Finally Caught Up with Me

It was my 38th birthday and I was really excited to have a few hours of "me time" at my friend Randy's. Randy was about 15 years my senior. He was my type to a T. Older, wiser, richer, and married. I've had a thing for older men ever since I started fooling around with guys on the down low. That's right. I'm "straight". I've only dated women and I am married to a woman, but going back to college, I've quietly hooked up with older, married men whenever there was chemistry, trust, and a safe place to play.

I sucked my first cock when I was 19. That cock belonged to a 47-year-old attorney who went to my church. We "found" each other in a chat room and after a few months of chatting arranged to meet. It was surprising and extremely HOT to find out we knew each other. I didn't know what I was doing, but I had been on the receiving end of enough blow jobs from girls that I figured I could manage. As it turns out, when I wrapped my lips around that first cock and felt it grow hard inside my warm, wet mouth, I knew I had found my calling. I was a cocksucker.

As I moved around the country after college and throughout my 20s, I always managed to seek out and find one or two trustworthy and discreet older, married men to fool around with, all while publicly dating women and outwardly presenting as straight. I eventually met and married my wife Charlotte when we were both in our early 30s and we settled down in Nashville, TN. My cock sucking prowess was not something I shared with Charlotte. She is rather prim and proper and (right or wrong) I figured it was best to keep the two worlds separate.

Once we settled into Nashville, I started looking for playmates. The first friend I found was Bo. Bo is a very handsome and successful architect and a little more than a decade older than me. We connected on an app and hit it off. We were both each other's type. I liked 'em older and successful. He liked 'em young and thirsty. One Saturday night, when my wife was out of town on a girls' trip, Bo made an excuse to get out of his house and snuck into our secluded garden/side yard.

I was feeling bold and horny, so I met him outside completely nude. I immediately dropped to my knees, pulled his shorts and briefs down and engulfed his gorgeous cock. Bo is handsome and fit, and his cock is beautiful. I was in heaven. It had been well over a year since I had sucked a dick and Bo's was a magnificent one to suck. When Bo warned me he was about to climax, I pulled off of his cock, opened my mouth, and let him paint my face with a prodigious load of cum. Spurt after spurt hitting my open mouth, my cheeks, my chin, nose, and eyes. Bo quickly pulled up his shorts and disappeared through the garden gate and I just stayed on my knees, enjoying the cool night air on my naked body and let his cum drip down my face.

Bo and I tried to get together frequently but had more misses than hits. Always tricky for 2 married men to find a safe place to play and for schedules to align.

About a month after Bo's very memorable facial in my yard, I struck up a chat message with J.D. J.D. is a lead, systems engineer for a medical laboratory in town. He also has a very private office and a rather thick cock. I had long fantasized about blowing an older man in his office, and J.D. fulfilled that for me. I had to make an appointment so his secretary wouldn't suspect anything. J.D. ushered me into his office and closed and locked the door. He told me to undress completely and I did. He slowly walked around me, inspecting me with his hands and eyes. It felt like he was judging me and it was turning me ON!

He walked over to his big leather desk chair unzipped his trousers and sat down. He beckoned and I came, dropping to my knees and eagerly fishing a rather meaty and substantial cock from his trousers. His thick cock grew hard quite quickly in my mouth and it became apparent he was going to be a fast cummer. I slowed down, trying to delay his orgasm, but it was to no avail. He exploded into my mouth, stifling his moans and firmly placing his hands behind my head so I couldn't pull off his cock. I enjoyed every drop of his pent-up load and made sure everything stayed in my mouth and not on his trousers.

J.D was equal parts impressed and grateful and I was in heaven. We continued our "lunch meetings" on a weekly basis until budget cuts forced him to share his office with two other engineers. That put an abrupt end to our fooling around.

It took me several months to find another suitable fellow. One day Randy sent me a wink and I opened his profile. He was handsome, he was older, he was clearly successful, and he had a gorgeous cock he wanted sucked. Randy, it turned out, had a private home office with its own entrance from the outside. He messaged me his address and that he had a 5-day load. I was out the door in a flash. Randy's cock was the smallest yet, which is to say it was average in length. I quite liked the size as it meant I could easily deep-throat him.

