What a Life

By John the Artist

Published on Mar 7, 2021

Gay

This is the fictional memoir of a gay man, told in the first person. Some of the stories in this series are based on actual experiences, usually embellished a lot, as well as completely fictional ones. They depict sex between consenting adult males. If this offends you, do not read them. These are my stories. Please respect the copyright. If you enjoy them, let me know at johntheartist@hotmail.com. Please Contribute to Nifty.org and keep this wonderful resource going!

This is the third in a series of books that began with C'est La Vie! (1970-1997), and continued with One Thousand Men (1998). Th stories in this book start in 1999 and continue to the present. I hope you like them!

What A Life! 6

2003, Cock Robin 3

While Jason went back to his room to get his things, I wrapped a towel around my waist and opened a bottle of white wine, got out two glasses. When he returned a few minutes later he said, "I walked in on Paul fucking Robin. I was a little embarrassed, but Paul paused for a minute and said it was OK, to get what I needed and that they would love to have a four-way tomorrow. I responded, Cool, that would be great, we'll talk in the morning."

"Sounds like fun," I said to Jason, "I would love to see you fuck Robin while I fuck Paul."

He answered with a nod and a big smile while I poured a glass of wine and handed it to him. "So, Jason, tell me about yourself."

"What do you want to know?" he asked.

"Your age, where and how you grew up, what your hopes and dreams are, you know, stuff like that. You are a fantastic partner in bed, but I think there is a lot more to you than just that."

"Well, John, I grew up in a small town in northern Michigan. I'm a upper'--pronounced you-per'. I'm 23. My father is a real estate broker and my mom is an elementary school teacher. I have two brothers, 20 and 16. I played football and baseball in high school. It was a small school, and though I knew I was gay by the time I was 12 or 13, I suffered through, thinking that I would be an outcast if kids knew. I compensated by being a jock, and a good one at that. I dated girls because I was supposed to, and even had sex with a couple of them--fantasizing about having sex with men--was the varsity quarterback and played shortstop on the varsity baseball team. During my senior year I did have a boyfriend, but we both were scared shitless that we would be found out. It's a long story about how we figured out that the other was gay, and it was only a pilfered bottle of Jim Beam that loosened us up enough to explore our mutual desires. We used to suck each other off and masturbate each other. Anal sex seemed too gross--we did not know about douching your ass or stuff like that--and so I did not experience anal sex until I was a sophomore in college. Aside from the gay issue, I think my childhood was happy in an innocent, small-town kind of way. I love my family, and had good friends as long as I could play along with teen talk of straight sex, and did well in school. I wasn't the valedictorian but was a close second. I came out to my parents and brothers when I was a junior in college and they have supported and loved me despite my sexuality. I'm lucky that way."

"So, after high school?" I asked.

"I went to the University of Michigan and studied exercise physiology, and I don't want to brag, but I graduated with high honors and was elected to Phi Beta Kappa. It's a difficult course with lots of science, but I really enjoyed that part of it. During college, I expanded my gay experience, joining the campus LGBTQ organization, and meeting a lot of other gay boys. Some were `flaming fags' and some were like me: presenting as regular straight jocks. I continued sports in college, but only on the intramural level, where I met a group of gay athletes. I also joined some clubs: film, theater, music, that kind of thing. I was introduced to anal sex by an older boyfriend who was a senior when I was a sophomore. He liked getting fucked and he taught me to get fucked and how it wasn't gross if you were clean inside and out."

"Wasn't he scared of your huge cock?" I asked. "And, by the way, where did such a piece of equipment come from?" I said with a smile on my face.

"Well," he said, "let's take the second question first: it's genetic. My dad and my brothers all have big cocks. Maybe not quite as big as mine. I've never seen my dad erect, and it would be weird if I did. I've seen my brothers, and they're both in the eight-and-one-half to nine range, and thick like me. We've jerked off together. My middle brother is straight and my younger one I think is gay, but he is not out to anyone--me included--as far as I know.

"To the first question: my boyfriend guessed I was big from the bulge in my jeans, but he was surprised when he saw my cock hard. He wanted my cock and also to introduce me to anal sex but didn't know what to do. A few weeks went by and we discussed my size and how we would work it out. He wanted it badly though, and so what we did was to go to an ABS and buy a couple of dildos, one that was about seven inches and one that was nine inches. We spent one night playing with them and some lube and when he could do the larger dildo without pain, he let me fuck him. I tried to go slow and easy, but that's hard when you're nineteen, and I think he experienced some pain until he could get used to it. Later I learned to slow down and help him out and we both really got into it. He was a great bottom."

"And what about your fantastic body?" I asked. "Do you work out a lot, lift weights and like that."

