--------------Chapter 24--------------------
***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 24---------------
After a while, I had no idea how much time, Paul began to stop applying forward pressure and began to back out of me.
"Stop, no" I pleaded.
"It's time for a break Josh" Paul said gently. "Don't worry, you'll get more of my fist and perhaps others later."
--------------Chapter 25--------------
After Kyle helped me get out of the sling, we joined Jorge and Paul upstairs in the kitchen where they were enjoying a beer. Kyle got beers for him and me and we sat down at the table.
"First fist, big milestone" Jorge said. "What do you think?"
"It was unreal. Thank you" I said, looking at Paul. "The connection we had was amazing."
"Gentle fisting like we did can be very passionate" Paul said. "But it's also fun to go off and do some punch fucking and work a whole to the extreme" he continued with a grin.
"Sign me up!" I said.
"Careful what you ask for" Jorge said. "Paul here has sent many a guy home with an obscenely stretched out hole."
"Only if it was what they wanted" Paul said. "Or did you not ask for that Jorge?"
There was a pause of silence as Kyle and I processed the idea of Jorge getting fisted by Paul.
"Yes, it was exactly what I asked for and I walked away happy, if not a little wobbly" Jorge finally said with a sheepish grin.
"So, let's talk about tonight" Jorge said, clearly trying to change the subject. "Paul, you need to get anywhere or can you hang out with us?"
"I've got no plans until Tuesday" Paul said.
"I was thinking we could invite a few guys over and grill some steaks" Jorge said. "Nothing too elaborate, just a nice dinner and then see where the night goes."
"Sounds great" Kyle said.
"Awesome" I said.
"Count me in" Paul said. "I've got a buddy that owns a gourmet market and I'll bet he'll spring for the steaks if he gets to join in."
"Deal" Jorge said. "Give him a heads up and we can start rounding guys up so we can tell him how many."
Paul and Jorge pulled out their phones and began messaging and calling. Over the next hour, a total of eight guys confirmed, including the guy with the market, Eli and Orson.
Jorge sent Kyle and me off to the grocery store to pick up other things for the party. He also put in a liquor delivery order.
When Kyle and I returned from the store, it was around 5pm. The guests weren't due until 7pm. Jorge made drinks for the four of us and we sat out on the back patio, enjoying the moderate evening temperature.
"So, all of the guys we've invited are players in the scene in one form or another" Jorge said. "Dinner will be much like any other dinner with clothes on but after-dinner, things will likely get interesting."
My cock twitched in the athletic shorts I had put on for the trip to the store.
"After another round of drinks, we'll all get cleaned up and dressed. Nothing too fancy but nice enough that we can enjoy the company" Jorge said.
Paul stood up and said "I'm going to grab a cab home to get changed and cleaned up. I'll be back in an hour or so."
After Paul left, Jorge looked at Kyle and me and said "tonight is not going to have any script or structure. I want you two to just enjoy yourselves. Be safe and be respectful but don't get caught up in any roles or preconceived ideas."
"If it feels good, do it?" Kyle said.
"Sort of but be smart" Jorge said with a grin. Looking at me Jorge said "No restrictions on you tonight. Go for it because I'm going to lock you in chastity before we head home tomorrow afternoon."
My cock twitched again. Both at the idea of the total freedom and the idea of being put in chastity again.
We headed inside and each of us got cleaned up, inside and out.
Noting that Jorge also cleaned out as well as Kyle, I was definitely curious where the night would go.
Jorge, Kyle and I each put on some khaki shorts, loose fitting button up shirts and flip-flops.
We set to work getting the house ready for our guests. Everything was straightened up, liquor bar was set up, hor d'oeuvres set out and the side dishes readied for cooking.
Paul returned with another man in tow. They were both carrying boxes that turned out to be the steaks for the evening. Paul introduced us to Adam, the owner of the market.
