At first, I thought he was just being friendly.
It was the Saturday after Christmas in 1975. I was flying back to Austin, Texas after spending Christmas with my parents in Cheyenne, Wyoming. In Denver, I changed from the 20-passenger shuttle from Cheyenne to a 727. It was night and the dimly-lighted plane was half empty. I took a book out of my suitcase, settled into my window seat and gazed out into the darkness.
One of the last passengers to board was a handsome, well-dressed man in his early thirties. He walked past my row, looking at me carefully as he went by. An instant later, he returned and settled into the seat beside me. I thought that was unusual, since the aisle seat and all three seats on the other side of our row were vacant. "How are you doing tonight?" he asked, smiling.
I'd already turned on the overhead light and opened my book. "Just fine," I answered. I smiled briefly at him, then turned my attention back to the book. I'm sort of shy anyway and that night I was depressed and not really in the mood for conversation.
My uncommunicative nature didn't deter him. Soon we were talking as if we were old friends. His name was Bill and he was a traveling representative for a big financial services company. He sold mutual funds and other investment "instruments," as he called them. I told him I'd been working at my first "real" job, a systems programmer for a computer company, for five months.
Half an hour before we were due to land in Austin, Bill casually put his knee against mine. I moved away without really thinking about it. A couple minutes later, he moved so our knees were touching again. I reflexively started to move away, then stopped myself. "Is this a pass?" I wondered.
Jeff, a boy a few months younger than me, taught me how to fuck when I was 12. My relationship with him and several other boys continued until I was 15. We fucked each other's butts, but never sucked cock or even kissed. Then I turned my attention to girls, although I didn't succeed in having intercourse until I was 21. In my last year of college, I had sex with three girls and one boy. Now I was 24 and, with a few unsatisfactory exceptions, hadn't had sex in almost a year. My new job was so demanding, I hadn't had a date since I arrived in Texas. Naturally, I was horny as hell.
I smiled and pressed my knee against Bill's. He responded by increasing the pressure.
We continued making small talk. A little later, Bill casually placed his hand on my thigh. I glanced down when he made contact, but I didn't move.
"Do you have any plans for tonight?" Bill asked as the plane swung onto its final approach.
"Nothing special," I answered. "I was just going to go home and relax."
I was trying to work up the nerve to invite Bill to come home with me when he asked, "Do you have a car?"
"Yeah, but it's at my apartment," I replied. "It was cheaper to take cabs than to pay the airport parking fees."
"I'm going to rent a car," Bill said. "Would you like me to give you a ride?"
"Sure, that would be great," I answered. "I can buy you a drink . . . or something."
When we were in the car driving to my place, Bill was more direct. "I need to know something for sure. Are you gay?" he asked.
"I like sleeping with women," I answered, "but I really like having sex with guys, too. I guess that makes me bi."
"That's good enough," Bill said. "Would you like to do something with me?"
"Sure," I said. My cock was stiffening at the thought.
"Good. Touch me," Bill commanded. I put my hand on his thigh and he immediately moved it to his groin. I could feel his cock straining against the fabric of his slacks. As he reached for me, I opened my legs to make my crotch more accessible. We fondled each other as we drove on through the night.
At my apartment, Bill started kissing me as soon as I'd closed the door and dropped my suitcase. I opened my mouth as soon as his lips touched mine and our tongues lashed each other. Bill gripped my buttocks and pulled my body against his. Our crotches were pressed together and I could feel his cock throbbing through the fabric of our trousers.
We kissed for a long time, still standing in the hall. Finally, Bill pulled free and sank to his knees. "I'm going to suck your dick," he announced as he unzipped my blue jeans. "No underwear. Good!" he exclaimed as reached into my pants through the open fly and extracted my cock and balls. My member instantly snapped to full erection. "You're even bigger than I thought," Bill remarked as he took me in his mouth.
I leaned back against the wall, almost overcome by the sensations of pleasure Bill's mouth was generating. He caressed, licked and sucked my cock and balls, rapidly lifting me toward orgasm. Almost involuntarily, I started moving my pelvis. Bill gasped with excitement as I fucked his face, slowly at first but rapidly increasing my speed.
