Life is Unfair: New September 19

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Re: Life is Unfair: New September 11

Post by NudeBaG »

TeenFan wrote: Fri Sep 11, 2026 4:09 pm
NudeBaG wrote: Fri Sep 11, 2026 3:37 pm So this is still Joseph telling a story?
Josef begins to tell this story to the group, then we jump back in time to when the event took place.
Josef won't be giving every little detail to his "Friends" when he tells the truth about the day he got caught
jerking off. He will assume nobody knows anything about this, and will try to skip over much of it...until Tabitha
proves she already knows more than Josef suspected.
I think I get it.
Tabitha is still my current favorite character out of this story

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Re: Life is Unfair: New September 11

Post by TeenFan »

Life is Unfair
Chapter 40. Truth be Told, part four: It's Only Natural


Josef was telling the story about the day he got caught jerking off. This particular Truth was requested by Tabitha.

"I was stroking myself, my eyes were closed. I was imagining something hot, something inspired by the magazine. I didn't know
Mrs. Torres was back in the room until she spoke up. I froze as she looked at me, and she came over to take the magazine away.
Then she sent me into the attached bathroom to clean it up as part of my duties. That was when Tabitha came home and- -"

"That isn't how it went down," Tabitha butted in. "My mom told me something about it. You have to tell everything or this doesn't count and
I get to pick a dare to give you."

Josef was momentarily stunned into silence. Tabitha had asked the question, "Did you ever get caught jerking off?", and Josef was answering
the question, mostly answering the question fully. It turns out Tabitha is like a good lawyer in the courtroom, a lawyer asks questions that
he already knows the answers to. Then if the person on the stand says something different, the lawyer can pounce and score points for
his side.

These were the key words: "My mom told me something about it". What exactly did the mom tell the daughter? How much detail did
she reveal to a daughter not yet old enough to handle the truth?

Josef sighed, as he was now forced to reveal the parts of this story he was intending to leave out...

* * * * *

"What are you doing?"

The words made Josef's eyes flutter open. What is he doing? He's jerking off after looking at a magazine called SLUT. What is he doing?
Well, it should be obvious. Mrs. Torres can see immediately what he is doing. One hand on an open magazine, one hand wrapped around an
erection...what more needs to be seen?

"I uhh...I found these under the bed. You told me to move the stuff out from under the bed."

"Did I tell you to pleasure yourself while looking at that disgusting stuff? I've complained for years to get my husband to get rid of this
shit, and now I find you looking at it. I am so disappointed in you young man. Stand up now. Stand up and hand that magazine over to me."

Josef stands up, his erection standing up pointing right at Mrs. Torres. He hands the magazine over, and stands with hands at his sides.
He wants to cover up, but this woman has been looking at him and his hardons for some time now, and he can't really cover up when that
thing is fully stretched out and throbbing.

Mrs. Torres looks at the magazine page, "Oh, that's a nice one. The naughty nurse. That is one slutty bitch of a way to get doctored up
I should say. You really want a nurse to do this to you?"

Josef looks down at his dick, as it jerked and twitched. "I uh, I guess that is obvious, ma'am."

"And doing that while sitting on my bed. What were you going to do if you got to the point of no return? Were you gonna just shoot off
onto the bedspread, or maybe onto the rug?"

Josef only shrugs his shoulders, his face turning red.

"I should tell your mom you've been a bad boy."

Josef looks up, "Oh no, please don't do that. Her punishments are the worst."

"What you were doing just now is...it is..." Mrs. Torres can't find the words for it.

Josef knows how to finish the sentence, "It's only natural."

Mrs. Torres puts her hands on her hips. "Only natural you say? Really?"

Backed into a corner, Josef defends himself strongly, a rare event. "Boys my age can't help themselves. I get aroused by everything.
I pop boners all the time and it sucks. I take my clothes off in front of someone, anyone...everyone, and I pop a boner. You have your
hands on me when I had to clean the ceiling fan so I got stiff. I find these magazines under the bed. They make me get stiff. I'm going
to explode if I don't do something about it. It's only natural. I wasn't doing anything wrong."

