I caught her fucking my principal when I was 16 when she came to pick me up for detention. He decided to tie her hands behind her back and cane her ass while I was still in the room. Then he gave me another week of detention after cumming in her ass. He would then give me regular detentions and then choke her with his cock while spitting on her face when she came to get me. She would also leave with a red ass and one hand print in the middle of her back. This was from the principle shoving his cock into her ass while holding her head up by her hair. Then, while in the middle of randomly smacking each ass cheek in irregular intervals, he would wind his arm back and then slap her back with enough force to knock the wind out of my mother. Invariably, she would scream in pain, burst into tears, have an epileptic orgasm, and make him cum in her ass all at the same time. The principal liked to then throw her head down onto the desk, slap her ass again, making her wince even more, and then go around and jam his cock into my mom's mouth till it was clean. Since my mother was an immigrant into this country, the principal would always like to shove the end of a flag into my mom's ass while fucking her cunt raw, shouting, "How do you like America, bitch?!"

My mother would reply back between moans, "oooh yes sir! I love it. AAAAAAHHH!" Usually she would come again from this humiliating treatment. Only then could we go home.

When I wa shy of 17, I found out she was fucking my school janitor while I was at wrestling practice after school hours. She would come two hours early and the janitor would take her to the boiler room. He would drag her by her hair close to the furnace and begin stripping her while biting her in random places. She would yelp in pain, screaming "OOWHH!" and "OOOOHH" each time. Once, while munching out my mother's pussy, my mother was moaning like a bitch and a whore. Since the school was empty at the time, due to practice being cancelled, only I heard her yelping repeatedly as she came, "OOH OOOH AAIEEH! AAAAHH!". Then, I watched as the janitor suddenly moved from lapping at her cunt to biting her inner thigh right next to her pussy lips. She screamed with pain and started to come, while also recoiling from the bite. But the janitor held fast with his jaw and started to gnaw on the side opposite the first bite. My mother whimpered and moaned like a cheap slut, "mmmhhh AAahhhh OOOOHH! YYYYYEAAAAAOOOOWWHHH! AAAHHHAAAHAAAOWWWHhhh!"

Finally the janitor let go and grabbed my mother by the back of her neck. With tears streaming down her face, she started to make out with the janitor, letting him invade her mouth with his disgusting tongue. He then turned her over and quickly aligned his malignant cock with her pussy, but decided to change to her ass. Before my mother could protest, he shoved his entire shaft into her tight asshole, making her shriek in pain. The janitor wrapped up her arms and her neck in order to subdue her and bit the side of her neck, causing more pain. Slowly, my mom started to fuck him back, enjoying the sensation in her ass. Then all of a sudden, the janitor grabbed both sides of her ass and started hammering her, drawing his cock all the way out, then thrusting it in with such ferocity, my mother screamed each time he buried his cock into her asshole. "AAAAAAH! You bastard! FUCK ME! OWWWWHH!! YEAAAAHH! HARDER! MAKE IT HUR-- YEEEEAAAAOOOOWWHH! UUHHH UHHHHH MAKE ME CUM WITH THAT ROD, BABY! OOOOOOHHH!"

As the janitor reamed my mom's ass he was slapping her ass, her back and also gnawing on her neck and shoulders. He then started to smoke while fucking her at a slower pace with my mom constantly moaning.

"I'm gonna leave my mark on you, you slut! You're nothing but my whore to use!"

"MMMhhm. Anything you want, baby! I'm all yours! Treat me like the slut I am." replied my mother.

"What if I wanted your son to watch?" queried the janitor

"Ooooohh yeaahh! Anything, darling! Make me your whore!" squealed my mom.

"Alright, but you asked for it!" With that, the janitor gripped her hair, exposing her neck and pinning her head down to the ground. He then switched from her ass and drove his dick into her hungry pussy. This made her scream with delight and she started to cum almost immediately. He then took his cigarette with his free hand, flicked the ash, and screwed the red hot end right into the center of the back of my mom's neck.

She was not ready for this and her eyes went wide, and then shut closed with pain! She let out a blood curling scream and burst into tears. Oddly enough, the janitor starting to fuck her pussy harder and harder, making her cum at the same time. Then, he pulled out and creamed into the fresh burn in the back of her neck, leaving her sobbing, sweaty, cumming, and moaning on the floor of the sweltering boiler room.

   I have never been attracted to her in anyway until that day. She was stuborn, political, a bit big around the love handles like i mentioned before. And she was toataly anti-sex offender. She hated child molester with a passion. 

   But when she returned form changing, she had changed her whole wardrobe. We were going into town with her later in the day, and it seemed she had changed for that ahead of time. She wore a demun mini skirt, that was clenching her bottom like a magnet. And a grey tank top, with no bra, for obvious reasons, That pushed her boobs up, and her nipples were poking on out. 

