It started with a dare...

Like most of when we are young, we did things that at the time were crazy and exciting without any thoughts of the repercussions of our actions. I was definitely one of them. It started one day after school. My friend and I were seventeen walking back to his house from high school. It was only a few miles each way. We had planned to hang out at his house and play Atari for a bit then I would walk a few blocks to my house. We got to his house and his parents were fighting so I opted to not stay. As I was walking, a guy flagged me down from his front door and asked if I could help him move a dresser from his basement to the upstairs. I somewhat knew the guy, Paul, he had graduated a couple of years earlier from high school and now lived with his grandma. I agreed, dropped my backpack just inside his door and followed him to the basement. The basement was unfinished, concrete floors with a few pieces of mismatched carpet covering most of it. Paul had told me he needed the dresser moved into the garage because someone had bought it from his grandma. It was a challenge to get it up the narrow steps but we managed to not ding it up too much. After we got it into the garage, Paul asked me to follow him downstairs because he wanted me to see something. Not thinking too much about it, I said sure.

I followed him downstairs to his bedroom. His room was very messy. Clothes stacked in piles on the floor, food and trash laid around. His bed was on the floor, just a mattress with the sheets in disarray. He had a TV in his room with multiple VCRs connected to it. There was a stack of video tapes and he put one into the VCR. I sat down on his couch after moving some stuff off of it. Paul put the tape in and pushed play. I was completely stunned!! There was Paul laying naked on his bed. There was someone moving the camera because the picture was so jumpy. You could hear a man's voice. I couldn't take my eyes off of what I was watching. The man told Paul to masturbate. I watched Paul masturbate and cum onto himself. The man ran his fingers through the cum on Paul's body and made Paul suck it off. Then the video ended. I now was Paul differently. He must of seen my reaction. He must of noticed how erect I was because I was trying to cover up my excitement with my hands over my shorts. Without a word Paul unzipped his pants exposing himself to me. His dark hairy lean body, his long slender cock bounced upwards as it was filling up with blood. Paul gave me a moment to take it all in. I tried to look away as my cheeks flushed red but kept looking at his cock. Then he dared me to show him. I quickly said, "um, I better go. I am expected home soon." I backed away out the door.

As I turned Paul came up from behind me. I felt very weak as he turned me around. "I showed you now you show me." he said calmly as my heartrate began to thump in my ears. He stepped back away. I was facing Paul but froze. He gently stroked his cock. The throbbing in my shorts was immense! "I double dog dare you!" Paul smirked and followed up with, "You know what happens if you don't do it?" I was unfamiliar with the repercussions and shook my head no. "I get to put my dick in your ass." Paul said it smoothly. Thoughts of his cock in my ass seemed disturbing and arousing to me. I was very sheltered and had no idea that this was a thing but it made me so hard imagining how it would ever fit in me. I felt compelled and pulled both my shorts and underwear down. Paul wiped saliva from the corner of his mouth while stroking his cock with his right hand. With my shorts and underwear down around my ankles. Paul masturbated standing up. He looked at my smooth body, my cock was fully erect, I didn't have much for pubic hair and what I did was blonde. My cock was much thicker than his and almost as long. I admired Paul's cock as he jerked harder and harder. His breathing wee fast and he leaned over straining as he tugged on his rod. Cum erupted out of him as he shouted out. His cum struck me in the face, stinging my eyes. It splattered on my shirt and touched my bare legs. Paul kept jerking off until he had nothing left. His cock went limp quickly and swayed between his legs oozing onto the floor. I wiped the cum from my eyes but the burning made them burn. I smelled his cum on the back of my hand as I wiped my eyes. Tears began to run down my cheeks and I was now more embarrassed about crying than my exposed lower half of my body. I stepped back too far and fell backwards into the wall. By trying to catch myself, I had stepped one leg out of my shorts and planted it down as my other leg kicked up flinging my shorts and underwear across the room. Paul caught it. He separated my underwear from my shorts. Then he tosses my shorts back to me and kept hold of my underwear. I asked for my underwear back. Paul smirked and slipped my underwear on tempting me to pull them off of him. I was in a panicked state and slipped my shorts on. Then I bolted for the stairs as the doorbell rang. Paul didn't chase after me. I was surpused to see Paul's grandma coming down the steps to see what the commotion she had heard. She smiled briefly then turning around to go answer the door. I walked up behind her slowly with my head down. She blocked me as she answered the door making it awkward to grab my backpack. There was a guy there. His voice was familiar sounding like from the video I had just seen. Paul's grandma welcomed him in. He looked at me and I got this odd sensation of being undressed in his stare. He shifted his focus away from me. The guy had to be in his early thirties, he had dark hair, dark eyes, smelled of cigarettes, beard, average build and maybe 6'1" tall. Just then Paul came back upstairs fully dressed. Right in front of everyone, Paul said exasperated, "Grandma, he (meaning me) exposed himself to me!"

