Underwear

Surprise Date

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I ended up meeting a Pakistani girl at place I won’t say because she told me her brothers would get mad at her. She was actually one inch taller than me even though she was a few years younger than me. She told me her name was Ayesha, but she then told me it might or might not be her real name because she didn’t know me well and was still afraid of her brothers. This was an intriguing introduction and I told her that I liked playing this spy game. She laughed at that! I then asked her if she would like to come to my place and she shook her head as if she was thinking about it and then said yes. We went to my place, but she kept insisting on taking back roads and side streets. I told her that this intrigue was exciting me and we finally got to my place. She looked up and down the street, kind of like she wanted to confirm she wasn’t being followed, and then she followed me in. We then sat down on my sofa. It was wide enough for three people and we each sat down on one of the arms so there was some space in between us. She asked me if I had ever dated a Pakistani girl and I said no, and she said that Pakistani girls really liked it when non-Pakistanis asked them out, but they felt that non-Pakistanis were afraid of the intrigue, but she did state that she liked that I was making a spy game out of it. She then told me that she had read a lot about erotic things, but had no experience at all in them. I took that as a hint and began to slide closer to her until I was next to her, while she remained in her position at the sofa arm, but was glad that I had moved closer. I did think she had a very beautiful face and was feeling excited by it. She also actually had large breasts. I did find her very attractive! She then told me that she had a lot of fantasies from reading erotica and if she could act one of them out with me. I smiled and said yes. She then asked me to stand up and take off everything except my underwear. I stood up and did as she asked and when I was finished she asked me to stand in front of her. Although I was excited, I wasn’t aroused, but she could see the outline of my thing. Actually, I am a little small though and it was just under two inches when I’m not aroused. She then told me that she had read that most men were about five inches when they were unaroused and looked at me like she wanted me to give her an explanation. I blushed and said that I was a little smaller than most men. She said four or maybe three inches would have been a little smaller, but that I was a lot smaller. I blushed and she asked if I agreed and I said yes, being totally embarrassed by this. She then said she had been wanting to give me a BJ, but she said I was too small for her to want to do that. She then reached to both sides of my underwear and pulled them down to just under my knees, exposing my small, unaroused organ to her as she continued to sit down on the sofa and I continued to stand in front of her. She then looked up at me and said it was too small for her to do anything, but asked if I had any suggestions on what we could do. She did continue to pull my underwear down to my ankles and then had me kick them off, and then looked back up at me like she was still waiting for my response. I didn’t have anything to say, so she continued and asked me what I had wanted when I brought her to my place. She did say that she wasn’t experienced, so that was why she had been thinking she would follow my lead, but she hadn’t expected I would be too small for her to do anything. She then told me to go get a ruler and then to bring her a drink on the way back. I was still naked, and I walked over to my drawer and got a ruler and then got to the fridge and shouted to ask her what she wanted. She said she needed something strong because of the disappointment. I gulped and reached in the back and poured her and me each a scotch. I brought the two glasses and then gave her the ruler. She took the ruler and put it on the couch and then she took both of the glasses and said she really needed them. She took a drink from one and then told me to move closer to her while she grabbed the ruler and put it next to my thing. She asked me to hold it out so she could measure it better and I did. It felt really embarrassing as she measured it and she said it was just under one and a half inches, not even the two inches she had hoped for. I think it might have shrunk a little more while I was in front of the cold refrigerator. She then put the ruler back down on the sofa, and then finished her first drink quickly and then she drank her second one while I was still standing in front of her. It took her about ten minutes to finish