The Last High School Bullying

Lennard came home with a bruised eye, a scraped chin and a cut on his lip. His t-shirt was torn and his arms were scratched. Andrea found him cleaning himself up in the bathroom and rushed over to him.

"Oh my God, Lenny," she gasped, "Gosh, he really didn't hold back this time... It's even worse than before!"

Lennard nodded as he dabbed at the blood around his mouth. He took off his shirt, revealing a few bruises on his chest and stomach. The sight of them made Andrea's heart skip a beat and she felt tears start to well up in her eyes.

"Oh my poor baby!" she cried, "You're so brave... I'm so proud of you."

She got her son a warm towel, cleaned his wounds and helped him into a fresh t-shirt. He started sobbing.

"I know, baby, I know... Let it all out," she said, and held him close until he calmed down enough to tell her what had happened.

"He jumped me in the parking lot," Lennard said quietly, "I... I don't understand why he does this to me... I... I hate him so much."

"I know, sweetie," Andrea whispered, stroking his hair, "It's okay now. You're safe now. This is the last week. Remember, after graduation, you won't have to deal with him anymore, baby. You won't have to worry about him ever again. It will be a fresh new start in college, right sweetie? Everything's going to change in college!"

Lennard silently nodded.

"You are so brave, Lenny, so brave," Andrea said, gently ruffling his hair and giving him a motherly kiss on the head, "Okay... Now I'll have get ready, sweetheart. I don't want to keep him waiting. You know he can get very impatient."

"Mom..." Lennard looked at her, wiping away the last of his tears, "Can't you just ignore him...? Just once... Just this last time... Please?"

"Oh Lenny, we have talked about this," Andrea sighed, "this is between him and me. Besides, it's only this one last time, and then he will leave you alone forever. If I ignored him now, it would have all been for nothing. Do you want that? Do you want him to come back for more? To keep tormenting you through college? And it's not like he is hurting me, honey. I told you, he is treating me well, baby, don't worry."

"B-But Mom, he didn't even go easy on me this time! A-and we don't even know if we will end up in the same college-"

"Lenny, he is the one of the most anticipated quarterbacks in the state. They are basically drowning him in athletic scholarship offers, " Andrea replied, "and he did go easy on you before, didn't he? He also kept it down to once a week, just like he promised. He... He just got a little carried away today because it's the last time, that's all... Sweetie, please don't make this more difficult than it already is."

"But Mom-"

"No more buts, Lenny,", Andrea interrupted and put her finger to her son's injured lips, "Please, I don't have time for this now. Can you just help me get ready, honey? Please? Let's not test his patience. Just help me get ready and then you can watch TV or play video games, okay?"

Lennard reluctantly agreed. Andrea gave him one more hug and kissed him on the head, before she moved to the sink and started applying her make-up in the bathroom mirror. He stood beside her watching her reflection and catching a glimpse of his bruised face next to hers.

"Your father is going to be so angry when he sees that," she said, "Maybe we should cover some of it up later."

Lennard didn't answer.

"Lenny, don't worry," Andrea continued, "he won't find out."

"What if he does?" Lennard asked, his voice cracking, "What if he finds out about you and-"

"Then I'll deal with him," Andrea cut him off, "I told you, don't worry, sweetheart. Okay, what color did Jake say?"

"P... Purple," Lennard reluctantly muttered.

"I see. Sweetie, can you go get it for me, while I finish up my make-up?"

Lennard obediently walked to his parent's bedroom, opened his mother's closet and got the 'special' box from the top shelf. He picked out the purple lingerie set. He put the box back in its spot and returned to the bathroom. He placed the purple lace bra and matching g-string on the counter. Andrea leaned over and gave him another kiss, the lipstick that she had applied in the meantime left a slight mark on his forehead.

"Thank you, baby," she praised him, "you're a real gentleman."

Lennard silently nodded and blushed.

"Okay, now give me some privacy so I can change into those," Andrea said, "Can you do me a huge favor and pick out some dresses for me, baby? It would really save me some time. Oh, and some heels too. The extra-tall ones."

"Okay, Mom," he quietly replied and left the bathroom again.

Lennard got a pile of dresses and a few pairs of high heels from the back of the closet. He took them to the living room and sat on the couch. He turned on the TV and started flipping through the channels, not really paying attention to what was happening on screen.

"Oh, you're such a good helper," Andrea said a few minutes later, walking in wearing the purple lingerie set he had brought her earlier, "So sweet."

Lennard immediately turned off the TV, turned around and blushed. He couldn't help but stare at his mother's body for a few moments, before looking down to the floor in embarrassment.

