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! 18
2009, Spring Break
March 2009 I was almost 51. I was itching to get out of Philly. It was snowy, it was rainy, it was cold, and everything looked gray and dirty, and I felt kinda gray and dirty too. I'm an artist, and even my paintings had begun to seem gray and dirty.
Usually, I am happy to spend the winter here: there's lots to do, lots of social life, friends, exhibits, concerts and activity. But I wanted a change. I called an old friend, a fellow artist--gay as well--who had gotten a small cottage, a so-called "Conch" house, in Key West a few years before and had been after me to come down sometime for a few days. I always had something else to do, too busy, or some other lame excuse. But this year, I decided to take him up on his offer.
When I called him he said, "Cool, John, it will be great to see you. Why don't you come down a few days before the first weekend in March, we can visit, and if you want to stay a couple or three weeks, you're welcome to. I have to go out to the west coast to teach a workshop for the rest of March so you can have the place to yourself, and if you want, you can set yourself up in my studio while I'm gone."
"Let me think about it," I said; in truth, I had already made up my mind. I called him back the next day, and made the arrangements. He said he would pick me up at the airport, and let me use his car and bike while he was away. So a few days later, I was on a plane to Key West, my bags filled with shorts, T-shirts, and art supplies.
We hung out for a couple of days, and he showed me around: his favorite restaurants and bars, the best places for middle-aged guys to cruise and get results, the beaches, and shopping. On Saturday morning I drove him to the airport and went back to set up in his studio. Since my arrival I had already done some new drawings and a couple of watercolors, responding to the light, color and warmth of the place, and it looked like my paintings were beginning to shed their gray and dirty look.
After working the day to get the studio set up, I went out for some dinner, and then headed over to a bar that we had gone to a couple of times already. In Key West, some of the best gay bars are not exclusively gay. You see women and straight men there too, because they are just great bars. That didn't faze me: I trusted that by this point in my life my gaydar could tell whether someone was gay or not.
Now, Key West has long been a gay mecca, like P-town, but in recent years, they had started promoting it as spring break destination for gay college students. Though the spring break season lasts from late February into early April, the majority of colleges have theirs sometime in March. And, indeed, I had been seeing a lot of young men around in the past few days. What middle-aged gay man doesn't like a bit of boy eye candy? I didn't kid myself that I would be getting a steady diet of young cock while I was here, but I could hope, couldn't I? In the meantime, I could certainly enjoy the view. And I was slim and in good shape, albeit with a few more lines and more gray hair than I would have liked, so I gave myself at least a fighting chance at success.
So, here I was, sitting at the bar, nursing a beer at a stool next to the break where customers could come up and order from the bartender. I had been there a few minutes, when a young man came over to get a drink. He was tall, slim, broad-shouldered, and good-looking, with a nice boyish face. He was wearing an oversize white tank top, shorts and flip-flops. While he waited for the bartender to come over, he looked around, and smiled at me. "Definitely gay," I thought to myself, and so I said "Gay spring break?"
"It's that obvious?" he said, smiling back at me.
"Well, you're college age, and you don't have a tan or sunburn yet, so it's probably a good bet," I said. "Where do you go to school?"
Before he could answer, the bartender came over, checked his ID, and he placed his order, then he answered my question with the name of my old alma mater.
"No way!" I said, "that's where I went, like, in the stone age."
"What year did you graduate?" he asked.
"You don't want to know."
The bartender came back with his beer. Before he could pay him, I pushed a five across the bar. "A little gesture from the alumni association," I said. He thanked me, and came over to the bar stool on my other side and sat down.
"Are you here with a friend?" I asked.
"Well, sorta," he said. "The GLBT center at school had some information about the Key West Gay Spring Break promotion, and so I got a group together and we got a few rooms at a gay-friendly hotel. The guy I'm rooming with is not my boyfriend or fuck-buddy, just an acquaintance. We came over here together about forty-five minutes ago, and pretty soon he was chatting up this cute guy. He asked me if he could have the room to himself for a couple of hours, and so he's probably fucking that boy right now."
"Ahhh, to do it over again," I said, somewhat wistfully. "When I was in college, they just started a GLB center. No T then. The school didn't really want to acknowledge there were gay students, and looked the other way at gay bashing, and even hetero date-rape, especially if the perpetrators were on the football or hockey team. It was not a good idea to come out publicly then, if you valued your health, and I didn't come out really publicly until I was in my 30s. You're lucky that you can be yourself these days. By the way, what are you studying in college?"
"Studio art," he replied, "mostly painting and printmaking."
"Shit, that's what my major was," I said. "I wonder if any of the same faculty are still there?" There were a couple of faculty who were young when I was there, who could still be around. I mentioned a couple of names, and sure enough, one of my painting professors back then was still at it.
"By the way, my name is Jake," he said, holding out his hand.
"John," I said, shaking it. He had a firm masculine grip and a nice smile. And, he held my hand just a little too long. "Maybe this will get interesting," I thought to myself.