the second one and when she finally did, she sighed and asked if I had a broom. I walked over and got it and then came back and gave it to her. She did say that what I did have going for me was that I had said that I would act out erotica with her and asked if I would still do that. I was feeling embarrassed now, and guilty, and I said yes. She then told me to first explain to her what I expected to do with her with my small stub. I was embarrassed even more by that and continued to blush and just said I hadn’t thought it all the way through. She sighed again and then stood up herself. She was taller than me and since I had taken my shoes off, she was now about two inches taller than me. She grabbed my hand and walked me to my bedroom and brought the broom and the ruler in her other hand. I had a single bed and a few drawers and she put the ruler on the bed and leaned the broom against the bed also. She then said she wanted me to open all of my drawers so she could show me what was in them. It did feel a little invasive, but all I had in them was clothes, so we went through them pretty uneventfully. She then had me sit on the edge of the bed and she took off her blouse, leaving her bra on. My eyes widened at that since she really did have big breasts, but since I had already been so embarrassed, my thing didn’t get aroused. She looked at my thing and said, no response huh, don’t worry we’ll have to do something because of that later. She then pulled down her pants and then her panties, exposing her own private area. She then told me that she wanted me to give her a BJ and she wanted it to be good enough to make up for her disappointment. She then shoved it in my face and, although, I had never given a BJ before, I began to stick my tongue in and lick what I could. She kept saying she had never known something could be so small as I continued to lick her parts. It was about half an hour later and she said that I wasn’t turning her on that way either. She then sat down on the bed next to me and asked me to hand her the ruler. She then told me to lie over her thighs and she began to spank me and told me she was punishing me for expecting something from her even though I was so small. After about twenty spanks I was starting to wail, but she held me down with her other arm and continued to spank me telling me I should be more than embarrassed about my size. I was bawling loudly and my legs were kicking from the pain after that and then she got to fifty and she stopped. She then asked if I would apologize for expecting something from her even though I was so small and I said yes between cries. She then said she had one more thing and she told me to lie on my back. My bottom was still sore, but I did. She then told me to spread my legs and lift my waist up. I did and she got on the bed between my legs and took of her bra. Her breasts were HUGE when they poured out of her bra. I really wondered how they had been contained in the bra, as they must have been compressed in the bra. She then grabbed the broom and squeezed it between her legs, holding it there with them. It actually looked like a foot long cock, the way she was holding it. She then said that she was going to do to me what she had been hoping I would have done to her and she told me to grab the top of the broom handle and to push it into my own bottom hole. I reluctantly put the tip of the broom handle on my hole, but it didn’t seem to go in. She continued to hold it between her legs and began to gently slide it in as she climbed on top of me. Now her breasts were just below my face and she said I could suck them while I pulled the broom handle into my hole. I pulled the broom, as she pushed it in herself, while I sucked her HUGE breasts. When I got the tip of the broom handle in, she said I could grab her breasts, while I sucked them. Meanwhile, she continued to thrust the broom handle into my hole and began to move it in and out. I really enjoyed sucking her breasts, even though having the broom handle inside me was a slightly painful experience. She continued thrusting me for about an hour, and then my own penis started to get erect from the thrusting as well as the feasting on her HUGE breasts. About ten minutes after that, I ejaculated and she laughed and said, well, it looks like we’re done now aren’t we as she touched my nose with her finger. She then began to slowly pull out the broom handle and began to cuddle with me. I did feel that some blood came out when she pulled out the broom handle, and the handle was covered with, well number 2 stuff. We then cuddled for a while after that and she actually said she enjoyed that and looked forward to us doing it again frequently. I said that I looked forward to that also.

