The Yellow Book Fantasies Ch. 03

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Chad Dupree tells a story about a certain Sweetheart...
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Part 3 of the 14 part series

Updated 06/09/2023
Created 05/25/2018
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Let's go back to my sophomore year, shall we? This next one is an enigma of sorts because I had kind of a love/hate relationship with her. I first saw her on my college field trip sophomore year with her best friend. Now, I only knew about five people on the trip. These two stuck out. They were the epitome of the word "BFFs". They were inseparable. One was very pretty, curvaceous, got the boys' attention in multiple ways, yet tomboyish and just like one of the guys. Her name was Ashley. (Her tale comes later) Our woman is pretty cute. Not ugly but not drop dead gorgeous. She didn't have that much eye popping curves like her friend, which she admits. But the thing about her was: There was always something. Something about her that I could not figure out. This is called "The Tale of The Sweetheart."

Now, why the nickname "The Sweetheart", you ask? Good question. It's simple, she is the sweetest bitch you will ever meet. She takes pride in that. When we officially met in high school, I was trying to figure out people and trying to be sociable. I was cracking jokes in there to my friends on the football team, when she chimed in:

"Chad, shut up. Your jokes are played out."

At that moment, I got pissed off for about three seconds. Then I quickly composed myself:

"Ok. I'll shut up. I'll shut up." I said, while cursing her out under my breath.

Other days, we would have no issues and sometimes we would laugh and talk together. She even sang to me once. It was some show tune. She had a surprisingly good voice. I was mystified. Had I become attracted to her? If so, how?

As the year went on, I began to notice things about her. For example, her eyes were light brown. I had never looked in a girl's eyes before until then. How, I do not know.

One day, our Sweetheart asked me to lend me some money. Now, I am a product of my environment. My grandfather once said: "Never trust anyone around your money" at a young age. So, when she asked me this:

"Chad, can I borrow a few dollars?"

"For what?" I said, exasperatedly.

"I'm going to Jack later, silly!" She said. (Short for Jack In The Box)

I reluctantly looked in my semi-empty wallet and lent her the money.

"You have two days to bring me back my money," I said in my serious voice.

"Relax. You think you're a pimp!" She said, playfully hitting me.

She went on to talk to her friend Ashley who was not far from earshot when I heard the phrase softly:

"Do you want to see what kind of panties I have on?"

I jerked my head along with my penis. The Sweetheart showed them to her. Ashley told her in detail. I was hard. I escaped out the door while I could and looked down.

"Down, boy. Down." I said quietly to my erection. I started to walk it off. All of a sudden, the door opened. It was The Sweetheart. She looked down at my jeans. Her ever-so-observant eyes lit up.

"Oh my God. Chad, are you hard?" She said.

"Shit." I whispered.

"You are! Can I get something off my chest?" She said.

I was intrigued. So, I tilted my head.

"I have a thing for black guys and your big black dicks." She had a look as she said that. As I said before, we were products of our environment. She was part-white, part-Latina. Almost all her boyfriends were black. I'm black. So... do I have a chance? Before I thought about that, she felt up my erect penis in my jeans, and said:

"Let me suck you."

The Sweetheart then took me by the arm to another location. She dropped to her knees quickly and said:

"Drop' em. I wanna see that big black dick."

So, I did. I really didn't know what I had.

"Mmm. I didn't know you had it like that!" She proceeded to suck sensually. It felt heavenly.

"Oh, God. Oh. Spit on it. Spit on it." She did, with the trail flowing slowly from my member.

She kissed my member with her pink sweet lips, then moaned and asked:

"How big is it?"

"I don't know, like 7 to 7.5 inches?" I answered.

She licked it, and felt my balls.

"You got some big balls," She said, feeling them, smiling.

"Literally?" I joked.

She looked at me. I couldn't resist the joke. She resumed sucking it gently. She took off her shirt and her bra, showing her petite breasts. She looked at me in her topless state, and I her in my aroused state. I groped her petite breasts like an animal. She then all of a sudden started jerking my penis off with more speed alongside licking my balls. I began to feel it.

"I'm coming. I'm coming." I said.

She kept jerking me off and sucking until I climaxed. She kept sucking.

"Oh, God, yes. Oh, God." I said in euphoria.

She removed her mouth from my flaccid member, come notwithstanding from her mouth, and smiled. I smiled at her attractiveness while pulling up my pants. She was pretty. I knew I didn't have a chance.

"You liked it? Oh, and Chad..."

"Our secret's safe. You know what? Keep the money. It was only three dollars anyway, Sweetheart," I said. She kissed me on the cheek.

I spent this whole time trying to figure out this enigma of a woman. It turns out it wasn't for me to figure out.

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