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Never Did This Before

Category: Gay Male
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“Never did this before,” I said, as my new friend Jesse pulled my shirt up over my head, exposing my pale, hairless chest which was in stark contrast to the one of the man who was undressing me.

“I know,” Jesse said quietly. “You told me that already. Relax, Tim. No reason to be afraid.”

Not only was Jesse in his middle 20’s, making me about 20 years his senior, but the young man was in superb shape, his upper torso like that of a weightlifter with the bulging muscles in his shoulders and chest visible even through the thick black hair that covered him from his neck down, front and back.

My fear was clearly evident, not only given away through my trembling hands but from the sweat that had my skin glistening despite the coolness of the motel room we were in, and it was only the fact that Jesse was being so nice and understanding that kept me from bolting out of the room and into the night.

Jesse’s hand were on my belt, undoing it and then coaxing my slacks down off of my legs, leaving me with only my baggy boxers protecting me from being totally naked.

We had been taking turns in taking each other’s clothes off, and now it was time for me to take Jesse’s jeans off. He stood up in front of me, looking even taller than the 6’2″ he claimed to be, and as I leaned closer to the edge of the bed my butt was perched on, my hands struggled with the button that secured his snug jeans.

“I have trouble with that too,” Jesse said about the button, which was probably a lie designed to make me feel less pathetic than I was, and mercifully it opened up.

Jesse’s zipper made a roaring sound as I pulled it down, or at least that’s what it sounded like to me, and as I tugged the pants down I could smell the manly aroma of him that was released.

My face was directly in front of Jesse’s crotch, scant inches away from the black boxer briefs, and I was unable to contain the gasp that escaped my lips as I stared at the outline of Jesse’s cock which was very evident through the snug cotton.

I managed to stop gawking at the massive bulge long enough to get the jeans off of Jesse’s profusely furry legs, but as I straightened back up my eyes went right back there.

“It’s okay,” Jesse said. “Here.”

Jesse reached down and took my hand, bringing it up and placing it right on the bulge that ran down the inside of his right thigh. I felt the heat that oozed from the penis on the other side of that cotton; a penis that was still soft, I discovered as I let Jesse guide my trembling hand down the length of his organ.

“Unbelievable,” I managed to say in a breathless voice as Jesse let my hand go when he found I was able to move it on my own.

“Told you I was kinda big,” Jesse said as he looked down as my awkward massaging of his cock.

Indeed Jesse had done just that when he answered my ad that brought us together. It had been a very simple ad that I had placed in an alternative weekly paper, expecting to get maybe one or two responses.

“Middle aged man,” the ad had read. “Very shy and nervous. Small build. Always curious but never willing to try before. Seeking patient guy to help me experience being with another man for the first time.”

It was completely honest in every way. I had been curious all of my life, but kept my desires hidden under the charade of my marriage. With that gone, and me not getting any younger, I thought that the time had come.

The nondescript ad, hidden in the back of this free rag that I assumed nobody read, got 24 responses in the first few days. So many that I stopped the ad before it ran again. Jesse’s was one of the nicer responses, and when I wrote him back I made sure to explain that when I said in my ad that I was small, I meant that I was small all over.

“That’s good,” Jesse had replied. “I like men built like that. I’m big – all over.”

His hands on his hips, he exuded confidence but not arrogance as he seemed to enjoy my awe of him. I guess it was an example of how naive I was, but I had no idea a man could be so well endowed. Oh sure, I remembered in my youth taking showers in gym class and seeing the wide variety of sizes of their genitals, but seeing it was one thing and having the evidence right in one’s face was something else altogether.

“Can we turn the light off?” I asked – pleaded.

Jesse smiled and went over to the light switch and turned the dial so that the lamp was dimmed but not off. It was still too bright for me but it was better than it was before, and as I watched Jesse’s muscular body walk back over to the bed I knew that the moment was at hand.

How I dreaded this moment. In a matter of seconds my boxer shorts would be coming down, and my shortcomings would be revealed to Jesse. While he was being so nice that I pretty sure he wouldn’t laugh, this was still terrifying to me.

Jesse eased down and sat next to me on the bed, the coarse hair of his thigh tickling my bare skin, and as he leaned toward me his hand came onto my bony knee, gently squeezing it in his meaty paw.

“Relax,” Jesse said, leaning over and kissing me.

Our lips met as I experienced my first kiss from a man, and if I didn’t know better except for the roughness of his five o’clock shadow I wouldn’t have been able to tell the difference. When he felt me responding, Jesse turned up the passion, parting my lips with his tongue in search of mine.

