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.
