"Aaah! My ass is going to split in two!" I screamed as pain hit my ass in places I'm embarrassed to mention. "Hold on! We are in the third briefs!" He said as he tugged harder at the underwear I'm wearing, although now that must look like flossing between my buttocks. You must be wondering how I got to this situation. Almost naked and with ridiculous underoos about to reach my neck. Well, it's a strange story, so make yourself comfortable and get your underwear off your butt. This is the story of the most embarrassing Christmas season of my life. --- I should introduce myself first. My name is Nicolás Aumada, I am 22 years old. I am a man of almost 2 meters, black hair and tanned skin. I considered me quite attractive and many girls confirm it, even some boys. Not that I'm interested in other men's opinions about it! I currently live in a small house that my mother gave me when I decided to drop out of college and start my own business. Sale of cleaning products and supplies. I got off to a good start, being the only specialized store in my area, but with that I began to face something horrible, unbearable, something that no one in the world should bear… customer service. Seriously, just how stupid can people be towards salespeople? Good much! Despite that, I continued and with the help of my uncle's advice I learned how to manage my business, keep accounts and manage suppliers. Everything seemed to be going well. But one day, the fire nation attacked… nah, that would have been easier to fight. This damn virus appeared spreading on the other continent. I admit that I ignored this thinking that, being on the other side of the world, the virus would not arrive. A few months later, the first cases were registered in the north of the continent. Things started to get tense, but people thought "We are in Latin America, nobody comes here." Which turned out to be true for a while, for 2 months. As soon as the first cases of infection appeared, the fortieth was put into effect. Mandatory use of masks, bring alcohol to disinfect and all those rules that you should know. The hard part was for businesses that were forced to reduce their customer capacity in establishments. Many restaurants, bars and cafes have since closed. Many had to adapt and lay off employees, so the lack of work increased considerably. Me? I sold everything I needed to meet the rules of the forties, and I honestly like serving customers from the front door out. The latter is due to the fact that my store is currently small and entering closed places is not allowed. However, I am not on a bed of roses either, getting merchandise became very difficult, especially since my province depends on others for everything. You even get to collect money and travel to search for merchandise, going through the pertinent checkups and health papers. Fortunately, the vaccines began to arrive. I and my whole family get vaccinated with the first and second doses. Thanks to that the normals of the forties have been smoothed out. Enough to be able to celebrate Christmas with the family! No more WhatsApp tables, no more video calls or sending photos. We will meet to celebrate Christmas as it should be done! Then came the problem. My family decided to throw the house out the window after not meeting for so long. With the purchase of products, paying the bills and helping my mother from time to time; my wallet was almost empty. I had to get money to help with the celebration and buy some gifts, even small gifts. During the first week of December, sales were down, so he would have to seek income in some other way. Another job is not an option, I am alone with my business and if I ask my family for help they will be suspicious. December 8th arrived and as is the tradition here, I started putting up the Christmas decorations. Nothing big or flashy. Just a few garlands and lights here and there, plus a small plastic tree with little decorations in a corner of the house. Then put up a sign in front to inform customers. “Day 12/24, open only in the morning. Day 25, closed. " “Day 12/31, open only in the morning. 