The Fall of Principal Baker
PART 1
Tommy and his mother Betsy were on their way home from a Friday night function at his school. There, Betsy was Principal Baker.
Standing at 5'3" in heels, Betsy was average height and weight. Having just turned 50, she had a hair full of graying curly hair, which she typically kept back in a ponytail. She had a full chest, a small waist, and a nice butt. Tommy had gotten an earful from all of his friends about her various attributes for a long time.
And especially that Friday night. She was in a small navy blue dress, that cut low in the front. Lower than what she would normally wear. But a friend had convinced her to buy the dress recently, and she was wearing it out for the first time.
Tommy had been sitting in the audience with his friends while his mom (Ms. Baker to everyone else) had been speaking. His friends, Tyler and his sister Jamie, were not shy with their evaluations of how Ms. Baker looked in that dress.
"She's the perfect milf, man," Tyler whispered to Tommy.
"That's my mom, man," Tommy replied, fully aware of what they were talking about. Just because she was his mom, didn't make him blind. Or not a horny teenager himself. But it was awkward to hear, especially when the entire school knew who she was.
"She does look amazing in that dress," Jamie chimed in. She liked both boys and girls equally. "Has she always looked that good?" she asked, rhetorically. "Or is she getting hotter with the more gray hair she gets."
"I think that's part of it," Tyler added, shamelessly breaking down the milf-ness of his best friend's mom, while sitting right next to him. "I like how the zipper is pulled down just enough to see a little of her cleavage. Man, I'd kill to pull that down some more...."
"Mmmm," Jamie added. "Get that hot little dress off and see what's underneath." Jamie was quite brash, and was famously quite a horny little package herself.
Tommy just considered her a friend, however. In part because Tyler would probably kill him if he ever touched his sister. Still, Tommy found her red hair and braces, and tight little body, quite attractive.
"Alright, got it," Tommy sighed, while at the same time crossing his right leg over his left. He wouldn't say it out loud of course, but he was having similar thoughts. She looked that good. Tommy internally scolded himself.
"Well Tommy's the one going home with her tonight," Jason noted. "Give it a shot dude."
Tommy punched him in the leg. "Not funny."
A short time later, and Betsy and Tommy were on their way home. Tommy was driving, allowing his mom to catch up on some business on her phone. He stole glances at her in the passenger seat, her face lit up by the light from her phone.
Her nose scrunched up when she read something she didn't like. Tommy smiled. His gaze then headed lower, until it reached the swell of her breasts, being pushed up by the top of her dress. He watched it rise and fall, before returning his eyes to the road.
Looking now out of the corner of his eye, Tommy felt an erection developing in his pants. He again scolded himself for thinking those things... but then caught himself staring again at her rising and falling chest, in that tight little dress. His erection grew bigger.
Finally, the car pulled into the garage. Betsy continued answering emails on her phone, while Tommy stalled. He was in no condition to stand at the moment, and was still struggling to take his eyes off his mom's low-cut dress.
"Home," Tommy said, the words of Jason and Tyler still echoing in his head: "I'd love to pull that zipper down.... you're the one going home with her". He tried to push them away.
"Ok just a sec," Betsy responded, distracted.
Tommy moved a little closer. "You... um... look really nice tonight mom."
Betsy looked up from her phone, smiling. "Thank you honey," she said warmly. "I was a little worried about this dress, but it turned out well."
"Worried?" Tommy asked, now himself a little worried that his mom might be able to see what had grown inside his pants.
"It's just a little more risque than what I would normally wear," Betsy replied, motioning to the zipper and where it was resting on her large chest. "While I was speaking tonight, I was a little distracted, because I thought I might be showing a little too much.... you know. Sorry, too much information."
Tommy leaned in a little closer. "A little too much what, mom?".
"Well, when you are, um, my size...." Betsy started, quietly, "... and your job is teaching teenage boys every day.... it's important to, you know."
Still staring at his mom's chest, Tommy spit out, "You know?"
Betsy smiled. "Important to keep everything under wraps. Lets just say that."
Tommy gulped. This departure in the conversation was not helping his current condition. But Tommy was sitting in his mom's car, staring at her cleavage, while she talked sheepishly about her breasts in front of him. He didn't want it to stop.
"And you were afraid tonight, they.... um, I mean, your, you know.... weren't... um... under wraps?"
Betsy laughed at the clumsy question from her son. "A little bit. I'm very sensitive about that. Gotta always worry about that sort of thing around teenage boys. Can't risk being even slightly inappropriate."
For sure, Tommy thought. He continued thinking: They're so full, and round. I wonder what type of bra she's wearing under this dress. His horny teenage mind was swirling, and his cock was rock hard and twitching in his shorts.
He was no longer scolding himself over his thoughts. He wanted to get her out of that dress.
"Anyway," Betsy started, reaching for the door handle. "That's enough about my attire for the evening. Lets go inside."
Tommy let his mom go first, and then followed behind her, with a huge tent pitched in his pants. Watching her tight little figure walk in front of him didn't help matters. Her nice ass was framed perfectly, and Tommy stared blatantly at it, as his mom opened the door into their house.
Eventually Tommy shuffled his way to his room, down the hall from Betsy's. He went immediately to his bed, and covered his lap with the blankets. In no time at all he had his pants and underwear off, and his monster erection in his hand. He was so horny, and could have gone off at any minute.
He thought only about his mom in that dress. Imagining what he would like to do to it and how he'd like to get it off of her. He began stroking himself faster, knowing he had only seconds left before he blasted off into his sheets.
Tommy was sitting with his back against the wall, facing the door to his room. He had left it slightly open, and as he was about to finish himself off, he saw movement. His mom was standing in his doorway.
"Goodnight Tommy," she said, not really paying attention to what was going on inside of his room. Tommy froze, still holding on to his throbbing erection, while looking at his mom standing just outside of his room.
He gave it a squeeze, and a couple of quick strokes. "Night mom," he said quietly, trying to postpone his ejaculation as long as possible. He certainly didn't want it to happen with her standing right there.
"Hey, everything ok?" she asked all motherly, as she entered her son's room. Tommy was suddenly very thankful that he had multiple layers of covers over his lap. Otherwise his mom would be staring at his throbbing erection, and he couldn't think of much more embarrassing than that.
