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.”

“Oh, that’s fine.” She really did seem to be into him. His heart fluttered and he could feel himself blush. He guessed that the little giggle she let out a second later was a reaction to that, although it might’ve just been nervous energy.

The date proceeded fairly normally, with the two exploring the park and pointing out various spots that they’d been to before, or that they thought were neat. Their conversation drifted from talks of Vicki’s electrical engineering major to James’ job in data entry to Vicki’s urban exploration hobby and James’ geocaching experiences. It wasn’t super deep, but it was pleasant, and he enjoyed her company.

The two walked alongside a creek as the sun started to set. A cool breeze was starting to set in, which made James realize it might’ve been a good idea to bring some sort of light jacket. He stuffed his hands in his pockets. “Well, it’s starting to get dark…”

Vicki looked up at the sky and frowned. “Yeah, wow.” The sky was filled with beautiful oranges and purples, a gradient only broken up by the occasional cloud. “Shit, we’ve been going for a while, huh?”

“I think you’re cool.” Vicki looked back at him. “So I don’t really mind it going this long.”

She smiled at that. “Thanks, James. But, uh, I got a request.”

“What’s up?”

“Do you think you could walk me home? I’d rather not do that alone.”

James nodded. “No problem. I drove here, actually. Do you want me to drive you back home?”

She shrugged. “It’s up to you. It’s only a ten minute walk to my place. I’m just worried that you might not be able to get parking if you want to come inside. For coffee, you know.”

“Right, for coffee.” His heart fluttered at the implication. He knew this date had gone off super well, and now it seemed to be getting even better. “You make a fair point, but I think I’m more worried about my car getting towed if I leave it here overnight. I’m sure I’ll find some parking. We’re almost to the parking lot now anyway.”

“Cool, cool.” James felt Vicki wrap her arm around his. She looked up at him again and smiled. He pulled his hand out of his pocket and offered it to her. She accepted, and the two walked to James’ car while holding each other’s hand.

“How do you take your coffee?” Inside now, James sat down on a small sofa. He glanced up at Vicki in response to her question. He hoped that he could express himself smoothly here.

“Oh, uh, I don’t really- I mean, I don’t drink coffee. Um, very much. I prefer- do you have Hot chocolate? Or I’ll just drink water if you don’t have that.” Yes, very smooth indeed.

Vicki simply giggled. “Not a coffee boy, huh?” James heard a note of teasing in her speech. “That’s alright. I’ll get you some Hot chocolate while I make myself a nice mocha.”

As she got to work making their drinks, James watched her every move. At one point she got interrupted by a phone notification, which she swiftly responded to before returning to her work. When she did, she started slightly dancing to an unhearable beat and humming to herself.

James was hypnotized by her. Shit, he was really falling for this girl. She was nice, sweet, funny, pretty, and she really liked him enough to invite him into her home and very, very possibly get intimate with him after just one date. The idea excited him greatly. He tried to focus and keep his mind from exploring all the things that her hands might do to him, or the sounds she might make…

Eventually, he settled on zoning out and clearing his mind just to calm himself down.

“James.” He nearly jumped out of his skin. Vicki handed him a mug. “Your Hot chocolate.”

“Oh, yeah, sorry.” He grabbed the mug and took a long sip. “Shit, that’s good, Vicki, thank you.”

“Of course.” She sipped her coffee and sat down directly next to James, her leg brushing against his. James felt himself blushing again at this touch. He buried his face into the mug of Hot chocolate, hoping to conceal his embarrassing blush. Vicki’s signature low giggle told him that he’d failed in that goal. She brushed a bit of hair out of his face and got a close look into his eyes.

“You’re really cute, you know.”

James swallowed and set his mug down on a nearby table. Vicki followed suit. “That means a lot coming from you.”

“Oh? What do you mean by that?”

“I think you’re the prettiest girl I’ve ever met.” James focused on his breathing. He calmed himself and stared deep into Vicki’s gorgeous brown eyes. His whole body felt tingly. He leaned forward so he was mere inches from her face. “Can I kiss you?”

She smiled. “You know, I was just about to ask you the same question.”

Vicki took the initiative of closing the remaining three inch gap. Their lips met for a second the first time. Then for five seconds the next. The third time their lips met, Vicki grabbed the hair on the back of James’ head and shifted so that her legs were across his lap.

It was delicate and warm at first. Soft moans drifted from their lips in the moments when they weren’t perfectly sealed together. James couldn’t even tell who slid their tongue in first, but as soon as that started, the intensity ramped up. Soon, the two were full-on making out.

Vicki’s Free hand explored her own body at first, rubbing one of her nipples. Soon it drifted onto James’ body and worked its way down to the bottom of his shirt. She lifted it slowly. James moaned and leaned back, finally breaking the kiss, a string of saliva still connecting their lips for a short time after. He lifted his arms up as Vicki fully removed his shirt and tossed it to the floor nearby. She studied his physique for a moment before her eyes met his again. He was clearly forgetting something.

“Well? Aren’t you going to take mine off, too?” Her voice was soft and sweet, making James’ passions go wild. He bit his lip.

“Right, sorry.” She chuckled a little at that.

He lifted her shirt off and was wowed by her frame even more than she was at his. She planted a quick kiss on his lips. “You can take the bra off too.”

“Y-yeah, I got you.” He reached his hands behind her and undid her bra strap. He’d done it once or twice before, but he was still no expert and it took him a little bit to get it done. Once it was, he tossed her bra to the floor.

“Wow. Can I-“

“Yes!” Vicki’s voice was sultry and low. She stroked his hair gently and applied a bit of downward pressure to his head. James picked up on the signal and he brought his mouth to her left nipple and began to lick and suck on it. His hand traveled to her other breast and he began playing with it as well.