01/01, closed. " If you ask me, this is common sense to most people. But there is never a shortage of idiots who do not respect schedules and believe that you come into the world just to serve them. "Isn't it an obvious thing?" A voice said behind me, I recognized that voice. There he was. Andre. Andre is a boy my own age, a former college classmate. He is a blond boy with soft pink skin like that of a baby. Andre certainly looks younger at 1.68 meters tall of him. I was not happy to see him. He is a frequent customer, quite arrogant and vindictive. During our time in college, I found out that Andre still uses aderoos even though we were young adults. I gave him wedgies every week, sometimes up to 3 times in the same week, making him scream and showing off his embarrassing childish underwear. There were even days when he wore panties! I still usually laugh remembering those things, as well as looking at the photos currently stored on my computer. On my last day of college I gave Andre a big goodbye thinking that we would not see each other again. I gave his an atomic wedgie in his Hello Kitty panties and hung his up on the fence. I left there listening to other people's laughter, determined to start my own way out of college. About 2 months after I started my business, curiously in December 2019, he appeared in my store. He was one of my most uncomfortable clients. He was taking his time, talking and talking with a smug look, probably feeling like my boss or something. Repeatedly mentioning our time in college wanting to make me feel bad or something. I admit that I was not the best of men, but damn! He wears underoos and panties! He was only missing a sign that says' Give me a wedgie! Please!' After that first meeting he started showing up at least once a week. I learned quickly to ignore the bullshit of customers, but Andre was a special case. Even when the pandemic hit, he kept coming, only this time half of his face was covered by masks from various anime. I mean, I like anime and video games, but I don't want them covering my mouth. "Well, some people believe that workers are machines with no right to rest." I answered him and then go back to my store and put the plastic chain to prevent people from passing. Andre approached with a smile, it was evident despite the Dragon Ball mask on him. And what nice plans do you have for this Christmas? A trip taking advantage of the fact that they allow travel between provinces or perhaps going to a secluded place like a cabin? " I had no money for anything like that and he knows it, at least he imagines it to be so. “I will be reunited with my family. You know, no more video calls, some physical contact. " I replied. "What do you want to buy?" "I want a shower curtain, that one, the one with owls and hearts." He says pointing to the best-selling design. "And in those contacts ... do you intend to give someone wedgies?" Andre asked maliciously. "It would be more sensible to fight for the Falklands again, armed with a spoon." I responded by taking the curtains that he wants. "Do you need a bag?" I didn't ask him if he wants anything more, he preferred that he leave. "Ow What is it? You're usually not that sharp. Problems with the manager? " He joked knowing perfectly well that it is my store. "Or maybe ... an economic problem?" My disgusted reaction must have gone through my mask, because Andre laughed like a child who just discovered a secret. "If I ever find out how you do it, I will report you for harassment." I can't understand how he always seems to know when something happens to me. He can't really be watching over me… can he? Andre didn't stop smiling, pulling out a thousand peso bill and paying. "Bag, if you are so kind." I put the shower curtain on a plastic ball and handed him his change. “Don't worry, surely the solution will come to you as soon as you least expect it. Ta da. " He said goodbye, happier than usual, you can tell by the way he moves his hips. Ignore that and continue serving clients, checking things on my phone every now and then, and working lunch. The morning passed fast and boring until finally it was time to close for lunch and then the 3 hour break to open for the afternoon. After I had some pasta and sauce for lunch, I sat down at the computer to check the sites I frequent to see if anyone had posted anything interesting. The rest of the day was as usual. I served customers at my store door, scold some for not wearing their masks on their faces, and spray ethyl alcohol on prevention money. Finally night came, when I closed my shop and started making hamburgers when that happened. A private message arrived on my Facebook, but the user appeared as 'Secret Santa' with a picture of a cartoonish reindeer as a profile image. "Now what?" I said to myself and then proceeded to read the message. "Good evening, dear Nicolas. I am writing this message because I found out about your recent financial distress. I have a proposal that might interest you! If I accept, I am wonderfully sure that it will solve your problems! " I started to write my answer. Damn you, Andre. I'm not in the mood for jokes!" He almost immediately answered me. "How did you know it was me!?" Along with a surprised face emoji. "You are the only adult around me who says things like 'Wonderfully safe', you said it a lot in college ... I correct, not even children talk like that." Was my answer. "Well, there goes the allure of the mystery, thanks for ruining