Finally Caught Up with Me Ch. 02

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Editor’s note: this story will make the most sense when read after “Finally Caught Up With Me”

Randy wasted no time making good on his threat of blackmail. My phone buzzed me awake the very next Sunday morning. It was a text from a number I did not know, but soon deduced was Randy’s.

“You need to be at my place at 11am. Plan to be here for 2 hours.”

I was wide awake now. I roused myself quietly and went downstairs to make coffee and figure out my alibi for today’s rendezvous. As I was reliving my last visit to Randy’s office in my mind, Charlotte came downstairs looking especially hot in a pair of white cotton bloomers and an unbutton nightshirt. I was definitely pitching a tent in my boxers, which she noticed.

Thinking my noticeable erection was her doing, she came up to me for a kiss and reached down and grabbed it. We kissed for a while before she dropped to her knees, pulled down my boxers, and took my cock into her mouth. Charlotte wasn’t big on blowjobs and she wasn’t terribly good at them, but she knew I liked getting them from her. She hated the smell of cum and I knew as soon as my precum began to ooze out, she would quit the blowjob and want to be fucked.

I closed my eyes and let me imagination run wild with what Randy had in store for me. Sure enough, Charlotte pulled off my cock saying, “ew gross. OK, no more of that.” She stood up in the kitchen and turned away from me, bending over the counter. I yanked her bloomers down and grabbed her hips, pressing my thumbs into her back dimples, and entered her. I’m shameful to admit it, but I’m a fast cummer. When I take her from behind I cum especially fast, like less than a minute. True to form, I blew my load in a matter of seconds. She kissed me and grabbed her coffee and went upstairs to shower.

I pulled up my boxers and sipped my coffee. My phone buzzed again.

“Confirm or your cover is blown.”

I quickly typed a reply.

“I will be there at 11. Confirmed. Do I need to bring anything or prepare for anything specific?”

I waited…watching the 3 dots.

“just make sure you’re on time cocksucker. You’ve got a full day.”

I finished my coffee and went upstairs. I told Charlotte a friend from work asked me to help with a big yard project at his house. I padded my time and told her he thought it was a 5-hour job and he needed me at 10:30.

“That’s fine honey. I’m gonna grab lunch with Susan and maybe go get our nails done.”

That was easy, I thought. I showered and got dressed for ‘yard work’ and left around 10:15. Leaving myself that much time was unwise. I was just nervous and horny the whole time and drove aimlessly around town, burning gas.

11:00am finally arrived and I knocked on Randy’s door. He let me in.

“Good morning handsome. Right on time.”

He closed the door behind me and kissed me deeply up against the wall.

“So what did you have in mind for our 2 hours together this morning?” I asked gingerly.

“Well first, you need to get naked. You look like you’re going to go do yardwork.”

I thought about explaining my alibi to him, but I just did as Randy asked and undressed. As I stood there naked folding my clothes there was a knock at the door. Randy opened it and a tall, older man, dressed in a suit walked in. He smiled and shook Randy’s hand then looked across the room at me and said, “Nice.”

Randy took his coat and said, “You’re in for a treat. This guy gives amazing blowjobs.”

It felt strange and exciting to be naked in front of two fully clothed men, one of whom was a perfect stranger. It also felt really good to be complimented like that.

The stranger looked to be in his mid-50s. He had graying temples and a modest paunch. He suit was clearly tailored and his shoes, watchband, and belt all matched. He was clearly well-to-do and put-together. He walked towards me with a big smile on his face. His right hand reached out and aggressively grabbed my left nipple. I winced. With his left hand he brought my face to his and began kissing me passionately. His tongue was all over my mouth as his right hand dropped from by nipple around back to my ass.

I reached for his belt buckle with my hands and he stepped back. He firmly put a hand on my shoulder, and I got the impression he wanted me on my knees. As I knelt down, he unbuckled his belt and undid his trousers. He pushed them both down, revealing the most incredible cock I’d ever seen. His circumcised dick was only semi-hard and looked to be about 7 inches long. It was noticeably thicker than any cock I’d ever seen, and I knew it was going to feel weighty and impressive in my hands and mouth. He smelled rich and clean and I wasted no time. I took his cock into Eskort my mouth before it got any harder. I knew this would be the only time I could take it all, and I really wanted to. I warmed his beautiful member with my wet mouth and heard him utter a soft sigh of approval.

