Hard To Explain

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Middle aged man fulfills a lifelong fantasy.
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timmywells
timmywells
1,745 Followers

I feel like an idiot because that's what I must look like, dressed like a third rate private investigator with a rumpled raincoat and a beat up fedora pushed as far down on my head as possible sitting in a Starbucks. The disguise, which is pretty much all this garb is, was designed to conceal my real identity because I don't know what I would do if anybody ever found out what I was planning on doing.

It's not that what I'm going to do is illegal - it's just that I'm ashamed of having had this fantasy all my life and never having had the guts to go through with it, until tonight that is.

It's a fantasy that I had actually experienced myself as a very young man, only that time I was the victim, if that's the right word for it. Victim sounds harsh because I wasn't harmed much at all, although I admit that I was scared. Maybe the fear was what made it special.

It was back in 1970, and a man who was about my current age managed to dupe somebody who up until then thought he was too smart to be taken advantage of. Me.

There I was though, blindfolded and naked in what turned out to be a barn out in the middle of who knows where, wearing handcuffs that were attached to a rope so high that I had to stand on my tiptoes to keep from dangling by my wrists.

"Don't be scared," the man told me more than once during the brief period of time he held me there. "I won't hurt you. I just want to enjoy you and then I'll make sure you get home safe and sound."

By enjoying me, he meant in a sexual way. I was not gay. I told him that before he gagged me, and I've maintained that all the years since. For someone who's not gay though, I not only had a couple of the most intense orgasms of my life in that barn, I've masturbated probably hundreds of times since then thinking about that hour or so. Now I'm about to have my livelong fantasy fulfilled, providing my young friend actually shows up.

I had tried to set this up one time before, but the guy either never had any intention of showing up or took a look at me in this Colombo costume and reconsidered. After all, what I'm asking is weird, and putting your faith in a total stranger to not hurt you and only do what he said he would takes a leap of faith.

I have a good feeling about this fellow though, because not only did we communicate electronically, I talked to him on the phone. He seemed like a charming lad, a student at a nearby college, but outside of learning that his name was Kenny I didn't want to know any more than that.

Kenny started to tell me more but I stopped him after he said he was 5'9". I wanted everything else to be a surprise when I unwrapped him, just like I was to that man back in the barn when he undressed me while I hung there helplessly.

That man hadn't been all that disappointed after he stripped me down, although he was a bit annoyed at the size of my dick, figuring a guy about 6' and 185 pounds would have something a bit more substantial between his legs. Join the club, I would have said if it weren't for the gag in my mouth at the time.

So all I know about Kenny is that he's a 19 year old student who just recently figured out he was gay and he's very much still in the closet. He prefers older men, and while I qualify there I made it clear that he wasn't going to be doing anything to me and would never see anything but my face when we first met.

I explained everything to him and told him exactly what I was planning to do to him and I was delighted when he had that it sounded like fun. Kinky but fun. Too trusting, I think, and at the end of the night I wanted to remember to talk to him about that.

"Sure sounds like you're gay," Kenny had said after I explained what I wanted to do to him and then informed him that I was not gay, and had a wife and two grown children.

"Sort of like something on your bucket list," Kenny said, and after he explained to me what that was, I had to agree.

"Must have been one hell of a good time," Kenny had said after I related much of what had been done to me that night almost 40 years ago. "For you to remember it so well. Still sounds like you must be gay, or at least bi."

Kenny's right of course. He knew me before he met me in that way. I've harbored feelings about men all my life, and pictured being with many of them but never pulled the trigger. Too scared.

Shortly after that day in the barn I got drunk with a friend and told him about what was done to me, and suggested that I would love to do that to him, and if he wanted, he could do it to me as well. That was the end of that friendship, sad to say.

So now I'm sitting in a coffee shop waiting for a guy who may or may show up, praying that I don't get recognized even though I don't live or work nearby. And Kenny thinks he's in the closet?

***

I knew it was him the moment he walked in the door, or maybe it was more like I was hoping it was him because he's beautiful. Fresh faced and boyishly handsome, and when he saw me he smiled this beautiful smile, probably because I looked every bit as goofy as I told him I would.