Adam looked to be in his late 30s. He had a slim build that reminded me of some of the long-distance runners on our track team, and looked to be about 6 feet tall His hair was curly and sort of messy but in a sexy sort of way. He was wearing a form fitting, sleeveless shirt and tight jeans riding low on his hips. The jeans suggested a nice sized package underneath.
As Adam shook my hand when we met, his grip lingered a little longer and he gave my hand an extra squeeze as our eyes met.
Eli arrived with a buddy, Brad. Brad was Eli's age and built just as nicely with blond hair that was styled into a sexy pompadour. His outfit of knee length camouflage shorts and tight t-shirt looked awesome.
Orson arrived. It was great to see him again after our encounter in the woods behind his cabin on the way to Chicago. He was wearing a sexy button up shirt with several buttons undone and a pair of cargo shorts.
As the remaining men arrived, Kyle and I became the appointed bartenders and kept busy mixing and serving drinks. More than a few remarks were made about how my drink serving skills had improved since a couple nights before.
The remaining men were Sam a young construction worker with the body to match and Vic and Don, a couple middle aged bikers with nice builds.
The surprise of the night was when Malcolm arrived. Turned out he was in town for business and was happy to take Jorge up on the invite.
Jorge and Adam took up grill-master duties and got the grill going. Each of us were polled as to how we liked our steaks.
As the evening progressed, I found myself not thinking of the men as play partners but more as friends. Soft jazz music played in the background as good conversations about work, family and travel dominated. Hardly any talk of bondage or sex. No physical contact was made beyond what you'd see at any other summer party in any town anywhere.
It was good news that most of these men were Chicago based as this would give Kyle and I a good network to plug into socially, and otherwise. We made sure to `work the room' and exchange contact information for the future. Each guy perked up and smiled on hearing we would be going to school in the city.
Jorge gave Kyle and me a heads up when the steaks were on and we put the side dishes that needed cooking in the oven. Through some maracle, all of the food finished at the same time and we set up a buffet on the kitchen counter. Everyone grabbed a plate and found somewhere to sit, eat and continue talking. Compliments were handed out about the food.
After eating, conversations continued and the party shifted tone a little. The light faded away outside and the lights inside the townhouse were kept low. The music subtly shifted to more of a rock feel; still subtle but more intense than before. Several of the guys had either taken their shirts off or had them completely unbuttoned.
I found myself on a small couch in a dark corner of the living room talking to Adam, the owner of the gourmet shop and provider of the meat. For a while we talked about his business, school and normal topics. Gradually, the conversation shifted towards sexual adventures. Adam mentioned that he was disappointed he had to be at his shop the night before and couldn't attend the party where I had been the center attraction. He said he had heard rave reviews both before this evening and from Eli and others tonight. I thanked him and told him it was great and definitely hot.
We were both sitting facing each other on the sofa with one leg up on the sofa and our other legs hanging down. Both of us were barefoot. Subtly, our feet on the sofa had made contact and we were rubbing each others' feet as we talked. Adam's hand reached out and began rubbing my thigh. He leaned over and we began to kiss. Before long, he had pulled off his shirt and I had removed mine. Despite looking skinny before, his body was well toned with nice pecs and abs. We continued kissing and I was laying on top of him as we kissed more and explored each other's body with our hands.
"Want to take this somewhere more private?" Adam asked.
I reached down and tweaked one of his nipples and said "Want to take this somewhere more kinky?" and grinned.
"Fuck yes" he said, grinning back.
I lead Adam to the playroom. Turned out we weren't the first to venture there. The sling was already occupied by Vic, one of the bikers, with Don, the other biker working his fist in him. Orson had Sam, the construction worker, strapped to the fuck bench and was feeding his cock down Sam's throat. Malcolm was on the other end of the bench fucking Sam. Paul had Jorge's hands tied above his head on the platform and was showing Kyle some flogging techniques. Eli and Brad were nowhere to be seen.
Finding the leather covered bed unoccupied, I lead Adam to it. Along the way I grabbed some handcuffs, a hood and some nipple clamps.
