My first ever crush was on Sally, my neighbor. We went to the same high school and had the same classes. We even walked home together.
I had tried many times to become Sally’s boyfriend, but she always turned me down. ‘I was too good as a friend,’ that was Sally’s excuse every time I brought it up.
I hated that excuse; it was so lame, but after high school, I was glad to be free of her finally. I bet she is somewhere kicking her ass now.
I blossomed in the college environment. I was the nerd that everybody loved. Even the jocks loved me; I got them good grades for a price and even got them legal aid when they got into trouble.
I could do it all, and the deans and college campus police had no idea that I was the kingpin of the underground drugs, sex, and all the other things that went rampant on campus.
I lost my virginity to one of the hottest cheerleaders ever to walk the grounds. You know that saying that there is no other better feeling for a guy than watching and feeling his cock go into a woman? Well, I finally got to experience it.
That hot blonde rode me hard and fast, and when I came inside her, she begged for more, not because I was a good-looking guy or that I was good in bed, no, because I was filthy rich, and I hadn’t even graduated yet.
I had more money than I could spend in a lifetime before I even graduated college! That’s how well I played the system. Stocks, drugs, music, movies, everything I could get my hands on and trade, or move around or sell, I did it.
The drug dealers didn’t know who or how I was getting them the primo stuff, and the buyers only knew the drop-off spots and my mules were jocks, so if they got caught, the college pushed it under the table because they were good for the teams they played on.
No ranked college sports program would let their star player go down for picking up some drugs, so they always set up some idiot as the fall guy- that’s how I got away with it. I knew the bigwigs in the NCAA wanted to make money off the players; the players couldn’t do anything wrong, and they wanted drugs, sex, and parties to keep playing, so I jumped right in to fill the gaps.
When I graduated, it was the highlight of my life. A house, cars, and fame were waiting for me. I just had to find a way to make it look like I had earned all of it. I couldn’t just pop up with wealth, or the authorities would have a field day trying to find all my money.
That’s when it hit me. I had to go further into sports, further down the rabbit hole, and that’s how I met my wife. Candice was a mark; someone I had seen on television. She was perfect, a bimbo blonde and daughter to one of the richest men in sports entertainment.
It didn’t take me long to get into their tight-knit circle, and before I could count to one hundred, the bimbo was getting fucked by me in the back of a limo. Lucky for me, I had come a long way from the nerdy one-minute chump from college.
One thing the jocks were good for was getting me in shape and helping me score with slutty college cheerleaders, so when it came to fucking Candice, I was the best thing she had experienced.
I had her legs touching the roof of the limo and her big silicone tits bouncing all over the place. I gritted my teeth and went for gold. I wanted her to run home to her father and tell him she wanted to marry me.
Then I would be set! I could put my money with theirs, and not one IRS or financial institution would question my decision.
There was only one problem, one major flaw in my plan.
“Hi,” I said as the door to their mansion opened.
And there she was, the crush I didn’t see coming, Debra, Candice’s mom.
She looked like something out of a Playboy magazine, huge silicone tits, long platinum blonde hair, and a body that made an hourglass jealous.
Debra smiled as I entered their large house.
“So, you are into sports as well?” Timothy said as we walked into the large living room.
“Yeah, I just bought a small team out of Toronto,” I explained. “Trying to start small.”
“Oh, that’s good,” Timothy said. “I heard you are also interested in making them a candidate to enter the Canadian league?”
“Yes, that’s my goal,” I grinned.
I couldn’t keep my eyes off Debra, every move she made my dick throb. She was the perfect trophy wife.
“That’s how I started, made a few football teams, and basketball teams into larger well-established teams, then bought into the networks and streaming services,” Timothy grinned.
“Sports has always been my thing, even though I was never good at playing it myself,” I lied as I sat down with Candice beside me.
“Tim couldn’t catch a ball to save his life,” Debra grinned.
“That’s not true dear,” Timothy said. “It would always hit me in the face or chest, then I would drop it.”
Candice had her hands on my thigh, and all I could think about was her mom and how I would love to plow her massive melons.
“Do you have tickets to this year’s big game?” Timothy asked.
“Yes, I do,” I said as I wrapped my arm around his daughter. “Candice told me you had a part to play in the outcome?”
“Yes, I should say we,” Timothy grinned. “Hardly ever let the big games come down to chance, there is no money to be made in that.”
“I had a part to play in the drama,” Debra said. “Some of the other ladies at the club wanted to see the young woman be with someone of better shall we say tastes than her previous boyfriends?”
“I already have a few song writers working on her break up song,” Candice smiled.
“Oh, so they are breaking up. Is there any word on when?” I asked. “I have a few bets on a few dates and would like some insider information.”
“We can’t tell you all the details,” Debra grinned. “But if things go well, between the two of you then you will be kept in the loop!”
“I think they are going great!” Candice exclaimed.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
“Yes, fuck me!” Candice yelled as I fucked her hard and deep later that night.
It was too bad her bedroom was far away from her parent’s bedroom, damn this big house!
“I think that went well, don’t you?” I asked as I pulled on her long blonde hair.
“Yes!” Candice yelled as I fucked her from behind. “They love you!”
“Good!” I smacked her fake ass as I buried my cock deep inside her.
“If you get me pregnant, they would love you even more!” Candice said as I came inside her.
‘You’re not the one I want to get pregnant,’ I thought as I laid out on the bed.
I had to make plans to seduce Debra. She was my next target. I also had to make more plans to find out Timothy’s other players, something told me that there was someone bigger and more important than Timothy, and that meant there was more money to be made, but for now, I had to make this blonde bitch fall even more in love with me.
“Again?” I said as I got on top of her.
“You are an animal!” Candice squealed as I pushed my cock back into her.
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