Caught & Taught

All characters and places are fictional. Anyone engaging in sexual activity is 18+.

-----

"Oh...fuck" was all I could muster. I had been playing a game of tennis on the WEEE4 Console; it uses motion joysticks to control the game. I forgot wear the safety bracelet that is there so such things don't happen. Now the TV in the family room is broken and I'm in DEEP shit with my mom. "I might as well pack my things now" I thought as she's going to so furious with me.

My name is Steven and at 18, I live with my single 40 year old mom; Linda and younger 14 year old sister; Allie, in a decent town house. I go to community college where I'm just getting my basic credits in until I can transfer to a university and study Exercise Physiology to become a physical therapist. Clearly though I'm not so bright.

I was merely playing a couple rounds before I go into work at the grocery store as a cashier and I have to deal my hard ass boss and dick weed front-end manager. There was an overlap in mom and mine's schedule where she'd be back home from working her full time job at the bridal store and I'd be home before going in. I could of just left and written a note but that's not fair to mom or Allie. So I stayed and kept pacing until mom came home. Allie was across the street at her friends house that Saturday.

Mom is a take no shit momma bear. At 6 foot with black hair, bangs, a large 38 DD chest slim waist and round butt she was also what my best friend blatantly described as a "MILF" and a "PAWG." Dad had died 7 years ago from throat cancer. Thanks to his chain smoking habit. She never dated again as she remains devout thanks to her religion.

She teaches fitness part-time at the local expensive fitness club. Which, has its perks because it means we get free admission to the gym, courts, and pools both indoor and outdoor. I just hang out at the indoor pool sometimes while Allie does yoga class. I should try to work out but no matter what I do it feels like I'm still a short little scarecrow. But, I'm so tired from work and school, that sometimes I just need to chill in the jacuzzi....and I won't lie and say there aren't beautiful women there either. Not that I'd have the nerve to ask a girl out. None the less...

Mom came home and she asked me what was wrong as she could tell I looked guilty.

"Mom, it was an accident I swear. It slipped out of my hand."

She looked at the TV and and then back at me.

"Jesus Christ Steven! I can't believe you broke the television! Do you know how fucking expensive that was!? Huh!?"

When mom cursed or took the lord's name in vain, it was serious as she was a devout Christian.

"Were you drinking Steven? Let me smell your breath...Now Steven"

I shrugged and came closer. My chest pressed against her large chest that was covered in a white polo. I breathed out and she shook her head.

"Well you're not drunk, but how could you be SO STUPID!? I can't afford to buy a new one so we're all just going to have use our phones and tablets for a couple of months."

"I just forgot to put the strap on my wrist and it happened so fast. I'll make it up to you and Allie. I'll pick up more hours at the grocery store."

"And what let your grades slip? No, no you will not. But a new TV will have to be your Christmas present and birthday present...Unbelievable."

Mom shook her head and headed upstairs to her bedroom. I got ready for work. I shouted "Love you" as I left but I didn't hear it back.

----

I drove to work in my crummy old station wagon. I was angry, angry at myself for being so stupid and moronic. Now how am I going to play video games? Especially the newest first person shooter that comes out in December. My birthday is December 4th and I was hoping to get a pre-order of it for my birthday. I heard the early reviews are raving about it. 5/5 stars, 9/10! Then I had to ruin it by being so stupid and careless.

While at work my mood was a bit low, ringing up customers. Usually I'm very chipper and talkative, but that day I was distant and quiet. I managed to get through my guests. I wasn't being a dick to them, I was just quiet. No one complained about me or seemed to mind as long as I didn't fuck up.

Kyle came over and asked "Hey Stevie, your dog die or something? Why you so blue, hmm?" He said mocking me.

"I'm fine Kyle. No one died. I just accidentally broke something valuable."

"Ooh do tell." He demanded rubbing his hands.

"I accidentally broke my family's tv while playing a game of virtual tennis."

"Oh no way! Hahaha, did your fine ass mom kick you out? Because I'll take your room."

"Ew Kyle! No, she didn't but it's gonna be my birthday and Christmas present to get a new one. We don't have the money to get a new one right now. It won't be until Christmas maybe."

"Hahaha you're such a giant dumbass man! Good luck dude!"

I could see Kyle then go tell the older customer service worker, Becky who was 27 and she just started laughing. I was beat red in embarrassment. Becky wasn't bad looking but I suspect those two were secretly fucking despite her boyfriend being the produce manager. I wonder if Mr.Robins knows or even cares...Grumpy bastard.

