My Bullies and My Mom Continued

I'm going to make the assumption that most of you who are reading this story have already read the first adventure involving Caleb and his 40 year old milf mom Janice.

18-year-old Caleb found himself in a dilemma.

His skirt chasing dad had always told him, "Son, opportunity only knocks once. It is up to you what you do with that opportunity."

Caleb's opportunity was literally laying before him in the form of a totally naked, bound and blindfolded 40 year old big tit milf mom. The dilemma was that the bound and blindfolded milf spread out before him also happened to be his mom.

Caleb had just experienced the sexual highlight of his life. He had just had the pleasure of witnessing the sights, sounds, and aromas of his 40 year old trophy milf mom Janice being mouth, pussy and ass fucked by his 18-year-old black bully Jerome who had been tormenting him for years.

Caleb cut a deal and participated with Jerome to put an end to his bullying. Caleb sacrificed and offered his milf mom to Jerome for him to sexually molest her anyway he wanted for as long as he wanted. In return Jerome agreed to stop messing with Caleb, not only at school, but also out of school. Jerome took advantage of his opportunity.

What Caleb did not know is that his mom Janice had also cut a deal of her own to let Jerome have sex with her to put it an end to her son's bullying essentially making the sex consensual.

Caleb sat a couple feet away from his mom's bed, gagged and handcuffed to a closet door having a ringside seat as Jerome reenacted the sexual exploitation of Janice that Caleb's father had staged and videotaped with Jermone's father a year before.

Caleb had sedated his mom and helped Jerome carry her up to her bedroom for her sexual sacrifice. Janice was layed on the bed as both teenage boys stripped, blindfolded and tied her spreadeagled to the bed wearing only her bra and panties. Jerome sliced her bra and panties from her body and threw them at Caleb as souvenirs.

Caleb was beside himself seeing his mom totally naked for the first time. He took advantage of the situation by grabbing his mom tits, and getting the feel of a mature pussy for the first time.

Jerome didn't know if he could trust Caleb while he was molesting Caleb's mom so he gagged him and cuffed him to the closet door so Caleb could watch but not interfere or speak.

Caleb stroked his cock for hours, watching Jerome do everything he could to violate his mom's body. Caleb eventually blew his load as Jerome drained his balls in Janice's pussy and her asshole. Jerome uncuffed Caleb, got dressed and left Caleb alone with his mom which now brings us back to Caleb's dilemma.

Janice was still extremely groggy but was starting to come to while still blindfolded and tied spread eagle to the headboard. Caleb could clearly see Jerome's black man jizz slowly running out of Janice's pussy and asshole as she was still spread wide with her ankles tied to the headboard. As he approached the bed his mom's perfume mixed with the smells of ass and pussy was tempting him.

Caleb stood at the foot of the bed, contemplating what he should do next with his mom. Thoughts were racing through his head. He was remembering how amazing her tits and pussy felt earlier in the evening before Jerome had his way with her. He was thinking to himself,

"Am I actually capable of banging my own helpless, defenseless, mother? She would have no idea it was me. She is literally my own milf."

Caleb then remembered what is father told him, " Son, opportunity only knocks once." That was all it took for Caleb to come to a decision.

Caleb stripped down with this young cock back at full staff looking like a rhino horn. He was horny with lust even though he had just drained his balls minutes earlier watching Jerome raping his mom. He was not going to pass up this opportunity to violate his mom's body just as Jerome and Jerome's father had done.

His mom's tits felt amazing as he squeezed and sucked her nipples like a newborn baby. Janice was responding with cooing and moaning as Caleb licked his way down her stomach enjoying the feel of her toned stomach and well trimmed landing strip on his lips.

Jerome's jizz had finally stopped running out of Janice's pussy and asshole. Caleb had never been with a woman before but he had watched enough porn to know his way around a woman's pussy. Caleb alternated between flicking his tongue over his mom's clit and going chin deep in her pussy with his tongue.

Janice was still tied up and blindfolded and was starting to recover from the sedatives Caleb had given to her. As far as she knew it was still Jerome down between her thighs which she had consented to. She did not offer any resistance. It was time for Caleb to literally violate his own 'mother I'd like to fuck' pussy.

