The Dating Lesson

by Penny Wylder

  Sunday night, before I fall asleep, I see an email from the administration sent to all of the students. Classes are canceled on Monday. I’m not sure why. Yet another day I won’t see Leo and it has me feeling sadder than I anticipated.

  I’m lying in bed Monday, trying to think of something to keep me busy this morning, while Brenna is finishing getting ready for the part time job she picked up recently.

  There’s a knock at the door. I assume it’s another one of Brenna’s friends. “Are you gonna get that?” Brenna asks when I don’t get up. She typically answers the door when she’s expecting someone, so I’m confused.

  “Are you waiting for someone?” I ask.

  She fluffs her hair in the mirror and applies a thin layer of lipstick that seems far too bright for this time of morning. “Nope, you?”

  “No,” I say. Maybe someone in the dorm has been locked out of their room and needs to use the phone. It doesn’t happen often but there are times when we get the random knock on the door by other dorm neighbors, telling us about a party or asking to borrow something.

  When I open the door, I nearly trip over my feet when I see Leo standing there. He’s not wearing his typical professor attire with the khakis, tweed jacket, and oxford style shoes. Instead, he wears jeans, Chucks, and a button up plaid shirt. He looks casual, yet cool and sexy as hell.

  I stand at the threshold like an idiot, ogling and marveling at him. When Brenna comes up behind me, I startle.

  “Professor Whitford,” she says, confused. She also seems to notice the casual way he’s dressed and is perplexed by it. “I thought classes were cancelled today, at least that’s what the email said,” she says. There’s a hint of fear in her voice. Which is strange because all she seems to care about is sex and partying, yet to get into this school and stay here, you have to maintain excellent grades. Maybe she’s one of the lucky few who just aces school and doesn’t have to work as hard as the rest of us.

  Leo smiles casually. It’s a friendly smile that seems to catch her off guard. I know they have a turbulent history and she was kicked out of his class, but there doesn’t seem to be any bad blood between them.

  “There aren’t any classes today, but I am here on official business. Ms. Stevens,” he says to me. “I know you’re trying your best, but there are some things we need to discuss about the last paper you turned in,” he says to me.

  Considering we haven’t turned in any papers recently, I know he’s full of shit. I have to stop myself from smiling. Brenna looks at him, then at me. She gives me an odd look. I can tell she has questions and the look she gives me hints that she will ask me about this later.

  Brenna shrugs and leaves for her job. I invite Leo in, glad that I had cleaned my half of the room the day before. He locks the door behind him and rushes over to kiss me. We tumble back on my little twin-sized bed and make out until my lips are raw and my skin is chafed by the slight stubble on his chin.

  “Come see a movie with me,” he says.

  I lean away from him in surprise. This is definitely not where I saw this going. “Like a date?” I ask. Then I feel presumptuous and wish I can take the word back.

  He shrugs. “That’s usually what people call it, I guess.”

  “Oh really?” I say teasingly. “Is that not what you call it?”

  He rolls on top of me, pinning me against the bed. I can feel his hard cock pressing against me. “Go on a date with me, Kimmy.” He looks deep into my eyes. I feel like I’m looking into the universe and if I look away for even one second I will lose him and float away. I get lost staring into his eyes. “I want to go on a date with you,” he says. “Yes, I want you all to myself. No rushed meetings. No interruptions. I’m not seeing anyone else, and I expect the same from you. I want more between us. Does that answer any of the questions you might have?”

  My heart thrashes against my chest. I nod.

  “Good. Let’s get going already. The movie will start soon.”

  We go to the movie, a romantic comedy I’ve been dying to see but haven’t allowed myself to take the time to do it. We get a bucket of popcorn, ridiculously large sodas and sour candies. Leo holds my hand and scoots close to me. Occasionally he kisses the side of my head. The tension builds between the characters, but I’m barely paying attention as Leo strokes my bare leg with the tips of his fingers. His eyes are on the screen, and he feigns innocence the few times I tell him to cut it out. But he doesn’t stop, and eventually his hand is sliding up my inner thigh, fingertips gently caressing the soft skin there. I turn around to make sure nobody can see, but the few people who are in the theater are scattered away from us and they’re all paying attention to the screen. I breathe slow and methodically, trying to control the urge to climb up onto his lap and mount him like a champion bull rider.

