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                 K R I S T E N' S    C O L L E C T I O N
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Jack Off Lessons 
By Peter Handler (peter_handler@hotmail.com)

***

This is a story about brothers coming of age with a 
little help from their aunt and uncle. (MF/mm-teens, 
ped, exh, mast, 1st)

***

My brother Jack and I were around thirteen when we 
spent the summer at the country home of our Aunt Millie 
and Uncle Roy. Our parents were hard-working, no-
nonsense people who had neither the time, money nor 
inclination for fun things, but Millie and Roy were 
just the opposite. They had money and they liked to 
spend it on good times. 

Aunt Millie was a shapely woman who drew admiring 
glances wherever she went. I had a difficult time 
hiding my hard-ons when she was around. One whiff of 
her perfume or a glance down her cleavage was all it 
took to give me a raging boner. Roy was also good-
looking. Everyone said they were the perfect couple. We 
were always going someplace, to the movies, the zoo, 
the park, or a ball game. My brother and I had the time 
of our lives. 

We had gone through puberty but hadn't yet learned how 
to masturbate. The result was that we shot off in our 
dreams leaving nasty cum-stains on Aunt Millie's 
sheets. We did our best to clean up the messes, but if 
you have ever tried to clean up after a wet dream, you 
know that it is just about impossible. Naturally, Aunt 
Millie noticed the stains when she did the laundry. 

One day when Roy took us fishing, he brought up the 
subject of masturbation. 
"Millie tells me you boys are messing your sheets," he 
said, very casually. "I'm sorry, Uncle Roy, I just 
can't help it," we both blurted. "Oh, I know you can't 
help it," he said. "It's natural to have wet dreams. 
But there's a better way that doesn't make a mess and 
is a lot more fun. It's called masturbation." 

"If you play with your dick just right, you can make 
that stuff shoot out into the toilet or the sink or 
wherever you want to put it," he continued. "Don't you 
boys know how to do it?" Blushing furiously, we shook 
our heads no. "Well, I will just have to teach you, 
then. But your Aunt Millie has to be there just to make 
sure that there is no hanky-panky." I didn't know what 
he meant by that but was heartened to hear that 
beautiful Aunt Millie would somehow be involved. 

At the dinner table that night, Roy said to Millie, 
"I'm going to teach them tonight." They had apparently 
discussed it ahead of time. "Good," Millie answered. 
"You boys are in for some fun," she said with a wink. 
Later that evening, Aunt Millie called to us in our 
room and said that they were ready to start. The first 
thing I noticed when I entered the livingroom was that 
the draperies had been tightly drawn. I had never seen 
them closed before. 

Uncle Roy had us sit on the couch then he stood in 
front of us and began to undress. Aunt Millie sat to 
the side, watching with a smile on her face. Roy pulled 
off his Jockey shorts to reveal a huge cock and a 
matching set of furry balls. His cock was half-hard, 
but as he slapped it around and pulled on it, it 
stiffened until it was as hard as a club. It got so 
hard that it curved upward to point at the ceiling. 
Everything seems big when you are little, so maybe 
Roy's cock isn't as big as I remember it. It certainly 
impressed me at the time, though. 

Roy demonstrated the basics of masturbating, showed us 
his favorite strokes, and explained how to enhance the 
pleasure with lubricant. "My favorite is Vaseline," he 
said, as he scooped a big gob out of a jar and rubbed 
it on his dick. "It isn't as slick as hand lotion but 
it doesn't dry out as fast." I figured they would send 
us to our room to practice what we had learned, so was 
shocked speechless when Millie said, "Okay, boys, get 
those duds off and get started." 

Our faces were the color of ripe tomatoes as we 
reluctantly removed our clothes. I didn't want Millie 
to see my little dick. Her husband's was twice the size 
of mine, maybe more. If only it had been hard it 
wouldn't have been so bad, but sheer anxiety had 
prevented any arousal. Jack was in the same state. Roy 
handed us the Vaseline and told us to follow his 
example. We tried to copy his techniques, but our cocks 
just weren't hard enough. 

"Try playing with each other," Millie said. "That might 
work. And don't worry - it's perfectly natural for boys 
to experiment with other boys and no one will ever 
know." I reached over and began toying with Jack's 
little dick. He slumped back on the couch and closed 
his eyes. I could tell he loved it. His cock started to 
stiffen on the first touch, and within a few minutes 
was hard as a pickle. "Attaboy!" Millie said. "Now, 
Jack, it's your turn." 

When Jack reached for my cock everyone laughed to see 
that it was already hard. Playing with Jack's cock had 
been enough to get me aroused. "Tease it a little for 
good measure," Millie said. Jack's hand stroking my 
cock felt wonderful. The whole scene was really turning 
me on. Having beautiful Millie there watching and 
encouraging us was almost too much to bear. "Okay, do 
it to yourselves, now," she said. 

Jack and I were then able to duplicate most of Roy's 
techniques. He showed us some that were more suited to 
the size of our cocks, like using the fingertips 
instead of the fist. "I think it's time for the last 
lesson, don't you?" Roy said to Millie. "Yes, I think 
so. Go ahead, dear." Roy motioned us to our feet and 
stretched out on the couch. "If you boys think it feels 
good to come in your sleep, just wait until you see how 
good it feels when you are awake," he said. 

Roy began to pump his big cock with his fist. After a 
minute or two, he said, "Here it comes, watch closely." 
His jism spewed out in thick spurts all over his hairy 
chest and belly. Millie applauded the display of her 
husband's virility. The spurts finally stopped and Roy 
went limp. "Damn, that was a good one," he boasted. 
"Yes, it was, dear," Millie said. She gave us a few 
minutes to examine the mess all over Roy's torso, then 
carefully dried him with a towel. 

