--------------Chapter 19--------------------
***Normal cautions apply up front. This story contains sexual content including some underage content that may be offensive. If you're offended by man to man sex, BDSM and other similar topics, this isn't the story for you. If you are underage in your area to read this, don't read it. There may be unsafe sex described in this story...be smart in the real world and make good choices.
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------------From Chapter 18---------------
"Amazing Josh, fucking amazing" Jorge said as he stepped back into the dark.
As usual, my heart leapt at pleasing Jorge.
"Well done Josh. Now we go and fuck" Franco said.
To say I was happy at the idea of getting fucked by this Italian stud would be putting it mildly.
------------Chapter 19--------------- "I can't believe we made it!" Kyle said as we high-fived. "Yeah, we're free of high school!" I yelled as I threw my cap in the air for the fourth or fifth time since the ceremony wrapped up.
"You guys get together for a picture" my mom said for about the hundredth time today.
"Mom" I said, trying to sound exasperated, but happily grabbed Kyle around the neck and hammed it up.
"Remember you need to show up at the party at the house before you and Kyle head off to the lake" mom said.
"Yeah, we'll be there" I said.
Kyle and his parents, Jorge, Malcolm, Austin and Cameron were all going to be at the house along with other family and friends.
Last night, before graduation, I had sat my mom down and told her that I was gay. I also told her how much Eric had helped me find my true self. I was nervous about how she would take it but shouldn't have been.
"Josh, you're my son and I want you to be happy. Be who you are. Make good choices and be safe but don't let this town define you as something that won't make you happy" my mom had said.
I hugged my mom and cried for the first time in a long time. I don't know why I ever thought she'd be any other way.
The party at our house was great. Mom and Eric had gone all out to decorate, setup a DJ, hired catering and had a fully stocked bar. There was a present from my dad. A very nice new MacBook with all the bells and whistles. There was a card with it that basically told me, in nicer words, that he was too busy banging his latest piece of tail to be bothered coming to my graduation.
Kyle looked over my shoulder as I opened the present and read the card. "Josh, I'm sorry man" he said.
"No worries" I said. "I didn't expect much from him and I got exactly that. At least I got a nice new computer out of it. That'll come in handy for college."
Kyle and I had both managed to score admission to the University of Chicago. I was going to study business. Kyle was working on an economics degree.
As the plans stood now, we were going to room together in an on-campus dorm. Neither of us particularly cared for that arrangement but the college required first years to live on campus. Between scholarships and my parents, my college, room and board was paid for. Eric had called a guy he knows with a gym near the college and I was going to go up and meet him over the summer to interview for a job there to give me spending money although, with the money Malcolm had accumulated for me, I really would have plenty of loose cash.
I received several other nice gifts and quite a bit of cash, which I discreetly slipped to Malcolm to invest.
As the party moved into the late afternoon, Kyle and I started to get antsy to head out. The lake party Mom had mentioned was a bit of a cover up. Kyle and I were going to the lake for sure but it wouldn't be a bunch of teenagers. Malcolm and Jorge had arranged a graduation celebration with a leather and S&M theme. The party goers would be other men from the group that was at Malcolm's party. Jorge, Malcolm, Austin and Cameron had already made polite exits and presumably were on their way to the lake house Jorge had rented to get things ready.
Finally, Eric came over to Kyle and me and told us he'd convinced my Mom that it was time for us to go and enjoy our lake party. I went over to my Mom with Eric and Kyle went to his parents and we both made our thanks and said our goodbyes.
Outside, we jumped into Kyle's Camaro and headed towards the lake. It would be about a 45 minute drive.
"Finally free" I yelled as Kyle turned up the music and sped up.
"There's a box in the back Jorge left with me. Told me to tell you to open it on our way up" Kyle yelled over the rock music coming from the speakers.
I reached behind Kyle into the small Camaro backseat and found a box a bit larger than a shoebox. It was black and had a black ribbon on it. When I opened the card attached to the ribbon, it said "Congratulations Josh. I'm very proud of the man you are becoming both in and out of the playroom! In this box are some things that I think will help us enjoy the weekend ahead. Put these things on and only these things. Your master, Jorge."
I quickly opened the box and found a black leather body harness that included a leather jock, a medium sized butt plug, a bit gag and set of nipple suckers.
I looked over at Kyle. He just grinned and said "I guess you better get yourself changed. I'm not stopping so you'll have to do it right here."
Fortunately, after graduation and before everyone arrived for the party, I had showered, shaved my lower body and thoroughly cleaned out to be ready for the party.
