20 years ago, I guess you would have called me a player. I was young, fairly good looking, self employed as an artist with a long list of clients, and lived in a great condo on the near north side of Chicago over looking lake Michigan. I dated a steady bevy of beautiful women, almost all of whom, wound up in my bed. Life was good.
As time goes by though, we mature and eventually I wanted to move from the hustle and bustle of city life. My art, these days, had grown into a lucrative website design business and that I could do from anywhere so, after 20 years of living in the city, I decided to find a nice, little place in the country. After 3 months of looking I found the perfect spot. Just 45 minutes southwest of the city, set on a quiet, rural road on a couple acres of wooded property.
As soon as I got settled I started walking in the evenings. Walking was my favorite work out and it kept me slim and trim. It had become a ritual of mine. I’d been walking every evening for the last several years. In fact, taking a long walk in the evening was one of the factors that led to my decision to move. I just didn’t feel safe walking in downtown Chicago anymore. The road I lived on, though extremely dark, was, otherwise, perfect for walking. I had measured it. From my house to the end of the road and back was just over 4 miles. Since there were only 6 houses on that whole stretch of road, it was very quiet and peaceful.
The only fly in the ointment, was a jack-ass kid who lived up the street with his parents. I got the low down on him from a neighbor just after I had moved in. It seems no one in the neighborhood liked him. A tall, strong kid of 19 or 20, he and his 5 or 6 buddies, pretty much, terrorized the area with their hot rods, driving up and down the road at 70 and 80 mph. It seemed everyone in the neighborhood was afraid to challenge him in any way so he did what ever he wanted. Even his parents were, either afraid of him themselves, or just didn’t care what he did. The only good thing was his younger sister. A beautiful blond with the body of an angel. My guess was that she was 16 or 17 years old. I would see her sunbathing in their back yard sometimes. I maybe 43 years old, but I still love looking at gorgeous, young ladies.
On several occasions, Jake, that’s the jack-asses name, and I tangled. Several times I screamed at the top of my lungs as he drove his souped up Mustang by me like we were at the Indy 500. I called the cops a few times, only to be told they couldn’t do anything unless they saw him themselves. I made no secret of the fact that I had called them and vowed to continue calling the cops until I got results.
On one particular beautiful evening, several months ago, I decided to double my walk. The sky was clear and I could actually see the stars now that I was in the county. As I walked past the home of my nemesis, I saw the garage door was open and Jack and several of his buddies were inside drinking beer and being their vulgar selves. I kept walking to the end of the road, then turned and started back. This time, as I approached the house, Jack and his buddies were standing at the side of the road with an extra beer.
“Hey man,” said Jack, “have a beer with us.”
“No thanks,” I said, as I continued to walk by.
“Ah come one, no hard feelings. I don’t want to keep fighting, we’re neighbors.” Jake’s words seemed to be sincere. Well, this looks promising, I thought. Threatening to call the cops certainly didn’t help, maybe I can get him to slow down by using some strategy. Had I known his parents were on a two week vacation and Jack and his sister were home alone, I may have reconsidered, I’m not sure. Jack and his friends were all smiles as he stretched out his hand to offer me the open beer.
“Okay, thanks,” I said as took the beer and started to bring the bottle to my lips. As I tilted back my head and put my mouth around the opening, I immediately realized the liquid in the bottle was not beer. I had never tasted piss before, but from the smell and the taste, I was sure they had pissed in the bottle. I could hear the guys laughing as I spit the foul stuff in the lawn. “You bast,” before I could get the rest of my cursing out of my mouth, I felt a sharp blow to the right side of my face and stumbled backwards, right into one of the other guys who grabbed my arms and pulled them behind me. Before I could get out another word, Jack lunged forward with his knee and caught me perfectly, right in the crotch. I immediately saw stars. The pain was intense. I tried to double over to relieve some of it, but Jack’s friend still had my arms pinned behind me and kept pulling me up. My body broke out in a cold sweat and I was fighting to keep from going unconscious. I could feel Jake squeezing my cheeks together and forcing the bottle in my mouth, but I couldn’t do much about it.
