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Really Bad Decisions


Guest ericbb99

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Guest ericbb99

(Part 😎

The next time I heard from him was mid-morning. I was in class. He texted me. Didn't know he had my number either. Fuck.

"I've been thinking about you. You're going to be fun," he said. I asked him how many bets were left. He replied, "Saturday is going to be a rough day for you. First, you didn't hit that homerun we talked about, so you get throat raped. Then, you couldn't get me off with that pretty mouth of yours, so I'm going to whore out your throat to my friends too. You couldn't even get me off when I gave you more time. Worthless slut. So condoms are off the table if I get to fuck you." I imagined he was laughing as he wrote it. He continued, "The dice came up even, so you have to come with me to the bath house. And you only managed to cum 11 times the next day, so you get whipped with the belt 39 times. The way I count, that's three down, three wagers to go."

"That's five," I protested. He replied, "No, the extra time on the blowjob doesn't count. You shouldn't have needed it, boy. That's on you. And neither does the dice. You didn't roll it, I did. That's on you too." I thought about arguing, but he followed it up by sending me the screenshot with my pics and videos and my dad's email in the address line. "Yes sir," I said. "Good boy," was all I heard back.

Later that day, he texted me. "You're coming to the Rangers game with me tonight," he said, "Meet me at the home plate entrance at 7:00pm. Don't be late or I might open my email and start sending drafts."

I scrambled to change my evening around, and managed to make it work. I met him and followed him through security. I loved looking at his muscular legs and hot butt as I walked behind him. He was wearing athletic shorts and a Rangers t-shirt. I was in the same. 

They seemed to know him everywhere we went, but he never introduced me. He just let me follow him around like a puppy while he talked to everyone. Clearly he was here all the time. And I was starting to think he was someone important. Then, he got us two beers and we went to our seats. I said I wasn't old enough to drink, but the look I got in return told me I better drink up.

Holy shit, the seats... fourth row, right behind home plate. Fuck, they must have cost a fortune. It was a Yankees night too, and the stands were pretty full. It was clear he had money.

We sat down and he rubbed my leg. I'd never had a man touch me before in public, and it was electric. I was scared. I was anxious. And I was so turned on. He looked over and said, "Here's the big one. This bet is going to be fair too. It's too big not to be. If the Rangers win tonight, I'll settle for a blowjob. But if they lose, so do you. And I get your ass." I gulped and the game started.

We watched without talking much. He knew how scared I was and I think he liked it. He didn't want me to get too comfortable.

It became clear quickly that the Rangers were going to lose. By the fourth inning, it was 8-0. I started to panic. "This doesn't look good for me," I said. He just chuckled and kept watching the game. I had to think fast, "How about this... I'm clearly going to get fucked," I whispered as discreetly as I could, and continued, "If the Rangers lost by 6 points or fewer, you have to use a condom." He looked over at me as if to say, 'That's not going to happen.' So I continued, "But if they lose by 7 or more points..." I trailed off, and he finished my sentence, "...no lube for you. And I'm going to rape you." He wasn't whispering and he wasn't quiet. I turned bright red. He continued, "I'm going to destroy you. Slap you around, choke you until you pass out, and tear your little virgin rape hole apart. Deal?"

I thought for a minute, and replied, "Deal."

The innings went quickly. Rangers scored three in the 6th. 8-3. And in the top of the 9th, the Yankees scored four. 12-3. It was all down to the next half inning. And the Rangers choked. Michael laughed as I got up, and he slapped my ass as I walked up the stairs. "You're going to regret this," was all he said. Then he walked to his car, and I walked to mine. I cried most of the way home. But my dick was hard as a rock.

Two more wagers to go.

(to be continued...)

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Guest ericbb99

(Part 9)

That was Thiursday night. I expected to hear from him in the morning. But nothing. No texts, Grindr messages, or emails all day. I was weirdly disappointed.

Around 9pm, I still hadn't heard anything. I'd been wanting to see the Ant Man and the Wasp movie, so I texted a few freinds, but no one was free. So I decided to just go on my own. After all, Michael wasn't going to text at that point. I left my dorm room in jeans and a white t-shirt and some leather flip flops. Nothing fancy, but I was going on my own after all.

I got to the theater, parked, got my ticket and a Dr. Pepper, and found a seat. The movie started at 10:30, and I was a few minutes late, so I had to sneak in in the dark, but I managed to get a good seat close to the middle. A minute after I sat down, someone came up and sat next to me. I thought it was a little bit weird, since there were lots of seats around me. But I just ignored him. Until he reached over and grabbed my far cheek and pulled me in for a kiss. I was shocked. It was Michael. How did he even know where I was?

"What the hell?" I whispered to him. He just smiled back at me with his evil grin and pulled me in again. His tongue was talented. He bit my lip, and made out with me. I felt his stubble brush against my lips as he kissed my neck. He definitely took charge, and I liked it. Eventually, I pushed away and reminded him we were in the middle of a busy theater. Then he got an idea.

He whispered in my ear, "Unbutton your jeans." I almost yelled at him. "No fucking way," I exclaimed. "Unbotton your fucking jeans," he replied angrily. I was afraid. I undid the top button, and he unzipped them the rest of the way. He pulled my dick out right in the middle of the dark movie theater, and he played with my balls and got me rock hard. Then he whispered in my ear, "Don't make a fucking sound. If I hear even the tiniest peep out of you, you have to let me lock you in a sling tomorrow night so you can't get away. But if I can make you cum without making a sound, you win."

