His name was Roland and he was from Jamaica. I’m guessing he was about 30. He had deep ochre skin, eyes that were almost black, closely-cropped hair, and was tall, lean and very graceful. At one point in his life he’d been a dancer, but was now a set designer for one of the larger theater companies in Amsterdam. He was just a little bit effeminate, and overtly gay.
I’d come to Europe for the summer between my sophomore and junior years of college. I’d gotten to Amsterdam in week two of my grand tour and got stuck there—stuck because I was having too much fun. Somehow I landed in a small hotel in the high-class Red Light District.
The owner of the hotel was a crazy Dutch guy named Jan who rented cheap rooms and sold high quality hashish for absurdly low prices. I’d been there for a week when Jan offered me free room and board for a couple of weeks in exchange for helping paint the various bedrooms in the hotel—plus all I could smoke. I cancelled the next few weeks of my grand tour and got right to work.
I spent the next few days painting and my nights were a blur of drinking fresh Heineken, getting high, dancing, and partying with Jan and his friends. That’s how I met Roland. He was one of Jan’s best friends and hung out with us often.
I was nearing the end of my painting job in the hotel when Roland asked me to help him with a project.
“Jan says you’re very good with a paint brush, mon,” he said in that melodic islands accent of his. “Would you be willing to work for us on a set for a few nights? We’re horribly behind and I need a good painter.”
“Sure,” I said. I’d been worrying that I needed to leave soon and had begun thinking about where else in Europe I should be visiting. Working with Roland would give me a good excuse to stay for a few more days at least. Plus, I’d done a little set work in my high school theater and enjoyed it.
“Brilliant,” he said. “I’ll come get you after dinner.”
I spent four or five hours each of the next four nights working hard with his set crew to get everything ready for the dress rehearsal. The play was some sort of experimental drama that required lots and lots of blue paint in various shades and textures. I tried to follow the plot during the rehearsals but gave up after two nights.
Finally, on Saturday night around midnight we were done.
“Party time children,” Roland called out to the set crew, clapping his hands. “Meet me at the Sing Singel,” he continued, naming a local pub. “The drinks are on me.”
Turning to me he said, “Come with me, Tommy. You can’t go out dressed like that.”
I was in my usual uniform of torn jeans and a t-shirt, and was covered in blue paint, so I had to agree.
Roland’s apartment was only a few blocks from the theater. It was a large, open loft, painted something close to peach and had lots of bizarre art hung all around. The furniture seemed scattered in an entirely random fashion and books were piled up on almost every flat surface. For some reason I’d thought gay men were all neat freaks and good decorators. Roland was obviously an exception.
I stared at the room and tried to get my bearings amid the chaos. When my gaze finally got back to Roland, he was staring at me with a happy smile on his face.
“First things first,” he said, taking some hash from a drawer in the kitchen area, positioning a chunk on a pin stuck through a playing card, and lighting it. He placed a wine glass over the smoking hash and when the glass was full of smoke, I took it from him, tilted the glass and inhaled. The two of us passed the card back and forth until the hash was all gone and we were both very high.
“Shower’s over there,” he said, pointing across the room, his eyes now black circles floating in a sea of bloodshot. “Clean up and I’ll find you something to wear.”
Showering quickly, I wondered what he’d pick out for me to wear—he was a flamboyant dresser after all. Whatever he picked would be something I would never choose for myself. All clean, I toweled off, wrapped the towel around my waist and stepped back into the main room. Roland had changed into party clothes—apparently he felt no need to shower—a pale green shirt over some loose fitting black linen pants.
He handed me a pair of deep brown leather pants. I’d seen him wearing them several times and had seen a couple of Jan’s friends in leather too, so it wasn’t too much of a surprise when he pushed them toward me. He was no more than an inch taller than me and only a little lighter, so I figured there was a good chance they’d fit.
I reached for my boxers, but he cackled, “Honey, you can’t wear shorts under those. No way!”
“Okay,” I said, dropping my towel and stepping into the pants. I was suddenly conscious of the fact that I was naked in front of a very gay man. This made me just a bit nervous, to say the least, and I glanced up at him. Sure enough, he was staring at my crotch.
I’ve always been proud of my cock because it is larger than most I’ve seen around the locker rooms I’ve been in. Getting high always made me just a bit hard anyway, so my cock was looking just a bit larger than normal. I felt a sense of perverse satisfaction that I was putting on a good show for Roland. I knew that as a gay man he had to appreciate the size of my cock. I also found it surprisingly erotic to realize that he was ogling me, and that made me swell just a bit more.
Putting on leather pants, especially when you’ve just stepped out of the shower, was much more difficult than I had expected it to be! I squirmed. I pulled. I tugged. I danced around the room. The more I struggled, the more Roland giggled. By the time I finally got them all the way up, he was on his side on the sofa, laughing uproariously.