Jesse’s hand left my thigh and moved over to my boxer shorts, and unlike me, when Jesse probed around my underwear he had a bit of trouble finding my dick, which made me even more nervous.

“Ah! There you are,” Jesse sighed when his fingers finally got hold of my little toadstool, which was trying to retract into my intestines from fear, and after rubbing it for a few seconds I felt the clasp of my boxers come open, giving Jesse a bit more room.

I saw Jesse glance down at what he was holding, but while he smiled he didn’t laugh, and instead kept massaging my dick while leaning over and nibbling my neck. To my surprise, Jesse’s comforting touch began to make me relax, and soon I felt myself responding to his touch.

“Tim,” Jesse whispered in my ear as his fingers slid up and down the shaft of my stiffening dick. “You’re not that small. You’ve got a beautiful cock.”

That was a lie, because I knew I was small. My wife had called it my “little Dickie” for years. In the beginning she said it affectionately, but later used it derisively, blaming my small penis for our inability to have children as well as most of the other problems of the world.

As it turned out, it wasn’t my fault that we couldn’t conceive, but hers, but by then it didn’t matter and it was probably just as well we didn’t have kids. In the end, as the private detective discovered, my wife had sought satisfaction with a man better equipped to serve her needs, and that brought our marriage to a merciful end.

That was then, and this was now. There was nothing negative coming from Jesse, who seemed quite happy with what he was holding no matter how little it was, and when he eased me back onto the bed I felt his mouth envelop me. His moist lips slid right down until they were nestled in the tuft of pubic hair that I had trimmed in a futile effort to make me look bigger.

Our eyes met as he looked up at me, and he kept looking at me as my dick throbbed in his mouth. His lips slid up to the gumdrop sized head of my member, his tongue toying with the sensitive tip, before his lips slid down again.

My wife had given me oral sex from time to time, but what Jesse was doing went far beyond anything I had ever experienced. Jesse sucked on my balls tenderly, rolling my nuts around in his mouth and making me groan with pleasure before going back to my dick.

My orgasm surged through me so fast that I didn’t have time to warn Jesse, and if I ever did that to my wife she would have thrown a fit. Instead, Jesse seemed to want me to cum in his mouth, and it felt like he was trying to siphon every drop of my seed as he kept sucking until I was drained.

Jesse released my withered little stem from his mouth after it went limp, pausing to flick the tip of my dick playfully with his tongue before looking to me for approval.

“That was – amazing,” I managed to say as Jesse got up on his knees.

“Did you ever taste your own cum?” Jesse asked, and I shook my head no. “It’s sweet. Here.”

Jesse leaned up and kissed me, his semen coated tongue dueling with mine, and I had to admit that it wasn’t bad. I realized that my hands were on Jesse’s shoulders, rubbing his rock hard biceps, and the feel of his hairy body had a strange appeal to me.

It was my turn, and I tried to remember what Jesse had done to me as he climbed off the bed and began to take his boxer briefs off.

“Please,” I said, sitting up on the edge of the bed in front of him. “Let me.”

My fingers were shaking as I grabbed the elastic of his briefs and began to pull them down slowly. It was like I was unveiling a statue, and while I was scared I was also excited, wanting to see what was underneath the black cotton.

Hair. More of the jet black hair that grew so abundantly everywhere on Jesse, and then the hair stopped. It seemed that Jesse had done a little trimming himself down here, but the effect Jesse’s gardening had was far more striking.

The olive-toned skin below his pubic hair and above his penis was smooth, and then the base of his penis came into view. To say that the base of his manhood was thick would be a grand understatement, because it was just about as wide as my wrist.

A couple of gigantic veins wound their way down the shaft of his cock, which mercifully tapered somewhat. Down and down the briefs went, and just when it seemed that there would be no end to the anaconda-like organ that I was exposing, the entire cock was finally revealed.

Jesse was uncircumcised, and perhaps that added to the stunning visual effect of his manhood as I coaxed his briefs down his legs. It was like I was hypnotized by the sight of what looked much like an elephant’s trunk that hung straight down between his legs, a cock that even limp dwarfed mine at it’s hardest.

His dusky foreskin was long, completely hiding his head of his cock, although the shape was visible under the shroud. The crinkled foreskin almost wrapped around the head of his cock, and I was so unfamiliar with what to do with him that I looked up to Jesse for help.

“You don’t have to do anything if you don’t want to, Tim.”

