Friend of the Family

Story Info
Snooping teen gets caught being naughty.
8.8k words
4.45
101.1k
33
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
timmywells
timmywells
1,749 Followers

Don Strong wasn't really my uncle, even though my folks had told me long ago that I could call him Uncle Don. What his actual relationship was with my family was unclear to me back in 1969, the time that the events in this story took place, and since everybody that would know all the details is dead now, I guess that's it's a mystery that will remain so forever.

This story involves me doing something I shouldn't have been doing, and the resulting consequences of my actions. It was a dreary Saturday morning in April, when it was too wet and cold to go outside, and I was bored.

*******

Chapter One: Snooping.

Forty years later, and I still remember just about everything that I did on that day. I had just taken a shower, and after drying off I had put on my robe and was walking down the hall to my bedroom, enjoying the rarity of having the house to myself.

My folks had taken off, heading to Montgomery Ward where they would probably be spending the day window shopping. I had politely declined their offer to tag along, but judging by the silence in the house, my Uncle Don went with them.

He wasn't really my uncle, just a friend of the family I guess, but to me he was just a pain because his only redeeming quality was his ability to burp louder than anybody in the world. I guess my folks liked him around, because he was at our house all the time, or at least every other weekend. When I was young my parents had me call him Uncle Don, and it stuck over the years.

Don was a tall and skinny guy with grey hair that he wore in a brush cut, and his arms were covered with tattoos which were mostly hidden by the billowing white hair that coated them. Uncle Don and my folks would play cards and drink beer at the kitchen table until all hours of the morning on the weekends he visited.

For some reason that Saturday morning I went down to the end of the hall, which was where the spare bedroom was. We called it a spare bedroom but it was pretty much Don's, and what I think I was really going in there for was to see if he had a pack of cigarettes around so I could steal one.

He smoked Pall Mall's, nasty unfiltered cigarettes that I hated, but any port in a storm. To be honest, I didn't even like to smoke, but did it back then on occasion when I was with my friends so I would look as cool as them. It was a habit I never really developed and dropped completely soon after this, but anyway, that was why I was in Uncle Don's room.

I didn't see any cigarettes laying around, and wasn't planning on snooping through his stuff or anything to try and find one, but something caught my eye when I went past the night stand so I stopped to see what it was.

That was my first mistake.

******

Chapter Two: First exposure.

The title of the paperback was 'Sailor's Shore Leave' and it was a bit larger than the standard paperbacks of the day, a precursor of the trade soft-covers of this era. The cover had a guy in a goofy looking sailor's cap with his arm around another guy.

When I opened it up, I was stunned at what was inside. There was very little story, only a sentence or two every few pages, but what there was were pictures. A whole lot of pictures; grainy black and white photos that showed the two guys on the cover and how they spent their day.

They started out with their clothes on, but after a few pages the clothes were history, except for that goofy sailor's cap the one guy wore, but even that disappeared after a while.

I wasn't completely naive, but this was 1969, mind you, long before the Internet, VCRs and everything else. I was 18, but I think that today there are kids half as old who know a lot more about sex than I did.

The first few pictures of the guy doing things to each other, I understood. I had done these same things with my friend Tom. We had played with each other's dicks plenty of times, and as I looked at the guys I wondered whether I would dare show this book to Tommy, since the guys were a lot like we were. The guy in the sailor's cap had a short fat cock like Tom, while the other guy had a pretty big one like me.

As I continued flipping the pages, the guys started doing a lot more than jerking each other off though, and soon they were doing things to each other that I had only heard about - graphic and disgusting things that offended me so that I had to hold the book with one hand while my other hand went between the folds of my robe.

I was just about to take this book back to my own robe so I could get myself comfortable and jerk off once or twice with these pictures as inspiration - or probably spend the whole day whacking off - when the floorboards squeaked behind me.

I was just about to shoo my cat Walter out of the room when I realized that it wasn't Walter behind me. It was Uncle Don.

********

Chapter Three: The jig is up.

"Getting an eyeful, Skipper?" Don asked, his raspy voice echoing in the tiny room.

"Uh - sorry," I said, setting the book back on the night stand, or at least trying to.

