Over the years I have enjoyed reading the sizzling stories and letters Penthouse Variations prints each month. Hopefully, you’ll find an experience I had soon after graduating college worthy of publication. It all started with an ad for an apartment sublet.
I was on a tight budget, and so this spacious two-bedroom apartment seemed ideal. I’d be sharing one of the bedrooms with a guy named Kyle. The other bedroom was shared by a couple of guys who were seldom around but still paid half the rent. It was perfect.
I remembered Kyle from campus because he always had a hot-looking chick at his side. Once I moved in we became good friends, and I started to hang out with him and his entourage of beautiful girls. This improved my sex life dramatically, but it still couldn’t compare to Kyle’s. Every few nights he would have a new babe in his bed. Whether or not I was present, he’d screw them until their cries of ecstasy filled the air. He told me he managed to stay friends with all the girls he bedded by being totally honest, informing each one that he enjoyed variety and had no intention of settling down.
Anyway, one Saturday night after bedding yet another babe, Kyle exited the shower and accidentally dropped his towel. I couldn’t help but stare at the longest, thickest cock I had ever seen. Even flaccid it was impressive. As he was pulling up his briefs, Kyle looked up and caught me staring. I quickly turned away, pretending I hadn’t seen anything.
A few weeks later, we were getting ready to attend an outdoor party hosted by one of his girlfriends when it began to pour. When the party was canceled, Kyle got out his little black book and began calling around for some female company for the two of us. Amazingly, he was unable to find anyone, so we settled down in the living room with a couple of beers and watched a porn flick. As I hadn’t been laid in a while, the X-rated tape had an almost immediate effect on me, and it wasn’t long before I excused myself and went into the bedroom to jerk off.
Minutes later, I was working my stiff dick, and as I started to shoot my load I noticed Kyle in the doorway looking at me. Embarrassed, I quickly covered myself and fumbled to clean up. Kyle said something to the effect that I shouldn’t be embarrassed, and that even though he got laid frequently he still liked to beat off now and then. With that, he dropped his boxers and stepped out of them. Now, for the first time, I saw his cock fully erect, and I was rendered speechless. He was huge!
Kyle walked over to my bed and stood quietly in front of me for a few moments before saying, “Well, Jason, how ’bout giving me a hand here? What do you say?” I didn’t know what to say. Or do. This was an entirely new experience for me, one I’d never even contemplated. Finally, with my pulse quickening, I reached up and wrapped my fingers around that mighty shaft. I stroked it a few times, enjoying its heat and bulk, before Kyle asked me if I wanted a taste.
I had to admit to myself that I did, and so I lifted my head up off the pillow and pulled Kyle’s cock to my lips. I tongued the large, bulbous head and then licked up and down and all around the long, thick shaft. Finally, I opened my mouth wide and took in as much of Kyle’s cock as I could, which was still less than a quarter of it. But it was enough to start Kyle moaning with pleasure, and when I paused to stuff one of his come-filled balls in my mouth, his knees buckled and he had to grab the headboard for support.
Not much later, with his cock back in my mouth, I heard Kyle announce that he was going to come and felt him start to pull out of my mouth. For some reason, I refused to let him go, even trying to suck him in deeper, and then suddenly Kyle’s hands were on either side of my head and he was pumping his creamy semen down my throat. I started swallowing, as if chugging down a beer, and took all he had to give me, or so I thought. After three big swallows of Kyle’s come, I pulled away only to have my face painted by the subsequent spurts of semen from his cock. I took him back in my mouth, and the streams of come subsided to a trickle as I sucked him until he was soft. Never had he come so much in his life, Kyle said, and he was still thanking me when, blushing from embarrassment, I went to take a shower.
The warm shower spray felt wonderful, and I began to daydream about what had happened. Suddenly I heard the shower curtain being opened and Kyle came up behind me, reaching around to take hold of my hardening cock. He mumbled something about returning the favor as he knelt behind me and bent me forward. As I took hold of the hot and cold water shower handles for support, he pushed my feet apart and began licking my balls from behind while massaging my dick with his hand. When his questing tongue grazed my sensitive anus, a lightning bolt of pleasure hit me, and I moaned loudly.
Without warning, Kyle spun me around and swallowed as much of my cock as possible. He placed one of my feet on the side of the tub and began massaging my anus with his thumb. He pushed first one and then two fingers into my ass. As he worked my cock with his mouth while he finger-fucked my butt, I began trembling with desire. And when he stuffed a third finger in my ass I came with a loud moan, my semen jetting into his open mouth. Kyle swallowed it all.
After toweling ourselves dry, we walked naked into the bedroom where Kyle asked me if I wanted to continue. I answered by tugging his towel free and urging him onto his bed. I knelt beside him, facing away so he’d have access to my cock, and lowered my head to take his member into my mouth. He played with my cock, balls and ass as I sucked on his hard cock, then removed something from the nightstand drawer. Still sucking his cock, I felt something cold and wet being applied to my anus.
My mind raced as Kyle’s fingers invaded my asshole, and soon the sensations were so intense I could no longer pay attention to his cock. With my head down on the bed, cradled between my arms, and my ass sticking up, Kyle began finger-fucking me with one hand while stroking my cock with the other. And then suddenly I felt the plum-shaped head of Kyle’s monster cock being pushed into my virgin butt. Instinctively, I tensed up, and Kyle, as if comforting one of his girlfriends, told me to relax.
Somehow I managed to heed Kyle’s advice, and my asshole stretched to accommodate the head of his swollen dick. As he stayed still, allowing me to become accustomed to this new sensation, I could feel the excitement pulsing in his cockhead. With a firm hold on my hips, Kyle began rocking back and forth, ever so slowly working more and more of his giant organ inside my ass. When he felt that I was sufficiently relaxed, he quickened the pace some, pulling firmly on my hips as he pushed forward.
Oddly, I felt no pain, only a wonderful feeling of fullness, and as he buried himself to the root in my behind, his balls slapping against mine, my body began to convulse. I couldn’t believe he had buried that huge log of his in my virgin backside. The pressure was simply too much, and I could feel my anus contracting with each convulsion as I sprayed the bedsheet and my stomach with semen.
And now Kyle, responding to my orgasm, began fucking me hard and fast, sawing his big cock in and out of me with gusto. My asshole was stretched so wide I thought he would turn me inside out each time he withdrew, preparatory to his next vigorous thrust. Each time his hips crashed back into my ass cheeks, our balls would slap together loudly and his huge cock would be buried to the hilt in my rectum. And then came his final thrust, the deepest yet, and I could feel his come shooting into me.
Minutes later, with his come trickling out of my asshole and dribbling onto my balls, Kyle stroked my hair and commended me for having taken the entire length of his giant cock in my ass, something none of the girls he’d attempted to fuck anally had been able to do.
That was my first sexual experience with another man, and the most memorable simply because it was the first. But in the year and a half I lived with Kyle, I had numerous encounters with other men, all of them friends of Kyle, while at the same time I pursued pussy with great enthusiasm.
Ah, yes. Those were the days.
—Mr. J.E., Baltimore, Maryland