Old Ladies, Thongs & Hotel Hot Tubs

Which is why he really should have checked his cell phone.

**************

For Janie, things didn't turn out quite as planned.

She instantly regretted letting her friends talking her into dumping Tyler. As soon as she went down to Florida on Spring Break with her friends and saw the atmosphere, it was the last place she wanted to be. This wasn't for her. She wanted to go back home. She wanted to be back with Tyler.

She eventually worked up the courage to call and text him, but she got no response. She couldn't blame him for being mad at her. She deserved it, but she knew that if she could just talk to him she could patch things up. Of course they had disagreements in the past. Nothing this bad, for sure, but they had always been able to talk things out.

Part of her believed that he might show up to rescue her from this predicament, come track her down and take her back home, like in those cheesy rom-coms they would watch together. And if he did, she would never let him go. She would jump into his arms, and they would be together forever. She found herself watching the doors, waiting for her knight in shining armor to save the day.

But he never came.

So Janie was upset. She resented her new friends for ruining things for her. She was sad and upset and heartbroken. She felt alone and vulnerable, which is why she did what she did.

Janie kinda hooked up with another guy.

She was SO not that type of girl. Honest. She had only ever been with Tyler. But when she ran into someone she knew at some bar, one of Tyler's friends, this guy Carlos, she ended up doing things she never did before.

That was how she was talked into getting deep-dicked by one of her boyfriend's friends.

It turned out Carlos did like Janie. More than he let on to Tyler. Sure, he did think she was a bit of a princess. A little bit stuck-up, acted like she was above his frat guy antics. Sure, her tits were nothing special, but she did have a great ass. And there was something about making this innocent little princess take his cock that appealed to the scheming young man.

So Carlos fucked her.

He didn't take it easy on her either. He gave it to her like he did all those other college sluts. He fucked her like her boyfriend fucked those nasty old sluts. Hard and rough. Fucking this stuck-up bitch and cumming all over her pretty face was enough for him to check her off his list. He got what he wanted from her, and after that, he had no use for her.

This was the beginning of Janie's fall from grace. Her corruption.

Because even though she found the sex with Carlos a little rough, when she looked back on it, it was a good memory. Combining that with the fact that, in her state, she didn't have the nerve to stop hanging out with the group of girls who convinced her to dump Tyler, this sent her on the path of hooking up with various random college guys. The once nice, sweet angelic church-going girl became just another college slut, hooking up with random dudes who didn't care about her. None of these encounters would give her the fulfillment she was seeking. The fulfillment she had with Tyler. And they never would.

That perfect love story she once had was now long gone. If Tyler could see her now, he probably wouldn't recognize the girl he once loved.

That Janie was gone.

*************

(Epilogue)

Janie didn't have to worry about Tyler seeing what she had become, because honestly, he had pretty much forgotten all about her. All thoughts of his ex-girlfriend had been thoroughly fucked out of him.

From the moment he got in Sonya's car, he had entered these older women's world. And it started immediately, with Stella riding his cock in the backseat of the car during the drive back.

Sonya established her dominance immediately, letting the other two women know that Tyler would be staying with her. The other two women were so thankful for being a part of this whole thing that they agreed immediately.

Looking at her home, nice but nothing incredibly fancy, Tyler didn't see much in common with her in terms of interests. She loved cooking and gardening and lots of things that many women her age liked. She didn't care about sports or TV like he did. They had nothing in common, but it was in the bedroom where they truly became one. And they became one, again and again and again.

The first few days were just Sonya and him, and most of their time was spent in the bedroom, truly going to town on each other, traveling to new depths of lust together. When she eventually returned to work, he was free to come and go as he pleased during the day, but she would typically give him tasks to accomplish. Being the young man he was, he would prickle at being bossed around, but a flash of her huge tits or a shake of her big round ass would make him very compliant. And his reward was usually sex, so the better he did with his household tasks, the nastier the sex was.

Needless to say, Tyler became very compliant. And the fucking was very nasty.