Mrs. Torres seems impressed by the argument, but she is still in charge. "The when and the where of you masturbating...now that is
wrong. I can have you punished severely for that. However, you are right. It is only natural that your urges and hormones are raging
out of control. You are growing up, growing bigger right before our eyes, and it is a wonderful sight to see. And since it is normal and
natural for you to be doing that I won't take offense. You may continue what you were doing."

Josef's jaw dropped nearly to the floor. Did he hear that correctly? "Ma'am...you want me to continue cleaning the room?"

"I want you to continue with your masturbation."

Josef has to clear his throat before getting any other words out, "Right here? You were complaining about where I was sitting- -"

Mrs. Torres reaches out a hand, and she gently takes hold of Josef's right hand. She pulls and guides Josef into the small bathroom
attached to the master bedroom. Her demeanor has softened, become motherly like a concerned parent helping a sick child get to
the bathroom. She positions Josef in front of the sink. Looking into the mirror the woman looks Josef directly in the eyes.

"You may continue jerking off here. I do believe this is a much better place."

Josef can see the logic of the location. The bathroom, the sink is a much better place to jerk off than on the bed of Mrs. Torres.
However, what is the logic of her standing there watching?

"Um, I need some privacy for this."

"Privacy for something that isn't wrong? You aren't doing anything wrong, so there is no reason to hide it. We'll make a deal. If you
jerk off behind closed doors you are admitting it is wrong. If it is wrong I must inform your parents you are misbehaving. But if you
allow me to watch, then that proves you haven't broken any rules. It proves you are NOT ashamed of this. We'll get through this
together and go about our business. Well, how do you want to do this?"

It was a lot to process, so it took Josef a minute or so of thinking. If he jerked off with Mrs. Torres watching, then all is well and good.
If he told her to leave, then she will let mother know what happened. It's two bad choices for fuckin' sure.

Looking at himself in the mirror, Josef can see a slender boy with an angry red cock that needs to be stoked so bad it may cause him to
have a stroke if he doesn't do something soon. His balls are beginning to feel full with a dull ache. Josef takes hold of the penis. It's already
extremely stiff and sensitive so no tugging and soft manipulations are needed. He goes straight to fast action stroking.

Josef puts eyes on himself jerking himself in the mirror, then the eyes glance over to the face of Mrs. Torres standing next to him.
That woman is keenly interested. She sometimes looks down at the action next to her. Sometimes she watches from the reflection of
the mirror.

A phone rings. Mrs. Torres pulls out the phone to answer. "Yes Tabitha, he is still here. We are in the master bedroom. He was cleaning
up the old junk under the bed. If you hurry you can catch him." The call is disconnected. "Tabitha will be here in a couple minutes. You
don't have much time till she comes in to join us."

OH SHIT...Tabitha is coming home. Josef doubles his efforts. He squeezes harder than he normally does, stokes at a faster pace.
This can't be happening. Tabitha can't show up to see this. It is horrible, but somehow the thought is arousing, the image of that
girl walking in to see him madly masturbating under her mother's supervision. What would she think? What would she say?

"Ahhh Ahhhh..." Josef can feel it coming. He doesn't' want to blast off onto the mirror, so he pushes down on it, angles it down into the
basin of the sink. "OHHH UNNNHHH"...White cum explodes to splatter the white porcelain of the sink. Several strong squirts hit between
the bottom drain and the upper level of the basin. Josef's knees nearly buckle the orgasmic punch was so intense. He puts a hand on
the sink to hold himself steady.

Mrs. Torres watches with a quirky smile on her face, a most satisfied expression. Josef looks at his dick as the final drops of gunk ooze
out in a long line that nearly stretches to the bottom of the sink basin.

Josef gets a couple pats on the rear end, "That was nicely done, Josef. But this bathroom needs cleaning. I'll be back in the kitchen
getting dinner ready." Mrs. Torres leaves the bathroom.

Josef turns on the faucet. He uses his hands to spray the water in all directions in the basin, wiping the slimy stuff off the porcelain
with his bare hands. There isn't time to use proper cleaning towels or cleansers. He can hear the sound of young girly talk saying hello
to the mother, then the sound of footsteps as the girl practically runs through the master bedroom to the door of the bathroom.