I picked it up off the floor and set it back where I had found it, but when I straightened up Don's long, bony hand was on the back of my neck.

"Going through my stuff, huh?"

"No," I said, which sounded as stupid then as it does now.

"Then what the hell ARE you doing?" Don wanted to know, the grip on my neck tightening.

"Just - uh - looking for a cigarette," I said.

"Then you WERE going through my stuff," Don correctly concluded. "Ever hear of asking?"

"I thought you went to Monkey Wards with my parents," I said, calling the store by the name my folks used around the house.

"Your old man is getting his brakes done, so he'll be stuck there with your mom all day. Lucky I didn't go, or else who knows what you would have done," Don said. "Probably would have shot your spunk all over my things."

"No - I was going to take the book to my room," I whined. "I was going to bring it back. Honest."

"With the pictures all stuck together, I reckon," Don sneered, and as he tried to look over my shoulder in the area my hand was now hiding, he added, "You like what you saw in that book?"

"No," said with as much indignity as I could muster. "It's gross."

"I'll bet you and your friend - that husky redheaded guy that's always hanging around here - could make a book like that," Don suggested, his grip turning into more of a rough kneading of my neck. "I figure him for a bottom. That right?"

"Huh?" I asked, not having a clue as to what he was talking about.

"When you two fuck, I'm betting that he's on the receiving end," Don explained.

"What? We don't do anything - or even know anything about the stuff in that book," I protested, but even though I was being honest, having been caught in a couple of lies already, the truth was not going to set me free.

"What's your father going to say when he gets home and I tell him about what I caught you doing?" Don said caustically.

"You can't tell him this," I pleaded.

"And your mother?" Don sneered. "I can picture her reaction."

"Please!" I begged, thinking about what a living hell this house would become. "You can't. My life will be ruined."

"Okay, I won't tell them," Don said, lightening the hold he had on my neck.

"Thank you," I gasped, my neck sore but I was so grateful to him that I swore I would never make faces at him behind his back again.

"Time we got to know each other a little better anyway, Paul," Don said, and as he spoke I felt his hand come off of my neck and slide down the sleeve of my robe.

"Oh! Uncle Don?" I gasped when Don's hand reached around and inside the opening of my robe, grabbing my now-flaccid cock and giving it a series of long, slow pulls.

"Hefty hunk of meat you've got on you there, Paul," Don whispered in my ear as he leaned over me to look down at what he was holding, and when my eyes went down, the sight of Don's long, bony fingers wrapped around my cock was so unreal I was at a loss for words.

"Now get that robe off," Don said, releasing me from his grip and moving over to the door, which he closed and locked before turning to face me.

******

Chapter Four: The unveiling.

Don repeated his words, which was not a suggestion but more of a command, and stood there by the door with his arms folded, waiting for me to comply.

"I can't," I whimpered as I held my robe together. "I'm naked underneath."

"No shit," Don said. "Take it off, unless you prefer I have a talk with your folks."

I had some major self-esteem issues concerning my body back in those days, and not without reason. At 18 I was a year away from getting a little involved in weight lifting, and while my 5'10" frame wasn't obese, in would be fair to say that I was a bit soft.

Thankfully, the rest of me was alright. After what seemed like the worst case of delayed puberty on the planet, things finally started to happen and when they did, they did in a good way. I found out that I was pretty well hung, or at least I was according to Tom when we began to get together.

When I asked Tom how he knew that, he clammed up, and that was my first inkling that there was a lot about Tommy I didn't know. I would eventually discover that while Tom was my one and only jack-off buddy at the time, the same could not be said of him.

"We can do this the easy way, or the hard way," Don said. "Maybe you want to be forced into it. Would that make it alright in your mind? Let you feel like you really didn't want to do it, but I made you. Is that it?"

The robe came off, and I admit now that perhaps there was a part of me that wanted to show Don my body, but the setting wasn't like I wanted it to be. I stood naked, trembling and terrified as this guy I had known all of my life looked me over with a grin that made him seem like a wolf.

"You used to run around the house naked all the time when you were a little fella," Don said, his eyes fixated on my crotch. "I like the way you look now a whole lot better."

"Pull on it - like you were when I caught you looking at the book," Don said, and when I hesitated he offered me the book to look at for inspiration.

