Late Night Lesson Long Ago

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Family friend teaches 18-year-old a special lesson.
3.4k words
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Part 1 of the 4 part series

Updated 12/14/2023
Created 09/01/2023
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Back in my senior year in high school, I worked at a grocery store about a mile from home in suburban Chicago.

Being the "good Catholic kid," the boss knew she could rely on me to work odd hours. One Saturday, I had the dreaded 7 p.m. to midnight shift. eh, i was not complaining. Time usually flew.

But there was a problem. I didn't have a car and my folks were visiting family out of town overnight.

"No problem," I said. "I can walk home." Dad was having none of that.

"Sorry, Gary, but it's not safe walking home that late along a busy road with drunken drivers on a Saturday night. I will find you a ride," Dad said.

"I'm not a little kid. I'm 18," I protested. Well, you know how far that went.

On Friday during dinner, Dad said he had a solution.

"You know Al lives a few blocks from the store. I talked with him and he offered you a ride home," he said.

Al was one of Dad's oldest friends. We hung out with Al and his family now and then. Heck, they nearly were family. I smiled, said "that's cool" and agreed to the ride.

I always liked Al. He was in his mid 40s, tall, dark hair, always smiling or cracking jokes. An easy-going guy.

When my folks were leaving Saturday morning, they reminded me "to thank Al for his generosity." I assured them that I would and wished them safe travels downstate. The rest of my day was filled with chores and homework.

It was light out at 6:30 p.m. in May, so i walked to the grocery store. On the way, I thought it is smart to get that ride, and i looked forward to seeing our family friend.

As expected, the night flew with busy moms buying groceries for their families, people stopping in for forgotten items, and the usual party people buying beer, wine, booze and munchies. I twice had to turn down underage kids trying to buy. Hey, I've done the same.

Before I knew it, it was close to closing time.

I counted money in my drawer, chatted with the boss, then went out to catch ny ride. I knew Al's car. He flashed his headlights and I walked towards it after a busy night of work.

i opened the door, greeted me with his typical smile. Much to my surprise, saw five or six girlie magazines on the passenger seat. I made light of it, saying "interesting reading material" as he scooped them off the seat and tossed them on the backseat. He apologized about the magazines.

"No apology needed," I said. "After all, don't most guys look at those magazines?"

He said he "borrowed them from a friend. Hope you don't mind."

I assured him it was fine and I've seen a few.

"Oh, really?" he asked, a smile on his face. "Do you want to borrow a few?"

Being a horny 18-year-old, i jumped at the chance. "Sure, can I borrow two or three?"

Al smiled and said "just don't tell your folks who gave them to you." We both laughed and I assured him his secret was safe with me.

We soon arrived at my house, and he handed three mags. "I promised your folks I would get you home safely. Do you mind if I come in to make sure nobody is inside?"

I said I'd appreciate it and unlocked the door. Once inside, Al did a swift safety check. As he did, i noticed he looked good "for an older guy" in his T-shirt and jeans. No beer belly. Strong chest and arms. No sagging rear like many his age.

Not sure why I noticed, but that thought vanished when he said "all good, guess I will head home."

"Hot date?" i asked.

"No, no," he said, "my wife is sleeping and it is 12:30. Figured you are tired."

I said I wanted to be a good host and offered him a beer.

"Dad lets me drink beer at home." He smiled and agreed.

We sat at the kitchen table, popped open two beers. We had some small talk about school, summer plans, girls, baseball, the usual.

The magazines were on the table.

He asked, "well, aren't you going to take a peek?"

"They do look interesting," I said. "Sure, why not?"

I grabbed one and began flipping the pages, admiring photos of a lovely brunette. A few pages later featured two blonde women licking each other. Al sat sipping his beer, watching me as i looked at the magazines. I felt my cock stir in my jeans, hoping he did not notice.

"Nice, eh? Do you like those?" he asked.

I nodded, my eyes glued to the pages.

He smiled and said, "happy to share them with you."I took a sip of beer, nodded, and said glad you did.

He then grabbed one of mags and said "you may like this one."

The cover had a man and woman nearly naked. i opened it and found photos of the couple inside. The first few, she was naked. Then he was. His erect cock was huge.

Having never seen this before, I soon was fully erect myself, with a bulge in my jeans as my eyes enjoyed the view.