Adam and I stripped our remaining clothes off and resumed kissing and groping each other on the bed. Adam got on top of me and began to kiss, lick and bite his way down my torso. Stopping for extra attention to my armpits and nipples. After a while, he reached my very hard cock and began to suck on it. It didn't take long before he was balls deep on it and giving me an amazing blow job. I reached down and ran my fingers through his messy hair and began to hump my hips up and down to fuck his mouth. He was a skilled cocksucker, not gagging or protesting.
Figuring if Jorge was going to be sub, I might as well be dom, I grabbed the handcuffs, pulled away from Adam's cocksucking and pushed him facedown on the mattress. Pulling both arms roughly behind his back, I cuffed them tightly. I then leaned down near his ear and said "Your safe word is `steak', ok?"
"Yes SIR" he said with a grin.
I took the leather hood and pulled it over his head. The eye holes were zipped shut as was the mouth hole. I rolled him on his back and positioned his head hanging off the edge of the leather mattress.
Grabbing the nipple clamps, I stood on the floor, unzipped the mouth hole in the hood and began to feed my cock back down his throat. Once I bottomed out, I stopped and held it there. Adam did not protest and used his tongue to lick the portion of my cock not down his throat and swallowed a couple times, making his throat muscles massage the rest.
Just before I was ready to pull back and give him a breath, I put both clamps on his nipples at the same time. He yelled out as my cock left his throat and I didn't wait and shoved it back down again. We continued this routine, me cutting off his air with my cock for longer and longer periods each time. He gagged a couple times but never protested or seemed to pull away. I felt myself getting close and, not wanting to cum this quickly, pulled out of him and zipped the mouth shut again.
Leaving Adam laying on the bed, I went over to a cabinet for some more accessories. Returning to the bed, I positioned Adam on his back, head at the top of the bed. I tied his ankles to hooks on the bottom corners of the bed, spreading him and leaving his cock and balls available for play. We had been so busy playing, I had not noticed that Adam was sporting a very nice and large cut cock and a set of large, low hanging balls. On his slim and tight frame, they even looked larger.
I attached a ball parachute to Adam's balls and connected that to a rope that ran through a hook on the middle of the bottom of the bed frame. I pulled the rope until I heard him moan a little and tied it off.
I then took a pinwheel and began to test various areas of his body for reaction. He bucked and yelled quite a bit when I ran it on the bottom of his sexy feet. So, of course, I did that more. The more he twisted and tried to get away from the pinwheel, the more his balls were tugged on.
Changing my area of attack, I ran the pinwheel up the inside of one leg and down the other several times. I then ran the pinwheel over his tightly stretched balls. This elicited a loud yell from inside the hood.
Pausing for a moment, I unzipped the mouth on the hood and said "How're you doing man?".
"Fuck, I'm so ticklish" Adam gasped.
"You know the word if it's too much" I said.
"Do your worst" he gasped.
I decided to leave the mouth open and returned to running the pinwheel over his balls and up and down his very hard dick. When I got to the head of his dick, he bucked harder than he had before and howled either from the stimulation or the yanking his balls were getting.
I decided to give Adam a few minutes to catch his breath. Leaving him there on the bed, I wandered around the room checking out the others.
Don was punch fucking Vic mercilessly and Vic was yelling in pleasure, pain or both. Kyle was on his knees sucking Jorge as Paul continued to flog Jorge. Jorge yelled with each hit but also said "thank you SIR" each time. Orson was now fucking Sam who was still bound to the fuckbench. Malcolm was using a riding crop on Sam's back while Orson fucked him. Eli had Brad tied to the St. Andrews cross with a ball gag in his mouth and was putting pegs all over his body.
Malcolm saw me watching and set the crop down and came over to me.
"I see you decided to flip to being top" he said, motioning his head to the restrained Adam laying on the bed.
"Yeah" I said. "I figured if Jorge can do that" nodding towards the platform "I could change it up a bit too."