"Do you live here?" he asked. Was he about to ask to come home with me? I could hope!
"No, but I'm house-sitting a few weeks for a friend who has a place here. He's an artist, and he suggested that I set up in his studio for a few weeks while he is out of town. This is my first time here."
We talked for a while. He asked about my work and I did my best to describe it, though I always find that words fail to communicate very well what I do. I asked about his work, and he pulled out his iPhone, and showed me some pictures of work he had been doing. Definitely student work, but it showed promise.
"Sorry, I'm not au courant enough to keep a portfolio on a phone," I apologized. "I need to get with the program."
"Is there somewhere I can see your work?" he asked. "Do you have a website?"
Busted again. "I'm just working on getting one together," I lied, though, in fact, I had been thinking that I needed to do that ASAP.
"Do you have any work in your studio here?" he asked.
This was too good to be true. "Well, I have a few drawings and a couple of watercolor studies I've done since I got here a few days ago, and my friend has a couple of my older paintings, and catalogues from some of my shows," I said. "That, plus I have beer and wine in the fridge, if you want to come over." There, I did it. Would he bite?
"Let's do it," he said, tipping up his bottle and draining it. Hooked! My cock was already stirring in my shorts, though I still thought that there was only a distant chance that we would end up playing together.
We walked the few blocks to the house--nothing's very far in KW--and I showed him into the living room. "Want a beer, or a glass of white wine?" I asked.
"Yeah, man, a glass of wine would be great," he answered, his eyes scanning the room. He looked awed, or at least fascinated. My friend had made the house into a comfortable, visually rich place: lots of paintings and drawings crowding the walls, some interesting local antiques and primitive pieces, fascinating objects--both natural and man-made-- crowded the tables and shelves, and there was a big library of art and nature books covering one end of the room from floor to ceiling.
I came back with two glasses of wine, and he turned and said, "This is the fucking coolest place I've ever seen!" I remembered the first times that I visited older artists and envied the kind of lives they had: rich with things to look at, to touch, to read. I guess I had gotten used to that kind of environment since so many of my friends lived that way. "Shit, man, this is the way I want to live. I'm so fuckin' envious!" he went on. "Are some of these pieces of art yours?"
I showed him a couple of smaller paintings that I had given my friend a few years before, and then took him into the bedroom where one of my larger works was on the wall. "Fuck, man, these are great," he said, me blushing. It seemed awful easy to impress him, but then I thought back to the day when any moderately accomplished work seemed like magic. "Can I see what you've been working on here?" he asked.
"Sure, no problem, but they are just some small drawings and watercolor sketches, while I'm exploring the local subject matter," I said. "No big deal, but I hope to get some good things going while I'm here."
We went out through the small garden to the outbuilding that contained the studio. I had turned my friend's work to the wall, and pinned up my new works of the past few days on a clear wall at the side of the studio. "Man, you make it look so easy," he said. "Like, drawing is such a struggle for me. I can never get it the way I see it in my head."
"Well, it may surprise you," I said, "but neither can I. It's always a challenge, and I never seem to get where I want to go." For the next half hour or so, we discussed how we worked. He probed me with questions that I thought were really insightful; he wanted to know about my process, not just how I thought about things, but how I actually did them, like the kind of paper or paint I used. His excitement was infectious, and I began to remember how it was back when I was 21 and all the excitement of a creative life stretched ahead.
Our glasses of wine were empty. "Let's go in and get a refill. We can get a little more comfortable in the living room and talk there," I said. So I let him lead the way back to the house, giving me a nice view of his broad shoulders, slim ass, and supple calves, my cock swelling once again, and I refilled our glasses. We sat next to each other on the sofa, and now, after a couple of drinks, we were easy and relaxed together.
I changed the subject away from art, and asked him about what being gay at college was like now. He said, "I grew up in a pretty sophisticated city, and came out when I was 16. My parents were cool about it, and, though I got a little flak from the jocks in high school, I had a group of friends, both straight and gay, who were, like, totally cool with it, like it was no big deal. And it's pretty much the same at college. I like the GLBT center, cuz there are a bunch of cool kids there, both guys and women, but nobody makes much of a deal about it. You like someone, and he likes you, and you just ask if he wants to play, and it's no problem if he says yes or no. So when you said it was much different back then, what was it like? Nowadays you can have a boyfriend, and nobody blinks."
"Well," I said, "it was not open back in the day. I knew I was gay in high school, but I had no clue how to find like-minded guys. I was afraid I would embarrass myself, or worse, get beat up if I approached someone. It was like that in college too. It was a complete mystery to me how to get together with a guy. I mean, I didn't even have a real clear notion of what guys did together, sexually, I mean. I guess I was pretty na•ve, but I later learned that a lot of gay boys I met at the new GLB center had been in the same boat.