Randy was also the most vocal gent I had ever blown. He moaned and grunted and talked dirty to me throughout the longest blowjob I'd ever given.

At about the 20-minute mark, when I was sure my jaw and tongue were about to give out from ministering to his cock, balls, taint, and asshole, he let me know he was close.

Randy breathlessly told me "let me cum on your ass."

I dutifully obliged, turning onto all fours, resting my head on the ground, and pointing my ass up in the air. I reached back to spread my cheeks just in time to hear a loud, guttural grunt and feel a squirt of warm jizz splash down my ass crack. I fingered my hole with his first cum shot while he emptied that majestic 5-day load all over my back and bum.

Randy brought me a warm, wet washcloth and as I was quickly getting dressed to dash out, he invited me to stay. He offered me a beer and began to ask questions about me. This was the first time my hookup wasn't just a quickie. I stayed for an hour, getting to know Randy, sharing my goals, my wants, my fears, and my regrets.

As I departed his office that day, he placed his hand on my shoulder and simply said, "Thank you. You are wonderful."

This guy made me feel good.

Randy and I continued to chat online, sometimes for the better part of an entire workday. We shared our fantasies. Mine was to suck 2 cocks. He asked me how long I'd lived in Nashville and who else on the app I had hooked up with. I shared a few of my dalliances with him, really bragging more than anything. I wanted him to know I was desired and experienced. We would look at profiles together and share our thoughts of different guys' bodies and cocks.

Randy suggested another hook-up at his home office and I JUMPED at the chance. I arrived and he asked me to smiled deviously and said he had a surprise for me. He told me to get undressed and that he was going to put a blindfold on me. Once I was blindfolded and nude, he told me to get on my knees. And wait.

I sheepishly said to him, ''please no cameras or video, ok?"

He replied reassuringly, "Of course not."

I heard a door open behind me and heard steps approaching. Then I heard kissing sounds and unzipping sounds. I don't know why I left the blindfold on, but I did. I'm eager to please, what can I say?

Then I felt a hand on the top of my head, and I heard Randy say, "Open up."

I did. And a thick, hard cock that was NOT Randy's entered my mouth. I ripped off my blindfold and looked up to see J.D. standing over me. He and Randy smiled and laughed. My heart was racing, but I was so happy to see his gorgeous cock. I held his eye contact as I took him back into my mouth. He turned to Randy, who walked up next to him and they began to kiss.

I pulled my lips off of J.D. and took Randy into my already warmed-up mouth. To feel two totally different cocks was an incredible turn-on. I sucked Randy till he was rock hard and then went back to J.D. He had grown rock hard from kissing Randy and watching me give another man a blowjob right in front of him. I remembered that J.D. was a fast cummer and could feel him already tensing up as I ran my hands around his ass and thighs.

J.D. broke off a kiss with Randy just in time to tell me he was cumming. His load was prodigious. I tried to hold all of it in my mouth as he emptied his balls. Once he finally stopped, I carefully pulled my lips from his cock and looked up at both men. I slowly opened my mouth and used my tongue to lift J.D.'s load for both men to see. Then I swallowed it all in one big gulp and returned to Randy's cock.

It was remarkably easy to deepthroat Randy after loosening my jaw to take J.D.'s manhood. I was highly sexually charged and went after Randy's cock with focus. I grabbed Randy's buttocks and pulled him completely into my face, letting his cock tickle the back of my throat. He quickly pushed me off, not wanting to cum just yet. Then he went over to J.D. who had sat down in the big leather chair to rest. He whispered something in his ear and J.D. grinned. Randy walked back towards me and put his cock back in my mouth. As I resumed sucking him, I saw J.D. move behind Randy and kneel down. J.D. placed his hands over my hands on Randy's ass cheeks and helped me spread them. I got the hint and held Randy open while J.D. tongued his asshole.