Caleb was well hung and put it to good use. He got on his knees, grabbed the headboard with one hand and guided his cock into Janices pleasure palace with his other hand all the way down to his balls.

The thrill of being in his first pussy, let alone his mom's pussy was erotic and exhilarating. After only a couple minutes Caleb could not hold back anymore and let loose a ball draining load while he aggressively jackhammered his mom's pussy making sure not to cry out or make any noise.

Janice was moaning and starting to come to. Caleb made a smart decision to untie her from the headboard, but leave her blindfold in place so he could gather his clothes and sneak out of the room.

He covered his mom with a blanket as his jizz was running out of her puffy pussy lips. He picked up his clothes and also grabbed the videotape at the foot of the bed and took it to his room. He was exhausted and went to bed deciding to watch the video tape the next day.

The next morning his mom acted as if nothing had happened other than a little bit of a sedative hangover. She felt good about herself that she had fulfilled her commitment to Jerome and he had delivered the videotape. However, she could not find the tape.

She asked Caleb, " Son do you know where the video tape is that Jerome gave me last night? It was sitting on the kitchen counter."

Caleb was a smart boy. He was not gonna give to videotape back until he knew what was on it. He responded, "Gosh mom, I have no idea where it is. Maybe Jerome took it with him when he left this morning."

Janice was starting to panic and was upset with herself knowing that she had whored herself out to an 18 year old black teenage bully and still did not have the video tape. Caleb was enjoying messing with his mom and watching her panic since knew right where the videotape was. He was now getting very curious as to what was on the videotape. He would find out later that night exactly why his mom was in a state of panic.

Later that night after Janice had gone to bed, Caleb snuck down to the family room and inserted the videotape in the VCR. He turned the volume down not knowing what to expect. He was immediately shocked at what he saw.

it was almost as if he was watching a replay of what he had just witnessed with Jerome and his mom the night before. Only this time the black man was much older and much bigger than Jerome.

He could hear his dad's voice in the background taunting and talking trash to his mom as the black man progressed from putting his cock and balls in her mouth, to tit fucking her with nipple clamps, to eating her pussy to orgasm and fucking both her mature pussy and asshole with his long, thick black cock.

He listened to his mom screaming in anger at his dad as the black man prepared his mom's asshole with KY jelly. Caleb suddenly realized what was going on.

His mom had been tricked into thinking that it was his dad that was going to sodomize her. He did not recognize who the black man was, but he could tell he was hung like a horse very much like Jerome.

Caleb had no idea it was Jerome's dad raping the hell out of his mom with his dad's blessing while he videotaped the whole thing. Caleb now understood his mom's hatred for his dad and why they got divorced.

Even though Caleb realized his dad was a fucking perverted asshole he still couldn't resist jacking his cock and draining his balls listening to his mom's screams and watching Jerome's dad use his mom as a reparations fuck toy.

Caleb was a smart boy and had a little bit of his dad's nasty, perverted DNA. He had no intention of giving the videotape back to his mom for her to destroy. He was having too much fun watching and listening to her panic over the videotape worrying about where it is and who might see it. He also considered using it as blackmail if he ever wanted to get more pussy from her in the future

He was also getting too much enjoyment jacking off every night watching video of his mom getting molested by the still unknown black man. He decided to invite some of his buddies over one night to share the videotape with them while Janice was having a girls night out with her girlfriends.

They had all seen Janice at the fitness club in her suggestive, prick teasing, Lululemon workout clothes and they all considered her the gold standard for MILFs. Caleb charged them $50 each to share the video with them telling them they wouldn't be sorry.

The 18-year-old teenage boys were not disappointed. It eventually turned into a semi circle jerk with every one of the teenage boys rubbing their cocks through their pants while watching Caleb's mom get pummeled by black cock.

At one point one of the boys recognized the black man and said, "Hey, I know that guy. That's Jerome's dad, Jackson. He is a good friend of our high school principal, Mr. Robinson."

Caleb was beginning to wonder how many other people had also seen the video tape and how many black cocks had the pleasure of fucking his mom.