“That was worth the price of admission,” he gasped.
Once I snapped the pants, my cock was uncomfortably squeezed down my thigh, so I reached down, pulled it up along my pelvis, and then zipped the zipper, being careful not to grab anything important in the teeth.
“Very nice,” Roland said, staring openly at the bulge in my pants. This caused me to twitch just a bit more. Maybe it was because I was high, or because Roland seemed so at ease with his sexual orientation, but for whatever reason, I felt very comfortable at that moment and more than a little turned on.
He handed me a Western style denim shirt, “because you are so American,” and some flip flops that were a full size too big, clapped his hands and shouted, “We’re ready!”
At the bar the eight of us who had worked on the set drank, danced, smoked more hash mixed up in cigarettes, and drank some more. By 3:00 a.m., I was done, and said so.
“You are much too wasted to get home on your own,” Roland said to me. “Come crash on my sofa.”
I was too tired to argue and too buzzed to want to say no, so off we stumbled to his place. Amsterdam is one of those cities that is still as vibrant at 3:00 a.m. on a Sunday morning as it is at 10:00 p.m. on a Friday night. As we staggered along, I absorbed the sights, conscious of the fact that I’d be leaving in a day or two.
When we got up to the loft, Roland went to get blankets and a pillow for me and I started trying to get out of those damned leather pants. Either because I’d worked up a sweat on the dance floor, or because I was so buzzed, or both, I could not get them off!
By the time Roland returned from the closet, I’d only managed to get my ass and crotch out, but my thighs and the rest of my legs were firmly stuck. This left me standing there, my cock hanging out of the pants, brown leather bunched up under my ass cheeks, and a forlorn look on my face.
“What a sight you are, cowboy,” Roland laughed, causing us both to dissolve into a fit of giggles.
When we’d regained our composure enough to talk, he said, “Let me,” pushed me down on the sofa, and began tugging from my feet, almost falling down when they finally came off. This left me naked from the waist down in a gay man’s apartment, him staring openly at my crotch again.
“Tommy?” he said.
“Yes,” I said, both replying to his words and agreeing with his unspoken question.
“You are beautiful.”
“Uh, thanks,” I stammered. I felt a surge of emotion then—both a desire to flee and just plain desire. Although I’d had several girlfriends and thought of myself as sexually experienced, I had no experience with gay men, and had never thought about gay sex. I knew men fucked each other, of course, but I’d never really thought about it much. Yet here I was, feeling turned on, and being betrayed by my cock, which was starting to stand up all by itself.
“I want you,” he said. “Just the way you are.”
“Uh, Roland,” I protested weakly. “Wait. I’m not…uh…”
“I know you’re not gay, sweet boy,” he said, moving closer to me, staring into my eyes now. “I just want that big, beautiful cock of yours. That’s all. I promise you. I just want to suck your cock. I won’t ask for anything else.”
As he spoke, he was moving closer and closer, his voice getting softer, and my cock getting harder. One last time, my brain yelled “Run!” at me, but my cock ignored it. Instead of running, I spread my legs to show him I was willing.
Roland dropped quickly to his knees, running his large hands up my thighs. His touch sent shivers up and down my spine and made my cock jump up off my stomach. Roland sighed at that and slid both of his hands to the base of my cock, using one hand to point me straight up in the air and the other to stretch the skin on my cock impossibly tight.
This made me moan. I loved having my cock stretched like that, feeling the blood surging up from the base to the head, the veins dilating, the head flaring as the shaft is pulled toward my pelvis.
For a minute or two, Roland did nothing but hold me like that, his hands pulsing tighter, then looser, then tighter again, finally making me beg him, “Please,” I moaned.
He smiled at me then, and lowered his face toward the head of my cock. I could feel the heat of his breath on my cock as it bathed the head, and then the tip of his tongue found the rim, circling, circling, teasing those nerve endings that are connected directly to my spinal cord, to my brain. Oh God it felt so good.
I was about to beg him again—this time to stop licking and start sucking—when his mouth began to slide down the shaft of my cock, his lips tight around me, his tongue working back and forth across first the head and then the shaft as he took more and more of me into his mouth.
When he’d reached the mid point of my cock, he stopped and sucked so hard that I thought he would make the head of my cock explode from the pressure. Then just as suddenly, he released the pressure and pulled his face away.
“Tommy,” he moaned. “Your cock is so beautiful. So big. So hard.”
“I’m glad you like it,” I rasped.
“I love it,” he said.
And then he lowered himself onto my cock again, his tongue dancing, sending waves of pleasure throughout my body. I cried out this time, the feeling was so intense. Several of my girlfriends had given me blowjobs over the years, but none of them knew how to suck a cock the way Roland did.
