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Caitlin had a thing for older men, especially married men. It wasn't exactly a daddy fetish, though Caitlin did enjoy cockteasing her own father. It was more to do with the fact that Caitlin knew her nubile nineteen-year-old body was hot. Her tits were large, her ass was round, and she had the pouty but innocent look of a girl that had always made men fawn over her. It was a face that looked incredibly innocent, even when stuffed full of hard cock or sprayed with semen. It was a face that men loved to deliver a little slap to, for fun, and that just made Caitlin's little pussy go all kinds of gooey.
Boys Caitlin's age were nothing like an older man. They bought her flowers and held her hand. They wanted to take her on dates, sit in movies, give her little kisses and got a bit timid when pushing to get a feel of her tits. Caitlin preferred the take charge attitude of older men, the kind that looked at her like a sexy little wet hole full of pleasure.
Older men were rough and dominant with her, her innocent look giving them the impression that Caitlin was inexperienced and virginal. Those qualities set those older guys off, and it was like they just had to ensure that she was ruined for every boyfriend that came after they'd savaged her teenage pussy. And savage that pussy they did.
Caitlin never came from screwing around with guys her own age, who might be clumsy and fumble with her bra straps. They were hasty, overeager, pumping their hard pricks into her and spewing loads within a minute then asking, "was that good for you?" to which Caitlin would usually just sigh and make them feel embarrassed. That was its own kind of reward, making the boys feel inadequate as fuck toys, which is why she continued to allow those boys to pump her always wet little snatch.
By contrast, those older men manhandled the girl as if she belonged to them. They pushed her down, mashing her tits into the floor or the bed, and parted her lean legs with their knees. They'd hold her arms and hammer her puffy, sopping little fuckhole with their big man-cocks, as though she were a mailorder sex doll that they hid from their wives. Older men were not shy of grabbing her hair and pulling it back, thrusting angrily into her from behind with a firm grip on her bottom and their pelvis smacking the round globes of her ass with no regard for her comfort. These men readily put a dominant hand on her head and fed the length of their jerking dicks into her mouth with never a pause when she gagged, sputtered, or squealed. The little protestations, in fact, only seemed to further enflame their passions.
***
Caitlin loved babysitting for Larry and Tish. The couple were wealthy, paid great, and the kid was easy. What Caitlin really enjoyed about the gig, though, was cockteasing Larry. She even enjoyed doing it when Larry didn't know it was happening.
Whilst the couple was out for one of their many evenings, socializing or attending events, Caitlin would use the time to snoop. There were small things that gave her pleasure, keeping her twat wet and excited. Pushing Larry's toothbrush up her fuckhole and coating it in her pussy nectar, while rubbing Trish's through her ass crack was one of these pleasures. Smearing one of Larry's ties with a film of her cunt honey or making use of Trish's dildo was another.
There was a feeling of perverse joy in knowing that Larry would wear the tie to work and, possibly, smell her arousal around his neck. Equally satisfying was the knowledge that Trish would fuck Caitlin's own fuck lube into her cunt the next time she masturbated. The occasional piss into Trish's shampoo or putting pinpricks through all of her condoms were, also, small acts that gave Caitlin that glorious, juicy feeling and twinge of perverted satisfaction. If Trish ended up pregnant, that was her problem. It just meant that Larry might need to take out his frustrations on a readily available cock tunnel.
As a film student in college, Caitlin was excellent with the computer. Larry and Trish had recorded numerous videos of their fuck play. Caitlin could admit that Trish was a good looking woman as she watched their hidden USB drive of homemade porn, but Caitlin also knew that she was younger and hotter. Caitlin had carefully doctored many of the videos, inserting a frame or two of her own nude body into them. The frames would hardly be noticeable, unless someone actually went frame-by-frame through the video. It gave Caitlin a little thrill, though, to know that when the couple replayed these movies that they would still be treated (however unknowingly) to the sight of Caitlin's naked tits or pussy.
Caitlin's other flirtations were more noticeable. The cocktease had mastered the awareness of her surroundings and found it almost second nature to bend over at the right time to give a man the right view of panties under her skirt, or the downblouse view of her firm teenage melons. A casual brush of the hand against a cock or a seemingly innocent peck on the cheek, while on tiptoes, that ended with a slutty little moan or whimper of desire, were things that came as naturally as breathing.
