Nice Guys Finish First 5

Jake was a nice guy. He really was. Not in that "nice guys finish last" kinda way. Not like a Reddit troll. Just an awkward, autistic 27-year-old who was still hopelessly virginal. Even after reaching out over text and asking a female friend if she'd mind helping him with his "problem" as politely as he could...she'd refused.

Ok, maybe he was a Nice Guy (™). But he wasn't about to admit it.

Going to university as an older student was hard enough when it came to making friends. Luckily, Jake was devoted to his field of study, and he found a circle of students who were equally passionate about marine biology. And yet...

...and yet, he couldn't take his perverted eyes off all the cute younger girls in his classes. Especially cute brunettes. Especially especially petite girls, so small and lightweight he was sure he could effortlessly bounce them on his long, skinny cock. Did girls find dicks like his attractive? He had no idea. Porn didn't give him much of a clue about real-life sex. He knew it must be messy, weird, uncomfortable. Just like everything else about human social interaction.

But it'd be worth it. Right?

It was a cloudy afternoon in April when Jake rushed through the halls of the science building, desperately trying to get to class on time. His sneakers slipped on the polished concrete floor and before he knew it, he was crashing towards the ground. He braced for impact-

"OhmygodJake!!"

-and found his skinny frame caught in small but surprisingly strong arms. The two students fell to the floor together, but the impact was considerably dampened, and Jake barely caught his breath before he looked up to discover his mysterious rescuer.

"A-Allison?" he gasped, recognizing one of his classmates.

The tiny brunette tucked a lock of hair behind one ear, blushing at the unexpected contact between the two of them. "I saw you falling, and-"

"Oh shit," Jake moaned, pulling away from her to scramble to his feet. "I was already late for class-now I gotta go check for bruises-"

"Class?" The girl tipped her head as she joined him in standing, confused. "You dork, Professor Brown isn't in today. There's no lecture on the schedule. Are you saying you didn't even read the syllabus...? We've known this since the beginning of the semester."

"Come on," whined the lanky boy. "I can't believe I drove out here for nothing." Being a commuter sucked sometimes.

"I was just leaving," Allison continued, looking down at her feet. Jake wasn't sure why. There was nothing particularly interesting down there. "I had a tutoring appointment, but now I'm free the rest of the afternoon. Do you...do you wanna come over?"

"Over?" His voice betrayed confusion.

"To my dorm room, dumbass," she said, looking boldly into his eyes. He'd never noticed her intoxicatingly blue-green irises before. It just wasn't the type of thing that caught his attention. She was cute and all, but not one of the main objects of his fantasies. Maybe after today, though...

"Why?" It was a fair question.

She sighed. "You said you had to check for bruises... Wouldn't you rather come stretch out on my bed than strip down in a public bathroom?"

His breath seemed to stick in his throat and his tongue went dry. "What?"

Why couldn't he get out polysyllabic responses to this girl's incredibly brazen advances?? Well, brazen by his standards, considering he'd never been propositioned. No woman had ever shown interest in him, beyond a distant friendly affection. This was completely out of left field.

"Just, come on." With an irritated huff, she grabbed his hand, not roughly but not indecisively, either, and began pulling him down the hall to the back door of the building. "My dorm is just across the path. Couldn't be closer."

Jake let himself be dragged along in a daze. He still wasn't sure what was happening. He knew Allison had said something about...a bed? Surely she just wanted to sit and talk. Or something. Maybe put some bandages on him. Yeah, she must be worried that his fall had led to the creation of a nasty new scrape on his gangly knees. Or maybe she thought he'd hit his head and needed to lie down. He felt as if he might be concussed, after all. Why else would such strange things be happening to him?

Outside, Allison didn't seem at all embarrassed to be seen with her awkward classmate. She waved and shouted "Hi!" to a friend, another girl who winked knowingly. Jake couldn't fathom what that wink could mean. Luckily, his new companion picked up on his oblivious nature right away.

"I have something of a reputation in my dorm," she laughed. "In other dorms, too. Like that time everyone in the second floor east wing heard me yelling 'Fuck me, daddy' to a guy I'd only met that afternoon... Yeah, that was a wild night. His roommate walked in and everything. Although that's not gonna happen today-I have a single."

Jake's brain spun round dizzily. He was naive, but not hopelessly so. He might just lose his virginity sooner than he thought. Although, considering he had thought he'd stay sexless forever..."Sooner" was a relative term.

A few minutes after leaving the science building, the girl had dragged him through the halls of her own residence, stopping at door 312 to fumble with her keys. Flinging the door open, she pushed him inside with a wide grin.

"What do you think of my humble abode?"

Jake didn't know what to say. There was a bed, all right. "Stupid," he thought. "Of course there's a bed. This is where she sleeps. And fucks. And...uh..." A set of truly massive fantasy dildos in all different colors decorated the top of the nightstand, along with a huge bottle of lube. If he'd been trying to speak, he would have choked in surprise at that moment. Luckily, he was still too dumbstruck by the whole situation to attempt conversation.

