Previously: Charles gets unexpectedly called out of town for the weekend, but Pete agrees to meet with Jack at the condo to continue their mentoring sessions and then go out to celebrate their progress. At the condo after finishing their meeting, Jack asserts himself again by fucking Pete on the marble island as a warmup to the evening. He forces Pete to wear a Kum Katcher in his hole to save his cum for later, and then tells him "we're meeting my old roommates and fuck buddies at the bar. They've heard ALL about you and can't wait to meet you. I told them what a hot daddy you were, and I'd be very upset if you disappointed them."
"Detour Into Depravity" isn't my first story for Nifty, but it's my most personal. It's largely autobiographical in that the story's main character, Pete, is essentially me. His background, feelings and emotions are mine. Some (ok, most) of the sex is fantasy, but like any good fantasy, I'd make it happen if I could.
Please email me your thoughts as you read this. It helps to hear what turns you on and seems realistic, and what...not so much... psorenson9@hotmail.com
And like aways, make sure you contribute to Nifty to keep all these great stories coming at http://donate.nifty.org/.
Thanks for reading. Enjoy.
Chapter 4
The bar wasn't far from Charles's condo and we were there in minutes. I couldn't stop thinking of the Kum Keeper that was penetrating my ass hoping it didn't dislodge and leak cum down my legs. I didn't know if I was more afraid of the embarrassment it would create, or the anger it may provoke in Jack if it were to happen. Fortunately, it seemed comfortably secure in my hole, so I decided to relax and enjoy the feeling, as best I could.
We walked in and Jack immediately spotted Chris and Marco who were saving two seats at a 4-seat high top for us. Jack bound over to them and gave them each a big hug. He then motioned me over to them and announced, "Gentlemen, this is Pete that you've heard so much about. He's a great guy and LOVES to have fun, if you know what I mean..."
At the table were two remarkably handsome young guys, both roughly Jack's age which put them in their late 20s. They both popped up from the table to greet me effusively. I could only imagine what they had been told about me, and when my imagination went there, I chubbed up at the thought. My mind exploded with what they might have been told, "He's a little slut...he's a hungry cocksucker...he's Charles's and my new little bitch"....etc, etc." And somehow, not only did that not bother me, it made me even hornier.
I settled into the table and Jack immediately ordered us a couple more beers. Good thing I like beer well enough; I wasn't given a choice. Jack explained earnestly how I was helping him direct his career efforts and seemed genuinely appreciative. It turned out Chris had launched a career in finance, and Marco was a personal trainer with a robust clientele.
I wasn't surprised to see these two had been Jack's fuck buddies. Chris, a former D1 basketball star at OU was 6'4" and had an amazing physique. You could tell he focused on keeping fit and he wasn't shy about showing it off. African American, great smile, long muscular torso, and even longer legs. I had to wonder what other body part of his might've been long.
Marco was more of a muscular fire hydrant. He too he had been a D1 athlete at OU, in rugby. And he looked right out of central casting for a rugby jock. Curly brown hair, Mediterranean coloring, thick strong arms and legs, tight waist, and a huge package protruding from between his legs. He was proud of his equipment and clearly liked to advertise it. And as hot as those two were, Jack more than held his own. Smooth, muscular, curly brown hair, incredibly charismatic, he rounded out the threesome nicely.
Although I easily had 25 years on each of them, I held my own. "Body by CrossFit" is how Pook used to introduce me, and I was even more fit now. Indeed, Chris asked me early in the conversation, "Damn stud, how do you stay in such great shape? You make the three of us look like wimps."
"Speak for yourself", Marco interrupted with a laugh, but Jack answered for me, "Pete competes in CrossFit at a national level. He works out several hours a day, and it shows, doesn't it gentlemen?"
There he went again; his attitude kept toward me kept vacillating between genuinely respectful and rude and domineering. I decided I liked both.
"Well dude", Marco offered. "Whatever you're doing, keep it up. I hope I look half as good at your age."
"You should see what else he does well, `for his age'", Jack added with a grin and a pair of air-quotes.
With three sets of eyes waiting for my response, I simply raised my glass to them and toasted, "To good times."
The evening continued like that for a few hours, with various friends of theirs, often my age, coming and going, seemingly hoping to pick one of them up. Chris and Marco weren't having it though. Jack appeared to have briefed them for what was to come.