"Someone likes what he sees," Al said.

I looked up to see him staring at my bulge with a smile on his face. i quickly tried to cover myself with a mag. Too late.

"I'm sorry, Al, I didn't mean to..." I stammered.

Al stared into my eyes, and replied, "Gary, any guy would respond that way. It is perfectly normal. See?" he glanced down. I followed his gaze down to his own large bulge in his jeans.

"You're hard, too? Why?" I asked.

Al smiled and said "seeing you get hard turned me on.... You do like that man's cock, don't you?" I slowly nodded.

My mind wandered to earlier, when I noticed how well built he was. I caught myself wondering how built he may be elsewhere. I must admit, the thought of bi sex had crossed my mind now and then when jerking off.

It's like he read my mind.

"So... do you want to see something else?" he asked.

I nodded slowly again. Wondering. He stood up, unbuckled his belt, lowered the zipper and pulled down his jeans. His hard cock strained at his briefs.

"Wow," I whispered. "I've never seen one in person before. About seven inches?"

"Closer to eight," he said, pulling down his briefs.

Al sat down. His cock pointed up to the ceiling. I could not stop staring at it, the thick shaft, the purple mushroom head.

"Take a picture, it'll last longer," Al said and laughed.

Al's joke broke the tension, and put me at ease. I laughed.

"So, fair's fair," he said. "Now it is your turn."

"What do you mean?" I replied.

"Gary, we have the same plumbing. It is no big deal. Let me see what you're packing. You see mine," Al said.

Standing up, I undid my belt, unzipped and pulled my jeans down.

"I took my briefs off. You, too," he said. "It's just us here."

I did as told and my seven inches sprang out.

Al murmured "mmm very nice" as he gazed at me.

I then saw something different in his eyes, a blend of want, lust and pure sexual desire.

Without a word, he reached up. Thumb on the underside, pointer finger on top, he began tracing my hard seven inches.

"Al, I'm not sure you should..." I trailed off.

"Why not?: he asked. "It's our secret, like the magazines. Besides, really, Gary, doesn't this feel good?"

As the waves of pleasure began to flow through me, I had to admit it did. Then I whispered, "please don't stop."

. I admitted "yes, it does" adding "please don't stop."

Al smiled, knowing he had me right where he wanted me.

Wrapping his large hand around me, he began to stroke me gently. I was surprised a construction worker's hand felt smooth as silk on me. I watched closely as his hand caressed my 18-year-old cock.

"Oh, man, that does feel good," I moaned.

"I know it does," Al said. "Please, sit before you fall over."

As if in a trance, I sat. His hand resumed pleasing my hard cock, slowly stroking back and forth.

"This will feel good too" he said as he leaned closer to kiss me.

I had kissed girls before, but this was different.

This was a man. And a family friend. It felt wrong but right. I was surprised that his lips were so soft, Then, i felt his tongue trying to pry my lips open. I relented.

Our tongues met, tentatively at first, then soon wrestling with passion and desire. We French kissed a few minutes as he stroked me. What a combination of pleasure.

Then he pulled away, smiled, fell to his knees and without a word and began licking my cock from the base to the tip, lingering at the head, then repeating that motion again and again.

"Oh my God, that's fantastic," I moaned as he expertly licked my cock. Clearly, Al knew how to pleasure a man.

As i sat there enjoying his mouth, I thought to a week earlier when he and his wife were our dinner guests at the same table. Now he was eating again, with me on the menu.

"Mmm, that feels great," I moaned.

"Mmm hmm," he said, his mouth filled with my hard, throbbing seven inches.

Then he began focusing on the head, slowly going back on forth on it, his lips teasing the foreskin each time.

His tongue found my cum hole, slowly licking it. Oh, he knew what to do, how to bring me to the edge of coming, then backing off to make it last longer.

His tongue was like velvet, swirling around the head of my cock, sending pleasure through my entire body. I was all his and he knew it. He took his time, licking up and down, teasing the cum hole, bringing me to the edge, pausing, repeating. It was amazing.

He did this time and time again. as his hand caressed my balls. I soon began to feel that familiar feeling, the cum building in my balls. I knew I'd cum soon. I cautioned him with "Al, I'm gonna cum."