"Do I look pretty?" Andrea asked with a cheeky smirk on her face as she noticed her son's reaction. He looked back up at her right away. She gave him a little twirl, "How do I look in these, honey?"

"G... Good, Mom," he stammered.

"Good," she said, "now let's see what you picked out for me here."

She went through the pile of dresses. All of them where recent additions to her wardrobe. Andrea had never worn such skimpy and revealing outfits before. She quickly reduced her choice to two dresses: A red strapless dress that barely covered her ass and a blue halter dress that showed off her breasts.

"Baby, which one should I wear?" Andrea asked and held them against her body one after another, "Did he say anything?"

"No..." Lennard sighed.

"I see. Why don't you pick one then?" Andrea smiled at her son.

"I... I don't know, Mom," he stammered, not sure how to decide or what to say, "I... I don't know what Jake likes."

"Oh, Lenny..." Andrea frowned, then smiled again and said, "Well, you know what? Too bad for him, because my baby boy gets to decide today! That'll show him who's the most important to me, won't it? Now come on, sweetie, pick one. Which do YOU like better?"

Lennard stared at the dresses for a few moments, and then he chose the blue halter dress.

"That's my boy," Andrea smiled, "Thank you, baby! I'm just so unsure what young men are into these days, you know?"

She put the red dress back in the pile and put on her son's pick, somewhat covering up her body, but still clearly showing her purple bra through the large cleavage, not to mention most of her legs being still exposed. Lenny blushed a bit more.

"Great choice, baby," Andrea cheered, looking into the mirror and adjusting her fabric around her breasts, "Now come here and help me with these shoes."

Lennard stood up and helped his mother step into a pair of tall, black high heels with cute leather straps around the ankles. He was used to this by now. He got down on his knees and adjusted the straps. He couldn't help but glance at her pedicured, painted toes. Another recent change to her appearance.

"Perfect," Andrea said, giving him a kiss on the cheek, as he got up, "Thank you for being so helpful and understanding, Lenny. You are being so good about this, sweetie. I'm so proud of you, and I love you more than anything."

"I love you too, Mom..." Lennard replied. He hesitated but couldn't help but try one last time, "Mom... D-Do you really have to go? Can't you just stay here... Just this one time... P-Please...?"

"Wha-... Lenny..." Andrea's smile faded and was replaced by a look of disappointment. She paused and looked at her son, who was staring at her in anxious anticipation, then she sighed and shook her head, "Lenny, I can't. We talked about this. You know, I can't. I just told you, you are being so good, honey. Please don't make a fuss now."

"Okay..." Lennard muttered.

"Okay. Thank you, baby," Andrea's smile returned, "Hey, remember it's the last time. We are so close. Don't worry, everything will be fine, honey. You can watch TV while I'm gone. Just make sure to keep your phone close by. Jake..." she paused, then continued, "Jake might want me to call you again."

Lennard silently nodded.

"I'll be back in no time, sweetheart," Andrea said, kissing him once more, this time on the cheek, "I love you."

"Love you too, Mom," Lennard replied.

The somewhat wholesome moment was interrupted by some loud banging against the door. Both Andrea and Lenny jumped in surprise.

"Come on, what's taking you so long?!" Jake yelled from outside.

Andrea opened the door, "Sorry, babe," she apologized, "I was just finishing up."

Lennard felt kind of relieved that the door was blocking his view to Jake. He didn't want to look at him right now. Or maybe, more importantly, he didn't want to be seen by him right now.

"Is the little dweeb holding you up again?" Jake asked.

"Not this time," Andrea said, "He was just helping me pick out my outfit. You like it?"

"Yeah, I do," Jake said, sounding sincere, "Very nice."

"Oh, I'm glad," Andrea said and giggled. She then turned around and gave Lennard a wink and cute little smile, "Okay, see you later, sweetie. And remember, keep your phone around!"

"Yeah, I swear to God, if you don't pick up, I will come back and break your nose! " Jake yelled from behind the door. Lennard winced.

"He will pick up, babe, don't worry," Andrea said, "I made sure. Right, Lenny?" she didn't turn around this time.

"Y-Yeah, Mom..." Lennard answered, almost whispering.

"That's right, " Jake snickered, "do as your sexy Mommy says, you little faggot."

"Hey," Andrea protested playfully, "don't call him that to his face, babe!"

"Well technically, I'm not saying it to his face," Jake joked, referring to the door between him and her son, "Whatever. Let's go, you slutty MILF."

Andrea giggled and stepped outside.

"See you later, sweetie," she said, again without bothering to turn around, and closed the door behind her. Lennard sat on the couch in silence.

