Life is Unfair: New October 6

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
Post Reply
NudeBaG
Posts: 1975
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2054 times
Been thanked: 4122 times
Contact:

Re: Life is Unfair: New October 1

Post by NudeBaG »

Steamy

Tags:
User avatar
Trundle
Posts: 543
Joined: Tue Feb 08, 2022 12:55 am
Has thanked: 1394 times
Been thanked: 804 times
Contact:

Re: Life is Unfair: New October 1

Post by Trundle »

Have a feeling Josef's dare will backfire....

Teenfan is always so creative so I cannot wait to see what other potential dares there are and where this is going, I just hope wherever it does lead ends with Josef embarrassed!
User avatar
Jeepman89
Posts: 1753
Joined: Sat Oct 12, 2019 12:10 am
Has thanked: 5064 times
Been thanked: 1867 times
Contact:

Re: Life is Unfair: New October 1

Post by Jeepman89 »

Let the game begin!
TeenFan
Posts: 2389
Joined: Thu Sep 08, 2022 1:28 pm
Has thanked: 1520 times
Been thanked: 2647 times
Contact:

Re: Life is Unfair: New October 1

Post by TeenFan »

Life is Unfair
Chapter 50. The Early Rounds


The alternative style of doing Strip Poker, a game with the drawing of dares added, soon has Josef at a disadvantage.
The game is similar to baseball, in that three strikes you are out. Each boy has on only three articles of clothing. Anyone with
a losing streak is gonna be streaking before he knows it.

Tabitha is the one to propose the game, as well as the specific rules. She is also the permanent dealer, and this has Josef worried.
Could the girl know how to cheat? Could she handle cards well enough to deal from the bottom of the deck?

The second round of dealing was better for Josef. He got dealt two Jacks. It's a good start. He tosses the other three cards and
surprise, surprise he gets two Seven cards. Two pair sure ain't bad. There is no betting in Strip Poker. Everyone merely presents
their hand to see who has the lowest value set of cards. It's not about winning, it's about not losing. Lowest hand loses
clothing, and Karl is the next one to take his shirt off.

Tony and Tabitha both look so smug and confident, it makes Josef wonder if there is a way those two could work together. He'd have
to keep an eye on them.

Round 3: Josef gets a shitty hand once more, an Ace with a King, plus a Queen. Then he has a Four and a Nine. The chances of getting
a high straight (Ten through Ace) are extremely on the weak side, but it is the only chance. The two cards he gets back are another Nine
and a Queen. He ends up with a pair of Queens. It's a chance to stay out of the bottom.

Karl shows two pairs. Tony shows a freaking three of a kind. It's down to beating Tabitha. All eyes are on the dealer as she places
her cards, and lo and behold that girl has a single pair...but it's a pair of Aces!

"Take something off Mr. Studmuffin," Tabitha giggles as she scoops up all the cards to reshuffle.

Josef removes his shorts. He is down to his last stitch of clothing, the boxer briefs. One more loss and he will be the first one out,
but still having to keep playing. Under his breath Josef cusses the poker gods. His pair of Queens beaten by Aces. If he didn't have
bad luck he'd have no luck at all...what the fuck.

Round 4: Even Tony is chuckling as the next round is dealt out. So far only members of the Korleki family have lost. The two members
of the Torres family still have all their clothes. Josef looks at his cards and his heart nearly skips a beat. He has two Kings and an Ace.
Hmmm, that is a tough one. Does he toss three cards in order to improve on getting another King? Or does he keep the Ace, hoping to
get another one for a decent two pairs? Well, three of a kind beats any two of a kind. Josef tosses the three cards. Finally, something
good happens and another King shows up. Three of a kind is guaranteed to keep him off the bottom.

Karl has two pair. Tony has a pair of Aces. Josef has them beat, so he eagerly awaits the cards from the dealer. Tabitha has no smile
on her face as she puts her cards down. She has zilch, nothing at all as she missed out on a straight. She had the Four, Five, Six, Seven...
and a Jack. Missed out on a straight she did, and she had to go straight to taking something off.

Tabitha takes off her t-shirt. Josef and the other boys get their first glimpse of Tabitha wearing a bra. The bra is small. The bra is
blue. The bra is lovely to look at but what is underneath that bra is going to be even more lovely if the girl loses a couple more
rounds.

