I was a naïve teenage boy, horny like most guys my age, living in a small town in Northern Michigan. My older brother and his friends liked to give me shit a lot about being nerdy and clueless, and teased me mercilessly about not having a date to the school dance.

“When we were in high school, we never had any trouble getting dates. What’s wrong with your little brother, Simon?”

“Jack, lay off, okay? Otherwise, I will never hear the end of it from my ma.”

“Oh, does little Danny boy run to mama when we pick on him?”

“As a matter of fact, he doesn’t, but somehow our ma always figures out that something’s eating Danny, and she pesters it out of him.”

“Danny wishes something was eating him,” Jack laughed.

Simon sighed. It was annoying as fuck the way their mom rode his ass about helping Danny make friends and looking out for his shy little brother.

“Jesus, Danny, you’re seventeen. It’s time to stop being afraid to talk to girls,” Simon chided him.

“Easy for you to say. Girls have always fallen at your feet. They never notice me.”

“Hey, how about you let me fix your brother up with a girl for the dance on Saturday?” Jack asked. “I’ll find you a real nice one. Then it’ll be up to you to impress her, of course.”

“You’d do that for me?” I asked.

“Sure, what the hell. Why not? You’re Simon’s kid brother. I will see if Rosy is available. Rosy Palm.”

I was suspicious, but the biggest obstacle was getting a girl to say yes to going out with me. If I had a date lined up, I’d just have to work on making small talk. I could practice that in the mirror.

A few days later, I saw Simon and Jack hanging out in the yard.

“Hey, um, Jack. So, did you manage to find me a date for Saturday?”

Jack laughed hysterically and then made his face somber. “Sorry, Danny. No luck. You see, most girls are looking for a guy with the balls to ask her out on his own.”

I hung my head and sighed.

“Hey, but there’s always Miss Michigan.”

“Miss Michigan?”

“Yeah, I bet Miss Michigan shows up without a date and would be more than happy to hook up with you.”

“Really?”

Boy, was I fuckin’ naïve!

“I’d bet money on it. So, here’s what you do. Jack off on Friday night so you don’t cum in your pants on Saturday. Then show up at the dance with flowers and wait for Miss Michigan to find you.”

On Friday night, I took Jack’s advice. I grabbed the porn mag I had stashed under my bed, some baby oil, and a towel. I sat in the chair in my room holding an old issue of Playboy in one hand and my growing manhood in the other. As the models spread their legs to expose their glistening pussies, I stroked my throbbing dick, imagining that my next move would be to slide inside one of those hotties. It felt so good, visualizing thrusting into a sweet, hot box, that It didn’t take long for my balls to constrict and let go, covering my stomach with rope after sticky rope of my cum. Then I hurried up and made a beeline for the shower so I wouldn’t get caught and, hence, ridiculed by my brother.

The next day seemed to drag on forever. Finally, dressed nicely and eager to meet Miss Michigan, I headed for the school gymnasium.

I waited a few hours at the dance on Saturday night, feeling stupid for wasting my time. No one came up to me at the dance. In fact, no one paid any attention to me at all. As I made my way to the exit, Sarah, a pretty blonde with blue eyes and a hot body from my A.P. Lit class, ran straight into me. I noticed that she’d been crying.

“Hey, Sarah, are you okay?”

“No, I’m not. I just caught Steve with another girl in the parking lot. He said he had to go to the car to get something and would be back in a few minutes. When he didn’t return, I went to see what was taking so long.”

It took me a moment to catch up; her boyfriend was Steve Compton, captain of the basketball team.

“What happened?” I asked, genuinely sorry to see her so upset.

“What happened? I’ll tell you what happened. His cock got stuck in Rita Miller’s throat! That redheaded whore! I only came back into the dance to get my purse. I’m going to see if I can grab a ride home with one of my friends who came stag.”

“I can drive you home,” I offered, stunned at my sudden burst of courage. “My brother, Simon, and his friend, Jack, were supposed to set me up with a date. They couldn’t find anyone but said something about Miss Michigan showing up. But she never did. So, I was just about to leave.”

Sarah raised an eyebrow. “Miss Michigan?”

“Yeah, I know. It was a long shot, but Jack said Rosy Palm wasn’t available.”

“Danny, they were yanking your chain,” she said, pity written all over her face.

“I figured that out when she didn’t show up.”

Sarah frowned and tilted her head. “Danny, don’t you understand what they meant?”

“Um, not really.”

She sighed. “Danny, Rosy Palm and Miss Michigan are like code words.”

It was my turn to frown. “Code words for what?”

Sarah blushed. “You know, for, um, well, when a guy masturbates.”

I stared at her in disbelief, so she continued. “Danny, when a guy jacks off alone, it’s called Dating Miss Michigan.”

She held up her hand, and suddenly I wanted to crawl under a rock.

“I’m so fucking stupid,” I said, turning away from her, mortified. God, my brother was such a dick!

“Hey, I guess we were both stupid tonight,” she said, putting her hand gently on my arm. “So, if that offer is still good to drive me home, I’d appreciate it.”

Still reeling with embarrassment, I almost declined. But manners forbade me to leave this lovely girl without a ride.

“Sure thing,” I said. “Will Steve get mad if he finds out I drove you home?”

She hooked her arm around mine as we headed to my car and said, “I like you, Danny. You’re always such a sweet guy. I’m done with dumb jocks like Steve. Besides, he made his choice when he got in his car with Rita.”

I noticed Jack and Simon leaning against my car when we reached it. They seemed poised to give me shit about the fact that I’d fallen for the Miss Michigan ruse. But when they saw Sarah on my arm, they looked shocked.

“Hey, guys, what are you doing here?” I asked.

“We just wanted to see how things worked out.”