"Oh hi," Tabitha says with a happy sounding voice. "Oh wow. You don't have any clothes on, ha ha. What's is wrong with you? You look
like you have a fever. Your dick is so red. You must be allergic to work or something. You gotta tell me all about it. Why are you naked
anyways?"
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Re: Life is Unfair: New September 13

Post by NudeBaG »

Was SO hoping Tabitha would be there for that orgasm 😓
Damn it
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Re: Life is Unfair: New September 13

Post by Themarble »

Was waiting for Tabitha to somehow still make it in but considering she doesn't see Josef shooting until present day, I knew it was not gonna happen. But the idea it could've in that setting was amazing! I can't wait to see how present day progresses!
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Re: Life is Unfair: New September 13

Post by TeenFan »

We are getting so close to the Present Day, the day Josef woke up in bed to find an audience.
This event happened when Josef is fifteen.

His 15th birthday will be a big event to come soon. What will the birthday boy have to do?
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Re: Life is Unfair: New September 13

Post by TeenFan »

Life is Unfair
Chapter 41. It's True It's True


"Dang it. I wish I was there to see that," Tony says. "I got home later than Tabitha and by that time Josef was wearing the tiny red
underwear. Did my mom really watch you jerk off into the sink? Total wow."

"I guess you guys know why I don't go over to your house much lately, not like my brother does. I'm always afraid your mom will
expect me to um...to take care of business whenever I get hard down there."

"Which is all the time you know," Karl jumps into the conversation. "Sometimes I wonder if my brother is taking Viagra. Every time I see
him with no clothes on or in his underwear he seems to have a hardon."

Tabitha redirects the conversation, "You are the last one to ask a question. Karl knows Josef better than anyone. I'm sure there is something
good for us to find out."

"Yeah, I know something funny good about Josef and me going to summer camp. Tell them what happened the day we did the Indian
adventures at the camp."

"You really want me to talk about that? No way."

"You tell or I will. They find out what happened to you anyway, and I give you a dare for refusing to tell the Truth."

"Okay, okay. I'll tell them. But this is the last story and then I get left alone to go to bed. It was the middle of last summer. Karl and
I was going to Camp Freedom, the same one where I got kissed and groped by that Indian chic. It was the third or fourth day there.
The main event that day was Native American culture and games. The boys, we got measured for height and the width across the
hips area. The female counselors made the loincloths for boys based on our size. We got these costumes the night before the
Indian culture day.

The next morning we put our loincloths on. Immediately I thought something was wrong with my loincloth. It didn't fit the way I
expected it to. It seemed to be too small for me."

Karl interrupts the story, "I switched out my brother's loincloth. I found the smallest boy in the camp, this short skinny dude who was
maybe eleven years old. I snuck into that cabin and traded out the loincloths, ha ha. I saw that kid later. It looked like he was wearing
a bath towel Josef's costume was so big on him."

"It was super small on me," Josef continued. "Half my ass was showing. The loincloth was so narrow up front I had some hairs poking
out on each side. I didn't want anyone seeing those black curly things so I had to yank em out. The camp counselors did look at me funny
when they saw me, but none of them made a suggestion of finding another loincloth. I could see a number of the female leaders
snickering, but nobody tried to do anything about it.

The events for the day were canoe races, then Bow and Arrow shooting. Then it was Indian leg wrestling. That is where things became
a problem. You know, for this type of wrestling each person lies down on their back, on the dirt. Each one raises a leg and presses it
against the other. You try to flip the other guy backwards with a leg thrust.

https://www.youtube.com/watch?v=Rq-JfXhyORc

I had to face off against this girl my age. She was wearing a tan deerskin looking dress that was very short, showed a lot of her legs.
When she lay down to lift up one leg the dress rode up so high everyone could see pink panties. I got turned on by that. The front of
my loincloth poked up as I got down on my back. I could hear some of the nearby kids saying something, but it was like whispers
and chatter I can't understand. I did hear words like BULGE and SEE SOME PUBES.