"You got him really good this time," he heard his mother casually say behind the closed door.

"Yup, had to make sure the little faggot remembers it forever, right?" Jake proudly proclaimed, to which Andrea gasped and giggled, as their voices faded away.

Lennard felt the tears welling up in his eyes. He ran to the window and watched them walk up to Jake's car in the driveway. He could hear the faint sound of his mother's heels clicking on the pavement. Jake walked next to her with his strong arm around her waste. As they got closer to the car he reached down and firmly grabbed Andrea's ass. He opened the door for her and gave her a hard, rough smack on the ass as she got into the car. Lennard winced and was reminded that it was the same powerful big hand that had bruised his face earlier. He could hear the smack almost as loud as the clacking of the heels a few moments ago. He saw his mother smile as she sat down in her seat and pulled the door close.

He felt a tear trickling down his cheek and was about to turn away from the window when his eyes met with Jake's. His bully was looking at him from the driver's seat with his obnoxious signature grin on his face. He raised his middle finger, then leaned over to Andrea and pointed to the kitchen window.

Andrea looked over and gave her son a weak little smile. He couldn't help but think that she looked like a prostitute in her john's car. Jake kept talking to her, leaning over from the driver's seat. Andrea's smile faded and Jake started kissing her neck and fondling her tits. It was devastating. But it was what happened next that truly made Lennard's heart sink.

His mother slowly raised her hand and gave him the middle finger -her, upon his bully's request, french-manicured middle finger- while Jake kept kissing and groping her dolled-up body. She kept her middle finger raised at Lennard and held eye contact for a few seconds before turning to the side and making out with Jake. Her middle finger remained up. After they pulled apart, she turned back to the kitchen window, still flipping her son off, and silently mouthed the words 'I'm sorry' and 'I love you' to him, as Jake grinningly started the engine and pulled out of the driveway.

Lennard went back to couch and buried his face in his hands. He cried for a while, not knowing what else to do. When he finally stopped crying, he poured himself a glass of juice and watched TV. Of course, he couldn't concentrate on anything shown on the screen. His eyes kept moving back to his phone on the sofa table. Finally, it rang. As feared but expected, the caller was 'Mom'.

"H-... Hello?" he answered nervously.

"H-Hi, sweetie," Andrea said. She was breathing heavily, "how... how are you... doing?"

"Uh... I'm okay, mom," he answered.

"O-Okay, that's g-good..." she said, now slightly moaning, "I'm... I'm so sorry, baby. I'm so s-sorry..."

"It... It's okay, Mom," he said, "I know it's his idea."

"Y-Yes, it is..." she said. Her voice was getting higher and louder, "He's... he's making me... do all sorts of things."

"That's right, bitch!" Jake yelled in the background, followed by loud slapping noises and his mother crying into the phone.

"I'm... I'm sorry, baby," Andrea repeated, "You... You are so brave."

"It's okay, Mom." Lennard said, trying to reassure her. He felt his tears welling up again.

"He... He wants to talk to you, h-honey."

"Wha... What?" he asked, taken aback.

"Jake... He wants to t-talk to you, baby," Andrea said, and without waiting for her son's reaction, handed the phone over to his bully.

"What up, faggot? Heard you cried a like little pussy earlier!" Jake said, slightly out of breath. Lennard could picture his grin right away, "Damn, your Mommy's pussy is tight as fuck! No wonder you're such a skinny little twig."

Lennard hung his head. He could hear his mother moaning louder in the background.

"You're such a pathetic little bitch, you know that?" Jake continued, "Watching us from the kitchen like a fucking pervert. Bet you got hard when your Slut-Mommy flipped you off, huh?"

Lennard closed his eyes. He didn't want to hear any more. His mother's moaning turned into screaming in the background, "Ohhh! Oh my God, oh my God, yes, yes, yessss!"

Lennard couldn't help but imagine his mother being fucked by Jake. She had most likely taken off the blue dress he had picked out for her. Was she still wearing the purple lingerie? Or maybe just the stripper heels?

"You hear that, bitch?!" Jake asked, audibly out of breath now, "Your Mommy loves riding my cock. She loves it! Isn't that right, Slut-Mommy?"

Andrea kept moaning and screaming. Then there was another loud slap. "Answer me, bitch! You love riding my cock, don't you? Tell your pathetic son!"

"Ohhhh! Y-Yes, I l-love it! Yes!" she screamed, "Yes, yes, yessss! Oh my G-G-God!"

"Good whore," Jake said, "now tell the faggot what you told me before."

"I... I... I... I'm... I'm... I'm gonna cum!" Andrea moaned, her voice cracking.

