Virgin Adventures (Patreon)

It was late. Too late at night for her to be awake. But there Stephanie was, laying upright in bed, her laptop open off to the side. Of course, it was a lewd affair that had kept her up well past her usual bedtime.

Stephanie pushed her glasses up her nose, gawking at the words on her screen. This was, without a doubt, the steamiest, most erotic fanfic she'd ever read. With each further word she read, the heavier her breathing became, and the wetter her panties got.

She continued, unblinkingly hypnotized in a trance of pure arousal, reading word after word until she could bear it no longer. Without breaking her reading pace, she slid a hand down the front of her waistband and used two fingers to explore her already-soaked cunt, expertly stroking her clit with her thumb at the same time. The poor sexually frustrated lass bit her lip as she fingered herself while reading sentence after sentence describing her favorite characters fucking each other senseless. She picked up the pace, flicking harder and harder at her clit and her fingers probing deeper and deeper to hit her g-spot. 

Soon her arousal was overcoming her, and she couldn't keep her concentration on the erotic literature that had brought her this far. She closed her eyes and lifted up her shirt to begin teasing her left nipple with her free hand. The extra bit of stimulation added to the overall symphony she was playing on her clit and g-spot. She could bear it no longer, and threw her face to the side, in an effort to muffle her screams in her pillow as she reached a full-body, thigh-shuddering, toe-curling orgasm. 

The pleasure continued for a long moment, then Stephanie went completely limp as she released all the tension. As her bodily functions returned to normal, she discovered the force with which she'd buried her face in the pillow was enough to have broken her glasses, right across the bridge.

"Oh, great..." She thought to herself, getting up to wash her hands and then find a roll of tape to fix them with. 

Great, now she had to walk around with taped-up glasses as if she didn't already look like a gigantic nerd.

Ironic, she thought to herself. She was a sex-obsessed smutfic addict who typically masturbated at least twice a day, yet she couldn't so much as make eye contact with a cute guy without turning beet red and losing the ability to speak. She was well-versed in all matters of nudity and lewdity from her time prowling the internet for titillating material, yet in reality, remained one of the most obvious virgins anyone had ever seen. Her real-life shyness and awkward behavior fed into a vicious cycle of sexual repression, leading to a private life of constant masturbation.

As she wrapped the tape around the bridge of her glasses, she made a vow to herself that tomorrow, that would end.

~

Your phone vibrated. You fumble for it in the dark. Who in the world would be sending you texts at this time of night?

You strain to look at the screen, the brightness burning your eyes that had adjusted to the dark. After a few blinks, you're finally able to read the message is from Stephanie. Confused, you open it. 

"Can I see you tomorrow?" is all it says.

This was weird. What did she want to see you out of the blue for? 

Still, despite her nerdy, gawky personality, she was actually really cute. You couldn't say no to that. And who knows, maybe it would lead to... something. Your heart jumped a little at the prospect of getting your hands on her slender, nerdy body.

Still, you thought it best to try and play it cool. You reply "Sure." 

"Great! 4 PM tomorrow at your place?" she texts back almost instantly.

"Sounds good." You confirm. She simply texts back a winky smiley face. That was weird too, she never used emoji. Texting with Stephanie was normally ridiculously dry and formal, like reading a Popular Mechanics article.

This whole thing was odd. Stephanie wasn't one to socialize, especially not out of the blue like this. You couldn't wait to see what this was all about.

~

Tomorrow comes, as does the agreed-upon time. At precisely 4 PM, a knock sounded on your door. Perfect punctuality, how like her. You go to open the door, giving your looks a quick once-over in the mirror in the hallway. Good as you ever looked, you decided, and pulled it open to find Stephanie, your dorky acquaintance herself, in the doorway. She was dressed in her unfashionable sweater vest and khakis. She perked up at the sight of you, but still unconfidently avoided eye contact.

"Hey!" She chirped, her voice breaking. She cleared her throat. "I mean, uh, hi, good to see you!." She corrected herself.

"Good to see you too, Stephanie..." You usher her inside. God, she didn't get one word out before making things awkward. It's a good thing she was cute.

She took her shoes off. "Can we... go up to your room?" She asked, almost wistfully. Awful eager, too. Could she really be here for what you'd hoped for...?

"Yeah! Sure, I'll lead the way!" You try not to sound too eager yourself.

You show her to your room and open it. Suddenly you feel a twinge of embarrassment at your nerdy paraphernalia that lined the shelves and walls of your room...but Stephanie was the last person who would be judging you for nerdy interests. 

She sat down on the bed, clearly even more nervous than before. "I... uh... Y'see..." She began, but turned bright red and was unable to actually say anything. 

"Hey, it's okay." You tried to reassure her. "Just say whatever you need to say."

She sighed and blurted it out.

"You're still a virgin, aren't you?"

You froze. So did she. The question hung in the air for far too long. 

"Uh... yes." You finally confirm after the uncomfortable tension became too much to bear.

"Well... so am I." She nodded, seemingly relieved that the conversation was going the way she expected.

"I was thinking that... perhaps... we could solve each other's problems."

You twitch. Stephanie was doing exactly what you had hoped for when she sent that text. Still, you had to confirm. 

"Uh... does that mean...?"

"Yes, it does." She smiled weakly.

"Do you want to start?" She asked, now apparently eager to get going.

"Y-yeah!" You nod, just as eager. Before she could change her mind, you tugged down your pants down, presenting your nerdy friend with everything you had to offer, already half-hard.

She gasped, reflexively, then stared at it through her thick, taped-up glasses. A look of something akin to disappointment crossed her face.

"Wh-what?" You ask, concerned. She stared for another moment.

"I was just, uh, expecting something bigger..." She muttered quietly, desperately avoiding eye contact.

Your heart sinks. Humiliated beyond that which you thought possible already, you motioned downward, beginning to pull your pants back up.

"Oh! N-no!" She interjects. "It's okay! We can still do it!"

She gets down on her knees. Desperate not to kill the mood any more she already had, she gripped your still semi-hard shaft in her short, feminine fingers. 

She held it gently, her virgin hand unsure of exactly what to do with it for a moment until she settled on simply tugging it as she'd seen in porn. 

"Even though it's small... I think I can still work with this..." She began, continuing her graceless handjob. "I mean, I suppose it was unrealistic for me to expect a massive penis like the ones described in my fanfictions..." She continued off on one of her big long nerd rants, but you quickly lost the ability to focus on what she was saying.

As she blabbered on and on, you found yourself fully stiff rather quickly, despite Stephanie's lack of handjob skills.

You bit your lip, already close; your meager virgin dick had so little stamina that even a half-hearted handy from an inexperienced nerd was enough to get you ready to blow. 

"You'll have to excuse me," Stephanie continued, "This is the first penis I have hands-on experience with, literally, and despite its meager size it's quite fascinating..." 

Probably owing to her nearsightedness, she leaned in closer to examine it as she continued to pump. You were too overwhelmed with both pleasure and humiliation to give a warning, however, and the unthinkable happened. 

Rope after rope of virgin beta male seed as a rush of both pure pleasure and sheer horror came over you, the sticky goop splattering directly over Stephanie's thick-framed glasses lenses. Finally, the sudden eruption proved to be the one thing that could interrupt Stephanie's infodump; she squeaked in surprise as the jizz splatted over her face and glasses.

"Oops... sorry..." She muttered meekly, taking her glasses off, frantically searching for something to clean them with. "Guess you were a little too eager, huh?" She laughed. "That's okay, we can try again in a bit."