First Fuck

































 Illustrations by Michael Kirwan 

 Story by Micheal Cardwell

originally published in Playguy Magazine -April, 1995 issue


He's got his face in the pillow and a tongue up his ass


As I lay in bed with my best friend, Dale Foster, I felt more than just a little panicked. I knew that whenever his other friends from school slept over, they would sleep in his bed, but now that it was me lying next to him, my heart thumped away like a kettle drum.

Dale Foster was the most gorgeous guy in our high school. He had every lovesick girl wallowing at his feet whenever he snapped his fingers. He was British, with only the slightest trace of an accent, which was kind of sexy. But he could be a pretentious jerk when he wanted to be.

Dale was only five-two and weighed about one hundred and thirty pounds, and he was as cute as you can possibly imagine. He had thin blond hair and one of those little boy faces that concealed the fact that he was actually eighteen, like me.

But his most striking feature was his lime green eyes. They had this way of mesmerizing you, especially in the dark--I swear they would glow like something out of a cheap, European horror movie.

He was always acting the part of the tough guy, and would be the first person to instigate a fight whenever we were out at a bar. I figured it was one of those things that's inherent in all short people: they figure that since they're "vertically challenged," they have to make up for it by being extra cool.

Anyway, Dale was my best friend.

We were both wearing just our underwear as we lay in his bed. Mine were a cheap pair of briefs, but he was wearing these real sexy Calvin Kleins, which outlined the massive dick he was always bragging about.

I was listening with forced interest as he listed all the girls in our graduating class the he wanted to fuck. I sort of grunted my agreement as he rattled them off, getting more and more depressed with each name he mentioned. But then he said something that really caught my attention, and I'll admit, made me skip a few breaths before responding.

"Are you circumcised?" he asked.

"Uh ... why do you ask?"

"No particular reason; just a question."

"Yes, I am." I said weakly, through the lump in my throat.

"Me too," he said. Then we both fell into this real uncomfortable silence.

I must admit that I was even more nervous now than when we first climbed into bed together. I could feel my prick beginning to swell, which terrified me. I would never be able to live it down if Dale found out that I had an erection while lying in the same bed as him. He'd tell everyone in school and I'd have to move to another country. Yeah, I know a best friend should be expected to keep a secret like that, but like I said before, Dale was a little bit of asshole.

"Have you ever thought about doing it with another guy?" he suddenly asked. I thought I was going to have a stroke right then and there.

"Uh ... no." I lied through my teeth.

"Yeah. Me neither."

Again we returned to that uncomfortable silence, which was probably the same atmosphere in Edgar Allen Poe's study while he was writing *The Raven*.

Though Dale was on the other side of the bed, I could sense the heat from his body seeping between the sheets and teasing the hairs on my exposed arms and legs. Man, I was getting hot. After a few, long moments of silence, I decided I should take a small gamble, and not allow the subject of sex to be dropped.

"Why did you ask if I ever thought about doing it with another guy?"

"Can you keep a secret?"

"Sure, we're buddies, aren't we?"

"Yeah, buddies," he whispered in this real cryptic tone.

"What's the secret?"

"I guess it's not really a secret. I've just been wondering lately what it would be like to get it on with another guy; you know, not to be a fag or anything like that, just to be able to know that I've tried it."

Boy, my heart was pounding against my chest now, and I was beginning to tremble from sheer panic. I didn't know what he wanted me to do, but before I could decide what route to take, he shuffled around in the bed, seemingly to find a more comfortable position. I could feel the tips of his fingers brushing against my arm, for a brief second. Whammo! I now had the biggest hard-on I'd ever had in my life.

I really don't know where I got the courage, but my voice simply spoke the words before I had the opportunity to analyze what I was actually saying. "Do you wanna try it?"

"Try what?" he asked.

"You know ... It."


Fuck, I hate it when someone knows what your saying, because it's so obvious, but pretends they don't. It pisses me right off.

"We could try and get it on together, you and I."

He didn't answer right away, but I could hear his breathing grow heavier, so I wasn't quite ready to die of embarrassment yet.