"Good, Adam's a pretty tough bottom so he can handle it. Mind if I join you?" Malcolm said with a grin.
"Be my guest" I said.
"Oh, before we get on with it, I want to talk to you tomorrow before you guys head home. It's about your money" Malcolm said. "All good news, in fact it's great news!"
"Sure" I said.
Malcolm and I went over to the bed where Adam was still breathing hard from the stimulation I had been giving him with the pinwheel. Malcolm grabbed Adam's stretched balls and began to squeeze. Adam moaned and eventually began to yell. "Ahh, shit, ow!"
I pulled off the nipple clamps and began to roughly rub Adam's nipples. He yelled more from the pain of the blood returning to his nipples.
Malcolm let go of Adam's balls and stepped away. When he returned, he had a tray with various sized sounds on it. He set the tray on the bed and used an alcohol wipe to clean the head and length of Adam's still hard cock. He then put on a rubber glove and took the smallest of the sounds, put lube on it and began to push it into Adam's cock. Adam moaned, a moan that sounds like pleasure.
Figuring Malcolm would keep Adam occupied, I again began to check out the room.
Sam was still tied to the fuck bench but Orson was nowhere to be seen. Sam saw me walking around and licked his lips and motioned me to come over. I walked over to his head, grabbed his hair and shoved my cock down his throat.
After skull fucking Sam for a while. I went around back of him and began fucking his ass. His ass was wet and loose from Orson's and Malcolm's large cocks but still felt warm and awesome. I grabbed Sam's hips and began to fuck him hard. Sam moaned and yelled "fuck me!"
Kyle walked over and presented his very large cock to Sam's mouth. Without hesitation, Sam opened up and took every inch. Gyrating his pubes into Sam's face, Kyle looked at me and smiled. Best buds spit-roasting a hot young construction worker. Hot!
After a bit, Kyle and I switched. We repeated this a couple times. Finally, we both looked at each other and knew, it was time. I slammed Sam's ass as hard as I could a few times and yelled out as I blew my load in him. Kyle, at about the same time, yelled out and, I assume, fed Sam his cum.
Hearing some clapping, I came out of my fuck trance and noticed that the rest of the group, minus Adam, was standing around, watching us and stroking their cocks.
Kyle and I looked at each other, leaned over Sam's body and kissed. This brought even more applause.
After Kyle and I extracted ourselves from Sam, we released him from the fuck bench and the three of us kissed some more and played with each other's bodies. I began to stroke Sam's 8 or so inch cock. Before long he was blowing his load.
I then went back over to the bed where Adam was still restrained in the cuffs and by his feet and balls to the bed. His back was arched and his head pulled back so that Orson could feed his cock down Adam's throat. Adam was taking it like a champ.
At the same time, Malcolm had resumed sounding Adam's cock and was up to the largest sound. It stretched Adam's piss slit obscenely. I knew it had to be hurting but Adam was too busy taking Orson's cock down his throat to make any noise about it.
I grabbed a crop and began to crop Adam's chest and stomach. Again, with Orson's massive dick to swallow, Adam wasn't in much of a position to yell out but he periodically would moan or make a guttural yell around the cock in his throat.
Orson grunted and moaned and dumped his load down Adam's throat. As he pulled away, Adam kept his back arched which gave me a great target to crop. I reached down and began to stroke Adam's cock while I continued the flogging. I edged Adam to the beginning of his orgasm several times, stopping and torturing him with orgasm unfulfilled. Finally, as he was reaching the top again, I dropped the crop, released the parachute from his balls and began to stroke him harder. With a yell that made most of the other men in the room look over, Adam blew a massive load all over his chest and stomach.
I grabbed the pinwheel again and began to run it up and down Adam's cock, focusing on the head. He screamed, bucked and yelled for me to stop. I continued for at least two or three minutes. Despite his pleas and yells, his cock never went down.
Once I decided he'd had enough, I scooped up the cum from his body and fed it to him through the hood. He greedily licked my fingers clean.
