"Late Night" with Hailee Steinfeld
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With Hailee Steinfeld
A TPG Short
CODES: 3rd POV, MF, handjob, blowjob, deep-throat
DISCLAIMER: Never happened, just a fantasy in my head
It's while working on the Jimmy Fallon show that you meet Hailee Steinfeld in the green room backstage, and she couldn't be lovelier. It's while surrounded by family and friends, that she openly flirts with you and even has two of her colleagues come over and ask you for your number, claiming that she finds you attractive and would love to keep in touch after the show.
You're naturally flattered by this, and explain that you have a girlfriend but this doesn't seem to dissuade them. In fact they really seem keen to set you up and don't seem to take no for an answer. Their behavior actually makes you wonder if they're being serious of just pulling your chain.
Meanwhile, you're then called away for a few minutes as the show gets underway, and return backstage to find Hailee standing around waiting for her big moment. You're immediately taken aback by her new outfit as she's wearing a sexy little black number, with matching heels.
"What do you think?" she asks you. "Too much?"
"Not at all." You assure her. "In fact you look amazing."
Hailee responds with a playful wink.
You're then doubly shocked when Hailee suddenly grabs you by the hand and asks you to show her where the nearest bathroom is, as she thinks she's going to be sick with anxiety. With just minutes to spare before she has to go on, you take her to the closest bathroom to catch her breath.
"Thanks babe," she tells you. "I owe you one."
There, Haiz goes on to claim that her stomach is doing summersaults as her entire family are sitting out in the audience and its making her ill with panic. Naturally, you try to calm her down but notice just how stressed she is, pacing back and forth.
"I need your help," she tells you. "This has happened to me before. I have to distract myself or, I'm going to throw up!"
"If there's anything I can do, just let me know."
But before I can barely finish the sentence, Hailee reaches down to grasp the large bulge in your pants, squeezing your cock firmly with her hand.
"Whoa, what the—"
"Please, you have to help me out. Just trust me okay?" she pleads. "I need this. I can't be sick in this dress, with this make up on."
You can't help but stammer nervously hoping that you don't get fired for messing around with the Late Night guest, but Steinfeld doesn't seem to care, and just glares into your soul with those big pleading eyes. You dare not stare back, knowing how alluring and tempting she is.
"Just help me out okay," she insists. "How do I look in this dress? Tell me what you really think?"
You assure her that she looks incredible, but as much as you want to help her out you can't afford to get caught fooling around with her as it could cost you your job. Despite your comments, Hailee quickly fishes out your hard cock and proceeds to jack you off in her hand – her eyes growing to the size of saucers as she admires your package.
"Mm, you're nice and big."
"Jesus Christ. This is crazy."
"Please. It's the only thing I can think of," she admits. "Please. It's helping me with my anxiety!"
At that precise moment someone knocks on the bathroom door looking for the actress, and you lie and tell them to check down the hall. This brief flirtation with danger only seems to encourage her, as she now spits on her hand and really goes to work on your tool – twisting and pumping it inside her fist.
It's at this point you decide to throw caution to the wind, since you figure if you're going to get fired for consorting with a guest you might as well make it worth your while, and you pull her in close and attempt to kiss her on the lips, only to feel her pull away.
"No, we can't. It'll ruin my makeup." she objects, while continuously jacking you off. "Not on the lips."
"What the fuck,"
Her refusal to kiss you only confuses and angers you, as you run your hands all over her ass and hips, down her legs and try to reach up under her skirt but the dress is designed in a way to prevent any access whatsoever. Hailee can't help but giggle at your persistence as you try again and again to slide your hand inside her dress, but are denied for your trouble.
"You really persistent huh," she teases. "You really want to get in there."
You ultimately focus your attention on her ass, where you rub and caress her derriere through the dress and make her purr.
"Mm, that's nice." she moans, while wiggling her butt for you.
Frustrated by her antics, you suddenly grab a handful of her long dark hair and cock her head back sharply.
"You know what, why don't you make my job easier and take off your panties."
"Yeah, you wish." she smirks back at you via the mirror. "Not happening."
"I'm serious."
"And why would I do that? I go on in a few minutes."
"cos if you don't, I'm going to rip a hole through this fucking dress and fuck you over this sink!"
Hailee reluctantly agrees, and peels her underwear down her legs as you snatch them from her feet and immediately inhale her musky scent. This seedy action makes her giggle, as the aroma of her cunt makes your cock twitch and leak pre-cum all over her fingers.
"Ah, you're so nasty." she coos while still jacking you off. "Don't you dare get any of that cum on me, do you understand?"
"Or what?" you growl back, as you grab her throat and lick the side of her neck.
"oh-god, you're not playing fair." she trembles, clearly excited by the rough foreplay.
Noting this, you now grope and fondle at her breasts through her dress, observing the way her nipples now poke obscenely through the fabric. Caught up in the moment, you push her forward over the sink and playfully tap the head of your bare cock against her butt.
"Give me one good reason why I don't rip this fucking dress off and pound you senseless."
Hailee responds by swinging around and kissing you hard on the lips – makeup be damned – breaking her own no-kiss rule and showing her tongue down your throat! You happily reciprocate and kiss her back, before she suddenly drops to her knees in front of you!
"Fuck it," she quips. "We have to be quick."
In an instant the Oscar nominated actress opens her mouth and engulfs your sword, smearing her bright red lipstick around the shaft of your cock.
You place your hand on the back of her head and now feed her your cock, marveling at the way she dutifully opens her throat and takes you all the way inside, pausing briefly to gag and cough as you brush the back of her throat.
"Good, good girl." you groan down at her, as her eyes suddenly flood and she weeps to the incursion.
"Ugh. You like that?" she teases up at you as you pull out of her sloppy mouth and smack the head against her tongue.
"So fucking sexy," you tell her. "You were born to suck cock Hailee. You're a born cock-sucker. "
Hailee responds to this praise by swivelling her head from side to side, sucking your cock like a lollipop while using her hand on your shaft at the same time. She pauses every so often to spit and slobber all over your junk, making sure to cover your dick in thick saliva.
"I hope you're happy," she mumbles between slurps. "You ruined my make up."
"I didn't ruin shit." You tell her. "Make me cum with your mouth or I'm going to rip this dress off you, and fuck you in the ass!"
The actress moans to the threat and picks up the pace of her sucking, really going to town on you. The animalistic groans alone make your nuts tighten up.
"Yeah? You wouldn't dare," she taunts while squeezing your balls with her fingers. "If you try to fuck me I'll scream. I swear."
"At this point I don't give a shit." You counter. "If you scream, I'll just make it worth my while and fuck you in the ass!"
"ugh-fuck." she groans back as she slurps at your cock with renewed energy, intent on making you pop.
Knowing how worked up she is you add, "Maybe if you're good, I'll let you clean me off after I FUCK your sweet little ass."
It only takes a mere minute before you suddenly and gloriously shoot your load into the back of her throat, gagging her.
While you're initial reaction is to pull back and fire rope after rope across her pretty face, Hailee instinctively grabs your ass to hold you in place, fixed tightly against her mug to ensure that you ejaculate straight into her belly and nowhere else.
...three and a half minutes later, you watch spellbound as the leggy starlet casually saunters out to the waiting audience with a smug expression on her face, the taste of your hot load still fresh in her mouth, like nothing out of the ordinary occurred.
Noting this you have to wonder just how many times she's down the same thing in the past?
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