"Well, again, it's mostly genetic. My dad and my brothers are naturally muscular and defined like me. My dad's forty-five and has the body of a 20-something. He's the envy of all the other men in his group. You can see it in their eyes when we're at the beach at the lake. I work out a few times a week as well as a little when I train people, but I don't do any serious weight lifting, body building or aerobic training like competitive athletes do."

"What about boyfriends?" I asked.

"In college I not only had several boyfriends for some months and in one case about a year, but I learned about gay bars and the baths and indulged whenever I could get to a place where there were gay baths. Some of my gay friends and I used to get in a car and go together to the Steamworks in Chicago for a weekend, staying at the home of one of the guys. I learned about a lot of the variety of gay sex on those trips.

"Right out of college, I got a job as a trainer at an upscale gym in Chicago. I really liked the work, and I got good tips, but I only got a piddling portion of the fee the gym charged my clients. I was very popular, and got propositioned by both women and men, but steered clear of mixing work and sex. My goal is to own a gym of my own, and to also train professional athletes, especially baseball and football players."

"How did you get into escorting, if it's OK to ask," I said.

"Sure it's OK. I made enough doing personal training plus the tips to have a normal life: rent a decent apartment, buy groceries, go out with friends, stuff like that. But the prospect of saving to buy a house or have a life with a guy seemed remote. I had a lot of college debt and my monthly payment made it hard to get ahead. My parents are generous, but don't have the resources to help a lot with that, and I have a brother in college and another close behind. I can't count on them.

"I got propositioned enough by older clients that I thought: What if I try to make some money at my other talent, sex? I enjoy it a lot and as long as my clients are not crazy, I doubted that it would be dangerous. I was encouraged by a friend who was exactly in my predicament, and had been escorting part time for about six months. He said there were ways he could teach me to ask potential appointments questions that would reveal whether I should be concerned or not. He was rapidly retiring his college debt, and figured that if he could escort for a couple more years, he would have a nest-egg for buying a house or starting the business he was planning.

"I had, of course, surfed the web looking at rent-boy sites, and what gay porn I could get my hands on. My friend said he was on a local escort site that I had looked at briefly, and it was working well for him. There was a modest listing fee and monthly fee. You provide them with a profile text and up to ten pictures, and they put it online. My pix don't include any face shots but I do have shots naked, torso shots, shots bare-chested in jeans or a jock, and a couple of my cock flaccid and erect. You set up a separate email address from your regular one that you list on the site. Some guys even have a separate cell phone, but I don't. My friend said that with my body and cock, that I would be really popular, and he suggested that I start with a fee like his: $150 per hour, $600 or 750 overnight. He said if you're getting more calls than you can handle, raise it accordingly. And he said that sometimes he gets calls for 3- or 4-ways and we could help each other out. Right away I got a lot of calls and a couple of weeks later raised my fees for new clients.

"Most of my calls are from middle-aged overweight guys, most of them married. Some are happily married except for an unsatisfactory sex life, others are gay guys who thought that marriage would `cure' them. I get some calls from other gay men and younger guys who are in the closet, or are busy professionals who don't have time to hang out at bars to meet men. And sometimes I get a call from professional athletes, like the two basketball players I told you about. They like that I have an athletic body, and am a professional trainer, I guess. I have a bunch of regulars, like Paul: busy successful guys who not only like the sex but enjoy the companionship. Yeah, I can hold a pretty decent conversation on a lot of topics. There are some guys for whom the sex is definitely secondary. It's those guys that I do a lot of overnights with and who I travel with occasionally.

"My work as a trainer is officially free-lance, so as long as I serve a decent number of clients, my fitness center allows me to set my own hours, so I can do appointments with my clients pretty much when I want. Most clients are women who want to train in the morning or from about 11 to 3, which tends to be slack hours for escorting. This week is no problem because the demand for training drops in the summer when a lot of my clients are away on vacation.

"In the eight months that I have been escorting, I have mostly retired my college debt, and am starting to see a road to saving for a house or condo and capital to start a business. I think `ll be happy doing it for maybe five or six more years. I enjoy it and the downside has been not too bad: a couple of sketchy appointments that I pulled out of early, and some where the clients had really bad breath or hygiene problems. I just give the money back and politely say good-bye. If they write a bad review on the site, there is a response option that I use, and generally I can just tell the truth in my response.

"So that's pretty much it. I guess I'm the proverbial whore with a heart of gold!"

I said, "Well, I don't know you long enough to say anything about a heart of gold, but I can attest to a cock of iron. I have something that I would like to tell you, but why don't we fill these glasses again," and I went to the fridge to get the chilled bottle of Sancerre we were drinking.