Josef feels the stirrings of prurient interest causing a tightening at the front of the underwear. Tabitha isn't showing much, not yet, but
she has lost a round and that means more good luck may follow. Her brother Tony is the only one fully dressed.

Round 5: Josef's cards are friendly once again, and the draw improves it. He ends up with three Nines. This proves to be the
best of the round. It's the first time Josef has the highest hand, and Tony finally is at the bottom. Tony shows no fear
taking off his shirt, tossing it onto the small pile of clothes at the center of the playing area. Everyone has lost something, but
so far Josef is the only one who lost twice.

Round 6: Bad luck strikes back. The deal gives Josef nothing, and the draw makes no difference. He doesn't even have a pair
to work with. His only hope is somebody else is equally destitute of card strength. Josef places his hand down first, knowing he
cannot win, but maybe he won't lose either. Karl has a better hand. Tabitha has a better hand. It's down to what Tony places on
the floor. Tony looks a little worried as he shows the cards, and he too has less than a pair. Two hands that have nothing, but
somebody has to have the worse nothing. Josef looks at his hand to see the highest card is a Queen. Karl quickly points to the
hand of Tony as he says, "That one has a King for high card. Tony beats Josef."

Another round, another loss, and it is time to pay the price of participation. It's the third strike and Josef is out, will be out of
clothes but not out of the game. He hooks the thumbs into the waistband of the underwear, starts to pull down.

"Wait...you can't do it like that."

It's the voice of Tabitha, the dealer and the keeper of the rules. "When somebody loses their underwear you have to stand up.
Take the underwear off. After tossing it onto the clothes pile, do a slow turn all the way around with your hands on your head."

"You didn't say that before," Josef says. He makes no move to stand up.

"Everyone in favor of this rule raise your hand," Tabitha raises her hand.

Immediately two more sets of hands go up. Tony and Karl are in complete agreement with Tabitha.

Grumbling at his lack of luck, Josef gets to his feet. Nobody else in this game is close to losing, each of the others having lost
only once. Six rounds of this game and he lost three of them. Josef sees no mercy on anyone's face. They are all eager for the
first victim of the night. Josef slides the boxer briefs down his legs. Stepping out of them he tosses them onto the growing pile on
the floor.

"Hands on head big brother. Spin around and show us." Even Karl has no sympathy. Josef can feel his dick twitch and start to rise upward.
It's always the same old thing. As soon as he gets naked with anyone watching his dick decides to do that little trick of doubling in size
and getting long followed by longer. It happens so fast. As he turns full circle around the partial erection becomes a full one. All three of
his opponents are laughing at the first loser.

"You can sit down now," the little boss lady says. "But no covering up. If that thing sticks up it's too bad."

Josef sits down, and he looks down to see the One-Eyed Monster staring back at him. From this seated position, sitting cross-legged,
the dick sticks straight up toward the ceiling. The mushroom head presses against his bellybutton. Tabitha can see the underside
of the shaft all the way to the balls pushed out from either side of the shaft, pushed out because the floor makes em spread out wider.

Tabitha deals out the next round. The 7th round is more favorable to Josef, as he ends up with two pair. He had to be reminded once
again, what happens to the naked ones in the game. For the naked one there are two results that are of consequence. Win the round
and put underwear back on. Lose the round and draw a dare. Just for emphasis, Tabitha places the baseball cap on the floor next
to the discarded pile of clothes, Josef's red and while boxer briefs topping the small pile. Karl is the loser, and he removes the shorts,
leaving him with only boxers.

Round 8: Josef is still hard and he has to fight the urge to stroke himself, and this is made worse when Tabitha ends up with the
lowest hand of the round. She had a pair, but her two Two cards were not enough. This is a moment every boy in the room was
anticipating. When the girl loses a second time, is she going to take her shorts off to reveal the panties, or would she be bold enough
to take the bra off? Not surprisingly, Tabitha takes off her shorts. Josef feels his dick twitch as soon as he gets a look at Tabitha's
tight fitting panties that are light tan in color. They are not fancy or colorful, but they are a tight fit on the girl's body. The side
seams are only an inch apart, and the legs look fantastic. Soccer playing does wonders for a girl's legs.