“I want to – it’s just…”

My right hand reached over, touching the shaft of his member gingerly. I know that I must have seemed more like a child instead of a man approaching 50 years old, but I couldn’t help it. It was like Jesse was of another species, and it crossed my mind that I might have been more comfortable if Jesse had been built more along the lines of an average man instead of the astonishingly well endowed Adonis before me.

“That’s it,” Jesse was saying. “Your touch is nice.”

My hand was now around the shaft of his flaccid cock, or at least almost around it. It was warm and felt gelatinous as I lifted up the weighty tool. His foreskin slid back as I did, exposing the pinkish tip of his glans, and Jesse’s hand came down on mine, retracting the foreskin completely and revealing the entire bell-shaped crown.

I leaned forward, feeling the warmth of him before my mouth touched his skin. Jesse had an earthy, musky aroma that I found arousing, and as my lips touched their first penis, my breathing was so heavy that I thought I might hyperventilate.

Jesse’s hand. His fingers were running through my thinning hair, and his touch had a calming effect on me. It was as if he was telling me that I was doing fine and that this would be something special that I would remember all of my life. It was.

I had to remember to watch of teeth, but Jesse didn’t complain when I accidentally scraped his glans a couple of times. My jaw was already aching after a minute of trying to take his gigantic member deeper into my mouth, but it felt so good to actually do what I had fantasized about much of my life that I ignored the discomfort and tried to take more of him in.

Jesse began to get hard, and as he did I found that it was getting easier to handle his cock. When Jesse eased down onto the bed on his back, his bronze manhood was swaying in front of him, almost straight out.

Now I found myself kneeling at Jesse’s hip, his gigantic, muscled cock back on his stomach. I pulled his erection upright, both of my hands wrapped around the shaft, and bowed my head down. I discovered that I was able to take all of his cock that my fists didn’t cover, and as my head bobbed up and down, I began to spin my hands around his throbbing shaft.

Jesse’s voice was soothing, telling me how good I was doing, and then his hand was pulling my backside up towards him. He had my balls in his hand and was gently kneading them, and this made me remember that Jesse had a pair too, and what a pair they were.

Encased it an elongated pouch, his golf ball-sized balls were meaty and loose in their furry sac, and Jesse moaned his approval as I played with them, encouraging me to really squeeze them hard. I did, fearing I would hurt him, but he reveled in what soon became the mauling of his scrotum.

Jesse’s cock was now fully engorged. Unlike mine, his erect penis hadn’t doubled in size when it got hard. In fact it really hadn’t got all that much longer and thicker in the process, but considering how enormous it had been to begin with, that was a good thing.

“Here,” Jesse said, his muscular hands pulling me up further until I was straddling his face. “I want to taste you. You’ve got an incredible ass.”

I shivered when I felt Jesse’s tongue sliding up and down the ridge between the base of my sac and my butt crack, losing my balance a bit. I let my tongue slide up and down the underside of his cock, marveling at the sinewy roots at the trunk of his cock while his tongue went further.

Gasping, I was about to tell Jesse that he had gone too far by mistake, until I realized that it was no mistake. Jesse’s hands were spreading my ass cheeks, and then I felt the wetness of his tongue as it danced along my anus.

Trying to keep sucking his cock while this was going on was tough enough, but when his hands pried my buttocks apart farther and his tongue stopped licking and penetrated me, I was clutching the bedding.

What a sensation this was! Jesse’s tongue felt like a snake inside of me, probing and spinning and making me feel things I had never felt before. Looking up at what he was doing, his face was hidden but my dick was pointing down at me, fully re-energized.

Jess had discovered that as well, and he pulled a hand around and took my dick between his thumb and index finger and began pulling on it hard . In no time at all, I felt the familiar tingling and watched my dick spurting my milky seed all over Jesse’s chest and stomach.

“I’ve got to have you,” Jesse said, and while I didn’t know what he meant by that as he crawled out from under me, I was soon going to find out.


Jesse had fished around in his pants pocket, and when he came back onto the bed with a tube of something, a chill went down my spine.

“It’s going to be alright,” Jesse said as he positioned me the way he wanted me, on my back with a pillow under the small of my back.

Jesse’s lubricated finger was in my ass, plunging through the tiny puckered ring like his tongue had earlier. His finger probed deeper, much deeper, and then there was another finger, spinning deep into my bowels while I lay there afraid to speak, my hands gripping the back of my thighs and spreading them apart like Jesse had instructed.

I would have been even more terrified if I actually thought that he was doing to do it, because as I watched his lubricating efforts go to himself, coating his cock with gel as he pumped his swollen member, I knew it was impossible.