As Kyle sped up the highway, I removed my shoes, socks, shirt, pants and underwear. The only thing I now had on was my chastity cage that Jorge had put on my cock three weeks ago.
I looked over and Kyle was groping his package and I could see the clear outline of his hard cock through the gym shorts he was wearing. He smiled at me and nodded downward as if to say `want it?' My cock strained at the cage.
With some twisting and unnatural positioning, I managed to get the harness on sitting in the confined space of the sports car. I put the nipple suckers on, savoring the sensation.
I looked at the butt plug and said "no lube?"
"This is Jorge's thing. Guess you'll need to improvise" Kyle said with an evil grin.
The only thing I could think of was to lick the plug so I began to do so. Just as I put my mouth over the top of the plug to get it good and wet, suddenly, Kyle slowed the car some. I had not been paying attention but we were in the process of passing a big rig and Kyle had slowed down to match speed with the truck just as we were at the driver's window. I looked up at the driver's window on the truck and the driver looked down at me. He smiled and gestured with his hand. Up ahead was a sign for a rest stop.
"I think he likes you" Kyle said mockingly as he slowed down some more and fell in behind the truck. He followed the truck onto the exit for the rest stop.
I looked at Kyle as if to say "what the fuck" and he just grinned and said "read the back of the note."
I quickly found the note and turned it over. "Do as Kyle orders, Master Jorge"
`Fuck'
The truck parked at the far edge of the parking lot in the next to the last stall and Kyle pulled in to the last stall. The truck blocked the view from the rest stop of our car. Trees surrounded the rest stop so we had privacy, especially as the evening dusk was setting in.
The truck driver reached over and opened the passenger side door of the truck cab.
"I think he's waiting for you" Kyle said.
"Come on man" I said.
"Get up there" Kyle barked at me.
"Yes SIR" I said. I got out of the car, dressed only in the harness with a jock and quickly hustled around the front of Kyle's car and made my way to the truck passenger door. Kyle had rolled down his window and gave me a hard slap on my bare ass as I walked by.
Inside the cab of the truck, the truck driver, who looked to be in his thirties had lifted his t-shirt exposing his stomach and chest. He was hairy and had a hint of a beer belly but also had well developed arms and chest. His blue jeans had been pushed down around his ankles and he was waving a decent sized hard cock in the air.
"You a cocksucker?" the driver asked me.
"Yes he is" Kyle said from the car. I turned and glared at him. He just grinned.
"Well get on up here. I've been on the road all day and horny as fuck. Could use a nice stud mouth like yours" the driver said.
I grabbed the handle and pulled myself up into the cab of the truck. This truck had a sleeper cabin behind the driver and passenger seat. The driver turned in his seat so his legs were facing the middle between the passenger and driver seat.
"Well aren't you all dressed up" the driver said, eying me up and down. "Get on back there, lay down and lean that pretty head off the edge of the bed so I can fuck it."
By now, the whole scene was actually starting to really turn me on. I quickly crawled into the back of the cab and lay down on my back on the small bed back there and put my feet and legs straight up on the wall. I then lay my head back and let it dangle off the side of the bed.
The trucker didn't waste any time. He crawled back right behind me and presented his considerable and hairy ballsack to my mouth. "Lick".
I began to lick his balls, working to take each one in my mouth and properly bathe each one. He had certainly been driving all day. His balls weren't rank but they definitely smelled of sweat and man scent. Above me, I heard the trucker moaning in pleasure.
After at least five minutes of licking his balls, the truck driver pulled back and began to use his hard cock to smack me in the face.
"You little cocksucker. I saw you licking that plug in the car. Is it up your ass now?" the driver asked.
"Not yet" I heard Kyle behind the driver.
"Well let's get it in there" the driver said. He took the plug from Kyle as Kyle scooted into the back of the cab as well and sat on the bed next to where I lay.
"Show us that pussy hole" the truck driver said. I reached up and used my hands to pull my legs down and back, lifting my ass up.
"Nice" the driver said, running his rough, calloused fingers over my hole. I moaned involuntarily at the stimulation.
The driver put the plug at my mouth and I didn't need to be told twice. If he was going to put this up my hole, it was in my best interest to get it as wet as I could. I began to eagerly lick the plug and get as much of my saliva on it as I could.
The driver pulled the plug away from my mouth and presented his cock at my lips. I opened my mouth and began sucking his cock. Like his balls, his cock smelled of sweat and man musk.