Now all the boys (except for the naked one) are chuckling and grinning as Round 9 begins. Everyone is more interested, more focused
since the girl in the room has lost half her clothing privileges. The underwear only clad dealer deals out the cards. Josef has an interesting
decision to make when he sees the hand dealt to him. It's another grouping of four of the same suit. Four Heart cards and a Diamond.
Dang it, another 25% chance to have a decent hand to present. Josef tosses the Diamond and is rewarded with another freaking Diamond.
His only hope is the Ace card will let him beat out someone who doesn't have shit to work with.

Karl has two pair. Tony has a pair of Eights, and Tabitha is grinning like a cat when she lays down a Full Fuckin House. Three Tens and
two Queens, the Queen of the Poker Palace is giddy with glee.

Tabitha grabs the baseball cap, and she lifts it up in the air. "Draw a piece of paper, Josef. You have to do a dare."

This is what Josef was dreading the most. Not only was he the first one to lose three times, he's already lost for the fourth time.
The naked one who is last must draw a dare. Josef reaches up to the cap. Feeling around inside he grabs a slip of paper.
He unfolds the paper, everyone leaning in to hear him read what is written. Josef reads it silently, and he rolls the eyes while shaking
the head. Josef doesn't look like a happy camper.

"Go on, read what it says," Tony shows his eagerness to see the oldest boy in the group do something for the entertainment of all.

Josef slowly says the words, "Jump rope for two minutes. That is what it says."

"Ha ha. I wrote that one," says an excited Karl, and he jumps up to his feet to go fetch the jumping rope.

Everyone backs up a little to make room. Josef stands up, and is not happy that he is still standing up down under. He is still hard as a
rock. Tabitha is licking her lips as she watches Josef get in position to do his jumping. The sound made must be music to her ears,
as Tabitha smiles the whole time. The feet thump thump on the floor. The rope makes a clack, clack, clack as it strikes the floor.
The erection makes it's own sound and monotonous rhythm as it goes whack, whack, whack, smacking the tummy over and over.

Everyone has a reason to laugh as the big dick swings up and down like a mighty lever. The mushroom head is like the round end of a
drumstick that bangs the big drums. The jumping makes its own music and rhythm of THUMP, CLACK, WHACK over and over again
as the two minutes are counted down on Tabitha's phone.

"The balls don't move much. They are too tight. Too bad," Tabitha observes.

Tony makes his observations, "They are tight but really big."

Karl adds some insider information that has the sleepover guests intrigued. "Those big balls are fully loaded. I don't think Josef has
jerked off for several days. Tell me I'm wrong if I got that wrong."

Josef says nothing to refute what his younger brother just said. He can't say nothing because it is true. Josef hasn't busted his big
balls in four or five days. Mom got tired of finding used and disgusting tissues lying around and under the bed. She told her son that
he was wacking off too much and to take a break. Josef wonders if he will end up regretting taking a short masturbation vacation.

By the time the two minutes are up, Josef's penis has changed color to pinkish. The stiffness even more pronounced, the dick is
throbbing and twitching up and down when the jumping ended as if it wanted to do more motion, more action. Having an audience
always gets his juices flowing. Josef looks down as he feels something happening.

"Eww...what is going on there?" Tony says as he points a finger at the glistening wet glob slowly oozing down the underside of
the shaft.

"Oh cool, he sprung a leak," Tabitha laughs for a moment. "You still have some stuff to learn little brother. Big boys like Josef have
dicks that can do all sorts of wonderful things. Not only can they spit stuff out, they can also drool. It means he is getting super
excited and having fun. Aren't you having fun, Josef?"
Last edited by TeenFan on Sat Oct 03, 2026 2:30 pm, edited 1 time in total.
User avatar
Jeepman89
Posts: 1753
Joined: Sat Oct 12, 2019 12:10 am
Has thanked: 5064 times
Been thanked: 1867 times
Contact:

Re: Life is Unfair: New October 3

Post by Jeepman89 »

Awesome chapter.
User avatar
Trundle
Posts: 543
Joined: Tue Feb 08, 2022 12:55 am
Has thanked: 1394 times
Been thanked: 804 times
Contact:

Re: Life is Unfair: New October 3

Post by Trundle »

Josef is always so unlucky :D

I understand now why the story is called Life is Unfair.
Themarble
Posts: 787
Joined: Thu May 07, 2020 8:41 pm
Has thanked: 2283 times
Been thanked: 1344 times
Contact:

Re: Life is Unfair: New October 3

Post by Themarble »

Such a great chapter here. Josef being the first one to be nude is a given, but will anyone else get nude? Perhaps Tabitha? Will lose her bra? So many possibilities. Let's hope Josef doesn't get his own dare, haha!