Before I could answer, Sarah spoke up. “Fortunately for me, Miss Michigan never showed. Good thing, because I’ve been dying to get my lips around this hottie’s cock for weeks. Now, if you’ll excuse us, gentlemen, Danny is going to drive me home.”

I thought Jack and Simon were going to shit themselves. They moved away from the car but continued to look on in awe.

Sarah grinned at me and, loud enough for the guys to hear, said, “Or, maybe we’ll find somewhere to park on the way home. That way, I can suck you a little before I let you take my cherry.”

I felt my dick growing in my pants and hurried to open the passenger door for Sarah. I shot what I hoped was a shit-eatin’ grin at my brother and his asshole friend, got in the car, and drove off.

“Thanks, Sarah, that was sweet of you to say all that so those guys wouldn’t think I’m a total loser.”

Sarah surprised me when she put her hand on my bulge and said, “Those weren’t just words, Danny. I’ve been watching you for weeks in class and at lunch and wondering what it would be like to be with a genuinely nice guy. I can’t believe I was going to let Steve be the one to take my V-card. I’d much rather lose my virginity to you.”

“Oh, well, um. I didn’t come prepared with, um, a condom.”

“No worries, I have a three-pack in my purse.”

My eyes grew wide. But my heart was suspicious as I pulled off on a secluded road by the park.

“Sarah, I like you, but I’m not sure I’m ready for this.”

“Your pants say otherwise. How about this, you let me suck your cock while you finger my pussy. Then, if we are both so aroused that we need to take it to the next level, I’ll let you fuck me.”

“Is this really happening? Or did my brother put you up to this?”

Sarah looked a little hurt. “Okay, I get why you might think that. But I swear they had nothing to do with this.”

I relaxed and let my dick out of its restraints while she took my hand and guided me into her damp panties. I was grateful I’d jacked off the night before so that I wouldn’t cum in seconds. At least that part of Jack and Simon’s advice had been helpful.

I slid a finger into what felt like hot, wet silk and felt proud when she moaned softly. Moving my fingers around made the moans louder, so I got braver and added another finger.

“Oh, God, Danny!”

She grabbed my dick and gripped it while she sucked on the head. Then she took more of me into her mouth and put that hand on my sac.

It was my turn to moan. I tried hard to split my focus between fingering Sarah’s sweet pussy and enjoying her mouth on my cock. But when my thumb connected with a hard little nub, it was like I’d given her an electric shock.

“Sarah! Did I hurt you?”

She panted and rubbed her body against my hand till I felt a gush of liquid.

“Did you just pee on my hand?”

“No, silly,” she panted. “You just made me cum. In all the times that Steve fumbled around down there, he never got me off. Oh, God, it was amazing.”

“I didn’t know girls shot jizz.”

Sarah rolled her eyes. “We don’t shoot jizz; we squirt female ejaculate.”

I must have looked confused because she clarified, “Girly juices.”

I nodded. “Hey, do you really want to do it?”

“If you’re asking me whether I wanna fuck, then yes.”

She handed me a condom, and I fumbled with it a bit, but her gentle fingers helped me accomplish the task.

Straddling me, she lowered herself slowly onto my stiff pole and said, “So much better than fingers.”

I grinned and said, “So much better than Rosy Palm.”

She laughed, and all the awkwardness I felt drifted away and was replaced by a new sense of wonder. She felt so soft inside, even with the condom, and my dick was in heaven. She bounced up and down on my cock, panting and moaning like a bitch in heat. And each stroke made my balls ache more.

God, it felt good to fuck her tight pussy! She was hot and eager, and I knew I wouldn’t last much longer.

Right before my balls let go, she screamed, “Oh, God! Yes!”

I ramped up the speed and fucked her until I filled that condom with my spunk.

“I hope I didn’t hurt you; I know it’s supposed to hurt a girl the first time.”

Sarah bit her bottom lip and said, “Okay, technically, I broke my hymen months ago when I masturbated with a banana. But yours is the first dick to feel the inside of my pussy. So, you’re still my first.”

“Why did you have the condoms in your purse?”

She shrugged. “I was planning on letting Steve have this honor, but he was too busy fucking Rita’s face.”

“So, um, does this mean you’re my girlfriend now?”

“Did you want me to be your girlfriend?”

“Well, yeah! But what about Steve?”

“Steve who?” she teased.

I raised an eyebrow at Sarah. “Would you be my girlfriend?”

“Yes.”

I grinned. “I should probably take you home now.”

“Probably.”

As it turned out, Steve broke up with Sarah before she could break up with him. Something about Rita being a better cock sucker. Which sort of blew my mind because Sarah was no slouch in the oral skills department. I’m guessing they had just run their course and needed a reason to break up.

Sarah and I dated for the rest of senior year, but she broke things off when we went our separate ways in college. I was disappointed, but it was for the best, as we were in lust more than love. But boy, did I learn a lot about sex with Sarah, and I will always be grateful for those erotic lessons learned.

Believe it or not, after college, I ended up marrying Rita, the hot little redhead whose oral skills were, indeed, even better than Sarah’s. We ended up at a party for a mutual friend, and sparks flew.

Recently, while we were reminiscing about high school, Rita rendered me speechless when she said, “Did I ever tell you about the time your brother, Simon, paid me to seduce Steve Compton and suck his cock in the parking lot outside the school dance?”

I nearly spat out my beer! When I got past being shocked, I laughed. Maybe my brother wasn’t such a dick after all. I mean, he did set things into motion that led to my ending up with my hot little redhead!

I pretended to pout. “You dirty little girl! Maybe you should show me how you did that.”

Rita laughed. “Well, that might be difficult because your dick is much bigger than his.”

I grinned. “You can always get Miss Michigan to help you out while you suck.”

Rita laughed and held up her hand. “She’d be delighted to play along.”