True story: Feels Like the First TIme – Chapter 2

by melanieatplay

“Okay, stop. You’re freaking me out.”

“How am I freaking you out?

“You know… this… this whole thing.”

“I can’t get one of my brother’s friends a glass of iced tea and ask him how he’s doing?”

“You’ve never said more than two nice words to me since I’ve known you… and…”

“And what?”

“And just being in a room alone with you, that’s enough to get my ass kicked if your brothers knew, so you had better start telling me what this is about.”

I look down sheepishly.

“I want to learn about sex.”

“And you want me to teach you? Are you fuckin’ kidding me?”

“What’s so wrong with you teaching me?”

“This whole thing is wrong, on so many levels.”

I gave him a few moments to calm down; agitating him like this wasn’t going to get me what I wanted.

“First off, I have a girlfriend, do you know that?” he asked.

“No, I didn’t.”

“Well, I can assure you, she wouldn’t think much of this conversation.”

That brought a little smile to our faces, so I knew I still had a chance.

“The next problem is the three guys who are swimming in the pool back there, who just happen to be my best friends.”

“We could be careful, and they’d never find out.”

He gave me an exasperated look.

“Even if they weren’t my best friends Melanie, you don’t mess around with the little sister of the three nastiest rats in the shithouse.”

That brought a big smile to my face because that’s exactly what they were.

We silently sipped our tea for a few moments. I was losing the battle, and I desperately needed to turn this around.

“Okay, Anthony… You don’t think I’ve noticed the way you look at me when you’re here?”

He looked down self-consciously.

“You’re beautiful, and I’m a guy, of course, I’ve noticed you.”

I could feel myself blushing. It was the first time that anyone called me beautiful.

We looked into each other’s eyes.

“Fortune favors the bold Anthony, and sometimes you just have to take what you want.”

He gave me a disconcerted look.

“You’re making it really difficult for me to do the right thing here, I hope you know that.”

I gave him a self-assured look that I very clearly wasn’t feeling inside.

“I’ll put my cards on the table, Anthony. It’s either going to be you, or my second choice, but one way or another, this is gonna happen.”

I hadn’t thought this through enough for there to even be a second choice, but he didn’t know that, and hopefully, he wouldn’t call my bluff.

He paused for a few moments as he thought.

“I’m taking my life into my own hands here, but okay.”

I gave him a big flirty smile. Victory!! It also taught me a valuable lesson that I’ve used many times thereafter. If you appeal to a man’s base instincts, more often than not, you’ll get what you want.

**********

Day One

It was Monday and I agreed to meet Anthony after school at his house. It really was the perfect location because he was an only child, and his parents both worked.

I felt bad lying to my mother, but under the circumstances, I really didn’t have much of a choice. I told her there was a new tutoring program after school in the library and I could get the service hours I needed for the National Honor Society by assisting other students. She loved that I was ‘helping’ my peers and agreed to let me do it, as long as I was home for dinner. It was perfect because it gave me a solid two and a half hours where no one would question my whereabouts.

The only problem with my perfectly devised plan was my very nauseous stomach that was in no way cooperating. I was so nervous and apprehensive; I knew if I didn’t settle myself down, I was going to vomit. Needless to say, it was very difficult to get through the day. I found it nearly impossible to concentrate in my classes, and even Jenna and Erica’s sex talk and snide comments didn’t seem to bother me.

“Mel, are you sure you don’t want to go to the nurse?” Danielle said, with a concerned look in her eyes during our math class.

“No, I’ll be fine. I think I just ate something bad for breakfast.”

“Your face actually has a green tint to it.”

“Just get your math problems done Miss nosey,” I said, while gently rubbing her thigh.

She gave me a soft smile, shook her head, and got back to work. She was right, though, I probably should be in the nurse’s office. I was just hoping I had the guts to go through with this.

**********

I very hesitantly knocked on Anthony’s back door. Even though he lived a block over, we thought it would be wiser for me to use the backdoor instead of the front, just in case somebody we knew walked by.

I watched as the door opened.

“Hi Melanie, come on in.”

