The Dating Lesson

by Penny Wylder

  The Dating Lesson

  Penny Wylder

  Copyright © 2020 by Penny Wylder

  All rights reserved.

  No part of this book may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without written permission from the author, except for the use of brief quotations in a book review.

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  Contents

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Epilogue

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  1

  The text messages between me and Leo didn’t start out racy at first. They were like any other texts when you’re trying to get to know someone: what are your hobbies, what kind of music do you like, what’s your favorite food? The conversations didn’t stay innocent for long.

  The chemistry between us is undeniable. We have so much in common, and it was easy to send dozens of texts a day with stupid jokes or observations that we just knew the other would appreciate. And then I saw his pictures …. good lord. Thick, wavy, chestnut-colored hair, the kind of rich color women pay a fortune for in salons. Straight white teeth and a Colgate smile, and a body that made me do a doubletake, checking for signs that it was photoshopped. He’s got to spend hours a day in the gym to maintain a physique like that. Deep-set, smoldering green eyes lined with dark lashes. But his best feature, by far, is his perfect cock. After a playful back and forth of teasing, he sent me a picture. My jaw dropped to the floor when I clicked it open. He’s holding his hard cock in in his hand. It’s huge. His fingers can’t entirely encircle it. I stared at the picture hoping against hope that it would come to life. That I’d see him stroke himself, see his hands move over that perfectly long and hard cock, with its veins so clearly outlined and the crown swollen and darkened. I’d never seen a cock that magnificent before. A dream cock for any girl. The man is a mythical being, an Adonis, Hercules, King Triton—though not that old. He is older than me, though. He’s thirty-six and I’m twenty-one. But when we chat with each other, the age difference doesn’t really matter. I don’t think of him as an older man. I don’t think about his age at all. We’re just us, and we talk like we’ve known each other all our lives even though it’s only been a few weeks since we first spoke.

  We met on a dating site. I was just looking for a fun distraction. At most, I was looking for a regular fuck buddy. Someone to take the edge off. Stop me from having to hit the bar scene or wherever it is people find hook-ups. Nothing serious. I’m about to start my first year of law school, and I know I’m going to be working my ass off every spare minute I have outside of classes. And Leo is the perfect, uncomplicated distraction I need to totally disconnect from the stress in my life and just let loose, leave it all behind for a while. I think I’m the same for him, although we don’t really share that many personal details with each other. We definitely feel comfortable with each other sexually, there’s no denying the intensity of that connection, but we just haven’t wanted to bring the real world into our conversations. I have no idea where he lives, where he works; all I know is that he’s single. I needed to be sure of that single fact.

  I’m lying in bed in my dorm room, staring up at the ceiling while listening to a podcast on missing persons’ cases solved after decades using DNA sampling. I haven’t quite decided what I’ll do once I finish law school, whether I’ll join a non-profit legal clinic or become a public defender, but I do know I want to be the voice for the innocent and the wrongly accused. I’ve listened to so many stories about people who were convicted and sent to prison for decades, only to be freed later when DNA evidence cleared them. So many years of their lives lost because of shady or lazy investigations. Listening to these podcasts and seeing how many people were wrongly incarcerated before DNA evidence proved they were innocent, it motivates me through law school and toward a career in criminal defense. This is exactly what happened to my dad and brother. Last year they were accused of robbing a small check cashing business. The employee working at the time said a younger man in his twenties and an older man in his late forties held him up at gunpoint. He picked my brother out of a line up even though he stated both men had been wearing masks. Granted, my brother is no angel. He’s had brief scuffles with the law in the past. Before he turned eighteen, he had been caught shop lifting a few times and being out past curfew. If anything, he was a nuisance. That’s a far cry from an armed robber.

  My dad was his alibi. My dad had never gotten so much as a speeding ticket in his life. He was always a hard worker and a good husband and father. On the night of the robbery, he and my brother had been on their annual hunting trip. It’s something the whole family used to do together, but my mom and I stayed home this time because I had tests coming up and my mom had the flu. The only evidence they had against my dad was that he fit the age of one of the suspects and he was with my brother. There were no other witnesses to back up their alibi, no other evidence aside from the lineup.

  The charges were bullshit and the cops knew it. I’ve learned that police and prosecutors like closed cases, no matter the fallout for innocent people, real justice is just a bonus for them. My family couldn’t afford a hot shot lawyer, so we had to depend on a public defender whose caseload was a mile a deep and who barely looked up from his files when he first met my dad and brother. So my father and brother are sitting in jail for a crime they didn’t commit. Watching how it all played out for them, and imagining that there are so many families who go through similar circumstances as us, is why I studied so hard and applied to law school. I’ve decided to dedicate my career to preventing these situations from happening to other people. And of course, I’m not going to stop until I clear my dad and brother and have them released from jail.