A nighttime swim in the couple's pool on summer evenings, she'd found, was an excellent way to flaunt herself. Always careful to be out of the water and covered by a towel when they came home, Caitlin was adept at "adjusting" the towel, her top, or her bottoms when Larry could see and Trish could not. Only days after accepting the job it had become commonplace for Larry to linger and small talk with Caitlin, while Trish busied herself checking on the kid or with some other small task, firm in the knowledge that the innocent Caitlin was a chaste and virginal teen with no designs on her hubby.
This role, Caitlin was excellent at playing. She never dressed in a way that could be called slutty when hunting for her next target, unless it was something that fit the situation. With a married man, like Larry, Caitlin would ensure that she always arrived at the couple's home looking cute, just a touch sexy, but her innocent look never giving the impression that she was dressing to entice.
On this particular evening Caitlin knew that Trish was going to attend a work function on her own, while Larry would be attending his own event, which was expected to end earlier in the evening. An hour before her arrival she phoned Trish (always routing all her communication through the wife) and informed her that she was having some car trouble. This was a falsehood, but as expected Trish enlisted Larry to pick the girl up and take her home for the evening. Caitlin, now, found herself in the passenger seat of Larry's car, woefully discussing her financial distress.
"My dad insists that I pay for my own expenses for class," she explained, her lip quivering slightly, "since he's paying my tuition. There's so much stuff to get, though."
Larry nodded understanding, giving her bare legs a sidelong glance where Caitlin's skirt had "accidentally" ridden up far too high.
"Some of the girls I know have started doing some stuff online to make extra money, and they said it pays really good," Caitlin went on.
"What kind of stuff?" Larry asked, his brows furrowing.
"Well, it's a little bit naughty. Some of them do a website called OnlyFans, where they put up videos and sexy pictures. One of them even does an escort job, where she goes on dates with people for money."
Larry choked a bit at the answer and said, "Uh, I suppose that's one way. I could just talk to Trish about upping your pay a bit, though."
"That's really sweet," Caitlin said, laying her hand on Larry's leg, close to his crotch, "It would help, but I really need to make more. I mean, I don't know about taking off my clothes or taking pictures in my underwear," she said, blushing adorably, "My dad would spank the heck out of me if he found out."
She felt a jerk in Larry's pants at the mental image this comment, no doubt, conjured in his mind. Caitlin knew that Larry enjoyed spanking his wife's bottom frequently in the bedroom.
"There's something kind of exciting about going on dates with older men," she continued, removing her hand, "I mean, I think older guys are kind of cute and my friend said that they buy her presents, like jewelry and stuff. One even bought her the cutest bag and it's, like, really expensive. That doesn't sound so bad."
Larry grunted asking, "And did your friend say what she had do for those presents?"
"Well… mostly she said she just goes out with them and gets to look cute. She did have to do… something else for the bag, though," Caitlin said, her cheeks reddening as she bit her lip and looked at her lap, fidgeting.
"I thought so," Larry said, chuckling, "Guys who pay escorts usually have some kind of expectations that I'm not sure you'd be comfortable with."
"Do you think so?" Caitlin asked, sounding disappointed.
Larry nodded answering, "Yeah. I have guys that work for me who are really into that kind of thing. You hear stories."
He shrugged, refusing to elaborate.
"What kinds of things?" Caitlin asked.
Now, Larry blushed uncomfortably, saying "Things you probably don't want to do."
"My friend said she had to put the guys penis in her mouth. Twice," Caitlin said, quietly.
Larry choked again and the car swerved just a bit.
"Um, yeah, I guess… like those things," he said.
Caitlin was silent a few minutes as they drove.
"I did a profile on the site she uses," Caitlin said, almost whispering, "Just… just to see if I could, I don't know, to see if someone thought I was cute."
"You what?" Larry asked, astonished.
"I didn't publish it," she said, hastily, "I just made it. I don't know. I thought that maybe I could try it, you know, putting it in my mouth, with someone who wouldn't tell. That sounds stupid, doesn't it?"
"Caitlin, everyone experiments with that kind of thing. I'm sure you will, too. I just don't want to see someone sweet, like you, get hurt by some weirdo. If you want my advice, I wouldn't do it."
"Thanks, Larry," Caitlin said, and touched his leg again, briefly.
