A gay story: An Artist from the Past Auction result revives memories of my favorite artist
This is a “politician’s autobiography.” You all know what that means. Fact has been blended with fiction and dreamed aspiration. I have exaggerated some, but not much. Mostly I have changed names and places to protect the innocent. All portrayals of sexual activity involve people over 18. ©2024, Brunosden. All rights reserved.
I read yesterday that a few weeks ago, a painting by an American artist, Jerry Roper, was sold at auction in Berlin for just over $300,000 plus the buyer’s commission. This was a new high for works by the artist, now living back in the US. The article triggered fond memories from just over 20 years ago.
I’m no longer in the art business, but I still own several of Jerry’s earliest paintings from a time when I knew him well, and so I’ve followed his career.
I had graduated and gotten an MBA from an Ivy university. There was no active US war and the draft had long ago been abolished. So I was free to do as I pleased. I, like most of my class, accepted a job on Wall Street where business was booming; salaries were high; and, bonuses were even larger. We were, within a few months of reporting for work, part of the generation that considered itself kings (and there were a few queens—the female kind) of the universe. Through acquisitions and IPOs, we were changing the world, and making enormous profits for our firms and huge bonuses for ourselves.
I was technically bi, having experimented casually in college, and newly married—in what I later learned was an open marriage. But, frankly, I was working so hard, I was just about celibate. We lived in the same apartment and pursued our separate demanding careers. Marriage just seemed to be what everyone was doing, and I had known Marie for years. So we took the leap.
I worked incredible hours—this was the end of the heady time (for Wall Street) when foreign companies were bargain shopping in industrial America, and we on Wall Street were helping them to find treasures. Every deal meant another notch up in our bonuses. My average day started at 9 or earlier, after a long commute in from Jersey, and ended at 10 on a good day, after midnight when I was near a closing. And it was six or seven days a week.
Needless to say, my marriage suffered. I later learned that Marie (a dark-haired, Mediterranean beauty) had several guys on the side, serially not together! Quite simply, I was never home; we never vacationed; and, she was an attractive woman, often alone in hotels away from home. And given the adrenalin that my job produced, I was always horny, occasionally “handling” matters solo in a john stall midday so I could concentrate on work. I didn’t dare try to hook at the office, nor did I have the time to cruise.
In order to induce us to keep the late hours, in addition to end-of-year promised bonuses, the firm provided cars to take us home if we worked after 9. The office provided a buffet of sandwiches (to keep us at our desks). Then, there was a line-up of Town Cars outside the high rise office doors every night. We checked out with the duty security officer, picked up a chit and headed for a car.
Many of us had been liberals in college and felt a little guilty about the life we were leading and the results that we were achieving (the sale of America’s industrial base and the loss of American jobs). But, we swallowed our consciences or locked them securely in the attic and counted the money. One of the very small ways we assuaged our consciences was to ride in the front seat with the driver, rather than limo-like in the back. It was a small way of demonstrating “solidarity” with the people. I typically did this unless I left after midnight and wanted the extra hour of sleep in the back seat.
Thus I often struck up conversations with the drivers, particularly if they spoke English and seemed amenable to a conversation. Some of course had music plugged into their ears. When I spotted one of them, I entered the car through the back door and was soon snoring.
One of those nights resulted in one of my first extra-marital sexual encounters, and my first homosexual activity since college. The driver was a young black, well-dressed and well-spoken, probably Jamaican from the accent. He spoke with a deep mellifluous accent that we used to call a bedroom voice—like Harry Belafonte. I learned later that his father was a regular but had the flu. He was subbing to hold his Dad’s place in the valuable limo line. In the late dark of the Manhattan night, he looked like a handsome young buck. He had blindingly white teeth, a close shaved head and pecs that seemed to burst his uniform shirt. His black jacket was probably in the trunk. His hands on the wheel were enormous—and you know what they say about guys with big hands and feet. As was typical, the conversation between two young guys turned to football, then sex—specifically whether and with whom we were getting any and how we enjoyed it in bed. It was clear from the comments that he was a frequent flyer, maybe bi—or at least that he fucked men from time to time.