Can't wait to see where this goes. This story constantly keeps up the embarrassment and excitement for us readers!
flyingmonk
Posts: 34
Joined: Sat Sep 19, 2026 4:07 pm
Has thanked: 39 times
Been thanked: 99 times
Contact:

Re: Life is Unfair: New October 3

Post by flyingmonk »

Looks like the moment of truth is about to arrive :)
TeenFan
Posts: 2389
Joined: Thu Sep 08, 2022 1:28 pm
Has thanked: 1520 times
Been thanked: 2647 times
Contact:

Re: Life is Unfair: New October 3

Post by TeenFan »

Life is Unfair
Chapter 51. Beware the Baseball Cap of Dares


After only nine rounds of strip poker, Josef is not only naked, but also the first one to have to pick a dare from the baseball cap.
To recap the action so far, the state of undress for each player is:

Karl is down to boxers only.
Tony lost only one time, minus the shirt.
Tabitha lost twice, has panties and bra on.
Josef is naked.

Being a four time loser in just nine hands of poker is tremendously rotten bad luck. Josef had to stand and display himself. He had to
jump rope while the other three players sat and watched as his weenie went wack-a-mole with the air as he jumped up and down for
two freakin minutes. If only he could get out of here, but there is no place to go. His own room has become a chamber of horrors,
and the game is about to begin again.

Round number 10 gets off to a good start for Josef. Tabitha deals him two King cards. He tosses the other three and he gets another
King in the Draw. Three King cards will keep him from being on the bottom again. Naked people who draw the worst hand have to do
a dare. Sure enough, the three of a kind is kind enough to not be last place. Tony gets his second loss of the game, and the youngest
player takes off his shorts to reveal a childish pair of DC Comics Avengers boxers.

It's getting close to the end for some other players. Karl and Tony are in their underwear, and Tabitha is two losses away from full
exposure. Despite having to sit and play with a dick that is still hard and throbbing, still sticking up showing no sign of weakening
after the humiliating two minutes of jumping rope, Josef is looking forward to seeing somebody else get naked.

Josef realizes the next round will end up with somebody getting embarrassed. Either a boy ends up all the way naked, or Tabitha
the dealer will have to take off something. It won't matter what the girl takes off, bra or panties it's good either way.

The very important round 11 gets started. Tabitha deals the cards a little slower. Perhaps she too is aware that if she loses it
will be decision time for her, that she will have to show part of her prized assets to three guys eagerly wanting to see some female
skin. Josef gets one of those hands that are full of potential but rarely succeed. He gets the 7,8,9,10 and a Queen. He tosses
the Queen and hopes and prays. There are only two cards in the deck that can help. Upon getting his draw card he places it against
his chest, and he can nearly hear the beating heart. Holding it higher, the heart skips a beat as Josef got what he was praying for.
He got a six card and that completed the straight. It's a fairly high value hand and guarantees he won't be at the bottom.
But will it be good enough to be the best hand of the round? For a naked player, winning the round means getting the underwear
back. Even if only temporary, regaining underwear means Josef could end up the winner of the entire game. It's a long shot
but possible.

Josef places his straight onto the floor. Tony looks at the hand, and he cusses as a two pairs hand is placed on the floor. Tabitha
giggles as she presents her hand, and to Josef's dismay the cards the girl lays down are all HEARTS cards. Would you freaking believe
it...once Josef has a straight, the dealer magically pulls out a Flush. It's like being set up.

Everyone turns to look at Karl, who was sitting quiet and motionless. Josef's younger brother places a hand of crap onto the
floor having missed out on his attempt at getting a flush with a Club card not being a perfect mate with four Spade cards.

"Time for another nudie boy to join our party," Tabitha states the obvious. "Stand up and model yourself for us."