I felt all condemning eyes upon me and quickly shouted back, "No, fucking way!! Paul showed his cock to me and made me watch a video of him masturbating! !"" His grandma looked at me then at Paul. She knew her grandson too well and began to hit him calling him names. Paul backed away smiling at the plight he put me in. I was extremely embarrassed and somewhat relieved his grandma was on my side. Just then a hand was placed on shoulder,

"Come with me."the man said sternly. I was forced into the garage.

A flood of emotions came over me and I began to cry. As pathetic as I looked, I made a poor attempt to be strong by saying, "that was you in the video! Right??"

The man made a slight chuckle. He shook his head yes. Then looked at me pausing. He then made his pitch. "How long was that video you saw?" I didn't answer instead it was if he was talking to himself. "Was it three or four minutes tops!!??" Again I didn't have a chance to respond. "He made five bucks! What do you make working at that pizza place?" I froze in terror that he knew where I worked but reflecting now it was pretty easy since we lived in a small town. He went on comparing how much Paul made to me and stating how easy money it was. "What if I offered you double for the same video?" I was now shaking as I leaned on the dresser in the garage. Paul had joined us and overheard. His grandma was exhausted and needed to sit down in the living room. Still shouting at Paul. Paul was irrate! He began arguing with the man. I found my escape and rushed back into the house, grabbed my backpack, and ran home as fast as I could.

The next day after school my stepmom confronted me. Paul's grandma had called my stepmom and told what had happened an apologized for his actions. My stepmom, who never really warmed up to me, automatically convicted me of instigating the whole thing. She slapped me and called me a fagot before I retreated to my room. I hated her so much! When my dad had come home she took it out on him. I heard everything through the thin walls. My life was in pieces. I wanted to just run away.

So I did!!

The man I had met at Paul's house approached me while I was at work late one night. He had come in just before I had locked the doors. I was closing that night with an assistant manager when she got called away for an emergency. Which left me to clean up on my own. The man sat ordered a pizza. I made the pizza and waited on him like any normal customer. I cleaned while he ate in the dining area and checked in occasionally. I rung him up on the register, he paid , and left not saying a word at what had happened at Paul's. Then went back to the table and he left me a huge tip!! It drove me mad, I had anticipated he might say something but he didn't, I had played what I would say in my head but never got a chance, I fantasized about his offer but he never pursued. I was infuriated at how cool he was and needed to know why. I went outside and approached him. I asked him why the big tip as if he was trying to entice me with money (which it worked). He smiled, which only ticked me off more at how calm he was, and politely told me since he came in just before close he appreciated the service and wanted to express that with a nice tip. I was totally taken aback and thanked him. I lingered for a moment and asked if his offer still stood. The man looked at me and asked what offer. Puzzled, I timidly told him about the money for doing a masturbating video for him. He looked at me stone faced and acted as if he had never said it. He then looked around and noticed we were the only two in the parking lot. Then he quietly asked if I would be willing to talk after I got done working. He waited in the parking lot and gave me a ride to his place.

