--------------Chapter 15--------------------
***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 14---------------Within a minute, Kyle began to breathe harder and suddenly, he pulled out of my mouth, grabbed his cock and started jacking a large load all over my face and chest. I quickly took the head of his cock back in my mouth so I could get some of his cum. Once Kyle came down from his orgasm, I carefully licked and cleaned his cock from top to bottom.
"Dad says he's always willing to stay up late for good head" Kyle said. "His room is at the end of the hall and the door should be ajar. I'm going to go get a shower and hit the sack. If you're up for it, I'll have more whenever you're ready" as he grabbed his cock and shook it at me.
Kyle was right, this was like some bad porno or one of those stories I read on nifty.org but who was I to complain?
------------Chapter 15---------------After servicing Kyle on the patio, I made my way to his dad's bedroom door and it was, as Kyle as said it would be, slightly open and a dim light was visible inside. I knocked lightly, not wanting to wake Richard up if he had dozed off.
"Come in" Richard said in his deep, manly voice.
I was still naked from the pool and some of Kyle's cum was still crusted on my face. Kyle had told me to not clean it off, that his dad would like it.
"Hey Josh, what can I do for you?" Richard said. He was laying on his massive bed, naked with no covers or sheets on him reading a book. His cock was laying along one leg but I noticed it was starting to sir.
"Well, Kyle gave me your message and I was wondering if you were still awake SIR" I said.
"Well, I am" Richard said.
I walked over to the bedside and assumed my submissive position. Feet shoulder width apart, hands behind my back and eyes pointed downward.
"I'm here to service your cock or anything else you require SIR" I said.
"Good boy" Richard said, reaching up and pinching and twisting my right nipple until I gasped. "Can you handle some pain boy?"
"I will handle whatever you want me to handle SIR" I said.
"Good. That chair, over there, assume the position" Richard ordered.
I remembered the position Kyle had take and I walked over to a high back chair facing the fireplace and placed both hands on the back of it, spread my legs and stuck my ass out.
Richard came up behind me and placed his hand on my lower back. "Brace yourself boy"
A moment later, I felt the paddle hit my ass across both cheeks.
"Ahh, one SIR" I said, imitating Kyle's performance earlier.
Another shot hit my ass.
"Ahhhahhh, two SIR" I said as the 2nd was harder than the first.
This continued until I had taken 20 shots and my ass cheeks burned like I had third degree burns.
"Impressive boy" Richard said. "Now, get down here and take care of my cock so I can seed you and get some sleep."
"Yes SIR" I said and turned around. Richard's cock was huge. It must have been over 10 inches hard and thick like a soda can. I suddenly was nervous about being able to handle this monster.
"Uh, SIR, I should tell you that yours is the biggest cock I've ever seen. I might struggle to give it the oral service it deserves" I said as I dropped to my knees.
"Boy, I'm quite used to handling cocksuckers who struggle with my wood. Don't worry, one way or the other, I'll put it all down your throat. You'll either take it willingly or I'll force it. Now, get on it cocksucker" Richard barked.
I immediately set to licking his cock and balls to get them nice and wet and lubricated for the throat assault I expected.
"Suck it, NOW" Richard barked. "I ain't got all night."
"Yes SIR" I said and began the task of getting my lips around the massive head of his cock and starting to put it deep in my mouth. I began to use my hands to massage and pull on the lower part of his cock but he slapped them away.
"Your job is to suck my cock. I saw the picture from Kyle and his positive review. I also see his load on your face. You're a cocksucker so suck cock." Richard ordered as he put his large hand on the back of my head and pressed into me. Not having any warning, I had not taken a breath or focused on relaxing my throat. Richard continued to press into me as I gagged and spasmed. He did not let up and pushed until my nose was buried in his well groomed pubes.
It took all my self-control to just let him assault me. This was my role here, to take his cock and let him use my mouth for his pleasure. It was not my place in the presence of this alpha man to do anything but take it.
After a little while of stretching my throat with brief breaks for me to catch a little air, Richard grabbed me by the hair and pulled me around to the front of the chair. "On your back in the chair, legs up against the back of the chair" he ordered.
I quickly got in the chair and turned so that my legs were going up the back of the chair, my back was on the seat cushion and my head hung upside down off the front of the seat.
Richard stepped up and straddled my head. "Open" was all he said. Once I had my mouth open, he pushed forward until he had lodged his cock in my throat all the way. Once he had the positioning right, he began to fuck my throat with ever harder thrusts. At one point, the chair started to move and tilt but he didn't slow down. Throat slime was running down my face and pooling in my nostrils making it even harder to catch a breath. Richard reached down and clutched my throat. "I can see it pushing down your throat" he said and I could feel my throat pushing out as his cock stretched it. He continued to grip my throat progressively tighter. I was starting to get light headed but he didn't relent.
