Long Embarrassing Underwear StorySo 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 16-17, M 16 Responses 11 Jul 8, 2011