To my amazement, he didn’t stop this time, sliding further and further down my shaft until his nose was buried in my pubic hair. I couldn’t believe it. The head of my cock was somewhere in his throat. He started to swallow then, the roof of his mouth and the back of his throat massaging me in ways I’d never felt before. The feeling was so intense, I realized I was going to cum and cum soon.
Roland must have known this too, because he began to fondle my balls with one hand, while he stretched my cock out with the other. And he never stopped that swallowing motion.
Having my balls played with when I’m near orgasm sends me right over the edge every time. My thigh muscles began to clench, my toes began curling, and involuntarily, I reached out and grabbed his head where it rested, chin on my pelvis.
“Shit!” I screamed as my orgasm hit, a surge so powerful that I felt as though I was being turned inside out. Roland moaned as my semen filled his throat, but just kept up his swallowing motion, milking me completely dry. I don’t know how many pulses of semen I sent into his throat, but I had never cum like that in my life.
And then my cock was too sensitive to bear what he was doing to it.
“Stop,” I begged him. “It’s too much. Can’t stand it.”
Obediently, he drew his head slowly off of me, letting my cock slide from his mouth, bathing it one last time with his tongue. And then he lay his head on my heaving stomach, still holding me with one hand, my cock twitching with the aftershocks of my orgasm. I reached down and stroked his hair as he lay there, too spent to speak.
After a few minutes he stood and began to disrobe. The green shirt came off first, exposing his lean dancer’s frame, and then he dropped his baggy pants to the floor, leaving me face to face with his cock. It was almost as large as mine and was very hard. Where my cock is both long and thick, Roland’s was long and thin and it was even darker than the rest of his skin.
“I promised you I wouldn’t ask for more and I won’t,” he said. “Just lie there and let me cum on you.”
I smiled at him and nodded, mesmerized by the sight of his large cock so close to my face. I felt guilty that he’d just given me such an incredible blowjob and all I was going to do was lie back and let him spray on me. I knew that if I opened my mouth, he would slip his cock in and half of me wanted that very, very much. The other half, the confirmed straight half absolutely did not.
Roland smiled down at me, spit on his hands, and began to stroke that impossibly thin cock. I realized with a start that he was completely shaved, something I’d never seen before. The smoothness of his skin at the base of his cock and his hairless balls were beautiful. And as he stroked himself, he began to talk.
“You’ve never had a blowjob like that before, have you Tommy?”
I shook my head.
“Now you know that a man knows how to suck cock much better than any woman ever will. No girl has ever taken that big meat of yours down her throat, has she?”
I shook my head again.
“I knew it. Your cock is so big, so beautiful. Those girls of yours, they want to suck it all in, but they’re afraid. Not me, I want that big cock of yours all the way down my throat. You liked that didn’t you?”
I nodded. His cock had grown as he stroked it, the head swelling now, appearing and disappearing from his fist.
“You like the look of my cock too, don’t you Tommy?”
I nodded. “It’s beautiful,” I said.
“I knew you’d like it. I love to stroke it like this. I bet you beat yourself all the time, a handsome young boy like you. You love to beat off, don’t you Tommy?”
“I do,” I groaned.
“Do you beat it hard like this?” he asked, suddenly pistoning his fist up and down. “Or do you beat it soft and slow like this?” he asked, slowing and sliding his hand along his shaft with almost excruciating slowness.
“Hard,” I said. “I like it hard.”
“I knew it,” he said. “A big cock like that, it needs to be beaten hard.”
“Yes,” I said. “Sometimes I get really rough with it.”
“I know you do, you sweet thing. You’ve got secrets, don’t you? Secret ways you play with yourself, secret ways you make yourself cum.”
I nodded. His cock was so beautiful, so amazing. As his hand would reach the base, the eye in the head would flare open, winking at me, hypnotizing me the way a snake hypnotizes a mouse. I couldn’t look away. I didn’t want to.
“Tell me your secrets Tommy. Tell Roland how you make yourself feel good.” His voice was part soft whisper, part command.
“Sometimes, when I’m watching a porn movie, I beat my cock so hard. I squeeze it as tight as I can and yank it.”
“Yes, you do, don’t you? It feels so good to beat your cock hard. Like this,” he said and began stroking himself furiously, his hand a blur as it ran up and down his shaft, the head of his cock disappearing and reappearing from his fist.
“Like that, yeah,” I moaned. “Just like that.”
“What other secrets do you have Tommy?”
I gulped. It was as if Roland was looking into my heart. But I had to keep talking.
“I like to stick a finger in my ass just before I cum.”
“Feels so good doesn’t it? That finger probing up there like that, like a little cock?”
“Yes,” I admitted. “And sometimes I like to tie a bandana around my balls so I can’t cum and I just beat it and beat it and beat it.”