 

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Wrestling Mishap

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My neighbor, a 35 year old lady had asked me to watch her kids, a 15 year old girl and a 13 year old boy. I am 23, but am unemployed, yet I was able to practically get a steal in getting a cheap house among a bunch of well off ones. I’ll let you figure out how I did that, but it did involve some creativity and inside scoops. Anyway, the lady was a bit of a fitness buff and I practically always saw her in shorts, which showed off her toned legs, as well as a tank top, which showed the top of her cleavage as well as her arms. She was my height and always seemed like a friendly lady. Today, she brought her kids and asked me to watch them for a while. She didn’t even offer me babysitting money, but she was asking it more like a neighborly gesture. Since she was a friendly lady, I said okay. The kids came in and she left. The kids were dressed similar to their mom, in tank tops and shorts. The fifteen year old girl, Gina, was tall enough to be up to my forehead, and the thirteen year old, Greg, was up to my chin. I normally don’t wear shorts, so I was dressed in a t shirt and pants. Greg asked if I had any video games, and I did have some older ones, and, although I could tell he was a little disappointed, he turned it on and began playing. I thought that was easy, now I had to figure out what to do with Gina, and then I could have them keep themselves busy until their mom came, although she hadn’t said how long that would be. Gina was still standing in front of me, while I had been thinking about something for her to do, and she said that I looked like I was daydreaming, which I might have been as I was thinking of an activity. She said she really wasn’t into video games like her brother, and then asked me if I daydreamed a lot. I said no and she said it was okay if I did and I didn’t respond to that. She then asked if I was into any sports, which made me guess she might be as athletic as her mom. I said I really wasn’t. She said her favorite sport was wrestling and asked if she could show me some of her favorite moves. I told her I didn’t have padding on the ground, but only had a carpeted floor. She said she would just go through the motions, so nobody would get hurt. She then told me that in real wrestling, one person gets on their hands and knees while the other person grabs both arms of the first person. She motioned for me to get on my hands and knees and she grabbed my arms. She then said Begin, and pulled my arms and twisted me until I was on my back and then put her knees on my shoulders. I must say that I did feel a little excited by all that. She then told me we could switch positions and she would be on her hands and knees while I grabbed her arms. She said Begin and she ended up twisting herself and then putting me on my back and putting her knees on my shoulders to pin me again. She then said I wasn’t much of a fighter, but then said I might do better if I put some shorts and a tank top on and got off me and nudged me to go to my room and change into those types of clothes. I went into my room and saw that I really didn’t have a lot of shorts, but I had one very small swim suit but I also didn’t have a tank top, so I left my t-shirt on and then opened the door. She did say that she liked my shorts, but said that my t-shirt was too lose and was hindering my wrestling. I then said I didn’t have a tank top and she said I might wrestle better if I took off my t-shirt. She also said that might actually give me an advantage because it would be harder for her to grab my skin than it was to grab my shirt as she giggled. I took off my t-shirt and then she suggested that it might be better if we wrestled on top of my bed since it was softer than the floor. I agreed and got on my bed in the hands and knees position. She told me that since I now had the shirtless advantage that she would have to wrestle a little harder since she couldn’t get a grip any more. Since the bedroom door was still open, we could hear Greg still playing the video games. She then got on the bed and grabbed my arms and she said Begin and she ended up pinning me again, but this time she elbowed me in the ribs when she did. Nevertheless, as she had me pinned, she then asked me if it felt embarrassing getting beat by a girl. I was still looking up at her and said it was a little embarrassing, but then I said she was an athlete and I wasn’t. She then got off me and asked if I was even trying. I said I would try harder, and then she got on her hands and knees and I got on top, grabbing her arms and she said, Begin, and she then went backwards and grabbed my legs. She then put me into what is called a figure four in wrestling, which pulled my leg muscles and mad them feel strained. I was trying to shake my legs to get out of it and then I ripped my swim suit shorts. Good thing I had underwear, but she didn’t let go with her legs, but rolled us both over so we were both on our stomachs. She then began to pull herself up, which made my legs hurt a lot more. It also had the effect of ripping my underwear. I was yelling for her to stop, both from the pain and also from the embarrassment of everything now being ripped. Just then I heard the doorbell, and then I heard Greg answer the door while Gina was still holding me in the figure four with everything ripped. Greg and his mom then came into the bedroom and Gina told her mom that I was a good enough host to learn wrestling from her. Their mom then said I wasn’t much of an athlete and told Gina to let me know. She gave one more pull on my legs, completely ripping my underwear and also giving my legs two Charlie horses, and then let go and got off the bed. Their mom then said it looked like Gina and Greg had fun and said she’d be dropping them off more frequently now and as I got up, I realized that everything had ripped off and I was naked. Of course, that meant that Gina, Greg and their mom saw my manhood, and I am a little small. They all laughed, and Greg blurted out, Well now we know why he’s not athletic. Gina giggled, but their mom tried to keep her own laugh in. I grabbed the bed cover to cover myself, while at the same time, Greg pulled down his own pants and underwear and showed his sister and mom that his manhood was bigger than mine. Gina kept laughing, but their mom tried to jump to my defense and said mine was smaller because I had just been exhausting myself and that she was sure it was bigger when I wasn’t exhausted from wrestling. Greg pulled his underwear and shorts back up and both he and Gina had a puzzled look, but seemed to accept that explanation. (that wasn’t the reason though, I really am small down there). We all walked out to the door and I whispered to their mom, thanks for the explanation. She smirked and whispered back, you mean you’re that small all the time? And then began chuckling loudly as they left, and she also reminded me that she’d drop the kids off again soon.

