Jersey City, June 2025
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Tyler
When Tyler (29) and Ann (27) agreed to see other people, he knew this was a possibility, maybe an inevitability. Dating could be a pretty ruthless marketplace, and of the two, Ann was significantly more marketable. It’s not that Tyler was unappealing — he had a good job and could be wickedly funny. Everyone loved Tyler. It was just that Ann was fucking hot — delicate features and a petite body with thighs that filled out her shorts almost impossibly well. And she had this flirty way of laughing at jokes that made men fucking swoon.
They’d been together long enough that Tyler didn’t feel threatened she’d leave and they had started young enough — in college — that he understood, even shared, her urge to see what was out there. They had a great sex life, he thought. She liked “playing submissive” for him — her words — but it had just been the two of them for seven years, and variety was the spice of life, right?
They created matching profiles on the dating app their poly friends recommended, cross-referencing one another and noting they were partnered but dating alone. Four days later, when Tyler was on his second match, he asked Ann how many she had.
“Wanna see?” She giggled as she handed him her phone.
She had 17. They all had one thing in common, he noticed with his first taste of alarm: Taller than him, more muscular, and quite a bit older.
“Huh. That’s a lot more than me. Anyone promising?”
“Oh, Ty—it’s different for guys. You knew it would be easier for me, right?”
“Yup. What’s his story?” Tyler pointed to the message at the top of her inbox from someone named Luke, who looked like he walked off the pages of fishing rod catalog. A little grey in the hair, face slightly weathered, profile said he was an ER doc, and he looked it — like nothing would rattle him.
“Luke. He’s sweet. Seems fun. He’s poly, too.”
“He looks a little, um, old, no?”
She frowned at him. “Is that how this is going to be, Ty?”
“No, I just — of course not. Sorry. What’s most important is we have fun, right?”
She touched his nose. “Exactly! Now show me your matches.”
Tyler felt nervous handing Ann his phone. She raised her eyebrow once as she looked at his two matches, both significantly less pretty than her, then smiled. “Adorbs. They look sweet.”
Ann
The truth was, Ann had been wanting to do this for some time. She knew she had it good with Tyler — like forever good. He had a good job and was basically the perfect bestie. They liked the same music, the same tv shows, he could cook, he made her laugh, they did the crossword together, and he was actually kind of fun in bed, in an adorable puppy dog sort of way.
The forever part, though, that was a bit scary, right? Ann and Tyler both liked to enjoy life and monogamy felt sort of like a waste — out of all the sex in the world, did she really only want to have the kind she had with Tyler?
She presented it to him as something for them, something all the hip couples were doing. Tyler was of course a good sport, even if he looked a little skeptical. Now that it was happening, she sure hoped he’d find someone soon. That would make things a lot easier.
Ann had settled on Luke pretty quickly. He seemed so refreshingly different than Tyler or the guys who followed her around the office. He just seemed so unapologetically himself, so open about what he wanted and expected. Like, she doubted she could manipulate him if she tried — he just gave off vibes that it was going to be his way or not at all.
They chatted for a day, she sent him the first nudes she’d sent anyone other than Tyler, and beamed when he told her she was a good girl. They talked about what Ann and Tyler had done — and what they had not done — and Luke said it sure sounded like she needed someone to teach her. To train her.
Ann said that she did, she’d wanted it for so long, but it was just impossible for her to imagine some of this with her boo Tyler.
Tyler
That night, when Ann was asleep, Tyler spent 40 minutes searching for Luke’s profile. When he found it, Tyler learned Luke was 48, 6’2”, and he had a list of kinks that made Tyler’s stomach clench. Tyler and Liz mostly played at kinks, but Luke seemed to take them a lot more seriously.
He listed them proudly, almost defiantly. “Collar and leash (leading),” “rimming (receiving),” “cock worship (receiving),” “humiliation (giving).” Tyler had a hard time imaging Ann being open to any of that, but then again, this afternoon he would have said she would never be interested in anyone as old as Luke.
Ann had her first date with Luke three days later. It was Thursday and Tyler was working a little late and she came into his office and kissed him on the ear while he finished coding.
“Thanks for being okay with this. It’s important for me. For us.”
She was standing behind him, gently rubbing the lobe of his ear.
“It’s Luke?”
“What’s the issue, Tyler?” Her voice had the slightest hint of annoyance.
“He’s just — he’s older than I expected.” He didn’t want to confess he’s found his profile so Tyler said nothing about his concerns about Luke’s kinks.
She pinched his ear, not hard but not lightly either.
“Didn’t know I needed to run my dates by you first.”
“Ann—you don’t. It’s just — sorry, you’re right.”
“Okay. You try to have fun tonight, too. There’s leftovers in the fridge.”
When Ann left, Tyler tried to focus on other things but he quickly ended up at Luke’s profile, staring at his list of kinks, torturing himself by wondering if his beautiful, sweet, lovable girlfriend was really into stuff like this.
Ann
When Ann got home three hours later, Tyler was waiting for her. She was glad because — almost unbelievably, given how she had spent the night — she was still horny.
He was sitting at the couch, and it seemed like he’d been there for hours. His little cowlick was sticking up, which Ann knew meant he had been running his fingers through his hair constantly.
He looked at her suspiciously, as if trying to see if he could notice anything different.
“Oh, Tyler.”
Ann sat next to him, resting her hand on his leg.
“Did you do anything fun?”
He looked away. “I read his profile. Ann. Are you sure he’s what you — it’s not what I envisioned for this.”
Ann didn’t like the sound of this. She had planned to break things to him slowly, in tiny bite-sized pieces.
“What did you do?” His voice was more emotional than she was used to. A touch of anger, accusatory.
Ann crawled onto his lap, straddling him. He wasn’t much bigger than she was. It was so different than with Luke but still nice. Ann started rocking back and forth gently.
“We had sex, boo,” Ann said, thinking that was the understatement of the year, as she played with his ear.
“Yeah, what did he get you to do?”
She stopped touching his ear and sat still.
“If you ask like that, I can just go to bed. I already orgasmed tonight.”
“I’m sorry. It’s just…”
Ann resumed rocking her hips and she put her finger against Tyler’s mouth, sliding it inside his mouth.
“Luke is going to be part of my life for a while. Part of your life too. We just have to take it slow.
She had unbuckled Tyler’s pants and taken his cock out.
“Get my hand wet, Ty. Good job.” She was purring as he sucked her fingers. “Nice and wet. I’m going to jerk you off…”
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