Finally, Jack pushed back from the table and called it a night. "Let's go back to my place and see what kind of trouble we can get in", he smirked, looking straight at me.
This was all so new to me. In my former life, if I'd even found myself in a situation like this (which I wouldn't have), I'd be one of the alphas. Tonight, I knew that wasn't to be. Yet I relished the opportunity to surrender to these guys and commit myself to their pleasure.
We hopped in our two cars and were back at Jack's in no time. Jack and I got there first and when the elevator door closed behind us, he grabbed me, pinned me against the wall, and spit out, "Are you gonna behave tonight? You gonna make me proud with my friends? They know all about you and have high expectations. You're not gonna disappoint them...and me, are you?"
Startled, but totally turned on, I quietly answered, "I'll do my best sir. What are your expectations though. I don't want to disappoint."
"You're going to get fucked harder and deep throated deeper than you ever have before, and all I want to hear is how much you're loving it, is that understood?"
"Yes sir," I promised, not knowing if I could deliver. But I was highly motivated, that was for sure.
"Good, now get naked except for that sexy jockstrap you're wearing and keep the plug in. I want you in nothing but your jock when they get here."
"Yes sir," I replied. He had no idea how his domineering attitude was making my heart beat and my cock swell.
I quickly removed my clothes and laid them on the bed in the next room. Again, I was torn. On one hand I was humiliated standing there in nothing but a jockstrap when the others arrived. But on the other, I wanted to be as vulnerable and near-naked as I could when they got there. That was my role in life now. Before long, the buzzer rang, the elevator doors slid open and Chris and Marco poured out of it.
Seeing me, they didn't hold back, "God damn, look at the piece of daddy-meat Jack has lined up for us. I thought you were hot in the bar, but jesus christ I want a piece of that", Chris nearly shouted. Marco then added, "Jack, can I fuck him? PLEASE???"
"Pete is here to give us whatever we want", Jack replied. "Marco, your wish is his command," and turning to me added, "isn't it Petey?"
Now I was `Petey' I thought. What had it come to?
"Yes sir," was the only logical response I could offer. "Thank you, sir." `Where the fuck did that come from?', I thought.
"Pete, get us all a beer", said Jack with a tone that bordered on rude. When I replied, "Yes, sir" and headed to the kitchen area, I could see Jack and his buddies exchange glances. As best I could tell, Jack was signaling, See guys, I told you so', and their response was, Holy shit, Jack's really got this'.
The second I handed them their beers, Marco popped up with, "Let's head to the bedroom, I can't wait to get naked with this guy" leering at me. He briskly stripped on the way to the bedroom and by the time I got there, he sat naked on the bed, stroking is very thick cock which was nearly buried in his thick brown pubes. "On your knees, Petey boy", he commanded.
I was more than happy to comply and promptly knelt directly in front of him lowering my mouth to his thick cock. His was a good cock to start with because it wasn't that long. I knew I'd have my tonsils punished later and this was a good warm up. I eagerly took him fully into my mouth which caused him to cry out to the others who weren't even in the bedroom yet, "Holy shit you guys. Pete's mouth is AMAZING. Keep sucking Pete, you're a pro". Jack and Chris promptly joined us to get in on the action and furiously undressed each other. Now both nude too, they walked over to either side of us when Chris placed his hands underneath my armpits and lifted me off of Marco's cock, up from my knees. He pulled me into himself with a warm, loving embrace and kissed me passionately. "You my CrossFit bitch?" he asked. "Yes sir," I demurred.
"Yes, what?" he continued.
"Yes, sir. I'm your CrossFit bitch, sir."
"Much better, boy," he finished.
As Chris embraced me, he reached down my back to grab my ass and felt what was lodged in my hole. "What the hell?" he gasped as he felt it with his fingers.
Knowing exactly what he was referring to, I looked to Jack to explain. "Ah, you found it", Jack smirked. "Petey and I had a quick Round 1 before we joined you tonight. I told him I wanted his hole nice and wet for you guys, so I plugged him up so he didn't lose any of my baby juices. Now you guys don't even need lube. But be careful when you pull it out. I shot quite a load in him; we don't want him dripping all over now, do we...?" he added.
"You had that in you all evening?" Chris asked incredulously.