Karl stands up. He slips off his boxers, tosses those onto the pile of clothing discards. He places hands on head as he slowly
turns around 360 degrees. Josef is somewhat surprised to see his brother is actually grinning as he bares his body to the group.
At times Karl is more at ease with casual nudity than Josef is, though for some strange reason Josef is usually the one who ends
up naked in a group setting.

"Look at that. First time I seen him with hair around the dick," Tabitha points and she whistles. "He's a little bigger too, but he's
hiding the little head, what a shame."

Karl does blush a little, but he seems to be enjoying himself. Sitting down again the game resumes. What Josef likes about this
development is now there are two naked players who might end up at the bottom. Another player might end up doing a dare.
There are three unopened dares in the cap.

"I have a question for you, Karl," says Tabitha. "How do you know Josef hasn't jerked off for at least several days?"

"Shhh, no," Josef says toward his younger brother, as Karl laughs.

"Ha ha, I got to do it brother. Mom made me Josef's masturbation monitor. I'm to keep track of when he jerks off."

Josef can feel his face burning, his cheeks turning red at the revealing of what should be a private matter. What happens at
home should stay at home.

"Really? How did that happen?" asks Tony.

"Mom kept finding wadded up gunky tissues around the house. She found some in the living room next to the couch. She found
a pile of em under the bed. She even saw evidence of it in the bathroom trash. She knew somehow those wads of tissue paper
were not used to blow his nose. Mom called a family meeting, and we all had to listen to what she wanted to do after doing
research on that issue. Mom declared a new gameplan where Josef is to bust a nut no more than once each week."

"Once a week? Really, is that all he is allowed?" Tabitha is amazed at this, and understandably curious.

"Yep, that is it. Any longer than that he runs the risk of having a wet dream. Doing if four or five days each week was gonna give
him callouses on his cock or something like that."

Josef wishes he could crawl under his bed to hide out for the rest of the night, but nothing will be any good as long as everybody
is gathered in his bedroom. Also, that girl keeps staring at his penis during this unexpected detour.

"Ha ha...no wonder that thing keeps sticking up like that. Of course I think it looks lovely on him. All boys should have boners
all the time." Tabitha giggles and she bumps a fist onto Tony's shoulder. "I can't wait till you are fourteen years old. I bet I'll
be able to find your used tissues all around the house."

Tony shakes his head, "Oh no, not me. I'll only do that in the bathroom and flush the evidence."

It's back to the game and Tabitha deals the cards as round 12 is off and running. Josef picks up his cards and his face scrunches up with disappointment. A lot of nothing to work with. He does have an Ace, so he keeps that and discards four cards. It is mostly more junk,
but the fourth card handed to him is another Ace. A pair of Aces should do okay.

This time, Josef wants to hold out presenting his cards to the end. Karl goes first, and he places down two Jacks and two Kings.
Tony goes next, and that kid has two SIX cards and two TEN cards. Dang it, both of them have two pair and Josef is at the bottom
if Tabitha also has something better than a pair.

All eyes are on the dealer as she puts down her hand. A groan issues forth from Josef's mouth when he sees three QUEEN cards!
He is last again. Josef had a decent high pair, but he lost again. Not again!

Tabitha is all smiles as she reaches for the baseball cap. "Here we go again, Josef. You must be the worst poker player ever."

Josef feels his face reversing itself and turning pale as he eyes the dreaded baseball cap of dares held up in the air. He reaches into
the cap and feels around. Choosing a piece of paper he pulls it close to himself. Dang it, he is the loser once more, and once
more he pays the price of getting involved in this stupid game. He thought he had a decent chance with four people playing.

Opening the paper he reads the words written on it. He stops reading after seeing the first words. He doesn't need to read any more.

"Well, what is it. Tell us what you have to do." Tabitha is being her typical bitchy and bossy self. She gets that way whenever she is
in control. "Come on Josef baby, what have you got there?"

His voice soft and nearly choking, Josef reads, "Give the winner a lap dance".
NudeBaG
Posts: 1975
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2054 times
Been thanked: 4122 times
Contact:

Re: Life is Unfair: New October 6

Post by NudeBaG »

Tabitha is in her undies and about to get a lap dance from naked Joseph?!
She better be careful not to get handsy, or things could get messy
Post Reply

Who is online

Users browsing this forum: Ahrefs [Bot] and 17 guests