Long Embarrassing Underwear Story

So last summer I went to my cousins' house. My parents were out of town for 3 weeks so I was staying there with my 2 cousins (both boys aged 14 & 16), uncle, and aunt. At this time I was 15. Before the story starts, let me tell you that these 3 weeks just went wrong for me... but I still had a good time at their house... sort of... Well the day before I left my mom said "Make sure that you have enough clothes for the trip!" I thought to myself "Of course I have enough." The next day about 30 minutes before I was supposed to leave I started to pack (I know, stupid idea). My parents had already left for their flight, and my uncle and aunt were going to come pick me up and drive me 6 hours to their house. Oh, and we had to be there at 7:00 for a party, and they were coming at 1:00. So it's 12:40 now and I have everything packed except my underwear and socks. I pack up my socks and then I open my underwear drawer... Only to find an empty drawer waiting for me!!! I run to the hamper, but it is bare too! I then run down into the room where we do our laundry... But my clothes are no where to be seen!!! At this point I have no idea where any of my underwear is. I had only one pair of underwear, and they were white boxerbriefs that were kind of tiny on me (so tiny that at first glance they look like tighty whities). I had been wearing those for a day, so I took them off and put them in the hamper. I then get a call from my aunt telling me how my uncle isn't driving down to get me, just her. And that she was going to be there in about 5 minutes. After that I called my mom and asked her where all my underwear and other clothes were. She told me that she gave them to a friend to wash them while we were away (don't ask me why, my family is screwy).So now I go back upstairs. I have enough of everything, except underwear. Then I hear the doorbell ring. I lock up the house and just get in the car with my bag. About 20 minutes into the drive she asks me if everything is alright. I tell her my issue with underwear, so she pulls into a Walmart. She asks for my waist size and I tell her. She tells me that she will be right back and that she is going to buy me underwear. A little back story on my aunt, uncle, and cousins. My aunt and uncle are really cheap. They buy the cheapest thing they can find. They bought my cousins cheap embarrassing clothes, so now they buy their own. So before she goes in I tell her "Can you look for something that is my style?" and she replied with "Oh sure sure." About 10 minutes later she comes out with 4 sets of 6 underwear. We start driving off. About 2 hours later of talking and driving she asks "Are you wearing some undies right now?" to which I replied with "No, I'm not." So she told me to just go in the back seat and put on one of the pairs that she bought. Up until now, I hadn't seen the underwear. I pull the first bag of 6 out... AND THEY ARE SUPERHERO UNDIES!!! I'm talking little boy briefs with Superman, Batman, Spiderman, etc. on them!!! I say "Aunt Kelly, these are underwear for little kids!" Then she said "They were 10$ for 4 bags for your size. So I bought them. The other ones were 10$ per package, so I decided to just get these. Try them on to see if they fit Jacob." Reluctantly, I pull out some Superman white, red, and blue briefs. I slip them on hoping that they are too small for me... No such luck. They are a little tight, but they stretch. We pull up to a red light just as I get them on, so she turns around and gets a full blown view of me sitting in the underwear. I try to