Then the leg wrestling began. That girl didn't outweigh me, but her legs were strong. She nearly flipped me over several times.
At one point her leg slid down to where her leg pushed and shoved my crotch area. I heard laughing after that. I looked over
at the counselors and the guy counselors were trying not to laugh. I wanted to win this match, win one for the boys team. I twisted
this way and that as I tried to shove that girl backwards with my leg. Finally, she just gave up and sat up. I lay there exhausted and then
I see that girl holding a hand over her mouth. I lifted my upper body and saw my dick was halfway sticking out from the loincloth.
For a moment I just didn't move...except for my dick which was moving. It was getting hard and got longer. By the time I made a move
to shove it back under the material of the loincloth I had a full hardon. I had a hard time getting it back under cover. There wasn't
enough cover for me to hide it easily. I guess being seen by so many people that day was the reason why the Indian girl came to me
to kiss and grope me at the swimming pool. She must have seen me or heard about it.

I never knew until today that it was my idiot brother who switched costumes on me. If I knew that then I'd have kicked his butt."

Josef stopped his story, awaited a response.

"I wish I was there to see that," Tabitha says. "But I've gotten to see much more than a quick glimpse of dick. Thanks for the storytime.
We'll go with Karl to the living room and maybe watch tv. Have pleasant dreams tonight, Josef. I'm so glad we are friends. You are
fun to be around."

Josef is glad to be alone in the room, glad to have a chance to have peace and quiet all by himself. He had finally gotten to feel better
after about a week of being sick, but all the activity has worn him down, and he went straight to bed.

* * * * *

Josef wakes up to find his mother tickling his feet. This would not be so bad, but the covers had been pulled away from his naked body.

"Rise and shine sweet boy. You must get up and get some breakfast...right now." Mother got up and she moved toward the door, then
she stopped to turn back. "Don't make me drag you by the dick to the table. I will do it."

Josef gets out of the bed. He tries to move to the dresser to grab something to wear, but mother grabs his hand.

"Come with me now. Eat now and get dressed later." Mother is in her nightie, the smallest one she has. The material is short on the
legs and low cut over the breast area. It would be the perfect little nightgown for a newly married young woman, but was being worn
by a mom.

Mother leads Josef by the hand to the breakfast table. There is a bowl of cereal with a spoon. Josef slurps up cheerios and milk.
A loud horn honks. Mother and son look toward the front of the house.

"Your bus is already here. Quick, get up and get to the bus." Mother pushes back her chair to get up.

As Josef is shoved toward the front door, mother helps get a small pack onto his back. Then the door opens and Josef is standing outside.
As he takes a few steps toward the yellow and black painted school bus, Josef realizes he still has no clothes on. However, the door
to the house has closed. The door to the bus is opening. Josef can't get back into the house so the bus is the only option. He climbs
up the steps to the seating level.

Inside the bus are all the kids Josef knows best from school. Some of the guys from PE class are there. Lenora and all the girls from
science class are sitting in the bus seats. There are no completely empty seats. The kids laugh as Josef moves down the center walking
aisle.

"I think you forgot something," somebody says.
"What's the matter? Did your mommy forget to dress you this morning?" another girl says with a wicked smile.

Then he spots it. Josef sees an empty seat at the back of the bus. He takes only one step further down the aisle when something
grabs him by the penis. Stopping and looking down, Josef sees Lenora has a hand wrapped around it.

"Sit next to me," Lenora says. "You want to be my boyfriend? I like friends who have a big one."

With the tugging relentless, Josef is pulled into the seat. He sits there staring toward the front of the bus as Lenora's hand continues to
tug away. He can feel it getting so hard and big. It's throbbing and his heart is pounding so loudly.

* * * * *

Josef wakes up in bed. The light is shining into the room from the outside. He halfway sits up but then freezes upon seeing he
is not alone in the bed. He has company. Some of the overnight guests have invaded room and are occupying his bed.
Tony is on left side. Tabitha is sitting to the right. Josef looks over to the other bed in the room to see Karl seated there,
watching and grinning.

"It's true. It's true. Josef does get an erection in the morning," Tabitha happily declares. "I thought it was just a tall tale boys get
boners every morning. But I'm glad to see it's a real thing."

"That is a big thing," Tony adds his observations, most accurate and factual. The younger boy then grabs the throbbing erection, lifts
it up to point straight upward, a hand wrapped around the base.

"I thought you said you would leave me alone," Josef protests the madness. Getting manhandled by a younger boy this way is
outrageous.

Tony maintains the strong grip, "I dare you to kiss it, you crazy twisted sister."