Sonya was clearly the queen bee, but he would be passed around with Ellen and Stella often, sometimes for quickies, sometimes for days on end. Ellen had even less in common with him, being into even more boring things, like books and knitting, truly older woman hobbies. But she savored the idea of having this young lover, and she loved the idea of dominating him even more. She would try to exert power over him, really exploring that aspect of sex. She liked to tie him up, put him in cuffs. Dress up in leather and make him call her 'Mistress'. She would ride his cock for hours and torture him with pleasure, driving him crazy, denying him the pleasure he sought for hours on end.

His encounters with Stella were almost a relief. She was so thankful for the sex that she was always trying her best to keep him happy. She would spoil him rotten, buying him gifts to keep him pleased. She would always be ready for sex, and she did her best to satisfy his needs in bed. While she at first seemed the least experienced of the three, she quickly made up for it, as the sex between them got nastier and nastier as time went on. After being so reluctant at first, she had become a true anal queen. When young Tyler made her ass cum, her whole body would shiver, and she would moan in Spanish. It was so hot!

It became clear when they returned to school after their Spring Break with Tyler that something was different in them. Stella was walking on air. Ellen was slightly less of a cunt. And Sonya, she seemed like she had taken the throne as queen. The blonde guidance counselor felt like the queen of the school, at least among the faculty. She was getting amazing sex, unlike the stuck-up prudes she worked with, and that gave her a confidence that could not be shaken.

She would proudly show off her new man to her coworkers whenever there would be faculty functions. She would slip on a tight, slinky, indecent dress, hugging her curves, and would lead Tyler arm-in-arm to the party, showing him off, making the prudes turn their noses up in disgust at this unholy pairing. She would even sneak off with him and make out with him in a dark corner. Sometimes, she would even let the other two, Ellen and Stella, play with him, shocking their coworkers even more with their corrupt ways. And when all three fell pregnant at about the same time... wow, the whispers and nasty comments about them got even louder.

Everyone knew something was up, even if they didn't know the dirty details. Each of the women would show off their new pregnant curves. Stella showed off her new belly bump in cute, tight outfits, so beyond pleased with the new life growing in her belly. Ellen's work outfits were typically very professional and buttoned up, and as her tummy expanded, she loosened up just a bit, wearing tighter flattering blouses, showing off her body, to the surprise of the student body. And, as ever, Sonya was quite brazen, wearing tops that hugged her pregnant belly while also showing off her heavy, rapidly expanding, milk-filled breasts, while wearing bras that really let them bounce. These three pregnant sluts sauntered through the school, as if they were truly on top of the world. The younger girls were disgusted at these three nasty older women getting knocked up, and even more repulsed by how they flaunted it. By how fucking proud they were. But none of the older women cared. No, they loved it.

Sonya would take him out in public every chance she got. She loved showing off her young lover. And most of all, she loved seeing all those little young bitches fume with jealousy as she made out with a guy their own age. She would wear skimpy clothes, proud of her huge tits, her big ass, and her generous curves, and she did it without shame. She loved it. And for Tyler, being this out in the open with his love life was strange, to say the least, but it was what he had signed up for, and it was certainly a crazy adventure.

But that was just the beginning.

Sonya also loved making it known to one and all that Tyler was into older women. It was almost her favorite thing, and it doubly served to reaffirm that there was no going back. Everyone in their small town knew the score eventually, which, combined with her naked pride in having this young lover, did cause some issues. Two women in particular, the superintendent of the area schools, and the head of the PTA, both bristled at this unnatural relationship. And the PTA head was looking for any way to get these three skanky older women fired, so she got very excited at this revelation.

The superintendent was named Ms. Patricia Buck. Her name lent to the common phrase passed around the faculty when they knew she was coming, which was: 'Don't fuck with Ms. Buck.' She was a few years older than Sonya, Ellen and Stella, with a well styled crop of short silvery hair, and whenever Tyler had come across her, she seemed incredibly cold and unpleasant. She'd never been married, and Tyler felt for any man forced to be in her presence for an extended period of time, let alone a relationship. Ellen actually got along with her great, and they shared many similarities, but Ellen didn't like that this other woman was prying in their business. And the PTA head, Harper Sanders, was the stereotypical shrill, bottle-blonde southern wife. She was also one the heads of the church, so she lauded her conservative values to whoever would be forced to listen, and acted like her and her reverend husband were better than everyone else. She also proudly boasted that she owed her good looks to her faith-based life, and not the doctors who gave her a few nips and tucks and pumped her breasts up to obscene proportions.