cover up, but it's too late. "Well don't you look cute in those. You should check the other ones." I pull out the second bag... And trust me, It got worse. More little boy briefs with TEENAGE MUTANT NINJA TURTLES. I couldn't believe my eyes, until I pulled out the third one... THOMAS THE TRAIN. Then I pull out the last one, hoping that it is just plain underwear. No such luck... BEN 10. I was beyond disbelief. BEYOND. Well we finally arrive at the house, and I get out, just in time to say hello to my cousins and my uncle before the party started. I never felt so awkward in my life. I don't wear briefs ever, I only wear boxerbriefs. So the party went all right, nothing really happened. The next day, in the morning, I woke up to find my 14 year old cousin, Chris, waiting in the kitchen. My aunt and uncle had already gone to work, and it was just me and him awake. We decided we were going to prank Andy, my other cousin. (My cousins and I are kind of close, so we always like to play pranks on eachother, but the fact that I was in little kid undies for 2 weeks didn't make me feel better). We snuck into Andy's bedroom to find him lying above the covers in just his sweat pants and a short black t-shirt. We looked closely to see that the top part of his underwear was showing... Hanes tighty whities! We both almost busted up laughing because Andy always boasts about how he wear boxers. So we slowly walk up to him, and ever so slowly pull down his sweat pants while he is asleep. We take them off and put them on the floor next to his bed to make it look like they came off in the middle of the night. An hour later Andy still wasn't awake so we decided to wake him up by giving him a wedgie. We crept up on him, and got him really good. They went halfway up his back. He woke up and grabbed his pants as we fled the room. He ran out after us and he got Chris pinned on the ground. He started trying to rip off his pants... which he did successfully. Revealing his black briefs. Well that was the first day and nothing really happened. My aunt got home soon after, and she started talking to me about how the day was, and everything. Anyways, for the next few days I was cautious of everything. After the first week was over, Andy went to a camp for a week to help volunteer. So one day with just me and Chris home we decided to go swimming. We both wear our underwear in the pool. So after about an hour, without me noticing, the strings on my already loose bathing suit came undone. Before this Chris's bathing suit had already come down when he was getting out of the pool, so I had already had my little laugh at his underwear. Well, I decided to dive in. When I did my trunks went down to my ankles... BUT I DIDN'T NOTICE IT!!!! When I came up from under the water, Chris was laughing his butt off. He then said "Dude. Nice underoos." At first I was like "What?" Then he made a quick move behind me and grabbed my Spiderman undies! He gave them a tug, and since they were tight and stretchy, he got them up kind of far. I quickly picked out my wedgie and pulled my pants back up. I was so embarrassed! He would not let me live it down the whole rest of the time in the pool. He kept pantsing me and wedgying me. It was awful. And that night didn't get better. I fell asleep in my gym pants, and woke up in Ben 10 tighties. I was sooooo embarrassed for the whole rest of the trip. Well that's my story, and to this day he still harasses me about it! It's all good though because I don't really care about it anymore.. Just a little.
JacobR111 JacobR111
18-21, M
17 Responses Jul 8, 2011