He continued softly squeezing his cock as his mother sat down in bed next to him, with her back also against the wall. "Yeah mom, just tired," Tommy managed to get out. She couldn't tell what he was doing under there, could she? he wondered.
"You seemed distracted tonight," she continued, as Tommy stole glimpses at her chest. If he wasn't careful, he was going to cum into his sheets with his mom sitting right next to him. That would be difficult to hide.
"Just a lot on my mind," he answered truthfully, as he watched her chest rise and fall. He stared at her zipper, still positioned right at the start of her cleavage. He felt a drop of his precum on his index finger.
"I'm sorry you felt uncomfortable tonight mom," he said, wanting to steer the conversation back to where it was before in the car. "You shouldn't wear that dress to school stuff if it makes you feel that way."
Betsy smiled sweetly. "Oh it wasn't a big deal. Just being overcautious. I have a reputation to uphold you know. Can't be showing off the goods. And besides, it's not like teenage boys would be interested in an old lady like me."
Tommy continued squeezing his cock. He felt it twitch, and moved his hand off to prevent ejaculation.
"Well I think that's ridiculous, mom. You're not old. You looked great," Tommy said, sensing an opening. "My friends were even talking about it."
Betsy looked at him with raised eyebrows. "Tyler and Jamie? What did they say?"
"Um... that you looked hot. And... some other stuff."
"Tell me. What did they say about me?"
"They just talked about your dress, and what they'd like to do to it, and... you know." Tommy wasn't touching his cock anymore, but still felt it twitching. Having this type of conversation with his mom in his bed was about to make him cum.
"And what does 'you know' mean Tommy?" Betsy asked.
Another twitch of his cock under the covers. Tommy eyed the puller of his mom's zipper, just below where her cleavage began. His mind was on overdrive and wasn't making much sense, or making smart decisions. He pulled one hand out from underneath the blanket on his lap.
Betsy turned slightly towards her son. Tommy leaned in towards his mom.
Tommy said softly, "Just what they would like to do to this dress. And what they would like to see underneath." Tommy spoke while barely moving his eyes from her chest.
"I see...." Betsy murmured, almost to herself. "Those kids wouldn't really get excited by an old woman like me, would they?" she asked her son, still slowly moving closer to her.
"Of course mom," Tommy replied, feeling another twitch of his hard cock. The closer he moved to his mom on his bed, the more of the sheets gradually fell off his lap. He was so locked in on her that he didn't even notice.
At about that point though, she did. Betsy looked down and saw part of her son's bare upper thigh. She realized then that he was nude from the waist down. She tried to avert her eyes before she saw anything she shouldn't see.
Tommy continued. "You're really hot mom. Anyone would get excited by you." They were now close enough that their legs were touching. Tommy looked down now into the small amount of cleavage his mom was exposing. The sheet covering his erection fell off a little more.
Betsy tried to look away but couldn't. Most of his bare legs were now visible, with the sheet mainly only covering what she assumed was his naked penis. And judging by the shape of the sheet wrapped around it, her son had an enormous erection. Right next to her.
"Oh please," she started, looking away now. "I'm an old woman with gray hair and glasses. Like that turns anyone on your age."
She quickly looked her son in the eyes, before her own eyes returned to what was happening below his waist. She watched it move closer to her.
Betsy suddenly wanted to hear more. "What else do young boys like about me," she heard herself saying. She had spent years cultivating a persona that was as asexual as possible. Now after wearing one tight dress to a school function, she found herself asking her son what young boys, like him, found hot about her.
Tommy looked down his mom's body, laying essentially underneath him now, with her back pressed against his bedroom wall. His hand ran through her hair, as he eyed the zipper again.
"Um..." he started to answer, not knowing exactly how. "Your legs.... your butt.... your t--." He started to say "tits" but caught himself. "Your breasts."
Betsy felt a current run through her. Again her eyes found his covered erection.
Tommy's cock was pulsating now, and he had to work hard to avoid going off. "They're sort of famous," he said softly, still eyeing the zipper. "Everyone would want to see them. You know, up close. And uncovered."
"Everyone?" she asked, suddenly liking the feeling of being that desired. "Everyone would... would want to see.... me.... 'uncovered'?"
"Everyone," Tommy replied. He couldn't stand it any longer, and reached his hand out to the top of his mom's dress. His fingers found the metal puller of the zipper. Tommy waited a moment for a rebuke, and didn't get one.
His mind was swirling again. He played with the puller for a few seconds, as just silence filled the room. He quickly stole a glimpse at his mom's face. She was looking down her chest at his hand on her zipper. Finally, he began to very slowly pull on it.
Both mom and son watched silently as her zipper fell inch by inch down her large chest. Tommy was in awe, as he watched more of her beautiful, pale white skin become exposed to him. He continued pulling, as more of her cleavage became visible to him.
He was about to get his mom's zipper down past her bra when Betsy suddenly took his hand in hers. She held his hand tight against her now exposed bare skin as she gently shook her head back and forth. She left the zipper where it was.
Tommy eventually released his grasp, and disappointingly laid himself down on his bed. He had been so close. Laying on his side like that, the covers dropped some off of his hard cock. His mom, still feeling stunned and propped up against his wall in a partially unzipped dress, took notice.
Tommy caught her eyes staring at his bulge. He wasn't going to give up. "Why don't you lay down next to me, mom," he heard himself saying. He couldn't stand it anymore, and brought a hand inside of the sheet covering his cock. He gave it a light squeeze, and then another. His mom watched this happen.
"I'm sorry, you've just got me so.... you know," he said, thinking it was probably a good idea to address the elephant in the room. He patted the bed next to him. "Please," he said softly, still stroking his cock under the sheet. "Lay down with me."
The devil on Betsy's shoulder won out over the angel. She paused a moment, before lowering herself down next to her son. She was careful to avoid the sheet now hanging off of his erection.
Tommy took a deep breath, and then started in again on his mom, and his attempt to get her out of that dress. Their bodies were touching, and he was hovering over her, his face just a few inches away from hers. He reached to her pretty face, and slowly removed her glasses, before setting them down on the pillow behind them.
After another deep breath, he began by stroking her hair again, and then let his hand fall down her neck. As he moved his mouth closer to her, his right hand touched the portion of his mom's chest that he had exposed. She jumped slightly.