I stepped inside and we walked through a small hallway, past the washer and dryer, and into the kitchen.

“Do you want something to eat, or drink?”

Eat? Do you want me to vomit all over you?

“No thank you, I’m fine.”

A few moments of very awkward silence passed.

“Would you like to… ummm… watch TV?”

Oh my, God Anthony, are you trying to kill me?

“No, let’s just… you know… ummm…”

“Okay Melanie, I’ve got to be honest with you, it normally doesn’t happen like this. I’ve never had a girl just show up at my back door and then want to get laid, you know?”

I looked down feeling deeply embarrassed.

Maybe this was a bad idea.

“I’m sorry Anthony, I… you know… this is my first time and I… I… have no idea how this is supposed to work… and I’m incredibly nervous, but I didn’t mean to weird you out or make you feel uncomfortable… it’s just that…”

I was seconds from breaking into tears.

He took my hand and looked into my eyes.

“Melanie stop. It’s okay, and I’m sorry. C’mon, follow me.”

He continued to hold my hand as he led me out of the kitchen and into the living room. I would love to describe their furnishings, decorations, and wall colors, but honestly, I didn’t even look. I felt nauseous and dizzy and I was hoping I wouldn’t pass out as we walked up the stairs and into his bedroom.

We faced each other and looked into the other’s eyes for several seconds.

“I’m going to get undressed in the bathroom,” he said. “Why don’t you get undressed and then get under the covers, okay?”

“Okay.”

I watched as he walked out of the bedroom closing the door behind him.

I very quickly removed my clothes, slid under the covers, and pulled the blankets up to my neck, making sure none of my naked body was exposed.

And I waited… and waited… and waited… and waited… and waited…

It was probably only about a minute, but it felt like hours.

Finally, the door opened, and Anthony walked into the room naked, carrying a towel.

I questioningly looked at the towel in his hand, and then back up at him.

“It’s for if you… you know…”

“I understand,” I said softly.

I also looked at his penis. It seemed kind of long and sorta thick, but I didn’t really have a base of reference to judge it by. I then remembered Jenna and Erica very shamelessly discussing the size of their boyfriend’s cocks at lunch and I recalled them saying they had even measured them.

I tried to make an educated guess. Did Anthony look like he was five inches, or six inches, or…

Anthony’s voice broke me out of my deep reflection.

“Can you slide over Melanie?”

I very quickly slid to the far edge, and he pulled the covers back, while still ensuring that my naked body was still covered. He then laid the towel down in the middle of the bed.

He slid in beside me and I hesitantly slid towards him, ensuring that my bottom was on the towel.

He leaned in and very cautiously kissed me. I loved kissing guys and normally I was really good at it, but this time, I was so nervous and apprehensive, we probably looked like two fish hitting glass.

I tensed up when I felt him touch my breasts.

“You need to relax a little Melanie; this is supposed to be fun.”

“I’m having a really good time Anthony.”

That was a lie, and we both knew it.

His hand traveled lower, and I shivered when he touched my stomach. Thankfully, I didn’t feel like I was going to throw up anymore, but I still felt sick from being so nervous.

His hand traveled further south and I could feel my pubic hair brush through his fingers. I had to fight the intense desire to close my legs and deny him access to the most private part of my body.

He continued to kiss me as his fingertips lingered over the lips of my vagina. His mouth retracted from mine and he whispered into my ear.

“God you have such a sexy body Melanie.”

“Thank you,” I said shyly.

I couldn’t help but think that his fingers and sensual words should be turning me on and getting me into this, but they weren’t, and he knew it.

“You should be getting more… never mind… let’s try something different.”

“Okay,” I said hesitantly.

He rose and stood beside the bed and pulled open a drawer on his nightstand and produced a big jar of Vaseline. He then reached back into the drawer and pulled out a condom.

I look down at his very erect penis, and I was a bit taken aback. It looked a lot bigger now compared to when it was flaccid when he walked into the room. There was also a clear liquid oozing out of the slit in the head. Even though what we were doing wasn’t working for me, it was obviously doing a lot for him.

—————–