I topped up our glasses and said "I'm forty-five."

Jason said "No way! I woulda thought you were in your mid-thirties with your tight body and six-pack. You're like my dad, but he has more lines in his face, and he's got more gray at the temples. Most guys I've met hit thirty and then start to get a bit, well, soft, or at least thicker around the middle. The too-much-beer-and-pizza syndrome."

"Well," I said, smiling at his reaction, "to continue: I AM forty-five. When I was turning forty I had a traveling exhibition of my work, and I thought I would celebrate the milestone of the big four-oh by having sex with one thousand men in a year, no repeats allowed." I smiled at Jason.

"Geez, I have a lot of sex and I can't imagineÉ." Jason said.

"It did take some strategizing," I said. "Had to do nights at the baths with twenty or thirty encounters many times, and I had to record my encounters. Just touching and kissing did not count; only oral and anal did. Anyway, I managed to do it. And part of the strategy, though unplanned--something that happened when I was in San Francisco for a month working on my show there--at the suggestion of a guy at the gym I where worked out in the Castro, was that I signed on with a local escort agency for about a month. I had the same body as now but even tighter and my face was a bit more boyish. They listed me on their website as twenty-nine--a little white lie. The web was not as robust five years ago, but it was enough. I averaged two to three appointments a day while I was there, as well as hooking up at bars and the baths in Berkeley for my own pleasure and to keep my count up to snuff. My experience was similar to yours: lots of needy middle-aged, somewhat dumpy guys who were, by and large, really nice and considerate, a few jerks, a professional baseball player, guys in computers working eighty-hour weeks and bringing in high six-figure salaries and one memorable guy who hired me and a hot Latino escort to make love while he sat in a corner and jerked off. All-in-all it was fun, and a great experience. Us artists like to collect diverse experiences, but I didn't really need the money and a month was enough for me. I do look back on it fondly though and I hope you will remember some of your better experiences in a few years. I hope tonight will be one of them."

"Speaking of which," he said, "this needs some attention," as he stripped off his shirt and shorts and I watched as his cock lengthened, thickened and gradually stood at attention, standing up at a sharp angle from his big balls, and pointing at his chin.

I said "Lie on the bed and let me see what I can do." He laid back with his legs apart, his skin glistening in the low light of the room. I pulled off my towel and my erection sprang out, jutting in front of me. I went over to the bed, knelt between his spread legs and laid chest-to-chest with him, his hands on my buns, mine hooked under his arms and grabbing his shoulders, and we glued our mouths together in a deep kiss. After a minute, I broke off and got the pump bottle of lube and pumped some onto Jason's belly and cock, then went back to kissing him, rubbing my cock against his and his belly, him pushing up against me as he wrapped his legs around mine and pulled my buns apart to caress my hole with a finger.

"Oh yeah, I think you know what I want," I said.

"I'm a mind reader?" he said.

"HmmmmÉ." I murmured as we rolled over, him on top.

I pulled my legs up and he thrust his cock energetically against my own and my belly. We kept kissing while he pumped energetically, and I pushed back against him. I moved my hands from his strong shoulders, down his back to feel the muscles at the base contract and release as pushed his big cock against mine. I moved them farther down so that they were on his buns, also contracting and releasing as he dry-fucked me.

"Fuck, this feels so fantastic," I said, "I'm afraid that I'll cum before we get to the big event."

He propped himself up on his hands as his cock slowed down but kept up its motion against me and said, "If you cum now, are you gonna be ok with me inside you? I know that a lot of guys cum and are done."

"I'm cool with that," I replied. "Actually, I'll probably cum again. I'm mostly a top with Robin, but I love to bottom too. I've had a couple of partners who I was really a total bottom pig for."

"Wanna cum in my mouth?" he said.

"Yeah, I'm ready," I said.

He kissed and licked his way down my body, paying a lot of attention to my nipples and working over each hill and valley of my abs with his tongue, before kissing the tip of my throbbing cock and taking it slowly into his mouth, inch-by-inch until he bottomed out at my pubes. He held me there for a minute, contracting his cheeks and throat and letting go and working his tongue around.

Then he slowly started to move up and down on me, varying the pressure, working with his tongue, swirling me around in his mouth, twisting his head and lips as he descended or ascended. He was practiced and had a natural talent too. He was probably pretty great at sucking cock before becoming a professional, but he had the polish of a real pro, which he was. I encouraged him with my moans and caressing his head and hair as he worked on me. I had to stop him a couple of times: I wanted more before I climaxed.

It took about five minutes of his talented cock-sucking before I felt the inevitable. I reached for the bottle of poppers and took a big hit just before he pushed me over the edge and I exploded in his mouth just as the poppers washed over me.