I began to bob back and forth on his hardening prick, never releasing my lips from their perfect seal. As he grew firmer and longer, I focused on breathing through my nose, working diligently to deepthroat this exquisite cock. I was making gobs of slippery saliva and the first taste of precum touched the tip of my tongue. Once he was rock hard, I pulled off and spat into my right hand. As I returned my thirsty lips to his magnificent dick, my right hand found my own hole. I applied our special mixture of my saliva and his precum liberally to my tight little butthole and began to probe myself with my middle finger.

Now that he was ramrod stiff, the handsome, well-dressed older man grabbed the back of my head and began thrusting into my mouth. I opened wide to accommodate him and he grunted approvingly. I was welcoming a second finger just pass the rim of my asshole when he spoke.

“Get ready to take this big load, boy.”

He pushed forward with a final thrust and unloaded. He wasn’t lying, it was a massive load. Big shots of cum filled my mouth faster than I could swallow, so I made the split-second decision to just hold it in my mouth. My handsome man shivered and pulled his spent cock from my lips. I looked up at him and opened my mouth, showing him his prodigious load. I winked and then closed my mouth and swallowed, all while holding eye contact.

He pulled up his trousers, tucked in his dress shirt, and buckled his belt. Randy brought him his suit coat and whispered, “I told you.”

The gentleman patted the top of my head and said, “I’ve got to get to church. Let’s do this again sexy boy.” And with that, he departed.

Randy looked down at me on my knees and smiled. “I thought you’d really like him. Such a great cock.”

I nodded in agreement, still savoring the giant load I had just earned. Then there was another knock at the door. Randy walked over and opened the door. He greeted a black man in an Amazon Prime delivery uniform. The man handed him a box and we locked eyes just over Randy’s shoulder.

“Damn!” said the delivery driver.

Randy turned around. They were both looking at me, naked, on my knees. Then Randy turned to the driver and said, “If you can cum quickly, he’ll give you a helluva blowjob.”

The driver didn’t miss a beat. He stepped past Randy and was opening his cargo shorts as he walked towards me. I had never seen a black cock in real life. I was eager AND a little scared at what he might be about to pull out and put in my face. What emerged was an average, cut cock. It was veiny, dark, and still flaccid. I rested my hands on his thighs and took him into my mouth with just my mouth, encircling him with my tongue. I loved feeling him grow full and then hard inside of my mouth. As soon as he was hard enough to suck, I went to work. Lots of suction and a quick pace. The delivery man breathed in through his teeth and let out an, “Oooooooh damn. Yes.”

I ran my hands up his thighs and under his shirt. I felt his firm abs and kept reaching upwards for his defined chest. With my hands no longer managing the space between us, the delivery man began to thrust his cock into me. He grabbed my head with his hand and held his cock all the way inside my mouth. I breathed through my nose, trying not to gag. He let go and I went back to sucking him, letting him know I was un-phased.

The delivery man was getting close. He whispered, “Lemme cum on your face. My girl won’t let me do that shit.”

I pulled my mouth from his cock and was going to grab his cock, but he grabbed his own cock, jacking himself furiously. He grabbed my head with his left hand said, “here it comes.”

The first jet of cum shot straight into my open mouth. With some salty jizz to taste, I closed my mouth giving the delivery man a full face to paint. He didn’t disappoint, shooting across my forehead and nose, my closed lips, and my left cheek.

“Damn that was hot.”

I squinted through a glob of warm jizz to see the Amazon driver leave.

Randy stepped into the restroom and returned with a warm washcloth.

“That was unexpected, but you were great. You ever been with a black man before?”

“No. That was a first.” I said, wiping my face clean.

“Well, it won’t be the last. You want some water?”

“I’m OK. I don’t’ want to wash away the cum taste.”

There was a timid tap at the door and Randy went to answer it. He opened the door, revealing a young man. He was fit and probably in his mid 20s. I’d never been with a younger man, as my fantasies and realities always involved older (richer, wiser) men.