  His hand continues to crawl up my skirt until his fingers are just at the edge of my silky panties, tracing the line between satin and skin every so lightly and teasingly. A few times I wiggle, urging his fingers to dip inside my panties, but I see that devilish smirk appear on his face and I realize that Leo will take all the time he wants playing his little game. Finally his finger snakes under the fabric, and he drags his finger up and down my already dripping pussy. I look in back of me again and decide nobody will be bothered if I prop my foot up on the seat in front of me. Once my foot is up, he has plenty of room to explore. His fingers are long and thick. He puts two fingers inside me and pushes all the way in, so far that I feel his fingertip brushing my g-spot. I inhale sharply at the sudden sensation, and sit up a little straighter, unable to control my body’s movements as long as he keeps stroking me like that. I bite my lip to keep from making noise as his thick fingers continue to fuck me. His eyes are on the screen the entire time, and just a hint of a smile betrays that he’s actually not paying attention to the screen at all.

  Suddenly, he pulls his fingers out of me and drops our box of candies to the floor. Before I can even understand what he’s doing, he’s on the floor and pulling my panties aside and lapping at my clit. His tongue works its voodoo magic across my slippery and swollen clit, and it practically sends me into convulsions. My knees shake like mad. My hands are gripping the arm rests. The tight circles he’s drawing with his tongue over my clit are the exact right rhythm that will have me coming in seconds, and I grab onto his head to make sure he doesn’t move his head, not an inch. My ass is raising out of the seat a little, and I grind into his face, coming closer and closer to the orgasm that’s just in sight. I’m too turned on to think about the mess I may be leaving on the seat’s upholstery. Then Leo’s fingers dip into my pussy again and stars burst behind my eyes. His free hand flies up and clamps over my mouth before my moan escapes my lips. But I come long and hard, and a woman a few rows in front of us looks back at me with an annoyed scowl on her face. Luckily for me she can’t see Leo on the floor in front of me on his knees.

  The last shock waves of the orgasm leave my body, and I scan the theater again before tapping Leo’s shoulder, giving him the all clear that it’s safe to come up back to his seat. He leans over and gives me deep kiss on the lips, and I taste myself on his lips.

  I watch the rest of the movie in a blissed-out daze, resting my head on his shoulder and holding his hand.

  After the movie we go to dinner. He takes me to his favorite sushi restaurant; another thing I haven’t done in ages. Usually I grab whatever I can from the cafeteria and eat while I read or study. It’s a quaint and quiet spot, tucked into a little nook of a strip mall. The food is to die for, the best sushi I’ve ever had. I’m nervous at first because he’s so affectionate with me. Not only do I not know how to take that, considering this was only supposed to be a fling, but also because he’s my professor and he doesn’t seem at all concerned about people seeing us together.

  Even though the thought of getting caught and there being some sort of scandal is horrifying, I love the idea of us dating; being a couple. He’s everything I could ever want in a boyfriend. I k
now, after meeting him, no one will ever be good enough for me. I’ll compare every other man to him in the future and no one will ever measure up. He’s ruining me for anyone else. Leo is the whole package. I just wish we didn’t have this complication to deal with. I understand why the school has a policy against professors and students dating. I’ve heard horror stories over the years of professors who take advantage of their status to coerce students to date them, but in this circumstance, we’re both adults. This isn’t high school. No one is taking advantage of the situation. I don’t need special treatment in order to get good grades. There’s no reason a relationship between us couldn’t work. Unfortunately, not everyone would see it that way.