Allison wasn't about to settle for silence, though. "So Jake... About those bruises... Did you want me to check for you? After all, it's hard to see certain areas of your own body without any help." She gave him a sly wink and sat down on the bed, leaving plenty of room for her guest.

Nodding dumbly, the boy sat down on her plush comforter, a deep shade of purple which reminded him of royalty. This girl sure had expensive tastes. Those dildos must have cost a fortune. (Not that he knew anything about that, of course.) He would have liked to sit facing the window, but he thought that might be poor etiquette, so he sat cross-legged facing the head of the bed where she sat.

The girl looked him in the eyes, turning to place her slim hands on his shoulders and her slender feet in his lap. "Am I wrong, or are you new to seduction?" She giggled at her own choice of words. It was a habit of hers, he noticed.

Gulping, he nodded again.

"C'mon, speak up already," she pouted, reaching up to tug gently at his ears. His cheeks flushed red immediately; she'd found a sensitive spot. He suppressed a lewd moan. Guys were supposed to be quiet during sex until they came, right? Unless they were calling the girl "bitch" or "slut" or something nasty. He wasn't sure he could psych himself up to do any of that stuff. He wished he could close his eyes tightly, lay back and get it all over with.

"I need to know what you want. I pegged you as inexperienced the moment I met you, and I know this isn't easy, but you gotta use your words. So how about it? I like making cute little virgins fall apart. Do you want my hands on you? My mouth? Maybe you wanna jump straight to the main event and I need to get a condom?"

Jake finally steeled himself to open his mouth and say something, anything. "I-I... Oh, God." He buried his face in his hands, expecting her to keep talking, but she kept quiet. How would he get out of this? Not that he wanted to leave. No, he desperately wanted to stay. But he'd have to talk.

"I don't know what I want," he admitted. "Y-you can try...anything, I guess...unless I don't like it...and then, uh..."

"If you don't like something, you'll tell me to stop?" Her eyes were soft and a little concerned. "Oh, boy. You really are a mess. I bet you'll cum in two seconds once I start touching you. So fucking pent up." She laughed again, very softly, almost compassionately. "See, I told you, this is my favorite thing. Blowing boys' minds. And of course, their dicks."

His mouth finally unfroze from its scrunched-up shape and curved into a slight smile. "You-you wanna do that-to me? How come?"

She shrugged. "I don't know. I like you. I could tell you'd never been with anyone. Does that sound predatory? I'm younger than you, and you can always tell me to stop. I have an innocence fetish, is that so wrong?"

He shook his head. "I don't-I didn't think I was ever gonna get laid, and now there's...someone like you wanting to-uh-to fuck me."

Allison laughed delightedly. "Jake, I've never even heard you say that word! You're gonna have a dirty mouth when I'm done with you, m'kay?"

The boy's cheeks flushed tomato red. For a college student who was almost thirty, he was awfully cute, she thought to herself.

"Let's get started," she said in a slightly lower voice, reaching up to grab his jaw gently with both hands and plant a firm kiss on his lips, which were thin but pleasantly smooth and supple. "Mmm... relax into it. That's better. Do what I do." For a few minutes she did nothing but teach him how to kiss, eventually pressing her tongue into his mouth. He pulled away.

"I'm not sure I like that... the texture... it's..."

"Slimy," she finished. "That's okay, you might like it someday, but don't feel obligated." She pressed one last kiss to his mouth, lips closed but still relaxed and plush. "I was right, you are cute when you're flustered." His instant blush only proved her point.

"I think I'll strip," she said casually, glancing at her new lover out of the side of her eye. "Care to join me?"

"What?" He was distracted by her bra suddenly appearing from underneath her rapidly disappearing shirt, which slipped off her head to land on the floor below the bed. "Take my clothes off? Uhh... I guess... No one's ever..."

"You don't have to!" Allison interrupted. "If you're self-conscious. But you know, you'll need to at least pull your pants down. Plus whatever you've got on underneath. Remember, Jake, this is all about you. I get off on despoiling you, pleasuring you for the first time ever. I don't need anything from you except your desperation. That's what really turns me on." As if to demonstrate, she pulled down her leggings and her underwear came with it; there was a noticeable damp spot in her panties. Jake whimpered a little. It wasn't like he was familiar with pussy, but he knew it would feel damn good around his cock, which was finally starting to stiffen up with all this new and exciting stimulation.

"Hah, aren't you adorable. You'd better whine like that when I'm deep throating you. Lord knows you don't deserve my attention, hmm?" She was only teasing, but he felt a pang of insecurity, looking away from the enticing sight of a naked college undergrad. Allison noticed right away.

"Oh dear, I didn't mean that. I really do think you're cute. And yes, I'm probably only fucking you because of your inexperience, but that doesn't mean I'm not attracted to you. Don't look so down. How can I make it up to you?" She stroked her thumb over his cheek, across his lips, back to his ear lobe.