I shook my head and closed my eyes, wanting for this humiliation to be over. My hand went to my dick, and I began pulling on it in an effort to get hard. Despite the situation, I felt myself getting erect, and when I finally got hard I opened my eyes.

Don had taken his shirt off and was lifting the wife-beater he wore under it. His chest was scrawny but covered with salt and pepper hair, with faded tattoos underneath the curls.

"Nice," Don said. "Now get on the bed."

"What?"

"Get on the bed," Don growled. "On your hands and knees."

******

Chapter Five: Assuming the position.

I did as Don had ordered, and as I knelt in the position he wanted me in, I heard a thump along with the sound of a couple of coins rolling on the floor, and then came the rustling of clothes. I glanced back and saw that Don had taken off his pants and was pulling down his boxers.

"What are you doing?" I asked while watching him step out of his underwear, and when I saw his cock I thought I was seeing things.

Don was a tall and skinny guy, and his cock was built along the same lines. His dick was outrageously long, hanging halfway to his knees, and was incredibly skinny as well, looking a lot like the foot-longs they sold at the ballpark.

Don's cock swung back and forth as he walked slowly over to his night stand, the uncircumcised hose as limp as could be, and when he pulled a jar of Vaseline out of the drawer, I asked him again what he was doing.

"Gonna have some fun - you and me," Don said as he scooped out some of the jelly and began rubbing it all over his cock. "Damn, you look nice like that. Spread your legs a little more so I can see your nuts. Damn Paulie, you got the potatoes along with the meat there."

Don's greased hand was still rubbing his cock, but that cock was now hard and pointing straight out from his body. It hadn't gotten much longer or thicker, but it had been plenty impressive enough as it was before, and part of me was hoping that Don was going to make me jerk him off because I would have been more than happy to do it.

"Oh!" I moaned when I felt the cold gel rubbing my anus, and then I let out a real yelp when I felt Don's finger inside of me.

There wasn't any time to protest, or maybe I was just too stunned to do anything but try to move away from Don. Ironically, this was probably what Don wanted me to do anyway, since it gave him room to get on the bed behind me.

In seconds, I lost my virginity. I felt Don's long hard cock slide into me while he held my hips, and it kept sliding deeper and deeper into me until it felt like it was coming out my stomach.

"Oh, that's a tight ass," Don moaned as he began moving his long prong in and out slowly while his spider-like body covered me. "That's it. Take it all."

Don's right hand had reached around and grabbed my cock again, and while he pulled and stretched my dick his left hand was playing with my nipple and squeezing the little man-boob that formed when I leaned over like that. From time to time his hand would slip under my arm and play with the hair there before returning to tweaking my nipple.

Don's body was rubbing against my back as he thrust into me, his chest hair feeling crinkly against my bare back, and as he increased the tempo of his thrusting his breathing got heavier and louder in my ear.

It didn't hurt. That's what I remembered thinking as Don's cock impaled me hard and deep. It was probably because his cock was so slender, but not only wasn't I experiencing the pain that I thought would come with what was happening, it was actually beginning to feel good.

It did start to sting when Don's began to thrust into me with brisk jabs, but then I heard him let out a loud groan, and with that came the twitching of his dick deep in my rectum, followed by a warm soothing feeling as he filled my bowels with his seed.

"Damn, that was good," Don wheezed as he hugged me from behind, and I could feel his cock getting soft inside of me while he caught his breath.

I shivered when his dick slithered out of me, and then Don eased me onto my back while he knelt beside me. My cock was between soft and hard, but when Don's hand wrapped around it again it got hard almost instantly.

"You're sure no chip off the old block, Paul," Don said, holding my cock upright and admiring it while squeezing my balls with the other hand, and then he bent over and took my dick in his mouth.

What a feeling! I had only gotten head one time in my life, by Marcia Hall back in the woods one time when we got drunk, but that was nothing like this. Marcia's teeth had practically chewed me up that time, and I had walked away from that experience thinking that this blow job thing was way overrated.

My opinion changed when Don's head began to bob up and down, that weathered face of his intensely focused on my cock and his wet mouth enveloped almost all of it before sliding back up to the tip again.