Then he started stroking my dick. At first, it wasn't difficult to keep quiet, but then he spit on his hand and started going harder. Fuck it was hot. And I was usually loud when I came. So I decided not to let him make me cum. I thought about anything and everything except what was going on but it was no use. As hard as I tried, he had me on the edge, about to cry out. But I was determined.

Then, almost out of nowhere, it built quickly, and I couldn't stop it anymore. As I bucked, I could see him laugh at me, and I came all over that white shirt I wore. I cried out, briefly, but definitely. It was more of a moan, really, or maybe a grunt. Or maybe all of the above. I just know I made noise.

I leaned in for another kiss, but he got up and walked out. After he did, I licked the cum off my shirt. And I looked around me. Only one person had moved farther away from me. I wasn't sure whether or not anyone else knew what had just happened. But if they did, they knew what I slut I was.

(to be continued...)

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Guest ericbb99

(Part 10)

I had to walk out of the theater with wet cum spots all over my shirt. The theater was probably a quarter full that night--not a ton of people. But I have to think a handful of them knew what had happened. I was red in the face as I walked out. I was so embarrassed. And how the fuck had he found me anyway? There was something incredibly terrifying about him stalking me like that. But I was turned on and I didn't care. This whole thing had just been a series of bad decisions. No point in stopping now.

I got home and checked messages. He sent me one about how much he liked kissing me. If I'm being honest, I fucking loved the kissing too. There was something so erotic about my mouth meeting his--his stubble, the roughness and dominance--but also so much softness, a gentle intimacy. It was intoxicating. This was all so new to me. I fell asleep that night thinking about it.

The next morning, I woke up and went about my normal Saturday routine. I went to the gym with some baseball buddies of mine. We had a pretty hard workout and decided to go sit in the steam room for a while. The towels came off and we made our way to the steamy benches. All the eyes in the gym were on us. Four hot-as-fuck naked 18 and 19 year olds in the steam room, beads of condensation and sweat dripping down our chiseled abs. I had never thought about how sexy we were before, to be honest. I'd never noticed the eyes following us. Michael was changing the way I saw the world. But people definitely were watching us. And I kind of liked showing off.

The problem was, I started to get a chub sitting in the steam room. I excused myself and jumped in the shower and jerked off. I let out a little grunt at the end, but did my best to keep it quiet. I threw my towel back on and flung back the curtain. There was a guy just standing there in front of my shower stall, naked. Hot, probably mid-40's, some greys starting to come in up top, but sexy as fuck. I made a quick glance down at his dick, but tried to disguise it as wiping my face. He was hung, that's for sure. And some serious girth too. And he had a tattoo above his cock. A biohazard symbol. What a weird tattoo. And what a weird placement. I had no idea what it meant. "Excuse me," I said, trying to get by him. He smiled and stepped aside. I got dressed and my buddies and I went to breakfast.

Our server at the diner we went to was our age. I think I'd seen him around campus too. I'd never noticed before, but he definitely looked gay. Kind of twinky. A short fade like my hair, but long on top. Tattoos. I didn't know I had gaydar, but it was going off. He seemed to pay a lot of attention to me. I laughed a lot and acted a little bit flirty. But I couldn't go too far. My friends were with me. I commented on his tattoos. He had a rose down his forearm that was really hot. "My favorite is on my thigh," he said. "A scorpion." I replied, "Cool," not really knowing what it meant.

My whole day was like that. It was a brave new world. I still wasn't out, but I was noticing guys in a way I'd never really done before. And they were noticing me. Or, maybe I was just paying attention for the first time. I didn't really know, but it felt good. I flirted with half a dozen more guys that day--at the mall, around campus, and on Grindr. I was on fire. I liked it.

I had one stop I had to make. I ran up to my dad's house. He wasn't home, so I let myself in and went back to his closet. I knew if I forgot to bring the belt, I'd be in trouble. My father had an extensive and well organized closet and a lot of belts. I ran my hands across the leather of a few. Michael had said he wanted the biggest and thickest one so I found it, rolled it up, and slipped it in my pocket. It was going to hurt for sure. That part I was not looking forward to. Honestly, there wasn't much about the events to come that I was looking forward to. And yet, somehow, I still got hard every time I thought about it. It was strange, and I didn't understand it.

I got back to my dorm room and stripped and laid on my bed and opened my phone. He had texted me, "Wear a jock strap tonight. I don't care what else you wear. It'll get torn off pretty fast anyway." Then he added, "Oh, and make sure you clean out. If you don't know how, watch a video online. You're going to clean my dick off with your mouth when I'm done fucking you, so you better be sure you do a good job." I didn't know how, so I found a video and got to work. Then I put my jock strap on and laid back down. It was about 7pm at this point. He texted again, "And don't you dare think about touching your dick. You don't get to cum tonight until I say so. IF I say so." I stopped touching myself.

I was waiting for the last bet, but he never sent it. So I messaged him around 8pm, "There's still one bet left, right?" "Oh, we'll do that one in person," he replied. "Meet me at Club Dallas at 10pm", he said, and he gave me the address. Around 9:30pm, I got a text, "Don't you dare think about flaking. I will ruin your fucking life, you worthless whore." If I was being honest, I had been thinking about backing out. I messaged him again, "Please don't do this to me." I was getting nervous, almost in tears. I had a history with some anxiety, and I could feel a panic attack coming on. He replied back, "You'll be there... or your father, your coach, your whole baseball team, all of your friends, and tons of [banned word] on the internet will find out what a worthless rapetoy you really are. Don't fuck with me, boy. 10pm is not a request." And he logged off.

(to be continued...)

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