Tommy's mouth made contact with the side of his mom's neck. He gave her a quick peck there, and then whispered "Please," into her ear, as his fingers caressed her exposed cleavage. "Please let me unzip you," he asked again, as his fingers once again found the zipper. "I just want to see them."
Betsy squirmed in her son's bed, and bit her lip as she watched Tommy again take ahold of her zipper. There was no objection this time, as Tommy began dragging it down his mom's chest. Betsy held her breath, and allowed her son unfasten the front of her dress.
He got it down past her bra, and then down her stomach, before finally releasing it at waist level. Betsy turned her body slightly to where she was facing her son laying next to her. Tommy took his right hand, and slowly peeled the left side of her dress off her chest. And then the right.
He stared down at his mother's completely exposed blue bra, and what it was covering. He watched her heavy chest heave up and down right in front of his face, not quite believing this was really happening. He plotted his next move, wondering what else she would let him do.
Would she let him touch her there? Would he be able to run his fingers up inside of her bra? Would he be able to take it off of her? Was it actually possible that he could be moments away from getting his mom topless in his bed?
Tommy didn't wait long to try. He quickly moved his hands up towards his mom's bra-covered breasts. His right hand reached for her left one, and as he made contact with the soft material, he realized that he had brought himself to the brink of orgasm. He felt his engorged cock twitch a couple of times, and knew he was now seconds away from cumming.
He put his hands down on the bed on both sides of his mom, who looked at him quizzically. "Oh god, I'm... I'm going to...." he started, feeling it coming on.
"It's ok, just do it. Just let it happen baby," Betsy whispered to her son. She was trying to sound motherly, but was unsure how it came out. She certainly didn't feel very motherly right then. Or like a school principal. She felt very dirty, waiting for her son to ejaculate in front of her.
Tommy looked his mother in the eyes, and as she caught his gaze, she saw him do something she could have never imagined: Her son had an orgasm inches away from her body. While staring her in the eyes.
Tommy shouted out, as he emptied his cock into the sheet. The force of the blasts was so strong it moved the sheet. Betsy reached up and grabbed it to keep it from falling off entirely, and held it tight against her son's spasming cock, as it continued to trap load after load of his semen.
Betsy's hands were now placed on both sides of her son's erupting penis. She pressed hard against him, keeping it in place. If she hadn't, it would have fallen off completely, and all of her son's cum would be soaking her clothes and exposed skin.
Both of them looked down at his pulsating cock, wrapped by a now-soaking wet sheet. When he finally shot out the last load, Tommy collapsed into the bed.
Betsy released her hold on the cum-covered sheet, and watched it fall against her son's pelvis, as he laid next to her trying to catch his breath. She silently zipped her dress back up, and reached over to his pillow to grab her glasses.
She took a breath. "Tommy, when I put these glasses back on, I am your mother and your school principal. And we will forget what happened here. Deal?"
Tommy finally caught his breath. "Deal," he said, agreeing.
Betsy slipped her glasses back on. "I'll wash your sheets tomorrow. Goodnight," she said, hopping off the bed, and finally off to her own room.
Tommy laid in bed thinking about what had transpired. He still didn't know what to make of what had happened. One minute he was having a normal conversation with his mom, and the next he was trying to undress her. And cumming in front of her.
He came again approximately 10 minutes later, just recounting the events as they happened. And then again another 20 minutes later, while allowing himself to fantasize about what could have transpired: Her tight little dress stripped completely off and tossed on his floor, his hand running up inside of her panties, fingers navigating their way through her pubic hair, on the way to their main prize.
That was enough for him to cum for a third time in an hour.
After that, his mind drifted towards what could happen next. Could this happen again, or anything like it? Tommy barely slept at all that night.
PART 2
The next night, as luck would have it, would have Tommy's friends Jamie and Tyler coming over for dinner. They both came over at about five o'clock, while Betsy, Principal Baker to them, was cooking dinner for the four of them.
As the three kids were hanging out in his room before dinner, Tommy did not, obviously, mention anything about what had taken place the night before. That was one secret he definitely didn't want getting out.
He was sitting on the edge of his bed, and looked down at the bunched up comforter, with no sheet underneath. His mom had washed it, because it was covered in his cum. He had cum, because he had opened his mom's dress and was about to squeeze her tits. He felt himself getting hard again just thinking about it.
"You still with us Tommy?" Jamie asked. "You're not listening to a word we're saying dude."
He wasn't. Pandora's box had been opened for Tommy, and he didn't know where to go from here. All he had been thinking about for an entire day was getting his mom in a similar position to the previous night. And pushing it was far as she would allow.
Dinner was about an hour later, and was a normal dinner. Tommy and Betsy avoided eye contact with each other, while Jamie and Tyler paid more attention to their phones than anything else.
Tommy stole glances at his mom when he could. She was in a small blouse and jeans, and Tommy spent most of the dinner thinking up various fantasies. His mom pinned up against the kitchen wall, bent over the counter, thrown down on her bed and stripped of all her clothes.
After dinner, Tommy was the last to leave the table. It took some work to get his erection down to a place where he could walk comfortably around his friends and his mom.
The kids all went back upstairs while Betsy cleaned up. They started a movie in Tommy's room, but Tommy couldn't even focus on it. More fantasies... his mom in the shower, his mom in her principal's office at school, on top of her desk....
"Hey guys," Tommy said, not able to wait any longer. "I'm gonna go downstairs and help my mom."
Both brother and sister were lost in the movie, and barely acknowledged him. Tommy pushed down his erection and headed downstairs.
The cleanup in the kitchen was already done, and Betsy had changed into her night clothes. Tommy came downstairs to find her on the couch, drinking a glass of wine and checking her emails one last time before heading to bed.
He took a minute to admire her new attire: A long sleeve cotton nightie that buttoned up the front, and pair of matching shorts. It was her typical nightwear, and looked very cute on her little body.
Tommy gathered himself, and sat down next to his mother on the couch. "Hey honey," she said quietly, not looking up from her phone. Tommy stared at her chest, pushing against that soft cotton material.
He thought about how he wanted to do this. He didn't think his mom would exactly invite him to her room to explore her body or anything like that, but he thought that if he steered the conversation in the right direction, he might get there eventually. He thought. He just had to thread the needle.