It was so good - and too good really, because way too soon I felt my orgasm raced through my loins, and I didn't even think to warn Don that I was about to cum.

Don didn't even blink an eye, but kept on sucking my cock as it erupted in his mouth, his hand milking my balls roughly as I squirmed on the bed until he had drained me. Some of my cum had slid down from out of the corners of Don's mouth and was in my pubes, but he must have swallowed the rest, and as his mouth came off of my dick he seemed to like the taste.

"That was great, Uncle Don," I exclaimed, drawing a wink from my faux uncle.

"Did I do as good as your friend Tommy?" he asked.

"He never - we never did anything like that," I said.

While it was true that Tommy had kissed the head of my dick once and I suspected that he really wanted us to do that very thing to each other, he was probably afraid that I would think he was queer if he suggested it. That was pretty much the way I felt too.

"Are you kidding me? You mean to tell me you don't give each other head?" Don exclaimed, and when I shook my head he looked shocked. "You mean that was your first time taking it in the ass?"

"Oh," Don said when he saw me nod. "I mean, you were so tight that I figured that redhead didn't his cock in you, not with that fat one he's got, but I can't believe all you do is jerk each other off."

"How do you know all of that?" I asked, confused as to how Don would know what Tommy's stuff looked like and what we did.

"Let me show you something," Don said, motioning for me to follow him as he crawled off of the bed and over to the closet.

******

Chapter Six: Observed.

"Holy shit!" I exclaimed as I put my eye to the little glass circle and was treated to a bird's eye view of my bedroom.

"Hope you aren't mad," Don said. "I've always taken a fancy to you, Paul. When I saw your friend Tommy there I knew he was homosexual, so I did a little bit of drilling one day so I could keep an eye on you all of the time, and the two of you when he would visit."

"Tommy's not a," I started to say, but then I stopped and thought about it. Maybe he was. Hell, maybe I was.

"Whenever I'm over here and hear his voice, I hightail it in here and get ready for the show," Don said joyfully. "If I hear you lock the door, I know you two are going to be playing around. I was always hoping to see something more than hand jobs, but I figured you did other stuff someplace else."

"No, that's it," I said.

"He wants it," Don informed me. "I can tell just by the way he looks at you that he's dying for it. Take my word for it. If you want that chubby ass, you go for it. Just make sure I'm here to see it when you do."

"I don't know," I said, and that covered everything Don had said.

Being watched - how many times had Don been sitting in here watching me jerk off? I did it every day, for crying out loud. And those times with Tommy?

"It was all I could do to keep from inviting myself in with you two," Don confessed. "Seeing you two young bucks with your stiff cocks - especially you, Paul. What have you got? seven -eight inches maybe?"

"I dunno," I lied.

"And then that Tommy's got a beer can on him," Don detailed. "That's one fat little pecker he's got. That's why I figured him for a bottom. I'm going to go clean up. You got plans for the day?"

"Not really."

"If you don't mind hanging around your Uncle Don today, I've got a few ideas on how to pass the time."

******

Chapter Seven: Education.

Don was standing in front of me, that towering John Carradine-like beanpole physique looking more like 7'4" than his actual 6'4", and the fact that he was naked only served to make me more nervous.

I was sitting on the edge of the bed, my eyes fixed on what was directly before me, Don's genitals. From beneath a nest of salt and pepper pubic hair, Don's cock hung straight down, and even limp, I was astounded that not long ago thing had been very hard and had been drilled into my ass.

Don could talk all he wanted about how well hung he thought I was, but the plain and simple truth was that Don's cock was outrageously long. Not thick, mind you, and in fact it was just the opposite. No thicker than a thumb, the tan tube was richly veined at the base, and the outline of the head of his dick was clear under the long foreskin which shrouded it.

I had only seen one other uncut man before, one of the guys in my gym class, so this was something that took getting used to. My hand was visibly shaking when I reached out and took Don's cock in my hand, and when I felt how soft and rubbery it was it took me a second to get used to it.

Tommy's was the only other cock I had ever touched, and his was always hard, or so it seemed, so holding Don's wiggly dick felt weird at first. Don chuckled when he saw how tentative I was but he stood there patiently with his hands on his hips waiting for me to do something.

timmywells
timmywells
1,749 Followers