I need undies, friends, I have no money plz no kid undies plz help I will give my address please Xbox message me my gt is :ES SHOTGUN LORD


i got a worse one a girl was having sex with me and then my penis went a little to far in and she was scerming oh **** **** get tthe hell out if was asaomme man

something like This Happened to me When I was 12 I was going to my grandma's for a week my mom said to make sure I had everything to take to my grandma's house I told her I would just wear the same thing the whole time because my grandma cleans clothes all day.(everyday) so my mom and dad left and I was home alone for a good 4 hours in like a hour I started packing Then my grandma called said my grandpa wasnt feeling good so it was just her. Then she said her washer and dryer was broke so bring extra clothes so I looked all around the house for clothes the only thing I was missing was the most important thing underwear I had only one pair (red boxer briefs) and I had then on for a day so I took them off and put them in the washer at my house my grandma called again said she was 40 min in I told her ok and started looking for more underwear Then my mom called said she took all the clothes with her to donate them to goodwill (my mom always donates) she said she was going spring clothes shopping when she got back I told her ok and then my grandma pulled in I grabbed my clothes and got in.She asked how things were I told her I had no underwear so She pulled into Walmart and she said she would buy me some I told her my waist size and she went in and came out and she asked if I had any underwear on I told her no and she gave me the bag and told me to go in the back and put them on then I took out the first bag I looked very hard at them and told her they were for little kids (they were Ben 10 briefs) She said they were one out of 3 that fit me so I looked at the other ones and she had plain white briefs and camo briefs So I went with the camo (I refuse to where tighty whiteys) so we got to my g-ma's house she told me to go unpack when I got inside I could not breath my 3 cousins where there Andrew (13) Caleb (12) and Hunter (13) I was so scared cuz I thought they would go through my stuff and see the briefs my g-ma bought so that morning my g-ma was visiting my g-pa in the hospital for 3 hours so I woke up went down stairs and saw my cousins Hunter and Caleb so we knew that during weekends Andrew sleeps in till 12:00 so We decided to do somthing funny to Andrew. my cousins always pull pranks on me and each other but the fact that I was wearing camo briefs I was not comfortable . we sneaked in his room and pulled the sheets off and he only had his underwear on (priceless) he always said he only wears boxer briefs but we now know he lied so we got all his clothes exept his briefs and put them in the washer and when he woke up he yelled for us to bring him his clothes now we told him they were being washed so he came down in his white briefs and we laughed so hard then he looked in the washer and took out his clothes Hunter took them from him and threw them outside (you think they were wet they weren't)and Andrew ran outside to grab them then our Neighbors dog Sweetie grabbed his clothes by his mouth and took them to his dog house and and he was locked outside in his white briefs we died laughing. So eventually we let him back inside and he got his clothes back from Sweetie and he chased us all to pants us he did to my cousins not me I out ran him but funny thing my other two cousins who say they wore boxer briefs were wearing briefs. anyway my grandma's dog Bentzly took the white and camo briefs that I had under my bed and tore them to shreds when I look at him he just shook his tail. So I was stuck in Ben 10 briefs all week but the last two days the worst thing happened I was jumping on the trampoline and my grandma had took my clothes to a laundry mat to get them clean so I had no other clothes except what I had on so I jumped off the trampoline and my shirt ripped off no big deal but then my cousins wanted to go fishing and I said why not but I really did not want to go because I was in Ben 10 briefs so I hopped my pants wouldn't become undone and fall down or the dog bites them and rips them off or my cousins pants me.So we got on the boat so far so good and then my cousin Andrew was told by My cousin Hunter that I was the one hat pranked him so he hooked his fishing rod on my shorts on pourpos and we in the middle of a large lake on the same boat so then he threw the line out and my pants went with it and I was so super embarrassed so then they tried to give me a wedgie and since they were stretchy they went all the way over my head but Still i am short so yeah they would go over my head and my cousins would not let me live through it . That night I got a call from my mom and she said she was going to be two weeks late so she told my g-ma to buy me more underwear the day my grandma wanted to go buy my underwear I got sick and was asleep the whole day but what I did not know was my cousins went WITH HER!!and bought the most embarrassing briefs ever Spongebob Briefs TightyWhiteys and ironically they bought new underwear too boxer briefs!!! and they gave me all their briefs(we had the same waist size) and I was so embarrassed and one night I went into my cousin Andrew's Room and stole his new pair and so in the morning if they pantsed me they had nothing to laugh at and so I had an even better plan I took my Spongebob briefs and Put it on them while they were sleeping (I didn't look at their areas) but in the morning I walked down stairs and I saw my cousin Andrew around the corner getting ready to pants me then I didnt care cuz I wasnt wearing Spongebob Briefs they were and I got down the stairs and my cousin pants me They were laughing but then I looked down and what was I wearing Tighty Whiteys that means they new I switched and I pulled their pants down what do you know the were wearing boxer briefs and once my mom heard my grandma bought me underwear she said she wouldn't buy me more

Please tell more stories. I like hearing them.

