Jack had a crush on his babysitter when he was a kid. He was a tween in the ‘70s, old enough to be home alone but too young for his parents to truly trust him to be unsupervised. So they hired a babysitter every once in a while so they could have a weekend away to themselves. His name was Roy, and he was beautiful. He was 16 when Jack was 12, and Jack had never seen such a specimen of a human before. To Jack, Roy was the most attractive person he’d ever seen. Especially on nights when he’d leave Jack alone at home while their parents were away, ditching the kid for some disco under the agreement that neither of them would tell Jack’s parents. Fine with him. Until Roy would stumble back into the house in the early morning, exhausted from dancing for hours on end. Jack made sure he was awake watching TV or something when Roy got home. Because Roy would always have a few buttons of his shirt undone from the heat, and he’d be flushed from dancing, and a shiny layer of sweat would lay on his pale skin. Not to mention the way his pants accentuated his waist. Jack was just floored that anyone could look so good.
Now, as a fifty-something-year-old, Jack had nearly entirely forgotten about Roy. It was so long ago and the crush was so fleeting that he didn’t feel the need to really hold onto that information. Until one night, Trinity makes Dennis go with her and the girls to a disco night that one of their local clubs was putting on. And Jack hadn’t been able to see the kid’s outfit since he’d been working a double while Dennis had the day off. So when Dennis came crashing through Jack’s front door at 2 in the morning, Jack was waiting up after a post-work nap. He didn’t work the next day or night, and neither did Dennis, and he wanted to be up to make sure he could get to bed okay and he wasn’t too drunk.
But when Dennis strolled into the living room, Jack’s mouth went dry. Dennis looked like something out of his deepest fantasies. He was wearing a thin white button up that was halfway unbuttoned, displaying his pale, toned, sweaty chest. His hair was stuck to his forehead, and Jack can’t remember ever seeing it so curled. His face held a deep flush from exertion and alcohol. He had on boots with a 2 inch heel that were almost completely covered by a wide flare jean. Jack was certain that if he wrapped his hands around Dennis’s waist, his thumbs and fingers would touch. Good lord.
Dennis noticed Jack’s stunned look straight away, and sauntered towards him on the couch with a smirk. Jack swallowed what felt like a dozen cotton balls. Dennis bracketed his hands around Jack’s head against the back of the couch, leaning down so close their noses brushed.
He must have been screaming the songs at the top of his lungs for hours, because when he spoke, the hoarseness was unmistakable. “Hi, Daddy.” Fuck, it almost sounded like a purr. There was no way Jack could avoid getting hard at the sound of it. Dennis climbed into his lap, taking a seat right on Jack’s thighs. His hands came to rest on the nape of Jack’s neck, twisting the hair there between his fingers. “I missed you tonight.”
“Yeah, baby?” Thank god his brain finally turned back on.
“Yeah. You know how Robby showed me some old pictures of you the other day, from med school? I kept thinking about you, like that, dressed up like this, dancing with me.”
Now that made Jack huff out a laugh. “Disco was long gone by the time I was in med school, kid.”
Dennis pouted and sighed. “A girl can dream,” he said wistfully, before his focus lasered in on Jack’s flushed cheeks. “Do you like my outfit?” One of his hands left Jack’s neck to trail down the open V of his shirt.
“Of course, baby. You look incredible. So beautiful.” Dennis truly blushed at this, never failing to be flattered by the reverence in Jack’s voice. Jack’s brain finally flickered on enough for his hands to function, which were immediately drawn to Dennis’s waist. Fuck, he was right. Fucking tiny.
With Jack’s hands on him, Dennis could no longer resist kissing him. Which quickly turned into slow dry humping and groping like they were a couple horny teenagers. Which, after many indulgent minutes of this, Jack finally got Dennis to ditch his pants, but left the shirt on, now fully unbuttoned. Jack noticed that the kid was wearing the prettiest little lace thong, and he shuddered at the thought of him wearing something so lovely all night just because he knew Jack liked them. Those stayed on too. Then Dennis proceeded to ride Jack straight through the couch.
They woke some hours later after stumbling to the bed and promptly passing out after what was easily the best sex either of them had ever had. They made bleary eye contact and silently vowed it would not be the last time that outfit came out.