Not to belabor the point, I was horny and almost immediately threw a boner which was pretty obvious in my tight suit pants. I didn’t even bother to try to conceal it. He reached over, tapped my thigh, and when I didn’t protest, he grabbed it. I nearly creamed right then and there. I, in turn, responded by placing my hand on his thigh which inched toward his equally hard member. Fortunately, we weren’t far from my apartment by then. He was soon to become my first black cock—and my first man since college.
Marie was on a business trip, and the building was dark when we arrived in the Jersey suburb. (No kids yet.) I invited him in for a drink—and we both knew what that meant. He accepted readily, informing me that I was his last ride for the night, and that he intended to take the car home after his last ride. There wasn’t much doubt about the double entendre of the word “ride.”
We were only inside for a few seconds when he grabbed me and gave me my first kiss from a thick-lipped muscular, aggressive black man. He had rammed me against the wall as I shut the door and grabbed my ass hard with both hands, pulling our bodies together. He sucked so hard and attacked so ferociously with his tongue that I thought he was going to suck the soul out of me. (Actually, he did take my soul, but that’s another story.)
Finally he released and I led the way to the bedroom, removing clothes as I went. We were both soon naked and in my bed. I was a little disappointed. I had heard so much about BBCs that I assumed they were ubiquitous. Not so. He was just a little larger than my 7 1/2, but cut where I was hooded, and thick where mine was thin—”aristocratic, in my wife’s words.” But, it looked great on his muscular body—particularly the swollen dark head and the slight curve of the shaft resting on enormous balls.
Even after all these years, I can still picture the scene. He wasn’t a great lover. Not much foreplay. I was on my belly within a few minutes. He was wrapped and inside within a minute or two after that. But I was already at the edge and welcomed him readily. He did a bit of prep with lubed long strong fingers, easily locating and punching my prostate until I was moaning for him to put it in. He finally pulled me up so my ass was pointed in the right direction, mounted my ass doggie-style. I can still remember the sting and the pain. It had been a long time. He didn’t pause, but in less than a minute the waves of pleasure overcame any feelings of pain.
He began a strong series of long strokes as his large hands cupped my balls and stroked my rock hard shaft to hold me in place. He wasn’t into slow slides. It was all bulling in, hard and deep. I felt full and good. I wanted that cock inside me. It had been years since I had been fucked by a man—and days since I had slept with my wife. He re-awakened the pleasures of man on man sex, and I quickly was ready to blast. A big strong bull was taking me to a place that I had nearly forgotten existed since college.
His muscled chest touched my back as he humped deeper and deeper. The announcement of his cuming (in that deep Jamaican, “I’m a cumin, maan. I’m gonna fill you with a load of my baby-makers.”), the final thrust, the accompanying squeeze of my balls and the feeling of his hot stuff filling the condom bulb set me off. I hadn’t been so aroused in years.
I actually felt the semen flowing up my shaft—an incredibly pleasurable wave of sexual energy, maybe because he was squeezing it so hard. It turned out to be one of the best orgasms and biggest loads that I had dumped in months. I shot a half dozen times soaking the sheet as my semen leaked though his fingers. He pumped a few more times until I had the feeling he was pumping dry. Just making sure that his conquest was duly planted and full. Then, he fell on top and left his still hard dick deep inside. His hand left my dick as he fed me the cum that coated his fingers. It felt terrific to experience the strength, weight and violence of man-sex with a power top. Then, it was over. He quickly rose, dressed and was gone. I didn’t even get his name. But I did sleep well that night, and my dreams were lurid re-enactments of man on man sex.