Roy changed seats and told us to go back to our places 
on the couch. "Okay, boys, it's your turn," Millie 
said. "We have to make sure you know how to pleasure 
yourselves." Jack and I started beating off. All the 
time I was at it, I visualized myself doing nasty 
things to Millie, things like putting my little dick in 
her mouth or between her big tits. I had no idea what a 
pussy looked like, so couldn't really visualize fucking 
her. 

Jack and I went off practically together, and Roy had 
been right - it felt wonderful! Roy's ejaculation had 
consisted of many watery spurts, but our dicks spit out 
only a few creamy gobs of cum. Roy explained that as we 
got older, our ejaculations would become more like his. 

"Good night, boys," Millie said, kissing us each on the 
forehead. "I hope you enjoy your new toys every day." 
Up in our room, Jack and I listened through the thin 
bedroom wall as Roy fucked the daylights out of Millie. 
Before long, Jack and I had crossed arms and were 
jacking each other off. Roy and Millie went at it for a 
long time. In between the fucking, which was obvious by 
the creaking springs, there were long pauses filled 
with wet sounds and soft moans. 

We were very naïve, but we knew enough to know they 
were going down on each other. 

"They looked so cute jerking on their little peters," 
Millie said. "Yeah, and I bet they were thinking about 
fucking you while they were at it," Roy replied. Jack 
began jerking hard on my cock, then I felt his cock 
spasm as it went off. A few seconds later I blew my 
wad. 

After that, we were free to jerk off, or jerk each 
other off, whenever we felt like it. We didn't have to 
worry about getting caught. In fact, I found it 
thrilling to get caught, especially by Millie. When she 
walked into our room thinking it was empty and caught 
me wanking on my bed, she just laughed and said, "Don't 
worry, honey, you can't wear it out." 

One day Roy, Jack and I were in an isolated spot 
fishing. We weren't getting many bites and were 
somewhat bored. Roy livened things up when he said he 
would teach us something. He pulled his big cock out 
and starting jacking it. In short order, his watery 
spunk splashed onto the still water. We laughed as 
small fish gobbled up the spunk as it floated on the 
water. "Go ahead, you two," Roy said. Jack and I pulled 
out our dicks and soon sent our loads onto the water. 
The little fish went into a feeding frenzy over our 
spunk. A short time later, we began hauling in fish. 
Apparently, the little fish gobbling up our cum 
attracted the larger fish. That night as we enjoyed a 
fine fish dinner, Roy told Millie exactly how we had 
caught the fish. She got a good laugh out of it. 

Toward the end of the summer, Roy and Millie said they 
were going to teach us the facts of life. "If I know 
your Mom and Dad, you won't learn anything from them," 
Millie said scornfully. That night, Roy led us to the 
master bedroom, where Millie lay sprawled on the bed 
without a stitch on. Jack and I stared wide-eyed at the 
most beautiful creature we had ever seen. "I'm going to 
teach you about sex the same way I taught you how to 
jack off - by showing you," Roy said. 

He stripped down and went to the bed to tenderly fondle 
his beautiful wife. "If you boys want to strip and play 
with yourselves while you watch, it's okay with us," 
Millie said. "In fact, I think it would be for the 
best." We were bare-assed in seconds. Roy started off 
by giving us an anatomy lesson. He pointed out the 
parts of Millie's pussy and told us what they were 
called, both in medical terminology and in slang. 

After we had learned all about Millie's pussy, Roy 
showed us several ways to prepare a woman for a 
fucking. He used his fingers first to masturbate her, 
and then he went down on her. How I envied him! She was 
soon breathing heavily. Then Roy lay back and said to 
her, "Your turn." Seeing Millie with that thick cock in 
her mouth was the most thrilling thing that had 
happened to me in my young life. "This is how the woman 
gets the man ready," Roy said. "If he comes in her 
mouth it's called a blow job." 

Roy mounted Millie and fucked her, keeping his legs 
apart so we could see how his cock went into her. 
"There are a lot of different ways to fuck," he said, 
as he pulled her up onto all fours and fucked her 
doggy-style. After demonstrating half a dozen 
positions, Roy said, "Watch carefully now, she's 
starting to come." Millie's beautiful face was 
contorted with lust. She tossed her head from side-to-
side, then buried her face in a pillow and screamed 
into it. "Don't worry, boys, it may sound like she's 
hurting but it's just the opposite," Roy said as he 
pumped her hard. 

Jack and I were next to the bed, sometimes changing 
positions to get a better view, and constantly frigging 
our cocks. They ended up with Millie on her back, her 
ankles clamped in Roy's hands. He was squatting with 
his thighs on either side of her ass, pistoning his 
cock in and out of her. Sweat broke out on his forehead 
and his chest began to heave. "Boys, I'm going to 
finish now," he said. "If you want to try to come, too, 
go right ahead." 

Jack and I began pumping our dicks hard. Millie had her 
eyes wide open, watching what we were doing. Roy 
suddenly pulled his dick out and began to jerk it. His 
load spewed all over his wife's beautiful body, soiling 
her tits and belly. Some even shot all the way to her 
face. That was too much for me and I shot my load onto 
the sheets. Jack went off, too. 

"You boys were good students," Aunt Millie said. She 
and her satiated husband laid back and sighed with 
contentment. When I looked down and saw my load soaking 
into the sheets, I remembered how it had all started. 

END

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The author does not condone child abuse, this story is
meant as an erotic fantasy not real life. Anyone acting
out such scenarios in "real life" can look forward to
many unproductive years getting it up the butt by a 
fellow convict in their local prison.
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Kristen's collection - Directory 54