"If we try it, we have to make a pact that we won't tell anybody else," he finally said.

"I sure as hell won't say anything."

"Okay. So, what do we do first?"

"I don't know. Did you want to kiss?"

"Kiss you?"

"Do you see anyone else here?" I asked, braver now.

"Okay, but if I say stop, we stop."


Dale slid along the sheets until I could feel the warmth of his breath on my face. I fought back the urge to brush my hand against his groin to see if it was anywhere near as hard as my own. It would be smarter to take things slowly, I figured.

Our lips met in an awkward kiss that lasted only a second before he pulled away. It was one of those real lousy kisses where the lips barely touch each other and they're accompanied by that stupid smacking sound; sort of like the ones my grandmother gives me.

"Do you call that a kiss?" I asked.

"Sorry. Let's try it again." Again our lips met, this time for an extended period. I decided to be brave, so I slid my tongue into his mouth, which he hesitantly accepted. Slowly, he became more receptive, and he began to plunge his own tongue into my mouth. We were really getting it on with that kiss, and I figured we didn't need any more step-by-step instructions. I was ready to let myself switch into chaotic mode, but Dale pulled away again.

"Now what?" I asked, not doing a very good job of disguising my disappointment.

"Shouldn't we take off our underwear?" he asked quietly.

I didn't need an engraved invitation. I yanked off my underwear and tossed them off the side of the bed, then waited as he did the same.

I was completely turned on by the fact that we were now both naked under the bed sheets together.

"Now what?" He asked.

I really wasn't too sure what to do next, so I reached forward through the maze of linen until my hand discovered his massive cock, which was as hard as a rod of steel.

I couldn't believe this was happening.

I'll be quite honest: though I was still a virgin, I had seen a lot of pictures of guys with hard-ons. And none of them compared to the incredible tool that was attached to Dale.

He moaned softly, reached forward and took my hefty prick into his sweaty hand.

I slowly began to tug at his cock, while he did the same to mine. The only thing that I could think about was putting it in my mouth and sucking on it, like I'd always wanted to do with the guys in those magazines.

"This isn't so bad." He whispered, which drove me completely mad.

I could already feel myself getting ready to shoot my load, but I was determined not to rush the experience I had fantasized about so many times in the past, running cold water in the bathroom sink to disguise my jerk-off noises.

"Do you want me to suck your cock?" I finally mustered the courage to ask.

"Yes," he said without a second thought.

I slipped the sheets down to the foot of the bed, revealing our nakedness and highlighting Dale's shadowy, but very muscular body. I slid down the length of the bed until my face was right next to that monster cock of his. It stuck straight out at me.

I placed my lips against the quivering tip of his cock, then gingerly began to slide it into my mouth.

"Ouch, watch the teeth!" he complained.

"Sorry," I mumbled, finding it difficult to speak with his huge cock in my mouth, and impossible to pull myself away from it.

Then I ran my lips and tongue down the delicious shaft and was rewarded with his soft moaning. I can't really describe the taste of it with scientific accuracy: it was sort of musky and salty, but I do know that it was the best tasting thing that I've ever put in my mouth.

"Hold on," he insisted, as he pulled his cock out of my mouth. He sat up and turned over until we were in a sixty-nine position. "Let's try it like this."

Again I took his thick tool into my mouth and began sucking on it hungrily, relishing each time it touched the back of my throat. I almost jumped out of my skin when I felt his wet, warm mouth surround my own dick. I could feel the tip of my cock slide along his tongue and down his throat, while he made these real sexy slurping noises. I never thought anything could feel so good.

We sucked each other's cocks for a solid twenty minutes before Dale sat up again.

"Let's try something else," he suggested.

"Like what?" I asked, not really sure what else two guys could do with each other. Like I said earlier, I was still a virgin and my fantasies hadn't quite matured all that much.

"Do you want to try ass-fucking?"

"Ass-fucking? Do people actually do that?" I had frequently heard jokes about how homosexuals bum-fucked each other, but I thought it was just a myth, unable to comprehend what thrill such an act could give.