We shook hands and I offer to buy him a coffee or something but he declined.

"Too nervous," he says, smiling and when he does dimples appear.

Kenny also declines an envelope that I presented him. I had explained that he wanted to offer him something for his time, figuring that he could use the money for books or something, but while he had reluctantly agreed at the time, he had changed his mind.

"Doesn't seem right," Kenny explained. "Makes me feel like a - you know - if I took money. I'm just doing it because it sounds like fun."

"Okay," I said, putting it back in my pocket for now, and then decided to play father, or grandfather. "You know, you shouldn't be so trusting. I could be anybody, and while I promise you that I'm not..."

"I know who you are," Kenny interrupted, and over the next few minutes proved how much a savvy computer geek can find out about somebody if they want to.

"So it's not like I would just go off with somebody I never met," Kenny concluded, having put my name and other information in safekeeping in case I wasn't the nice guy I promised I was.

"Good," I said, not thrilled with having the kid know my real identity but happy he was cautious.

"Still going to be kind of scary though," Kenny said. "Being tied up and helpless, and naked in front of a stranger who can do anything he wants to you. I'm usually modest. Not much of a body."

"You're quite handsome," I assured him.

"Can we go now?" Kenny asked, but he wasn't in a hurry because he had anything else to do. "Kinda excited."

"Me too," I admitted as we left the coffee shop.

***

"Not your house," Kenny noted when we drove up to the darkened house on a very deserted road outside of the city, and as I drove up the driveway to the side of the barn I explained that it was a property I was trying to unload.

"You could scream all night out here and no one would hear you," Kenny noted as we entered the barn.

I had prepared the place much like I remembered the other place to be. I fired up a couple of lanterns for light and then showed Kenny the handcuffs that I had bought, and he smiled when he saw them.

"Don't struggle too much or they'll fall apart," I said of the novelty bracelets, which were nothing like the real ones that had been used on me back then, and after Kenny nodded I put the cuffs on him and then secured the blindfold over his eyes, making sure that he could not see out.

I remembered that being a particularly scary thing, to be blinded like I had been, but I also wanted to make sure Kenny wouldn't be able to see me as I did things to him, such was the level of my shame about my desires

My hand brushed his cheek as I blindfolded him, his skin so soft that I doubt whether he even shaved yet. So young and pure he looked, I mused as I pulled the rope down and secured the cuffs to it before yanking it up so his arms were fully extended upright.

"You're helpless now," I said calmly as I removed a handkerchief from a wrapper and told Kenny to open wide before placing it in his mouth to silence him.

I took a pocket knife from my pocket and made a tiny slit on the neck of the t-shirt he was wearing. I had told him to wear a shirt that he didn't want anymore, promising that I had one to replace it with, so with that in mind I grabbed the worn grey shirt and ripped it right down the

middle with a savageness that surprised me as well as my young friend.

That was how my own shirt had come off back then, only mine had buttons and after it was torn off me I had nothing to wear afterward. I managed to get the rest of it off of Kenny and stepped back to appraise my work.

Naked to the waist, Kenny's upper torso was quite slender, and with his arms raised his rib cage was clearly visible along with the sinewy muscles of his arms and shoulders. I took my own clothes off as I looked at my helpless prey, and by the time my boxers came down I had an erection like I hadn't had in a while.

Standing naked in front of Kenny was something I could never have done without the blindfold he was wearing. I had always had a bit of a problem with a lack of confidence about my body even when I was younger, and now that I was well into middle age the inevitable signs of the passage of time were showing.

I walked up to Kenny until my dick was bobbing right near him, and when I reached out and touched his chest he was startled when my palm made contact with his skin. Soft and creamy white skin, I noticed, and I was pleased with the absence of tattoos or scars.

Kenny's chest was hairless, and as my hand slid over his tiny pink nipples he shivered. I plucked the little nubs and heard him making garbled sounds through the gag so I twisted them a little harder before sliding my hands over to the wild sprays of medium brown hair that filled his armpits.