"You won't tell my dad, right? Or Trish?" she said, sounding worried.
"No. It's not my business to tell anyone anything about what you do with your private life."
"Thanks," she said.
***
The kid was put in bed shortly after 7:00, leaving Caitlin a full hour before Larry was expected home. For that hour, she masturbated with Trish's dildo while watching porno of older men gangbanging hot teens. She did so while wearing a pair of Trish's panties, which she carefully placed back in her drawer with a coating of her pussy juice in the crotch. When Larry arrived home, Caitlin was back on the living room couch, idly flipping channels on the TV.
Larry entered the living room to find the sitter with her legs tucked under her and her skirt riding a bit too high, showing off her legs. Slipping off his tie and coat with a sigh, he took a seat in an arm chair across from her.
"How did the night go? Any problems?"
"Smooth, as always," Caitlin said, "She's never a problem. When she gets a little fussy, you just put something in her mouth and she's as happy as can be."
The comment, naturally, made Larry think more about their earlier conversation as he looked at Caitlin's adorable little mouth. He shifted a bit in the chair.
"There's still some time before Trish is back, then I'll drive you home. Can I make you something to eat?" Larry asked.
Caitlin shook her head, "I had a little sandwich after I put her down. Thanks, though."
"Alright. I'm gonna head upstairs. Just text if you need anything," he said and rose to leave.
"Mr. Larry," Caitlin said, stopping him at the door.
He turned back.
"Could I…" she paused, blushed, swiveled on the couch toward him, resting her tits on the back, "I was wondering, about what we talked about in the car. You know lots of stuff about advertising, right?"
Larry shifted his feet and said, "I suppose so."
"Do you think… well, maybe you might just, you know, look at the page I made? I don't know that I'll really do it, but if I do I'd just like to know if you think it looks good. I trust you and I don't know who else to ask."
"Caitlin, I'm not sure that would be a good idea. I think you should just dismiss the idea entirely," he said.
Caitlin's face fell in her best look of adorable disappointment and she said, "Yeah. I guess you're right. I'm sorry," then she sunk back onto the couch and said, "I'm so stupid."
She threw in a small sniffle, barely audible, but enough that Larry heard it. He looked up the stairs, looked at the door, his better judgement telling him that he should not go sit and comfort the girl. The look on that cute little face, though, the disappointment and the small sniffle. It was just far too cute for someone with a cock to resist. He rounded the couch and sat next to her.
"Look," he said, "When Trish gets home I'll talk to her about a pay raise. You do a great job for us and you're always accommodating, even at the last minute. I know college is tough, but you don't have to resort to things like… like that to get extra money. Hell, I'll even recommend you to some of our friends if you want to take on more jobs."
"Yeah. I know you're right, Mr. Larry. I just don't think I can work in many extra jobs with school and all. I really like doing things for you, too. You and Trish. I'd hate to have a conflict."
"Thanks, Caitlin. You're awesome," he said, grinning, "You'll get rid of that escort page?"
She nodded, then added, "But I could still do the OnlyFans one. I wouldn't have to, like, meet anyone for that. Just take some more pictures."
"You did an OnlyFans page, too?" Larry asked.
"I didn't publish it. Just uploaded some pictures."
Before Larry knew what was happening, Caitlin swiped open her phone, tapped the browser, and handed it to Larry. Larry grimaced but didn't take the phone.
"Do you think that people would pay for them?" Caitlin asked, innocently, inching just a little closer.
"Caitlin, I shouldn't look at those," Larry protested.
"I trust you, Mr. Larry. I know you won't tell anyone, and I'd just like to have your opinion. It's okay if you don't think I'm pretty enough."
That cinched it and Caitlin could see his unwillingness fade away. He couldn't allow a pretty girl to start thinking that she wasn't pretty, especially not such a sweet girl like the angelic Caitlin. What kind of monster would he be? Caitlin could see a slight tremor in his hand as he took the phone from her, forever changing his perception of her.
He looked at the first image of Caitlin in a tight tank top, her cleavage spilling enticingly over the neckline. She was on her knees, the phone's camera having been perched on a tripod, and her panties were clearly visible. Caitlin inched closer, until her body was up against his side and she was looking at the photo with him. He flicked to the next one, showing Caitlin teasing the tank top up, exposing her tummy, looking away from the camera with a blush in her cheeks, biting her lip. She flicked her glance downward and saw Larry's cock twitch.