"I guess we're just not gonna talk about last night, huh," he said, starting things off. He wanted to get the events of the previous night out in the open. He wanted her to talk about it.
Using her principal voice, she looked up from her phone and said "I thought I was clear. We're not going to talk about that again."
"Well that doesn't seem healthy, does it?" he asked, impressed with his improvisation. "I think we should discuss it." Tommy was already rock hard.
"Tommy your friends are right upstairs," Betsy countered with a quick glance up the stairs. "They can't hear about that. Besides, nothing happened, really. There's nothing to talk about."
Tommy could tell she was in a state of denial, and just didn't want to face it. He needed to get her in a different head space. He needed to get her back to where they were last night, when he had her pressed against him on his bed, laying partially stripped, about to get her tits felt up.
"Say more about what you mean by 'nothing really happened'," he asked, searching for an avenue. He wanted to get her talking about it.
Betsy sighed. "I mean.... there was no touching. Nothing like that. Nothing improper. There was a misunderstanding, you had an accident, and that was that."
"First off," he started, "That was no misunderstanding. You're the one who asked me what young boys find attractive about you. Remember? All I did was show you."
"What you did was," Betsy blurted out loudly, before catching yourself, and looking quickly up the stairs for any sign of Tyler and Jamie. She lowered her voice. "What you did was a lot more than show me."
Tommy scooted a little closer to his mom on the couch. A storm had come through in the last few minutes, and the only sound in the room now was the sound of pounding rain outside. Then a clap of thunder.
He leaned in closer. "Why don't you tell me what I did. I'd like to hear it from your point of view."
Betsy took a sip of wine, and then sat the glass down on the table. When she leaned back on the couch, she was slightly closer to her son than she had been previously. Tommy watched her tits jiggle inside of her top, and then settle.
"Fine. You want to do this? You had me pressed against your wall, and then you had me lay down next to you, and then you unzipped my dress. That's it. Happy? You wanted to hear me say it? I said it."
Tommy could see she was starting to get worked up. He wanted to use it. "And what else?"
Betsy adjusted herself, and took another big sip of wine. Again she fell back into the couch, even closer to Tommy. Their knees were touching, and her mouth was inches away from his face now. Another burst of thunder, as she leaned in close to his ear. The sound of rain was deafening inside the quiet house.
She had collected herself, whispering now, on the off chance there were people somehow listening. "I wanted to know what young boys found sexy about this 50 year-old gray haired old lady with glasses. Because it's hard for me to believe young boys would lust after this. That's why I asked."
Tommy moved his mouth next to his mom's ear. He whispered, "And did you get your answer?"
Their cheeks bumped against each other as they took turns whispering into each other's ears, protecting against Tommy's friends overhearing them. "I got a good idea, yes," Betsy answered.
Tommy now. "And what do you think young boys, like me, find sexy about you?"
Her lips brushed up against his cheek on her way to his ear. "Considering you then immediately unzipped me, and then..." she paused, considering whether to say it out loud. "Then you were about to touch me over my bra, I would guess you like my...." she paused again. "Breasts."
She said the last word much more quiet than the others. Tommy found his hand on her leg. Betsy glanced down at it, and let it go. "You're right," Tommy answered quietly, staring again at her chest in the little cotton top. Her little hard nipples were visible, poking through the fabric. "Anything else give you that idea?" he whispered into his mom's ear.
Betsy paused, feeling her son squeezing her thigh. Each time they had exchanged whispers, they had gotten a little closer to each other, huddled together in the middle of the couch. Betsy again looked upstairs to make sure no one was watching.
Her lips touched his ear. She thought better of it, before whispering to her son, "You came just from looking at my chest in my bra."
Tommy smiled, as his hand moved further up his mom's leg. He leaned in to whisper into her ear, continuing their little game. "I did. That's how hot you looked. What do you think would have happened if I didn't cum?" he asked, and before pulling back, gave her a soft kiss behind her ear.
Betsy felt a shudder go through her, both from the question and the kiss. She had never heard her son say the word cum like that before. "What do you mean," she asked quietly. She felt her son's hand moving further up her leg. It was approaching her inner thigh. She thought about stopping him, but didn't.
Back to his mom's ear, "If I hadn't have cum when I did, what do you think would have happened next?". When Tommy moved his mouth from her ear, this time he kissed her cheek, about an inch or two from her lips. His hand moved up as far as it would go, and he gave her inner thigh a squeeze.
Betsy shuddered again. She glanced again upstairs, to make sure they weren't being watched. She heard nothing from Tyler and Jamie. "I would guess...." she whispered into his ear, allowing herself to say it out loud, "That you would have tried to get my dress off."
Another clap of thunder, as Tommy gulped. He leaned in, and whispered to his mom, "You would have just been in your bra and panties."
Their cheeks pressed together, Betsy replied with a very soft "Yes."
Back upstairs.... Jamie and Tyler were half paying attention to the movie and half playing on their phones. "Where the hell is Tommy?" Tyler asked his sister.
Jamie didn't even look up from her phone. "Yeah, it's been awhile. I guess there was a lot to clean up. Let's wait a few more minutes and then head down there, after everything is already done."
Tyler laughed. "Sounds good. I'm hungry again anyway."
Back downstairs... Tommy ran his fingers up the outside of his mother's shorts. He leaned in, "And then what?" he asked into her ear, before moving his lips next to hers. He kissed her on the edge of her mouth.
Betsy was trembling. She continued their game, and moved her lips to her son's ear. She felt him pawing at her legs through her little shorts. "I'd guess... you would have wanted to get under my bra."
Tommy stirred, and Betsy adjusted her legs. As she did so, she brushed up against Tommy's crotch. It was rock hard. Again. Betsy thought to herself, I give him rock hard erections.
Tommy whispered again. "Tell me one more thing I would have done." He moved his lips now to his mom's, and kept them a fraction of an inch away from hers, before she pulled back slightly.
"I think," she started, regaining some composure as they both heard a massive clap of thunder, "That you might have tried to do some things to me that you would have come to regret." As she finished, she felt her son's fingertips make their way under the base of her shorts, at thigh level.