Kenny's entire body shivered as my fingers raked through the surprisingly furry hollows, releasing a gentle and not unpleasant scent as they went, and was pleased that his underarms seemed to be as sensitive as mine were. Leaning forward, I let my lips brush against the fine hairs, wondering what Kenny's reaction would be if I began to nibble under his arms like that man did mine years ago.

Later for that, I thought as my hands went down to the belt that was holding up his stonewashed jeans. My fingers were shaking as I pulled the leather from under the loop and undid it, and then went to the button of the jeans themselves.

I glanced down at my dick and was amused that I was drooling like a leaky faucet, with a long strand of pre-cum falling off as I watched. All it would take was a pull or too and I would come all over the place, but I wanted to wait.

The jeans button came free after a little struggle, and then I pulled the zipper down slowly, savoring the way my anticipation was building up, and the sound of the zipper echoed in the silence that otherwise was broken only by our heavy breathing.

With the zipper down, I started to ease the snug jeans down. Kenny was wearing grey boxer briefs and as they came down past his crotch I saw that Kenny was just as excited as I was, judging by the way his erection was reaching toward his hip.

Wasn't expecting him to be that big, I mumbled to myself as I looked at the impressive size of the organ in question before continuing to lower his jeans. They came down thighs that were slender and almost hairless, but below his knees his legs were quite hairy, especially on the insides of his lower calves. After I got his sneakers and socks off I got the jeans completely off of him and let my hands slide up his hairy legs.

"Do you shave your legs, son?" That was what the man had asked me back then, snickering as he had sensed my embarrassment over my lack of body hair, but that was not an issue with young Kenny.

That bulge got my attention again as I got myself upright once more. Just touch it, I told myself. He won't see you. He's helpless. My hand moved the bulge, and then stopped. And then again. I couldn't even do it with him blindfolded because doing that would be admitting something about myself. Something that I was ashamed of.

My hand moved again, and this time I made myself keep going. Kenny groaned when my hand made contact, and when I let my cupped hand follow the bulge, a little squeeze revealed that Kenny wasn't even hard yet.

That hissing sound was me as I sucked air in through my teeth while I felt the cock below the fabric pulsate as it grew and grew. Now the end of the bulge was over to his hip - what would this thing look like when I released it out of the cotton confines?

This wasn't part of my fantasy, but seeing that my captive was apparently hung like a horse was very exciting the more I thought about it. Too bad the man that took me didn't run into Kenny instead of me, because I think that he might have liked that more.

My hand had continued to stroke Kenny's manhood from the outside while he squirmed and shifted around. His arms and wrists would start to get tired soon, and unlike my captor, I was going to lower his arms after a while so he could get some feeling back in his fingers, but not yet.

My eyes went below the bulge, and when I brought my hand down there I felt was seemed to be a nice pair of balls. I could have just yanked down the briefs and seen, but this was the way I had fantasized about it, just imagining what I would find.

Judging by the feel I thought Kenny was circumcised, which was a good thing because I was as well and had no idea what to do with a foreskin. How big was Kenny's cock? Not very thick, but it had to be 7 or 8 inches long at least, and on his slight body that would look even bigger.

I stopped and went over to check Kenny's wallet, just to make sure I was playing around with an adult, and sure enough the lad was nineteen. He didn't look it, except for that snake trying to pop out of the cotton. That was definitely all man there.

That got me to look down at myself, at the modest sized twig and berries I was blessed with. They worked, which was something, and had produced two great children. My wife had never complained either, although maybe that was because I was her first and only. I recall seeing her expression when we rented some porn a while back and saw some of the outrageous endowments of the guys. Did she wish I was like that? She said no, that they were freaks and she was very satisfied with me, but was she just being nice? Love does that to you.

What would she think if I brought Kenny home with me? Look at my new friend, I pictured myself saying, and then imagined us all in the bedroom with my wife looking at the bulge I was becoming infatuated with more every second. I tried to picture her trying to deep throat Kenny like she did me. Too preposterous to really fantasize about actually happening, because we were certainly not swingers, but I found the idea arousing nonetheless.