Randy was in heaven. His moans grew louder with me deepthroating his cock and J.D. tongue fucking his rosebud. We were in a nice rhythm and it was really hot. I was fingering myself with a mixture of precum and saliva and my cock was about to explode without me even touching it.

Randy quickly pulled out of my mouth and I thought it was to give me a facial. He turned around and J.D. got down on his hands and knees and pointed his ass up at Randy. Randy stroked himself to a climax and spewed jet after jet of hot, sticky jizz on J.D.'s hole and crack. When he had finished cumming, he grabbed me by the scruff of my neck and shoved my face into J.D.'s ass.

"Clean him up."

I dutifully lapped up all of Randy's jizz, allowing my tongue to do a bit more than the job required. I reached between J.D.'s legs and stroked his cock as I tongued his cum-covered hole and lovingly licked up and down his ass crack.

About a week after our group play, Randy messaged me saying he had a 4-day load and could host if I came over right away. I left the office and drove over, nervous and excited. Randy led me into his office and we immediately began making out. We both started removing each other's clothes as fast as we could while still keeping our lips locked together.

I should take a moment to note, to this point, I'd never kissed a man before. I'd probably given head to 30 different guys since college, but I had never locked lips with one. It was hotter than I expected and more forceful than a woman's kiss.

Randy sat himself down on a big, comfy leather chair in his office and laid back. I dropped to my knees and slowly crawled towards him, wiggling my ass as I went. I came up between his legs and took his already rock-hard cock deep into my desperate mouth. He let out a sigh as I took his full length all the way in.

After a solid 10 minutes of my very best cock sucking, I was getting a bit weary. I began to finger myself with my saliva and his precum and hoped Randy would cum soon. To try and speed things up, I rose from my knees and placed my lips over his left nipple. I gently licked it before nibbling it with my front teeth. This jolted Randy and he abruptly stood with a kind of growl. Up from his leather chair, he walked around behind me suddenly grabbing the back of my neck and forcing me forward into the seat cushion of his chair. As he held my head down with his left hand, he used his right hand to point his dick right at my hole.

He pressed his cockhead inside of me abruptly then slowly pushed the full length of his cock in my ass. Once in all the way, he pulled out and began ramming mercilessly into my virgin hole. He got off just 5 or 6 thrusts before he unloaded deep inside of me. It seemed like he just kept cumming and cumming as he pushed my head further into the chair. I was in pain and I was kind of turned on and I was scared. Before Randy stayed inside me as he slouched over my back, out of breath. Just then, his office door open and in walked J.D.

"You couldn't wait until I got here to fuck him?"

Randy pulled his cock out of my ass and said, "He was sucking me so good and I could see him fingering himself. When he bit my nipple, I couldn't contain myself.

"Did you breed him?"

Randy bragged, "I just dumped a 4-day load inside of him."

J.D. looked at me and said, "Get on your back."

I told him I needed to go to the bathroom. I'm sure I looked as scared as I felt.

J.D. said, "You're not going anywhere. Get on your back. NOW!"

I sat down and lowered myself onto my back. J.D. stood over me, fishing his magnificent cock out of his pants. He separated my legs and knelt down between them. He picked my weak legs up and pushed my knees back to my chest. He looked down at my ass and saw Randy's cum dripping out and grinned. He snorted loudly and then spat on my taint and hole and pushed his cockhead against me.

Unlike Randy, J.D. went slow. She was very patient, waiting for my hole to adjust to his manhood with each millimeter of depth. When J.D. finally bottomed out inside of me, I opened my mouth and eyes as wide as I could. I couldn't make any sounds or words, but the sensation was incredible.

J.D. brought his lips to mine and kissed me deeply as he began to pull his cock slowly back out. I kissed him back. He was a better kisser than Randy. Even though I was in severe pain, I was incredibly turned on. As J.D. and I kissed, my body relaxed and he began to move in and out of me in smooth, even strokes. I could feel every inch of J.D. and all the slippery jizz lubricating his magnificent cock.

