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The Yellow Book Fantasies, Ch. 4: Ms. Jackson, I Am For Real

Chad Dupree befriends a dancer. It eventually turns into lust...

Have you ever had a real, genuine friendship with the opposite sex? That happened to me once or twice. Her name was Olivia Jackson. I formally met in my sophomore year of high school. We were both sixteen at the time we met. However, I was not the only one watching her.

 

I was in lunch talking to my best friend, Paul (who is just as much of a horn dog as I am, if not more) about girls and how our day went, when I saw her. I froze, staring at her voluptuous buttocks swaying side to side in those pants. Paul was in the middle of a soliloquy about somebody annoying him when I interrupted him…

“Paul, look over there,” I said, still looking at her.

“Where?” Paul replied, looking the wrong direction. Olivia was clear across the cafeteria.

“That way, idiot. Damn, she got an ass on her!” I said, pointing, then looking.

“Oh, her? That’s Olivia,” Paul said.

Olivia was socializing with a few boys on the other side of the cafeteria, smiling and laughing. She was a pretty ebony-skinned girl with a big smile. I liked that. I kept one eye on her for the remainder of lunch. The bell rung to go to our next class when I got asked by Paul:

“You really don’t know her?”

“No, man,” I said, while trying to see what she had on. I was really nearsighted with glasses on. She had on green pants showing off her curves nicely and a tank top and a jacket that said “WINGS”.

'She’s a dancer?' I thought. There was something about her. Something. The feeling wasn’t there in my loins yet. That was not the only time I would see her.

 

A few months later, I would eventually get picked by my English teacher to go on a college field trip. That field trip was for her college prep class the next year that I would be part of.

Now, on this field trip, I had no intention but to pay attention and to see the sights. But Olivia was on this trip. After a tiring, yet interesting hot day on campus, I was walking to the bus to go back to our school when Olivia called me by name.

“Chad.”

I jerked my head. I only knew about five people on this trip. I wondered how did she know my name.

“Yeah?” I answered.

“You tired? Because I am,” she said with a smile.

I looked at her face, smiled and nodded. She could tell I was shy, obviously. I looked back to see two other girls giggling over the tour guide we saw.

“What was up with him?” I mustered to say about him.

“I think he’s gay,” she said, shrugging.

“Okay,” I said, simply, fighting off laughter. She went on in front of me, while I got another look at her beautiful ass sashaying in those jeans. Not long after that, a girl that I actually knew on the trip jerked me out of my reality. Her name was Julissa.

“Hey, Chad. I see you looking at her booty,” she said, teasingly.

 

The next year started my junior year. I had my college prep course sixth period that year. I had it for two years. It took me a while to get used to it, but I sat by Olivia almost all the time those two years. Was it a sign? Maybe. My friends in the class were these boys from the football team, Blake and Tim, that I met freshman year in separate classes. They were not your average stereotypical jocks. They were smart, talented, and good looking. They could get girls in their sleep. They sat next to Olivia (to most likely check her out), who sat in front of me almost every day.

“Hey, Chad!” she said, happily.

“What’s up, Liv?” I said, with a voice deeper than usual. As I got more comfortable around her, I used her nickname. She would soon get a new nickname.

“What’s up, Wonder Booty?” my friend Blake said.

I snickered.

“The hell you called me?” she said, standing up once again, giving me the view of a lifetime.

“You know, Wonder Booty,” his partner in crime Tim said, motioning the curvature of her ass. “You don’t like it?”

They called her that so much they made a song out of it:

“Wonder booty! Wonder booty, Wonder booty, Wonder booty!” they both chanted.

At this time, I was laughing.

“Shut up, Chad!” she said.

“I’m sorry. But that’s funny. I will stop now. Sorry,” I said, quickly.

“Stop looking at my booty!” Olivia said to Tim jokingly.

“You know that ain’t going to stop, right?” I said in a low tone, trying to be witty.

“Shut up, Chad!” she said.

“Did I say that out loud? I’m sorry, Ms. Jackson. I am for real,” I said looking at her yoga pants. I could see exactly what kind panties she had on.

Before she went to the restroom, she looked at me sincerely and asked, “Chad? Do you look at my booty?”

Frankly I was surprised she didn’t know. This was my answer… “Who doesn’t look at it?”

 

After that day, I was on my way to choir practice when she stopped me.

“What’s up, Liv?” I said.

She got straight to it. “Chad, let me ask you a question.”

“Yes?” I said.

“If I let you smack my ass, would you do it?”

My penis instantly started to get erect. I froze to see if this was some joke or something.

“Are you serious?” I said.

“I think he’s serious,” she directed to my already erect penis, smiling. “Go ahead. You’ve looked at it. Smack my ass.”

I smacked it lightly.

“Ooh. Harder. Do it again,” she said, looking back at me. She bit her lip. I did it again, only harder.

“Ooh, Daddy. You want this pussy, do you?” She said, licking her lips, and feeling my erect member. I squeezed her buttocks and attempted to lower her pants.

“No, no, no. Not yet. Meet me in the band hall after practice.” Olivia then gave me a short but sweet kiss goodbye.

 

In the band hall after practice, Olivia quietly called me over in one of the changing rooms. I quickly and quietly got in with her. She passionately kissed me.

“I’m so horny. Fuck this pussy,” she said in between breaths.

I pulled down her yoga pants in one try, which revealed her seemingly innocuous pink panties decorated with leaves. I slapped her buttocks and complimented her panties.

Needless to say, she dropped them quickly revealing herself and began fondling me. She sucked my fingers with her big juicy lips while I fondled her. By that time my pants (and underwear) were down and she was sucking my penis with vigor while moaning slightly. It felt heavenly.

“Take your shirt off, Liv,” I said. She was small chested and rather self-conscious about it. She did it reluctantly.

“Hey. You’re gorgeous,” I kissed and suckled her small breasts and made my way down her fit yet curvy body to her glorious mystical being. She moaned quietly.

“You like that?”

I kept on going. She was moaning, my erection was getting harder and harder.

“Put your dick in me, Daddy,” she breathed. I then stood up and carefully put my penis inside her. She moaned. It came close.

“Ugh!”

I looked her directly in the eyes and started to fuck her with passion.

“Ugh, ugh, ugh! Oh, fuck! Oh, Daddy…”

I put my hand over her mouth. She sucked my fingers again.

“Turn around, let me see that ass,” I said.

She bent over, I slapped her ass cheeks while she looked back.

“You like that shit?” I said, while I inserted my member into her.

“Yes, Daddy! Yes! Ugh! Ugh!” She moaned as I continued to slap her cheeks and penetrate her with as much primal passion as possible. Eventually, I couldn’t hold it anymore.

“I’m coming… ohhhhhh.” I came on her lower back and right butt cheek. “Sorry about that.”

“It’s ok. I got a question though. You’re going to keep this between us, right? Because these people… ooh.” Olivia said, shaking her head in pity, while also putting on her shirt nonchalantly like nothing happened.

“I got you. Does this make us like lovers and friends?” I said, pulling up my pants.

“We’ll see, Mr. Dupree. Oh, and about my boobs…”

“Ms. Jackson, I was for real.”

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