Tommy's eyes were all over his mom's chest. He could tell her nipples had hardened during their little talk on the couch, as they looked like they were about to pop through her top. He could make out their size and shape. Tommy wondered if he would get the chance to feel them.
He moved even closer, his lips again just next to hers. He felt her chest press against his, as he moved his hand farther up his mom's bare skin under her shorts.
Back upstairs.... "Ok I think that's enough time," Tyler said, putting down his phone. "They have to be done cleaning up by now. Let's grab some dessert and go get Tommy. He's missing the entire movie."
"Sounds good," Jamie said, also putting down her phone. Both kids got up and opened Tommy's bedroom door.
Back downstairs.... Tommy was squeezing his mom's bare thigh, and ogling her heaving chest. Their faces were so close together that her glasses were bumping up against him. That gave him an idea.
"Last night," he started, reaching for her glasses, "You said that when you put your glasses back on, you're my mom and principal." He slowly pulled them down off the bridge of her nose, and sat them down next to her glass of wine. He looked at her now stripped of her glasses again. "Good. Where were we".
Tommy leaned into her, pressing her up against the back of the couch. He took her hands in his, and placed them behind her head. He did a check upstairs for his friends, and heard nothing. Betsy looked back at him, her breaths now coming in quick bursts.
He slowly lowered his head down to her neck, and gave her a soft kiss there. He moved his mouth towards her face, and gently kissed her cheek. Betsy felt one of his hands grab the base of her pajama top, while the other touched her exposed skin, just above the first button on her top.
Tommy drug his index finger down the middle of his mom's pajama top, touching each button on the way down. He watched her breasts rise and fall underneath. His finger moved to the right, tracing circles against her tit. He stopped at the hard bump poking through the material.
"Tommy," Betsy whispered quietly to her son, as she looked down at his finger, and what it was touching. She took his hands in hers, and looked down at what was protruding from his shorts. His massive erection did not leave much to the imagination. She took a deep breath. "You came very quickly last night. Are you close to cumming now?"
Tommy couldn't believe the question from his mom. He sheepishly replied, "Maybe." He was telling the truth. He was worked up again, being dirty with his mom on the couch with his friends upstairs, and it wouldn't take much more for him to cum in his pants.
Betsy eyed the bulge in her son's pants intently. "I don't want a repeat of what happened last night. And I don't want to be washing out your pants later tonight."
Her little hands started to move closer to her son's waist. She watched them, almost as if in a dream. "So either promise me that won't happen again, or..." she started, her fingers finding his belt buckle, playing with it. "Or we should take these off, so you don't make a mess in them."
More massive rain outside, and more thunder. The dark room was lit up by a huge bolt of lightning. "I can't promise that," Tommy said softly, watching his mom's hands fiddle with his belt buckle.
"Ok, then they need to come off," Betsy replied, pulling her son's belt back, and releasing it from its hole. She quickly had it undone.
Her fingers moved to the button on her son's shorts, which she had unbuttoned in a second. Then it was her turn to unzip him, as she dragged the zipper of his shorts down, exposing the pair of black underwear he was wearing underneath. She started to tug on the waistband of her son's shorts.
Back upstairs.... Jamie and Tyler walked through Tommy's bedroom door and headed for the stairs. They couldn't hear anything downstairs, but that was mostly because of the storm outside. They expected them to be talking somewhere, or watching tv.
Back downstairs.... Betsy stared at her son's hard shaft poking against his underwear, not believing what was happening. Seeing what she was causing in her son gave her a feeling that she knew she wasn't supposed to be feeling.
She took her son's shorts by the waistband now, and began pulling them down, careful to leave the underwear in place. A moment later and Betsy had taken off her son's shorts and tossed them on the couch next to the two of them. She glanced upstairs again, just to make sure. She heard nothing, due to the storm.
Betsy returned her gaze to her son's underwear, and the enormous bulge inside. She put her hands on Tommy's upper thighs, with her thumbs pointed inward. The tips of a few of her fingers were touching his member through his underwear. Precum was now leaking out of his trapped cock, and Betsy watched more form against the black material.
Back upstairs.... the two siblings slowly started heading downstairs. It was dark inside the quiet house, so they took their time. They reached the bottom of the stairs, and the only sounds they heard were coming from the bad weather outside. Another large clap of thunder filled the air.
They tried the kitchen first, looking around there, and then the dining room. No Principal Baker or Tommy. Her bedroom was next to them. It seemed doubtful, but they peered in. Nope, not there either. That only left the living room. They must be in there watching tv, the kids thought to themselves.
Back in the living room.... Betsy eyed the button in the middle of her son's underwear. Tommy now had his back pressed against the couch, and his palms flat on the cushions. He watched as his mom slowly moved her fingers up the length of his shaft, until they reached the button. Her fingers touched it, and she left them there for a moment.
Tyler and Jamie rounded the corner at this point, almost to the living room. They were only seconds away. What Tommy and Betsy were doing on the couch would be revealed. Their secret would be exposed.
Mom and son had both forgotten completely about his friends, and were lost in their own world. Betsy's fingers took ahold of the button on her son's underwear. She toyed with it for a moment, before sliding it through the hole.
Tommy's underwear had been opened. Betsy took both sides of the small opening, and gently pulled them apart. Tommy tried not to buck his hips, as his mom carefully opened up the hole in his underwear as far as it would go.
Betsy lowered her head down closer to her son's lap. She saw a flash of white skin, and aligned the hole in Tommy's underwear over the tip of his penis. She finally got it how she wanted it, and began to pull down on the material. The glistening, wet head of her son's cock popped out through the hole in his underwear.
The two kids entered the living room.
PART 3
They stopped immediately, shielded in the darkened room by a living room chair. Jamie brought a hand to her mouth, as she saw what was happening: Principal Baker was staring down at her son's massive erection, covered only by his black underwear. "Oh my god," she heard her brother exclaim, quiet enough to not be heard.
"Jesus Christ," Jamie said quietly, as she watched her principal fiddle with her son's underwear.
"She's not going to...." Tyler started, as Betsy pushed more of her son's cock through the hole. The head and most of the shaft were now visible, just underneath Betsy's face.
Betsy glanced up at her son's face, staring at what she was doing to him. She wondered if he was close to cumming. She returned her gaze to his underwear, and his partially exposed penis. She applied more pressure, and the entirety of her son's cock emerged from inside of his underwear. All eight, hard inches.
