James slipped a finger into his mouth and suckled it on it slightly as he stroked his cock, eyes fixed on the picture of the cute emo girl on his phone screen. His arousal was building as he thought about all the possibilities that tomorrow held for him. This Vicki cutie seemed to show a lot of interest in him in their chats.
"lol I guess a lot of girls swipe left on me because I'm not big and burly or whatever"
"Hehe I don't mind a small boy :3 in fact I prefer soft feminine boys"
"Heh, well, I'm not THAT soft. I'm actually quite hard in a few places..."
"oooooo maybe if we're both lucky you'll get to see just how soft i can be :)"
He panted and lightly bit his bottom lip. "Fuck..."
Cum shot out from his cock and landed on his phone, perfectly obscuring the image of her face. More dribbled down his cock and over the tops of his fingers. Raising them up to his face, James licked and sucked the cum off, pulling his fingers out of his mouth with a satisfying pop. He giggled and picked up his phone, licking his cum off Vicki's image. James' face wrinkled slightly, as the taste was slightly incorrect, reminding him it had been a while since he'd cleaned his phone screen.
Locking his phone and tossing it aside, James laid down backwards on his bed. He really hoped he wouldn't spoil his chances with this girl, as she seemed to genuinely like him.
Rest didn't come easy as his weary body contrasted with his overactive mind, buzzing with the possibilities that tomorrow could bring him. By the time he next laid in this bed, he could have one of the cutest women he'd ever seen as his own girlfriend. Maybe their first date would go so well that the next time he was in this bed, she'd be in it with him!
And before he knew it, it was already 11:12 on Saturday morning. As James climbed out of bed, a corner of the blanket caught on his toe and was pulled out from under the mattress as he tripped and nearly face-planted. He tucked the blanket back under the mattress and sighed as he walked into the kitchen.
Once more, he was mildly annoyed, as he remembered that he'd eaten the last of his favorite cereal the previous morning, and then put the box back in the cupboard. Rectifying his mistake, he instead opted to fry some eggs. It was only natural that he'd break the yolk of one of the eggs after cracking them open. He liked scrambled eggs better anyway.
While eating his heart-healthy breakfast, James scrolled through his text conversation with Vicki from the previous evening. No, he hadn't had a psychotic break and hallucinated a pretty young woman that was interested in him. 6 PM that night at a nearby park. He looked at the clock on his microwave. 11:50. Only six hours away.
It had turned out that waiting six hours for something he was very excited for was not an easy task. James had run through his Twitter, Instagram, TikTok, and YouTube feeds at least three times each by now, and he'd only managed to kill three hours. Something must be done or he was going to lose it. After taking one more look at the five pictures of Vicki that he had (three from her profile, two she had sent him), he got up and decided to take action.
"Might as well start planning."
James poked through his dresser, and then his closet, pulling every piece of clothing that was neither dirty nor horribly ill-fitting and tossing them onto his bed. He studied the pile for several seconds. The question "what should I wear to impress this person?" has plagued the minds of nearly everyone to ever live, and there was still no 100% definitive timeless guide, a fact which annoyed James.
In the chats they'd had in the three days since the unknowable algorithm of a phone app had matched them together, James had learned that Vicki seemed to enjoy his feminine side quite a bit. She had mentioned frustration with guys who were always trying to act tougher than they were, and she'd even praised him for how he owned the fact that he wasn't super macho. On the other hand, it would probably be weird for a guy to show up to a first date wearing a skirt, fishnet stockings, and a crop top.
Casual and feminine, but not too casual or too feminine, he thought. A pair of black ripped skinny jeans to be supported by a studded belt, a tight-fitting band t-shirt, and a pair of canvas sneakers. He completed the look with a pentagram necklace and a little bit of eyeliner. James studied himself in his full-body mirror for a minute. Was he the kind of guy that a cute girl would date? As long as he wasn't being fake, he should be fine, he thought. This was basically a slightly tighter-fitting version of his everyday outfit from his high school days, so it wasn't like he was dressing up just to appeal to her sensibilities.
James gave himself a thumbs up and a smirk. He checked the time once more. 4:22 PM. Wow, he'd actually taken over an hour to pick out a very basic outfit. That seemed to happen to him a lot. Well, at least he could kill some more time putting his other clothes back.
A few more scrolls through social media, and it was 5:30 PM. James restrained himself from sprinting through his apartment complex and its parking lot to his car. The one thing that could really ruin tonight is if he got into a car accident. Or, as he soon realized, if he'd left his keys in his apartment. Upon returning to the front door of his apartment and discovering its locked state, he groaned in annoyance.
Pulling out his phone, he at once texted Vicki about this. James walked to the apartment's office, which was thankfully still open, and explained the situation to the man at the desk. When he left to go get the spare key, James checked his phone's notifications, finding a reply from her.
"O shit! I'm sorry. I haven't left yet so text me when you're leaving and I'll see you soon :3"
James sighed and pocketed his phone. After using the spare key to get back into his apartment, he snatched his keys and dashed back out the door.
Arriving at the park, his luck seemed to have turned around a bit as he got a great parking spot from someone who was just leaving. He walked into the park. Coming upon a clearing, he unmistakably spotted Vicki sitting on a bench. He waved at her and called out.
"Hey!" Vicki perked up and looked at him. A bright smile spread across her face as she jumped up to greet him.
"James! Good to meet you!" As the two shook hands, James noticed she seemed way more excited to see him than he was anticipating. Maybe he had nothing to worry about after all.
"And you, Vicki! I love your hair."
"Thanks! I like to dye it different colors every once in a while."
"I've thought about dyeing my hair, honestly, but I can't figure out what color I'd like."
Vicki tilted her head and giggled. "Hmm, I think dark blue would be a good color for you." She let out a quick burst of laughter. "Sorry, we just met and I'm telling you how to do your hair."