My wife was more adventurous than I was, at least a little. In our early days we had a little time when we weren't getting along and she had gone home to her mother for a week. Upon her return she told me that she had something to get off her chest. She had cheated on me, and I was crushed. Then she said it was with a girl she had gone to school with. They had gotten drunk and messed around.

She was confused when not only wasn't I mad but wanted to hear all about it. I didn't think that was really cheating and still don't, but I had told her that I was entitled to fool around once on her too. She was fine with that but said it had to be with a another guy. I thought that was funny at the time, because back then all I had was a fantasy.

Now I had Kenny. He looked beautiful as he stood there stretched to the limit, and now I was going back over to him. It was time to take off those boxer briefs, and in a way I didn't want to. What if he had an ugly penis? Some of them are. Mine isn't. Mine is cute, or at least that was what the man had said that night. Cute.

Kenny was started to get fidgety, either from the uncomfortable position he was in or maybe he was excited and wanted release. Sweat was beading up on his forehead and a couple of droplets of sweat were trickling down his sides from his armpit jungles. It was time.

Shaking fingers took the elastic band at the top of the briefs and lowered them, first exposing a soap pad-sized tuft of pubic hair and then his cock. It sprang out wildly after the briefs passed it, startling me as it swayed lazily out in front of Kenny.

It was worth waiting for. It was even more amazing than I had fantasized it being. Long and sleek, the shaft was pale and smooth except for a vein that went halfway up before disappearing. Not thick, seeming to me about the same thickness as my own as our erections did a ballet of sorts without touching, and Kenny circumcised, with the glans shaped like a nose cone with only a small ridge.

"Your cock is beautiful," I heard myself say as my hand went out and touched another man's organ.

Kenny grunted as I felt another man's cock for the first time, and the warmth filled my palm as I felt him throbbing under my grip. I leaned forward and brought the heads of our cocks together, and when I rubbed my gooey tip into Kenny's I shuddered, and my new friend must have liked the well as well, although he might not have had a clue what it was I was doing.

I would never have done this without the blindfold, the rubbing of us together like this, because Kenny would probably think it was silly, not to mention the fact that this only amplified how much bigger Kenny was. It wasn't that fact that I found humiliating, because I enjoyed looking at the difference between us, but if Kenny could see me I would die of embarrassment.

When I had placed my cock on top of his and squeezed them together, he wasn't twice my size like it had seen, although there was a noticeable difference, especially in length, and as I looked at the head of my dick straining to reach further down his shaft I felt myself about to cum.

Maybe it was the visual effect, or maybe it was peeling his cock against the underside of my own, but whatever the reason I stood there helplessly while I ejaculated all over Kenny's cock and pubic hair.

Kenny had to have felt that because I heard him moan as I spurted all over him, the poor lad probably confused about what was going on. This hadn't been part of my plan, but once I started rubbing our cocks together it felt so good I lost control.

What I did next was part of my plan however. Kneeling in front of my captive, I decided not to bother cleaning Kenny up. I had tasted my own cum before, and didn't find it all that objectionable, and maybe it would act as some sort of lubricant. Since my mouth had suddenly gone a bit dry, that might be a good thing.

The problem was that I couldn't do it. Here I was, my face less than a foot away from Kenny's swaying erection, and I was frozen. Everything was right about it; there was no one there to see me, no reason to be self-conscious, and as for the penis in question, it was beautiful.

Play with this balls first, I told myself as I eyed the nice-size eggs hanging long in an elongated sack, and then they were cupped on my hand. Kenny moaned as I rolled the orbs in my hand, and then I leaned forward in a sudden rush of courage.

Nothing like I imagined it being, I thought as my lips slid down Kenny's dick, the warm skin pulsating in my mouth, and I managed to get halfway down before the tip of his dick hit my throat, causing me to gag a bit.

This was nice, I mused as I started letting my lips slide up and down his dick, leaving a little more than half of his organ wet. I wished that I was more talented at this, remembering how that man's lips went right down to the base of my dick as I hung there helplessly, but unlike me, Kenny did not cum right away.

timmywells
timmywells
1,745 Followers
12