Picking Wedgies: The Story Of A Guy With Underwear TroublesThis is the story of Shane, a boy i went to high school with, and his underwear troubles. Shane and I were in the same grade at school. He was quite shy, but he was also immature and boisterous, particularly around his mates. Shane's parents were divorced, and he lived with his father, two younger sisters and and older brother and older sister - both about 4 years older than Shane. His father was a fisherman who would go out on long fishing trips for his work, often away from home for long periods. As a result it seemed that things were always unstable at home as step-mothers and random carers seemed to look after the family from time to time, or they were sometimes left to the care of his older sister.
Shane was quite fit and athletic and he played Aussie Rules Football quite well (AFL). Even though he wasn't short, he did wish he was a bit taller like some of the other pla
We went to high school was in the early 90s, when it was common for boys to wear short and/or tight-ish shorts and briefs were the most common underwear, particularly bikini briefs, or more sometimes classic styles. Things were changing a little bit, Home-boy and Rap culture was emerging along with baggy jeans and boxer shorts. Despite this, while some boys started wearing baggier shorts, many didn't, and briefs were the most common choice for undies. Furthermore, AFL shorts were continuing in the tradition of the 70s and 80s, as very tight and short shorts for ease of kicking, but the material seemed to have some stretch to allow manoeuvrability.
Our school uniform consisted of stretchy cotton maroon shorts on most days (the "sports" uniform), except Fridays and 'special' days, when we had to wear grey dress shorts with a special button up shirt. Both of Shane's shorts were cut a little less than half way down his thigh, similar to many boys at school, even though some wore them even shorter and some quite longer. His maroon sports shorts fit a little tighter on his bum but they were still quite loose and stretchy from the material. His grey dress shorts were actually a little shorter in length, but actually seemed just a little bit looser, but the material had almost no stretch in it.
Now enough of all these details, important though they are. When we were in grade 9, I remember taking notice of Shane for a particular reason, which led to me noticing the details mentioned above and getting to know him. I remember the day I saw Shane during lunch time, he was wearing his maroon sports shorts and was playing around with some of my other friends. After nearly every move he made, he would pick at his bottom, pinching and tugging at least once with his thumb and forefinger. I began to notice that he was often doing this, and I realised that he was in fact pinching at each side of the back of his underwear, confirmed when I could see the crease of both sides of his underwear particularly if he bent or sat down, tightening the material of his shorts against his bottom. As I saw him picking at each side of his underwear I became more fascinated with what would cause him to pick, the way he would pick it, and more. Sometimes I noticed him pick very quickly just one side, particularly if he was in the middle of doing something and had little time to pick. Sometimes I saw him pick one side and then the other side - actually this seemed to be the most common. Sometimes he would pick both sides but then would go back and pick the first side again, as though the actual act of picking one side made the other side slip back in again, and sometimes he picked each side 3 or more times, trying to get his underwear to stay in the right place. Sometimes he would use both hands at the same time, or one after another, or sometimes just one hand to pick both sides. There was one final thing about his picking - sometimes he would also pick his crotch just once or twice, which would cause him to need to pick his wedgie at the back again.
I had seen this kind of thing from other boys once or twice before - and I had been intrigued by it then too - in fact I remember dealing with some underwear that caused some bad wedgies myself. But Shane's underwear problem was particularly bad. For example,when Shane was walking at a normal pace, I would take notice of how many steps he would take before needing to pick his wedgie again. Most of the time, about every 20-30 steps he would pick at least once, and often as he walked he would pick once with both hands and hold it out for a couple of steps before letting it go. It seemed to be quite a problem for him.
The next thing I noticed was, the next day at school, he was doing pretty much the same thing. As I came to discover, some days his picking seemed to be particularly bad, and others not so bad (just walking didn't seem to cause as many wedgies), but as long as I was looking, I noticed him adjusting his underwear at least after sitting or bending or some significant body movement. I also found Shane's wedgie-picking habit interesting for several reasons. For example, he was obviously uncomfortable in his underwear (some days worse than others), so he was conscious of it, but it also seemed to be a fairly consistent habit, and the way that he constantly adjusted himself also seemed as though he was very used to this problem, like he had been doing it for some time. Despite this, I also noticed him taking time to do what seemed a like a 'frenzy' of picking, particularly on a bad day of picking, when he seemed to pick and tug his underwear back and forth, holding it out several times until he seemed a bit more satisfied. Otherwise, Shane's picking was more routine as he struggled to keep his underwear out of his bum, adjusting it quickly but continually. I remember noticing that, if he sat down or made some significant movement, I knew he would always pick, and if it wasn't immediately, he would have to do it eventually. From there it was always interesting to notice how often he would adjust himself after smaller movements, or even just from walking, as I mentioned.