I’d like to say that experience became a routine, but it didn’t unfortunately. Most of my drivers were old enough to be my father or grandfather. In fact over two years, there was only one other. And all he did was let me blow him in the front seat. But, I had renewed my interest in men. I was ready to cruise, but really didn’t have the time or the opportunity.
*****
Fast forward about 8 years. My wife and I divorced after three years of marriage. She got the apartment (it was a rental at a good lease rate with two years left) and its furnishings, but there was no alimony. She made almost as much as I did. I finally left the investment banking firm after six grueling years—with a good-sized nest egg, and I took a job as CFO of a medium-sized New York start-up. I moved to a condo in Ft. Grant and tried to restart my life. My hours became human. I started back at the gym. I was running again on weekend mornings. And I dated a bit.
I should back-up here and tell you a little about me. By that time I was 35. I was medium everything—about 5-11, light brown hair (sun tipped after a beach vacation, but not otherwise), hazel eyes, reasonably handsome, but not a show stopper. I had rowed and run in college and after eight years of office work, my body had gone to seed. A rigid gym schedule and weekend runs had restored my slim physique and my long lithe muscles. I was by no means a body builder, but was quite proud of my hard pecs and six pac.
I did some cruising in New York at the gym, but nothing really worked. Then I tried a club in the Village and hooked up with a pretty nice guy who was in the art world. “In the art world” meant that he was a sales rep for a first tier East Village gallery. He wasn’t an artist. Nor was he a gallery owner. Within a month or so, we were spending weekends at my place. I got to top mostly and learned it was my thing. He was the sort of guy that I had played with in college—about my size, with a little smaller dick than mine, similar build, well-dressed, well-spoken—a preppy sort of not-too-serious guy who had never played sports, but ran and worked out regularly. He became my bottom on a pretty regular basis. We were better friends than lovers. But, I liked having him around. And he was a reasonably good lay. He was available with no strings attached. On one of the weekends, he led me to discover an art colony of sorts—only two blocks from my condo.
Ft. Grant had originally been a bedroom community for New York with young families and lots of kids. They had built schools—many of them. But with the passage of time, the families moved west; high rise condos took the place of many neighborhoods; and, the kids disappeared. This left empty schools. One forward-looking borough selectman was an art lover and convinced the city to turn one of the elementary schools into art studios—working studios that would be open to the public on weekends.
A competition was held and I got to be one of the selection jurors. (Oh, I forgot to mention: my partner had convinced me to invest in the gallery he worked in when it was near bankruptcy. So I was a 50% owner of an East Village gallery, located on the first floor of an old brownstone. Nothing much then. Later probably the second best gallery for up and coming international artists after Gogosian’s.)
It was through this series of events that I met Jerry Roper, one of the first 16 artists-in-residence. I had interviewed him and liked him a lot. We hit it off the first time we met.
Jerry was a strange character. He was an Amherst graduate, but immediately after graduation had gone to live with a group of hippies on a farm in Vermont and lost the next several years of his life to drugs. He had been “liberated” by doting parents, cleaned up and begun to paint. Jerry was about 5-6, with dark, almost black hair, bushy eyebrows over bright, lively blue-almost-purple eyes, light skinned and thin, really thin.
I liked his early work—mostly photo-realism, a movement which was just about to leave the fickle New York commercial art scene—and really good. He was extremely talented and apparently a little haunted by his past. He had become a vegan, a teetotaler, a non-smoker and a health nut. He ran 10 miles each day (an activity that I began to join him on Saturdays and Sundays within a month), and, during the first months I knew him, he began to bulk up. I was partly responsible.
We met often and I usually brought him a bag of groceries. He always looked so hungry! At about this time, my art gallery partner found someone he liked more than me, and left the gallery and me with two days notice. Our four month “affair” was over. So now I owned half a gallery and had no one on the scene on a regular basis. So I redoubled my involvement and started helping with shows and receptions.