At around 10 o'clock Janice pulled in the driveway. Caleb immediately shut off the VCR and put in a video game. Janice was a little tipsy, and was not aware that she would be walking into a room of hormone crazy teenage boys who had just watched her get violated by one of their friends dad. The boys had lustful arrogance in their eyes and suggested that Janice hang out with them for a while before going to bed.

Janice was dressed to kill for her night out with the girls. She was wearing a short skirt, low cut silk blouse, high heels and pantyhose.

Janice: "Caleb could you be a sweetheart and pour me a glass of wine while I talk to your friends." Caleb immediately had a plan and knew what to do..

Caleb's friends were immediately teasing and flattering

his mom trying to seduce Janice by confessing how much they enjoy seeing her working out at the fitness center and complimented her on her outfits. Janice was flattered and found herself being somewhat excited from being complemented by all these young men the same age as her son.

She smiled at her son as Caleb handed her a glass of red wine containing three Excedrin PMs that he had secretly ground into powder and stirred into her drink. She would be out within minutes.

Caleb's teenage friends were enjoying sitting on the floor listening to Janice while shamelessly checking out her pantyhose covered legs and cleavage knowing very well what was underneath. They had no idea that Caleb had just sedated his mom and that they would have the opportunity to feel her tits and pussy in a couple minutes. Caleb was going to tease his buddies for future profit, and possibly blackmail.

Janice was starting to get woozy and a little sloppy. She knew it was time for bed. She tried to get up still wearing her high heels, but fell back on the couch, giving the boys a nice up skirt look add her mature thighs and her pantyhose covered pussy.

Janice: "Son, could you and a couple of your friends help me upstairs?"

None of the boys hesitated. They all jumped their feet to help Janice up to her bedroom. Janice was becoming limp and lifeless. It was like trying to carry a bag of Jell-O. Janice was laid down on the bed, still fully closed still wearing her high heels and surrounded by her son Caleb and a group of 18 year old pussy hungry teenage boys.

Caleb shared his dad's wisdom with his friends. "Guys, opportunity only knocks once. What you decide to do it is up to you." Caleb's buddies knew what he was suggesting and they immediately started undressing Janice without hesitation.

Within minutes, they had unbuttoned Janice's blouse, pulled it out of her skirt, and spread it wide open revealing a nice red lace push-up bra. Instead of taking off her skirt, they pulled it up and bunched it around her waist, exposing a very nice pantyhose covered mature pussy. They left her sexy high heels on adding an erotic look to Janice's sexy legs.

Within minutes, Janice had multiple young men running their hands over every inch of her body. Caleb pulled out his cell phone and started taking video. The boys had no intention of raping Janice, but they were going to have a field day exploring her body. The boys would leave her dressed when they were done with her so she wouldn't suspect anything the next morning.

Caleb got video of all the boys feeling up his mom's tits by pulling down her bra off her shoulders and sucking her nipples. Even though Janice was sedated her sensitive nipples were still responding to being touched, sucked on and pinched. The boys were definitely giving her nipples a work out.

Her legs were spread so that each boy could rub his hands over her inner thighs and give her pussy and lick, and a kiss through her sheer pantyhose. Janice was exposed and surrounded by young men getting their own screenshots and cell phone videos of her for their own personal use and maybe future blackmail.

Blackmail was still a part of Janice's life. It was becoming well-known around Caleb's high school that Janice was being blackmailed by principal Robinson to suck his cock on a weekly basis to protect Caleb. Some of Caleb's friends had similar ideas.

Janices situation just got worse. Not only was her ass rape video still circulating but now there were multiple young men that had compromising screenshots and video of Janice that could end up anywhere, including the Internet.

Once the boys, including Caleb, were finished exploring and groping Janice they buttoned up her blouse, pulled down her skirt and covered her with a blanket. She would have no memory of what had just taken place. At least for now.

The next day Janice made her weekly visit to Principal Robinson's office to satisfy her commitment by letting him use her mouth and throat as an oral pussy. While walking through the high school corridor the usual taunting and teasing from teenage boys seem to be a little more aggressive. Janice was intimidated.

