This boy tried wearing boxers for a while. Looks like that didnât last long đ Now heâs begging to be exposed as the tighty whitie boy he truly is.
This guy is one of my favorites đđ·
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Claire Keane

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@fshsbdvhs
This boy tried wearing boxers for a while. Looks like that didnât last long đ Now heâs begging to be exposed as the tighty whitie boy he truly is.
This guy is one of my favorites đđ·

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The Contract
I put it in the introduction of my book, a promise that was tongue in cheek, that was meant in good fun, that would never, never, never actually have to be upheld: If I make $50,000,000 on this book, that's the last day I wear clothing. And to prove it to my fans, anyone who sends me the receipt for their purchase of this book has the right to host one party that I will attend in my new clothing-free life. I'll serve the drinks for the whole night.
When my editor looked over my introduction, he cocked his eyebrow, and simply said, "Bold."
"It's not like it's going to happen," I said. "Besides, with fifty mil in the bank, I could buy a house far enough from the public eye that I'd live my life in privacy. It wouldn't be too bad. Groceries would be delivered, and I guess it would be a good reason for me to never talk to my parents again."
"What about the book signings?" My editor asked, like this was a real conversation. "What about the promised parties."
"I don't know," I said shrugging. "It sounds kind of fun to me."
"A naked book signing sounds fun to you?" My editor said, sounding surprised."
"Once i earn that kind of money, I think my fans deserve whatever they want from me," I said, laughing. "But you've seen the sales on my last book. I barely made $10,000."
"You're writing is good though," my editor said. "It's a problem of marketing. And a naked book signing might just get the marketing up."
"No naked book signing until the fifty million," I said, surprised that my editor was even considering this.
"Okay, okay, no naked book signing... yet," My editor said. "But I think this promise of living forever naked and of becoming a free, naked bartender might be what we need to help your writing career really take off."
"I'm not a free, naked bartender," I said. "To get my services they have to buy the book."
"Fine, fine, whatever you say," my editor said. "But really, I think this is a stroke of marketing genius. We could make a website where people can buy your book, which would automatically submit the receipt, and then they'd be taken to your calendar where they could schedule your bartending services."
"It's never going to happen," I said.
"We could also get you on talk shows," my editor said. "No one is that excited to hear from any old writer. But the old cliche, sex sells, is really true."
"It won't sell $50,000,000 worth of books," I said.
"Of course, no one will believe you'd really go through with it," my editor said. "Unless... Would you be willing to sign a notarized contract agreeing to this deal? You'd sign for yourself, obviously, and we, the publishing company, would sign on behalf of your readers."
"I don't think that will be necessary," I said, laughing, even though my editor still looked more serious than I expected him to. "It's fifty million dollars."
"If it's never going to happen," my editor said, steepling his fingers and looking me up and down, "then why not sign a contract."
So, I did.
I went on talk shows before my book's publication, where late-night hosts made jokes about shrinkage, and workouts, and courage. One host even promised to have my contractual naked bartending party on his show. I laughed, and grinned, and leaned into the humor, enjoying what I assumed was my fifteen minutes of fame.
My friends all winked at me when they promised to buy my book, or they made me promise to not forget the little guys when I made my millions.
My parents were less understanding. My dad told me I was a shame to the family. Everyone at church kept telling he and my mom how they'd seen me on the TV, and how sorry they were that my parents had raised such a desperate, sinful, greedy child. My mom told me she'd never look at me again if I actually went through with becoming a nudist.
When the original sales numbers came in after my publication, I started to sweat. I made ten million. Every copy that had sold within a week, and my publishing company was preparing for a reprint.
"You better start looking at private jet," my editor said over the phone as he was sharing the numbers with me.
"You don't really think it'll happen do you?" I asked, my stomach performing somersaults. "It's just a temporary media hype, right?"
But it wasn't. As the initial reviews came in, my book was receiving praise, and there was buzz that I would be nominated for a few awards ("No matter what happens with this next print, you're contractually obligated to attend those award dinners, if you're nominated," my editor reminded me again over the phone).
The publishing company put me back on the media tour to talk about the writing. At each stop I was given time to plug what inspired the book, to talk about the process, and then the teasing started. Hosts asked if I was nervous. Hosts called me brave. The host who had promised to have me bartend on the air rolled out a drink cart that could be wheeled through his live studio audience.