"Oh God!" I gasped. "I'm going to . . ." Waves of cum exploded from my swollen pecker, flooding Bill's mouth. He gulped frantically, trying to swallow all my hot juice. When I was spent, a wave of dizziness swept over me and I gripped Bill's shoulders to keep from falling. That passed in a few seconds. Bill was gazing up at me. My cock was still in his mouth and a thin line of cum was dripping down his chin. I pulled him to his feet, licked the juice off his chin and kissed him. The taste of my own semen was almost overpowering.
"Let's go into the bedroom," I said. "I want to do you now." A minute later, we were undressed and Bill was lying on the bed with me kneeling between his spread legs. Pre-cum started leaking from his dick-head as soon as I began sucking him. I love the taste and feel of a man's cock. Within seconds, I was hard again.
"That feels great," Bill said a few minutes later, "but I'd really like you to fuck me. Would that be OK?"
"Sure," I answered. "Just a second." I jumped up and got a jar of Vaseline and an old towel from the bathroom.
Conditioned by my times having sex with women, I started kissing Bill and sucking his nipples. "I'm ready," he said impatiently. "Fuck me now. Hard!"
Bill was already on his back. He folded his legs against his chest and gripped his knees, exposing his asshole. I smeared some Vaseline on my stiff pole, placed my cock head against his open hole and slid smoothly into his body. Bill's anal muscles offered just enough resistance to make my initial penetration incredibly exciting. He gradually tightened his muscles as I took several slow strokes. "You've got your wonderful big stiff cock stuffed up my butt," Bill gasped. "Now jam it into me really hard and fast."
I started fucking him ferociously, driving my pole into his butt using all my strength. At first, I was afraid I'd spurt after a few strokes, but my orgasm a few minutes earlier gave me plenty of control.
"My asshole's better than a cunt, isn't it?" Bill demanded, after I'd plowed him for a long time.
"You're the best fuck I've ever had," I gasped without even stopping to think. It was true. It's always true. It took me years to realize what a shameless slut I am. My favorite hole is always the one I'm currently in.
Bill gasped and moaned and jacked off as I continued ramming his butt hole, but he didn't come. The tension in my balls gradually built until I couldn't hold back any longer. I screamed as I filled his asshole with hot jism, then collapsed on top of him, gasping for breath.
"I haven't been fucked that good in a long time," Bill announced. "Can I fuck you now?"
Bill's cock was a lot bigger than the boy dicks that had fucked me years before. It was slightly shorter but thicker than mine. The thought of having a prick that size shoved up my ass was terrifying, but also incredibly exciting. "OK," I answered after a long pause, "but take it easy."
I got onto my belly with my legs spread. Bill greased a finger and gently teased my asshole open. After a little while, I was relaxed enough to accept a second finger. The probing fingers finally withdrew. I involuntarily tensed up as something big and round pressed against the entrance to my "virgin" hole. The pressure increased smoothly. My hole's gradual opening was accompanied by sudden blinding pain. I screamed and tried so squirm away.
Bill withdrew instantly. "Are you OK?" he whispered.
"I'm too tense," I answered, almost sobbing with frustration. "I want it really bad but you're too big for me. I haven't been fucked since I was 15 and I can't relax."
"If you want to stop now, I'll understand," Bill said. I shook my head. "You could get on top of me and gradually lower yourself onto my cock. That way, you'd be in control."
"Yeah, let's try that," I answered.
Bill got on his back, greased both our dicks and masturbated us to full erections. I straddled his hips, positioned my asshole against his cock-head and slowly lowered myself, stopping when the pain grew too intense. "If you jack off, it helps you ignore the pain," Bill advised. My dick had gone limp. By the time I'd stroked it back to full stiffness, the agony from my stretched asshole had faded.
I continued beating off as I gradually lowered myself onto Bill's pole, occasionally pausing to allow the pain to pass. When Bill was halfway inside, my ass muscles suddenly relaxed and I gasped in surprise and pleasure as his remaining length slid smoothly and painlessly into my butt.