----

The next day I had a full 8 hour shift and I was joined on register duties with Jenna who was a year older than me. I had a big crush on her.

Jenna is 5'8 long blonde hair with thick glasses and and great smile. She doesn't have large breasts but she makes up for it in the ass department. I wish I could smack that ass every time I walk past and grip it. She's very nice to me and she's single but I haven't the nerve to ask her out.

Like me, Jenna goes to community college but I don't think she has plans to transfer. Something about a bachelors degree in business management. I don't know. It's hard to concentrate when we talk because I'm usually just high on get to talk to her and I get lost in those baby blue eyes.

The only thing I don't like about her is that she smokes. So when I had my lunch break I took my McBurger meal out the picnic table outside the store. This is where a lot of the other workers come to smoke too. Jenna came out because she was training a new guy and they wanted him to try going alone for half an hour.

"I heard about your little accident Steve."

"I'm sure the whole store does now."

She laughed and then coughed. "Yeah. But it was an accident. I've seen my nephew almost do it before."

"So do you know if Mr. Robins is giving out more hours? Or raises anytime soon. I could really use the money. ASAP."

"Why don't you skim some?"

"You mean steal?"

"Yes and keep your voice down...Look we're allowed to be at most $10 short every day without getting fired or written up. So just do what I do and skim a $10 every time your on register and watch it add up. As long as your not over by that much they don't care, they need us. They won't fire us."

"I don't know if I--"

She sat down on my lap. I could feel her big ass on my dick and I started to grow hard. She wiggled a little and looked back and simply said "Don't be a pussy" with emphasis and a sultry inflection on "pussy."

----

My first time skimming money out of the till was exhilarating. It was stealing, pure and simple. But I really needed the money for a new TV.

I would do it while giving change and pretend to drop a $10 bill or just palm it if I was quick. It lost it's edge real quick though and I soon realized I'd be short of my goal to get the TV before Christmas.

So another break came when me and Jenna were able to talk again out on the picnic table.

"Jenna I'm in a bind, I'm not gonna make it to $600. I'm going to have to skim more money."

"I wouldn't do more than $20 or your pushing your luck hun."

She sat down on my lap again and wiggled once more. "Let me tell you though I think what your doing is really hot and I like to see you got some balls." She reached down and grabbed ahold of my junk, not hard but firm and slid her palm across my dick.

She flicked her cigarette away and got up. Thank god I had 15 minutes to think about baseball and get my erection down.

----

By now I'd been skimming $30 worth of cash from my drawer every shift and I was getting confident. Those numb skulls must not being doing their jobs if I haven't gotten caught yet. So really am I to blame for their ignorance?

I got so confident that I even asked if Jenna would want to come hang out with me in the indoor pool at the fitness club. To my amazement she said "Yes."

We met in the parking lot on the late November evening and we were wearing our sweats. She was wearing her former high school's and I was just wearing some plain ones and a band t-shirt which she took notice of.

We put our stuff down on a small table in between two lounge chairs and stripped. Her breasts were bigger than I thought, definitely a large B cup under her triangular blue bikini. The next party is what I was waiting on. While her bikini bottom wasn't a thong her ass was so big her cheeks didn't quite fit in it. Thankfully.

She dove in the deep end and I soon did a cannon ball with best Ron Bergundy impression, something that made her giggle. I wish I could of recorded that little laugh, it was so damn cute. We raced each other for a while. My lanky arms actually helping me for a chance. She won a round or two as well. She went outside to take a quick smoke break and I decided to jump in the jacuzzi. There was an an old married couple in their 60's on the other side of me. I smiled and introduced myself. Their names were Mark and Karen.

When Jenna came in she joined me. She sat by on my lap and simply leaned her head on my shoulder, closing her eyes. Mark and Karen got up and left, smiling. Jenna then brought my hands down to her bikini bottoms and slipped my hands under them. I was touching my first pussy. She had a small patch of hair and I felt the sleek folds of her vagina. She groaned in my ear. I saw someone staring at us and quickly pulled my hands out. She got out and took another smoke. While was smoking I worked hard again on losing my erection.

She came back in a sexy walk and whispered in my ear "stay here for 15 minutes while I'm in the locker room, I've a gift for you hun."

Waiting I my thoughts were racing. She came back out in her sweats and told me to open. my hand. She placed her bikini bottom in it and gave me a deep kiss. I was in heaven watching her ass sway as she walked to her car.