it." Accompanied by 3 disappointed face emojis. Block the user and report him as a stalker. --- But that was not the end. Andre came in person to my store the next day. "It's rude to block someone when he's trying to help you." "I also reported you as a stalker." I told him bluntly. "I don't have the time for your Christmas shenanigans." He crossed his arms with an annoyed and rather childish look. "Who said something about mischief? I was being serious. " "I will not have sex with you." Andre blushed as much as a Christmas ornament. "I didn't want to propose something like that to you!" He was breathing hard through his nose, it showed despite the mask. "I want to give you back the things you did to me in college and I am willing to pay for it if necessary!" I rolled my eyes hearing him. “Couldn't you use that money for something else? How to buy more mature underwear now that you are close to 23? Just say. But if you are obsessed with that fetish of yours, you will surely find someone on Alem avenue willing to do it. " "If it's not you, it won't make sense." Andre said and then took a piece of paper out of his pocket and held it out to me. “Look, here's my first offer and my private number. Just think about it and you are free to ask what you want without the need to accept. " I sighed tired of this. Better to finish that there before any customers came. "Keep up your wet dreams." I said while taking the paper. "You can go now?" "I'm going!" Andre turned and started walking, 5 steps later, he turned again and came back. "But before I go, I want a stain remover for colored clothes." I literally slapped the palm of my hand on my face. Since when did you get into a cartoon or a comedy story? Customers started pouring in, so I just crumpled up the paper and dumped it in the little trash can I have at the store. --- The days went by faster than usual and sales weren't improving. I was close to the due date to give my share of the money for the Christmas celebration and I only had a third of the total amount, not to mention the lack of presents. Look at the business container, I hardly ever dump anything in there so I knew that was still there. "Hmpm. Surely he wrote some nonsense like: You fell for the prank! Haha!" I hadn't even bothered to read the paper. The paper was practically all the way up, I took it and sprayed some alcohol. So I opened the paper, I saw Andre's phone number and… “… This must be a joke…” I'll just say that the amount he offers me has 4 digits. With that money he could pay and get a few gifts ... Spend the rest of the day thinking about this. It's quite a bit of money, but my pride was stopping me in the first place. And secondly, it's Andre, he was obsessed with his childish revenge. What if he does something that really hurts me? When night came I finally decided to text Andre with the number he sent me. Not that he can achieve much this way. "Hey… Andre?" I put the phone on the table and reached for a drink in my fridge, shit, hearing my phone ring all of a sudden almost made me jump. "Can not be…" Yes, Andre answered almost immediately. "Good evening I was waiting for your message" I wondered whether to continue for a few moments. “Let's get straight to the point. What do you want from me?" He took a few moments to write. “I just want to buy your time and give you back some of everything you gave me in college. In a private place, obviously. Knowing that I have done it is more than enough for me. " Then he sent a sticker of a cat winking. I don't know if I was more surprised by his frankness or his careless attitude towards this childish request. "Do you want to pay to let me make wedgies?" Andre was quick to reply. "Well, to be honest, I hope it's several wedgies, down to 3 underwear of my choice." "I won't even wear panties in your dreams." "Hahaha! It's a funny thought, but I'm not interested in that. " Andre took his time writing again, I think he wrote and erased on more than one occasion. “The deal is as follows. You come to my apartment at night, where I will be giving you several wedgies. Once 3 briefs are torn, you are free to go with the money and do whatever you want. " I rubbed my forehead, this is by far the most ridiculous treatment I have ever heard. "Why do you want to rip underwear?" "Hey! Do you know how many of my cute underoos and panties you screwed up !? ” He wrote accompanied by 3 emojis fuming from his nose. "I will not accept less than that!" I sighed as he looked at the messages. “We will be alone in the department. No photos or cameras of any kind. If you try to do something else, I'll go away. " “I was thinking about that. And it's fair, you can even take the money. " Andre replied. "I'm not going to do anything you don't want to do besides wedgies." I felt there was