After that, I felt a little discomfort the first few times I raised and lowered myself on Bill's cock, but that quickly passed and was replaced with the intense pleasure I'd felt years before with Jeff. Soon, I was bouncing up and down as quickly as I could manage. When Bill's dick suddenly slipped out of my butt, I reinserted it without any pain.
"Let me get on top," Bill commanded several minutes later.
I slowly lifted myself, feeling a sudden emptiness when Bill's swollen pecker slipped out of my ass. "Get on your hands and knees," Bill whispered hoarsely. A few seconds later, I was in position with Bill was kneeling behind me, gripping my waist. With one swift smooth motion he slid the entire length of his stiff prick into my asshole. I didn't feel any pain, just incredibly increased excitement.
"Do you like my cock inside you?" Bill asked in a low growl.
"Oh God yeah," I answered breathlessly. "It's the best thing I've ever felt."
"Are you ready for me to fuck you good and hard?" Bill continued. "I want to ram this cock up your butt as hard and fast as I can."
"Oh yeah man," I replied.
"Are you sure you want it?" Bill teased. "Tell me how badly you want it."
"I really need you to fuck me good and hard," I pleaded. "Please take you big stiff cock and pound my asshole with it."
"Well, if you really think I should . . ." Bill's voice trailed off seductively as he slowly withdrew his tool until the head was barely kissing my puckered hole.
"Quit playing and fuck the hell out of me," I snapped.
"OK," Bill whispered. He slammed forward so suddenly and violently that I was almost knocked onto my face. His stiff rod hit my prostate like a jackhammer. It hurt like I'd been suddenly split in half, yet I would have had an orgasm if I hadn't come so recently.
Bill pounded my butt for several minutes. I had an orgasm each time his pecker hit my prostate, even though I didn't actually ejaculate. Bill began accompanying each hammer thrust with a deep bass groan. I began moaning in time with him. We sounded like bears mating.
Bill slammed his cock into me harder than he'd ever done before and stopped moving. I could feel his swollen tool throbbing inside me. An instant later, I felt hot fluid splashing against my anal walls. Bill rammed me spasmodically. With each thrust, I felt another wave of cum spray into my butt. I hadn't touched my own cock, but I suddenly started shooting in time with Bill. When we were both spent, I sank to the semen-slick sheets. Bill collapsed on top of me. I fell asleep almost instantly, still feeling his cock in my ass.
It was near dawn when I woke up with a hard-on. We'd shifted around so Bill was facing away from me and my stiff prick was pressed between his buttocks. I slid into him easily. Bill gasped in surprise and rolled over onto his belly. I stayed on top of him. He screamed in pleasure as I fucked him until I shot my load inside his ass.
My cock eventually softened and slipped out of Bill's asshole. He turned over and I felt warm sticky stuff on his belly. "I came while you were fucking me," he whispered. We fell asleep in each other's arms.
We slept until almost 10:00 am. Bill rolled me onto my back and fucked me hard. After we'd both come, we took a long shower together, enjoying the feeling of our hands on each others bodies. I wanted to fix breakfast, but there wasn't any food in the apartment. We went out to eat. Bill insisted on paying. Then we went back to my apartment.
Even though it was Sunday, Bill said he had to check into his hotel and get ready for his sales calls tomorrow morning. He promised to call me if he had an evening free. I suspected that was a kiss-off, but I was wrong. We did get together for another night of hot sex before he left town. For several years, we saw each other every few months.
I gave him a final kiss and grope at the door, then went back to bed. As I drowsily recalled the pleasures of the last few hours, I realized that I had finally started making a new world for myself.
Copyright © 2003 by Ken James
This is a work of fiction. Names, characters, places, organizations, and incidents either are the product of the author's imagination or are used fictitiously. Any resemblance to actual persons, living or dead, locales, organizations, or events is entirely coincidental.
Many thanks to Wayde for his constant love and support.
Copyright © 2017 by Ken James