even squared off. Through the instrument of his mother.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Blackmail   Coercion   Drunk/Drugged   Reluctant   Lesbian   Heterosexual   Fiction   School   Sports   Workplace   Cuckold   Mother   BDSM   DomSub   MaleDom   FemaleDom   Humiliation   Light Bond   Rough   Sadistic   Spanking   Gang Bang   Group Sex   Orgy   Interracial   Black Male   White Male   White Female   Hispanic Male   Anal Sex   Cream Pie   Double Penetration   Exhibitionism   Facial   Masturbation   Oral Sex   Squirting   Tit-Fucking   Voyeurism   Body Modification   Foot Fetish   Leg Fetish   Public Sex   ENF   Prostitution   Revenge   Transformation  

I secretly cursed at the world when I woke up every morning. The sounds of kissing constantly permeated from my mother’s bedroom. My most hated enemy had occupied my house and now was running everything, I ever cared about. I was nearing my limit when one house party lightened the load enough for me to see the other side.

Steve decided to have a party to help welcome him into his new house. I of course was responsible for all the preparations between going to school, and preparing my post high school life, my evil fucking bitch of girlfriend was responsible for taking me to the places to get the things needed for the trip.

Even when she was not just fucked by Steve she had me go down on her constantly. This shopping trip was no different. When we arrived at the parking lot for the rental place to rent the equipment for the party. I spent about forty-five minutes on my knees with my mouth thrusted into my girlfriends pussy and ass. She wanted to make sure that everyone knew I was taken when I went into the stores, because she could not exactly use my leash in public.

So, I had to act like the sheen on my face was from exertion. Several girls suppressed a giggle at me following behind my girlfriend with my face in such a state. But being embarrassed was the least of my problems. I became numb to her games. Which is why I think she kept making the sadistic nature of the games rise each time.

When I returned I was welcome by of my mother naked with her arms outstretched palms on the wall getting pounded senseless by Steve, “Whose pussy is this whore?” Steve growled out with a handful of my mother’s hair.

“Oh fuck! Yours, daddy! I love it! I love it so much! “ My mother screamed out.

“Tell me the day I fucking took you at my house, bitch!” Steve shouted at my mother.

“Best day of my life, Daddy, I love it! Fuck your bitch is cumming again!” My mother yelled exploding all over my bully’s cock.

“Whose cock is better!” Steve barked spanking her ass.

“Oh god yours!!!! Shit do not stop daddy!!” My mother was spitting out any perverted thing that came in her head. She fucked like a pornstar too.

Now I know, this really should not bother me, but I was hurt my mother said my bully’s cock was better than mine while fucking her. It was then I realized how mentally fucked I was going to be for the rest of my life.

My girlfriend, jealous of what had been going on lately, decided to make me eat her out again on the couch. I hated my life. Today was going to be rough I already knew it.

The Party

Pamela and Steve had me dressed for the party. Pamela had me wear a French maid’s apron and cap and nothing else but a slave collar around my neck. I was to be their beer bitch amongst other things. The doorbell rang and I was told the answer the door, I did not want to, but I lowered my head and walked over to the door. What greeted me almost made me feint on the spot.

Across from me Cyntha Simmons answered the door.

My high school principal. She stood tall in her 4-inch red stilettos, her leather miniskirt barely covering her thighs. Her white blouse was unbuttoned to reveal a lace bra underneath. I could feel my knees shaking as she approached me with an intimidating gaze. Her hair had been made to look wet. My cock saluted her. I tried not to act like I was not entirely naked except a maid’s apron, but it was impossible I saw in her eyes that we were both caught in this sick web. Steve did not only have my mother under control but the woman who expelled him from my high school when I was a freshman.

“Come in slut, I see you met your student.” Steve said, taking a swig out of his beer and smirked at her. Mrs. Simmons heels clicked on the hardwood floor of our foyer before answering, “Yes, Master, I came I hope you approve of my dress?” She said submissively, she was already blushing deep red.