  As I listen to the podcast, getting more and more angry about the stories and the injustice, my phone chirps, distracting me. I’ve given Leo his own ring tone that sounds like a bicycle bell chiming. Every time I hear it, my heart skips a beat. I look at my phone and it says I have an image waiting. Opening the image, I see it’s a picture of his dick, wet and glistening. He’s holding it in the shower. I can tell he has big hands. His long fingers are barely able to reach around the base. The sight of it instantly makes me wet.

  There’s another chime from Leo. The text says: Your turn.

  I smile.

  My bed in the dorm room is tiny. It might be even smaller than a twin. Just a step up from a toddler bed and uncomfortable as hell. I just moved into my dorm today and it doesn’t feel like home yet. It’s still pretty bare bones, with just my clothes hanging in the closet, my books and laptop piled up on the desk, and my sheets in a pile at the foot of the bed. I met my new roommate Brenna this morning. She seems nice enough, though I haven’t really had the chance to get to know her. She’s already diving into the campus party scene tonight, and I have the room to myself. We plan to have coffee tomorrow morning before our first classes start so we can try to connect. That’s hopeful, that she wants to get to know me. If we’re going to be living together for the next year, it’ll be nice if we’re friends, too.

  Since Brenna is gone, and I’m pretty sure she’ll be out for a while still, I strip down to nothing from the waist down. I spread my legs, exposing my freshly waxed pussy, and line my camera up for the picture. I’m wet as hell and it’s obvious in the image. I smirk, knowing he’s going to love seeing it.

  I take the picture and send it.

  Seconds later he texts again.

  Holy shit, I’ve never se
en a more perfect pussy. Send me a video. I want to see you play with that pretty clit.

  I set up my camera on my dresser. It’s hard to get the right angle, but I manage by stacking it on a couple of books and positioning myself just right on the edge of the bed. I hit the video record button..

  “Hey,” I say for the camera. “I’m sorry you can’t be here in person.” I drag my finger up and down the seam of my pussy, spreading the moisture over my clit, rubbing in slow circles until I feel it swell under my fingertip. “Do you see what you do to me? Your picture made me so wet.”

  My hips are tilting up to meet the pressure of my finger, and my toes are digging into the floor. The cheap dorm bed squeaks a little as I play with my clit, and I practically forget about the camera recording it all. I feel an orgasm start to build as I rub myself, but I don’t want my performance to end too soon, so I decide to bring in some reinforcements.

  I hit pause on the video and reach under my bed, dragging out my duffle bag. Inside is my vibrator. Please let it be charged, I pray to the gods of orgasm, and they smile down upon me when I hit the little button and it hums to life. I press record on my phone again and reposition myself. I start slowly, easing the tip of the vibrator inside my pussy just a little, and rub my clit slowly. I do this for about a minute but I stop, just before I start to come. I toss my vibrator to the side and grab my phone. I hit send on the video and wait. My pussy is begging for attention, but I want to see what he sends back first.

  The minutes tick by and still no response. I wonder if he’s watching it over and over. Almost ten minutes go by and I think maybe he didn’t get it. I frantically think to check my phone to make sure I sent it to him and not, heaven forbid, my mom, but just then I receive another text. From him. And this time it’s a video.

  I lay back on my bed and grab my vibrator before I open it. I have a feeling this is going to be good. The video shows him stroking his cock, breathing hard. It looks like he’s in his bed. I turn on my vibrator and focus it on my clit, watching his strong hands pumping his slick cock. I want to time this just right so I come when he comes. My toes are curling and every nerve ending in my body in tingling, feeling the vibration between my legs and watching his cock grow harder, bigger. I slip my vibrator inside myself and start pumping, imagining it’s him inside me. His hand moves faster, and I can tell he’s almost there. I’m not far behind. Suddenly he erupts with a groan, and cum spurts from his cock, landing on his tummy, the muscles rippling under his tanned skin.

  Just then I hear a key slide into the lock of my dorm door. I hurry and shut off the video and throw my blanket over myself. There’s no time to turn off the vibrator, so it continues to buzz between my legs as my roommate walks through the door.

  “Hey Kimmy,” she says.

  “Brenna,” I say. Normally a surprise like this would instantly turn me off and take me out of the mood, but vibrator between my legs is hovering ever so close to my clit, keeping me right there on a razor’s edge. It’s enough to keep my orgasm building, but not enough to send me over. I’m trying to act as casually as possible, but it’s not easy. “I thought you weren’t going to be here tonight,” I say.

  She raises her eyebrows and smiles. “Expecting someone special?”

  “Something like that.”

  Holy shit, I’m right there. My pussy tingles and pulses deep inside and I feel the orgasm rushing to the surface. If I come in front of her, she’s going to know exactly what’s happening. I won’t be able to hide it.

  “Well, don’t worry. I won’t cock block you. I just stopped by to grab some condoms. If you ever need any in a pinch, my top drawer is full of them.”

  “Thank you.”

  She grabs a handful and leaves. I grab the vibrator as soon as she leaves and plunge it deep inside my pussy. Seconds after the door clicks shut behind her, I come hard. I moan loud and long, my ass raising off my bed. With trembling hands, I turn off the vibrator and roll over, laughing into my pillow.