Randy walked this young man to me and introduced us. “Seth, this is Frank. He’s my new married cocksucker and I need your honest feedback on his abilities.”

Seth smirked, “cool, let’s do this.”

Rather than fish out his cock as the other men had done, he began to undress. He quickly joined me in being fully nude. Randy’s eyes were as big as saucers and he had a huge grin on his face. Seth had a fairly large uncut cock and, like me, big balls. Seth waved his cock in my face and said, “Let’s see what you’ve got.”

I reached up and took him into my mouth. As he hardened, I removed my lips and used my hands to gently pull back his foreskin. When I looked up to see if Seth was enjoying it, I saw he and Randy passionately kissing each other. Seth was rubbing Randy’s crotch outside his jeans and they were making out hot and heavy. That sight made me really horny and I started sucking Seth assertively. I began to deepthroat him, gagging myself on his young, turgid, uncut dick. I helped myself to another handful of spit and precum and returned my fingers to my ass.

“Suck my nuts” I heard from above. I obeyed, lifting his cock skyward and opening my mouth wide to take his left testicle into my mouth. I then took the liberty to move past his scrotum and lick his taint. Seth separated his legs slightly, indicating he wanted me to continue. I moved my tongue to his hole, only to find Randy’s finger already there. This was hot. I was fingering myself and sucking a cock while watching two men make out and they guy whose cock I was sucking, was also getting fingered.

I was leaking precum all over my cock and the rug beneath my knees. I returned to sucking Seth, enjoying his young, energetic dick. Seth didn’t let on that he was close, or even warn me. He just came. His load wasn’t huge, and I kept his cum in my mouth. While he and Randy continued kissing, I spit Seth’s load into my right hand. I returned to my anus, lubing up my loosening hole with Seth’s fresh load of jizz.

There was another knock at the door and Randy broke his kiss with Seth to answer it. Seth looked at me and said, “Thanks man, that was hot. I’m gonna stay and see if Randy wants to fuck.”

Randy brought another handsome, older man into the room. He was wearing khakis, a blazer and a white button down. Randy introduced me to him. “Frank, you can get up. This is Beau. He’s my business partner. I showed him your video and he had a very special request.”

“Oh yeah?” I said with a grin.

Beau slowly took off his blazer and began unbuttoning his shirt. I helped Beau with his undressing, allowing his hands to gently run up and down my torso, grazing my buttocks. Beau looked to be in his mid-50s, similar in age to Randy. He smelled good and was clearly successful.

I kissed Beau. It was the first time I initiated a kiss with a man, and it was spine-tingling. He was a great kisser, better than my wife. I broke the kiss and said, “So I’m dying to know your special request.”

Beau pulled his pants and briefs down, freeing an unbelievably beautiful cock.

“I’m going to eat your ass while you blow me.”

Beau grabbed a pillow from the sofa and set it on the ground. He then laid down on his back with his head on his pillow. As I straddled Beau’s handsome naked body and lowered my ass down to his face, I debated whether or not to tell him I had rubbed Seth’s jizz into my hole. Before I could muster the words, Beau pulled my hips towards him and dove into my anus with his tongue. I could tell he tasted the cum and it only made him lick deeper and more passionately. I continued sitting up for a moment, enjoying someone’s attention on me and watching Beau’s fierce erection twitch before me. It looked too delicious to wait any longer. I bent over at the waist and took Beau into my mouth.

This was the perfect cock I’d longed to suck, and it was even more perfect from this angle. I could tell Beau loved it too. His body relaxed. Now that I was bent over, he spread my ass cheeks with his hands to drive his tongue deeper. Having such a skilled tongue work my hole while my mouth was full of cock was the most erotic sensation I’d ever felt. I could feel Beau’s stubble on my perineum, and it heightened the sensations even more.