He flicked to the next photo and the tank top had risen, showing the hint of her lacy bra, her legs slightly spread, her cute face embarrassed. In the next photo, she'd removed the tank top but held it pressed over her tits and she was sitting back on her spread legs, baring her panty-covered pussy provocatively. Her little striptease continued in the next photo, where she'd dropped the tank top to the floor and put her hands behind her head, lifting her hair slightly, her eyes closed, head tilted slightly up.
The sexy bra pushed her ripe, teenage melons together invitingly, making them look even bigger. She could feel Larry's breathing getting shallower. The next image showed her toying with one of the cups of the bra, tugging it down just a bit to expose more of one breast, while her other hand lightly touched her pussy through the panties. Larry made no objection now, lingering on each image a second longer, burning the sight of her nubile, young body into his spank bank.
"Do you think they're cute, Mr. Larry?" Caitlin asked, her voice low, a little husky, betraying her own desire, making Larry think of that desire as he paired it with the image.
She reached down and flicked the next image for him as he answered, "Yes," in a breathy hiss.
The next photo showed her holding a fake cock, both of her small hands wrapped around its shaft. She could feel the heat of Larry's own arousal as he looked at the photo, imagining that it was his own cock with her hands around it. Likely, he was thinking about her owning a dildo, now, wondering just how innocent she really was, what she masturbated to.
A girl who owns a dildo doesn't have it just to look at it. She puts it in her cunt and she plays with it. She thinks about something, a fantasy, a scenario that excites her and turns her on, makes her pussy wet and ready to accept that big, fake cock. What was it that Caitlin thought about? He was, undoubtedly, wondering if he were part of that fantasy. He flicked to the next photo, in which she was looking into the camera with a look of aroused humiliation, the head of the toy in her mouth, one hand wrapped around its shaft, while the other touched her panties.
"I tried to put the whole thing in my mouth," she said softly, "like my friend did, but it's a really big cock and I couldn't get it all the way in."
Larry gulped audibly, unable to look away. He flicked to the next photo and gave a small groan. Caitlin was now on her knees, her ass facing the camera and her head resting on the floor, giving a perfect view of her panty-covered bottom. Larry, unable to resist a sexy bottom, was enrapt. Caitlin knew, then, that she had him. A hot ass was the man's kryptonite, and she knew it. He flicked to the next photo, showing her ass again. In this one, she'd peeled the panties partway down, keeping her pussy covered, but the globes of her ass were on full display.
"This is the last one," Caitlin said, "I didn't know if I should do any others, since I was just trying it out. Do you think they're cute enough, Mr. Larry?"
Still staring at the photo Larry nodded his head and said, "Um, yeah. You're… they're really, um, cute."
He made no move to hand the phone back. Caitlin slid her hand over his and slipped her other hand onto his shoulder, pressing herself just a little bit more into him. Her hand on his slipped over the knuckles, sensually, both of them now holding the device.
"Would you buy one from me, if it were real?" she asked.
"I… I shouldn't," he said, as though it were an offer rather than a question.
Her hand withdrew from his as he continued to stare at the picture, lost in whatever fantasy his hard cock was creating for him. His obvious erection tented the front of his pants and he made no move to hide it. Caitlin reached out and gently rubbed her hand over the head of his cock through his pants.
"Wow, Mr. Larry," she said into his ear, "You're really hard."
Larry shuddered, his breathing ragged as he groaned at the feel of her hand. She made a fist around his cockhead and gave it a small stroke.
"It feels really big," she whispered, "Your cock feels really big."
The hiss of her hot breath, the low, seductive tone filled with a hint of excitement and wonder as she squeezed his sensitive head sent a spasm of pleasure through him that Caitlin could feel in the hand on his shoulder. He made no move to stop her and she knew that he wouldn't, not now, as long as nothing happened to break the spell he was under, his cock was in total control.
"Do you… do you think I could try it, Mr. Larry? Do you think I could just try to put it in my mouth and see if I can do it?" she asked, circling his cock head with her fist and then jerking his dick a bit, giving it a nice up and down stroke.
"I…" Larry stammered, and Caitling deftly unzipped his trousers.