As I began to lose myself in this incredible moment, I wrapped my legs around J.D. I stretched my arms up above me and arched my back. I thought for a split second about my wife and the fact that I was laying down how she lays when I'm fucking her. Then I thought about how I look down at my wife as I thrust in and out of her and how J.D. seemed like me.

I was snapped out of my daze by the door opening. I broke the kiss with J.D. and looked over his shoulder to see Bo walk through the door. He looked down at me and said, "Oh fuck yes."

Bo quickly stripped naked and straddled my face. He pushed his hole into my face and ground back and forth on my nose and tongue. I tried to both breathe and please Bo while J.D. continued fucking me.

"Get him up on all fours." Randy said from the other side of the room. I didn't even look at him. J.D. pulled out of me and Bo stood up.

Bo suggested that he and J.D. switch. I was with it enough to know I didn't want to taste my ass on J.D.'s cock so I pleaded with Bo to let J.D. finish fucking me. He agreed but told J.D. to hurry up. The men helped me up on my hands and knees and J.D. grabbed my hips and slipped right back inside me.

Bo put his hard cock in front of my mouth and I thirstily took it. Watching me suck Bo was just what J.D. needed and he grabbed my hips more firmly as he tensed up and came in my ass. I kept sucking Bo and I was flashing back to our first night in the garden. He snapped me out of my daydream when he said, "Sit on my dick. It's my turn."

Bo laid down on his back and I crawled up till my ass was just above his cock.

"Kiss me while you stick it in your ass."

I leaned forward to kiss Bo and reached back between my legs for his cock. I pointed it towards my ass and was surprised at how easily I slid back onto his cock. I closed my eyes and kissed Bo as I wiggled my cum-drenched ass back and forth on his dick. He said, "Sit up so I can look at you."

I obeyed and sat up. I immediately felt hyper sexualized. I had done this plenty of times with my wife, wanting to watch her grind on my cock so I could see her tits and watch her moan. I immediately knew what Bo wanted and decided to play the role. I tiled my head back and ran a hand over his chest. I pinched one of my nipples and arched my back, letting little moans of pleasure out as I slid back and forth on his cock.

Bo was getting close. He sat up so we were face to face and he kissed me deeply as I bounced up and down on his dick. His breath quickened and without saying anything he squeezed our bodies together and came inside me. A bit wobbly, I stood up and felt the cum dripping out of me.

I caught J.D. out of the corner of my eye come back towards me. He bent over and put his ass up in the air. I immediately started stroking my sore and engorged cock. I came in less than 10 seconds and it was the biggest load I've ever shot. I got most of it on J.D.'s hole and ass crack and shot more up his lower back.

"Clean him up." I heard Randy say.

I had never tasted my own cum. I knelt down and took a hesitant taste. It tasted like cum, so I went for it. Once again, I was licking jizz off of J.D.'s ass, it was just that it was my jizz this time.

"Goddamn boy what an ass".

Randy offered me a warm wet washcloth and pointed me towards the restroom attached to his office. I obviously hadn't gone over with the intention of having anal sex and therefore was completely unprepared. I'm sure my ass was disgusting and needed to be cleaned up.

I sat down on the toilet to let three massive loads drip out of me and tried to compose myself. I cleaned myself up and emerged feeling sheepish and very naked. Bo and J.D. had left while I was in the bathroom. Randy handed me my things and said he had to hop on a conference call. He ushered me out the door quickly.

I drove around for a while before heading back to the office. I was in shock. Just then, my phone buzzed.

It was from a local 615 number, but I did not know who. I opened it up to see it was a video. I pulled the car over and put it in park. I looked around and pressed play.

I saw myself lying on my back and J.D. entering me. I watched until the end. The video ended and the screen froze with me, on my knees, licking (my) jizz off of J.D.'s ass. Randy had filmed me from just a few feet away and I was too oblivious to realize it.

My phone buzzed again. It was a text message from the same number.

"I snagged your wife's number from your phone. If you don't take care of us when we need you, she'll get this video...and the others."

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