 

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Ayesha

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I ended up meeting a Pakistani girl at place I won’t say because she told me her brothers would get mad at her. She was actually one inch taller than me even though she was a few years younger than me. She told me her name was Ayesha, but she then told me it might or might not be her real name because she didn’t know me well and was still afraid of her brothers. This was an intriguing introduction and I told her that I liked playing this spy game. She laughed at that! I then asked her if she would like to come to my place and she shook her head as if she was thinking about it and then said yes. We went to my place, but she kept insisting on taking back roads and side streets. I told her that this intrigue was exciting me and we finally got to my place. She looked up and down the street, kind of like she wanted to confirm she wasn’t being followed, and then she followed me in. We then sat down on my sofa. It was wide enough for three people and we each sat down on one of the arms so there was some space in between us. She asked me if I had ever dated a Pakistani girl and I said no, and she said that Pakistani girls really liked it when non-Pakistanis asked them out, but they felt that non-Pakistanis were afraid of the intrigue, but she did state that she liked that I was making a spy game out of it. She then told me that she had read a lot about erotic things, but had no experience at all in them. I took that as a hint and began to slide closer to her until I was next to her, while she remained in her position at the sofa arm, but was glad that I had moved closer. I did think she had a very beautiful face and was feeling excited by it. She also actually had large breasts. I did find her very attractive! She then told me that she had a lot of fantasies from reading erotica and if she could act one of them out with me. I smiled and said yes. She then asked me to stand up and take off everything except my underwear. I stood up and did as she asked and when I was finished she asked me to stand in front of her. Although I was excited, I wasn’t aroused, but she could see the outline of my thing. Actually, I am a little small though and it was just under two inches when I’m not aroused. She then told me that she had read that most men were about five inches when they were unaroused and looked at me like she wanted me to give her an explanation. I blushed and said that I was a little smaller than most men. She said four or maybe three inches would have been a little smaller, but that I was a lot smaller. I blushed and she asked if I agreed and I said yes, being totally embarrassed by this. She then said she had been wanting to give me a BJ, but she said I was too small for her to want to do that. She then reached to both sides of my underwear and pulled them down to just under my knees, exposing my small, unaroused organ to her as she continued to sit down on the sofa and I continued to stand in front of her. She then looked up at me and said it was too small for her to do anything, but asked if I had any suggestions on what we could do. She did continue to pull my underwear down to my ankles and then had me kick them off, and then looked back up at me like she was still waiting for my response. I didn’t have anything to say, so she continued and asked me what I had wanted when I brought her to my place. She did say that she wasn’t experienced, so that was why she had been thinking she would follow my lead, but she hadn’t expected I would be too small for her to do anything. She then told me to go get a ruler and then to bring her a drink on the way back. I was still naked, and I walked over to my drawer and got a ruler and then got to the fridge and shouted to ask her what she wanted. She said she needed something strong because of the disappointment. I gulped and reached in the back and poured her and me each a scotch. I brought the two glasses and then gave her the ruler. She took the ruler and put it on the couch and then she took both of the glasses and said she really needed them. She took a drink from one and then told me to move closer to her while she grabbed the ruler and put it next to my thing. She asked me to hold it out so she could measure it better and I did. It felt really embarrassing as she measured it and she said it was just under one and a half inches, not even the two inches she had hoped for. I think it might have shrunk a little more while I was in front of the cold refrigerator. She then put the ruler back down on the sofa, and then finished her first drink quickly and then she drank her second one while I was still standing in front of her. It took her about ten minutes to finish the second one and when she finally did, she sighed and asked if I had a broom. I walked over and got it and then came back and gave it to her. She did say that what I did have going for me was that I had said that I would act out erotica with her and asked if I would still do that. I was feeling embarrassed now, and guilty, and I said yes. She then told me to first explain to her what I expected to do with her with my small stub. I was embarrassed even more by that and continued to blush and just said I hadn’t thought it all the way through. She sighed again and then stood up herself. She was taller than me and since I had taken my shoes off, she was now about two inches taller than me. She grabbed my hand and walked me to my bedroom and brought the broom and the ruler in her other hand. I had a single bed and a few drawers and she put the ruler on the bed and leaned the broom against the bed also. She then said she wanted me to open all of my drawers so she could show me what was in them. It did feel a little invasive, but all I had in them was clothes, so we went through them pretty uneventfully. She then had me sit on the edge of the bed and she took off her blouse, leaving her bra on. My eyes widened at that since she really did have big breasts, but since I had already been so embarrassed, my thing didn’t get aroused. She looked at my thing and said, no response huh, don’t worry we’ll have to do something because of that later. She then pulled down her pants and then her panties, exposing her own private area. She then told me that she wanted me to give her a BJ and she wanted it to be good enough to make up for her disappointment. She then shoved it in my face and, although, I had never given a BJ before, I began to stick my tongue in and lick what I could. She kept saying she had never known something could be so small as I continued to lick her parts. It was about half an hour later and she said that I wasn’t turning her on that way either. She then sat down on the bed next to me and asked me to hand her the ruler. She then told me to lie over her thighs and she began to spank me and told me she was punishing me for expecting something from her even though I was so small. After about twenty spanks I was starting to wail, but she held me down with her other arm and continued to spank me telling me I should be more than embarrassed about my size. I was bawling loudly and my legs were kicking from the pain after that and then she got to fifty and she stopped. She then asked if I would apologize for expecting something from her even though I was so small and I said yes between cries. She then said she had one more thing and she told me to lie on my back. My bottom was still sore, but I did. She then told me to spread my legs and lift my waist up. I did and she got on the bed between my legs and took of her bra. Her breasts were HUGE when they poured out of her bra. I really wondered how they had been contained in the bra, as they must have been compressed in the bra. She then grabbed the broom and squeezed it between her legs, holding it there with them. It actually looked like a foot long cock, the way she was holding it. She then said that she was going to do to me what she had been hoping I would have done to her and she told me to grab the top of the broom handle and to push it into my own bottom hole. I reluctantly put the tip of the broom handle on my hole, but it didn’t seem to go in. She continued to hold it between her legs and began to gently slide it in as she climbed on top of me. Now her breasts were just below my face and she said I could suck them while I pulled the broom handle into my hole. I pulled the broom, as she pushed it in herself, while I sucked her HUGE breasts. When I got the tip of the broom handle in, she said I could grab her breasts, while I sucked them. Meanwhile, she continued to thrust the broom handle into my hole and began to move it in and out. I really enjoyed sucking her breasts, even though having the broom handle inside me was a slightly painful experience. She continued thrusting me for about an hour, and then my own penis started to get erect from the thrusting as well as the feasting on her HUGE breasts. About ten minutes after that, I ejaculated and she laughed and said, well, it looks like we’re done now aren’t we as she touched my nose with her finger. She then began to slowly pull out the broom handle and began to cuddle with me. I did feel that some blood came out when she pulled out the broom handle, and the handle was covered with, well number 2 stuff. We then cuddled for a while after that and she actually said she enjoyed that and looked forward to us doing it again frequently. I said that I looked forward to that also.