In the middle of one of the many group orgies with Tyler plus the three women, these two came up in conversation as possible problems. Stella was worried about getting in trouble and losing her job. Sonya asserted that things were fine and they wouldn't be able to dig up anything that would get them in trouble. Ellen simply wanted the two women out of their business for good, and came up with an idea.

"They're just jealous," Ellen affirmed, grinding languidly on Tyler's stiff cock, her big, naked boobs jiggling. "They just want some dick! That's what we all want! I say let's just let them have it."

"What?" Tyler asked, confused, squeezing her tits.

"You know you're a fucking man-slut, babe," Ellen replied with a smirk. "Just give them that smile and whip your dong out. You'll have them on your dick in no time."

"C'mon..." Tyler said, pinching Ellen's nipples. "I know you guys keep saying that, like, all old women love me, but... c'mon. I've met them. Those two don't want anything to do with me. And plus, they are, like, really terrible people."

"No, Ellen's right." Sonya interjected, smiling. "You're the answer, Tyler. You need to fuck those two." Tyler looked at Sonya, pleadingly.

"I don't want to." he said, not wanting to get involved with the nightmarishly cold superintendent Ms. Buck and that shrill, loud, hypocritical PTA head Harper. Sure, despite his dislike of them, they had a certain appeal. The superintendent's body wasn't bad, with massive, intimidating breasts, and a good figure for a woman her age. And although her expression was typically icy and humorless, she wasn't really bad looking, for an old lady. She looked very posh. And Harper still had an attractiveness despite the small nips and tucks, her good looks from her younger days still shining through. And her massively inflated breasts did look rather squeezable, but no, he had to put his foot down on this. Plus, the fact that he was being talked about being whored out to other women didn't quite sit well with him at the moment. His conservative upbringing still had some effect on him in that sense. But when he looked up at Sonya, and saw her scheming mind at work behind that confident smirk, Tyler knew she was coming up with something and her next words proved it.

"Let's make a bet, lover," Sonya began. "If I can prove to you that pretty much all older women want your dick, then you will have to fuck those two cunts. But if I'm proved wrong, then you get a reprieve, and you don't have to put a finger on their naked bodies." Pressing her boobs into his face, Tyler was inclined to accept this curious bet.

Sonya aggressively delved deeper into his past, trying to get the name of every older woman who he suspected might have actually wanted him. Tyler, curiously, still not sure where this was going, gave up their names, bringing Ms. Barstow, and Susan, and Cassandra, and even that bartender onto their radar. It took a while for him to catch on, but the three old sluts were on the same page quickly. Even though Tyler had been commanded to forget about his past, these three women agreed that he had to right some severe wrongs.

It was time for him to revisit that past.

The deal was, if these three women could prove that those four women did indeed want to fuck him, then he would have to fuck both Harper and Ms. Buck. But, if even one of them was proven innocent of any desire for Tyler, then Tyler was free and clear of those two nightmare women. They agreed not to tell any of the women that they should fuck Tyler, but if any of them asked about Tyler's relationship with the three, they would tell them truth. In the midst of hot sex with the three women, Tyler agreed to the deal. Tyler didn't even realize the hypocrisy of his objection to being whored out to other women, now that he had agreed to possibly do it for women he didn't dislike. He didn't object to being a whore to other women, just some of the women he might have to deal with.

To the best of his knowledge, all of the women in question were single. Ms. Barstow had never mentioned a husband. The bartender certainly didn't act like she was married. Susan had always been a free spirit, doing her own thing. And Cassandra's had divorced a few years back. But despite this, despite the fact that, theoretically, they could all very well be single and on the prowl, Tyler wasn't too worried. Sure, he did have some slightly suspicious conversations with them at one point, but Sonya and the others were blowing this whole thing way out of proportion. Tyler was confident he would win this bet.

So, due to this little wager, Tyler and the three women were going on vacation, visiting his old haunts, his old life, starting with heading towards his old college.

