The Dating Lesson

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 wonderful. 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?”

I lick my lips and nod.

“Fuck, you feel so good. I’m trying not to come. I don’t want this to be over,” he says.

He spreads my pussy lips with one hand and shoves fingers into my pussy with the other. I cry out as I’m suddenly stretched further. He manages to rub my clit as well. I could explode right now into a million different pieces. There’s pain and pleasure. Nirvana, euphoria. I’m on a different planet, never having experienced pleasure even close to this in my entire life. I never want it to end.

“You’re so fucking tight,” he growls. “Oh fuck.”

He starts to move his fingers around inside of me and it’s over. He hits just the right spot and my body erupts.

“Oh, God,” he says, his voice urgent. “Holy shit!” His words are followed by a long groan of pure bliss.

My own juices spill out of my pussy around his fingers at the same time his spills out of my ass. He pulls out and it’s a torrent of wetness. I have a feeling his pillows will be ruined after this.

He lays next to me, breathless and spent. “Jesus, you’re a freak of nature,” he says with a chuckle. “No one should feel that good. I think you’ve ruined me.”

I laugh because I know exactly how he feels.

We spoon for quite some time, not speaking, just living in this moment, letting our bodies come down from the high they were on moments before. At some point we both doze off. It’s almost two in the morning when my eyes open and I realize I’m still naked on his floor.

“Shit,” I say.

The sound of my voice wakes him up. He looks at the clock. “I didn’t even realize we fell asleep, but after what we just did, I’m not surprised.” He kisses me, not seeming as concerned as I am even though we both have to be up for early classes.

He insists on walking me back to my dorm since it’s so late. Campus security is basically just one officer patrolling an entire campus at this time of morning and Leo wants to make sure I get back to my room safely, all the way to my dorm room door.

We sneak through the halls. The high heels I wore for our date clap against the tiled floors of the dormitory and are about as subtle as thunder in the quiet corridors, so I take them off and walk barefoot. I open the door to my room, thinking Brenna will be asleep. To my shock and horror, she’s wide awake, sitting at her desk. She looks over at us and her eyebrows go up when she sees Leo with me.