Sent me some stories

Today I was pantsed during pe class and my underwear fell to my ankles

your aunt sucks

You think thats embarrassing i am a 15 year old boy from Wigan in England and the same 4 boys in my school keep picking on me they push me around then onto the floor the one of them who is in year 11 the year above me sat on my chest and put his knees on my biceps so i could not move my hands. then the other 3 took my shoes shirt blazer and pants and i could not do anything because i was pinned to the floor and it was 4 vs 1 and i am not strong im a little skinny. After around 10 mins of them keeping me there with 1 of them sat on my chest 1 keeping hold of my legs and another keeping me in a head lock an audiance began to gather round us laughing at me and filming it. then they turned me flat onto my stomach facing the floor as 2 of them pulled on my black mckenzie boxer briefs giving me a painful wedgie. they then let go of my boxers and stood me up holdind my hands behind my back facing the crowd another 1 of the gang walked over to me and **** flicked me then kicked my in the balls extremly hard. i shouted in pain the crowd laughed the boy let go of my arms and i fell to the floor feeling sick i looked up after about 1 min and the gang was gone but so were my clothes. As i stood up a boy in my year came up to me and told me the gang had put my clothes in the sportshall on a basketball hoop.so i ran to the sportshall still only in my socks and boxerbriefs i could see my clothes in the hoop but i was not tall enough so i jumped up and streched my arm as far as i could and grabbed my shirt and shoes. i jumped again, but failed get grab my pants. then the bell rung for lessons to start so i put on my shirt incase any 1 came into the sportshall i went to jump again when the doors flung open and all the boys in my year started to flood in for pe (there was about 100 boys in my year) they all started to laugh and about 15 of them ran over to my and grabbed me in a headlock and flung me to the ground. this made the crown laugh harder and louder and they started to all chant babby leggs babby leggs it was because i have white thin hairlass leggs i think. then there was a loud whistle and the boys let me go and turned to see the pe teacher standing there smirking trying not to laugh at me "let him go and get sum bloody pants on babby leggs" he laughed and so did all the boys it was his way of been a "cool teacher" to take the mick out of the kids that the "cool" people diddnt like and at this moment in time that was me. i jumped up to the basket ball net and grabbed my pants and quickly put them on. eversince then i am the laughingstock of the school and i get debagged and wedgied aroun 3 times a day the i get ******** to my underwear about 3 times a week its so embarresing and its not just in school even my mates do it to me wen im out with them what shall i do ??? :(

life for a schoolboy in the UK must be h*ll... Oh well, it was for me too, here!

I was bullied all through school too and one kid almost tricked the female gym teacher into seeing me in my underwear and another pantsed me (everything) in the hallway in front of our school secratary so I know how you feel-but itll be fine

I was bullied all through school too and one kid almost tricked the female gym teacher into seeing me in my underwear and another pantsed me (everything) in the hallway in front of our school secratary so I know how you feel-but itll be fine

You should have taken some of your cousins less embarrassing undies to wear.

Well, I have do admit I still fit into the size 14-16 Juniors Dora Explorers.... LOL
Yeah, I still wear them too, and I'm (32)!!!!

why did you just not wear underwear? to not wear underwear would have felt SO AMAZING and you would have loved the feeling only being used to wearing briefs....

you must have liked not wearing uw for even a little bit while waiting for the briefs....

and you could have said I may be without underwear but at least I am not wearing cartoon briefs....

and you never would have had to worry about if they were too small or not.....

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Lucky I wish I played with my cousins like that! I usually just am the only one pulling pants down! Lol bu it's ecause I have anunderwear fetish and like discovering the types of underwear they were.. But why didn't you make fun of your cousins because they wear briefs too?

one time I was sleeping and my older sister pulled my pans down then I got my shirt on and forgot to put pans on and went to school when it was recass two girls called every one over and took my clothse of embarrassing!!!!!!!!!!!!!!

Hah i never worn tighty whities just boxers

my parents were really cheap to when i was 13 my mom bought me dora the explorer panties at that time about 30 percent of the time i went without underwear but my mom didnt like me doing that so i wore them to school and my friend who is a guy made me take them off to save me from embarrassment i told him what my mom bought me and he just told me to take them off

Yes. That is why he wanted you to take your panties off, to help you. LOL

Unlucky man that sounds pretty rough .

As I said, I had been wearing those for a day already, and about half of another day... And because I hate going commando. HATE IT. But looking back at it, I wish I would have gone commando.

if you had gone commando your cousin would have noticed u hadnt w orn underwear into the pull. He would've pantsed u still but ur junk wouuld be exposed instead of embarrassing underwear

why didn't you either one, just wear the same none-embarrassing undies for the trip (kinda gross but still) or not wear them?