The first woman on the list, the bartender... there wasn't much hope of her turning him down, to be honest, so he figured he could just get this one out of the way. His only hope was that she wouldn't be at the bar when he and Sonya and the others visited, but sure enough, she was still there, jiggling behind the bar. And her bulbous tits were still being brazenly exposed to the mostly college crowd, many of whom Tyler recognized. But while they were all chatting up with hot young coeds, Tyler was there with three big breasted middle-aged women. A fact not lost on the people he knew, or on the bartender, who's cleavage seemed to get even more exposed when talking to him, and who's bra seemed extra bouncy, letting her luscious, mature breasts jiggle.

Tyler quickly found out they tasted as good as they looked.

Their encounter was hurried, an illicit fuck in the back of her car in the parking lot after hours, her smothering his face with her giant, mature breasts, bouncing on his teenage cock, squeezing it with her tight, mature cunt. It didn't take much effort for them to get to this point. She had seen him staring, and sensing a possible hook-up, she acted fast, and hot, steamy sex quickly ensued. She was very excited, and she practically gushed all over him. It was clear that very few of these young, college-aged studs ever took her up on her generous offer, so she made it a point to give Tyler her best. And she did, fucking him like an absolute fucking whore. She wanted to make this night a memorable one, which she did, and in the process she got the best sex of her life. She did get a phone number out of him by the end of it, and while he didn't expect to ever see her again, it wasn't impossible. And plus, there was the concept of dirty texts and sexts, and this woman struck him as being very dirty.

But this was just one woman, and there were three left. Plus, she was pretty much a slam dunk. There wasn't much doubt that she wanted to bang Tyler. But the other three women, those were women he liked and trusted. He highly doubted their kindness and generosity was a façade, born out of a hidden urge inside them to have hot, nasty sex with him. It was completely ridiculous!

Next up, Tyler ended up visiting his old high school, with his three lady friends. He was still recognizable to a lot of the staff, and even though they were happy to see him again, all of them gave him strange looks at three pregnant older women accompanying him. But Ms. Barstow... she was VERY happy to see him. Hugging him tightly, feeling his taut young body against her mature frame, filling him with a bit of concern. She was intrigued by Tyler's new friends, and they clearly had a lot of things to talk about. He could see the moment they dropped the truth on his old teacher, of the nature of their relationship. And instead of being put off and baffled by this illicit relationship, Ms. Barstow turned and gave him the most heated, horny look possible, making him gulp. When they rejoined with Tyler, Sonya explained that they agreed that it would be best for him to reconnect with his old teacher for a bit by staying at her house for a few days. Tyler didn't know what else to do other than agree.

So, yeah, it turned out Ms. Barstow did want to fuck him.

Tyler and her spent the weekend reconnecting, alright, but whereas before, their relationship was connected by intellectual curiosity and warmth, it had now descended to a connection between his fat penis and her mature cunt. Feeling his favorite high school teacher wrap her legs around him, dig her nails into his back, and moan his name into his ear was a brand new level of depravity, even after all the filth he had taken part of. Cumming in his high school teacher's cunt and squeezing her big tits was something he never would have imagined doing. By the end of their weekend together, it became clear that Ms. Barstow had become fast friends with Sonya, and when Sonya invited her new friend to visit Florida sometime, Tyler knew it wasn't the last time he had seen his old teacher.

So that was two of the women. Okay, 2 out of 4 wasn't so bad, right? But, surely, Susan would object to any accusation of impropriety between him and her. She didn't want him in that way. She was practically family.

Knowing there was now distance between him and his family, Susan was surprised to see him at her doorstep. Surprised, but excited, especially after talking a little bit to the women accompanying him. Sonya and her talked for a little bit and handed her new friend a small box, and as Sonya and the other two women gave the old friends time to reconnect, Sonya suggested they go for a swim, just like old times. Susan seemed excited by the idea and gave Tyler the same tight trunks he had worn the last time he swam there. But when Susan emerged by the pool wearing a hot pink, microscopic thong bikini, matching the one Sonya had, Tyler knew what Sonya had given to Susan as a gift, and she was using it to shamelessly and excitedly flaunt her curves. It was clear immediately what she was looking for. And seeing his family friend's huge tits so exposed, and her hot, mature ass jiggling in front of him, nearly bare, Tyler saw red.