Simone

A tense silence fills the air as Gary and the contestants stare at Kat, waiting. After several minutes the hostess finally smiles and says, "The votes are in!" She pauses dramatically, "The winner of the first date night is...Simone."

Gary's cock twitches with a decade of anticipation. Simone, on the other hand looks from Kat to the man she doesn't even remember from high school with wide, watery eyes. "What do I have to do?" She whimpers.

With a wicked smile Kay tells the Arab beauty, "You'll have to serve your master, naturally." Then with a chuckle she continues, "You're going to give him a full body massage."

"Sorry." Garry mutters looking at the blushing girl, but unable to keep from ogling her full bust and toned legs in the slutty maid outfit.

Simone represses a sniffle and looks away from his gaze, looking to Ava who gives her a sympathetic look.

"Does Gary get a happy ending?" Cynthia giggles.

"Of course." Kat replies without hesitation. "If that's what he wants."

A heavy, awkward silence once again fills the room as everyone processes that. That silence breaks as Simone lets out a cry and takes off running to her room.

Unfazed, Kat looks at Gary and says, "Your date will begin at 6 and conclude whenever you would like. Until then you're all dismissed."

As Kat leaves them alone Cynthia murmurs, "It was just supposed to be a joke."

Ava rolls her eyes and shoots Gary a glare before wondering away.

Andrea puts a comforting hand on her boyfriend's shoulder. "What do you think I should do?" Gary asks her.

After a brief pause she says, "I don't know. Do whatever you think is right and I'll support you."

Hours later, as he's stripping down in the mansion's impressive spa Gary still isn't sure what he's going to do. He's been semi-erect all day at the thought of his high school crush being made to pleasure him, but he can't shake the horrified look on her pretty face from earlier either. Pushing aside his pondering he lays face down on the massage table and waits, his cock awkwardly rubbing against the cushioned table, a towel over his ass.

A few seconds later Kat leads Simone into the room. Simone's eyes are bloodshot from crying. Even so, she looks beautiful and the moment Gary lays eyes on her he knows the date isn't going to end until he cums. "The massage oil is right here," Kat tells Simone. "And remember, it's a full body massage. That means back and shoulders along with both sides of his thighs and legs."

"Both sides?" Simone sighs.

Kat nods. "And of course anything else he wants. Remember, you're here to serve him." Simone looks like she's about to break into sobs again but clenches her jaw and nods. "Good. Then I'll leave you to it."

Now alone there's an awkward silence between Gary and Simone. Just when Gary can't stand it and is about to say something he feels warm oil being poured on his back. "I've never given someone a massage before." Simone says apologetically, her hands tentatively touching his bare back.

"I'm sure you'll do fine." Gary reassures her as she starts to rub.

After another long, awkward pause she asks, "What classes did we have together?"

"A couple." Gary answers, enjoying her gradually more confident back rub. "Mr. Hamond's English class. PE senior year. A few others I think."

Simone giggles at that. "Do you remember when Mr. Hamond used to sneak whisky into his coffee when he thought no one was looking?"

Gary laughs, "Yeah. He always thought he was being sneaky with that little flask in his desk."

"I know, right. How did that guy not get fired?" She laughs.

"No idea." They both fall into laughter, much of the tension in the room dissipating.

As Simone works her way down to Gary's thighs she clears her throat and says, "I have something I need to tell you."

"Shoot." Gary moans, enjoying both the massage and the reminiscing.

"I'm a lesbian." Simone declares.

"Oh." Gary responds simply, the unexpected confession filling his mind with images of Simone having sex with other women. They both remain silent until she's finished rubbing the back of his legs and thighs. When Gary rolls over he lets the towel fall away revealing his now throbbing erection.

Simone steps back, looking at it in horror.

"Don't worry." Gary moans, taking his cock in his own hand. "I'm not going to make you do anything. Just stay there." Simone stares in horror as he begins to rub himself. "Have you ever had sex with another girl?" Gary moans, eyes locked on his lesbian crush.

"N-no." She stutters.

"What have you done?" Gary questions, hoping for a mental image that will aid him.

Simone blushes and nods. "I've never done more than a kiss...You're only the second person I've come out to."

"What did the girl you kissed look like?" Gary asks.

"Well...it was Ava." Simone confesses.

Gary laughs, his jerking speeding up as he imagines his ex kissing the beautiful lesbian. "Of course it was. Ava's a slut. Do you want to fuck Ava?"

Simone stares at Gary's masturbation in disgust but whispers. "Yes."

"Mmm. What about Cynthia?" He groans.

Simone grins a bit in spite of her obvious disgust. "Y-yes. She's very pretty."

"Do you want to eat her out?" His eyes lock on her dark, plump lips half imagining them on Cynthia's clit half imagining them wrapped around his cock.

She nods. "I want her to eat me out more though." Simone bites her lower lip, one hand subconsciously making its way to her inner thigh. "And maybe use a strap on."

"Fuck." Gary moans. "That would be hot. What else?"

"I want to play with her big tits. Squeeze them. Kiss them. Suck on them. And she could suck on mine, I bet she's rough. She could even bite them a little or-ACK!" Her fantasy is cut off as Gary erupts, his cum arching towards her, splattering her dress.

"God damn, Simone. You're a dirty girl." Gary pants.

"No." Simone whimpers with a pouty frown. "It's just fantasizing."

With a smile Gary says, "It doesn't have to be."

Simone's eyes go wide as she asks, "What do you mean?"

"I mean we can come make the most of your unfortunate situation. You want to have sex with the girls here. I want to watch you have sex with them. Of course you'll have to put up with seeing more of me masturbating and probably fucking the other girls too." Gary explains.

Simone's eyes water a little as she nervously chews her lower lip. "And you wouldn't do anything to me?"

Gary shakes his head. "Obviously I think you're gorgeous, but I'm not going to **** myself on you."

Simone closes her eyes and takes a deep breath then nods. "I'll do it."

"Good." Gary chimes. "Now come finish this massage."