My friends started asking for previews. "I'll see it all soon enough anyway," was said to me almost daily.
My dad called to tell me he'd written me out of the will, since I was already rich enough anyway. My mom stopped speaking to me.
At the second printing, my book sales landed at a crisp $42,000,000 in my bank account. Every copy sold. I had assumed that this printing would give me the answer on whether or not my life was going to change more drastically than it already had. I don't know if you've ever realized that everyone who meets you is actively picturing you naked, but I was now very aware that that was what was happening to me. All anyone wanted to talk to me about was my body. And my company was almost literally edging me, printing just enough books that I'd have to wait one more round before finding out whether I'd be allowed clothing again.
"You've got your private jet, right?" My editor asked. "If not, check your email, I've sent you a few listings for some small, cheaper jets. But you'll definitely need one."
Out of caution I bought myself a secluded cabin in the woods, far enough from civilization that I could still go outside and enjoy the sun, even if I had to go out sans all my clothing. I told no one where my cabin was.
I was back on the talk show circuit. This time we weren't talking about the writing, we talked about the printing details, we talked about the number of books that would need to sell before I had to honor my contract. My publishing company sent copies of the contract to each host, and I heard the stipulations read over and over again while audiences wolf-whistled and jeered. The website to buy my book and schedule my bartending services was posted at the bottom of the screen. Each talk show ended with the host promising that I would be back once my next printing had sold out.
Some fans started a website that had one of those thermometer charts that people often use for fundraising events. The visual of 42/50 hit home harder than anything else had. Under the chart were pages and pages of AI renditions of what I looked like under my clothes.
"Listen, it's over," my editor said over the phone one night. "The pre-sale numbers for your next printing put you at $75,000,000."
My heart plummeted.
"I gotta say, I don't envy you," my editor continued. "The publishing company wants to have a recorded event where we break the news to you, and where you turn your clothing over to us."
"It's not in my contract that that would be recorded," I said. "I'd prefer to just ship everything, and then probably never come back into your office, thanks."
"Believe me, I get it," my editor said, and I could hear the grin on his face. "And you're right, it's not in your contract. But I think you should do it. We're drafting a new contract that I think you'll like."
"Will I get my clothes back if I do the recording?" I asked, allowing myself a second of hope that he immediately squashed.
"God no," he said, chuckling. "You're our gold mine, and we aren't just going to give that up. But, we'll censor you on the recording. The minute there's full frontal, blurring effects will go on. You'll also be given a guaranteed five more printings of this book, and a contract for five books of your choice, plus a memoir deal that you'll write after five years all about your first five years as the world's most public nudist."
"I don't think so," I said.
"I would reconsider," my editor said. "This allows you to ease into your exposure. Sure, the live studio audience won't have the blur, but the world at large will. Eventually, you'll end up somewhere online, and everyone will see everything, but this buys you a little more time. Plus, the company is throwing in a private jet, since I know you haven't bought one yet."
I hadn't bought the jet. But now, I knew I needed one, otherwise I'd be pushing my way through busy terminals, the only naked person getting pressed up on by the hundreds of people hauling their luggage.
"It's tempting," I said.
"You're alternative is that we will send our enforcement team to collect what is ours," my editor said. "And you know how hard it is to schedule things as a company of this size. It's likely we'd forget to send you warning, so you could be out in the street, and our big, burly enforcers could show up and tear the clothes right off your body, in front of everyone, and those beautiful camera phones won't give you the same guarantee of a modesty blur."
"Fine," I said, understanding that my publishing company would be getting what they wanted.
The printing came and sold. My editor was right, my bank account now had over $75,000,000, and that was with the cost of my small, private cabin in the woods taken out. I signed the new contract the day of the recording in my editor's office before I was escorted to a filming studio. I had packed up every piece of clothing I owned, and had given the publishing company's enforcers keys to my home and my cabin so they could ensure that I was living up to my end of the contract. I hadn't withheld any clothing.
In the filming studio, my editor called me up on stage. Surrounding me on stage were at least fifteen mannequins, each dressed in something that had been mine. One was dressed in my talk-show suit. One was dressed in my favorite jockstrap that I used to wear on dates when I hoped to get lucky.