I felt the plug at my hole and it began to push in. The pressure to enter me was persistent and firm. My licking helped but this was still a good sized plug without much lubrication. Just as the stretching of my hole became more painful, it slipped inside me.
"Ahhh" I moaned around the cock in my mouth.
"Ok, that ends plugged up. Let's get to using this pretty mouth" the driver said. He reached down and grabbed both sides of my head in a firm grip. He buried his cock in my mouth and throat. After holding it there long enough for me to start to squirm a bit, he pulled back and let me catch a breath. He then proceeded to fuck my mouth thoroughly. At one point, he paused to take off his shirt and wipe the sweat from his face with it. Kyle and the truck driver both played with the suckers on my nipples.
Eventually, the driver's breathing became heavier and he pulled out of my mouth. He grabbed his cock and stroked it and let out a yell, covering my face, neck and chest in his cum. Before he finished, he shoved his cock back in my mouth and the last couple shots coated my tongue.
The driver caught his breath, pulled up his pants and sat on the other side of me on the bed. He looked at Kyle and said "you use this cocksucker a lot?"
"As often as I can" Kyle said.
"Well, get to it" the driver said. "I'll watch and probably be ready to go again by the time you're done."
Shit, we were never going to get to the lake house.
Kyle wasted no time dropping his shorts and getting in front of me. I gladly opened my mouth and accepted his large cock. As he liked to do, he shoved it all in me at once and then began a rapid fucking that reflected his athletic power and ability. I had to focus to grab a breath now and then but enjoyed every stroke.
While Kyle used my mouth and throat, I felt the trucker playing with the suckers on my nipples and the plug in my ass. At one point, he slipped a rough finger in my hole next to the plug and found my sweet spot. My caged cock was leaking pre cum and I was getting close to a hands free orgasm.
Kyle's pace increased and then he buried his cock in me and began to grunt as he shot his load in my throat. As he removed his cock from me, I carefully licked and cleaned it.
True to his word, the driver was hard again.
"On your knees" the driver ordered.
I scrambled down from the bed and got on my knees in the small cabin. The driver walked up to me and presented his cock at my mouth. I gladly got to work sucking and working his cock. Although longer than the first time, it wasn't very long before the trucker was grunting and feeding me his second load.
After I had carefully cleaned the trucker's cock, Kyle said "Let's get going, don't want to keep the guys waiting. Thanks for the hospitality."
"Happy to. I think I'll sleep real good tonight" the trucker said, buttoning his pants up.
Kyle and I got out of the truck and back into the Camaro. Kyle pulled his cock out of his gym shorts and grabbed me by the back of the head and pulled me down to his crotch. I spent the rest of the drive sucking his cock and licking his balls. I was rewarded with another load for my efforts.
When the car stopped, Kyle let me sit up and I got a look at the lake house. House was a modest term. This was a mansion. We had parked in a circular driveway that had at least 15 other cars parked around it and there was room for more.
Kyle helped me put the bit gag on and we got out of the car and walked up to the front door. Cory, the guy who'd been at the door at Malcolm's party, was again attending the door here.
Cory and Kyle shook hands and did a man hug. Cory then looked me up and down. Admittedly, I was looking him up and down as well. He was dressed in tight Levis jeans that showed every muscle in his well developed legs. A cock running down his left leg was visible and I swear I saw it grow as he looked at me. Black work boots were on his feet and he was wearing a leather vest that was open to reveal a smooth chest and well defined abs.
"Someone's dressed for fun" Cory said. "Looking forward to having some fun myself tonight" as he reached out and twisted one of the nipple suckers, causing me to gasp.
"In you go" Cory said, opening the door for us.
Inside, the house was wide open with lots of windows looking out over a deck and the lake beyond.
Men were standing around in various outfits although none as revealing as mine. Several heads had turned as we walked in. Kyle took hold of the harness and pulled me along, clearly enjoying showing off his control of me.
We found Jorge talking to Austin in the living room. Jorge looked at me and smiled.
"Welcome" Jorge said. He took the bit gag off of me. "Get yourselves a drink. Only one! Then come back and we'll talk about the plans for the evening."
As I looked at Jorge, Austin and Kyle, they all had a grin on their faces as they eyed me up and down that told me that I was not going to be bored tonight.
Kyle and I walked to the open bar and retrieved two light beers from the bin of ice. We returned and sat down in a circle of sofas and chairs with Jorge and Austin. Malcolm joined us.
Jorge began "So tonight will go a lot like our typical parties with a few twists. Since you guys" he said pointing to Kyle and me "are the graduates, you'll be the center of attention. Josh, as a sub. Kyle, as a dom, well mostly."