“Tommy boy ... did not know she looked that hot under those guys clothes huh. “Steve called out to no one in particular. “You know Cynthia ... I bet you did not know one of Frankie’s many talents include cunnilingus, I think you should try him out.”

“Thank you, Sir, but ... he is my student...” Mrs. Simmons tried to explain to Steve. Steve grew angry at that response, “I do not care, slut, sit down on the couch and let him show you?”

“Yes ... Sir” Mrs. Simmons said as she slowly walked in defeat to the couch. Pamela snapped her fingers and pointed to the floor. I knelt on the floor, as she pulled my leash, and I followed her on all fours like a dog. She walked right up to Mrs. Simmons.

“Sit down, whore, and let my boy show you how a cucked out lil bitch properly pleasures a woman,” Pamela commanded, her voice dripping with contempt.

Mrs. Simmons, unable to defy the authority of both Pamela and Steve, reluctantly sat down on the couch. I positioned myself between her legs, my face mere inches away from her pussy. I could feel her pulse quickening and her breath becoming shallower.

“Now, show her how to really please a woman, boy,” Pamela taunted.

Reluctantly, I leaned over and picked up Mrs. Simmons’ high heeled foot and licked her ankle followed by suckles. I took a deep breath as I made it a point to map the entire contour of her calf with my lips and tongue, her legs were magnificent and sexy. I was rock hard.

Mrs. Simmons was excited too I was at her mid-thigh when I tasted her juices and I could smell her pussy the closer I got, she was soaked and very turned on. I began to lick and kiss at Mrs. Simmons’ inner thighs, working my way closer and closer to her pussy. She squirmed and moaned as I continued, her embarrassment and humiliation almost palpable.

Finally, I reached her clit and began to flick my tongue, teasing and tantalizing her. I could feel her body begin to tense beneath my touches, and I knew it would not be long before she came. Pamela had been right; I was indeed talented when it came to orally pleasing women. Mrs. Simmons grabbed my hair hard as her body started to feel the effects of my tongue licking her clit.

My principal’s smooth thighs locked around both my ears like a vice. “Oh Frank, I’ve never been treated like this before!” she whispered hoarsely, trembling with excitement. Her eyes were closed, and her mouth was open in a silent scream of pleasure.

Steve watched with a twisted grin on his face, stroking his hard cock with his free hand. “Keep going, boy, make sure she has a good time. We want to see that pretty face of yours buried deep in her cunt.”

I could not believe what I was doing, but I knew better than to defy their commands. With renewed determination, I dove back into my task, lapping at her clit and probing her wet folds with my tongue. Mrs. Simmons’ moans grew louder, her thighs quivering around my head. I could sense her orgasm was close, her entire body trembling with anticipation.

As I continued to work my magic, Mrs. Simmons’ moans turned into a

high-pitched scream. Her body stiffened, and I could feel her juices gush over my face. She was cumming hard, her thighs gripping my head tightly. I tried not to think about the fact that I was eating my high school principal’s pussy while my mom and principal’s husband watched.

Pamela squealed with delight, clapping her hands in glee. “You did it! You made her cum! Oh, look at the mess you made!” she said, pointing at my face.

Steve smirked, stroking his cock faster. “That’s right, boy. Show her who is in charge. Make her beg for more.”

Mrs. Simmons, still panting from her climax, looked at me with a mix of horror and gratitude. “Oh my god, I ... I can’t believe I just ... I...” she stammered; her voice barely audible.

Steve chuckled and took another swig of his beer. “Good work, boy,” he said. “Now make sure to clean up any mess you’ve made.”

I obliged, using my tongue to lick up every drop of Mrs. Simmons’ juices from her quivering flesh. It was a task I could have continued for hours I have performed cunnilingus more times than I could count, but I knew better than to disobey.

As I pulled away, Mrs. Simmons gasped for breath, her face flushed and her eyes wide. “Oh my God, what have I done.”

For a moment, the four of us remained frozen in place, basking in the afterglow of the experience. But it was soon broken when Steve clapped his hands, signaling for the next round of degradation to begin.