I wore my normal clothes: t-shirt, jeans, tennis shoes, baseball cap. I wanted today to feel as normal as possible, even though I had barely slept the night before, even though I knew today would not be a normal day.
The program wasn't long. I sat across from my editor, both of surrounded by mannequins, the jock-strap clad one framed by the two of us. He asked me about each outfit that was displayed. I told him the stories of where I got them, why I picked them, what I would miss about them.
"And which outfit will you miss the most?" my editor asked.
"The only answer to that question is the one that I have on right now," I said, and the audience chuckled appreciatively. Hungrily.
"I'd miss that one too, if I were you," he said to more laughs. "But the time has come to say goodbye."
The blood rushed to my face and to my crotch.
"I've been instructed to give you one last choice," my editor said. "Would you like to hand over your clothes or have them taken from you?"
Without giving me time to respond, two burly men appeared out of nowhere. Their hands groped and grabbed at my clothing, and my arms and legs moved at their command as I was shucked of everything.
In seconds, almost as quickly as they had appeared, they were gone, and with them every stitch of clothing I had worn today. There was no ceremony, no gentleness, no gradual removal to acclimate to new levels of nudity. I was fully clothed one moment. Completely naked the next.
And I stood there, hands at my sides, processing that I didn't even say goodbye to my clothing, that I would never again feel denim on my legs, or cotton sleeves against my arms. It took me nearly a full minute standing in front of my editor and my live audience to realize that I hadn't reached down to cover my cock.
Whoops! Aidanâs sagging pants were hanging just a little too low when he bent over to wash his hands & they fell to his knees with all his friends watching & laughing from the other room.
Pantsed at the laundromat! Not only exposed in little briefs, but folding an even smaller pair.
Harrisonâs new roommate was trying very hard to keep his secret. He was going the extra mile. He made sure the lights were out before he stripped down for bed. And was up early and dressed before Harrisonâs alarm went off. But alas, it eventually caught up with him, when he had stayed out late and was getting ready for bed. His back was to Harrison and he was completely unsuspecting. He was moving around ever so quietly and gently thinking that his roommate was asleep and unaware but the funniest part was the briefs that ridden up his crack a bit and had already given him a bit of a wedge. âThat will be a preview of whatâs to comeâ, he thought with a wicked smile. He thinks he is quite clever. He will find out differently when Harrison shows this picture to everyone he knows, including his roommateâs friends and a bunch of girls. Deserved punishment for such a tighty whitey nerd. This year sure was going to be fun
Harrison had suspected his new roomie was a tighty whitie nerd for a couple of weeks now. He couldnât help but notice that he had never changed in front of him and that he never left any dirty underwear lying around or even showed off clean underwear when he did laundry. They always seemed to be hidden beneath other things like shirts and shorts. He knew he could easily just check his roomieâs drawer and confirm his suspicions, but he wanted to catch him. It just seemed more fun after the lengths his roommate would go to keep his secret. One night upon stumbling in drunk when he was convinced Harrison was already asleep he removed his pants to reveal his tight little briefs. The best part was they were already slightly wedgied up his ass from whatever he had been doing that night. Harrison couldnât help but think how it was just meant to be, a sign of what his roomies future would soon be like. He snapped a pic as quietly as he could and couldnât wait to show it off to eveyone the boys knew. This year sure was going to be fun.