"That's," another smack, "not," another smack, "it!" another smack.

"Ohhhhhhh!" she howled.

Then, suddenly it became quiet. Only now did Lennard notice that there had been a constant rhythmic squeaking of a bed that had abruptly slowed down and stopped. All he could hear was heavy breathing and quiet moans of his mother.

"Tell your pathetic son what you told me before or I'm pulling out right now."

"N-no!" Andrea pleaded, "Please!"

"Then tell him what you told me earlier."

"P-Please... I... I... I'm about to cum, Jake! Please! Pleaaase, babe!"

"Then tell him."

The phone was handed to Andrea. Lennard could hear her heaving breathing up-close through the phone again. It quickly turned to moaning as the rhythmic squeaking noises got louder. Lennard's heart was pounding in his chest.

"L-Lenny... You... Ohhh... You are a... loser.. A p-pathetic loser..." his mother said as the squeaking sped up.

"That's right, bitch, tell him!" Jake yelled in the background.

"You... You are a pathetic little... loser, Lenny! And... And Jake... and I... W-we think y-you... you will stay a v-virgin forever... "

"A virgin loser through college!" Jake howled, "Nothing's gonna change for him in college, isn't that right? He's gonna stay a pathetic virgin loser forever, huh?!"

"Y-Yes... A p-pathetic virgin loser... Through college... A-and forever" Andrea grunted in between moans, "N-nothing's going to... change for y-you in college, Lenny... You... will stay a... virgin loser... f-forever."

"Fuck yes! No girl would ever want to fuck that faggot, right bitch?"

"Yes!"

"And why is that, huh?!"

"N-no... Ohhh... Oh my God!" Andrea screamed, followed by another loud smack. The loudest one yet.

"Tell him, Mommy! Why does your faggot son deserve to be a virgin loser forever?"

"B-Because..." she panted, "b-because he has a little boy's dick... Because... I gave birth to a... t-tiny dick loser! That's why he deserves to be a a virgin forev-... Ohhh! Oh my G-God... Oh my God! I'm cumming! Ohh my G-"

She hung up. Lennard sat there on the couch, trembling and sobbing. He felt nauseous. He buried his bruised face in his hands and bawled uncontrollably. He felt so ashamed and humiliated. He cried and cried. He didn't know how long he stayed there like that but eventually heard the front door open and close. He heard the clacking of her heels as she approached. Then he felt his mother hug him from behind.

"I'm sorry, baby," she said, her voice was trembling, "I'm... I'm so sorry."

He didn't answer.

"I'm so, so sorry, honey," she cried. He felt her body quiver as she sobbed and tightened her hug. She held him and repeated the words over and over, "I'm sorry... I'm so... sorry! I'm sorry!"

"I know," he eventually said, "I know... You were just... trying to make Jake... happy..."

"I'm sorry," his mom went on, she repeated it over and over. He felt her warm body quiver and press up against him as she held him. He looked down at her manicured, motherly hands locking her arms around him, "I'm sorry, Lenny, I'm sorry.... I'm so sorry."

Finally, Lennard turn his head to tell her that it was okay. That she could stop apologizing. That he understood. And that's when he froze. He froze at the sight of Jake standing behind his mother. Towering over the two of them. Andrea's grip tightened. Lennard's eyes wandered down to Jake's exposed crotch. He was jerking off and looking straight at him with a sinister grin. Lennard didn't know what shocked him more, the fact that his bully was standing in his living room, the fact that he was masturbating right there in front of him, or the massive size of his cock. The thing looked like a baseball bat.

"Jake," Andrea said quietly, "make it quick, babe."

"You got it, slut," he replied, then lifted her blue dress up, placed his hands on her hips and stuck his cock inside of her. He grunted. She moaned. Right into Lennard's ear. And then Lennard felt his mother bump into his back and the couch from behind. She tightly held onto him, her arms wrapped around his scrawny torso. Bump. Bump. Bump.

"I'm sorry, Lenny," she whispered into his ear, "It will be over soon."

Jake picked up the pace and the bumps became more frequent and intense. Bump! Bump! Bump! Bump! Meanwhile Andrea's breathing became heavier and her moans got loader, "I'm sorry, baby... I... I love you, sweetie... I love you... Ohhh... Please forgive me..."

Lennard was speechless. He felt paralyzed. Even if his mother would let go of him, he wasn't sure if he could move. His mind went blank and his body was frozen. He just sat there feeling his school bully fuck his mother against his back, listening to her breathing, grunting and moaning into his ear, with her head placed on his shoulder and her arms tightly locking him. Bump! Bump! Bump! Bump! Bump!