My life at 16 pretty much sucked. I know alot of people say, "well that's a hard time for anyone." But mine just seemed to be a little bit tougher. In high school I was basically average. Grades, looks, everything, just average. I had a couple of friends that I hung around with and that was it. I lived with just my mom, being that my dad left us around 10 years ago, and most memories I have of him are very vauge. My mom however seemed to be anything but average. She was 36, but she took care of herself by eating right and working out, and had shaved a few years off her age because of that. She wasn't super hot or anything like that, but lets say she would have no problem hooking with almost anyone she wanted to at a club or bar. She had decent sized breasts and an overall good body. I had never actually thought of her in an overly sexual way, but I of course wasn't blind to her assets either.



Anyways, we used to struggle financially, as my mom, her name being Catherine, and mine Adam, worked as a secretary at a crappy law firm. A few years ago she was able to get some financial aid and started taking classes as a paralegal, and because of how well she did in those classes, got hired at a very well to do law firm. She apparently was very good at her job that within two years she was making three times what the average paralegal makes, which doesn't suprise me, given her very take charge and demanding attitude and personality. No, we weren't super comfortable or anything, but we were able to breathe alot easier when it came to money.



Mom spent alot of time working, so we never really got all that close. I would come home from school and do some homework and jerk off to porn on the internet, and she would usually get home around 6 p.m. and make dinner. We ate dinner together at the table and that was the only time we ever spent together or talked. I would do dishes and Mom would retreat to her room and I would do the same. It was quite boring and dull and I just wished something exciting could happen in my life just once. Looking back, I should have cherished the boring life.



One particular Friday my mom came home in a real pissy mood. She hadn't missed a day of work as long as I can remember, but her firm required all employees take at least a one week vacation once every two years. She decided to get it out of the way and take the next week off and use it to catch up on sleep and just relax. It didn't bother me until monday when I got home from school. I went into my room to start my homework, and a few minutes later came a knock on the door. I told mom to come in and she did and sat on the bed while I studied at my desk. It was obvious she was bored out of her mind. We made small talk till about 6, and then she went to make dinner. While we were eating, I noticed she was drinking wine with dinner. I had never once seen her drink any form of alcohol, so after she polished off 4 glasses, it was apparent she was quite a bit tipsy.



"Honey, after you finish up the dishes, why don't you get a yourself a shower then meet me in the living room for a movie." my mom said.



This kinda threw me off, mainly because we had never done anything together, but I figured she hadn't got any human interaction today so she just needed some company. Mom said she was going to get a shower as well and get more comfortable. She grabbed the bottle of wine and went into her bedroom as I got ready to get into the shower. I wasn't able to jerk off earlier being that mom was here, so I was a little horny and decided to give myself some relief. I guess I was really getting into it, because the next thing I heard was mom saying "looks like you're enjoying yourself." My shower curtain is white and she was able to see my silhoutte beating off.





"Crap! Mom! what are you doing in here?" I yelled.



"Relax baby, I was out of toilet paper and was just getting some from in here. You have nothing to be ashamed about, everybody masturbates." she said laughingly. I could see through the curtain she still had the bottle of wine in her hand. I definetly had one thing to be ashamed about though. The tiny little member between my legs that couldn't even break 3 inches when hard. My mom startled rambling on about our bodies and stuff and I was becoming a little uncomfortable. "You shouldn't be ashamed of your body dear, as a matter of fact, let your mommy see your grown up body." And with that she pulled backed the shower curtain revealing my body and my little dick that had gotten soft while she had been in the bathroom. And thats when an embarrasment rushed over my mind and body like nothing else had before.



"Hahahaha, wow son, you inherited your dads genes alright, that thing is puny." she laughed. I tried to cover it up, but she slapped my hands away. "I guess I was wrong, maybe you should be embarrased. How big does it get hard?" she asked. I didn't answer, I just hung my head down humiliated beyond belief. Thats when everything I knew started crashing down. All of a sudden I felt a hard slap against my cheeck and I fell over in the shower. "I asked you a question, you pathetic piece of shit, HOW BIG DOES IT GET HARD?!"



I quietly said, "about 3 inches" as I laid on the shower floor, completly shocked by what was going on.



Again my mom started laughing at me. "Wow that is pathetic. Get your ass cleaned up and dried off and come into the living room, and don't bother wearing anything."



And with that she left with me still lying on the shower floor. I felt like crying, but I was honestly in a state of confusion that just left me wondering what the hell was going on. I got out of the shower and dried off. I walked into the living room and my jaw dropped. My mom was wearing one of the sexiest nighties I had ever seen. It was red with black trim and did little to cover up her most precious parts.



"Sit" she said sternly to me. She moved towards me on the sofa and started stroking my cheek. "I'm sorry for hitting you earlier honey. But you need to learn how to obey mommy, understand."



"Y-yes Ma-a'm" I stuttered. I started to think that maybe all this was just the alcohol, and this would be a one time thing. I soon realized that may not be the case.



"You want to know why your dad left us honey." I didn't answer, just looked down to the ground. Then I felt a sting against my face, didn't really hurt, but it caught me off guard. "Honey, I asked you a question, and when mommy asks you a question, you damn well better answer, or next time you will know what pain feels like." she stated calmly, while drinking more of her wine, now on her second bottle.



"Yes" I mumbled



"Yes what, dear."



"Yes, Ma'am"



"Lets drop the Ma'am shit. Anytime I ask you something you will respond with "Yes, Mommy" understood."



"Yes Mommy." I said extremly embarrased.