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First day back to school, He stared at himself in the mirror and couldnât help but notice how silly he looked in his tighty whities. He spent the whole summer trying to convince his parents to finally let him wear boxers or boxer-briefs, but it was no use. They told him he was still just a little boy, or at least he still acted like one, so his request was denied until he started acting his age, So another school year starting with him stuck in his briefs. He would do his best to keep it a secret, but since all his friends knew he wore them last year, he was sure they would check to see what he was wearing and the teasing would soon begin. Â
You glare at your roommate, but ultimately give in, pulling your shorts around your ankles, turning around and lifting your shirt to give him better access to your brief-clad ass. This had become a daily routine ever since you moved into the apartment off your friendâs sublease. He had told you his roommate was a bit intense, but you needed a place to stay and you didnât know guys still cared about other guys wearing briefs, or tighty whities as he always made sure to call them at your age. He said if it really didnât matter then you wouldnât mind him sending out the pic he had snapped of you when he first caught you in your little boy briefs to all your friends on Facebook and he knew he had you. Anytime, day or night, if you were in the house together and he asked you what time is it, you knew he wanted you in this position because it was wedgie time.Â
Graham had lost a bet with his housemate & had to step out in a pair of briefs. He thought nothing of it, even when his roommate had picked an embarrassing pair of Pup Patrol briefs. But what Graham didnât realize was that he was also going to get locked out during this challenge! He grabbed the door handle & realized in horror he was standing out in broad daylight wearing little boy briefs!Â
Graham looked over his shoulder to make sure no one was going to see him & saw in the distance his neighborâs teenage son with two friends from school. In less than 10 seconds, they were definitely going to be close enough to spot him in his little undies! How was he going to live this one down?
Johnathan liked everyone to know who the man in his relationship was even if he didnât have an audience other than his partner. He always liked to find guys in skimpy briefs, tighty whities were even better. It was funny when he found one who thought theyâd get to be in charge, as though they could be in charge of anything in that submissive state of undress. He would always dress in a suit for his sexual escapades and never take it off. If he dropped his pants heâd make sure they saw his manly boxer briefs and sometimes heâd even shove their whities up their asses like they were back in the school yard, just to drive home who was in charge. Heâd play it off like he had meant to just stick his fingers up there, but they got the point and deep down they knew, like he knew that he was just displaying his dominance.Â
Sheamus
Sheamus had lost a bet + now he had to hang out in his undies the entire rest of the night with all his friends over his placeâŠ

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Robbie begs his brother not to open the garage door - itâs bad enough that he has to wear tighty whities again, but letting the neighborhood see would be so humiliating.
Being a broke college student meant living life on the edge, of my laundry pile. I owned exactly two pairs of jeans, a handful of t-shirts, and my trusty old jockstrap, which I wore to the gym daily, hanging it to dry afterwards. On laundry days, my jockstrap became my unofficial uniform, meaning it never got washed. Every week, Iâd be marching around the dorm in that tired, overworked jock while all my other clothes washed. My roommates called it âThe Struggle Strap.â I told them it was vintage. They didnât buy it, but they definitely smelled it.
Bryanâs briefs part 1
Today was a huge day for me and I couldnât be more nervous. Today is the day I finally move out of my dadâs house and go to college. This was especially a big deal for me because I was homeschooled my whole life by my dad and largely grew up at home. I wasnât anti social or anything, I was part of a swim league and had friends in the neighborhood but a formal classroom setting was going to be a big adjustment, on top of moving into a dorm. This morning I woke up like I always do, in a pair of white briefs. I never thought much of my underwear as my dad and brothers all wore the same. I never changed in front of other guys either since for swim team we all just wore our swimsuits under our pants. I threw on a t shirt and some khaki shorts and went downstairs to double check my luggage. Dad was cooking breakfast and after we ate we hit the road.