“Are you refusing our hospitality?” he asked as he forced the piss down my throat. I tried to move my head to keep from drinking but someone grabbed my hair from behind and held it in place. I tried to spit it out but they forced me to swallow about half the bottle. I was still in excruciating pain. I was hoping, now that they made me drink their piss, that they would let me go, but no such luck. I could feel someone undoing my belt and pulling my pants and underpants down to my ankles. I felt the cool, night air caressing my sore privates. I was still in a fog as I felt a guy under each arm drag me down the drive and into the garage. I could hear the garage door going down as they dropped me on the cold, concrete floor. The pain from Jake’s knee was finally starting to subside. As someone started to remove my shoes I tried kicking and fighting back, but I was no match for all of these young, strong men. They subdued me with little effort. Jake was giving orders to rip my shirt off and take off my shoes, socks, pants, and underpants. In no time I was laying there completely naked.
Jake was kneeling on my back keeping me on my stomach while someone else had a hold of my hair again.
“Hey, Pete,” Jake barked, “in the corner, on the second shelf over there, there’s some duct tape. Grab it and bring here.” Peter came right over with the tape. “Now, tape up his hands real good.” I struggled but to no avail. In a moment my hands were helpless to me. “Johnny,” I heard Jake’s voice again, “get me one of the ping pong paddles from the basement.”
“Will do,” was the return. I was absolutely helpless now. I was totally naked with my hands securely taped together and several young, strong, guys surrounding me with, who knows what, in their minds. In just a couple of minutes Johnny was back with the ping pong paddle.
“Okay guys,” Jake said as he sat down on a metal folding chair, “pick him up and put over my lap and hold good.” I was starting to get the idea. Jake was going to paddle me. I couldn’t believe it was happening even as the guys picked me up and laid me across Jake’s lap. Suddenly I felt the sting of the paddle just as I heard the loud creak from it hitting my bare skin. I tried to jump off his lap, but I was being held in place. I could hear the other guys laughing. Again the paddle came violently down on my butt cheek and again and again. I was screaming for mercy but none was coming, just more of the same. Try as I did to keep from crying from the brutal beating I was receiving, I just couldn’t help it anymore and tears started to cascade down my cheeks. Suddenly, from the direction of the door between the house and the garage, I heard a female voice.
“Hey, what’s going on?” It was Jake’s younger sister. She was standing there witnessing my humiliation.
“This is our new neighbor,” Jake answered, “you know, the ass hole who called the cops on me.”
“The guy that’s always peeping at me in the back yard? Hey, can I have a couple of cracks at him?”
“Sure, come on over.” I could see her coming closer out of the corner of my teary eye. Just then several more quick, hard blows. Again I cried out and more tears streamed down my face. “Now aren’t you sorry you were peeping at my sister?” Jake asked sarcastically. “I think you should tell her you’re sorry, don’t you?”
“Yes, I’m sorry, “ I managed to get out through my sniffles.
“You’re sorry what,” again Jake taunting me with his voice.
“I’m sorry I was peeping at you,” I cried. I felt a couple more whacks and squirmed again trying to get some relief.
“I better not ever see you looking at me again, you hear me,” she said just as she delivered the last of her blows.
“Yes, yes I hear you.”
“You ever going to call the cops on me again?” I heard Jake ask.
“No, I swear, I’ll never call the cops again, I promise.” Jake pushed me off his lap and back on to the cold garage floor. Again I hoped this would be the end of my debasement. I prayed it would end, but had no idea how I could go on living on this street after this. Little did I know, the worst was still to come, much worst.
“Jeez Jake, what are you doing?” I heard from one of Jakes friends.
“I’m going to make him my bitch,” answered Jake. Just then I felt my legs being kicked apart and suddenly I felt Jake laying on top of me. I could feel the weight of his body pressing mine more firmly onto the floor. Jake reached up with his left hand and grabbed the back of my hair pulling my head backward, then I felt the most horrifying feeling of my life as Jake stuck his finger up my butt. “How does that feel my little cunt?” There was a new evil tone in Jake’s voice. I could hardly speak with my head pulled back.
“Oh please, please don’t. I promise, I’ll never bother you again, never,” I begged.
Jake rammed his finger in and out of my anus rapidly. It was then that I realized what the other guy meant when he asked Jake what he was doing. I could feel Jake’s bare skin. He had pulled his pants down and was now laying on top of me. Jake leaned in close. I could feel his breath just an inch from my left ear.
