When I was fifteen or o I was petty much a hell raiser, my two step brothers, Chris who was fourteen and Brian who was sixteen were pretty much under control, so my step father saw that I needed guidance and discipline.
My step fathr was strict but fair, usually. He treated us all the same, which meant when we stepped out of line we'd end up over his knee with our jeans and underwear at our ankles. He'd usually only use his hand, and that was enough. He seemed to have a gift of making sound contact with bare skin and making it hurt like hell. He'd always finish up a spanking with using one hand to spread out but cheeks, and the other to spank the inner most part and our butt holes. These were always public spankings, to anyone who was around (meaning family and friends). I most cases, on days when we messed up, at dinner we'd be told to go up and shower. We all knew that meant take a shower and clean every inch of our bodies and come out with only a towel around our waist.
We have to wait in our bed room, we all shared one bid attic room. My step father would come in and have us remove the towel and stand there naked while he'd go on and on about what we did. He'd usually sit on the end of the bed and pull us over his knee. Needless to say, that we always slept on our stomachs after getting a spanking.
My step father was at wits end when the police brought me homw again after breaking into someone's house with some friends, and this time I really though I'd have to go to jail and was pretty _d_a_m_n_ scared. My mom was away for a week or so, so it was just us guys.
My step father just looked at me and told me to go up and take a shower, and I heard him talking with the cop while I went up the stairs. I waited in my bedroom for awhile with the towel around my waist, knowing that this was going to hurt like hell, but more afraid of jail.
After an hour or so of painfully waiting, my Brian came up and told me his dad wanted me down in the family room. This was very differet than usualy, and made me even more nervous.
Downstairs, Chris and his dad were waiting, Brian sat down next to Chris on the couch and my step father anounced that since spanking alone hasn't done a _d_a_m_n_ thing to change my behavior, he'd have to give me a taste of what jail would be like. That I'd accept the punishment he was going to give me or he'd call the police and they'd arrest me, period.
He put a video tape into the player and turned it on, I was told to just stand there a watch. It was a scared straight tape or something the cop had lent him, with guys telling what it was like in jail, with the jail house _s_e_x_ and everything. A few months before Chris, Brian and me had started jerking off together and sometimes giving each other hand jobs, nothing like what happens in jail.
After the tape, my step father asks what's it going to be, the police or his punishment. Not knowing what he was going to do, but knowing that jail had to be worse, I choose his punishment.
Things moved fast from there, he grabbed my arm ad led me to the chair, pulled off my towel and told me to bend over and grab the arms of the chair and not to let do.
"First, thing they do to you in jail is a body cavity search" he instructed as he pulled on a rubber glove ad got out a tube of KY jelly, my stomach dropped and I knew this wasn't going to be fun. He lubed his finger, spread my butt cheeks and pushed his finger into my ass forcing me to moan in pain (which turned into pleasure after about 30 seconds). He took his time, moving his finger around, pushing it as deep as he could. I could see Chris and Brian both getting tents in their shorts as they watched.
He janked his finger out suddenly and pulled me over with him to the couch, he pulled me over his knee and started to beat my ass harder than he ever did before. "Getting beat up in jail isn't quite like this, but pain is part of the first day". He spanked me over and over again for what seemed like an hour, twice he pulled my cheeks apart to spank my butt hole. The first time he pulle them apart with both hand and said "nice little pussy" to Chris and Brian, and as I looked back over my should I could see them smile and then they started to crack some weird jokes.
With my ass on fire he pushed me off his knee, with me landing on the floor. All three of them could see my almost hard _c_o_c_k_ as I lay there on the floor with my ass burning.
"OK, now the fun part of jail life, we'll skip over the shower room part till later" he mocked as he grabbed my arm and pulled me over towards Brian, pushing me down onto the floor infront of him, Brian kinda smilling abit. I was kneeling almost between Brian's legs as he sat on the couch. "OK, you're going to do what you're told boy, or else you can do this for real in jail, Brian and Chris are in charge, I'll be back in about a hour". He said as he headed out the door.
Brian looked right at me as he slid his short down, his hard _c_o_c_k_ popping out. "SUCK IT" was all he said. I knew I didn't have a choice, I moved slowly towards it and he grabbed my head and guided my mouth over his _c_o_c_k_. It was my first time, and his dick felt bigger in my mouth than it used to in my hand. I sucked, and sucked and sucked, and found that I was enjoying it. Quickly he pulled my off it and said he was too close to cumming, needed to save that for the other end.
I looked over, Chris already had his _c_o_c_k_ out and was rubbing his balls, "I'm next" he said. Brian directed my head over to Chris's _c_o_c_k_ and I eagerly sucked him. It didn't take long for him to shoot his load in my mouth, he held my head down even though I wanted to suck every last drop, not believing how good his cum tasted.
"Wait here" Brian told me, Chris said he was going upstairs to take a shower. Brian came back into the room, hold a good size carrot he got from the kitchen. "Bend over" he said and I got scared, but I did as I was told and bent over again and held the arms of the chair, I head the cap to the KY open and knew what he was about to do. "SPREAD EM" he demanded, so I reached back and spread my butt cheeks, giving him full access to what he wanted.
He push the carrot slowly up my ass, making me moan. When it was in a bit he stopped and reached around and grabbed my _c_o_c_k_. "Glad you like it" he said, as my _c_o_c_k_ was hard as concrete, and he pushed the carrot even farther up my ass.
"Stand up, get upstairs, make sure it doesn't come out" I walked slowly upstairs as the carrot filled my asshole, stretching it and preparing it for what was to come.
Up stairs, Chris was coming out of the shower, he kept the towel around his waste and Brian said he's going in for a shower too, for me to come with him. We both got into the shower and he ordered me to wash him completely. I lather every part of his body, cleaning his _c_o_c_k_ and ass completely.
After our shower, I was allowed to remove the carrot from my ass and was told to make sure Chris had cleaned his ass well enough in the shower. No really knowing what I meant, I had hesitated a minute too long. Brian gabbed me by the arm an bente over the end of the bed, he took a belt from the closet and whipped my ass three times. "Now, go over and use your tongue to make sure his asshole is nice and clean".
Chris moved over to his bed as I approached him and layed face down, spreading his legs. I moved over him, spread his butt cheeks and began tongue his hairless asshole. I quickly got up and reported that it was clean, only to betold to my tongue back there and make _d_a_m_n_ sure. Doing what I was told I continued to rim Chris until I was told to stop, Chris moaning and moving slightly to adjust his _c_o_c_k_ the whole time. Chris rolled over, and told me to suck him again. His _c_o_c_k_ was completely hard, and though it took a few minutes longer this time, it wasn't long before he filled my mouth with another load of cum. I swalled every drop and continued to suck him until Brian pulled me off.
Brian threw me down onto my bed and told me to roll over, I had no doubt what was to happen. I heard the top of the KY click open again and knew that this time Brian was greasing up his _c_o_c_k_. A minute later I felt him pressing it into my ass, like a guided missile he entered me and pushed into quickly. I moaned in a combinating of pain and pleasure, which turned to all pleasure as he began to pump his _c_o_c_k_ in my ass. He seemed to know what he was doing, and lasted for what seemed like a long time before I felt him shoot his load up my ass. He pushd deep into me as he came, and held himself there for a bit after he came.
He got up, I was laying there with my as still bright red, but now well _f_u_c_k_ed as my step father came into the room. "How'd you like your first day in our jail?" he quipped. Guys, his is going to be a fun week he joked with Chris and Brian and I knew it would be.