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 sexdoll 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 guy's 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, Mr. 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 armchair 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.