As I got into a great rhythm deepthroating Beau’s cock, his legs spread apart and Seth’s mouth appeared below mine, licking and sucking Beau’s scrotum. I paused my cocksucking long enough to look up and see Randy entering Seth from behind. Beau was getting more vocal as two mouths ministered to his nether regions. I felt him tense up one last time and release a torrent of jizz into my mouth. It was a generous, warm, and well-deserved load. I held his salty gift in my mouth as he finished emptying his balls. I slowly pulled my lips off of Beau’s beautiful dick and looked up at Seth. His expression held such a sexy mixture of pain and pleasure. I leaned forward to kiss Seth and pushed Beau’s load into his mouth. He kissed me back, returning some jizz and we both swallowed.

Watching us kiss must’ve done the trick for Randy and he came aggressively inside of Seth’s tight young ass. Spent from cumming, Randy sat back on the ground. Seth excused himself to the restroom to clean up. I stood, still straddling Beau’s upper body. Beau spoke.

“You were right Randy. I think we should put him on payroll.”

“Ha!” Randy laughed. “I told you so.”

I didn’t know what they meant exactly, so I didn’t say anything. Seth returned from the restroom and he, Beau, and Randy all began to get dressed. I took a step towards my clothes but was chided.

“You’re not done. There are three more guys coming and it’s only 12:15.”

It had only been an hour and fifteen minutes and I’d sucked four cocks! I couldn’t believe I was going to suck seven cocks in one day. I stood by Randy’s desk and Seth and Beau both came to kiss me goodbye. Beau ran his left hand down my back and ran his middle finger down my crack, finding my sphincter and driving it inside me while he kissed me deeply.

Seth and Beau left, and Randy and I were alone again.

“I need your help” Randy said seriously. He pulled a roll of fabric out from under his desk and walked over to the restroom. He opened the door and stepped inside and unrolled the fabric. It was an opaque curtain on a curtain rod. There was a hole cut in the curtain.

“Come in here and help me hang this curtain rod above the door.”

I stepped inside and reached up to secure the curtain rod into two hooks. This set-up was clearly thought-through. There was a knock at the door and Randy smiled, pulled the curtain open, and stepped outside. I put the curtain back in place and turned off the bathroom light.

Randy barked, “Leave the light on!”

I did as instructed and turned the light back on. I heard Randy open the door. I heard soft voices but could not make out who was talking or what was being said. I heard footsteps approaching and looked down to see a chubby, flaccid cock poke through the hole in the curtain. I dropped to my knees and took it gently into my mouth. The chubby cock began to grow full as I made it feel warm and welcome inside my mouth. I had never been to a gloryhole before (on either side of the gloryhole) and this experience was incredibly hot. As his cock continued to harden it began to point skyward and I found myself bobbing up-and-down with the top of my head against the curtain where I could feel a large belly. I wondered, for a moment, if I was sucking off a fat guy.

“That’s it baby, suck my fat cock you whore. You want this cum you bitch?”

I continued to bob up and down and the big man began to grunt. Without any notice, a sour load squirted into my mouth. I swallowed it quickly, hoping the taste would go away. He finally stopped cumming and pulled out of the curtain.

I heard the big man say to Randy as he turned around, “Damn, man. Your wife sucks a mean cock.”

This guy thought he just got sucked off by a woman!

Randy said, “She sure does.” And showed him out the door.

I waited patiently in the bathroom, wondering just what Randy was up to. The curtain opened abruptly. Randy was smiling. “The last two flaked. You’re all done for today. Nice job. Hope you enjoyed it. Now get dressed and get out.”

I walked into the office to grab my clothes. As I bent over to collect them from the floor next to Randy’s desk, I felt his hand caress my ass and he uttered an approving moan.

“Did that guy think I was a woman?”

“Don’t worry about it.”

I quickly dressed, said goodbye, and left. It was 12:45 and I had another hour and 45 minutes based on what I told Charlotte. I thought I better go somewhere and work up a sweat so my alibi of yard work would hold water.

I drove to the track of a local high school. As I turned off the car, my phone buzzed. I looked down to see a text from Randy. I unlocked my phone to see a video. The still image was a close-up of my profile. There was a hidden camera in the bathroom that captured my anonymous blowjob in incredible detail. As I watched it, my cock stirred in my shorts. I quickly scanned the parking lot and pulled out my cock. I stroked furtively as I replayed the video with the volume turned up.

I came all over myself. I replied to Randy’s text.

“Today was so hot. Can’t wait until you need me again.”

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