Later that afternoon dad and I got to my new school and my new home. I walked into my room to meet my roommate. âHey Iâm Brian, your new roommate!â I say to the guy inside my room. âIâm Andrew itâs nice to meet you!â He says and shakes my hand. Andrew is an average looking dude and based on his decorations we seem to have a lot in common.He helps me and my dad move my stuff in and before I know it my dad has left me alone with my new roommate. Apparently Andrew had moved in early since he was from out of state. We spent the next 30 minutes making small talk and getting to know each other before Andrew had to leave for orientation. I had done mine online since I had already toured campus. While Andrew was gone I took some time to unpack. I hung my nicer clothes in my closet and folded t shirts and sweatpants in the dresser. There was a large deep drawer on the top of the dresser that I thought would be perfect for my underwear. I opened up my suitcase and started unpacking my hanes white briefs. These were my favorite ones though my dad and brothers had different opinions. My dad liked full rise staffords, Tyler my older brother liked fruit of the loom and my younger brother Jordan liked Jockey y-fronts. When I took out my hanes I noticed a wrapped present at the bottom of my suitcase that I hadnât packed. I opened it and found a note signed by my dad and brothers that said âhope you like these! Hereâs to new beginnings!â. Turns out they had each gotten me a pack of their favorite underwear so now, on top of having 18 pairs of Hanes I also had 9 pairs of fruit of the loom, 6 jockeys and 6 staffords. I opened up all the packs and threw the packaging in the trash can by my bed. I then organized my briefs in a careful stack in my underwear drawer so each day I could just grab the pair off the top and then go. After about an hour Andrew came back with a couple guys following him. They introduced themselves as Brad and Nicholas and apparently they met Andrew at orientation. They make conversation while I sit at my desk double checking my class schedule. After a couple minutes Andrew says âHey Bryan, do you have a trash can? I forgot to buy one and need to spit out my gum.â I point towards the foot of my bed and say âyeah man, right thereâ and go back to my computer screen. Suddenly I hear Andrew gasp and look to see him staring straight into the contents of my trash can. Before I can react he immediately says âguys I think our new friend Bryan is gonna have some problems tonite.â Brad replies, âoh yeah? Whatâs that supposed to mean?â as Andrew starts searching through my dresser drawers. âHey Andrew stop!â I say standing up but itâs too late. As I get to my feet Andrew pulls open the top drawer of my dresser, my underwear drawer, and reveals my briefs to Brad and Nicholas. âOh my god dude, tighty whities?â Nicholas says. âDude I havenât worn those since I was 6! I thought this was college!â Brad laughs. âWhat do you mean?â I respond. âI though everyone wore those?â. Andrew steps forward and says, ânope! Letâs show him boys.â And Andrew drops his shorts. Boxers. Brad drops his pants. Boxers. Nicholas drops his pants. Boxers. They pull their pants up and step closer to me. âAlright boys lets teach Bryan a lessonâ Andrew says. Next thing I know all three pounce on me. Nicholas and Andrew shove me back into my desk chair while Brad grabs a role of tape and tapes my arms and legs to my chair. âGuys stop please!â I yell but my pleas fall on deaf ears. âAlright Bryan we showed you our underwear now itâs your turn.â Andrew says as he reaches for my shorts. He undoes my button and zipper and pulls my shorts to my ankles revealing my tighty whities. All three of the guys burst into laughter as I stare on in horror. They took turns posing with me after Brad taped my mouth shut and then they took my shorts and shirt and put me in the lobby elevator for the rest of the night.
I spent the next several hours going up and down with new students and their parents who were moving them in. Every time the door opened a new crowd witnessed me in only my tighty whities...boy college was going to be rough.
Bryanâs briefs part 2
Needless to say it was a long night. Not even 3 hours into moving into the dorms and I was already being humiliated in my tighty whities. I spent 2 hours in the dorm elevator taped to a chair in my tighty whities. The elevator went down, the doors opened and a crowd of students saw my briefs. The elevator went up, the door opened and a new crowd saw my briefs. This cycle went on for 2 hours but it felt like days. Finally Andrew came and got me out. He took me back to our room where Brad and Nicholas still were and let me get dressed again. âHey man that may have gone too far. I mean itâs pretty embarrassing to wear tighty whities in college but we may have embarassed you too much. No hard feelings?â Andrew said. âHahaâŠyeah itâs alright guys.â I said. I definitely was humiliated but I didnât want to miss out on my chance to make new friends. We went to have dinner at the dining hall and made it to bed early to be ready for school the next day.
I woke up early, took a shower and started to get dressed. I put on a pair of staffords white briefs, jeans and a blue sweater. I liked the feel of my new staffords but noticed they stuck out of my jeans a bit more than my hanes did. I got my stuff together and made it to my first class. I sat down in the second row next to a big muscular guy. He turned to me and said âoh shit itâs tighty whities!â I realized he must be referring to the elevator incident and I said âoh uhâŠyeahâ. âHey Iâm Christopher!â He says. âIâm Bryan.â I respond. âSo likeâŠtighty whities? That was a joke right? Like a one time thing?â Christopher asks. âOh sure, Iâm a boxers manâ I lie through my teeth. Christopher immediately grabs my sweater and lifts it up revealing my white briefs sticking out of my pants. âBullshit you are!â Christopher says raising his voice. âI donât take well to liars Bryan. Watch your back around me.â I try to respond but class is started by the professor. I go about the rest of my day which is uneventful.
