"I didn't know you were coming over today, come on in."
"Sorry for the sudden drop in Mikey, but I need your help."
"What with?" He says, turning off the TV.
"Um, it's kinda awkward."
"I'm your best friend Y/N, just say it."
"Actually, that's what makes it awkward."
"I promise that I will still be your best friend, no matter what you say. Shoot."
"Okay well, here's the thing, I've been going out with this guy for a few weeks and uh, we're meeting up tonight and I think he'll want to take it to the next level."
Michael frowns. "What does this have to do with me?" He says flatly.
"Well, I know you've had some experience and I'm a virgin," His eyes widen. "Yes, Michael, I am a virgin but that's not the point. I was wondering if you could teach me how to, uh, you know, how to do the thing."
"The thing? What thing?" He teases, raising an eyebrow.
"You know what I'm talking about." I can feel the heat rise to my cheeks, this is probably the most embarrassing moment of my life. More embarrassing than when I tripped over my own feet in the middle of a busy restaurant, crashing into a waiter and several customers in the process and believe me, that was embarrassing.
"Just help me Mikey, please?"
"I don't see how I can help you with this."
"Just teach me." I whisper.
"You do realize that you just asked your best friend to teach you how to have sex."
"You're right, and it was stupid of me to even think of it. I'm sorry. I'll just leave." I stand up and walk over to the door.
"I didn't mean it like that Y/N, I'll help you okay?"
"You will?" You mutter, turning around to come face to face with Michael.
"So, uh, where do we start?" You question, the butterflies in your stomach feeling more like horses. He leads you to his bedroom, situating himself on the bed.
"Usually you start off by kissing." He states, leaning into your face. "You know how to kiss, don't you?" You nod your head awkwardly and he smiles. "Than kiss me."
You lean closer into him, your noses bumping together in the process. You shyly press your lips to his, allowing him to take control. You start moving your lips against his, your tongue brushing against his bottom lip. "Just like that baby." He mutters, groaning slightly. "Now stick your tongue in my mouth."
You do as he says, your tongue exploring every inch of his mouth, your tongues rubbing against each other every once in a while. "Okay, now move your hips against me. Build up the tension." He says through kisses.
"Like this?" You question, grinding your crotch against his, feeling his little friend get significantly harder.
"Mmm yes, just like that. You're doing great."
"What do I do now?"
"Take off your shirt. Do it slowly, like you're putting on a show."
You pull away from Michael for a few moments, leaving him seated on the edge of his bed. Your hands fly to the hem of your shirt, tugging up the fabric ever so slightly so that some of your skin was visible. You pull the shirt up slowly, just like Michael said. "Now take it off."
You toss your shirt across the room, exposing your bra clad torso to your best friend. He gently palms himself through his tight jeans, his shirt long gone. Without waiting for further instruction, you unclasp your bra, allowing it fall to the floor.
"Damn." He swallows, greedily eyeing your breasts.
"Now what?" You ask, crawling over to Michael. You slowly lower your self onto his lap. "Tell me what do Mikey."
"Um, well, you could let me touch your breasts." His cheeks turning a slight shade of pink.
"Go for it." You choke out, letting your arms fall to your sides.
"Are you sure?"
"Yes, touch me."
He leans towards me, re-connecting our lips. His hands reach towards my breasts. His large hands cup my breasts, his thumb running over my ever so slowly hardening nipple. His hands were cold against my skin, sending shivers throughout my body. "Do you like this baby?" He asks, breaking the kiss while his hands continue to explore my body.
"Mmm. What's next?"
"Take off your pants."
"Already? I think I should tease you a bit more." You smirk, grinding against him once more.
"Enough with the teasing, just take off your pants." He chokes out.
"But I like seeing you like this, in my control." Your fingers gently lace through his hair, tugging softly on his locks.
"For someone who was shy as fuck a few minutes ago, you sure got confident."
"What can I say, I have a good teacher."
"Yes you do and now your teacher is telling you to take off your pants." He begs.
"Fine." Your teasingly pull down the zipper of your shorts, slipping the denim down your legs, the fabric pooling at your feet.
"Nice choice." He states, examining the lacy red underwear you decided to wear for the occasion.
"You like it?"
"I like it enough to take it off, that's for sure." He smirks, slowly regaining his confidence.
"What should I do now?"
"Take off my jeans."
"Whatever you say."
His jeans soon join the pile of clothes on the floor, leaving you both in your underwear.
"Grind on me again."
"As you wish."
You slowly rub your crotch against his now evident hard on. "I thought we agreed to stop teasing?"
"Sorry." You respond, picking up the pace.
"Can we get to the real thing now?"
"Uh, sure. Are you ready."
"As ready as I'll ever be."
"Okay so just take off my boxers." You comply, removing the thin fabric, allowing his cock to breathe. His hard on slaps against his stomach. "Did I do this?" You mutter innocently, stroking him gently.
"Yes you did and you better fix it."
"How can I do that Mikey?"
"Suck me."
"I don't know how."
"Just take me in your mouth and follow your instinct."
"Okay."
You lick his tip, swirling the pre-cum on your tongue. You can feel him tug at your hair, moans falling out of his mouth. You take as much of him as you possibly could into your mouth, massaging the parts that don't fit.
"Are you sure this is your first time?"
"Mmm-hmm." You respond, humming on his cock.
"I'm going to cum."
"Cum for me Mikey, I want to taste your sweet, sticky cum."
"Oh baby." He moans, shooting his load into your mouth.
You greedily swallow every last drop, cleaning up his cock with your tongue.
"Your turn." He smirks, pushing you down onto the bed and getting in between your legs.
You can feel his hot breath against your core, making you ache for him. "You're soaked for me baby." He whispers, sending vibrations against you.
"Do something Mikey, please just do something, anything."
He gently nips at your thighs, slowly moving towards your throbbing heat. He leaves a trail of wet, sloppy kisses along your thigh until he reaches your dripping pussy. He runs his tongue along your slit, a loud moan leaving your lips. He delves his tongue in between your folds, gently sucking on your throbbing clit every now and then.
"Oh my God Mikey, keep doing that."
He licks you up a few more times, before replacing his tongue with his fingers. He pumps his finger in and out of your tight pussy, adding another finger to the mix.
"I'm going to cum Mikey."
"I want you to cum on my face baby girl." He growls, sticking his tongue back into you.
You can feel your orgasm shake your body. "Now what?" You ask, your breath ragged and short.
"Now we get to the real thing." He smirks, glancing up at you. He positions himself at your entrance, meeting your eyes briefly. "Ready?"
"As ready as I'll ever be."
He gently pushes into you, allowing you to adjust before thrusting in and out of you. The room is filled with your moans and the sound of your skin slapping against each other. It was a bit uncomfortable at first, but after a few minutes the odd feeling turned to pleasure. You weren't even sure if you wanted to go out with your date anymore. Michael was amazing.
You ride out your second orgasm alongside Mikey. He falls down beside you, both of you panting as if you just ran a marathon. "Was I good teacher?" He breathes out.
"The best. I don't think I'm going to go on that date after all."
"Why?" He asks.
"Well, I doubt I'll be able to walk and I like you Mikey, I really, really like you."
"You don't have to cancel your date entirely, you can just go on a date with me instead."
"That'd be nice."