"Geezus, oh my God, Jason, oh fuck, that was so good, oh babyÉ." I whispered as he took my cum down his throat and slowed his lips. He kept me in his mouth, caressing me with his tongue and sucking in and out softly. I was still really hard, and so sensitive now that it was almost painful and I asked him to stop.

He came up and kissed me softly and whispered, "Did you like that John?"

"Oh, Geezus, yes," I said. "You gotta do that again!"

"OK, later, baby," he said, "but right now I have a big cock that needs satisfying, and I know you want it, right?"

"Oh, yeah, man," I said. "I want you to take me, make love to me, own me, show me how you can make me feel real good. Please, baby, pleaseÉ."

He knelt between my legs, and pushed them back over my head. "Let's get you ready. I want you to love my big cock, John." I grabbed my ankles with both hands. He kissed down the backs of both thighs and all around my hole for a few minutes, teasing me, licking, getting closer and closer, but not quite getting there. He took a squirt of lube and gently swirled it around my anus, pushing his finger in just a little, not even past my sphincter. It felt wonderful. Then he bent forward again and kissed and licked my hole, pushing his tongue in just a little, teasing me even more.

He licked and probed with his tongue, pushing in farther each time. He had me whimpering and moaning, and every so often, he paused and leaned over to kiss me.

"Does that feel good, John?" he whispered.

"You know it does Jason," I said, "but you gotta stop teasing me. I want your cock."

"Not yet, John, I really want you ready and begging for it," he said, and went back to rimming me. I took another hit on the poppers, and the pleasure of his rimming nearly sent me over the edge again when the poppers hit. As he rimmed me he pushed in a finger and swirled it around inside me, took it out and replaced it with his tongue, then did the same thing with two fingers, worked me with his tongue again, and then went on to three fingers.

When he took them out, I felt incredibly empty, longing to be filled again. He bent over and kissed me again, and whispered, "Ready, baby?"

"Oh yeah, man."

"How bad do you want it?"

"Jason, don't tease me," I said, "please, please, give me your cock. I want you to make love to me so bad."

"Are you really ready?"

"Please, pleaseÉ." I pleaded.

"Here comes," he said, and he slipped on a condom, squirted lube on his cock an my ass as I took another hit of poppers, and then he slowly pushed all the way in, taking a full minute to do it.

The poppers hit me once again and I felt like I was born to be fucked by the biggest cock ever. I moaned a contented moan, and pulled him into a deep kiss, wrapping my legs around his waist and whispering, "Fuck me, Jason."

He pushed himself up on his arms, an started long, slow strokes, in and out, swiveling his hips in a circle, pushing in straight, and then moving his hips up and down so that his cock massaged the top of my rectum and then the bottom. He was gentle and firm and I loved watching his smooth glistening chest and abs contract and relax as he moved in and out of me.

He took my cock in his hand and started stroking it in time with his fucking and I had to push his hand away a couple of times to keep from cumming. He fucked me like this for a good ten minutes. I was in heaven: being fucked on my back with lots of kisses is my very favorite thing when I bottom.

We both hit the poppers again and I whispered to him after a deep kiss, "Speed it up, baby. I want you to fuck me deep and hard."

He not only did as I asked, but tipped me back on my shoulders and got up to standing on his legs to drill me just as the last whiff of poppers hit me.

That pushed me over the edge, only thirty minutes after he had made me cum in his mouth. The contractions of my anus as I shot my load onto my chin and mouth pushed him over too, and he slammed into me an held it, leaning over to kiss me once again as he filled the condom inside me.

When he was finished, he lowered me gently back to a lying position, his mouth still glued to mine, our tongues working together and he held me tightly as we both wound down, a sweaty mass of manhood.

Finally, our cocks both softened after a couple of hours of being so hard it was almost painful. He pulled out before the condom could fall off, slipped it off and put it on a tissue, and wiped his cock and mine with one of the hand-towels next to the bed. I took another and dried off our chests, and we kissed and cuddled.

"Man, that was fantastic," I said, "thank you so much. I've been fucked by some very large cocks, but yours was the best. It was amazing."

"John, there's been a special chemistry between us. Thank you too. You are an amazing lover."

We cuddled a while longer and fell asleep in each other's arms. During the night, I woke up to pee and realized we were both still wearing our cock-rings. I slipped mine off, and gently unsnapped Jason's and eased it off around his cock and balls as he said something in his sleep that I could not understand.

I quickly went back to sleep and slept like a baby until the morning sun showed brightly around the edge of the drapes on the window.

What transpired during the day is my next story.

Next: Chapter 7


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