"Yes sir," was all I could respond. The embarrassment was simultaneously humiliating and titillating. But the humiliation was overshadowed by knowing I was the slutty target of their lust.
"On your hands and knees, Pete. Who wants first crack at his wet hole?" Jack asked.
Marco piped up, "I'll go first, but I want a taste before I do. I need to verify its Jacks jizz, not some stranger's. And I'd know Jack's jizz anywhere."
"All yours" Jack responded as he pointed to my ass which was now in the air.
Marco got on his hands and knees behind me and carefully grabbed the Kum Keeper contraption with his teeth and gently pulled it out of my hole. As comfortable as it was when it was inserted, it was a relief when removed. As he pulled it out, he immediately covered my hole with his mouth and it felt like he sucked some of the jizz right out of my hole. "Hell yeah, that's Jack's jizz all right. Come here Chris and have a taste."
"Let me at it", Chris said as he dove into my hole. I felt his tongue take a long lick and then felt a sucking sensation. "Yup, that's Jack all right. Nicely done Jack."
"Leave some up there for later boys. We need Petey good and lubed up for when we all fuck him."
They all laughed and Jack tossed a bottle of lube to Marco as he was preparing to enter me. "Just in case", Jack indicated.
Marco lubed himself saying, "I'm sure you're plenty lubed up from Jack, but we're gonna go easy on you at first". After coating his cock he began to slide it up and down my crack. As I moaned he asked, "You like that, don't you Petey? You know what though, I'm suddenly hungry again. Anything good to eat up that hole of yours, Pete?" And with that, he lowered his head again and forcefully tongued my crack, hole, and all the way up to my balls. It was like it was his first time rimming and he was shocked at how much it turned him on. He was up and down my crack several times, with his tongue nice and flat indicating he was a pro at this. All I could do was moan. He paused for a moment and then said, "Ok, I'm going in for my treat", and pulled my cheeks apart as far as they could go, pointed his tongue and tongue-fucked me with all he had. "Mmmmm, Jack always had the best tasting jizz...Mmmmm" He'd pull his tongue out occasionally with an exaggerated swallow/slurp to make the point that he was savoring the jizz Jack had deposited in me earlier. Marco's tongue was up my hole, my ass was in the air, my head in the pillow and I could feel my cock dripping. I'm not sure I'd ever experienced that level of hedonistic pleasure. And I knew my hole was as wet and ready as it could possibly be. Just then, Marco stopped and said "Ready Pete? You've probably never had anyone as thick as me," he warned.
"Please fuck me, sir" I whimpered.
I immediately felt his cock enter me, slowly but surely. He didn't pause once as he entered. All I could feel was my hole stretching and expanding to take his cock. It felt so good I couldn't think straight, but I had the wherewithal to clamp down on it as he entered. "Holy fuck, Pete's grabbing my cock with his hole. He's a fucking animal. Ohhhh, ohhhhh, I bet you love this thick cock invading you, don't you? Tell me how much you love it, Pete."
"I fucking love your thick cock sir. Please fuck me hard. Breed me, please sir."
"Damn this stud is tight", Marco gasped. "He's squeezing my cock like it's in a vice."
"Slow down a minute, Marco," Jack offered. "I'll give you something you'll never forget" he said as he stealthily slid behind Marco, both on their knees, put a copious amount of lube on his own cock, bent Marco over Pete's back and slid his own cock into Marco's hole. Now Jack was fucking Marco doggy-style, who was fucking me, doggy-style. The three of us got into a rhythm that sounded like an orgy. Groaning, moaning, panting, swearing. And knowing my role as the deliverer of pleasure, I did everything possible to clamp down on Marco to create the maximum friction around his cock. This went on for what seemed like an hour, but I'm sure was much quicker. I eventually worked my magic because, without warning Marco shouted "Fuck! I can't hold it".
"Breed me sir", I begged. "Breed. Me. Now."
Almost immediately, Marco shot his load deep into my guts, and, once again, I felt gratified beyond imagination. His cock remained hard, yet I had milked what felt like a quart of cum from this young, Mediterranean god. I was pleased beyond words.