Betsy stared down at it, mesmerized. She watched it throb, and twitch. A bubble of precum leaked out of the tip. She watched it dribble down the hard shaft, as her left hand grabbed it around the base. Betsy felt the wetness against her finger.
She took a moment to really look at her son's erection in her hand. It was large, and veiny. And very, very hard. She brought her other hand to it, caressing the wet tip. Tommy remained fixed on the couch, hands flat next to him, watching his mom worship his hard cock. He was trying desperately not to cum.
Betsy took her index finger, and ran it through the precum on the tip of Tommy's penis. She spread it around the head, and gave his cock a squeeze. This produced more precum, which she spread over the length of her son's cock.
She had just begun to gently stroke him up and down with both hands, when Jamie turned to whisper something to her brother. No words came out, but instead a rather loud cough. Everyone froze, including the mom and son in front of them, just as mom's delicate handjob was about to begin.
Betsy turned around and was horrified by what she saw. Tommy looked up from his mom's grasp on his cock to see his two friends. Watching them.
Betsy spoke first. "This isn't what it looks like," she muttered, unconvincingly. Her hands were still wrapped around her son's exposed cock.
Jamie and Tyler slowly moved towards the couch, and sat down on opposite sides of their principal, still holding her son's hard tool. Jamie moved in closer to get a better look. "I want to watch," she said to her principal.
"Jamie," Betsy tried, knowing there was no way out of this. They had been caught. She had been caught, about to give her son a handjob. "This isn't--"
Jamie interrupted her principal to ask sweetly and innocently, "Are you going to make him cum?"
Tommy involuntarily bucked his hips at this. He stared at his friend, with her pretty red hair back in a ponytail, and her mouth full of braces. He couldn't believe she was staring at his erect cock.
Betsy held onto it still with both hands, and dropped her head in defeat. She could have walked away, and tried to later salvage something from the situation. But she didn't
She slowly brought her head back up, into the gaze of her son's veiny hard erection she was holding in her hands. She gave it a squeeze, and gently applied pressure up and down with both hands.
Jamie moved closer, feeling wetness in her little pink panties. "Where are you going to make him cum, Principal Baker? On his stomach?"
Betsy closed her eyes momentarily and shuddered. The sound of thunder again filled the room. This couldn't be happening, she told herself. Her students were watching her jerk off her son on their living room couch.
She ignored the question from her horny young student, and refocused her attention on the throbbing member in her hands. But it did get her thinking: Where did she want him to cum?
She immediately had her answer, as she felt herself leaking inside her pajama bottoms. One quick glance at her students, and Betsy began lowering her mouth down to her son's cock. She was going to make him cum in her mouth.
Tommy's eyes widened, as he watched his mom slowly lower her face down to his penis. She stopped just short of the tip, and took a second to collect another round of precum on her index finger. She lifted it, causing a string of her son's precum to stretch from the tip of his cock to his mother's finger.
Betsy put her finger to her lips, with the stream now connected from his cock to her lower lip. Tommy fought off ejaculation, as his friends scooted even closer now. Jamie was now so close that her leg was touching her principal's leg, and watched her slowly lower herself down to her son's hard cock.
Betsy opened her mouth as wide as it would go, as Tommy's waiting cock approached his mother's mouth. His cock penetrated her lips, and he could immediately feel the warmth inside of her. A bright flash of lightening filled the room, lighting up Betsy's face, her mouth agape, as she prepared to take all of him in.
She lowered herself more, and as most of his cock filled up her mouth, and as she was about to close her lips around her son's hard, veiny cock... Tommy grabbed his mom by her cheeks.
He held her like that for a moment, before slowly pulling her off of his pulsating cock. He would not have lasted very long at all. Five seconds, maybe. He pulled his mom's face close to his own, her mouth still open wide. She stared at him silently, panting.
"As much as I would love to cum in your mouth right now," he said to his delirious mother. "I'm not ready quite yet."
His two friends looked on, slightly confused. Their principal was about to blow her son, and he stopped her.
Then, Tommy reached underneath his already worked-up mom, and grabbed her by her two pajama-covered ass cheeks. She made a little noise that was part surprise, and part moan.
Tommy took a moment to feel them. She was in amazing shape, and her ass felt great in his hands. He gave her cheeks a few more squeezes, before lifting her up by them.
Betsy looked down, as her son lifted her up by her ass, and began pulling her up and over to his cock, still exposed and pointing straight up in the air. Betsy shrieked as he sat her down on top of it. If she had not been wearing pajama bottoms, vaginal penetration would have been instant.
Bullseye, Tommy thought. His mom shouted out and moaned, as Tommy began rubbing his cock up and down his mom's pajama bottoms. Before long the cotton material was wet with what had been leaking out of Tommy's cock.
Betsy leaned into her son, as she allowed his exposed cock to repeatedly push into her pajamas. Between the friction caused there, as well as Tommy pawing at her ass with his hands, the little shorts were pushed up as far as they could go. The two teenage twins were treated to a good portion of their principal's bare ass cheeks.
Tommy's friends looked on, watching him impale his member into his mother's shorts. Betsy fell into him more against the back of the couch, biting her lip. Her covered breasts were just under his face, and she bucked her hips as she felt her son's cock pushing up into her through the wet fabric.
Tommy squeezed her ass through her shorts, and gave her a few more hard pumps into the wet material, before that familiar feeling came back: If he didn't stop right now, he was going to cum.
A bright flash of lightening again filled the room, as Tommy easily lifted his mother off of his twitching cock. She looked down at his hands, as he picked her up, and laid her down on the couch, on her back. The two other kids gathered around her on each side, as Tommy straddled his mom, his hard, exposed cock pointing directly at her chest.
Betsy looked at the faces of her young students. Their eyes were trained on her little body, and her son's huge erect penis, just inches away from her. Betsy looked up at her son now, as he lowered himself down onto his shaking mother.
His face was soon hovering over hers, as he again pushed his cock up against her bottoms. Jamie moved up closer against her principal. She looked at mom and son's lips, separated by only a few inches. "Kiss her Tommy."