No way could something that size fit into something so tiny like my anus. I mean, I knew that guys did that to each other, but not with a man built like Jesse. It defied logic, and that what I thought right up until it happened.

“I’ve wanted your ass all night,” Jesse said. “Just relax for me Tim.”

“Please,” I whimpered, but I didn’t know if I was pleading for him to stop or not.

“I’ll turn you over in a while,” Jesse explained. “I just want to see your face when my cock goes into your ass for the first time.”

As I felt the tip of Jesse’s cock against my anus, it suddenly occurred to me that this was really going to happen. I felt my asshole being stretched beyond belief as he leaned forward, ripping and tearing my virgin orifice, and I think I might have screamed when the head of his cock popped inside of me.

“You okay, Tim?”

I think I might have blacked out, or fainted for a second, and when I came to the searing pain in my ass was indescribable.

“Hurts,” I said, ashamed that there were tears coming out the corners of my eyes as I lay there helpless underneath Jesse.

“You’ll get used to it,” Jesse said softly. “You’re so tight.”

“Is it all the way in?” I asked.

“No,” Jesse said with a smile. “Not even close. See?”

With that, Jesse eased toward me, and it was if his cock was skewering me as he pushed another inch or two inside of me.

“Want to turn over?” Jesse said.

“No,” I grunted. “This. Like this.”

For some reason, I wanted to see him. I wanted to watch this Adonis as he fucked me, and as he began to move a little harder and faster, penetrating me deeper and deeper with every stroke, I began to want it more and more.

Soon it felt that Jesse had fully impaled me, and I had let my thighs go and was now scratching and clawing at my lover as he fucked my ass hard.

“So good,” Jesse grunted, the sweat from his hairy body spraying all over me like rain. “Gonna cum.”

With that Jesse arched his back and cried out. I could feel his cock twitch inside of me, and then I felt a soothing warmth inside of me as his cum filled my rectum, coating my bowels with his seed.

Jesse stayed suspended over me as we looked at each other while catching our breath. I felt his deflating cock slithering out of me, finally popping out as Jesse straightened up.

“You okay?” Jesse said. “I was afraid I had hurt you.”

“You did, but it hurt good, if that makes any sense.”

“I had to have you,” Jesse said. “You’ve got such a cute butt.”

“Feels like you’re still inside me,” I said when I tried to get up, and Jesse jumped out of bed and helped me walk to the bathroom.

We showered together, and by the end the pain had turned into a dull ache. We lathered each other with tenderness and care, and by the time we went back to bed, the other bed in the room, I was ready for more.

“Mind if I play?” I asked.

“Be my guest,” Jesse said with a smile as he reclined with his hands behind his head.

I climbed on top of him, wrapping myself around him as I savored the fresh scent of his magnificent body. The feel of his body hair against my skin was almost intoxicating, and as I rubbed myself against him I could feel my erection blossoming.

I kissed and bit playfully at Jesse’s nipples, and even let my mouth travel over the the wild jungles of hair that filled his armpits, licking and chewing the thick growth while holding his bulging biceps in my hands.

“Ooh,” I said, noticing that my dick was rubbing against the underside of Jesse’s flaccid cock.

“Feels nice, doesn’t it?” Jesse said.

“This is weird, right?” I asked, hoping that Jesse didn’t think it was stupid for me to enjoy the feel of our cocks rubbing together as much as I was.

“No, this is nice,” Jesse said, moving his hips into me. “Your cock is so hard.”

I lifted my upper body up off of Jesse so I could look down, and while the sight of my tiny pale staff rubbing against Jesse’s enormous bronze member only accentuated the absurd differences in the sizes of our organs, I didn’t feel ashamed of my body anymore.

Jesse had accepted me completely, and had treated me with love and respect. It was funny in a way that for the first time in my life, I felt like a man, and I had to be with another man to enjoy that feeling.

“You’re going to cum, aren’t you?” Jesse said, bringing his hands up to my nipples and squeezing them lovingly.

“Yes,” I gasped.

“You’re getting me excited again, you know that?”

“Yeah,” I wheezed. “I can feel your cock getting hard.”

“I want to feel you cum all over me. All over my cock.”

I looked down as I spurted all over Jesse’s cock and pubes. It was a much less impressive load this time than before, but it felt just as good, and when I finished I began to move down to the foot of the bed.

“Where are you going?” Jesse asked.

“Have to clean up my mess,” I declared, lifting Jesse’s gooey, semi-turgid cock up off of his belly.

“Then,” I continued just before lowering my head. “I plan on finding out what somebody’s semen tastes like. Besides my own, I mean.”

For the record, it tatsed delicious.

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