"Much better. Well to put it simply, your dad left cus he's a pussy. He couldn't take what I had to dish out at him. He thought he could, but it turns out he was just a little sorry piece of shit not worthy of my time. He was a pathetic slave"



"A slave?" I asked



"Yes honey, he was my slave. And not a very good one at that. He simply refused to do some of my fantasies. And when I forced him to, he left. Those were some good times though, taking your fathers paycheck and spending it on myself, having him eat my cunt 3 times a day at least, getting fucked by really hung studs while he watched. It was wonderful. But then he left us, and now I've had to spend so much time working and supporting us, I haven't even been licked or fucked since he left. Your dad always begged to fuck me, but I only left him once, and thats when you were conceived. I actually always wondered if you were really his, considering I fucked about 10 different men around the same time, but looking at that pathetic little dick, it's obvious you are your fathers son. But maybe you're bigger when you're hard, why don't you get it hard for mommy." she said as she grabbed my little dick and shook it. That was the first time ever anyone had touched my penis, and it felt great. Even with as embarrasing as all this was, my dick sprang to life getting hard.



"HAHAHAHHA, oh my god I can't believe it, that's all you got son, wow you are even punier than your father. Wait, stay right there." I wanted to get angry, but I just felt so ashamed, just sitting in front my mother naked with what I was starting to think had to be the smallest penis on earth. My mom came back with some measuring tape and measured me. "Wow, I can't believe it, 2 and 3/4 inches. Son, I hate to break it to ya, but you are never gonna give a woman an orgasm with that thing, chances are no woman will even let you fuck her with that tiny thing"



And with that, I started to cry. That is, until mom slapped me again and screamed "stop your bitching you sissy piece of shit or I will give you a real reason to cry. Now son, I've been without any sexual satisfaction in a long time. My vibrator can only do so much. Now follow me to my bedroom."



I did as she said and followed her as she stumbled, drunk, to her bedroom. I was again shocked to see on her bedposts were handcuffs and a dildo. I wasn't exactly sure what each were for, but I was soon to find out.



"Lay down on your back slave." when I heard mom call me slave, I knew exactly what she was intending to do. I was praying that it was just her drunkeness, and this would all be over soon. At least a part of me thought that. Another part of me was kinda excited. This was my first time doing anything sexual with another human being, and I was really turned on.



My mom cuffed me to the bedposts, both my hands and feet. Their was no escaping whatsoever.



"Lift your ass up as high as you can." I did as I was told, then I started to freak as felt something starting to penetrate my virgin asshole. I soon realized that the dildo I saw was for me. I soon lost all excitement and for the first I really got scared. "No mom, please, I want to stop, stop this mom" I begged. My mom stopped and looked at me. She leaned over and grabbed my chin and said, "Boy I am going to toughen you up, you're gonna be a tough sissy slut, not a weakling like your father. Plus your tiny hard on tells me that you are enjoying this, so why not continue." It was true, no matter how much I tried to get it to go down, I was hard as a rock. My mom slapped me 3 more times till I agreed to put my ass up again so she could slide the 8 inch dildo into my ass. I clenched my teeth and balled my fists as it was one of the most painful things I had ever experiecned. Once it was in there, although still uncomfortable, the pain mostly subsided.



"How you feeling baby" mom asked. Knowing already not to upset her right now, I just answered "Good Mommy."



"Thats a good little slut. Now, lets have some real fun." And with that comment she climbed on top of me, her ass on my face, her cunt on my mouth. "Now eat me you little bitch, make Mommy cum like she's never cum before." I wasn't sure what to do, I had never done anything like this, and had only seen a few pornos with pussy licking before. I started to lick her like a dog licks a person, but apparently that wasn't good enough, as she bent over and hammerfisted my balls. I scremed out in pain, muffled by her crotch.



"Oh yes baby, thats so much better, scream into Mommy's pussy." After the pain subsided, I tried a different approach, and felt around with my tounge for her clit, and gave that all my attention. Apparently that's what she like as she started to buck her hips on my face. Soon I started having trouble breathing and I thought I was going to pass out, but then all of a sudden a gooey liquid was sprayed into my mouth, and my mom got up to look me over. I started coughing spitting out her cum and few of her pubic hairs that had gotten into my mouth. That was the wrong choice, as she immeaditly took her foot and slammed it into my balls.



"Don't you ever disrespect me by spitting out my cum. That should be gold to you. Now lick up what you coughed up you little bitch." She unlocked the cuffs and I thought I was going to cry again, but I was able to hold it in as I licked up my mom's cum and pubes off the floor. After I finished, she grabbed me by the chin and said "Good sissy bitch. Now, go get into the bathtub. I was thinking that now that mommy had cum, this would be the end of it. And again I was wrong. She brought the cuffs with her and demanded I lay down in the tub. She then cuffed both my hands to the hot water handle and put the tub stopper in. "You've done such a good job, my sissy slave son, and now you get to be rewarded. I was hoping that meant I was going to be able to cum, but the biggest shock of the night came when she lifted up her nightie, exposing her pussy to me again, and let out a warm stream of piss right onto my face. I tried to move my face, but she reached down and slapped me and said "Hold still you piece of shit and enjoy this." As much as I hated this, I kept my head still, as my mommy's piss covered my face, eyes, and mouth and trickled down my body. She finished, looked at me and said "Good boy." She then turned around, walked out, turned off the bathroom light, and closed the door, leaving me in a pool of my mommy's piss. I finally started crying, wondering what tommorrow was going to bring