"I don't know," he mumbled, feeling like an idiot. She had just been joking. Why did he always have to take teasing so personally?

"Poor thing. I hate to admit it, but seeing you so embarrassed turns me on, too." His classmate kissed his forehead sweetly. "As long as you're okay with it, I want to see what's in these jeans."

How could he say no? He nodded mutely.

"Out loud," she warned.

"Uh... yeah... Um, you can see my dick. If you want..." He trailed off, feeling totally inadequate. The girl kissed him again, this time on the bridge of his nose between his eyes, and went to work on his belt buckle, deftly undoing it and opening his fly.

"Lay back," she said, somewhere between an order and a suggestion. That was what he needed, this firmness. It felt...right.

"Take control of me," he murmured, hardly realizing he was speaking aloud.

Allison gasped theatrically. "Jake! I would never have expected to hear such naughty words from you. Are you saying you're into femdom?" Her smile turned cruel for an instant and her anticipation of his response was palpable.

"I guess..." he mumbled. "I watch it sometimes... when regular stuff isn't, um, good enough..." He'd always felt guilty about this minor obsession. Why wasn't vanilla porn exciting enough for him to get off sometimes? He was such a freak.

"Oh, this is exciting news," she purred, her small hands pawing at his still-clothed chest. She scratched very gently down the length of his abdomen until she reached his unbuttoned jeans. "Lift your hips for me, baby."

He obliged, unsure why she needed this from him until she pulled firmly at his pants, his Spider-Man boxers sliding down as well. She stopped at his knees, leaving his legs restricted in their movement and his long, slender cock fully exposed. The horny student licked her lips, staring directly into Jake's eyes. He darted his gaze away, made uncomfortable by the eye contact.

"Shy? Or maybe you just don't like that," she mused, seeming to understand right away. "I didn't either, when I was younger. It makes sex better for me, but some people like to close their eyes. You can if you want."

He didn't want to miss anything, so he shook his head slightly and instead stared at Allison's naked tits. They were small, pert, with hard pink nipples. They kind of reminded him of the anime girls he often saw when browsing reddit for memes-those underage characters that he never allowed himself to jack off to. But Allison was at least eighteen, so this was fine, right?

What a weird train of thought to ride when a real-life hot girl might be about to ride him, he realized. She was straddling his hips, his cock hard and long against his belly, grazing the soft fabric of his t-shirt. Her neatly trimmed pubic hair was brushing his balls. "Fuck," he let out with his breath, biting his lip.

"That's it, naughty boy. You've had this coming to you for a long time."

And with that, her mouth descended on his cock. "Ngghh!" His hips jerked involuntarily upward and her lips sucked around his spongy head. She was licking at the slit, tasting his precum-he'd always been embarrassed about how much he leaked when he was jerking off alone in his room-making appreciative little sounds to show how much she liked the taste. And then her hands were on his hip bones, then she was propping herself up on her elbows, one hand curled around his balls, one grasping the base of his shaft where her mouth couldn't reach-she was stuffing as much of his cock into her mouth as she could fit-her tight throat was closing around his head as she gagged-it was all too much, and he felt his orgasm surging up from deep inside. Unable to form words, the pathetic boy simply gasped and moaned incoherently as his classmate sucked his soul right out of him, falling back onto the bed that wasn't his as he filled her hot mouth with his thick, bitter cum. She hummed sensually around him, milking every last drop from his tender balls, still cupped gently in one soft hand. Just before he reached the point of unpleasant overstimulation, she let go, allowing him to melt jelly-boned and exhausted into her bed.

"How was that?" She grinned knowingly.

"Gahh," Jake said, eyes tightly closed. He'd enjoyed watching this amazing girl suck his cock, but by the end the visual and physical stimulation were too much combined, and he had to shut out the world for a minute to recover.

"I figured." She got up, the bedsprings creaking, and came back momentarily with a box of tissues. "Not that there's much to clean up." Gently, she dabbed at the spit and flecks of cum which had escaped her deft lips, then tugged at the boy's jeans, dressing him again as if nothing had transpired between them and he was simply a little kid who needed help getting ready for the day. "You can stay here for a bit, if you like. Pull yourself back together while I masturbate. But now you're one of my conquests. Remember that when you see me in class on Friday." And with that she laid back, lazily grabbing one of the huge dildos on the nightstand and squeezing a hefty amount of lube onto her fingertips.

Jake could only lay there and listen to her obscene whimpers and shouts as she worked herself to climax. Once Allison had finished, she put on a bathrobe hanging by the bed and opened the door. "Go on, then. You can't sleep here. Against dorm rules."

"But-can't we do more-"

"Oh, aren't you cute! Didn't you listen to me earlier? I only fuck virgins, and then only when I'm in the mood for it. Why do you think I have such an extensive collection? I can manage just fine on my own, thanks. Now shoo."

With a firm slap on his right butt cheek, she waved him out the door, grinning lasciviously. As soon as Jake had left, she flopped back on the bed, this time intent on gaping her asshole with the biggest dragon dick in her collection.