A gay sex stories: The Wager
*****The following story is inspired by events and events I experienced. Also, every character in the story is 18 years old and is completely fictional. Enjoy *****
The Wager:
It was 7:45 in the morning when I found myself on a bench reading a book in the school parking lot. Students and teachers were swarming in as we grew closer to the first bell ring. I didn’t care, my classroom wasn’t far. Which gave me plenty of time to read my book.
Which didn’t last very long as I felt a hand on my shoulder, “Hey, Alex! What are you reading there?”
It was Dean, my best friend. We’ve been friends since middle school. Both of us were gay and we’d often crush on guys together. Dean sat down next to me.
“Dune,” I finally answered.
“Ah, I see. I finished my sketch last night!” Dean said as he brought out a piece of paper with his drawing on it. It was a lady with a lavender-colored long dress and a matching hat. Dean was an artist. He loved to design clothing with his dream of one day becoming a clothes designer.
“Wow! This looks so beautiful! I saw you modeled it after Jessica Wrothchild,” She was a famous fashion model.
“You know it, girl! I’m working on a new design but for a man,” he handed me a sketch.
“I can’t wait to see your clothing in stores.”
Dean nudged me, “Thanks, I appreciate it. But what do you think of the waist? I was thinking of doing more of a ribbon effect…”
The conversation was cut short when we heard the roar of an engine. Quickly we turned out attention to the source of the roar. It was a Ford Mustang GT that drove into the school’s parking lot. The shiny clean car was white and had two blue strips that ran across the top of the car. It drove past us, deafening our ears with the engine’s roar.
The Mustang came to a complete stop a few feet away from us. I already knew who the driver was, it was Ellis Williams. The door of the Mustang opened and Ellis stepped out. He wore blue jeans with a plain black T-shirt that was tucked into his pants. The clothing showed off his slim figure. Ellis was a fine man. He was tall and lean, but the muscular type. He had a clean-shaven face with blonde short hair. And his eyes were blue as the sea. I had a crush on him but I knew I’d never even get a chance with him.
Ellis walked to the trunk of his car and bent over to grab his backpack. This gave us the view of his well-toned ass in his snug jeans. Which was given to him after so many years of basketball. He hung the backpack over his left shoulder causing the keychain on his backpack to shine, blinding us briefly. It was a Ford Mustang keychain. His father worked at a Ford dealership as did his grandpa before. The ’67 Mustang Ellis was passed down through the generations, from his grandfather to his father and finally to Ellis. He took care of the car because he knew how important the vehicle was. He let no one lean against it, not even his girlfriends.
Ellis closed the trunk and walked towards us quickly noticing us.
“What’s up, sticks?” he said in a teasing tone. It was a nickname he had given me back in middle school. Yes, that’s how long I have known him. But it’s also the same amount of time I’ve had a crush on him.
Ellis grabbed my book and looked at the cover, “Dune? Isn’t that a movie or something?”
“Yes, but it was a book before.”
Ellis shrugged and tossed the book back on my lap. He then turned to Alex and said, “What up shitstain?” A grin wavered on his face.
Dean rolled his eyes and was about to speak when Ellis just walked away from us.
“You poop once in class and you get the nickname ‘shitstain’ for the rest of your school life,” Alex cried, “But I don’t mind it because I get to see that ass of his walk away from me.”
I smiled, “Yeah, it’s always a great view. What I’d do to get that man in bed with me.”
“I’d imagine his cock to be hung and long,” Dean commented.
“Very veiny with a trimmed bush,” I added.
“His balls would hang low.”
“Stop it, you’re getting me aroused. I might have to rub one out before the first period.”
“Maybe we’ll make it a duet,” He smiled. “I wonder what type of underwear he wears? I remember back when we had P.E. he’d wear boxers and boxer briefs.”
“Definitely, the latter. It is quite popular now. I’m glad P.E. is over for us seniors. I had to wear boxers over my briefs for those two years of P.E. remember?”
“Ah yes. The days we couldn’t be seen with briefs on or we’d get a wedgie.”
“You think a guy like Ellis would ever do anything with a guy?”
Alex bit his lower lip, “Not unless you got money. And loads of it.”
“I think If I work some overtime, I can get a load of money,” I said jokingly.
“No way!” Alex spat out. “This guy has slept through a quarter of the cheerleader squad. He is super straight. He ain’t going to let a faggot like you have his way with him.”
“I’m confident I can.”
Alex raised an eyebrow, “Is that so? How about we make it a bet.”
“Alright, what are we wagering?”
Alex thought about it for a few seconds then said, “If you managed to get him to sleep with you with proof, I’ll convince my cousin to sleep with you.”
“Your cousin Allen? How will you do that?” Allen was his hot track runner of a cousin. I had a massive crush on him too.
“We’ve done a few things growing up. He has sworn me to secrecy but I think I can convince him to let you have fun with him.”
“And if I lose?”
“You top me for the rest of the school year.”
“But I don’t like to top. Ugh fine,” I put my hand out, “Deal.”
Alex placed his hand on mine and said, “Deal. Good luck. I heard he fucks like a jackhammer.”
“Is that so? I doubt I can get him to fuck me, but maybe I can get him to let me suck him off.”
“I wish you all the luck, my friend.”
The bell rang. We both got up and went to our respective first periods.
As the school day went on, I thought of the ways I could get into Ellis’ pants. I couldn’t just ask him. I feel I would get a punch to the face if I did that. Plus he’d probably tell everyone and I would be the laughing stock of the remaining months of school. Bribery was another option. I worked but I didn’t have a lot of money to spend. And even if I did work overtime, I don’t think it would be enough. On top of that, I was saving up for a car. I definitely needed one if I wanted to visit Dean after graduation. But I also wasn’t even sure how much he would ask for. It honestly felt like I needed a miracle to pull it off.
It was lunchtime and I had just finished my food when Dean came to me, “So how’s the plan going?”
I turned to the right and saw Ellis with his group of friends at a table. At the corner of the table was his best friend, Marsden Matthews. In Marsden’s arms was his girlfriend of practically all of high school, Tracy Langsford.
“I’m still working on it.”
Dean crushed a grape between his teeth, “You have Ellis, but I have Marsden over there. That man can choke me while he fucks my hole.”
“Maybe you can convince him to fuck you while Ellis fucks me?”
“As if. Marsden is madly in love with Tracy. It would be harder to get him to sleep with me than Ellis with you.”