“Alright, everyone,” he said, taking a swig of his beer. “Now your mom’s next boy. You need to show her proper respect.” Steve said, I sighed. Pamela and Steve have been making my mother behave more dominant towards me when I orally pleased her.

I was led on a leash over to my mother’s creamy legs I bent down and kissed her foot, a ritual that recently got added to my humiliation oral obligations of cleaning out my mother. I licked the side of her heel. Then proceeded to kiss and lick her ankle slowly. My mother moaned especially when opened my lips and suckled the inner part of her thigh right above the knee.

By the time I reached her pussy, I could feel the weight of my bully’s influence in every taste. Closing my eyes, I braced myself to endure. But as always, everything changed when I reached my mom’s clit. She grabbed the back of my head, guiding me with an iron grip. “That’s it,” she commanded, her voice steady and authoritative. “Don’t stop until I say so.”

I sucked hard and devoured her like a madman, driven by a strange mixture of guilt and compulsion. Each flick of my tongue was met with her approving moans, and despite the humiliation and disgust boiling within me, I could not help but obey. My efforts were no longer just about survival; they were about meeting the demands of Steve, Pamela, and most importantly, my mother.

“I will survive this hell,” I screamed internally while continuing to pleasure her.

As her body tensed beneath me, she tightened her grip on my hair and pushed me further against her. “Right there,” she ordered, her breath hitching. With renewed intensity, I focused on her clit and slipped a thumb over her G-spot. Her cry of pleasure resonated in the room as her orgasm crashed over her like a tidal wave, leaving me trembling in its wake.

I pulled away, unable to meet anyone’s gaze. My face was flushed, and my heart pounded in my chest. I felt like I might vomit or faint. But before I could recover, Steve snapped his fingers and signaled for the next round of degradation.

“All right, everyone,” he said, I turned around and more people had arrived at the party. All the guests were greeted with the sight of me naked on my hands and knees eating out my own mother. There were more women who arrived, all were dressed like sluts of the highest order, and all had thugs with them. I recognized Mrs. Glendale from the bus video, she was dressed in golden heels, golden collar, a chain outfit that covered nothing. She was walking over to the gentlemen who she tried to call the cops on. She got down on her knees and leaned forward and was bobbing up and down his cock.

Pamela looked at the high sheen on my face. “Don’t you dare wipe it off bitch.” My ex-girlfriend then curled her finger towards her. I knew what she wanted because I just gave it to the woman before me.

Pamela laughed cruelly as she watched me crawl towards her, my face still glistening with my mother’s juices. She spread her legs wide and gestured for me to start at her feet.

“Clean them up, slut,” she sneered, her tone dripping with contempt.

Without hesitation, I began licking up the sticky residue from the bottom of her heels. Each swipe of my tongue elicited a sadistic chuckle from Pamela as she watched me humiliate myself further.

I moved up to her ankles and calves, lapping at the sweat and dirt that had accumulated on her skin. My stomach churned with disgust, but I forced myself to continue, driven by a strange mix of fear and arousal.

When I reached her thighs, Pamela spread them wider, giving me full access to her most intimate area. With a wicked gleam in her eye, she commanded me to use my teeth.

I hesitated for a moment, but the sharp tug on my hair reminded me of the consequences of disobedience. So, with trembling hands, I sunk my teeth into the soft flesh of Pamela’s inner thigh and dragged them upwards. She let out a moan and bucked her hips against my face, urging me on.

I bit down harder and continued to grind my teeth into her skin as I made my way closer to her core. Despite myself, I couldn’t help but feel a surge of exhilaration at being allowed such dominance over this woman who had once controlled every aspect of my life.

Pamela lay panting and sated on the bed as I knelt beside her, still catching my own breath. A part of me was disgusted by what I had just done, but another part couldn’t deny the intense pleasure that came with submitting to Pamela’s every whim.

She reached out and stroked my hair fondly, an uncharacteristically gentle gesture from the usually cold and calculating woman. “Good boy,” she purred, a hint of genuine affection in her voice.

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