I released Adam's feet from the bed, removed the hood and cuffs. Within a few seconds, he grabbed me, pushed me down on the bed and jumped on top of me and began to kiss me, hard. I happily returned the kiss.
"Now, let's find that private place" Adam said between kisses.
Without hesitation, I stood up, threw Adam over my shoulder and carried him to an unoccupied bedroom. Inside the room, I threw him on the bed and pounced on him, swallowing his cock immediately. He spun around and began working my cock as well in a perfect 69.
I didn't expect to get much sleep tonight.
"So, remember that we invested your money into a couple of startups looking for investors?" Malcolm said to me over coffee in the kitchen the next morning. I was wearing a pair of athletic shorts. Malcolm was dressed in a suit as he was heading out after we talked.
Adam was still asleep in the room where we had fucked well into the early hours of the morning. My body was so conditioned to getting up at an early hour after all this time working at the gym, getting in morning runs etc. that I was awake even with only a couple hours sleep and having blown at least a half dozen loads.
"Yeah" I said. "A tech company and a drug company if I remember right."
"Yeap. Well the drug company got FDA approval a few months ago on a drug that's a huge deal. Next week, they'll announce that they are going public. Your investment in the company will be worth well above $250,000" Malcolm said.
I almost dropped my coffee cup.
"This doesn't happen very often" Malcolm continued. "I knew there was a good chance this company would do well but this drug is a game changer for diabetes. It turned out to be much more effective than they had expected, doctors are prescribing it faster than they can make it and the market is beating down their doors to buy the stock. The IPO will give them the cash they need to increase production."
"Shit" was all I could manage.
"So, you've got a choice to make. You can cash out and take the money or, you can take some or all of it in stock in the company" Malcolm explained.
"What are you doing with yours?" I asked.
"Taking the stock" Malcolm said. "The dividends will be a nice steady income and I expect it will continue to grow in value."
"Well I don't have much I'd spend that kind of money on so I want to do the same as you" I said.
"I thought you'd say that" Malcolm said, smiling. "Now, get your ass in the playroom. Jorge wants to see you".
"Yes SIR" I said with a grin as we both stood up. "Malcolm, I can't thank you enough" I said as I pulled him into a tight hug.
"Oh you'll find plenty of chances to thank me" Malcolm said, grabbing my ass.
Malcolm headed for the door and I and headed to the playroom. The room reeked of sex and sweat. Toys and accessories were scattered everywhere.
Jorge was sitting in a chair drinking a cup of coffee. He was naked and I quickly took off my shorts to be naked as well and assumed my sub stance. Feet shoulder width apart, hands behind my back, head down.
"So, did you enjoy last night?" Jorge asked as he sipped his coffee.
"Yes SIR" I said.
"Good. It looked like you and Adam made a nice connection. I enjoyed getting to watch you be the dom. You're pretty good at it. Thinking about switching to a dom role?" Jorge asked, cocking an eyebrow.
I walked over to the chair, dropped to my knees and took his cock in my mouth and began to suck it.
"Well, guess that answers that question" Jorge chuckled. "Good, I like you on your knees in front of me boy."
"Thank you SIR" I said with his cock still in my mouth.
"Get me off boy and then we will get ready to head home" Jorge said, grabbing the back of my head and pushing me down on his cock all the way.
After Jorge had pumped a load down my throat, he gave me instructions.
"Cold shower and then put this on" he said, handing me a metal cock enclosure. I noticed it was the one with the spikes inside. That one was not pleasant.
"You'll be in chastity until the summer is over. I'll consider removing it before your going away party but you will need to earn that privilege" Jorge said.
"Yes SIR" I said, taking the enclosure and heading over to the wet area in the room.
I turned the shower to cold and began to wash. The cold water quickly deflated my cock. I put the cage on before I turned the water off since, even though I had blown at least six loads in the last 24 hours, my cock still wanted to get hard.