After class I return to the dorms to hang out with Andrew and Nicholas. They tell me they want to take me to a party tonite to make up for the embarrassment. âNo shenanigans this timeâ Andrew says and we spit shake on it. We get to the party a few hours later and thereâs tons of cute girls around. Naturally though I donât know anything about talking to them so I stick next to Andrew. It doesnât take long for things to go south. Christopher is standing on the other side of the room and is glaring at me. Andrew promised no shenanigans but Christopher told me to watch my back just this morning. It starts getting hot in the house so I head outside to cool off. Immediately I get flanked on both sides by Brad and Nicholas who grab me. âWell well well looks like you fucked up!â I hear Christopher say behind me. âWedgie time boys!â Christopher yells as brads hands shoot down my back. Brad grabs my tighty whities and gives me first ever wedgie. I yell out in shock and pain as Iâm lifted to my toes. My briefs shoot up by butt, and crushes my balls. âBrad stop please!â I yell but Christopher responds âno way briefs boy. You lied to me today. On top of wearing tighty whities. Big mistake.â Brad turns me around to face Christopher as he reaches for my belt. Chris slowly undoes my belt while he stares into my eyes, relishing the humiliation Iâm feeling. He takes off my belt and undoes the button my jeans letting my pants fall straight to my ankles. He uses my belt to tie my hands behind my back, through the legholes of my briefs and letâs me go. I try to get out but any struggling I do with my hands makes my wedgie worse. I swear my briefs are inside my asshole at this point. Christopher then grabs the waistband of my briefs and hangs me off of a tree in the front yard. Then Christopher goes inside and addresses everyone at the party. He says âattention everyone! We have a boy who came to college and thought it was ok to lie! And on top of that he thought it was ok to still wear tighty whities! So without further ado ladies and gentlemen I give you Bryan Stevens!â As he finishes his speech he opens the massive front door revealing me to a massive crowd that pours into the front lawn. I struggle again but only manage to deepen the wedgie and make my jeans fall to the ground. Once again it was going to be a long nightâŠ

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The morning after the Super Bowl, he entered the kitchen with his glasses, his coffee mug, and absolutely nothing else. He had placed his bet on the wrong team and he was now about to go to work while still completely nude.
His wife got confused when she saw him leaving the house with only a briefcase to hide his manhood, 'You're heading out already? Erm, aren't you forgetting something... important?'
'It's for a bet I made with the boys while watching the game last night. I can't go back on my word now,' he said sounding defeated, avoiding eye contact with his wife as he recounted the dumb drunken decision that brought him to his current naked state.
'I guess it's not a good time to remind you that we have a parent-teacher conference in the evening. Do you want me to bring you an extra set of clothes for later?'
'No need. I've got to stay um, undressed, for the entire day... Just bring me a beer instead. I'm certainly going to need one if I'm going to the school like this.'
Definitely a great bet!!đ„”đ„”đ„” kinda wish they would have made him do this for a week or something!!đ€©đ
Master started requiring he wear briefsâŠand now only tighty whities as his briefsboi training continuesâŠ
âŠhe was eased into tighty whitiesâŠmet the guy onlineâŠMaster first demanded he remove all of his âbro-boxer briefsââŠand eventually remove all of his colored briefsâŠ
âFrom now on âŠtighty whities only. And daily pics, boiâ
âYes, Sir!â
âŠhe was learningâŠnot even aware of his transformationâŠjust knew he wanted to please the guyâŠfelt goodâŠcalling him SirâŠand back in his boyhood underwearâŠsomething about this guyâŠa little older than him⊠masculineâŠdemanding tooâŠfuck he found he wanted to please himâŠreminded him of his football CoachâŠfrom back at Jr. CollegeâŠalways tried to please himâŠsomething about that man, tooâŠ
YeahâŠlately heâd get hard âŠas he would slide on a new pair of tighty whities the guy had sentâŠfelt rightâŠ
âŠguy started demanding pics with his hands behind his backâŠlegs spreadâŠhead downâŠrear views tooâŠfuck that turned him onâŠsubmitting like thatâŠto his demandsâŠ