  As we sit here having dinner and I learn more about him, the idea becomes ever more appealing. I learn that, like me, he always wanted to be a lawyer. But for him, life got in the way. His mother had got sick and he chose to take care of her once he graduated from law school. He took a job teaching at the law school rather than taking months to study for the bar, and once she got better, he didn’t really have the desire to be a lawyer anymore. He enjoyed teaching and interacting with the students. He likes the freedom the academic calendar gives him so he can pursue his other hobbies and travel. He hasn’t ruled out ever becoming a lawyer, but for now, he really loves what he does.

  “So why do you want to be a lawyer? Were your parents in law?” he asks. The waitress brings us a tiny carafe of sake. The warm alcohol relaxes me, taking away any nervous thoughts I may have had about getting caught in public with him. I’m able to settle in and enjoy our time together getting to know each other. I find myself being completely comfortable opening up to him. I tell him things I don’t tell anyone.

  “The opposite, actually. My dad and brother are in jail. They’re innocent, and they could’ve received a fair trial and justice if we’d been able to afford a decent lawyer. But my family’s poor, and the legal system is stacked against poor folks. I plan to work in public defense or for a free legal clinic that helps low-income families who deserve a fair chance.”

  He touches my hands across the table. The lamp above our heads picks up flecks of red and silver in his hair. He’s truly the most beautiful man I’ve ever seen.

  “I’m very impressed by you,” he says, weaving our fingers together. “You’re all action. Most people who go through hardship do a lot of talking about how they will make things better, but they never have a plan to actually execute it. You’re dedicated and smart. You’ll be an amazing lawyer. I have all the confidence in you.”

  My heart flutters as he leans forward and kisses me. “Why don’t we go back to my place?” he says with a suggestive smile.

  I grab my coat off the back of my chair. He doesn’t have to ask me twice. “Let’s go,” I say eagerly.

  We get back to his house. It’s a modest track home in a great neighborhood. Far nicer than anywhere I’ve ever lived. It’s a cozy two-story with a fireplace and big yard. The whole living area has been converted into a library, all the walls covered in books. Instead of a typical living room with a couch and chairs and TV, there is a comfortable-looking nook with a bench covered in pillows and a lamp with soft yellow light for reading. I imagine this would be exactly the kind of décor I would have in my own place if I had one, which makes me feel all the more at home here with him.

  “I like to do little DIY projects,” he says, pointing to all the little details that I just start to notice. I realize the shelves are made out of metal pipes, and the lamp shades are the covers of old books that have fallen apart and he’s sewn together.

  “This is amazing! You’re incredible.”

  He takes me in his arms and holds me close to him. I can feel that he already wants me.

  I let out a slow breath. “So are you,” he tells me and kisses me deep.

  He lights the fire. It casts a warm glow over the room, warming my skin. He lights candles and turns on fairy lights that wrap around the beams of the ceiling. It’s all so romantic and wonderful. He piles woven blankets and furry throw pillows onto the floor and guides me over to them.

  He slowly peels off my shirt and lets it fall to the floor. My bra is next. He holds my naked breasts in his hands, caressing and kissing, and sucking at my hard nipples. I roll my head back and close my eyes as his tongue and teeth work on that sensitive area. My pussy aches with every flick of his tongue. There seems to be a direct line connecting my nipples and clit because every time he sucks or bites on my nipples, I feel a twinge between my legs—a crisp shock of electricity that seems to ignite my whole body. I’m wet and I want him so badly, but I’m in no hurry. I don’t want to rush this, so I let him take his time and I just enjoy the sensation.

  He lays me on one of the soft faux fur blankets on the floor and pulls off my skirt and panties, leaving me naked and exposed.

  “You’re so beautiful,” he says, lying beside me. His eyes roam over my pale skin, taking in every freckle, every detail that is tailored specifically to my body. The way his eyes light up when looking at me allows me to relax. He’s the first person I’ve ever allowed myself to be fully comfortable around without clothes on. I’ve always been self-conscious. My butt has always been a little on the bigger side. And though men seem to like it, girls in middle school and high school always made fun of me. All of the insults made me horribly self-conscious growing up. I made sure to always wear baggy clothes, and when I would go to the pool or lake, I would always wear a cover-up. As I got older, I didn’t care as much, but I still have those moments where I cringe a little when I see myself naked. That is until I met Leo. He makes me feel beautiful.