I knew Kyle mostly topped but had never pictured him as a dom. I looked at him questioningly.
"I've been thinking about exploring some more BDSM and Jorge offered to coach me" Kyle said. "I hope you'll be ok being my sub as I learn the ropes. And what do you mean `mostly'" Kyle said looking at Jorge.
"Happy to man. You'll be great" I said.
"We have a starting ceremony for you two as graduates. A way to prepare you for college life so to speak. For that ceremony, you'll be right next to Josh" Jorge said with a grin.
"After the starting ceremony, we'll have a light dinner and then, Josh, you'll submit to Kyle and I'll coach him through some demonstrations. After that, things will go where things go for the night" Jorge finished.
"So let's get to it" Malcolm said. "You two, out on the patio, NOW" his voice suddenly becoming more authoritative.
"Yes SIR" I said immediately.
"Y, yes SIR" Kyle said with some hesitation.
"Get to it Kyle." We turned and saw Kyle's dad Richard.
"Dad?" Kyle said. "I didn't know you would be here."
"I'm here for the opening ceremony, you'll understand why in a moment" Richard said. "Then I'm heading home to take your mom out and celebrate getting our son through high school."
Kyle and I walked through the glass doors out onto the patio overlooking the lake and the forest beyond. The light on the patio was dim as the last bit of sunlight faded behind the hills.
In the middle of the patio were two sawhorses that had been bolted to the deck. There were straps at the base of each leg.
"Lose the clothes son" Richard ordered.
Kyle dutifully took off his t-shirt, shorts, shoes and socks.
"Both of you, over the sawhorses" Malcolm ordered.
Kyle and I each stepped up to a sawhorse and got into position, bent over. Four guys stepped forward from the group and strapped in our wrists and ankles to the legs.
"Now, these two young men here have graduated high school" Malcolm began. "They will soon be going off to college in Chicago. Like many young men, they may decide to pledge a fraternity. Those of you who were in a fraternity know that one of the initiation rights usually involves some form of paddling. We don't want these two representatives of our fine city to embarrass us by crying or being wimps so we thought we'd make sure their asses were nice and ready."
Oh shit.
Malcolm explained "Each of them will receive 13 shots representing the 12 years of school plus kindergarten. In addition to that, we have each of their high school transcripts and each will receive another shot for every B, two for every C and three for every D. Fortunately, these guys didn't get any Fs but each of them had at least one D."
I was rapidly trying to calculate. I had a D in Choir my freshman year, another one my sophomore year in Speech. I looked over at Kyle and he was clearly trying to do the same math in his head.
"So the totals are, for Kyle, 4 Bs, 3 Cs and 1 D so that's 4 plus 6 plus 3 so 13 plus the original 13, 26 if my math is right" Malcolm said. "And since I'm the banker for most of you, you should hope my math is right."
"Josh, 6 Bs, 1 C and 2 Ds so that's 6 plus 2 plus 6 so 14 plus 13 is 27" Malcolm reported.
"For the first ten shots, Jorge will paddle Josh and Richard will paddle his son Kyle. After ten, each of you can buy a shot by committing to donate at least $25 per shot to itgetsbetter.org. A $100 donation will add to the total shots they take."
Jorge and Richard stepped in front of us. Each of them held a wooden paddle similar to what you'd see in a principal's office or, yes, a frat house movie. They stepped forward and showed us that our names had been burned into each one.
"A gift to commemorate the night" Jorge said.
"Gee thanks" I said sarcastically.
"That'll be one additional shot for being a smart ass boy" Jorge barked.
"Yes SIR" I said, realizing the error I had made.
Richard and Jorge stepped behind us.
"Count them out and say thank you" Jorge ordered.
WHACK - my ass felt the first shot and I yelled out "One thank you SIR". Kyle repeated.
WHACK, "Two thank you SIR" and so on for the first 10. By shot number 6, my ass was on fire. Somewhere after 6, the plug was roughly removed from my ass. Thankfully as each hit with the paddle felt like it was driving it deeper into me.
"Gentlemen" Malcolm said, "Step on up and give from the heart and swing for the fences."
Kyle and I continued to take our shots as guys pledged and swung. I wasn't sure but it really seemed like I took a lot more than Kyle.
The group was generous. According to Malcolm, we raised just short of $2000 for itgetsbetter.org. While I thought it was great, that organization does great things for people trying to find out who they are, the bruises I saw on my ass in the bathroom mirror afterward were going to be a painful reminder of how much I gave for charity.