"I've heard that guys do it all the time," Dale offered. "Do you wanna try it or not?"

"I guess so." I answered hesitantly, the thought of his massive cock pounding up my asshole bringing visions of horrifying pain. "Who's first?"

"You can fuck me first," he offered, then rolled over onto his stomach.

I couldn't help thinking that he was acting real calm about this whole ordeal, while I was ready to puke because my nerves were fraying at the ends, and my stomach felt like a crowded trampoline.

"What do I do?" I asked while he lifted my leg over his so I was straddling his ass.

"You can try licking my asshole."

That one really blew me away. I wasn't too keen on putting my tongue up someone's butthole, but I figured that Dale pisses from his cock and I had no reservations about putting that in my mouth, so what the hell?

I crouched down so my face was pressed against with his tight little ass. I used my fingers to separate his cheeks to reveal his dark, tiny hole.

I carefully moved my face between his crack and gingerly planted my tongue at the entrance of his hole. The moan of excitement that he let out eroded any reservations I was feeling about performing this act. I lapped gently around the edge of his hole which made his entire body tense and caused him to lift his ass up higher, urging me to go further. With one eager plunge, my tongue bore deep into his wet, bitter asshole.

He shoved his face into his pillow to muffle his cries of excitement, since his parents were sleeping in the next room. I began to use my teeth and tongue simultaneously, until I was literally eating out the tangy juice from his ass.

"Oh, that is so fuckin' nice." I heard his voice squeak from within the pillow.

He emitted a long sigh as I pulled my tongue out of his ass and repositioned myself. I slid forward along the length of his legs until I was straddling his thighs and my cock bounced teasingly on the cheeks of his ass.

"Wait a second." I interrupted. "Shouldn't we be using a condom? Every time I turn on the TV, they're talking about safe sex."

"Yeah, I guess." He grunted. "There are some condoms in the drawer of the night table."

I reached across the bed and opened the drawer. I had to dig through a collection of chocolate bar wrappers and unreturned library books before locating a condom. I removed it from the packet and clumsily slid it down the length of my cock.

"Okay, it's on." I said. "Are you ready?"

"Hold on," he said, stopping me as the tip of my cock tapped the entrance of his hole.


"I think we're supposed to use Vaseline or something like that."

"Vaseline? For what?"

"So it doesn't hurt as much."

"It's supposed to hurt?" I wondered aloud.

"Only a bit."

"Then why are we going to do this if it's going to hurt?"

"Because it'll feel better once we get going." He seemed sure of himself.

"Are you sure you haven't done this before?"

"Not that I remember," was his evasive reply.

"Do you have any Vaseline?" I asked.

"No, but I've got some lubricant in the same drawer. It's in a little tube."

I again reached across to the drawer and found a gnarled tube of lubricant. I unscrewed the top and squeezed a healthy portion of it into my hand. I massaged it over the condom, and down the shaft of my cock, which was a turn-on in itself. When my cock was thoroughly greased, I returned the tip of it to the lips of his asshole.

"Okay, now put it in real slow," he instructed.

I pushed in gently, and felt his whole body tense up. I was only in an inch, but I was feeling this sort of resistance--I wasn't sure if I should continue.

"Okay, a little more," he whispered.

I obeyed by pushing forward another three inches until I hit a second barrier and figured that I couldn't possibly go any further.

"Okay," he said through gritted teeth. "When I count to three, I want you to shove as hard as you can until you're all the way in. Ready?"


"Okay. One ... two ... three ... shove!"

I rammed forward and was surprised at how easily my cock slid the rest of the way into his asshole. He again planted his face in the pillow and I could hear his muffled cry of excitement as my balls slapped against his ass-cheeks.

I began to pump him slowly at first, relishing each forward thrust; but as the animal in me began to take control, I started thrusting harder and faster, completely overcome by the sensation of fucking my best friend up the asshole.

"Oh, I'm going to cum," I grunted, preparing to pull out of him.

"No, keep your cock inside of me," he insisted.