He murmured "mmm" and his lips sealed even tighter around my cock, Then and there, I knew he wanted my jizz.

I felt my cum inching up, until i was ready to shoot.

"Oh, take it, Al. It's all for you," I cried out and I began to spurt in his mouth.

"Mmm, hmmm" he moaned as he eagerly swallowed every shot.

I came so hard, so much. Like never before in my jerk-off sessions. He took to it like a bear to honey, savoring every drop and gulping it down.

After I came, he kept my cock his mouth, licking it slowly, carefully cleaning it, sure to not miss any jizz. My cock slowly softened, he pulled his mouth off, rose and kissed me, I tasted my own cum in his kiss,

"Well, how did you like your first blowjob?" he asked.

I smiled and said "I loved it."

He then said, "it's a night of firsts, Gary."

Standing up, his erect eight inches were even with my mouth, He glanced down and said, "your turn."

I was so turned on. had to return the favor.

"Al, I don't know what to do" I said.

"Just do what I did, what you know feels good. Nature takes over," he said.

He was right. I always wondered what it would be like to please a man. I began stroking him, slowly, as he did me. Then I leaned forward and ran my tongue around the head. I was surprised at how warm and velvety smooth it was. I was more turned on.

"That's it, Gary, you are a good student," he whispered.

Encouraged by his words, I took his head into my mouth and mimicked what he did, moving my mouth back and forth on him so my lips rubbed agains this foreskin each time. My tongue found his cum hole and i licked him slowly there.

"Mmm, just like that, baby. Perfect," he gasped.

I could tell he was enjoying by rookie blowjob by his moans of pleasure. Those moans turned me on, made me want to please him even more.

So, I began stroking his cock with one hand, rubbing his balls with the other as I sucked.

"Oh, a natural," he murmured, "I always thought you would be. I've wanted you for a year."

Hearing that intrigued me.

"A year?" I thought.

I tried to take him deeper, but I could not get more than two or three inches in.

He didn't seem to mind as I could feel him getting harder in my mouth. Even being a first-timer, I knew what that meant.

I tried to do what he did to me. Licking slowly, circling his cock head, teasing the foreskin, lingering over that cum hole.

"Mmm, Gary, I'm going to cum soon if you keep doing that," Al said.

"Mmm hmm" i murmured, wanting to please my late-night house guest as he pleased me.

He reached down, his hands in my long hair - this was in the 1970s - and began fucking my mouth slowly as i sat on that kitchen chair. Then, with more intensity.

"You want it, don't you?" he said.

"Mmmm hmmm" I moaned on his hardness.

"Fuck I'm, close," he moaned "Close, close..."

Then with a mighty groan, he thrust deep into my mouth and began spurting.

The first spurt of cum surprised me. It was salty and sweet at the same time. But I was so turned on, I began gulping it down. I tried to get all I could, knowing it pleased him. It pleased me, too, knowing I was making him feel so good.

"Suck it, suck it, cum slut," he yelled.

Some did leak out of the corner of my mouth, which he later said was very sexy to see. i kept him in my mouth until he was drained. Just as he did to me.

Finally, he softened and slowly pulled out. He smiled down at me.

"Well," he said, "how did you like that?" I smiled up at him.

"Loved it," I said.

He leaned down for a kiss. Saving some cum for him, i let it ooze into his mouth. He loved that.

"Your folks are gone all night,. We need some rest," he said.

"What about your wife?" I asked. "Won't she wonder where you are?"

"Nah," he said, "I told her I'd out playing cards after giving you a lift and that I'd be spending the night at my friend's house,"

My bedroom was near the kitchen. Naked, we left our clothes on the floor and walked into the room and climbed into bed.

Laying on our backs, we were tired from our endeavors. That's when I asked him, "so how long have you planned this?"

He said, "since last summer."

"When your family came over for that Labor Day pool party. You looked so sexy in that tight red Speedo. I've been jerking off to thoughts of you ever since," he admitted.

"So, when your dad asked if could help out tonight, I figured that was my chance," Al said..

"You had a very good chance," I said.

"I saw how you stared at me when I got out of the pool to get a Coke. There was something in your eyes. When I got home that night, I jerked off to the thought of you sucking me," I said. "What it would be like to suck you off? I've had that idea more than once."

"Ah, so great minds do think alike," he said. We laughed.