 

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Little Sister Embarrassed Me

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I was sixteen years old and I had to stay alone with my twelve year old sister and one of her guy friends also twelve as their baby sitter. Since it was about nine, I told my sister that it was time for her to send her friend home and for her to go to bed. My sister said, “No,” and I began to grab her by the hand to drag her to take her to her room and asked her friend to leave. Her friend decided to say he didn’t want to leave and then tackled me and knocked me to the floor by surprise. Then my sister began to hold me down while he unbuckled my belt and pulled down my pants and then my underpants leaving my thing exposed. Although I am taller than both of them, I have had a late development in puberty down there so I have a half inch penis when I’m not arouse. He laughed and so did my sister and then pulled down his own pants and underpants while I was still on the ground and showed me that his penis was about four inches long even though he wasn’t aroused. My sister then started teasing me about this, and he continued to as well and it was very embarrassing. She kept holding me down while he moved around and then began slapping my face with his penis. I didn’t know what to do, so all I said was that they could stay up late and he didn’t have to go. The then got off me and let me pull up my pants and then said that I should go to bed, but they’d wake me up when our parent got home. I was humiliated at being sent to bed by them, but they did get me up in time and I said they had been so well behaved. My sister still teases me about my size whenever our parent isn’t around. Particularly when we’re around people my age. It’s very embarrassing!