something more to those words. The conversation went on for almost an hour, talking about conditions and details on how to do this. We agreed to meet on Sunday, taking advantage of the fact that my store does not open at that time. Something quite common here. --- The days passed quickly again and finally the day of the meeting arrived. After closing the shop, I had a light lunch and took a shower. When I finished I dressed in dark blue pants and a black shirt with a pocket on the left side of the chest. I put on my mask, collected my wallet, sanitizer, and bus card. I left the house and took a bus to get to Andres's apartment, which happened to be in the center. It was very easy to recognize it, I have been there countless times. The building maintains a formal aesthetic, with 7 floors of apartments with small terraces. Several of them with air conditioners running to combat the heat. Upon entering, I had to spray my hands with alcohol and sign the guestbook and then take the elevator. According to the indications, Andre's apartment is on the top floor. I barely walked a few steps out of the elevator and found myself in front of the door of said apartment. "In the end I'm here ..." I said to myself and then knocked on the door. In less than 5 seconds the door was fully opened. "Welcome Nicolas!" Shameless Andre said. Why is he shameless? He was wearing a purple thong, an open bathrobe, and slippers. "What would you have done if it wasn't me who knocked on the door?" I asked trying not to look too much at his semi-naked body. "I left everything free for today, not even my parents will come today." He said as he stepped aside allowing me to enter the apartment. "Why would your parents come?" I asked him as he entered. The apartment is bigger than I imagined, well furnished and decorated without having to point out the Christmas decorations. This was one of the large apartments, therefore one of the most expensive. "Oh, they come every now and then. They are the owners of the building, so there are inspections from time to time to check for problems or if the tenants caused any damage. " Andre said closing the door and walking through the apartment. "That explains a lot of things." I said staying standing. He saw me for a moment, but he came back and served us both drinks. "Something to drink?" He offered me a glass of coke. I accepted it and drank. "Did you have a good trip?" "We could say that, it's a bus, you can't ask for much." I responded without much encouragement. "Do you mind if we start with this? I don't want to come home too late. " "You always go straight to the point, like in college, you go straight for my underwear and you pull on it." Andre said with a slight smile. "As you wish, give me a moment ..." Andre walked up to what I suppose was his room and a few moments later he returned with a wad of bills. He even showed the banknotes to show that there is no trick or deception. ‘Trust what you can see, not promises in the air’ was one of the phrases used by one of our professors at the university. "Fine ... let's just finish this ..." I said starting to undress. Andre wanted us to do this in underwear, adding more to the original sum to get it. Not that I even mind being naked with other men, I have nothing to embarrass me. At least not yet. Andre watched me, standing in my striped boxer briefs. "You're single, right?" He asked pulling out a box. "You should know, Mr. Stalker." I responded by taking off my boxer and leaving it with the rest of my clothes, being completely naked. "Harassment sounds so bad ... I call it follow-up." Andre said opening the box. "Choose the one you like the most, even if you end up using all of them in the same way." Inside the box were 3 underoos that he had gotten for me. All colorful with drawings of Paw Patrol, Pokémon and PJMask. I think the worst is the puppies. I decided to start with the worst, so I took the Paw Patrol underoos, sliding them down my legs, they adjusted to my crotch and butt in such a way that it was almost a natural wedgie. "There weren't for big men?" "It's not like I know your measurements, I had to guess." Andre said with a shrug. "Now, if you don't mind, let's move to the couch." "There are so many ways that sounds bad." I walked to the couch, not to sit, but to lean into it. Resting my bare chest there and sticking my butt out slightly. I swear Andre was staring at me and etching my image on his retinas. Then it started, I felt his little hands take control of the underoos' waist and pulling them up with force. "Ghhgh." I clenched my teeth to hold on, I wouldn't give him the satisfaction of screaming as easily as he did in college. "You are not funny." He complained childishly, letting go of the underoos and then pulling again in the same way. The