  “Spread your legs for me baby, I want to see that pretty pussy.”

  I open my legs for him, propping my foot up on a chair so he gets the best view possible. He growls with approval. He grabs one of the oversized pillows in the pile in the cozy little reading corner and puts it under my ass to prop me up. Now my ass is exposed to him along with my pussy. It’s a vulnerable position to be in, but I trust him and so I allow myself to just lie here, spread out for him to see every part of my body.

  He holds my hip and lowers his head. My eyes flutter closed when his skillful tongue starts to work at my wet pussy, swollen with want.

  “I want to try something, okay? If you don’t like it, you can stop me, but I think you will,” he says.

  I nod, a little nervous. But again, I trust him. And right now I’m open to just about anything as long as I’m with him.

  He leaves and comes back a moment later with coconut oil. My eyes widen a little. He puts some on his fingers. My breathing quickens as his oiled fingers disappear from my sight between my legs. He rubs my asshole gently.

  “Relax,” his says.

  I take a deep breath and allow my body to release the tension. That’s when he slips a finger into my asshole. I moan. It’s a little uncomfortable at first, but as my body continues to relax, I find myself enjoying it. He sucks my breasts and nipples as he fingers that previously out of bounds place. My whole body seems to open up. All my nerve endings come alive until I feel like I might come without my pussy even being touched.

  “Oh my God, why does that feel so good?” I ask as he adds another finger to my hole.

  “There are a lot of nerves attached to that area,” he says, and there’s something very sexy about how he uses his teacher voice at the same time he has his fingers in my ass. It’s naughty. “And if you relax and open your mind to it, it could be the best sex you’ve ever had.”

  He doesn’t ask if I’ve ever done anal. It must be apparent that I haven’t. I’ve always been a little afraid of it and I’ve never been with someone who could make me feel comfortable with it. But I’m comfortable with him.

  He expertly works my asshole with his fingers as my hips roll and thrust upwards toward him. He chuckles. “You like that, don’t you?”

  “It’s amazing,” I say breathlessly.

  My body feels weightless, like putty, all stretched and w
onderful. There is not a single tense muscle. And that’s when he pulls his fingers out and lines his dick up with my asshole. And I want it. Even though his cock is huge, I know I can take it.

  I look him in the eyes and tell him. “Fuck my ass.”

  He smiles devilishly and slathers his cock with oil until he’s glistening. He slowly enters me and my back arches off the pillow. He reminds me to relax and I do. With each of my deep breaths, he pushes in a little further. The first part is the worst. It’s not terribly painful, but it’s painful none the less. The large head of his cock squeezes past my tight, tender opening. I yelp when he pushes it through.

  He stops to let my ass get used to this massive intrusion. “Are you okay?” he asks. I’m breathing hard. I nod, but I don’t know if I totally am.

  He uses his thumb to work my clit and the pain completely subsides. This time I do relax fully. “Keep going,” I say.

  He pushes slowly until his entire cock is in my back entrance. It feels so full, but not uncomfortable anymore. As I get used to him, it’s actually a great feeling, and the fact that it makes me feel rebellious and a little dirty, makes me like it even more. Prudish good girls don’t let men fuck them in the ass. Half the fun—other than the physical part, which is incredible—is how empowered it makes me feel.

  He pours more oil on his cock and my opening as he starts to move faster and deeper. I keep reminding myself to relax, and as I do it becomes more and more pleasurable.

  “You like my cock in your ass?” he says, watching my face the whole time.

  I bite my bottom lip. “It feels so good.”

  His lips tilt into a cocky smile. “You’re my dirty girl, aren’t you?”