My Classmate’s Bet: A Tale of a Betrayer

The ferry ride to Rye Beach Playland Park was a memorable experience, especially for a group of seniors from Brooklyn. It was an annual tradition that brought us together, and we always looked forward to it. As we boarded the ferry, I roamed around, taking in the sights and sounds of the boat. I stumbled upon a group of guys huddled around my classmate, Chris, who was reclined in a deck chair covered in a blanket. They seemed agitated, but as I approached, they quieted down, and Chris beckoned me to join them.

“What’s going on?” I asked, curiosity getting the better of me.

“It’s Alberta,” Chris replied, his voice low. “She’s not going to be able to go through with it. She’s gotten seasick.”

“What are you talking about?” I asked, confused.

“We made a bet,” Chris explained. “If we could get ten guys to chip in $25, Alberta would give us blow jobs on the ferry ride up to Rye Beach. But now that she’s seasick, we’re out of luck.”

I sat there, thinking about the $25 pot of money. I had very little cash, and the amount sounded appealing. “I’ll do it,” I said, making a split-second decision.

“Really?” Chris asked, raising an eyebrow. “You’ll give us blow jobs for $25?”

“Yes, I’ll do it,” I confirmed.

Chris thought for a moment before nodding. “Okay, you can do it. But you have to promise not to tell anyone it was you.”

“I won’t,” I assured him.

Chris handed me $25 in singles. “Just stay under the blanket, and I’ll call the guys over one by one.”

I lay down under the blanket, my heart racing with anticipation. Chris lifted the edge of the blanket and pulled down his pants, revealing a rigid, 7-inch cock. I started licking the head, and he rewarded me with clear pre-cum liquid. I sucked the head into my mouth, circling the crown with my tongue. I took the entire cock into my mouth, hitting the back of my throat. Chris grabbed my head, shoving it hard onto his cock as he climaxed, shooting a load directly into my stomach.

After Chris, I sucked the next guy, an uncut, soft 5-1/2-inch cock. He got hard quickly, and I slipped a finger under his balls and touched his asshole, playing with it. He blew his load before I could deep throat him. The third guy was black, with a perfectly formed, 7-inch cock. I sucked the head, worshipping a beautiful piece of human art. He lasted longer than the others, and I felt his first volume of cum hit the back of my throat. I engulfed the entire length, letting the rest of the huge amount of cum shoot into my stomach.

As the guys left, Chris pulled the blanket off me and helped me to my feet. I was a little stiff in the legs but none the worse for wear. He told me that some of the guys had asked if I would take care of them on the way back, maybe even give them a fuck for extra money.

“I’ll do it,” I said, thinking about the extra cash.

Chris smiled. “I’ll talk to the guys, and we’ll figure something out.”

The rest of the day was fantastic. I had enough money to enjoy all the rides I wanted, and I even had some left over. At lunchtime, Chris found me alone and said he’d figured something out. Three guys wanted blow jobs again, and three others wanted a fuck. He offered to pay me $5 each for the fucks, and he’d pay me $25 in total if I agreed.

“I’ll do it,” I said, thinking about the money.

Chris smiled and took me to a secluded area near the softball field. He coated his cock with butter and eased it into my asshole, asking how I felt. I told him I was uncomfortable at first but by the time he got his second finger in, it was feeling pretty good. He placed his greased cock head at my opening and started to press in, going slowly. When he was fully in, he paused, letting me get used to the feeling. He started to fuck me full strokes, and it started to feel fantastic. After about fifteen minutes, he plunged in deeper and shot a load deep into my ass.

He handed me a face tissue and told me to use it as a plug to keep the load of cum and butter in as lube for the other fucks. By my satisfied grin, he already knew I enjoyed myself and was going to earn the extra money on the trip back.

He gave me a couple of pats of butter and told me to re-lube my hole before the guys started to fuck me.

On the ferry ride back, Chris set up his deck chair and blanket in the same area as before. He told the guys not to start coming over until we got out into open water, giving me a chance to get under the blanket. I took off all my clothes and laid face down on the deck chair, covered by the blanket.

When the guys arrived, Chris made it clear that the guys who wanted blow jobs should go first, since they would shoot their loads the fastest. For the blow jobs, the guys sat on the deck chair as before, and I sucked them until they came. When it came time for the guys to fuck me, Chris made his instructions clear: “Before or when you get under the blanket, get your own cock hard and ‘she’ will place it at her hole so there would be no accidents entering the wrong opening.”

I laid face down, tucked my cock and balls under me, and made sure nothing could be seen from behind me. When the first guy got under the blanket, he was only 6 inches uncut. I had placed the extra butter at my hole when I removed the tissue and was glad I could feel Chris’ load still inside for the most part. He slipped into my hole in one push, and I clamped my internal muscle down hard to make my hole as tight as possible. He started to fuck me full strokes, trying to reach under me to grab my “breasts” that I slapped his hands away. He kept his hands on my hips until he plunged and shot a load deep into my ass.

As the black man’s 7-inch cock entered me, I felt a sense of relaxation wash over me. The two cocks I had taken beforehand had prepared me well, and I was more than ready to take on his added length.

He thrust in and out of me with ease, his experienced movements sending waves of pleasure through my body. I felt his load building up inside me, and when he finally came, it was a bigger release than I had expected.

The cum oozed out of my asshole and down my crack, coating my balls in its warm, sticky texture. I felt a sense of satisfaction wash over me, knowing that I had enjoyed every moment of it.

Just as the last guy was about to pull out, he shot again, this time barely getting past the entrance of my ass. I let him stay in, enjoying the feeling of his slippery load coating my insides.

Once he finally pulled out, Chris told his crew that he would meet them inside. As they left, he uncovered me and helped me get dressed, offering me his handkerchief to pad my briefs.

“I really enjoyed your blow job and ass fuck,” Chris said, smiling at me. “And our deal with the others made me look good. I hope we can keep it going later on.”

“I’d like that,” I replied, smiling back at him. “When we get back to school, maybe we can work something out.” I slipped his handkerchief into my pocket, determined to follow through on my promise.

Days later, I had the handkerchief washed, cleaned, and ironed, and slipped it to him in the hall. He smiled and nodded in appreciation, and I knew that our new friendship was off to a good start.

“Thanks for taking care of it,” he said, tucking the handkerchief into his pocket. “I’ll make sure to repay you… somehow.”

I smiled, knowing that our deal was far from over. But for now, it was enough to know that we had formed a connection, one that would last long after the day was over.