"Fucking cocksucker, take my load" Richard finally yelled although it sounded far off to me in my air restricted haze. I became aware of him pulling out and I was able to gasp some fresh air into my lungs just as he began to paint my face with his large load of cum. I quickly came to my senses and opened my mouth and stuck out my tongue to try to catch as much as possible. Seeing this, Richard plunged his dick all the way back into me while he finished his load.
After Richard caught his breath and extracted himself from me, I quickly got on the floor on my knees and make sure his cock was completely cleaned from top to bottom. While I was doing this, Richard took several of the cum shots from my face and kept putting them on his still hard dick for me to lick off.
"Now, get out of here so I can get some sleep. Be outside my bedroom door on your knees at 6am" Richard ordered as he walked over and crawled into bed and turned off his lights. I crawled out of the bedroom on all fours, not feeling that walking upright was something I should do in this man's presence.
Totaled up, I took three loads from Kyle and two from Richard that night and went home with a sore throat and struggled to talk for a couple days.
A few days later...
"I decided we'll hold any further financial consultations here at my house instead of in the office" Malcolm said. "Less chance someone may interrupt us and I'm more comfortable with conducting laundered money outside my bank."
"Thank you SIR" I said. I wasn't in much of a position to disagree, laying naked except my cock cage on the bondage table in Malcolm's basement playroom. My wrists and and ankles were shackled to the corners of the table and my arms and legs were stretched to what I felt like must be their maximum. My balls were in a parachute that was connected to a chain connected by a pulley to a 15 pound kettlebell.
I had been in this position since arriving at Malcolm's house an hour ago. Malcolm had left me on the table while he conducted a conference call for work. Periodically, while talking on his cell phone, he would walk over and cause the kettlebell to swing, increasing the pull on my balls. He would also pinch and torture my nipples and tickle my sensitive feet. I was under orders to not make a sound that could be heard over the phone and had been told that a violation would result in a punishment.
Unfortunately, I had lost control during one of the tickling sessions and laughed out loud. Malcolm covered it on the call easily and gave me an evil smile. After the call, Malcolm moved directly to my finances and had not mentioned my punishment. Making me wait for it was part of the torture.
"Now, you have another decision to make" Malcolm said. "The associate I worked with to clean up this money normally charges a 15% fee for his services. When I explained how you earned this money, he was intrigued and interested in possibly trading some of your services for his fee. He wasn't specific but shared that he is into controlling, humiliating and using sexually. I've never seen this associate playing with anyone but I have some other associates who indicate he's sadistic but respects limits and is very intune to his masochist's needs and safety."
`I wonder what this guy looks like?' I thought to myself.
Malcolm continued "Jorge and I discussed and agreed that we support you working off the fee and keeping the money but we would leave it to you to decide. The session would be an overnight session. Jorge and I have discussed certain limits for your safety with the gentleman and he has agreed. He has provided recent STD testing and is negative so he will be permitted to use semen or urine on or in you but no other fluid exchanges. There can be no permanent changes to your body or damage that would require medical attention. Marks such as cuts or bruises will be confined to parts of your body where they can be concealed wearing shorts and a t-shirt. No bones may be broken and you must be left in a condition where you can walk out at the end of the session on your own power. No drugs or alcohol except poppers and viagra can be used on you. The session will be one-on-one, nobody else will participate. He has offered to give you a safeword but that would only cover half the fee. Willingness to go with no safeword gives you the entire fee back. Jorge or I would be in attendance during the session but would not intervene or become involved unless he violated the terms."
"It would appear you and Jorge have thought of everything SIR" I said.
"This isn't our first rodeo boy. You're far too valuable to let some nutjob destroy you. I enjoy playing with you" Malcolm said as he lifted the kettlebell, releasing the pull on my nuts before he let it go and it dropped again.
"Ahhhh" I screamed as pain shot from my balls into my stomach and I felt a bit nauseous.
"Noisy today aren't you" Malcolm said. "When we're done with financial discussion, I think I'll be gagging you. I've got something special to do it with."
That wasn't going to be pleasant.
"So what's your decision? It'd essentially be like earning about $1700 for a session but I suspect this session will be far more intense than anything you've done in the massage room at the gym or anywhere else for that matter. This man is in the position he is because he knows how to get the most for his money."
"I'll do it SIR. I trust you and Jorge completely with my safety" I said still in a great deal of pain from the drop on my balls but still wanting to keep the money.