"I said we would leave you alone all night long. It's the next day now." Tabitha leans in close. She gets her face right up next to the
BIG THING. Her breath blows on the enormous glans. The cool air immediately causes a shiver to run through Josef's spine. A tickling
sensation on the balls occurs as the skin tightens up. Tabitha leans down more and she plants a kiss onto that mushroom head.
The girl laughs and she does a fake move of licking the head with her pink tongue. The tongue slips from her pretty mouth, moves so
close and then pulls back making the dick twitch and jerk as Josef gasps.
"I'm helping Karl make breakfast this morning. I'm gonna make pancakes and Karl is frying ham slices. Your mom says your punishment
is over now. But if you want to go to breakfast showing us all your um... big sausage and two hard boiled eggs...I'm not gonna complain."

"Everybody get in gear and get breakfast started," mother's voice comes from a distance away.

Karl jumps off his bed to head toward the kitchen, still wearing only underwear. Everybody in the room is still wearing what they
wore the night before, including the naked one. Tony lets go of Josef's penis. It flops down with a thud on the tummy. The overnight
guests clear out of the bedroom, leaving Josef sweating and panting on the bed.

He's free. The punishment is ended. Josef heads directly to the dresser. He pulls out boxer briefs from the top drawer. He really
wants to get dressed fully, but with everyone else remaining in underwear...well, he'll just have to go with the crowd. After all, after
so much exposure of all the goods, wearing underwear is almost like wearing a tuxedo.

Josef sighs at the site of the bugle pushing outward. Not much he can do about that. It will be a while before that thing settles down.
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Re: Life is Unfair: New September 15

Post by Trundle »

With the punishment now over I'm really intrigued as to where things now go. Surely Josef is still in for more humiliations?

Feels like endless possibilities await ! :D
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Re: Life is Unfair: New September 15

Post by TeenFan »

Trundle wrote: Tue Sep 15, 2026 10:50 pm With the punishment now over I'm really intrigued as to where things now go. Surely Josef is still in for more humiliations?

Feels like endless possibilities await ! :D
This one evening of punishment started when mother gave him the Raggedy Ann doll...and that was on Chapter 28.
That is thirteen chapters of endless punishment for poor Josef with the past revelations of previous incidents.

With this type of story there are ENDLESS possibilities.
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Re: Life is Unfair: New September 15

Post by TeenFan »

Life is Unfair
Chapter 42. The Cuckoo Cousin from the Country


It's Christmas time, and the family went to visit Uncle Caruso and Cousin Karela. Josef's uncle owns a small ranch/farm. He has a couple
hundred acres and a nice two story farmhouse that has been in the family for multiple generations. It's just the two of them in a large
house, ever since a divorce made Uncle Caruso a single parent along with full time rancher. It may not have been overly difficult, since
Karela is an only child when ranching families tended to be large.

Not only are country kids different from city kids, Karela must have been different from other country kids. Young girls in the country
are known for their tough, tomboyish ways since they usually do work with the animals, but Karela took it to a higher level. She could
rope a steer, put a shoe on a horse, drive a tractor, and she never ever wore a dress except for church on Sunday. Karela even kept her
dark brown hair cut short so the wind won't blow hair into her eyes when she is outdoors without a cowboy hat.

To top it off, Cousin Karela was not at all shy. She showed that six months earlier when she slept in the tent with the boys. She showed
she was willing to be like the underwear clad Josef and Karl when she stripped down to only panties to go to sleep in the tent. Back
then she didn't' have anything to hide up top.

When Josef got to see his cousin again after six months had gone by, she didn't' seem that much different. She was taller, but then so
was everybody else. She was a faster runner, and this was proved when she could almost stay with Karl in a race around the corral.
Her shoulders were broader which she proved by showing her male cousins she could do twenty pushups, thereby winning a bet with
Josef when he should have known better. Josef should have known better because Karela had not changed in another way, she
still considered Josef to be her FAVORITE relative, and she loved to hang out with him at all times.

"Are you wearing the red underwear?" Karela asks, and she says it loud enough for everyone to hear.

"Ah no...I only wear that for special occasions," Josef says, still feeling the slight sting of embarrassment at having family chatter
bring up his underwear.

"Sometimes he does work around the house, basic cleaning chores, and that is all he has on," mother was never shy about talking about
her oldest son's dressing or undressing habits.