"I know that I can trust you Mr. Larry, and I know you wouldn't tell my dad. Could I just try it?" she pleaded cutely, her hand slipping into his fly and touching his naked cock.
Larry groaned again as her small hand wrapped around his hot length and squeezed it softly.
"It's really big, Mr. Larry," she whispered, "It's making me kinda wet thinking about it. It's okay, right? It's okay if I just try it one time?"
When he still didn't stop her, Caitlin knew that he wouldn't. He was too caught up in the feelings from his cock and the hot fantasy in his head, the view of her ass in front of him. She pulled his hard cock free of his pants and gave it another few strokes as she slid down from the couch and got on her knees. Her hand never left his cock as she got into position and looked up at him, placing his throbbing erection next to her angelic face. If there was any will left in him to stop it, that will evaporated when he looked down and saw her precious face with his fat, pulsing cock next to it.
It wasn't possible, now, to say no. He had to see what that innocent, pixie-like face and small mouth looked like with the girth of his cock spreading her lips lewdly around it. He had to know how much of his length she'd be able to take, how far into her mouth he could push it, and at what point she would gag. He had to see her saliva coating the shaft of it, to feel her tongue massaging his cockhead.
Caitlin put her lips over the tip of it and slowly teased them down over his crown, sealing her lips over the pulsing mushroom and giving his hole a flick with her tongue. Larry leaned back, conquered by the insistence of his cock. Caitlin took his hand and rested it on her head as she pulled her mouth from his cock.
"You can show me how to do it right," she said, his cockhead resting on her lip, "You can make me do it the way you like."
She quickly resumed suckling on his knob, caressing the sensitive head of his cock with her lips and then pushing another inch into her mouth, running her tongue across the underside. She never broke eye contact, her eyes wide, filled with wonder, a look of embarrassed disbelief at what she was doing on her face.
"Oh, God," Larry breathed and she felt his hand press slightly on the back of her head, urging her to continue.
Caitlin obliged, taking in another inch and then slowly, worshipfully, sucking, up and down, up and down, bathing his cock in her spit as her hands rested on his legs. Her slow pace, while delicious, was more of a tease, meant to get him riled up. It worked. His hand pressed harder and she allowed him to push her down, to force more of his length into her mouth as she continued to look up at him. Her lips stretched widely around the fat middle of his cock, where he held her for just a moment, before releasing the pressure on her head and allowing her up.
She pulled back, stroking the length of his veiny underside with her tongue and tickling the head with it, then he urged her down again, giving a slight growl. On her next upstroke, she pulled her mouth from his penis and stroked it wetly with her hand, saying, "It's so big, Mr. Larry. I like it, but it's so big. It feels really good when you make me do it with your hand."
At those words, Larry guided her mouth back over his cock and gave his hips a small buck, spearing her face with his cockmeat and making Caitlin glurk at the forceful intrusion. Her eyes teared up a little bit and the sight of them made him hold her in place and give her another thrust. She glurked again and felt his cock twitch pleasantly in her mouth. She gave him a slutty little moan of encouragement and he soon fell into a rhythm.
His other hand joined the first and then he was holding her head firmly in his grasp, slowly pumping his cock into her mouth as she stared up at him, wide-eyed and blushing. After only a few minutes of this, Larry took charge. He stood up, keeping the girl's mouth impaled on his cock, then set his feet and resumed fucking his prick into her more roughly.
"Gluk… gluk… gluk… gluk…" issued from her stuffed mouth as she flattened her palms on his legs.
Larry looked down on her cute little face, her lips so widely stretched around his penis and that doe-eyed look of humiliated arousal. He had to make her take it, now. Caitlin's pussy gushed as he fed the jerking length into her over and over, holding her head tightly as little rivulets of saliva drooled from the corners of her full mouth.
"I think…" Larry growled, "That I… have an idea… about how you can… make that extra money…"
Enjoy stories of slutty seduction? If you like it with a incest twist, you'll love Tempting Trevor, a story of sibling manipulation. This lengthy novella details the seduction of Trevor and his girlfriend Mary at the hands of his manipulative and twisted older sister, Stacy.
Care for a long form tale of sexy teen seduction of an older man? Look no further than Love, Lust, and Erin. This story follow's Erin's seduction of her best friend's father, along with Casey's pursuit of becoming a real slut.
Very hot. Hopefully this turns a bit darker and becomes more than a short story.