   I started at her as she ytped on the computer, her boobs bouncing lightly.

   The time came for us to head into town. We pilled into the truck and headed in. I watched her breats in the reive view mirror from the backseat. they were mezmorizing. While in the store, she broke off from me and my buddy, and said, "you guys can get ice cream or whatever, ill pay for it." so with that we began searching for a treat. But i needed to see his moms boobs again, so i told him i had to use the facillities (bathroom). he understood, and i ran off down the isles, searching for his mother. i finnaly found her in the womans section, looking t maxi pads, and tampons. The idea of her booty rubbing up against a maxi kinda made my dick hard. afraid she would see me, i backed off and went back to my friend.

-two hours later

   I had decided to spend the night at his house that night. Hoping to get a glimpse of his mom in her nighty, or maybe something better then that. We chilled out for about an hour, then his mom got up and went into the bathroom to brush her teeth. She was in their for about another hour, then i heard the door open, and shut, "goodnight guys, don't play games all night." We were playing halo like mother fuckers on crack. Funnest, game, ever by the way.

   So about 4 hours later, after a Halo 3 jam session, my friend decided to go to sleep. he settled into his bed, and i continued to watch TV, even after he was snoring.

   About 45 minutes later i had to poo. So i got up silently, turned the volume on the tube down, and walked silently to the bathroom. I opened the door, crept inside, shut the door behind me, turned on the lights, and i was good. I walked quickly over to the toilet, pulled my shorts down and sat.

   While on the potty, i examined my surroundings. i saw piles of my friends dirty clothes, and a small pile of his moms dirty clothes. On top of the pile was her mini skirt from before. I leaned over as far as i could, and grabbed it up. as i lifted it, a pair of blue and white panties fell out. they were big, but very sexy. I lifted them to my nose, and gave then a little whiff for fun, but they smelled like pussy! I dropped then, picked them up, and smelled again, ahhhhhhhh, sweet pussy, and a little piss and sweat mixed in.

   I decided to take it a bit further. i finished up pooing, got up, flushed, and pulled my pants up. i then grabbed the panties again, and took them into my mouth. My taste buds exploded as the taste of hearty mature pussy, and cottony fabric mixed in my mouth. I ran my tongue over the crotch time and time again, till the flavor was completely gone. Then i spat them out,  and thought about what i had just done. I had just tasted Jennifer's mature 45 year old pussy, and for her weight, her puss tasted great.

   then it happened. I heard her door open, and the bathroom knob turn. Me flushing must have awoken his mom! out of peer fear and adrenaline. i jumped into the shower, and closed the curtain to conceal my body from her. She opened the door, and quickly tuned the light down, (they had a dimmer). She looked around, as if to find the source of the noise, but nothing was there for her to see. She then walked over the the toilet, grabbed her panties from up inside her nighty, and pulled them down, she lifted the toilet seat, squatted, and a few seconds later, i could hear her pee swishing on the toilet below her. after she just sat, with her eyes closed.

   She sat with her eyes closed for about 5 minutes, and i wondered if she was alright. Then, she snored lightly. She was asleep. on the potty! i carefully maneuvered out of the shower, and stood next to her. I pinched her ear, and nothing happened. I pocked her face, nothing. Then i shook her violently, still, nothing. My horny teenage mind instantly came into effect. I mover over, and squatted between her legs, and spread them open. I had a clear look at her half trimmed bush, still wet from the pee she took. I nudged a finger in, and poked her pussy a little. She moved not a bit. Hmmmm. I got bolder. I touched were her clit was jetting out (it is a very large clitoris). She sighed a little, but nothing more then that. I then began running my finger in and out of her pussy, like a well oiled machine. i couldn't even fathom what i was doing. With my other hand, i ran it up her dress, till i found her left breast. I caressed her nipple, and felt it grow in my hand. I was fingering, and massaging my best friends boobs and pussy!

   Then she moved, and her eyes opened a little. "is that you Ron?" i stopped dead. Oh my god! was she awake, or sleep talking? I toned my voice down a bit, "huh, yeah Jen, just given you a little attention." I had no fuckin idea who Ron was, so i decided to run with it. "oh Ron, yes baby yes, make Jenny come like you used to, before we were married." then i figured it out, Ron was her ex-husband, My friends Dad. Then i saw her eyes open a little more, and i panicked, i took my hands off her body, and jumped back into the shower, and closed the curtain, but peeked out with my left eye. she did indeed wake from her sleep, and she looked around hoping to find her Ex in the room, but he wasn't of coarse. she yawned, then spoke to herself, "oh well, just a dream. I need a cock, i need a man who can touch me like him." She got up, flushed the toilet, opened the door, and walked out. i waited a solid ten before exiting the shower. Oh my god, that was crazy, and at that moment, i got an idea, a sexy, naughty, evil idea.

-To be continued