"When I was a junior, I was twenty, I was still a virgin, and a very horny one at that, and I saw this note posted on a message bulletin board in the student union. It was in April, a few weeks from the end of the term. It was long before the days of the internet, email and cell phones, so it was a lot harder to communicate with guys who might be interested in the same thing. The message said ` Young? Hot? Ready? Male? I can teach you what you want to know. Call after 5,' and it had a phone number.
"I was not really sure if it meant what I thought it meant, and all afternoon I was so nervous and excited, I cut class and I think that I jerked off four times fantasizing about what might happen. When five came, I picked up the phone, and dialed, but put it down before it rang. I did that four more times before I finally said to myself `this guy doesn't know who you are, and you can always hang up,' so finally I let it ring, and after the third ring it was answered by a friendly, masculine voice.
"I told him that I had seen his message, and it sounded interesting, and could he explain it more. He said sure, and then told me that he was a guy who liked other guys, and how hard it had been when he was younger to find someone the same, and how he thought he could help out newbies, as it were, by teaching them some of the ropes. He described himself for me. He was a grad student, four years older than me, said he was 6' tall, 160 lbs, pretty athletic, with what he called aswimmer's' build. He also said he was patient and gentle, and he wouldn't take me anywhere I was uncomfortable. He asked me to describe myself, and then he said `You want to come over tonight?'
"His directness shocked me, and it was so sudden that I was really caught off guard and hesitated a while before I said Yes.' Great,' he said, `how about 7:30?' and gave me his address.
"At 7:30 I was in front of his building, and almost lost my nerve again, but I said to myself, `At least I can see what he looks like. I don't have to go in if I'm not comfortable,' so, hesitantly I went up the stairs to his apartment and knocked on the door. A few seconds later he opened it and I was looking at a stunningly handsome young man: curly black hair, a big smile, dark eyes, standing in gym shorts and a T-shirt. I could see from his arms and the way the T-shirt fit, that he had a hot, athletic body.
"He invited me in, and we sat down together on the sofa, and he offered me a Coke and did his best to make me feel comfortable, though I was kinda shaking with nervousness. His voice was very calm and kind, and pretty soon, I was not so worried and nervous anymore. He asked if I had ever been with a boy before, and when I said No, he said we could take it easy and just go as slow as I wanted.
"He started whispering how good he thought I looked, how much I was turning him on, how he would like to kiss me, and so forth and put his hand on my leg and gently caressed me. I already had a raging hard-on, and I didn't know what to do, so I just let him take the lead. Pretty soon we had our shirts off, and were feeling each other's bodies. He had an incredibly defined, muscled body, like I sometimes fantasized about, and he told me how much my slim physique turned him one. We went into the bedroom and stripped, and it was the first time I had seen another guy's erection. We lay down together, and feeling another man against me was just about the best thing that had ever happened to me.
"He did take it slow, but it was not long before his hand had stroked me to a climax, and then I did the same for him. We lay there for a while and started again, and this time he put me in his mouth, and that was the most incredible sensation that I had ever had. We played until about 11, and I had climaxed three times, I think, and he suggested that we go out to a club where we could dance, and the other customers were all gay men, and so I had my first introduction to a gay bar.
"After the club, about 1:30 in the morning, we went back to his apartment and made love some more, and then again in the morning, though I was still not up for sucking him yet. He didn't mind though; everything in due course, he said.
"Well, after that, we spent a lot of nights together, and he taught me about sucking, and nipples, and he taught me to fuck him, and he rimmed me, though getting fucked or doing rimming was still something that I had to get used to the idea of. In June after school was out, and I was working for the summer and he was working on his research, he invited me to a pool party at the home of a gay couple in their 30s or 40s. I had never had sex with anyone but him until now, and the prospect of crossing that line into group sex or older men was both scary and really exciting. Again, he was encouraging, and told me he would look out for me, and assured me that everyone was there for the same kind of fun, and it was safe.
"So we went, and I really let go that night, having sex with at least five other men, both my age and older. I learned to like sex with older guys then, because their experience often made them really good partners. And I had sex with a guy my age who was incredibly hung. I thought he might want to fuck me, and I was worried because I hadn't bottomed yet, but it was the other way around.
"So after some great tutoring from my friend, I started getting to know how to read the signs if a guy was interested in me, and I started meeting other guys at school. Sometimes I went to the baths in Chicago, or got into other things, though I never took to domination or water sports and stuff like that. The summer after my senior year, I took a trip with a gay friend and spent some memorable days at some of the gay beach resorts, like P-town, and Fire Island. No going back for me after that."
Jake had listened with rapt attention, and when I looked down at his shorts, I could see that he was pretty excited by what I had told him. I had to admit that thinking back on those years had made me pretty horny too.
"You know, John," he said, "when you were talking about being young and getting it on with older guys, like, I think that is really exciting. I mean, I spent an evening with a guy in his 40s last year, and it was really not."
"You're saying youÉ.?" I started.