second pull came higher. Likewise, the fabric got deeper between my cheeks and compressed my crotch. I had received some wedgies when I was younger, I am no stranger to them, but I had forgotten the uncomfortable feeling of the fabric invading my ass. Pull, release and pull again. Andre repeated the process while I tried my best not to react the way he wanted, letting out grunts but not screaming. In the midst of this I realized something important. Andre is not very strong, so tearing the underwear would take time. .That's how it went. Andre gave me about a dozen wedgies before the fabric started to rustle slightly, poking little holes in the underoos. "Let's go! Don't pretend to be made of stone! " Andre said frustrated. "Excuse me, princess. Maybe you want to spend some time in a gym instead of a nail salon. " I responded by giving him the biggest fucking smile I could do in that situation. “At least I don't have the nails of an ogre! You eat your nails, right? " “I don't eat my nails, I bite them and spit them out. It's different-eeeHH! " Andre took the opportunity to give me a wedgie. With my mouth open, I couldn't help but groan out loud as the fabric of the underoos ripped into a huge hole. I got up and turned to see Andre with a serious look, he had a satisfied smile. "That was dirty." I told him as I scooped the fabric scraps off my ass, pulling the useless underoos to the ground. "I had to get it somehow." He said still smiling. I gave Andre a bad look, but I turned to the box to take the next pair, which were PJMask's. “At least I don't scream like a girl. Did you know that many mistook you for a girl in college? " "My voice is not that feminine!" He protested. “It was not because of that, but because of wagging your wide waist when walking. Some girls were jealous of your inflated ass. " I said enjoying seeing him turn red. Andre closed and tied his robe to hide his hips from him. "Mhpm! Let's continue, now I want you to stand up. " He said with fire in his eyes. I stood with my arms crossed, trying to appear dignified with the underoos. My cheeks must have been red, because Andre was smiling. He came over to me, holding the front of my underwear. "Fuck you." I spoke in between before grunting when he started giving me a front wedgie. Now my butt was clenched in a new way and my crotch was pushed against me. Andre seemed quite happy to see me struggle to contain myself. "You remember? The first time you gave me one of this? " He said loosening to pull harder. “It was at a party, everyone was laughing at my mlp underoos. What did you do after that? " Hell, he remembered. Andre brought his hand to my rear, quickly stroking my ass and then grabbing the waist of the underoos. "Squeaky!" He loosened his grip on the front to pull from behind, burning my ass. "Gahhh!" I brought my hands to my crotch wanting to mitigate the pain. This is not functional. "I like it better that way!" Andre said excited like a child starting to play with his new favorite toy. "Do not stop! I want to hear more of that! " "Son of-Oow!" He had me in his hands now. "Eek! Gahhh! " My butt was still aching from the first round of wedgies, now my ass and crotch are going through a worse treatment. "Iyeeek!" It's official, the squeaky wedgie is the worst, with underwear being flossed. I could feel the underoos sinking deeper and deeper into my ass as they stretched. When I pulled from behind, the underoos reached up to my shoulder blades. While pulling forward the underoos reached my nipples. I think that only makes it worse, long underoos means long squeaky. The sound of the fabric breaking was a relief, eventually tearing. "Oowwww ..." I spread my legs and began to gently pull the fabric off my ass. He was surprised they hadn't fallen. The underoos looked like a colorful rope. "Oh yeah, I had to bring spare underwear to college to change in the bathrooms." Andre said with a smirk of complacency and pride. "I suppose your delicate skin could not bear to go to command." I said trying to be defiant. "Don't believe it, many of my pants are pleasant to the skin." He responded with a hand on his hip. "But when you have something good, you have to use it." I rolled my eyes as I finished taking off my ruined underwear, throwing it aside along with the other underoos. I rubbed my sore butt and crotch not caring if someone else saw me. "H-hey! We must move on! " Andre said looking nervous. I frowned. "Could you at least let me have a drink." "Just put your underwear on first." He said looking away. I sighed and put on the Pokémon underoos, which felt tighter. I approached the table serving more refreshment for me. I looked around the apartment, pausing for a moment at the door of, what I assume is, Andre's room. Then I went on and noticed the