Usually when I would visit Jerry, he was painting with live models. He had fallen in love with and painted only the beautiful human form—women and men. So his models were typically posed nude in the studio when I would arrive. He would often keep painting for some time as I sat and watched. Over a few weeks, I began to realize that Jerry was obviously interested in the human form—but only insofar as it gave him the opportunity to engage in social commentary, specifically the dark side of casual sex and sex for hire. Two models became three, then four, then a group. Thrift shop purchases had added faux-Tiffany lamps, fur throws, Victorian furniture, old silver pots, large fake palms and similar items—creating the backdrop of the decadent “Beau Monde” vibe of his oils And the sex he was painting began to show full frontal nude males, erect penises, threesomes and orgies. Not the stuff for church art shows, art-in-the-park or thrift sales!
But, it was good. Really good.
One night after the models all left, it was clear than Jerry was incredibly horned. He invited me to go clubbing with him. And I responded by inviting him back to my nearby condo. Thus, we started a several year affair.
Jerry was nothing short of stupendous in bed. He was a confirmed top. And despite his diminutive stature, he had one of the biggest cocks I’ve ever seen in my life: about 4 inches flaccid, but it was definitely a grower—probably to 9 or 10 inches when rock hard.
On the first “date” I had a drink (and he had Pellegrino with lemon) and we sat on the sofa of my condo which looked out on the Manhattan skyline. We started necking. Soon I pulled him into my lap—he was the perfect size. Clothes were discarded, and our chests came together as his arms stretched around my neck. So naturally, my free hand began the massage of his cheeks, the exploration of his cleft, and the stimulation of his rim. I have always been an ass man. Both of us were rising in temperature and arousal. Then, Jerry whispered that he was a confirmed top. I told him I was okay with that “for now” but that we’d have to revisit that situation if “things worked out between us.”
We headed to my bed—and it was then that I realized what an Olympic grower he was. His stiff cock was barely perpendicular to his body because it was so heavy. The head had reddened and enlarged. He was going to pound the fuck out of my chute and my prostate with that baton. At that point I was re-assessing my agreement to bottom, but that cock looked so good as it darkened threateningly and started to leak.
I pulled him by his cock to the edge of the bed and pointed to the magnums and lube that were on the bedside table. Then, I turned and fell in, belly first. I drew in my legs and I lifted my ass toward him and moaned, “Take it slow and use a lot of lube. You’re bigger than anyone I’ve ever taken, Jerry.”
He took his time wrapping and lubing. “I’m really enjoying the view, Mac. I’m going to paint that ass sometime. It deserves to be immortalized. But first it needs to feel a giant dick.” Then he bent over me and touched his chest to my back as his fingers began to do their work. It turns out that painter’s hands and fingers are pretty good at foreplay and opening—must be the precision practice they get from careful brush strokes. Soon he had at least three fingers inside, turning and swirling, and I was groaning in anticipation and invitation. He slapped my butt a few times and then moved to my nipples to distract me from the invasion.
He positioned, applied some pressure and the head popped. Fuck it stung. But the sting soon faded and I signaled for him to continue. It took several minutes of bumping, thrusting and withdrawing before he bottomed and I felt his hot, swollen balls colliding with mine. Again he paused, but distracted me again by reaching around and teasing my ultra-sensitive nipples into erection. Then he flattened his hands on my pecs and drew me into his lap. I couldn’t believe how deep he had gone. I swear he was in my gut, and that I could see the head just under my belly button. I was panting with desire. My eyes were dilating. And I could definitely feel his girth inside my chute which had stretched to accommodate him. Fuck he felt so good!