"Good, I'll let him know after we're done here today. In fact, he asked for a picture of you in advance and I can't think of a better shot to send him than this. Smile for the camera" Malcolm said as I heard the click of his smartphone camera. "We'll work out dates and times with Jorge and Eric so you can be free from home or work."
"Thank you SIR" I said.
"Now, last decision and then I have a activity planned that you probably won't enjoy but I will" Malcolm said. "As far as where to put the money, we can put it into some decent safe investments that will net you some good money or we can be more aggressive. There are a startup companies I know of that always need cash and are willing to give up ownership stakes in their company to get it. These companies are not sure bets and you could lose everything but I know of one that I think would be a good bet. They need a lot more than your money but I'll pool yours with some of mine and we will share the reward equal to our portion. Of course, we could both also lose our money as well."
"May I ask what we could make SIR?" I asked.
"I would say you could easily double your money within a few months if their idea pops. They're close to launching and I think it will take off like a rocket" Malcolm said.
"Like I said, I trust you SIR" I said. "Please invest it the best way possible. I understand the risks."
"Good, I like your aggressiveness. Now you'll get to experience some of my aggressiveness." Malcolm said.
Malcolm walked out of my line of site. Shortly after, I felt him at the head of the table. "Open up your mouth" he said. When I did, he shoved something made of cloth into my mouth. It was damp and warm and did not smell good.
"That's my jock I've worn to the gym for the past two weeks without washing it. For good measure, I pissed on it just now" Malcolm said.
He quickly pulled a rubber hood over my head that covered everything except my nose. I could not see anything and certainly could not do anything but keep the rancid jock in my mouth though, somehow, the intimacy of sucking on his piss covered jock was erotic and turned me on.
I next felt something being pushed between my lower back and the table. It felt hard and square. It had the effect of raising my torso and ass up and away from the table and pulling harder on my ankles and wrists, still bound to the table corners. I moaned into the jock.
Something cold and metallic pressed at my asshole. With continued pressure it eventually settled in my hole. It felt like a medium sized butt plug but somehow felt more rigid. I felt something being wrapped around my ballsack and then felt something being stuck to the bottom of each of my feet.
Suddenly, I screamed into the jock as I felt sharp, painful shocks running down my legs. The plug in my ass and whatever was wrapped around my balls seemed to be passing electricity down my legs to my feet. Every shock caused my leg muscles and ass to contract severely. The parachute with the kettlebell remained on my balls so the contractions were also having the effect of pulling my balls harder. My arms and shoulders protested the jerking and abuse while they were still bound to the top of the table.
I could hear Malcolm near my ear. "Next time, learn to control your outbursts when I tell you to. I've put the box on a random pattern and set it to 30 minutes. Enjoy the ride."
For what seemed like a lot more than 30 minutes, I bucked, clenched and yelled as the electro torture devices inflicted tingling shocks of various pattern and intensity up and down my legs. My prostate was being fully stimulated by the plug in my ass and I could feel the spikes digging into my cock as it tried to harden in its cage.
Eventually, my body was covered in sweat, I was having to concentrate on breathing through the nose holes in the hood and my leg muscles were contracting and cramping simultaneously causing almost non-stop pain.
When the shocks finally stopped. I felt the pads being removed from my feet and the loop on my balls removed. The plug was pulled roughly from my hole. The parachute was finally removed from my balls.
"I'm going to remove the hood but you better not spit out that jock until I tell you to boy, got it?" Malcolm said.
I nodded my head vigorously.
As the hood was removed, I saw Malcolm standing next to me. "You took that pretty well. Just know that wasn't even 50% of the power that box can do."
Malcolm stepped to the foot of the table and I felt my ankles being released. He quickly pulled them upward and attached the straps on my ankles to chains hanging from the ceiling. He pressed a button on a remote he was holding and my legs were pulled back and to the sides until I didn't think they would go any farther, leaving me in an almost split position with my ass openly available.
Using a step-stool, Malcolm climbed up on the table with me and, with no lube or anything, shoved his entire hard cock in my ass in one quick thrust.
I moaned in a mixture of pain and pleasure as Malcolm set out to give me a rough fucking. I looked up into his eyes and he looked into mine. His eyes were filled with lust and passion and I felt like I could almost cum while my cock was in my cage I was so turned on with his power and alpha male presence.
I never left a fucking from Malcolm disappointed. He seemed to bring new energy and technique to every session. This time was no exception. By the time he put his alpha man sperm my my hole, he was sweating and breathing heavily. I loved the sensation of feeling his sweat drip onto me, mingling with my sweat.
