Jay's Bad Day

Jay's Bad Day

By Max Smart

This came from a Stripping and Humiliation Board archive, but it is ball busting and it is very good.

It was all the girls' idea, tricking Jay into a crooked strip poker game. He deserved it, though, and I happily joined in the conspiracy. All but one of us had a fabulous time.

I'm Sam, and I'm 17 years old. The girls are Chris and Julia, both 16. Jay is Julia's younger brother, a very irritating and obnoxious 14 year old. I have a crush on Chris and we're "sort of" going together, although nothing has really happened between us except for a little smooching and slow dancing. We all live in the same block and have played together for years - which is one reason it's kind of hard for Chris and I to graduate from kiddy playmates to teenage lovers.

I actually kind of like Jay. The person that was really out to get him was Julia, on whom he was always playing tricks and persecuting in various ways, such as embarrassing her in front of dates. He's a red headed, freckle-faced kid with a fair amount of baby fat still hanging around.

Recently Jay had pulled a few tricks that really pissed Julia off. He had pulled her bikini top down when they were swimming at the local country club pool, giving a brief but ample eyeful to quite a few boys from Julia's class and making her so embarrassed she begged her mother to let her switch schools. He had stolen a pair of her panties and run them up the flagpole at school. And finally, he and a couple of his friends had burst into Julia's room and caught both Julia AND Chris in the middle of changing clothes. Chris had on her underwear, but poor Julia was completely naked. This was the trick that pulled Chris into the act, and it turns out that this was a big mistake for Jay. He shouldn't have gotten Chris mad.

Julia is a cute, short blond, with a nice plump figure. She has a great butt, I must say. She may be very intelligent for all I know, as may Jay, but neither of them has let on if it's true. Chris, I think, is very smart and very clever. Of course, I DO have a crush on her, so I might be biased. Chris is tall, maybe 5'10", and very curvy. She is a brunette with curly hair and fabulous dark brown eyes. One think I didn't know about her until the episode I'm about to relate was that she could be pretty mean if you got her mad.

I was invited to take part for two, possibly three, reasons. One, they needed extra muscle. Two, I could deal from the bottom of the deck and could make sure that Jay lost. Three, and this is purely wishful thinking, Chris wanted me to have the fun of taking part in Jay's punishment because she liked me.

Chris made up the plan. I was to suggest a game of strip poker, played by the four of us out at Julia and Jay's parents' cabin near Lake --------. I would drive us because I had just gotten a license. Chris and Julia were to pretend that they didn't want to do it but would allow themselves to be talked into it by Jay and me. We didn't worry about talking Jay into it, he wouldn't need it.

Just as we expected, Jay went for it. Now, one fact about Jay is that he is very shy about his body and would absolutely HATE to really have to take his clothes off. But I knew very well that one reason Jay was willing was that he had no intention of actually taking his clothes off if he lost. He planned to simply refuse and laugh when people called him a cheater. He didn't mind being called a cheater. Of course he HOPED that one of the girls would lose and WOULDN'T refuse. It was a pretty sure gamble, from his point of view - lots to win, and nothing to lose.

During the drive everyone taunted each other about how embarrassed they were going to be without their clothes and how silly they would look. Jay blushed a couple of times but didn't seem too worried. I got a special thrill when Chris said to me, "I wonder what you have to show us, Sam?"

We got to the cabin and drank a little wine I had pilfered from my parents’ liquor cabinet. Then, as planned, I laid out the rules. First off, once you started to play, you couldn't quit the game until it was over. The game was over when one person had no clothes on. If you DID try to quit, that meant you automatically lost and would then immediately have to strip completely. I explained that we had to have a rule like that in order to make the game real. In order to raise the stakes a little more, the naked loser would get spanked by the winners and would have to follow any orders until he or she was allowed to dress.

Jay seemed very excited by this and agreed to go along. I'm sure that he figured he would just quit if he got into trouble and there was nothing we could really do about it. Chris and Julia pretended to object to the spanking part, but Jay and I talked them into it, mostly by taunting them for being wimps and prudes and scaredy-cats. It was really fun to see Jay unknowingly sow the seeds of his own doom, and the girls played their "shy and modest" parts wonderfully.

We played a very simple game - seven cards dealt face up. The owner of the lowest hand had to remove an item of clothing and give it to the winner. When someone finally lost all of their clothes, they would have to "pay" to get their clothes back by accepting ten spanks per item from that item's owner. This rule was presented as a bit of a punishment for wearing more items of clothing than normal.

It was tons of fun to tease poor Jay by having Chris, Julia and I each suffer losing streaks until we were down to our underwear. Jay, who had lost nothing so far, was exulting and making threats about how sore someone's bottom was going to be. By the way, Chris looked fantastic in bra and panties. I hadn't realized before what a nice set of boobs she had. Wow. I was doing my best to conceal my hard-on, but I'm not sure I succeeded very well, since Chris kept asking me if I was enjoying myself and winking.