Jerry began his vigorous fuck with alternating long slow thrusts and short hard jabs—which always targeted and usually hit my prostate. He continued for what seemed a long time but was probably only a few minutes. But during that time my arousal was reaching the crest of the hill. I called out my impending climax, but he probably already knew. He had strangled me twice to prolong our mutual pleasure. My precum was pooling in the palm of the hand that he was using to retract my hood so his fingers could brush the glans. I jolted back from the sensitivity and pushed hard into his lap. That of course drove him as deeply inside me as anyone had ever been—or has been since. He sped up and I felt his spasms. And I responded with jerks of my own. I shot an enormous load in a half dozen shots. I was totally spent, but still anxious to have him on top. Then he fell on top of me, and we collapsed onto the bed.
“Fuck. I needed that,” he whispered as his lips touched just below my ear lobes. Then he brought his fingers to his mouth and sucked each in turn, tasting my cum.
“So did I. So did I, Jerry. I love having your giant tool inside me. No one has ever done me better.”
He ended up spending the night. And, although Jerry was a top, it turned out that he enjoyed being spooned afterwards. So we slept with him in my arms. He fucked me twice more that night: in the middle of the night and early the next morning before our run. Each time was a gold medal performance, longer and more athletic than the one before. And by morning, I could barely rise from the bed. Fortunately it was Sunday. The hell with the run.
Given how close his studio was to my condo, we repeated often in the next few weeks. (I learned that he had been sleeping on the old Victorian couch in his studio—strictly against the no-residency policies of the building—and using the old children’s bath to wash up. As a grammar school, it had no shower, so he had been sponging off for weeks at the tiny knee-height sinks.) Within a month he had moved in, and we often showered together. He loved having my fingers deep in his hole, teasing his prostate. He liked to be finger fucked, but rarely did he actually bottom.
Given his artistic nature and attitude, we were nude usually in the condo. And we couldn’t get enough sex. He would return from a day painting beautiful nude men and women, often feigning sexual activity. That always turned him on, and I suspect he may have relieved himself more than once during the day. But he was indefatigable. He was ready always. Only I demanded a bit of foreplay. Ultimately, I cajoled him into letting me top. And I can say without question, looking back on that time, that he was the most active and dominant bottom that I’ve ever had at the business end of my cock. We did it a few more times, and he was beginning to enjoy it, I thought. Certainly he came to appreciate and love the ass play that I used to arouse him in foreplay.
In all we had about six months of the most intense sex of my life. But, we both knew it wasn’t love. It was pure lust. A chance to experiment with the most exotic dreams that we had ever had about sex.
Once I arrived home to find him fucking in our bed. She was an incredibly gorgeous blonde woman—with blonde ringlets almost to her waist, full rounded breasts and long legs ending in one of the most spectacular pear-shaped asses I’ve ever seen. He motioned me to the bed and arched his eyes in question. I stripped and took his ass while he pumped her. She loved it. And I think he loved it. He was willing to bottom for me so long as his dick was buried deep inside a woman. It was an experience I will never forget.
Another time it was a man, or rather a boy, probably just out of high school and just barely legal. He was a swimmer and diver with long stringy muscles, an incredibly small tight ass, and of course a big dick, with a snow white complexion and blonde hair. (Jerry tended to like to paint curly blondes for some reason. He had absolutely perfected the brush strokes which created highlights on the tips and outsides of the tight curls.) He pulled out and motioned me to plunge. I did and, as I was stroking, I felt his monster knocking at my back door. It didn’t take long. By then, I was becoming accustomed to his size and impatience. He plunged, filling me like always, crowding my prostate like always and started stroking. We got into an incredible synergistic tempo as I fucked and was fucked. Finally, I exploded as the young guy orgasmed and his ass muscles squeezed my dick. And of course my own explosion began the milking of Jerry’s horse dick.
Toward the end of our time together, I arranged for a show of his work at the East Village gallery. He exhibited more than a dozen realistic, nearly life size scenes of intimate hetero sex, homo sex and orgies. In the largest, there were eight figures, all acting like it was an everyday part of their lives: drinking, smoking (what was obviously weed) and stroking each other. Two couples, one hetero, one homosexual, were in full intercourse. The others barely seemed to notice. In fact all the characters appeared to be incredibly bored by the whole thing.