“Oh, God,” he groaned suddenly, and as he did semen came flying from the head of his cock, splattering on my chest, my stomach, and then on my cock. His hand just kept milking and milking that big, beautiful cock of his, sending glob after glob onto me.
Looking down at the mess he was making on me, I saw that my cock had become very hard again. I’d been so mesmerized by Roland’s jack off show and by the talk of my own masturbation that I hadn’t even noticed how hard I’d become.
“Oh my,” Roland gasped, like me aware now of my hardness. “Look at that. You’re ready for more aren’t you?”
I was sure he meant another blowjob, so I nodded eagerly. I desperately wanted my cock in the back of his throat again, to feel that swallowing.
Roland had other plans.
Turning to an end table behind my head, he opened a drawer and withdrew a tube of KY and a condom.
“You know what these are for, don’t you?” he asked.
I nodded again.
“I know I said I wouldn’t ask you for anything else. But I need that cock of yours in my ass. Just this once. You aren’t gay sweet boy. But this is your chance to fuck a man, your chance to find out what it feels like.”
I didn’t even think of protesting. I wanted him in the worst kind of way. To show him that I did, I reached up and grabbed his semen slick penis and began stroke it.
Smiling, Roland tore open the condom package, bent down and began to unroll it onto my cock. His touch was electric and it was all I could do not to jump from the sofa where I lay and attack him.
His dressing of my cock done, Roland turned away from me, grabbed several large pillows from various pieces of furniture and positioned them on the floor next to the sofa and dropped to his hands and knees, his head on one of the pillows. I heard the KY tube make a splorting sound and then his hand snaked up between his legs and I watched as he smeared the lubricant on his asshole.
“I’m ready lover,” he whispered.
Climbing from the sofa, I knelt behind him, my hands dropping to his hips. I’d never had anal sex with anyone before, I wasn’t sure how to proceed, but Roland was going to have no fumbling. He reached back, grabbed my cock and aimed it at his hole.
“I’m no virgin, baby. Put that big thing in me and fuck me hard.”
Gasping for breath now, I pressed the head of my cock at his pink asshole and pushed. He pushed back and before I knew it, I was in and sliding down to the hilt. The feeling of my cock in his ass was indescribable. It was as if our bodies had merged and I my cock had become part of him. He was doing something with his ass that squeezed and released the shaft of my cock as it slid in and out of him, something that no woman had ever been able to do with her cunt. I never wanted that feeling to stop.
“God yes, that fat cock feels so good!” he cried. “Fuck my sweet ass cowboy. Fill me up with your meat.”
Grabbing his hips, I began to stroke into him, using long, slow strokes that sent shivers to every nerve in my body. His asshole was clenching and unclenching on my cock in ways no pussy had ever done. Watching my cock disappear and reappear from his ass was maybe the sexiest thing I’d ever seen.
“Fuck me harder,” he moaned. “Fuck me hard, just like you like to beat your cock. Ram it into me.”
His goading sent me into a frenzy and I began to pound my cock into his ass. The sound of my thighs slapping against his, the squishy noises my cock was making, just added to my excitement.
“Oh yes, that’s right. Fuck me just like that,” he cried. “Oh yes, oh yes.”
Before long, I was close again, but I didn’t want to cum alone this time.
“Give me the KY,” I gasped between strokes. “Now.”
One of Roland’s hands rose up with the tube. I snatched it from him, drove my cock deep into his ass and then paused while I squirted a big glob into my palm.
“Don’t stop! Oh God, don’t stop,” he begged.
I complied right away, resuming my pounding of his ass, but I lay across his back now, dropping my gooey hand to his meat. Grabbing the first cock I’d ever felt other than my own, I smeared the KY onto him and then began to yank and stroke him just as hard as I’d seen him do to himself earlier.
Finding the rhythm of the fucking and the stroking took a minute or two, but once I had it down, we were both in heaven. Each of us was grunting and moaning in his own private language and before long I was on the verge of another explosion.
“I’m close,” I groaned.
“Then cum,” he ordered. “I’ve been waiting for you. Fill my ass. Fill me now!”
Holding onto his cock for dear life, I pounded into him as hard as I possibly could. No more than a minute later, my orgasm was wrenched from me and I yelled something unintelligible. As I did, I felt his cock jerk in my hand and his own semen began pouring out of him. Forgetting my own pleasure, I jerked wildly on his cock, trying to drive him to the same heights I’d just visited and he began to thrash under me, his body shaking and jerking convulsively.
And then it was over. Both of us were completely and utterly spent. Roland collapsed under me onto the pillows he’d thrown down earlier and I fell down beside him, my cock slipping out of him with a gentle pop.
“Roland,” I gasped.
“Shhhh,” he hissed. “Just lie there cowboy. No talking.”
Too happy to argue, I complied and without meaning to, I fell asleep.