  After I stash away my vibrator, I pick up the phone and find several texts from Leo wondering where I disappeared to. I text him back and tell him the whole ridiculous story. We joke around for a while, and then text about other things. He tells me about a show he’s watching which leads to us exchanging stories about family vacations from our childhoods. Through all of these exchanges, I feel like I’m getting to know him better and better. It’s nice that he still likes to talk even after we both come. For most guys that seems to be their only goal. Once they get off, they’re done. He may be a stranger still, but more and more he feels like a real friend. A sexy friend. And the more I get to know him, the more I like him. I find myself thinking about him all the time even when we’re not texting. Eventually it’s time to say goodnight. He has to work early in the morning, and I have early classes. I want to be well rested and prepared for my first day of classes tomorrow.

  By the time I put my phone down and change into my pajamas, my eyes feel weighed down by weights. Luckily, after that amazing orgasm, I sleep like a baby.

  2

  The next morning, Brenna and I go out for coffee at the campus café. It’s six in the morning, an hour before our first classes. As we walk into the coffee shop, quite a few people look over at us. We do make an odd pair.

  This morning, Brenna is wearing a short black mini dress, fishnet stockings, and boots. Her hair is dyed black and red and she has piercings in her nose, lips, and eyebrows. Her appearance is a stark contrast compared to my own. I’m the all American girl next door type with my straight blond hair, jeans, tank top, and Vans. We don’t seem to have much in common, but if we are going to be living together, we’re going to have to find some common ground.

  “So, a lawyer, huh?” she says as she takes a bite of her poppy seed muffin. Even her coffee is as wild as she is with six shots of espresso and black as night compared to my vanilla latte with extra sweet cream.

  “That’s the plan anyway. I’ve been working my whole life to get good grades in school. Valedictorian of junior high, high school, and community college.”

  Brenna laughs. “They have a valedictorian for junior high and community college?”

  “Yep. I even got the presidential award.” Now it just sounds like I’m bragging, but I’m proud of my accomplishments.

  “What about your boyfriend or girlfriend—whatever your preference is—how did they feel about you being such a bookworm?”

  “Never really had time for relationships.”

  She raises a pierced eyebrow. “So you’re a prude?” she says jokingly.

  I can see why it looks that way. Clearly she didn’t realize I had a vibrator inside of me and was about to come while she stood in front of me last night. I’m far from a prude, and if she saw the videos and texts I was sending Leo last night, she would know. But I shrug and let her think what she wants. I don’t need piercings and fishnets to be wild.

  “What about you?” I ask. “Any significant other?”

  She gives me a coy smile. “I get around. I’m not looking for anything serious. I’ve got enough going on with my course work, and besides, these are my prime years. I’m just trying to have fun. There will be plenty of time to get serious later on.”

  We talk about school. I’m surprised to learn she’s a graduate student in biology, focusing on botany. But then she tells me her goal is to own a marijuana dispensary and natural apothecary one day, and it starts to make sense. She’s also taken a couple of classes in the law school, since her future the marijuana business is regulated so tightly, and she needs to have some understanding of the law. We talk a bit about professors and classes. We don’t have much else in common, and yet we get along. I don’t think we’ll ever hang out socially, but at least I don’t feel like we’ll have any conflicts or issues living together. She takes her schoolwork fairly seriously, I guess, and since she’s here on a scholarship, I know she at least had to have the grades and drive to earn that. And she’ll need to keep her grades up if she wants to
maintain the scholarship. As long as she doesn’t get in my way, I won’t get in hers.

  I look at my watch and realize there are only five minutes until my first class starts.

  “Oh my God,” I say, not realizing we’ve been sitting here for almost an hour. “I’m going to be late.”

  “Where’s your first class?” Brenna asks.

  “Greyson Building.”

  “You better run, then. That’s all the way on the other side of the campus.”

  “Shit!” I say, grabbing up my cup and making a quick dash to the door. “I’ll see you later,” I shout over my shoulder as I start hightailing it across the quad.

  People stare at me as I run across campus. I’m glad I chose to wear my Vans instead of dressing up a little and wearing the cute little kitten heels I considered this morning. I make it to the building and search through my bag for my schedule, trying to figure out which lecture hall my class is in. The building is massive! I dash up the stairs taking them two by two, and sprint down the hall until I see the large oak doors to the hall. I’m eight minutes late. I feel miserable. I hate being late for anything, and the first class? This is horrible.

  I take a deep breath, smooth down my hair, and walk in, hoping my late entrance can go unnoticed. But as soon as I walk through the door, everyone shifts in their seats and looks straight at me. I look around at all the people making eye contact with me and want to shrink into the background.

  “Good morning,” says a deep, powerful voice from the lectern at the front of the lecture hall. I look at the man and my heart cartwheels in my chest.

  No. It can’t be.