As I was drying off, Jorge came back in the playroom with two guys carrying buckets and other cleaning supplies.
"These are the cleaners. They're going to put things back in order before the owner gets home. You'll need to give each of them a blow job as part of their compensation" Jorge said and turned and walked out of the room.
The two guys were fairly young, probably in their late twenties, one was black, the other white. They both wore coveralls that fit them tightly and indicated nice builds and well filled packages.
Jorge hadn't left much question as to what I was to do so I walked over to the two guys and dropped to my knees.
"Fuck yeah" the white guy said. "I've got a three day load in here for you cocksucker."
He unzipped his coveralls and pulled off the top part revealing a well developed chest with lots of tattoos and pulled out a cock that was at least seven inches and still growing.
Grabbing me by the back of the head, he plunged his cock down my throat. Wasting no time, he began a brutal skull fucking, jerking my head back and forth aggressively on his cock. Thankfully I had plenty of practice doing this.
The other guy stepped over next to the guy pummeling my face. He had also dropped his coveralls and had a long black cock out, stroking it to hardness. I reached up and started stroking it for him.
"Fuck yeah bitch. Get that cock hard so I can shove it in your pretty white boy face" the cleaner said.
That apparently did it for the guy pumping in my mouth. He yelled out "swallow my cum you cocksucker" and pumped a large load into my mouth.
As soon as the first guy had recovered and pulled out of my mouth, the other guy grabbed my head and pulled me onto his cock that had grown to at least 9 or 10 inches. Down my throat it went and so began another rough skull fucking.
The pain in my cock registered in my brain finally as my cock tried to get hard in its spiked cage. Damn, wish I could jerk off while doing this.
"Take my black cum you pretty white boy" the cleaner currently abusing my throat yelled as he pumped another load down my throat.
Once he was done and caught his breath, both cleaners put their coveralls back on. I stood up.
"Looks like you don't get to enjoy that" the first guy said, nodding at my cock cage.
"Yeah. All part of my duties to Jorge" I said.
"Well, you ever want a dick to suck, look me up" the second guy said, handing me a card. Looking at the card, it said his name was Oscar he was co-owner'. The other guy handed me a card that said his name was Calvin and it also said co-owner'.
"So you guys own the company" I said. "Would have thought you'd have staff to come out here and do this."
"We have about 50 people" Oscar said. "But, we always do this job ourselves. We enjoy the perks it sometimes comes with and, sometimes we make use of the room ourselves."
I grinned. So these guys were players too.
"Well, I'll be attending school here in the city starting in August" I said. "If you're ok with it, I'll take you up on that offer. I like guys who know how to be rough."
"You bet man. We sometimes need extra guys who are built like you for heavy lifting projects. Maybe we can hook you up with some hours and extra cash" Calvin said.
"Awesome" I said. "I'll text you my contact info later today."
Calvin and Oscar began cleaning up the room and I washed my face and cleaned up a bit from my oral workout. Jorge had left a pair of athletic shorts, socks and sneakers for me to wear. No shirt, no underwear. I put on the clothes and headed out into the house.
I found Jorge and Kyle standing by a computer screen in the kitchen grinning.
"Enjoy the show?" I asked.
"Yeap. You never disappoint" Kyle said.
Jorge handed me the butt plug that I had worn on the drive up to Chicago. It was vibrating and had an electro tip on it.
"You know what to do" Jorge said.
I dropped my shorts and bent over. Jorge put the plug near my mouth and I licked and tried to slobber on it as much as I could. Jorge then shoved it up my ass and attached the cable for the remote control. I stood up and pulled up my shorts. Kyle grabbed the remote and turned on the random vibration setting. I moaned and already felt my cock pushing on the spikes. He dropped the remote into the pocket of my athletic shorts.
"Ok men, let's hit the road" Jorge said. "Josh, you're driving. Kyle and I want to get a nap."
"Yes SIR" I said, catching the keys as he threw them at me.
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