Betsy quickly looked at Jamie, before returning her gaze back to her son. "Do it, Tommy," Jamie repeated, her mouth just next to Betsy's face. "I want to watch it."
Another loud clap of thunder. Betsy was still biting down on her lower lip as her son's lips made contact with hers. She released her lip, and opened her mouth to allow Tommy's tongue inside.
Tommy drug his hard member across his mom's pelvis as his tongue explored the inside of her mouth. Betsy moaned into his mouth as he took her hands in his and placed them behind her head. Their fingers were soon entwined, as were their tongues, as were their midsections, as Tommy resumed humping against her mound.
Jamie and Tyler looked on in amazement, as the next minute or so was spent with Tommy frantically pawing, grabbing, and ripping his mom's little cotton top. As his tongue slid further into her mouth, his hands moved to her shoulders and began aggressively pulling down on the sides of her pajama top.
A tongue running up her neck.... a tongue in her ear.... pressure applied to her top and a button gets torn off... more pressure, and another button falls away.... a horny tongue back in Betsy's mouth as she felt the base of her top being pushed up off her stomach, and then cold air on her abdomen... more pawing at the top and another button ripped off.
After a minute of this, Tommy finally pulled up and looked at the condition his mom was in underneath him. Her top was pulled down her arms, and about half of the buttons were missing. The base had been pushed up just underneath her breasts, which were somehow still concealed.
Tommy watched her hard nipples poking through the cotton fabric, as he reached for the remaining buttons, struggling to hold her little top together. He took the two sides in his hands, and was about to pull on them, ripping her shirt open, before hearing a soft "Hold on" from Jamie.
Both mom and son looked at her, as she reached for Betsy's glasses on the living room table. Sweet little Jamie took them in her hands, and then applied them back on her principal's face. She pushed them down the bridge of her nose, while her son still held on to her partially destroyed top.
"There," Jamie said, content, looking at her principal in her familiar glasses. "There's Principal Baker." Jamie leaned down and put her mouth just next to her principal's ear, where only she could hear. "You look hotter in your glasses."
Tommy wasted no more time. He lined up his cock against her wet pajama bottoms again, and gave a big push into her engorged, visible camel toe. The head immediately sunk into the cotton material.
As Betsy moaned and tilted her head back against the couch, feeling the tip of her son's cock press into her, she also arched her back, pushing her chest upwards. Tommy took the two sides of her top in each hand, and pulled as hard as he could.
Betsy moaned again as she felt her son ripping the rest of her favorite pajama top open. She looked down her chest, and at her son's hands balled up into fists, as she watched the remaining buttons break under the strain. One flew off, bouncing off the wall behind them. Another also flew off and landed near the living room table.
She gasped as Tommy ripped the two sides apart. Her large, bare tits were now completely exposed, as Tommy pulled her top off of her, and dropped the sides of his mom's destroyed shirt onto the couch.
All three kids watched her amazing set of tits rise and fall with each heavy breath. Seeing them fully exposed and up close, she was definitely a D cup, Jamie thought to herself, gently rubbing the outside of her little shorts with her finger.
Tommy was fixated on her hard nipples. They were a perfect dark pink color, with matching pink areolas. Her back was still arched, forcing those perfect tits and nipples up closer to her son's face.
Tommy reached underneath his sexually overcharged mom and put his hands on her lower back. He pushed up, arching her back even more, until her right breast collided with her son's face. Her nipple bounced off of his lips.
Jamie slid a finger inside of her shorts as she watched Tommy push up on his mom even more, until her hard nipple slid inside of his waiting mouth. He bit down on it, tasting it, as Betsy squirmed around on the couch underneath her son.
Tommy pushed up on her back even more, until he was squeezing as much of his mom's tit into his mouth as he could fit. He ran his tongue all over her hard nub, before again taking it in between his teeth, and gently biting down on it. Betsy screamed out, as the house was hit with another enormous jolt of thunder.
As Tommy sucked on his mom's huge tits, Tyler stole a glance away to look at his horny little sister. She was inches away from Tommy's mouth, watching him alternate between his mom's nipples. With one hand inside her pants, Jamie took the other and touched her principal's hard right nipple.
Tommy had just lifted himself off of that one, and moved to the left one. Jamie felt his saliva trickling off his mother's nipple, and collected it on her fingertip. She was frantically rubbing herself over the outside of her pink little panties, as she watched her friend absolutely go to town on his mom's tits.
Tyler watched all of this with a massive erection in his own shorts. His attention was actually more focused on his sister, as she rubbed her little pussy while watching Tommy devour his mom's huge tits with his mouth. Tyler had never seen her worked up like that before, and it made him even harder.
Tommy finally lifted himself off of his mom's nude chest, now covered in his saliva. He took her wet breasts, and pushed them together, rubbing over her hard nipples with his thumbs. Betsy looked through her glasses and down her exposed chest, as her son was allowed free rein of her massive tits, in front of his friends.
Jamie's index finger slid up and down outside of her pink panties, as her brother watched intently. She was very horny now, and curious, watching her half-nude principal laid out next to her on the couch. She took her right hand and ran it down Betsy's side, until she made contact with her pajama bottoms. She lifted them up. No panties underneath.
She finally spoke. "Principal Baker, can Tommy take off your shorts? I want to see."
Tyler moved closer to his sister, as Betsy squirmed on the couch under her son. Tommy's hands drifted south, towards the waistband of his mom's cotton pajama bottoms. He played with the band, as he noticed his mom's eyes locked on his still exposed cock pointing straight up in the air.
Tyler sat next to his sister, close enough that their legs were touching. As Jamie remained transfixed on what was happening between the mom and son next to her, Tyler reached out and started stroking her hair in her ponytail. Jamie didn't move; She just kept watching Tommy and Betsy.
Eventually Tyler's hands moved to her upper, freckled chest. He traced little circles around her pale skin, feeling his erection grow larger in his pants. He dipped his hand lower, and felt the swell of his sister's left breast against his hand.
Tommy continued holding the waistband of his mother's wet shorts in his hands. His cock twitched as he started to pull them down. Betsy sat up and watched her shorts being slowly lowered down. Her son was about to strip her completely naked, with the exception of her mutilated night top hanging off her arms.