Then young Jay's losing streak began, and it must have been incredible to him. He lost six hands in a row and was down to just his jeans, and, presumably, his underpants. He seemed a bit nervous, but still eager to go on, probably figuring that the odds were now in favor of him getting to see a set of naked breasts after the next hand. Unfortunately for him, he lost the next one too.

Chris and Julia had wicked grins on their faces as Chris said, "Well, Jay, off with the pants. C'mon, we're already down to our underwear."

"No. I quit. I'm bored." Jay tried to feign indifference.

"You can't quit, Jay." I said.

"Oh yeah? Just watch me." and he started to reach for his undershirt from Julia's pile of winnings.

"Jay, dear," Chris began, "If you don't take your pants off now, you'll be cheating and you'll automatically lose. That means you'll have to take everything off."

"Ha! Try and make me!"

Chris answered, "OK, we will."

We had been sitting on the floor. Chris, Julia and I started to get up, with the obvious intention of accosting Jay. Jay also clambered to his feet and tried to make a run for it. I caught him. I'm quite a bit bigger and stronger than Jay so it was an easy matter to wrestle him down to the ground. I sat on his chest and Chris grabbed his ankles. It was to be Julia's pleasure to do the stripping.

"Let me go! You bastards! Let me go! I'll tell! I'll tell!"

Julia said, "Oh shut up, Jay. Oh, Jay, I'm going to undo your belt now."

I couldn't see exactly what she was doing but I could hear the belt being unfastened even through Jay's threats and yells.

"Oh, Jay, I'm going to pull your zipper down, now." Julia was having a good time with this!

Jay's braggadocio took a downturn here. "No! Please, Julia! Don't? Don’t? ooooooohh!" As Julia suited action to word - I could hear the zipping sound.

"Down come your jeans, Jay. Hmmm, looks like your underpanties are coming down with them. Oh, well, might as well pull them down too."

Looking behind me, I could see that Julia was slowly working Jay's jeans and underpants down his hips.

"Ooooh! Look at the cute little wee-wee!" Julia cooed.

Jay began crying. "Nooooo! Stop! Let me go!" His face was scarlet.

Julia got Jay's pants and underpants down to his knees and then Chris helped her work them completely off. I got off Jay and Chris released his legs. Jay sprang to his feet, covered his genitals and backed himself against a wall of the cabin. He was still crying, begging us to give him his clothes back.

Chris said, "Jay, you've been a cheater and now you've refused to follow our orders. We're going to show you what the punishment for cheating or disobeying is."

The three of us grabbed Jay and dragged him to the heavy wooden table. It was lots of fun, especially since the girls and I were still in our underwear. I got some interesting glimpses of what seemed be a luscious pair of nipples on Chris's boobs.

Chris had come prepared with convenient lengths of rope and we managed to bend the crying, threatening young naked boy over the table and tie his legs and arms. Chris took care to pull Jay's legs as wide apart as possible before tightening the knots. Jay's freckled hindquarters were now defenselessly presented to me and the excited girls.

Jay had stopped threatening now and was just crying and begging us to let him go.

Chris suggested that the three of us put our clothes back on. I agreed that it was probably a good idea, but I was a bit sad about it. We dressed.

Jay's enforced posture gave us a good view of the crack of his bottom and of his twelve-year-old's hairless balls. I wasn't particularly interested in Jay's balls but the girls clearly were, and I was really getting off on their enjoyment.

Chris said, "Jay, you're now going to learn the penalty for disobedience or cheating when playing strip poker with the likes of us. Julia is going to do the honors. Here, Julia, take this fly swatter."

Chris hand Julia the fly swatter she had brought for just this purpose.

"Now, Julia," Chris said, "you know what the target is, but I don't think you know exactly how hard to smack it. Remember that boys are very sensitive there, so we don't want to be too rough (Jay started to shift nervously at this); but on the other hand, Jay deserves a strong punishment so we don't want to be too soft either. Why don't you try a practice swing on the arm of this easy chair?" Chris pointed to an easy chair that was place so Jay could see the action.

Whap! Julia smacked chair arm with frightening force.

Chris laughed, "Well, Julia, you can hit him like that if you don't want him having any children!"

Julia giggled, "How about this?" She hit the chair again, with a quite a bit less force. It was still enough to make me cringe at the thought of my balls being treated that way, but Chris wasn't satisfied.

"Now you're getting too wimpy Julia. Try something in between."

Smack! Julia did as asked and the chair received an intermediate stroke. I personally thought it was a bit strong.

Chris asked me, "Sam, you're a boy. What do you think? Was that last one hard enough?" I could only swallow nervously and nod, indicating that, yes, I thought it was hard enough.

Jay had been quiet through all this. I think he was stunned at the import of what was going on. His crying had stopped but he was panting with fear and his eyes were wide as they stared in horror at the sufferings of the easy chair. Finally he started to struggle in panic, pulling desperately at the ropes.