“Ready to become my bitch,” he whispered. I was terrified. I couldn’t see, but I felt his prick and balls between my legs. I didn’t have a homosexual bone in my body. I never had a homosexual thought and now, here I was, naked in front of a bunch of guys about to be fucked in the ass. My mind was in turmoil and I couldn’t comprehend what was happening until I heard Jake grunt and felt the extreme pain as he forced himself inside of me. It felt like someone pushing a hot poker inside me. I screamed, both from the pain and from a sense of the worst shame I’d ever felt. Again Jake grunted as he pushed himself deeper into my rectum. The cold, hard cement floor was scraping my skin as I felt him pull back a little then push as hard as he could sending his entire cock far inside of me. I felt his balls hitting my own. Somewhere in the back ground, I could hear the other guys cheering him on. Then I heard his sister laughing, I had forgotten about her. She was standing there watching the whole thing. I could hear some of the other guys yelling.
“I’m next,” I could hear them call. I knew this was not the end of my raping, but probably only the beginning. The pain from Jake’s, on going, rape of my ass was starting to diminish a little, but I knew the shame would never go away. Jake’s thrusts were getting faster and harder. I knew it was just a matter of time before he would climax. Just then it happened. I could feel his cock twitching as it fired shot after shot of hot cum far up my ass. Finally, I felt his sweaty body collapse on top of me and I could hear his heavy breathing. After a minute Jake started to get up.
“Who’s next,” he said.
“Not me,” I heard one of say. I got a faint glimmer of hope that Jake might be my only rapist.
“What’s the matter, Larry,” Jake said. “Hell, you’ve got the biggest cock of us all, you have to fuck him.”
“Not with you sister standing there watching me, I’m not.”
“Well I’m not shy,” I heard another voice say. I heard a zipper go down and I could see feet coming in my direction. I could hear him pulling his pants down. He lowered himself in place and I felt him adjusting his cock at the opening of my ravaged ass hole. He laid on my back and put his hands on my shoulders. Then, with out any more warning, pushed back on my shoulders as he pushed himself up, all the way in, in one motion, and my second rape was in progress. I couldn’t help but grunt with every thrust. My tears mixed with the sweat coming from my forehead. It seemed like an eternity before the second guy started to cum. Finally, for the second time, I felt his hot seed bury itself deep in my rectum. He lifted himself off of my back and immediately another body took his place. As I laid there with my third rapist busy at work, I could hear Jake trying to convince Larry to take his turn.
“I’ll fuck him if she goes in the house,” Larry said.
“Okay, sis, you heard him.”
“That’s not fair,” I heard from the female voice. “I’ve seen my share of cocks, Larry, yours can’t be that special.”
“I don’t care, Jenny, I not going to pull it out and fuck some guy in the ass in front of you.”
“Come on, Sis, in the house,” Jake’s voice sounding more stern this time. I heard the door shut behind her and now new that Larry was going to take his turn in my ass as well. As my third rapist finished I heard one of the other guys.
“Damn, look at the size of that thing.”
“Now you know why I wanted to make sure Larry took his turn,” I heard Jake say. I couldn’t move. I was not only exhausted, but I was so full of shame that I didn’t even feel human anymore. I felt someone kick my legs further apart and assumed it was Larry. He took his place behind me and, with little effort, rammed his huge cock into my well lubricated ass. As new sense of pain riddled my body. He must be enormous I thought as I dealt with my anus being stretched to conform. Finally it was over. I could feel copious amounts of cum oozing from my grotesquely stretched anus. I laid there, completely unable to move. I could hear Jake and his buddies, now dressed again, drinking beer and laughing hysterically. This I heard Jenny’s voice again.
“Hey guys, can I play too.” I heard them all break into new levels of laughter.
“Sure,” said Jake, “go to it.” I could hear Jenny’s foot steps coming closer. Then I felt something cold at my back door opening. It was big with a rounded tip. I guessed Jenny had a cucumber from the refrigerator. With no more ceremony, she pushed it in. It was even bigger than Larry’s cock and again, my anus was stretched beyond it’s limits. I cried out in pain again to the amusement of everyone, including Jenny as she rapidly fucked me for, what seemed like hours, while laughing the whole time.