Tyler slipped his hand further down his sister's top, until he felt her hard little red nipple brushing against the palm of his hand. Jamie finally took notice, and looked down and gasped as her brother rolled her hard nipple between his fingers. She let him do it.
Tommy pulled more on his mom's shorts, until he saw a small patch of pubic hair. "C'mon Tommy," he heard Jamie urge, as she got her small tits felt up by her brother. "Let's see her pussy."
"Oh god Tommy," Betsy heard herself say quietly, as she looked down at her exposed pubic hair. Tommy paused, leaving her shorts barely concealing her vagina.
Tyler now ran his other hand down his sister's shirt, and squeezed both of her breasts together. She leaned back into him, patiently waiting for the rest of her principal's nude body to be revealed to them.
Tommy pulled down more, ever so slightly. He discovered that it actually took some nerve to expose his mom's pussy to a group of horny teenagers. He waited for her to tell him to stop, but she didn't. He then pulled down hard on her wet shorts.
Betsy sat up on her elbows as she watched her shorts come to rest around her upper thighs. As Tommy stared at his mother's wet vagina just inches from his face, Tyler's hand slipped inside his sister's panties. Her pussy was also soaking wet.
Jamie screamed out as she felt her brother insert a finger inside of her. Then another. Tommy broke off his attention towards his mother's pussy to take a look at Jamie. Her face was contorted, and full of desire, as she got finger-fucked by her brother.
Quickly, Tommy pulled his mom's shorts down her legs and then all the way off. He tossed them across the room, his hand now wet from the various secretions that were on his mom's pajama bottoms.
Still getting fingered by her brother, Jamie said hungrily, "Spread her legs, Tommy." Tommy obliged, and placed his hands on his mom's knees, before slowly pushing them apart.
Betsy looked down her naked torso, and watched as Tommy moved closer now to her gaping opening. She didn't think he would really do it, and was shocked to see her son take his hard cock in his right hand, and begin angling it towards her pussy.
Tyler inserted a third finger inside his sister, as both watched Tommy's cock move closer to his mom's entrance. "Oh god Tommy," Betsy repeated, still on her elbows and watching the head of his cock move closer.
Just before he reached her lips, Tommy lowered himself down on top of his shaking mom. He took a breast in each hand, and kissed her passionately on the mouth. It was almost time. His friends were about to watch him fuck the hell out of his mom.
While their tongues were again intertwined, Betsy's eyes shot open when she felt the head of her son's penis penetrate her lips. She thought he would be content with just the tip, so she screamed loudly into his mouth when she felt the rest of his hard cock sink into her.
Tommy lifted up, and looked down at the sight of his cock completely buried inside of his mom's soaking wet vagina. He stayed that way for a moment, and continued squeezing her tits while enjoying the feeling of her hot, willing pussy squeezing his pulsating cock.
He knew it wasn't going to last long. He had been holding off his orgasm for so long now. He watched as he slowly pulled his cock out from inside of her, until it was all of the way out. Then he watched it disappear again. And again. And again.
He heard Jamie scream out, as her brother pinched her nipple with one hand and brought her to orgasm with the hand, inside of her.
Betsy was panting now, and she too watched her son's cock repeatedly disappear and reappear, in and out of her. She finally laid back fully on the couch, and felt her own orgasm building, as her son increased his speed. Soon, he was jack-hammering into her, with her ass sinking between the cushions.
Tommy continued impaling his mother into the couch, until her full ass had dislodged two cushions, and was being railed against the deck, just above the springs. The force in which she was being fucked against it made Tommy wondered if he was going to break their couch.
Tommy knew he was about to cum, and pushed once more into her, as hard as he could. He heard a spring inside the couch break, as his cock went as deep into her pussy as he could make it go. Both Tyler and Jamie watched in amazement, as their principal got the shit fucked out of her on her couch, by her son.
Finally, Tommy was about done. He quickly slipped his cock out of his mother's eager, hot pussy, and moved it up to her face. He grabbed a handful of her gray hair, and pulled it back, as his penis penetrated her lips and fell completely into her mouth, balls deep.
Brother and sister continued watching with interest, as Betsy got face-fucked by her son. A few more thrusts and Tommy yelled out, as he finally emptied his balls into his mother's mouth and down her throat.
Tommy released her hair, and Betsy continued sucking off her son until every last drop of his cum had been deposited inside of her. She felt her pussy leaking, and realized about half of the couch, and inside of the couch, was soaking wet from her juices.
Still hard, Tommy slowly slipped his dick out of his mother's mouth. He couldn't believe it, he thought. He had really just fucked his mom, in front of his two best friends. He looked over at them, and saw Jamie stroking Tyler through his shorts. A few seconds later, and Tyler had come as well. That made orgasms for all four of them.
EPILOGUE
Slowly, Tommy let his cock travel past his mom's lips, down her neck, and stopped at her tits. He took the head of his penis and rubbed it against each of his mom's nipples, squeezing out one last bit of cum to spread over them.
He was about to push it lower, back again to her pussy for round two. As he again felt himself slip effortlessly into his mother's vagina, they all heard a door open and close. They all froze.
"Oh my god Tommy, it's your sister," his mom said in a panic. She was not supposed to be home from college, 300 miles away.
There was no time to do anything. A second later and Betsy's daughter Jenny was standing at the entrance of the living room. She covered her mouth with her hands as she saw her brother's penis inside of her naked mom.
No one said a word. No one know what to say.... Jenny cocked her head, curiously, and took a step towards the couch. Tommy pushed all the way back inside his mother, as Jenny moved even closer. "Hi sis," Tommy said, as his cock settled inside of his mom. Betsy moaned, knowing her daughter was watching this happen.
Jenny felt a rush, and found herself toying with the buttons on her sweater.
Another clap of thunder rang out, as Tyler flipped his sister over, and peeled off her little white panties. Another flash of lighting, and as the room was lit up, Tyler's cock brushed through his sister's red pubic hair, and pushed into her lips. Then, for the first time, Jamie had a cock inside of her pussy.
Another flash, as Jenny found herself kneeling down next to her mom. Another clap of thunder, as Jenny watched her mom's ass get pounded through the couch cushions yet again.
As Jenny watched her mom get roughly fucked, Tommy turned to his sister and said lustfully, "Take your clothes off. You're next."
One last clap of thunder.
THE END