When I got back in my truck to leave Malcolm's, I was grateful for the butt plug he'd put in my ass as I didn't want to leak his cum all over the seat. Looking at my phone, I saw that my dad had tried to call me. I had texted him earlier in the day to let him know the baseball team was coming to St. Louis for an end-of-season tournament and I hoped Kyle and I could stay with him and maybe have some time to hang out. I was also hoping that he'd be able to come to our games since he hadn't been to one of my athletic events since the divorce and move to St. Louis.
I hit the call back button and he answered almost immediately.
"Josh, how's it going man?" dad said.
"Good dad, you?" I replied.
"The same as usual, lots of work, you know" dad said. "So, listen, about the tournament, I don't think it's going to work to stay here. I've got a new girlfriend who's staying with me and she's not a fan of kids. Apparently she had to raise her little brothers and sisters and is, in her words, done with it."
"Oh, ok, that's cool I guess. We can stay at the motel with the rest of the team" I said, trying to not let my disappointment come through in my voice. "Can you at least come to the games. The team is great this year and I'd like you to meet my best bud Kyle."
"Well, I'll try but she takes a lot of maintenance and attention if you know what I mean" he said with a chuckle. "And work's crazy, so don't count on it but I'll do my best."
I knew what that answer meant, he was telling me no but didn't want to come out and say that.
"Ok, well, yeah, I understand. I'm glad you are seeing someone you like so much" I said, almost adding "that you like so much that she's more important than your fucking son."
"Hey, Josh, thanks. Listen, I'll transfer a few hundred bucks to your account and you and Carl can use it to enjoy the town while you're here" Dad said.
"Great, thanks, Dad" I said, not bothering to correct Kyle's name. I was pretty sure Dad and Kyle would never meet. "Well, I gotta go, got some homework to get done before dinner."
"Ok, kiddo. Hey, hit a homer for me ok?" Dad said and I heard the phone disconnect.
"Mother fucking asshole" I said as I threw my phone into the passenger seat.
When I got home, Eric and mom were sitting on the patio drinking some wine.
"Eric, my dad isn't going to be able to put us up in St. Louis so Kyle and I will need a room at the motel with the rest of the team."
"Sorry to hear that, Josh. Is he going to be out of town or something?" Eric asked.
"Something like that, yeah" I said, not wanting to admit to them that my father had chosen his latest bimbo over his son.
"Ok" Eric said, eying me as if he knew I wasn't telling the whole story. "I'll make the arrangements."
"I'm sorry, Josh" my mom said looking at me sympathetically. I'm sure she knew there was more to the story. "Well, you'll get to see him when you go up to St. Louis during the summer."
"Yeah, maybe" I said, deciding then and there that there would be no trips to see my father any time soon. "Well, I've got homework to get done. You guys have a good night."
"There's a chicken salad in the fridge if you're hungry" my mom said.
"Thanks, maybe later" I said as I went inside.
"My asshole dad is too busy banging his latest slut so he can't host so we'll be at the motel with the rest of the team" I texted Kyle once I got to my room.
The phone rang with a video chat almost immediately. It was Kyle.
"Hey man, I'm sorry to hear your dad is such a dick" Kyle said. He was laying on his bed, shirtless as usual.
"Yeah, but he was nice enough to say he'd send me some money so we could enjoy ourselves" I said, propping the phone up on my dresser so I could begin to undress.
"Hey, no worries, we'll have a blast. Two dudes in a motel room. Hell, if nothing else, you'll have plenty of time to be on my big dick" Kyle said. I looked up at the phone and he had flipped the cameras so I was looking down his body at his cock. He was using his other hand to wave it around at the camera. I felt my own cock harden again in the cage.
"Stop that man, you know how much it hurts when I get hard" I said with a laugh as I turned around to put my clothes in the hamper.
"Nice butt plug man" Kyle said. I had forgotten I was even wearing it and when I bent down to pick up my socks, it was blatantly visible to the camera.
"Yeah, a little present for the road from Malcolm" I said. By now I had shared everything with Kyle, including that his neighbor a few streets over was my financial advisor and sadist.
"Reminds me, dad told me to tell you that mom was going back to California in a few weeks and he'd be thrilled to have you over again" Kyle said. "Bring the butt plug, might be interesting."
"Sounds like fun man. Your dad is awesome, wish mine was" I said and must have had a pretty pitiful look on my face.
"Dude, that's seriously fucked up. What can I do to help?" Kyle asked.
"Make sure we have a kickass time in St. Louis. Maybe I'll have you send him a pic of me sucking your cock as my way of coming out to him" I said. "That'd kill him."
"Dude, I specialize in having kickass times. Leave it all to me." Kyle said.
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