I was very nervous and somewhat aroused while driving to his farm house about ten miles out of two. It was an unassuming three bedroom ranch house. We sat in the kitchen where he offered me a drink. We sat down and he just wanted to know my situation. Somehow he got me to open up about everything. By the end, he (Wayne), offered me a room to live with him rent free if I did chores for him. He had a contract that I briefly looked at and signed. He also gave me keys to a rusted out camaro to drive! I moved in just two days later.

At first it was pretty normal. Mowing the lawn, washing dishes, cleaning, and taking out the trash. I was still going to school and was questioned how I had gotten a car. But that changed on my eighteenth birthday. I worked the night before and had gotten back to Wayne's house just after 11pm. I had taken a shower, got a glass of water, and was in bed when just after midnight Wayne came into my room. He asked me to get up and follow him into the barn. It was an old barn, there were two tractors that didn't run, tools, and a bunch of junk in there. The light was on as we approached it. We walked in and there was this older guy standing there naked. He looked Hispanic, tan, muscular, had a goatee, tattoos, smooth, with a tiny cut cock compared to his stocky build. Wayne told me to take off my sweatpants and T-shirt. Wayne walked over and got a video recorder from a shelf. He started tapping.

I stood there naked as the man approached me. He touched my bare skin. I stood there shaking nervously as Wayne instructed the man to suck my cock. It was unlike anything I had experienced. He sucked me so well, that I almost fell over on him. I had to brace myself on his strong broad shoulders. The rush was intense! I made sounds that I had never made before. He slurped on me and it felt like he would swallow me whole. The guy was so good. Wayne instructed him to stop and we walked over to a steel workbench. I was told to sit on it. The cool metal touching my flesh made me shiver. The man moved up to me. He kissed me and at first I didn't really kiss him back. His body moved up between my legs and I felt him against me. He passionately sucked on my neck and ears which made me weak. Soon our hands were all over each other. I began to kiss him back. In the heat of the moment, he lifted both my legs up onto his shoulders, my back was pressed up against the wall, he stuffed fingers into my ass. I cried out in incredible pain!! I begged for him to stop but he didn't. He pressed his body up between my trembling legs keeping me in check. His fingers dug into my dirty ass hole. Tears ran down my face as I pleaded for it to stop. Wayne told me to relax as I tried to push his fingers out of my ass. I couldn't stop fighting. "It will only hurt more if you fight it" the man said in his accent as coolly as he could. I wasn't physically able to move him. The fingering eventually stopped and he took his tiny cock into me. I tried to repel him as best as I could. There was like this popping sensation, I think there was a sound too, when penetrated into me. I let out this strange ughnn sound as my head flung forward over the man's shoulders. Drool ran out of my mouth. I made a sound every time he pushed deeper into me. He felt massive! I struggled to breath taking in large breaths everytime he pulled back outwards. The pace quickened! I took short quick breaths in between my moaning. My ass was burning hotter and hotter, my legs were now numb. My hard cock slapped between the man's body and my own. He went quicker. The sensations of his flesh entering my ass was overwhelming, I no longer begged for it to stop as I struggled to keep from blacking out. Just as my vision was eluding me, my body went into a seizure like state as I began to erupt cum from my cock. It just sprang out of me involuntarily! It went everywhere over us as my whole body shook. The man pulled out making me shoot one more good load out. I made this unholy sound as he jerked himself into me. His cum was not nearly as explosive as mine, it oozed slowly out of his tip. He rubbed as much as he could while grunting. When he backed away, my numb legs were unable to help me from slumping over. A feverish sweat came over me. The man thanked me, got dressed and left the barn out the back way. Wayne came over to me and had me show off my newly formed gape. Then he turned it off. He congratulated me on my birthday.

I did not got to school the next two days from the aftermath of what had taken place. I was told it would get better the next time.....