Many of them had seen the video tape and had explored her body the night before while she was sedated. They felt entitled and bulletproof since they had cell phone video that they could use for blackmail against Janice anytime they wanted

Mr. Robinson had a surprise for Janice as he escorted her into his office. This time Mr. Robinson had a visitor. It was Jerome's dad, Jackson. Janice was about to meet the mystery black man in the ass rape video.

Principal Robinson: "Janice, I would like you to meet a friend of mine. This is my good friend Jackson, does he look familiar to you?"

Janice: "No, he doesn't, I don't believe we have ever met."

Principal Robinson. "Oh, believe me, Janice, you and Jackson have met. Let me see if I can jog your memory."

Principal Robinson walked around to the back of his desk, opened his desk drawer and pulled out some photos of cell phone screenshots and laid them across his desk for Janice to see. Once again, Janice was shocked by what she saw.

The collection of photos clearly showed Jackson laying his cock and balls on Janice's blindfolded face, sitting on her chest tit fucking her, playing to the camera as he fucked her pussy, and lastly, giving a thumbs up to the camera as his big black cock was finally balls, deep in her spreadeagled, mature, pink asshole.

Janice: "Oh my God, so you're the fucking asshole that my husband hired to rape and videotape me? Jackson immediately defended himself by correcting her.

Jackson. "Excuse me miss, but first of all your husband didn't pay me a penny to bang you. I helped your husband out of the kindness of my heart and for my love of white mature pussy. Especially yours. Secondly, your husband gave me his total consent and directed me to do everything I did with you including fucking you up your ass. Therefore technically it was not rape and it was his idea to have me sodomize you and blow my load in your ass. So I think you owe me an apology."

Janice was torn between agreeing with him and being outraged. She knew her husband had set her up to be ravaged by his big black cock friend Jackson. She knew how attractive she was, and how men at the fitness center, including Jackson, lustfully looked at her as she strutted her stuff in her sexy, suggestive workout clothes. She had some sympathy for him.

Janice: "OK I understand that my ex-husband concocted this scheme so I apologize for saying that you were hired to rape me." Jackson wanted more than just her token verbal apology.

Jackson: Well, that's all fine and well miss. I am very powerful and well respected In the black community. You just slandered my name and embarrassed me in front of another powerful man in the black community, principal Robinson. I think you can do much better than just a simple verbal apology.

Janice: "Well sir, I'm not sure what else I can do other than apologize to you."

Principal Robinson got up from behind his desk and walked over and locked his office door from the inside. Janice now understood what the two black men had in mind. Janice knew the routine.

Both men sat on the edge of Principal Robinson's desk, and slowly unzipped their pants. Janice was in her usual position sitting in front of them with her mature tits tightly packed in her silk blouse, and her legs crossed wearing a short skirt and sexy high heels. Both men approached Janice with their cocks dangling from their pants, fully expecting Janice to offer her oral apology.

Janice got up out of her chair. She knew the script and what Principal Robinson liked having sucked him off every week for months. She stood in front of the two powerful black men watching their black cocks start to grow as she slowly unbuttoned her silk blouse.

Janice wouldn't admit it to herself, but she was starting to become addicted to black cock. She was beginning to love the feeling of a hard black cock pumping in and out of her mouth and occasionally in her mature, milf pussy. Today she would experience both.

Both men sat down again on the edge of Principal Robinson's desk to watch this 40 year old white milf strip for them while stroking their cocks to full attention.

As usual, Janice unbuttoned her blouse, taking it off and laying it on the chair. Janice was wearing a very nice light purple push-up lace bra. Principal Robinson always liked to watch and play with her tits as she worked his cock in her mouth, but today would be different.

Principal Robinson. "Janice, we need a more physical apology from you to my friend Jackson, to make sure you are sincere. Drop your skirt, but leave the high heels on. Janice started to get flustered. Principal Robinson had always been satisfied just playing with her tits and pinching her nipples while her lips were wrapped around his black cock. He had never went after her pussy. Today would be different.

Janice reached around and unzipped her skirt from the back and let it fall on the floor. She stepped out of it, still wearing her high heels. Her thong underwear was a perfect match to her push-up bra.

Both men approached her with Principal Robinson kissing the back of her neck and unhooking her bra. Jackson started kissing her shoulders reaching down to rub her pussy through her lace thong underwear.