I wasn't going to ask any questions, and kept hammering away at his asshole until I felt the explosion of my cum shoot up the cavern of his ass and fill the condom. When I at last pulled out of him, I collapsed on the bed, completely exhausted. I slid the soiled condom off my dick and tossed it upon the night table next to the bed.

"You're not going to sleep yet," he informed me. "Turn over onto your stomach. It's my turn."

I followed his instructions, then held my breath as I felt his tongue begin licking my ass-cheeks. If I had any doubts about the sexual legitimacy of rimming a guy's hole, they were gone now. The series of shocks that raced through my body as his tongue bore into my ass was incredible. I could feel his teeth gently biting as his tongue eagerly slurped and smacked. I gasped and moaned with delight as he had done when I had performed the act on him.

When he stopped at last, I thought for sure I was going to die of exhaustion.

Then I heard him digging through the drawer, where he located another condom. He unwrapped it and I could hear the sound of the latex being yanked down the length of his enormous cock. Lastly came the squirting noise as he squeezed the tube of lubricant.

I closed my eyes and clenched my teeth in anticipation of total pain. I felt the tip of his cock reach my asshole.

"Go slowly," I begged.

He responded to my plea by ramming his monstrous tool into my hole with a single, savage thrust.

I forgot to bury my face in the pillow to muffle my ear-piercing scream, but Dale didn't seem to mind. He began to fuck me with a frenzied intensity that was a blur of sensations to me. But the pain soon subsided and was replaced by waves of pleasure that rushed through my body, each time his cock drove deeper inside of me.

The entire bed was rocking chaotically as he fucked me. Part of me wanted him to ejaculate so I could end the strange sensation that consumed me, while the rest of me wanted him to continue fucking me forever. Then the bedroom light switched on! I was horrified to look up and see Dale's mother standing in the doorway with a peculiar, indescribable expression on her face. I thought I was going to die of embarrassment at that very moment. There we were, completely naked; Dale on top of me with his dick buried deep up my asshole. I was too shocked to move.


"Again, Dale?" she asked in this tone of voice that reminded me of the voices you hear on those boring documentaries.

"Get out, mother," he snapped. That really killed me. If I ever talked to my mother like that she'd literally yank my head off my neck.

"I said, get out!" He was practically screaming at her.

She shook her head as if to say "I give up," then turned off the light and gingerly closed the door behind her.

"Sorry about that," Dale whispered in my ear as he began to plunge his cock into me as if nothing had happened.

"What did she mean by 'again'?" I asked.

"Nothing," he said, then began to increase the intensity of his assault until he was really fucking me hard.

It was incredible to feel his giant cock forcing itself inside of me, and I forgot about the interruption of his mother.

He gave a loud grunt, and I felt his body convulse on top of me; then I felt a hot load of his thick cum fill the condom in my asshole. It was the most incredible sensation that I had ever experienced.

When he was finished, he carefully pulled out of me, then rolled over onto his side until he was facing me.

"What did you think of that?" he asked with a gorgeous, sheepish grin. He peeled the condom from his dick and tossed it onto the night table next to mine.

"It was incredible," I whispered.

He responded by sitting up next to me until his prick, which was already beginning to grow again, dangled over my chin. He began to jerk off, thrusting his hips forward and ramming the tip of his cock at my face; sometimes slapping it against my cheeks and sometimes against my mouth. I opened my mouth in hopes of taking it, but he pulled it away before I could wrap my lips around it.


I was hypnotized by this amazingly erotic performance, and then a new load of hot cum shot out of his dick into my face. The bed shook and squeaked as he collapsed beside me once again.

He reached forward and wrapped his arms around my naked body, which was the first time during our encounter that I actually felt relaxed. He pulled the blankets up to cover our angled embrace and placed a soft kiss on my forehead before letting his head fall to the pillow.

"Can I stay over again next week?" I asked. I wanted him to feel the same emotions that I was feeling towards him. The thought of rejection at that moment would have killed me.

"Greg Taylor's staying over next week," he said, and then with a devilish smirk added, "but you're invited to join us."

I rolled over and drifted off to sleep, not a virgin anymore.


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