Teasing Ty Webb (Caddyshack) Would Include
Requested by anon!
You go to the country club with your boyfriend, Spaulding. Everyone keeps insisting you two are the cutest couple, but you honestly don't like your boyfriend very much, with him being so spoiled, entitled, and rude. But you've been dating him for a bit and he's alright for now
Spaulding's grandfather is a huge name at the club, so you get lots of perks. One of those perks is invitations to the VIP golfer parties
The first night you're there, you're wearing a sexy, form fitting black dress, showing no little amount of cleavage
That's when you see him: the rich, confident, talented man everybody kept talking about. The "best golfer" of them all. You're surprised he's not older, but he's not too young either. Late 30s, early 40s.
You approach him, and whisper in his ear while he's turned around. "You feel like grabbing someone a drink?"
He'd turn, popping an olive in his mouth. When he sees you, he'd almost choke on it. "W-who?" He swallows the olive. "For whom, may I ask?"
You smirk. "She's got a sweet black dress on that hugs her breasts perfectly."
"Really? I... wonder..." he murmurs, captivated by you. "Gimme a heads up, how close is she?"
"I'll give you a hint," you grin, "Warmer... warmer..." You take another step closer to him, so your lips are almost brushing his. "Hot."
"I'll say," he sighs, pulling at his seemingly steaming collar. You back off though, and smile mysteriously. You do still have a boyfriend, and if you're going to do this, you need to do it in private
"Come find me with the drink," you wink, sauntering away, "Make it a double."
A little later into the party, you're hanging out by a back wall, and you feel a hand around your mouth. You're pulled behind a curtain down a hallway, and pressed against a wall.
"Got you that drink," he whispers, holding it up. He's spilled most of it, but you just laugh, taking it and finishing the last little bit, licking your lips. He growls, and you drop the glass with a crash as he kisses you.
You two make out behind the curtain, and you reach down his waistband to feel his cock. His eyelids droop, and he moans against your lips, lifting his knee for you to grind against. That's when you hear a noise, and shove him off you just in time.
Your boyfriend's grandfather and about four other people from the party open the curtain.
"Hi!" Ty smiles brightly at everyone, urging you to play along, "My, this... this sure is a mess. We heard the glass fall... damn cat."
"Mhmm," you shake your head, kicking a few shards of glass.
"Ty, you and (y/n) got acquainted!" The judge smiles proudly. "My grandson picked a darling, didn't he? Innocent and shy. A blushing beauty!"
Ty gives a tight lipped smile, sticking his hands into his pockets to cover up his hard on. "Oh. Like a sweet virginal flower." You and Ty both laugh at the same time, and an awkward silence passes as everyone stares.
"Is that... red lipstick on your neck?" the judge asks, moving in closer to Ty. Ty steps away, still in complete control of the situation.
"Don't I wish! Ha, no. The cat scratched the shit out of me when I tried to tear him off (y/n). Probably gave me rabies. Best to stay away." The judge backs off in disgust, and you stifle your laughter.
Once everyone disperses again, Ty grabs your hand. "We can't leave it like this," he whispers.
"There's no 'it'," you mutter playfully, "We're not a thing."
"No, I mean IT will be very angry with me if we leave it like this," he gestures down to his erection, and you laugh again.
"Men have hands for a reason."
Over the next few days, you delight in distracting Ty on the golf course. You wear tiny, short skirts, so that when you bend over to pick up golf balls for Spaulding, you flash Ty your panties
Ty misses nearly every putt whenever you're around
"Be the ball, Danny... be the ball, Danny..." Ty tries to train his caddy, but gets lost looking at you fixing your boobs across the course, "Be the breast, Danny... squeeze my balls, Danny..."
Danny would look up. "Look Mr. Webb, I like you, but I've got a girlfriend who'd probably call me a golddigging whore."
Ty would snap out of it, and finally, he'd have to explain his predicament to his caddy. "Listen, there's this girl. But she's with that bastard's shitstain grandson."
"But you're the best golfer around. You’re a chick magnet!"
"Yeah, but she's making me work for it." He peers back over to you. "Which is why I want her so much." Danny would think about this.
"Well, try to reason with yourself. What would you do if you did get her?"
Ty would sigh, pretending to be pensive. "I don't know, Danny. I can't honestly say." He'd lick his lips, staring over at you. He'd pin you down to the bed, rip your clothes off with his teeth, and fuck you til you can't speak.
"That's descriptive," Danny would laugh.
"Did I say that... out loud?"
"Nah, but your eyes say it all, man."
That night, you’d visit Ty’s house, using the excuse he forgot a jacket, and you were returning it to him. As you two would be exchanging pleasantries, he’d just finally have enough, and grab you, lifting you up and taking you over to the jacuzzi. You’d both undress.
“Come in,” he’d grin, “It’s warm.”
“Oh, I’m coming,” you’d smirk, and get in, sliding right into his lap.
After making out, slow and lazy, for a good twenty minutes, you're ready for him to take you to the bed... but he makes a proposition.
"(y/n)... you ever heard of a sugar daddy?"
You grin.