Marco kept himself planted in my hole even as it started to soften, but that didn't stop Jack from drilling Marco. Every time Jack thrust into Marco, Marco's cock was pushed deeper into my hole. Unexpectedly, Jack pulled Marco off and out of me and quickly pushed his own cock deep into me. He didn't want to miss a beat between pulling out of Marco and fucking me. "Ready for Round 2 stud? You better be...I'm cumming....."
"Yes sir! Breed me sir! Breed me" I screamed.
"FUCK!!!" Jack shouted as he exploded into my hole for the second time that night. By now, I had collapsed onto the bed and was flat on my stomach. I knew I was close to cumming as my cock was being rubbed against the mattress as I was being fucked. But I knew better than to come without permission, so I raised my hips slightly to eliminate the friction.
That actually gave Jack a better angle to continue to fuck me as his cock continued to pulse in my hole. That was a moment that time could've stopped forever and I would've been a happy man. Feeling Jack's warm pulsing cock spewing cum into my gut was sublime. Between Marco's and Jack's explosions of cum, I couldn't imagine how much cum was sitting in my gut. I only knew they'd need to be careful if they ever let me off the bed so I didn't drip all over the bed.
Marco had pulled out of me a while ago, and now he and Chris were sitting against the headboard at the head of the bed, their legs extended on either side of me, and their cocks not far from my face. Although Marco and Jack had already cum, I was still supercharged with testosterone. With Jack still slowly pumping me from behind, I lifted my hands to grab each of their cocks. "Mmmmm..." I heard them both groan. "What a slut," Marco added.
Jack didn't appear to be ready to move off my ass, so I squeezed each of their cocks and said, "Feed me your cocks." I wanted more.
"Hell yeah," was their simultaneous response.
As I was still face down into the mattress, Marco slid under me so his cock was right at my mouth. "Clean it up, daddy slut", he ordered. I hungrily lapped up all the jizz and funk off his cock from my recent pounding. He was still somewhat soft, but the harder I worked, the more plump he became. "Good daddy," he groaned. "Good daddy." I had been promoted from boy to daddy.
"My turn," I heard Chris say. Marco slid out from under me and Chris took his place. I hadn't noticed yet, but Chris's cock, now rock hard, was from a whole other planet. It was literally the longest cock I had ever laid my eyes on. It was like out of a porn movie. I wouldn't even be able to get it halfway down my mouth, but I was going to try.
Looking up into his eyes, I said, "I'll do my best sir, but I can't promise anything."
"Do your best boy. Get it good and wet. You'll need it sloppy wet for when I fuck you." His tone implied a challenge, even threat when he said that. Here's what he didn't know...
What none of them had any reason to know was that I was able to take a dick of any, and I mean any length. Probably too much information, but I had colon surgery several years ago when they removed my sigmoid colon for digestive reasons. The sigmoid colon is the one that twists from your large intestine and connects to the top of your rectum. And it's also the muscle that blocks long cocks from entering all the way up. Except for me. I knew this for a fact because I've tested myself with dildos that are longer than any human cock. I've had dildos well over 12" up there. Yeah, it takes a bit of lube and some poppers, but those bad boys nestle deep in my hole like they found their new home. I luxuriate with more than 12" of dildo up my hole and I know I can take even more. I'm even able to sit on it so it was pushed up into my colon without an inch hanging out. I secretly knew I was ready for anything Chris could send my way.
"Fuck me Chris, please fuck me." I was already begging. I was shameless.
"You sure you can take all of this big boy?" he sneered. "Not many can", he bragged.
"I bet you can't take it halfway up", Jack sneered.
"Wanna bet...sir?" I said as I pulled Chris's cock out of my mouth.
"Hell yeah," Jack replied without hesitation.
"Ok" I said. "If he gets his entire dick up my hole, I fuck you. And I cum in you."
"You're on", Jack replied, nonchalantly.
"How do you want it?" Chris asked. "Doggy style or on your back?"
"On my back, please sir", still acting deferential.
I rolled over on my back and Jack and Marco straddled me on either side. They each grabbed a leg under my knee and pulled it up to my chest so my ass was complete exposed for Chris. Meanwhile, Chris was standing at the base of the bed, slowly covering his enormously long cock with lube. I looked at it, and while it was undoubtedly the longest I'd ever seen in person, it didn't come close to the monster dildos I've enjoyed solo. I was incredibly confident. And hard. I wanted him in me badly.