She moaned and tilted her head back. James was also enjoying playing with Vicki’s breasts. He could feel that he was already getting hard. She realized this too as her hands explored his body, ending up on his groin. His tight skinny jeans made hiding his erection impossible.

“Aww, you’re all nice and hard, huh?” She undid his belt with one hand before pulling it off. “Come on, let me see it.”

James leaned back into the sofa, kicking his shoes off and lifting his legs up as he pulled his pants off. While he was removing his socks, Vicki took off her own pants. “Hey, why don’t we take this into my room?”

She grabbed him by one hand and led him into her bedroom. With her pulling him forward, his momentum continued until he ended up face-down on her bed. James rolled over and laughed as Vicki climbed on top of him. The two kissed once again while she playfully pinned his arms down.

“Hey, Vicki.” The kiss was broken for a second, allowing James to slip in a request. “I’m in a good spot to eat your Pussy right now. I’d really like to.”

Vicki’s smile made him feel so warm. “God, you keep reading my mind and I’m going to think we’re psychically connected or something.” She climbed further on top of him, taking off her panties and straddling his face, pinning his head between her thighs.

Getting to work, James lapped at her Pussy in slow circles. Vicki produced a low moan. He looked up into her eyes. She seemed totally transfixed. As James sped up his licking, Vicki started moving her hips, grinding into his face. Her moans grew louder. She leaned forward even further onto his face. She reached into a drawer next to her bed, but James couldn’t see what she was doing as her body was in the way, and he was busy making her moan.

When she returned to her normal posture, there seemed to be a slightly different look in her eyes. She always seemed confident and bright, but now she eyed him with lust. It was so Hot to James that he redoubled his efforts. It didn’t take much longer for her to cum all over his face.

The bottom half of his face was now soaking wet, a fact he realized as she moved her Pussy off his face, exposing the wetness to the cold air. He licked his lips, tasting every drop of her juices that he could. Vicki had clearly had a great Orgasm, but she was nowhere near finished. She pulled James up and licked her remaining fluids off his face before kissing him again.

James felt her push his arms behind his back during their kiss. At first, he wondered why, but the reason soon became clear as he felt cold metal wrapping around his wrists. With a click, she had him in handcuffs.

Visibly confused by this, he let out a small nervous laugh. Her smile didn’t reassure him this time. It seemed more like she was playing with him.

“I don’t want you touching yourself for this next part, okay? And I don’t want you complaining either, so…” Vicki held her panties in front of James’ face. “Be a good boy and open your mouth.”

He complied. Pushing her panties into his mouth, Vicki smiled even more playfully. James had no idea he could be this turned on. He wiggled against his cuffs in an effort to reach his cock, but failed. The taste of Vicki’s panties was rather strong. She’d probably been wearing these all day.

Once she was satisfied with the panty gag, Vicki revealed the other item she got from her drawer: a roll of duct tape. She quickly tore off a piece and placed it over his lips, sealing her panties inside. James moaned and leaned back in surprise. She just laughed.

“That’s to make sure you don’t spit those out, bitch.” Her voice had by now taken on an entirely new tone. She was clearly aroused with the light bondage she was subjecting him to. James wondered if this was really the way to her heart. He’d only just been wondering how lucky he’d been to land a date like her a few hours earlier, and now he was handcuffed, gagged, and naked on her bed.

She traced a finger along the head of his stiff cock. He moaned and pressed his hips in the direction of the touch as much as he could, but it was so light that her finger simply drifted off his cock. This clearly amused her, as she kept doing it. The teasing got even more intense for James as she wrapped her whole hand around his cock and started stroking it very slowly, using her thumb to tease the head a little.

James whined into his gag, clearly very pent up and Horny. However, his desperation only seemed to amuse Vicki as she giggled at his whimpers. Then she stopped stroking and flicked his cock’s head a few times, making James recoil slightly.

Standing up, she rubbed her fingers on her Pussy before bringing them to her lips and sucking on them a bit. James was going crazy from arousal, and she was just enjoying every second of it.

“I’ll be right back, bitch. Don’t you go anywhere!” Her taunting made James feel even hornier. He mumbled in approval as best as he could and laid back down on the bed. He felt at least somewhat confident that she wouldn’t kill him. I mean, if she were some kind of serial killer, there would have been easier ways to do it than this, right?

After what felt like hours, Vicki re-entered the room, snapping on a pair of disposable latex gloves. Her phone beeped in her pocket. After checking it, she set it down on her dresser before approaching James.

“Now, I have a confession to make.” Her gloved hands started working on James’ cock, once again very slowly. Her right hand slowly stroked while her left teased his balls, occasionally working its way down to his Ass and giving it a few gentle pokes and swirling around the entrance. “I actually have a boyfriend already.”

“Mmm?” Vicki looked up at her captive and grinned. James’ heart sank as he tried to figure out what was going on. Was he actually in serious trouble after all?

“His name’s Charlie. He’s super cute and just an incredible guy.” Her stroking pace quickened for a few seconds, causing James to arch his back and moan in pleasure. “But we’ve always had this fantasy where the two of us take a cute boy like yourself prisoner and make him into our little bitch. So that’s what’s going to happen tonight.”

“Mmmm- mmmph!”

“Now, now, don’t worry. We won’t leave any permanent marks on you, alright? And I promise if you’re good, we’ll make sure you feel good. Does that sound okay? If it doesn’t, that’s too bad, because I’ve locked your clothes up, so unless you want to run home naked while handcuffed and gagged, you’ll just have to be a good bitch.”