When he saw that he couldn't get loose, he pleaded to the smiling girls. "Don't, please, don't! You'll h-hurt me!"

"Well I certainly hope so, Jay. After all it's punishment!" Chris said gaily as she led Julia back around to Jay's shivering backside.

Chris instructed Julia, "Now, Julia, first get your range. That's good. Now move the swatter part up to make sure it will land right on the target."

With a mischievous smile Julia lightly touched the swatter to Jay's cringing balls. Jay jerked and gasped.

"Ahhhh! Oh! Don't! Don't! I'm sorry! You can spank me! I'll be good! I'll never cheat again!" Jay babbled, struggling some more, causing his balls to wobble a bit, which the girls seemed to find amusing.

"Now bring your weapon down. Good. Take aim. And try to remember how hard you hit the chair the last time? 3? 2?"

"No! Don't!!!" Jay begged.

"1? 0!"

Smack! The fly swatter hit home, directly on target, with enough force to make my balls cringe in sympathy.

Jay yelled out - a long drawn out yell of pain and shock. Then the pain began to swell and he treated us to a series of agonized groans.

Chris said, "Quick, let’s untie him."

We followed her lead and untied the ropes. Jay crumpled immediately to the ground grabbing his throbbing crotch and rolling on the floor in agony. I was somewhat horrified, but Chris and Julia were almost beside themselves with enjoyment as they watched Jay's sufferings.

Gradually the intensity of Jay's pain died down somewhat and he lay quietly with his hands between his legs, moaning softly.

Chris said, "Ok, time for the spanking. Jay, listen, you've just found out what the penalty for disobedience is. I want you to stand up, now!"

Jay ignored her.

"Ok, then, we'll repeat the treatment. Let's get him back on the table, guys."

"No! I'll do it." And Jay hopped to his feet with surprising agility, while somehow still managing to cup his family jewels protectively with both hands.

Julia ordered, "Hands at your sides, Jay."

"Ohhhh, please, Julia. I can't."

"Why Jay," cooed Julia, "Are you being disobedient? You must have liked your 'treatment'!"

Jay instantly brought his hands to his sides, displaying to me and the girls his prepubescent penis and balls. His balls seemed to have acquired a reddish hue from his recent "treatment". You could tell by the wrinkles in his forehead and that they were still paining the poor kid. He began to cry again.

"Ok," said Chris, "You're getting ten spanks for each item of clothing. That's, us let's see? Ten from Sam, 20 from Julia, and, hah! 50 from me! I feel sorry for your bottom, Jay, because you're getting your spanks with this and Chris magically produced a pretty scary looking riding crop.

Jay was too cowed by the thought of further "treatments" to protest too much. "Ooohhhhh! Please! Please, just let me g-go!"

"Let's see, I think we'll have you over the back of this easy chair. That's right bend right over. Now, now, don't squeeze your legs together so much. A little wider. Good, that's so we can apply any more treatments if you're bad."

"I won't be bad! Don't give me any more treatments!!" Jay's voice could be heard.

Jay managed to take all 80 strokes, but he suffered quite a bit. Several times he hopped up and had to be coaxed back down with threats of further "treatments". It appeared that just about anything was preferable, including a rather amazing set of marks on a very red and sore bottom.

Chris was the most severe. She gave her full strength to every stroke, producing full throated howls of pain from poor young Jay as she laid stripe after vivid stripe on his wincing, writhing butt.

Chris was finally finished and Jay continued to lie over the chair, crying his heart out. His bottom was a real mess - bright red with lots and lots of purpling stripes.

Chris said, "Very good, Jay. You were actually very well-behaved. I guess our 'treatment' is a very effective method for getting young boys to behave. Or maybe even older boys?" with this, Chris gave me a smile that made me a bit nervous.

She continued, "Now we have only to finish your punishment for cheating and disobedience. You see, the penalty is actually two strokes and you've only had one. We just gave you one of them at the start to get you to behave. So, let’s get the other one over with and then you can have your clothes back."

"Huhhh?" Jay mumbled. I don't think Chris's terrifying announcement really registered, or Jay would be protesting vigorously.

"Stand up, Jay." Chris ordered.

Jay slowly started to push himself up. His bottom was so sore he had to move very stiffly and gingerly. Reflex caused him to again guard his genitals.

Julia seemed to take this as her personal province, "Hands at your side Jay." Jay quickly obeyed.

Chris laughed. "Good boy, Jay. You've learned obedience for sure. Now, come over here." She said, leading the little lamb to his second slaughter.

When she started bending him over the table, the light finally dawned. Like I said before, Jay has never shown much cleverness. He started to struggle, but the three of us quickly had him tied down again in the same position as before, over the table and with legs well-spread.

"Gosh, Jay," said Chris with a sparkle in her eyes and a laugh in her voice, "I'm sorry you struggled just now. That means we have to add two more strokes, so now you get three. Julia, will you do the honors?"