"Too bad it's too cold to go to the swimming hole," the cousin says as she wraps her arm around Josef's waist. "You are my favorite
cousin in the whole wide world."

Karela gives her cousin a tight hug, and this is when Josef feels two distinct points of pressure on his stomach. Upon pulling back, Josef
looks more closely, and he can definitely see two areas raised up on the girl's shirt. Little Karela has sprouted newbie boobies.
Instead of being soft and cushy, Karela's small mounds are more like firm muscles with hard, pointy tips on them.

"When was Karela's birthday?" Josef asked his mother when the cousin was out of range of hearing.

"Let's see. I believe it was four months ago. Wow, your little cousin is almost halfway to being twelve. You kids are growing up so damn
fast."

It was the first time in many a year Josef had been to the ranch house. Karela showed her room to the two cousins. There were
posters of Rodeo guys on the wall. There was a poster of Brad Pit wearing a cowboy hat from one of his early movies, and other than
that poster there was nothing to be seen to suggest this was a girl's bedroom.

Karela is eager to show off her private space. "It is so cool to have you guys here. Daddy don't let me have boys in my room."

Karela has a nice small music system. She puts on a song. "This is something by 'Boy's Don't Cry'. I think you will know the song."

The song is known to Josef. It's a simple song, "I Want to be a Cowboy". Karela puts on her hat, and she sings along with the male
lead singer. While dancing around she points to Josef when singing "...And you can be my cowgirl." Then she pretended to be on
a mechanical bull at the pool hall, her arm raised in the air, her body swaying back and forth, a shit eating grin on her face.

It was so silly and stupid and it made the boys laugh till they almost cried.

After an early dinner, the adults wanted to go to town to do some shopping and stop at the bar n grill that doubles as a pool hall. It
was definitely not a place for kids. From 7 pm until around 2 am Josef was to be "The Man of the House".

After the parents were gone, Karela thought she'd teach her two male cousins how to do some line dancing and two stepping. She took
control of the Youtube on the tv, playing the appropriate songs. For an hour or so the boys learned all sorts of new moves.

After the lessons, Karela put on her favorite Brad Pitt movie. It was an R-rated movie that showed a fully naked woman at one point.
The movie is "Interview With the Vampire". Amazingly, Karl got bored with the movie, and he fell asleep crashed out on the couch.
Josef and Karela moved over to the Love Seat, the smaller two person mini couch. When the movie is over and all is silent in the room,
Karela gets all serious by saying, "That girl vampire...she wanted to grow up so badly, stuck in a child body all those years. But I don't
feel sorry for her."

"You don't?"

"I don't want to grow up. I am not sure I want to have wide hips and tits that make the guys hoot at me at the dance hall. I've seen that
already, even in the tv shows, the Westerns. The guys all get drunk and paw at the ladies in their colorful dresses or tight jeans. I don't think
I could handle that."

"Just stay out of the bars," Josef suggests.

"Have you ever wanted to be a girl?" Karela asks, her face completely devoid of any particular emotion.

The question caused some emotion in Josef, "Me?...be a girl? I don't think I ever thought about it. I don't look like one."

"Not with your equipment," Karela says, and finally she had something to laugh about. "I remember the 4th of July camping. I was amazed
when I saw you naked. That thing of yours...so big. I was totally envious."

Penis envy, now that wasn't something Josef expected Karela to say, and he isn't sure how to respond to that. He remains silent.
Karela giggles, one of the few times the girl acted or sounded like a young girl. "Hey uh, Josef. Would you tell me if I asked how big
you are?"

"Well...I am Five Foot and Seven inches. I weigh 110 pounds."

"Come on man...you know what I mean. Are you a horse the owner can ask a big Stud Fee?" Not only does Karela glance downward, she
reaches over to place a hand up against the crotch.

The breath sucked in as Josef's body stiffened. Karela was there last summer with a front row seat when mommy dearest demonstrated
some sex education. Was dear Cousin Karela asking for a refresher course? With the girl's hand cupping his manhood, the answer to
that might be a BIG FAT YES...
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Re: Life is Unfair: New September 17

Post by NudeBaG »

Fantastic return of Cousin Karela!
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