The show was a smash—although the major critics didn’t use photos of the work in their reviews. Jerry was not only an accomplished “photo-realist” but also a social commentator. The liberal press loved it. And every painting sold opening night—three to museums.
I didn’t realize it at the time, but that was the beginning of the end of our relationship. Jerry had money now. He didn’t like any feeling of dependence. And he definitely was not monogamous (“an invention of the female side of bourgeois society”.) Jerry started bringing home partners almost every night—even when I was away on business.
Several months later, he told me, after fucking the shit out of me for nearly an hour, that he was moving out. He had enough money and wanted some “independence.”
I didn’t protest. I knew it was coming. We had a few dates after he moved out the following week, but we started drifting apart.
My gallery gave him two more shows. They were both successful. And I bought three of the paintings. He never did paint me.
A few years later, I married again, and we now have two kids. She’s well-educated, beautiful and a very good mother to our two boys—now both in school. I had always wanted kids, and these two boys became my life. We are happy, and we typically find occasion to have sex a few times a week, maybe a little more often when we take winter Caribbean vacations. We moved to the burbs. I sold the gallery for an enormous price—to a developer who was going to combine it with other properties and build a mid-rise condo. And ultimately I became CEO of the start-up I had joined many years before.
About this time, my wife convinced me I needed another intellectual track in my life, and at her suggestion, I enrolled in PhD studies. A few years later it was Dr. MacIntosh. I had enough money. So I quit my CEO job, took a golden parachute and signed on as an Assistant Prof at a southern university. Julie and the kids moved with me. But our lives were never the same again. Our marriage had simply fizzled out. We had occasional sex, but I’m pretty sure that she knew I wasn’t there. I was pretty sure she knew I was bi and that I had occasional guys, but she never mentioned a word. We stayed together for the kids.
I never seduced one of my students. That was an absolute NO. But there were three universities in our town, and through social media, I signed on to “tutor” athletes at the other schools—mostly test prep and assistance with term papers. More than a few paid me with a willing or semi-reluctant fuck on my office sofa. Oh the wonders of “transactional” sex with a new generation!
I continued to follow Jerry’s career, but not too closely. I was busy and very happy in academe, often hosting students (not mine) on my couch. Jerry moved to Miami after a few years, seduced by a big international gallery with a large foreign clientele (which apparently was much less squeamish than Americans were with male full-frontal nudity, orgies and vivid portrayals of foreplay and intercourse.
Then it was Berlin. I knew he was a success in Europe, but didn’t have the details. A few years later, I heard he had married and was living in California with an heiress. I had to assume she had either tamed him or permitted him to have discrete liaisons on the side. He had always be a pan-sexual. There were a few museum shows, but except for Miami, none in the South. All were rated X. One or two were actually picketed and closed early. (Great publicity for an artist.) Children under 18 were not permitted without parental supervision. Jerry had become the archetypal painter of the high class free love movement. The works were beautiful, but deeply cynical, often described as the “Eurotrash community in Miami.” Some people just love having their life styles shat upon. And most of his paintings ended up in master bedrooms, rather than gallery walls.
But, today as I read the story of the auction in Europe, I was prompted to remember the very good nights we had together for almost a year. Jerry was certainly one of the loves of my life. I’ve never had a bigger dick inside me; never had more talented fingers stroking my stuff and diddling my nipples; never had more powerful orgasms. He was simply the embodiment of sex—sex on a paintbrush, so to speak. And I certainly had the best sex with him that I’ve ever had—before or since.
I think maybe I’m going to try some clubbing in the next couple of days. I’m still young enough to attract some of the best. BD
This is a quick piece that I typed off in a few hours after reading the article referred to in the first paragraph. I often wonder what my life would have been like if I hadn’t taken a second wife, had children and let Jerry get away. I guess I’ll never know. Sorry there’s no HEA, but this is my life after all.