The boys were holding my legs in the air with my ass hanging off the end of the bed. Chris was gently rubbing his cock up and down my crack. "Ready stud?", he asked gently.
"Yes sir. All I ask is you go slow. But I can take it."
I soon felt the tip of his cock enter my hole and since he wasn't as thick as either Jack or Marco, it felt tolerable, even great. I knew to keep breathing and push hard when he got up there.
"More lube?" he asked.
"Sure," I replied. "Can't hurt"
He pulled out and applied one more thick coating of lube to his entire cock. I knew this was going to be one of the most enjoyable fucks I'd ever experienced. Chris's incredibly long cock embedded in me, and I'd win the bet. I was flying.
"Fuck me, Chris. Fuck me." My enthusiasm surprised all of them. He was already about a quarter the way up and I begged for more. He continued to effortlessly slide up into me until now he was at least halfway up. I'm sure Jack and Marco thought I'd beg him to stop, but again I surprised them. "Keep fucking me stud. I can barely feel you. I want to feel your cock in my throat. Don't hold back."
I could see Jack and Marco exchange glances. I was obviously preoccupied but I sensed they were both incredulous.
"Ok, I'm going all the way in", Chris said. "Ready?"
"Fuck yeah", I shouted. "I want all of it. NOW!"
That's all it took for Chris to take one last long thrust up into my guts. I could now feel his balls tickling my own and I felt the tip of his dick well past my prostate, somewhere around where those monstrous dildos landed some time ago. I was in heaven. It honestly felt like his cock was reaching up to my throat. I wanted him to stay there forever and never move. But at the same time, I wanted him to slide it in and out of me, full length...in and out. I wanted it all.
Chris didn't disappoint. He slowly withdrew his cock all the way out, and then punched it back up into my guts. Then he did it again, and again, and again.
I couldn't talk; all I could do was groan. And moan. I even tried to beg for more but couldn't form the words. Having that warm, undulating cock drill me so deep was the sexual experience of my lifetime.
All of them were speechless. They had no idea how much I could take. Finally, Marco said, "Watch the tip of Pete's cock. Every time Chris's cock rubs his prostate, he leaks precum. You can see it happening." I was able to look down and he was right. By now, my cock had leaked a puddle of pre-cum on my abdomen directly below my cock, the tip was wet, and every time Chris went in or out, it spurted even more. It was like cumming without cumming; like one long continuous orgasm. Marco scooped up a fingerful and fed me with it. "Mmmmm..." I groaned. After Chris passed over my prostate again releasing another dribble of pre-cum, Jack scooped it up and fed it to Chris. "Tasty stuff", Chris smiled. "Man, this is the best fuck I've ever had" groaned Chris. "No wonder Jack was so excited about you man. I'm gonna fuck you all night long."
I was still speechless. All I could do was moan, groan, and whimper. Like Chris, I wanted this to go all night long. I was leaking so much pre-cum, I didn't feel in danger of cumming. Good thing, because I didn't have permission. But I knew I'd won the bet with Jack so at least I'd be able to cum when I fucked him.
Inevitably, Chris picked up the pace. I was now in a trans; I barely knew what was happening to me, but I could hear the voices cheering him on. "Fuck him, Chris. Fuck him hard. Take his hole. Give it to him hard." My consciousness was limited to my rectum. It was the only body part I could feel, or that mattered. Everything else slipped away. Chris was now long-dicking me with the precision of a porn star. He'd slowly push all the way in, stop, then slowly pull all the way out. His cock was so long, it took a good :15-:20 seconds every time he pushed in or pulled out. And I could feel every second of his cock's progress, in and out. It was exquisite. I'd never felt anything as crushingly erotic.
I finally found the energy to whimper, "Please Chris, give me your seed. I need your seed". He slowly but decidedly picked up the pace. Every time he pulled all the way out he pushed all the way back in. All 10+ inches of him penetrated me, then left me. Over, and over, and over. The sensation on the inside of the full length of my rectum was electric and radiated throughout my body. I've never had one, but I may have been experiencing a non-ejaculatory orgasm. It was that intense and it my entire body felt it. And all I had to do was lay back and take it. Jack and Marco were holding my legs in the air giving Chris full access to his prize.