----

It was another day where mom and I had an hour crossover at the house. I was about to leave and she was coming home but there was an hour between.

"So rumor has it you've got a girlfriend." Mom said inquisitively with a grin.

"I don't know." I replied with a smile.

"What's her name?"

"Jenna, she's a year older than me and she's a cashier at the grocery store."

"I see...Word going round is things got heated in the jacuzzi with you two." Mom was smiling ear to ear.

"I'm sorry it's just that--"

"Hush! I understand, you're young and in love. While I was a bit embarrassed at first, you deserve to have your fun. Let's say your father and I weren't exactly innocent."

"Ew! Mom!!!" Allie shouted as she got something from the refrigerator.

"Hey this is a private conversation." Said mom.

Allie went back to her room.

"Do me a favor and whatever you do, be safe. You know what I mean. It's like putting the wrist strap on your game controller. Except...you know, sex. Haha."

I put my face in my palm as the embarrassment washed over.

----

The afternoon shift at work was pretty weird. As soon as I walked in my coworkers were giving me strange looks. Was it because of what happened with Jenna?

Jenna was there and avoided eye contact with me. I grabbed my cash drawer and opened my register. A note read "Over $5 and you're fired."

I was nervous as could be the whole shift. I was practically shaking and did my best to give back correct change. Luckily most of my guests paid with credit and debit.

It was nearing the end of my shift and we were closing when I looked out the window and thought I saw my mother's car. It was a sedan with a unique floral steering wheel cover and seat covers. Maybe I was overthinking things.

"Hey shit bag, Mr. Robbins wants you in his office." Said Kyle behind me, pushing me to Mr. Robbins office in the back upstairs.

There was a cold pit in my stomach and my heart was racing. This is it. This is it.

Kyle opened the door Mr. Robbins office and I saw Jenna sitting down along with my mom.

"Sit down Steven." Said Mr. Robbins.

Kyle locked the door behind us and stood guarding it.

"Do you know why you're here young man?" He said with a very stern look on his face.

"Me and Jenna kissed?" I said shrugging my shoulders.

"Hahaha. No, no." Mr. Robbins said as Kyle joined in the laughter.

"The money. You've been skimming it and we caught it on camera. You slipped up two nights ago and let me show you."

He turned his computer screen around to face us. It showed a black and white image of my register and me pretending to drop a $20 only to pocket it after the guest walked by. Shit...

My mom turned to look at me with wide eyes and mouth agape.

"I can expl--"

He raised his finger to silent me.

"You will speak when I want you to."

Kyle slapped the back of my head.

"Kyle's also been keeping track of your register after you told him of the TV incident. Do you think we're stupid Steven?"

I hung my head.

"I said 'Do you think we're FUCKING STUPID Steven!!!" Pounding his fists on his desk.

"When I discovered Stevie here was skimming I began watching Jenna and lo n' behold who's been skimming too. Granted Jenna it's nothing compared to Shitbag here but I'm guessing you taught him didn't you?"

Mr. Robbins looked at Jenna and she said "Yes sir."

"So seeing how you two have been stealing from us it's time for punishment."

"I know I'm fired sir. We'll leave." Jenna said.

"Oh no you're not just fired. I said you're being punished!" Mr. Robbins shouted.

Mr. Robbins came from around his desk and grabbed my mother by her arm roughly. He brought her around his desk and bent her over. She screamed.

"Shut the fuck up bitch!" He said shoving her forward. She was wearing a long sleeve t-shirt and a long skirt. Her hair in a ponytail.

I tried to get up from my seat but Kyle held me down and produced a box cutter. He drew it to my throat.

"Mom!" I shouted.

Mr. Robbins pulled her skirt above her hips and slapped her big ass. He unbuckled his pants and slid his boxers down. He then took a pair of scissors and cut off her panties. He flung them to Kyle who took a big whiff and shoved them in my face. "Smell your mom Shitbag, hahaha."

It was a weird smell and it was similar to Jenna's wet bikini bottoms.

"Jenna come get on your knees. Now!!!" Mr. Robbins commanded.

Jenna got down and he shoved his cock in her open mouth. He began face fucking her while he was fingering my mom. My mom was staring at me crying.

I whispered "Sorry" to her.

She closed her eyes.

I heard "Gawk Gawk Gawk!" Mr. Robbins was getting deep throated by Jenna. I can't believe she knew how to do that. I was wondering how many guys she'd done that too.