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Wedgie during gym class

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This story happened when I was in 6th grade. My day started out like no other. But when I went into my underwear drawer and I noticed that I only had Spider-Man tighty whites. And I had gym today so I had to get changed in front of everyone. But I thought the day wouldn’t be so bad. When I went to my first period, I heard some people quietly laughing at me. Soon I noticed that my undies were showing. But that wasn’t the end. One of the students from period 1 was in my gym class so he grabbed my undies and gave me a hanging wedgie. They also took pictures and sent it to some girls. What an embarrassing day 🙁

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Caught with my pants down at urinal

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So this happened when I was in preschool. One day at school I asked to go to the bathroom and the teacher said yes. When I walked into the bathroom, my friend was at a urinal with his pants and underwear down to his ankles. So I began to talk to him for a moment and everything was fine. The next day comes along and I ask to go to the bathroom again. Once I walked up to the urinal, I pulled my pants and underwear down to my ankles. A few seconds pass and some 6th graders saw my butt and underwear(the school goes up to 6th grade.) And to make matters worse, I was wearing Spider-Man briefs. After that I would get wedgies every day by those 10th graders. In fact one of them pantsed me in front of the whole school. I had to change schools because of that.

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Caught with my pants down

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So this happened when I was in fifth grade. At the end of every school year, the school would host this thing called Field Day for all the students.

 

When it was my class’ turn to file out onto the field, I needed to pee. Unfortunately we were passing through a hall of a lower grade (maybe first or second graders?) And when I went in the bathroom there was a small group of like 10 younger boys using the urinals and toilets.

 

Here’s where it started to go wrong: the toilets were occupied (and had longer lines so I couldn’t wait) and all the boys at the urinals were peeing with their pants ALL the way down. Even the ones waiting in line already had their pants and undies down!

 

Being the nervous wreck I was and wanting to fit in, I got in line, followed suite and pulled my shorts and underwear down to my ankles. This wouldn’t have been so bad had another kid from my class not walked in also. He ran out laughing and ended up telling everyone that I still wore tighty whities (which was unfortunately true). I ended up getting a lot of teasing, especially from the girls. It was so embarrassing!! I ended up not talking to anyone but my best friend for the rest of the day. Thankfully it was the end of the year so mostly everyone forgot over the summer!

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underwear one

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At the park there’s like theses gates and everyone likes to climb over the gates, and I was with my friends including boys and I’m wearing a skirt and what happened was I got up on it and sort of crouched and jumped off but the band of my skirt was stuck in the fence so it literally slipped off😂 never been so embarrassed

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He got an eye full

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I was speeding and a cop pulled me over. I was driving back from my job. My purse was behind the front seat, so when the cop asked me to show him my license I had to turn around and lean back. When I showed him my license, he was acting kinda funny and said he’d just let me off with a warning. Then I noticed I was wearing a short skirt and no underwear. He got an eye full.

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Underwear Showing

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I went to the library in a pair of black, baggy running/athletic shorts. There was no inner mesh for the shorts…. The library was fairly busy and there were no desks available. I ended up sitting at the back, on the carpet floor and up against a bookcase. My shorts were locked in place by the carpet but my body slid forward because of the angle I was seated and the material of my shorts….

There were two tables of private schools girls (mid-teens) nearby. The girls were chatting a lot, moving around and looking for books. I had to swing my legs a few times, in order for them to get by. In the process, my underwear shot out from my shorts more and more. Then I got caught up reading the paper and slid further a little more. One of the girls was to my right but five aisles away. She called out to the table and they all huddled in the corner to my right. They giggled, returned to the table and whispered. One of them came towards me and said, “excuse me sir, your underwear is showing!” They burst out laughing and giggling. My white underwear had been sticking out by an inch and a half from my shorts. I quickly adjusted myself and kept my head down embarrassed. I waited for them to all leave the library before making a departure myself.

 

 

 

 

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