His pace continued to accelerate when I took the final step. With all my energy, I clenched my rectum as hard as I could around his cock until his entire body tightened, he pushed himself even further into my gut, if that were possible, and blasted countless spasms of cum up into me. I was ready to cum myself, but somehow was able to hold back. I was so completely satisfied with what he was doing to me, it didn't bother me that I didn't cum. The feeling of his cock spasming in me was enough. Feeling his warm jizz invade so high up in my gut gave me a feeling of satisfaction that was unmatched. I felt his body continue to spasm long after the orgasm began, and I knew I was the singular instrument of his pleasure. Once again, that feeling of giving pleasure instead of receiving it was intensely gratifying.
Jack and Marco gently released my legs so that now Chris was laying on top of me and we were face to face. "You're fucking amazing" Chris told me. "No stud, it's all you," I replied. We laid there for what seemed like forever not knowing (or caring) what Jack and Marco were up to.
When Chris finally pulled off me, he gave my still rock hard cock a gentle slap, looked at me and smiled and said, "Somebody here won a pretty big bet", and then looked at Jack and said, "and somebody else lost. How do you want him Pete, on his back or doggy-style?"
Given the strange relationship between Jack and me so far, I was a bit reluctant to answer. Would he tell me to go fuck myself? But Jack was an honorable man, and he looked straight at me and asked, "What'll it be, boy?"
"On your back, sir. I want to see you when I fuck you."
Jack crawled onto the bed and laid on his back exactly where I had laid. As if choreographed, Chris and Marco grabbed his legs and pulled his knees to his chest, just like they had done to me.
I squatted down to inspect his hole; I was going to savor this opportunity. I knelt down, flattened my tongue and took several long licks up and down his hole. "Holy shit," he groaned. "Damn that feels good." "I'll take good care of you, Jack. Just lay back." I replied.
Although I was going to be the one doing the fucking and had permission to cum, I still was committed to giving him pleasure. I don't know what had come over me, but it was paramount that I give my partner pleasure. My pleasure was a distant second.
I continued to lick and devour his hole until I thought he'd cum himself. "Ready Jack? Remember how thick I am? You better brace yourself."
Chris tossed me the lube which I applied liberally, and I placed the tip of my cock squarely against his hole. "Argghhh..." he moaned. And I hadn't even penetrated him yet. This would be fun!
I thought it wise to apply even more lube to go easy on him and then I slowly penetrated him. "Ok there, bucko?" I asked. "Yeah, I can take it", Jack replied. "Keep going". Happy to comply, I pushed in further and made him groan. "Damn, you are THICK", he groaned. "You ain't seen nothin' yet big guy", I sneered.
"Breath deep", I added before pushing it in even further. "I'm only about half way in" I informed him.
"Damn, only halfway? I feel like I have a 2x4 up me", Jack half complained, half groaned with unspeakable pleasure.
"There we go, just a little further", after I had continued pushing. I gave it one more, very slow push in, and I was all the way. "Ok, boy" I said, knowing now I was in charge. "I'm going to let it sit there for awhile for that tight little ass of yours to get used to it."
"Thank you daddy," Jack replied.
Role-reversal complete.
I was motionless for what felt like minutes and then started to very slowly pull out, then in, out then in. Each time a little further out, and in with slightly more velocity. I looked down at Jack and he was sweating. We locked eyes and there was genuine affection in his.
"Oh daddy, thank you for your cock. You're so fucking thick. Please fuck me daddy," he begged.
And so it began. I pumped in and out forcefully, then vigorously, and finally with a vengeance. "Fuck me, I want more", he ordered. "Fuck my guts out daddy. Breed me. Breed your boy."
That's all it took for me to explode. I had over eight days of cum stored in my low hanging balls that had been ready to blow for the last several days. And when I came, I came with an intensity that startled all three of them, especially Jack. He didn't think I'd ever stop spasming my jizz up into his gut. Every time he thought I was done, I'd jerk again with another blast. It went on and on and on. Until finally I was done.
Face to face, Jack was covered in sweat and looked like he'd been run over by a truck. I whispered "You ok Jack? I didn't mean to hurt you."
"I'm more than ok Pete. You won the bet fair-and-square. And I got the fuck of a lifetime. But tomorrow....back to normal, you're still my little bitch", and he cracked a bit of a smile.