I went back out and found Jorge. He gave me a hug and deep kiss and told me how proud he was of me for taking the beating and not crying or protesting. "You're turning into a really good sub and pain slut" he said. Jorge removed the suckers from my nipples eliciting a moan from me from the pain and pleasure. My nipples stood out from my pecs and, I realized, would be very nice targets tonight.
As always, Jorge's approval made my heart leap and my cock try to get hard.
After dinner, Jorge got Kyle and me and lead us out to the patio. The sawhorses had been moved to the side and a bondage table had been placed in the center of the patio.
Kyle had put on a pair of tight leather pants, a leather vest and a leather captains cap.
"Up on the table Josh" Jorge ordered.
I got on the table and lay down on my back.
Jorge picked up two bundles of rope from under the table. He proceeded to coach Kyle in tieing my hands and legs to hooks on the table so that I was spread-eagle. Jorge was careful to show Kyle how to tie firmly but not too firmly to cut off circulation.
Next, Jorge gave Kyle the key to my cock cage and told him to remove it. As soon as it was off, my cock sprang to full mast, hard as a rock and leaking precum. Kyle stroked it a couple times looked at me with an evil smile.
Jorge brought the bit gag and handed it to Kyle who put it on me. He also put a blindfold that Jorge gave him on me.
At this point, I was starting to slip into my sub headspace, enjoying the firmness of the ropes binding me and the loss of visual from the blindfold.
I felt my balls being tied off and felt the tug of them being pulled towards the bottom of the table. Weights or something had been put on the other end of the rope. Not so hard that it hurt, just enough to notice. I suspected that would change as the night progressed.
"Mmmmph" I yelled around the bit gag as my right nipple let my brain know that it was being clamped by something very hard. Wasn't long before the left nipple made a similar report.
"Ahhhhh" I tried to scream as clamps were attached along my cock.
"Ohhhh" I moaned as a small vibrating egg was inserted into my ass and landed squarely on my prostate.
I could tell my already hard and leaking cock was almost gushing.
"Gentlemen, as you can see, our new graduate Josh is in quite a predicament. And his friend and dom in training, Kyle, also a graduate, has done an excellent job of immobilizing Josh and beginning his pain journey for tonight" I heard Jorge say.
I didn't like the word `beginning'.
"Feel free to step forward and attach these wherever you think they'll do the most good on Josh" Jorge said.
Within a few seconds, I felt more clamps being attached all over my body. My chest, shoulders, waist, cock, balls, legs, even on my fingers and toes as well as the webbing between them.
Shortly after new clamps stopped being attached to me, I heard Jorge announce.
"Now, a few of you step forward and take one of these and help us cover each of the clamps."
I began to feel hot liquid dripping on my body in various places. They were using candles to cover my clamps in wax Several times, the person dripping must have had the candle very close to me as I felt a significant burn when the wax made contact with my body.
By the time the wax stopped being coated on my body, I was moaning around the bit gag from the pain of both the clamps and the hot wax.
"Now, as part of his training, Kyle is going to learn to use a riding crop on his sub" Jorge announced.
OH FUCK!
"Kyle will be using the crop to knock each one of these clamps off of Josh's body. Because of the wax, some of them are going to be more resistant to being removed than others."
OH DOUBLE FUCK!
"AHHHHHHH" I screamed around the gag when the first clamp, on the side of my chest, close to my armpit was knocked lose.
"AHHHHHHH FUCK" I tried to yell around the gag as clamps were hit, sometimes coming loose, taking wax and skin with it and sometimes staying in place needing another strike or two from the crop.
My brain was racing. The endorphins from the pain combined with the realization that I was the center of attention for a bunch of men and my best friend was learning to hurt me had me flying high. My cock never lost its hardness.
As Kyle continued to knock the clamps loose, I writhed in pain and continued to scream out around the bit gag. When the clamps on my cock were knocked lose, I raised my torso up off the table as I screamed.
Suddenly, I felt my cock being stroked. After three weeks of no cumming, I immediately forgot the pain and began to enjoy the sensation of my cock being stimulated. I even felt someone sucking on it. Awesome, I was going to get to cum. I began to pant and moan as I got closer. Just as I felt like I was going to peak all stimulation stopped and something slammed into my balls.
"Ahhhhhhhhhh" I screamed in both the frustration of the interrupted orgasm and pain in my balls.
"You didn't think you were going to get to cum did you?" I heard Kyle whisper in my ear.
Had Kyle been the one sucking me too?
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