Flynn and Ty looked up at the building in front of them.
"So she lives in an apartment, huh." Flynn said.
"Yep." Ty said.
"What ever she does, Assistant whatever of whateverology, must not pay very well." Flynn said. "I forgot the book on whateverology too."
Meanwhile, a confuse intern leaves the first book that came up when they searched "anthropology book" on the internet in Flynn's work mailbox, having no idea why he needed this.
"Tragic." Ty said. "So we just go in and knock?"
"That's what she said. Usually the girls are the ones doing the showing up, but it's nice to reverse gender roles every once and a while." Flynn said.
"Alright." Ty said.
They went up to the floor that Teddy was on and knocked.
"Hello Theodora!" Flynn said.
"Hello, Flynn! And, Ty, right?" Teddy said.
"Yep." Ty said, nodding with confidence, whatever that means.
"I don't we formally met, but I remember you hosting Shake It Up Chicago, sometimes they played it late at night here."
"Good to see my reach has gone far." Ty said.
Flynn interrupted Ty before he could embarrass himself further. "So Theodora, how have you been?"
"I've been good, and please, call me Teddy, Theodora is just for… more formal situations." Teddy said. "How have you two been."
"We've been great, company is booming and profits are rolling in." Flynn said. Ty nodded in agreement.
"Great." Teddy said. She sounded a little disappointed, as if money was an issue for her. And it probably was, Flynn thought. He kind of felt bad for her. But he was here to fix that problem, if she wished to. "What brings you here?" She asked, sounding a little cheerier.
"I have a proposal." Flynn said. He hesitated for a moment.
"A proposal, on what?" Teddy asked.
"I wish to have sex with you. I will pay you a large sum of money to make that wish come true." Flynn said.
Teddy took a few seconds to process it. "You want to have sex with me?"
"Yes." Flynn said.
"And pay me, like I'm a prostitute?" Teddy said.
"I'm thinking more like a one-time friends with monetary benefits type of thing." Flynn said.
"There's nothing wrong with prostitution." Ty added.
"I-" Teddy thought for a moment. "I don't think I'm worth it. I'm a virgin. I've only ever sucked a few cocks." Teddy said.
"That's not a problem to me." Flynn said.
"And it's a one-time thing?" Teddy asked.
"Yes." Flynn said.
"Okay, I'll do it." Teddy said.
Teddy couldn't believe she was about to basically sell her virginity to this famous man who basically showed up randomly at her door.
"Hey, what am I supposed to do?" Ty said.
"I don't know, guard the place?" Flynn said.
Teddy's bedroom showed her situation a little bit better. Everything was clean, it looked like a normal bedroom, but upon slightly closer inspection, it was cheap. Flynn turned his attention to the woman, who he was here for.
"You're very beautiful." Flynn said.
Teddy didn't know how to respond. She hadn't heard a compliment like that in a long time. But she didn't exactly go out much, she was trying to save as much money as possible, and she was always busy. She didn't have time for dating.
Flynn kissed her. And it felt amazing. It wasn't the romantic kiss she had long given up on, as Flynn's hands had wandered into her jeans, but it was amazing.
Flynn lifted her shirt up, and unhooked her bra. He had her completely naked before he had even taken a piece of clothing off. Teddy was a bit timid, of course, being a virgin, so she didn't really try to take Flynn's clothing off, and her being completely naked in front of a clothed Flynn only made her more timid.
Flynn, he did quickly strip, noticing the shyness of Teddy, and quickly realizing what it was that was making her shy.
Flynn would be taking control, he knew that much. He guided Teddy onto her bed, and spread her legs, his face right there.
Teddy had previously had boyfriends eat her out, but they weren't very into it. Flynn, on the other hand, was very much into it. She had thought that something might be wrong with her, when those boyfriends ate her out, but with Flynn, she realized that the guys were the issue, not her. Flynn had absolutely shattered her conception of oral sex, as he licked and sucked her, and made her feel things in places, things she had never felt, in places she didn't know could be felt. Her anxiety about the whole situation quickly disappeared as Flynn just kept licking and sucking her pussy. He didn't stop, like her boyfriends did in the past, he didn't complain. All of those issues she had with her body were starting to disappear. It wouldn't go all away, she knew that this was a one time thing, but it did make her feel good about her self in the moment and it would help her, slowly, but progress was progress.
And she came. And what a glorious orgasm it was, the greatest orgasm of her life. She did not know she could feel this good while she came. It felt so good, she nearly swore out loud, but she stopped herself and just moaned. Moaned like she never had before.
Now it was Teddy's turn to suck on Flynn's cock, she knew that much. Flynn was nice about it. He let her take her time. He let her just touch his cock for a bit. She wasn't entirely sure how big it was, she never asked her boyfriends how long their cocks were, and it had been a while since she had touched a cock so she wasn't entirely sure how Flynn's cock was measuring up compared to them.
She eventually took his hard cock into her mouth. She knew what to do. Suck. Was she good at it? Not really, not any more at least, it had been a while. But that didn't matter to Flynn, she was giving him pleasure, and that was enough for him. Like his previous payments, he hadn't expected anything amazing. He was enjoying himself though.
Teddy heard him moan and that was assured her that she was doing a good enough job. She kept sucking up and down on his cock. He kept moaning, and she kept getting more and more confidence in herself, her ability to give a blowjob.
Flynn didn't touch her head. He just watched her blow him. She didn't make much eye contact, but he didn't mind.
"I'm going to cum soon." He warned her. Well in advance, and, he actually warned her, unlike what he had done to other girls. Maybe something was different this time? Did he perhaps feel something more than lust?
"Are you going to cum in my mouth?" Teddy asked.
"Only if you want me to." Flynn said.
Teddy thought for a moment. "I do." She said before taking his cock back into her mouth and sucking on it until Flynn came.
Flynn came, and he hoped it wasn't too much for Teddy. It wasn't. Teddy's mouth was full, but it wasn't to much. She swallowed it. The taste, she could only describe as slightly salty.
"Is that it?" Teddy asked. "I mean, are we done?"
"If you want to be, yes, but I was hoping to fuck you." Flynn asked.
"Are you sure you want to fuck a virgin?" Teddy said.
"Yes." Flynn said. Maybe Teddy wasn't quite sure about why someone would want to fuck a virgin, but she didn't need to be, but Flynn was going to enjoy fucking a virgin.
"Do you want me on the bed then?" Teddy asked.
Flynn nodded and he helped Teddy into position. She was on her back with her legs spread, at the edge of her bed so Flynn could penetrate.
"You ready?" Flynn asked before he penetrated.
Teddy nodded and Flynn began to penetrate. Teddy bit her lip gently as Flynn's cock entered her and slowly went deeper. Flynn thought that was the sexiest look he had ever seen on a woman. He started thrusting slowly. Very slowly, allowing Teddy to feel the cock inside of her, and get used to the feeling. He started going a little faster, and Teddy began to moan.
They never broke eye contact. Not for a second, even thought Teddy wanted to look away. That would be too awkward. She enjoyed the feeling of Flynn inside of her. And she had finally lost her virginity, it felt good to have lost it, even thought she was being paid for it, she felt like it was very special. She felt, for some reason, that this was the right circumstances for losing her virginity.
They didn't fuck very hard. Flynn spent his time fucking her slowly. But they both enjoyed the fuck, very much. It lasted a long time.
Flynn blew his load inside of her, without warning. Sure, he was being nice before, but this was still Flynn. It surprised her, but she didn't say anything as Flynn flooded her.
And she didn't say anything at all that night, as they fucked into the early morning hours.
