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It was a scorching summer day in Gotham. Temperatures had soared and the wind made things feel hotter. Despite this, Jason still went to the cornerstone across the street from Tim’s safehouse to pick up some cold soda bottles and ice cream bars. If he was going to visit, he was not going to go empty handed.
The walk to Tim’s was only a block, but even in a t-shirt and jeans, Jason’s curly hair was sweaty. He wiped his forest with the back of his hand as he walked quickly; he didn't want the ice cream to melt before he got there. When he finally arrived, he went into the apartment lobby and breathed in the cold AC. Now shivering, he gave his name to the front desk before climbing into the elevator and getting to the right floor.
Jason didn't need to knock, Tim had given him his key a long time ago. Besides, he knew Tim’s schedule - he would be off of patrol today.
Entering the upscale apartment, Jason immediately went to the fridge first. He put the sodas in the fridge and the ice cream bars in the freezer - he didn’t want either of them to get warm. Then he turned and looked at the apartment. It was very clean today - books were on their shelves and cases were stacked neatly in manila folders on the living room coffee table. Still, there was no sign of Tim. However, there were only bedrooms and bathrooms behind doors in Tim’s apartment, so Jason wouldn’t have to look hard.
Jason walked up to Tim’s main bedroom. The door was closed, so Jason figured that Tim was there. Jason knocked once before turning the doorknob and opening the door. He was not expecting to see what he saw.
“Oh hey Jason.” Tim was laying on his stomach on his bed, legs in the air and ankles crossed. He had his airpods in but it was what he was wearing that had Jason pausing. Tim was wearing feminine pajamas, a camisole and shorts set to be precise. They were light pink and lacy with images of cartoon cherries on them. They appeared to be made of silk or another lightweight fabric and they hugged all of Tim’s curves beautifully, including his ass.
Tim sat up on his bed properly and it was clear from the bulging in the front of Tim’s shorts that he was going commando. Jason blushed and turned his gaze away. He asked, “”W-What the fuck are you wearing, Timbo?”
Tim grinned widely and moved to stand up, saying, “Isn't it cute? I saw Stephanie and Cass rocking a pair of cute pajamas in the Manor and I had to have my own. They feel amazing. The cherry print is super cute too, don't you think?” He stood in front of Jason, twirling around to show off the entire outfit.
Jason exclaimed, still embarrassed, “Why aren't you wearing underwear? I get that it's your safehouse and whatever, but I can see your entire dick through there!”
Tim laughed before telling him, “I like lounging without my underwear, it feels nice to feel free sometimes.” Jason continued staring, realizing that Tim had a pretty large sized dick under the shorts. He'd seen Tim naked before - the Batcave could be like a giant changing room sometimes - but he'd never looked at Tim in a sexual context. Yes, they were dating, but Jason had been a virgin and Tim had never brought up anything sexual. This was the first time Jason truly felt lustful.
Tim was picking up on Jason’s discomfort and arousal. He slowly licked his lower lip and asked, “Want to get down on your knees and suck it?” Jason’s cheeks were bright red - sure, he’d watched porn before but it was different from being propositioned in real life. Still, he was curious about how it felt to give head, so Jason swallowed his pride and got down on his knees. Tim looked surprised for just a moment that Jason had chosen to bottom.
Tim rolled down the waistband of his cherry shorts and his cock sprang free. Jason looked at it, mesmerized. It was long, pink and uncut - Jason licked his lips. Remembering how porn actors did it, Jason stuck his tongue out and experimentally licked the tip. Tim guided his cock to Jason’s mouth and Jason swallowed the tip. He tried to bob his head, but found it hard to take Tim’s cock without gagging. Tim let Jason experiment, staying patient as he tried to take more of his cock into his mouth.
Tim smiled down at Jason as he pulled his cock away, “You’re doing well Jay, but I don’t want to cum just yet. I want to pop your cherry properly.”
Jason asked softly, “Y-You know?”
Tim smiled cutely, saying, “That you’re still a virgin? Jay, hon, I know practically everything about you, including the type of porn you like. According to your searches, you like mating press sex…want me to fuck you into the bed like that, Jay?”
Jason’s lips let loose his desire, “Fuck yes, Timbo…I want you to rail me hard…”
Tim chuckled and motioned with his hands, “Onto the bed then. Take off those pants and your underwear.” Jason stood up and began removing his trousers and boxers. He blushed, realizing he was naked from the waist down in front of his boyfriend. Tim was gathering a bottle of lube from the bedside drawer as Jason got onto the bed and lay on his back, knees bent and spread open.
Tim settled between his legs and squirted a dollop of lube on his fingers. Jason hissed at the coldness as it touched his pucker. Tim stroked around Jason’s asshole until he relaxed, then plunged one of his fingers inside.
Jason grunted, “T-Tim…feels weird.”
Tim hummed as he moved his finger around, “I gotta open you up. Don’t want you to bleed during your first time.” Tim shallowly thrusted at first, soon going deeper and plunging rougher. Tim then added another finger and began spreading his fingers, scissoring him. As Tim felt around inside of him, he brushed up against the little bundle of nerves that made Jason moan. Tim smiled and stated, “Found your prostate; it’s going to feel amazing when we fuck.”
Soon, Tim was four fingers deep into Jason. Jason felt loose when Tim slid his fingers out. Tim rolled his cherry shorts down further and then started lubing himself up too. Jason watched carefully as Tim moaned and stroked himself to full length. Once Tim was lubed properly, he moved in between Jason’s legs and looped his hands under Jason’s knees, pressing them back towards his ears. Once he settled properly, Tim pressed his cock against Jason’s ass before pushing in.
Jason’s eyes widened and he let out a moan. He had never experienced something so hot and overwhelming. Tim moved out and thrusted in experimentally, causing Jason to throw his head back and gasp loudly.
Tim asked, “How does it feel, Jay? You feel heavenly to be inside of.”
Jason blushed more and looked at Tim with wet eyes, “It feels odd…but it feels good too.” Tim leaned in to kiss away any tears from Jason's eyes before they could form. Once Jason had time to adjust, Tim began moving and thrusting, angling his thrusts as to fuck Jason into the bed.
Jason moaned loudly as his boyfriend fucked him. Pressing against his prostate with each thrust, Tim made sure that Jason felt heavenly. Jason had been afraid of sex before, not understanding how people found it pleasurable - he understood now. He loved the way Tim felt inside of him, he loved how rough he was, and he LOVED being fucked into the bed.
Tim kissed him as he moved, saying, “Fuck Jay…you feel like a goddamn dream.” Tim pushed harder, causing Jason’s knees to be right by his ears as Tim mating pressed him. Jason came quickly with a shout, the pleasure overwhelming him. His body clenched around Tim’s cock, milking his orgasm out of him shortly after.
Tim lowered Jason's legs before pulling out. Warm cum dribbled out of Jason’s puffy hole. Jason caught his breath and watched as Tim got a towel to wipe him down with. Once Jason was mildly cleaner, Tim lay beside him. He wrapped his arms around Jason and kissed him.
Tim snuggled with him before admitting, “I think you were wonderful, Jay. I’m so happy I got to pop your cherry. Speaking of which, I could really go for something cherry flavored right now.”
Jason laughed breathlessly, telling him, “Lucky for you, I brought the cherry soda you really like from the corner store.” Tim smiled and laughed too - their bodies pressed against one another as they slowly began making out again.