"How were you so sure you'd succeed?" I asked, my hand resting on his belly.

"I was 18 when a neighbor changed my life. I used to cut his grass. Then one day, he hit on me. I resisted but he was very focused. He was 60 and he knew how to suck a cock. He gave me some very sexy lessons that summer," Al said, his arm around me, pulling me close.

"Well, I'm glad he did," I said.

"When you're 18, you have amazing abilities," he said, reaching down to play with me.

He was right. I soon found myself throbbing. Reaching down, I found he was half hard already. So i began stroking him.

"Mmm, you are fast learner," he said.

We were both sporting nice hard cocks in about five minutes. Our fingers playing over each other's heads. That's when Al said "rub my chest."

I did, marveling at his muscular build. Construction is a good workout, I thought. I tweaked his nipples, getting them hard.

"Mmm, Gary, that is so hot," he moaned. "What's you favorite number?"

"I don't know. Seven or eight, I guess," I said, thinking of our cocks.

He laughed, "The correct number is 69," Al said.

With that, he swung around swiftly, to get his face near my cock and get his cock pointing to my lips.

There was a small light on in my bedroom. I could see he was more than ready.

So I started by licking around the head, hoping he'd do the same. Sure enough, he did. His skilled mouth, which had been sucking cocks a good 30 years or so, soon found mine.

There we were, naked on my queen-sized bed, feeding each other our cocks in a hot 69. I briefly thought "what would his wife say" and "what would my folks say," but those thoughts were soon replaced with pleasure as he took me deeper into his mouth.

I tried, but again only managed a couple inches. I felt him take all my seven in, his nose to my pubes, then he'd pull it out to the tip. licking feverishly.

"You'll like this," he said, wetting a finger in his mouth, reaching around and finding my virgin asshole.

"Mmmmm" I moaned when his finger did little circles around my tight hole, then sliding in a bit, wiggling his finger.

That drove me crazy with desire and i sucked harder on his cock.

There we were, teacher and student, in my bed. Our family friend with his lips and tongue all over my cock. And I did the same to him, licking from base to tip, lingering on the spongy head, taking the whole head into my mouth.

Once again, thanks to his wonderful cock sucking skills, I felt my cum inching up from my balls. No need to warn him, I thought, knowing how he lapped up every drop of my cum last time.

Again, I felt his nearly nearly 50-year-old cock get harder, telling me he was ready to cum soon, too. I came first, shooting into my new lover's mouth as he moaned his appreciation.

This time, I pursed my lips around his cum hole, so when he started spurting, the jizz squirted through my lips into my greedy mouth. It was so sexy.

I was ready this time and welcomed his load, eagerly gulping it down as i was so hungry for him.

The room filled with our moans of pleasure, as we serviced one another. Just like the first time, he slowly licked me clean afterwards. I did the same to him.

We were both exhausted after as he swung around to have his face near mine. We enjoyed a cum-flavored kiss or two, our tongues slowly dancing.

"So, did you like my finger?" he asked.

"Mmm, yes, I did. Was that a lesson taught by your neighbor after he mowed the lawn," I asked.

Al laughed.

"Well, that was one of the many lessons I learned that summer.... I hope to teach you a few more lessons, provided you are interested, during this summer," Al said.

I laughed and said, "let's see, after tonight? Of course, I am interested."

We kissed again.

As I lay in bed beside our family friend who now was much much more, his muscular arm around me, I smiled knowing that I did indeed "thank Al for his generosity," just as my folks had requested.

I could tell my his breathing that he was fast asleep after our wild night.

Then I drifted off to sleep wondering what other lessons Al had planned for me.

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HubLongtimeHubLongtimeabout 1 month agoAuthor

I’m glad readers are enjoying this!

open2funwuopen2funwuabout 1 month ago

Very hot story...this one made me cum...

Lars420Lars4206 months ago

Wow...super hot story. Can't wait to read about his next class assignment.

LarryInSeattleLarryInSeattle7 months ago

Damn I love first time stories! And you did a great job with this one. The age difference sure added to it as well. I stroked all the way through and had to really try hard not to cum withe y'all's first cum..I lasted until the second one, just barely. Thanks!

OntarioBob61OntarioBob618 months ago

Good start--nicely left open for more chapters--Just how far will Gary and Al go?--

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