balcony door, a sliding glass door. "I love the view from the high places." Andre said suddenly, he must have noticed my gaze on the balcony. "People rarely look up high enough to see my balcony, so sometimes I forget to close the door." "Nor is there a place to look inward or even the balcony itself." I said thinking about the angles from outside. We had a little chat before continuing with the wedgies. As soon as the underoos are ripped, I'll be free to go with the money. --- "Aaah! My ass is going to split in two!" I screamed as pain hit my ass in places I'm embarrassed to mention. "Hold on! We are in the third briefs!" Andre said pulling hard. And that's how it ends like this. Andre was pulling hard at the deep-sinking underoos, with no signs of wear. Sometimes he would leave the back and pull on the sides "When will these ridiculous briefs be ripped !?" The wedgies lasted longer than the other 2 put together. My ass is on fire right now. "Hahaha! The good quality is noticeable, right? " Andre said pulling again on the back reaching my neck. "Gaaahhhhh!" Then I got it. Andre bought the better quality more ‘mature’ underoos, knowing that I would pick these for last, when the pain was piling up. "You know what is about to happen, right?" Andre said in a singsong voice. Yes, I could see it, the material stretching over my head. "Atomic wedgie!" "TEEEK!" His waist hooked onto my forehead, pulling my head back. Trying to move my head increases the pain in my butt, so I try not to move. "Finished?" Ask through clenched teeth. "I'm afraid the deal says the underoos must be torn apart, so enjoy your new hat." Andre said and hit me on my exposed butt. I staggered forward, knees pulled in. Then I felt him turn and push me. The sensation on my skin told me that he was pressed against the glass door. "You remember? What you did to me the last day… ”Andre spoke to me, very closely. “That must have been the worst wedgie you gave me and the most humiliating of all. Even now the guys in college laugh at me. " He smiles cheekily with a twinkle in his eyes .. "How does it feel to be in my place? Just by opening the door, the world could see you in your shameful situation. " "..." I looked into his eyes. "When the underoos break ... I'm free to go and do anything right?" I said as clearly as possible. This seemed to confuse Andre. "Huh, yeah, that's correct." "Excellent." So I pushed Andre off making him fall on his ass to the ground. I brought my hands back taking the outstretched underoos, took a deep breath and pulled hard. "ARRRGHHH!" It hurt like hell. But I was rewarded by the heavenly sound of the fabric tearing and the pressure releasing. I removed the cloth they had on my forehead and the remains of the underoos. Andre stayed on the ground watching. "Cheater ... I should have added a rule so you couldn't do that." Despite his complaint he was smiling. “Oh well, it was still a lot of fun. I guess now you want to get dressed, take the money and- " I interrupted him holding his robe with both hands. "Actually, I was thinking of something else, a trip to the old days!" He seemed to understand what he meant because his face turned red. "After all, I am free to do what I want now and go." I played with the words, the order of things does not affect what we did. I effortlessly pulled Andre's robe off leaving his female body exposed, as well as something else exposed. His thong was bulging and there was a stain on the bulge. It seems Andre was enjoying this too much. He tried to say something, but he was clearly too embarrassed to speak. "YEEEEEEEK!" Though a feminine squeak came out smoothly when he pulled the sides of his thong, lifting him off the ground. He covered his crotch to hide his erection. "Now it's my turn to have fun." I pulled on his thong and took the opportunity to bring it up to his shoulders. Now it looked like one of those cheeky V-shaped swimsuits that leave nothing to the imagination. "GAAHHH~" His squeal sounded more like a moan now. "Y-are you done?" I was far from done. "That is your room, right?" I said pointing to the door from earlier with a mischievous smile. "With your clothes, including your underwear, correct?" Andre's face turned completely "You wouldn't dare!" I dragged Andre into his room, which had a lot of childish and feminine things, there was even a skirt on a chair in front of a desk. But I concentrated on the cabinet where he keeps his clothes, opening the drawers until I found the gold ore. "I see you haven't changed at all all these years." I said looking at various pairs of underoos, thongs and panties. "Maybe I have to spend the night, it doesn't bother you, does it? Andre squealed softly, I don't know if he was worried or excited. But later, during wedgies, his excitement was on display.