The First Date
With Matt’s encouragement, Maddy dispenses with several of her firsts.
Maddy was in a weird place. On the one hand, she had this tremendous theoretical knowledge about sex and kink, having done her research. And she was even gaining a bit of firsthand knowledge with flirting, direct messages, and video chats. She’d seen men naked, and men have seen her as well. She’d learned about what turned her on and what got her off. And on the other hand, she still hadn’t kissed a man in real life, ever.
She had a major infatuation with Matt. She found him incredibly attractive; he always embodied the perfect balance of dominance and care for her. But he was hundreds of miles away, and the probability of them meeting in real life was low. He never brought it up, and she didn’t want to be the one to do it.
“There are dozens of guys who would love to take you out. If you actually tune into the way men act around you, you will suddenly see them and you’re gonna wonder why you’ve never noticed them before,” Matt counseled her.
“It’s not just about whether they like me, though,” Maddy countered. “I don’t see myself being attracted to a lot of guys. And I’ve tried.” She told him about the way she analyzed men in her classes, trying to scrutinize whether or not she found them attractive.
“I just think that you’re missing out on some hands-on experience, baby. This is fun, what we’re doing together, but it could be even more fun with someone in person. Someone who can touch you, who can make you come while you just lie back and relax.”
That idea certainly sounded enticing, but simultaneously scary. What if it just wasn’t as good in real life as everything that Maddy had watched and fantasized about?
Matt encouraged her to go out, though, and she hated to disappoint him. She was on the lookout for a man who attracted her, who had the right kind of look, as well as the age at which she thought they’d be mature and appropriately dominant to teach her a thing or two. In Maddy’s mind, she planned out the entire course of this relationship and how she would lose her virginity so a facsimile of Matt.
She became super aware of those around her, gauging her interest in people she came in contact with. The one who caught her attention was Jared, a guy she’d seen around at the library before. Contrary to other people’s reasons for going to the library, Maddy enjoyed meeting people there. She had a quiet place to study in her dorm room, having no roommates, but at the library, there were people to watch and to engage with, and she felt more at ease starting conversations there.
Sitting opposite Jared at the table, she’d sneak glances at him, thinking about whether she could imagine kissing him or touching him. He looked to be in his thirties, his hair starting to thin in the widow’s peak pattern, but still largely there. It was dark, matching his thick eyebrows and his deep brown eyes behind his square-rimmed glasses. She noticed the books that he was pulling up, too — a lot of twentieth-century music history. She wondered whether he was a grad student in the music department.
He wasn’t. As she struck up a conversation with him in hushed voices across the table, she learned that he was doing research for a book he was writing. Outside of writing, he worked at a tire shop, despite his degree in English Literature.
Going out for coffee seemed like a natural next move, so she asked him. He agreed, seemingly surprised at her offer. This worried her, making her wonder whether she was wasting her time with her unrequited interest, but Jared seemed far more receptive to her attempts at flirting once they sat across the table from each other at the coffee shop. He was cockier, she thought, as if her attraction to him had given him an ego boost.