After a while of throat fucking Jenna, he pulled out and aligned his large 8" cock with mom's pussy. He plunged deep into her.

"Ooooh fuck!" Mom shouted.

"She's tight, I no wonder you're so small."

Kyle laughed in my ear.

Suddenly mom's eyes went wide and her mouth made hung open.

"Awe yeah I'm at your cervix now! How does it feel bitch!?"

"Oh my Christ! Stop! Stop! You're too deeeeep!"

Mr. Robbins got the scissors and cut off her top. Her huge breasts now contained by her bra. He unclasped them and let her tits fly free.

Her nipples were nickel sized. He reached out to grab them from behind. Twisting her nipples and mauling her breasts.

"Jenna, there's duct tape in my drawer. Get it and give it to Kyle."

Kyle then tied both of my forearms to the armchair and wrapped my ankles up. I struggled to move. Fighting at every last turn to break free and save my mom.

"Pull his pants and boxers down Jenna, let's see this puny Shitbag's cock." Said Kyle.

She looked up at me with fear in her eyes.

My cock was now exposed, limp and flaccid.

"Look at your son's cock bitch! Look at how small he is. How small is he?" said Robbins.

"Small sir, very small. Oh god! Oh God."

He smacked her ass hard.

"Do you think he'd be able to please Jenna?"

"No. No fuck-fu-fucking way-ay!"

"Are you loving my cock bitch!" Is Steven's Mom enjoying my cock!?"

"Yes! Oh god yes!"

I could tell she wasn't lying. I know when she's not lying by now.

"Look at your son and tell him you love my cock."

"I love his cock Steven. I really fucking do!"

"Mom! What the fuck!?"

"Shut the fuck up Steven! Let me enjoy this! Oh god I haven't had good cock in sooo long! Just shut the fuck you little bitch."

That hurt. Yet for some reason I was getting hard being humiliated like this. What the fuck is wrong with me.

"He's getting hard guys!" Jenna shouted.

"Oh look at your little dick you sick pervert. You getting off on my naked body getting fucked for once?"

I didn't answer, my cock just grew to my full 5 inches.

Kyle now had his pants down and boxers below his knees. He was sporting a 7 inch cock but it was thicker than Mr. Robbin's. He told Jenna to suck on it and she obeyed. Soon though he had her bent over the desk in the opposite direction of mom with her ass and pussy on display towards me. It's the first time I'd seen a pussy up close.

"Oh you like that Shitbag? Here lick it, get her lubed up for me."

She backed up, bent over at the waist. I cautiously stung my tongue out as that same scent flooded my nose. It was literally nothing like I'd never tasted before. I loved it. Jenna started groaning. I nearly shot my load. But then Kyle took all that away by forcing her against the desk again. He stuck his dickhead in the same spot my tongue just was and went deeper in.

"Ow! Fuck you're too big Kyle! Pull out!"

He merely grabbed her wrist and pushed it behind her back in a wrist lock.

Meanwhile my mom was still being fucked by my boss. "I'm cumming sir! I'm cumming!"

"Yeah! How about I fill you up bitch? Give Steven a new baby brother."

"No pull out! Don't cum in me. I can't afford a baby! Don't cum in me! Pull out, please!"

My boss gave three hard thrusts and I could tell by the creampie porn I watch that he'd cum deep in her.

Meanwhile Kyle was getting deeper into Jenna. He hit bottom because I could see his penis fully disappear into her now and their crotches meet. He pulled back quickly and thrust sharply back into her.

"Oooowe!"

Kyle smacked her ass twice so hard he left a red mark.

He then began thrusting back in repeatedly so much so that the smack of jiggling ass slapping his pelvis echoed in my head. She began grunting and gritting her teeth based on the mirror behind Mr. Robbin's desk.

"Pass me the duct tape Kyle." Said Mr. Robbins as mom was trying get the cum out of her pussy with her fingers. He slammed my mom's head on the desk and taped her wrists behind her.

"Bitch I think you enjoyed that fucking too much. How about a different punishment. Steven do you want to fuck your mother?"

"What? No!!!"

"Well too bad." He said grinning. He brought mom over to me and had her sit on my lap. He reached out to grab my cock surprisingly and shoved it in her moist warm vagina.

I just lost...my virginity...to my mom...in front of my girlfriend, boss and manager!

I was angry and aroused by the sensation. I was trying to buck my mom off of me but that only made the matter worse. She was loose but warm and wet. I couldn't feel my bosses cum so he must of shot his load deep. "I'm sorry mom!"