Not long after noticing this, I remember seeing him during AFL training. As I mentioned, AFL shorts at the time were skin-tight (or close to it) and very short, often cut just below the bum, or at the top of thigh. Although they were very tight, the material was very stretchy, and they were often very tight across the bum and crotch, sometimes you could see many boys' packages quite clearly - it must have made it easy to kick high and manoeuvre easily, but they were very very snug, and I had noticed boys shifting and adjusting themselves before in their AFL shorts. All of the boys wore shorts like this, some of them a bit tighter than the others, and our school's team wore red shorts. Shane's shorts fit as sung as most boys - you couldn't see much of his package, but of course, because of his perky bottom, it was very tight across his bum. What you could see, much clearer than in his other shorts, was the outline of his underwear, visible most of the time, unless the light wasn't good.
Immediately it was obvious that, in his AFL shorts, Shane's wedgie problems were even worse! It seemed as though the shorts were causing the underwear to slip in his bum with the slightest move. I remember wearing AFL shorts myself when I was just a kid, and feeling like the shorts themselves fit in a way that meant they were always riding up, so the combination of these shorts with his underwear for Shane must have been terrible. Now he was tugging and plucking his butt, having picking 'frenzies' whenever he could and also holding it out a lot more while he walked - he would sometimes stand there holding onto one side of his underwear with two fingers as he listened to instructions of the coach. Moreover, as you could see the outline of his underwear quite well, you could now see the problem he was having. I watched him walking, noticing the creases of his underwear slipping up as he walked, seeing him pluck each side as best as he could, and then watch it slip back in bit by bit as he kept walking, until he would pluck both sides out at the same time and hold it out as he walked for a while - that must have given him a bit of relief! However, as he was playing an active sport, he often didn't have much time to adjust himself. When he was playing or training, his problem didn't seem to affect him, until he had a moment to spare, when he would take some time to pick and tug in a good frenzy of picking. But sometimes there wasn't much time to fix a wedgie properly while playing, but he would usually try. I remember one time he had total control of the ball during a game as they waited for him to kick a goal. Right after he had caught it he picked and tugged out both sides a couple of times with one hand (not as easy as with two!), picking quickly as he could, almost as though he wasn't thinking about it. Then he prepared to kick the goal, bending over and pulling his socks up a bit, then picking each side of his undies again, swapping the ball to the other hand momentarily to pick again. Finally he focused on the game and kicked the goal. After that I'm fairly sure I remember him walking away, picking again and holding his underwear out of there for a bit as he walked. So it was quite a problem! But just like when he wore regular shorts, it seemed like he was quite uncomfortable, but as though every time he adjusted himself it was what he was used to doing.
So I found his problem extremely intriguing, so much that I became obsessed with his little habit. I couldn't believe it when I saw him in his AFL shorts, watching his underwear slip up over and over and seeing him struggling to keep them out of between his cheeks, to get the sides of his underwear to cover as much of his bottom as he could, but it just wouldn't stop slipping back up there. So I got to know Shane over time as I hung out with him and his friends at school, and for nearly 7 months during grade 9 he seemed to deal with this problem, some days when he seemed to be having a lot of trouble, and others not as bad, when he only seemed to pick at his butt (and sometimes his crotch) after sitting or bending.
At one point I actually decided I would try and talk to him about it somehow - actually I couldn't believe no one was teasing him for it, but I suppose he was a pretty well respected for his footy-playing skills. I can remember a day when he seemed to be forever adjusting himself: we were playing handball and he was quickly plucking and tugging while he played, until he lost and got out of the game, when, after running and bending a bit to catch the ball, he threw it to me. Then as he walked over to where I was sitting, he had a little 'frenzy' of picking, ending in him standing in front of me. As he did, he asked me something and he quickly adjusted his crotch, and then picked both sides of his underwear at the back, as though it was normal and that I wouldn't notice. I can't remember what he asked, but I know I said to him eventually "you are always adjusting yourself, do you have worms or something?" He seemed a bit embarrassed, but he jokingly shoved me and said "No, I don't have worms!" So I shoved him back and said "well why do you keep picking your bum?" He laughed, and the fact that I shoved him back seemed to impress him, and he then opened up to me a bit, saying: "yeah I know I have really bad undies and my bum is too big for them" and laughed, so I laughed back, saying, "you should try boxer shorts". And he said "yeah I had some but I hate them and you can't run and play sport in them". Suddenly I thought that I had better not talk about it too much - I didn't want him to get too embarrassed and stop doing it, because I thought it was so sexy! So I just said; "well as long as it's not worms" and we kept playing handball - with him still picking his bum all the time, of course.
As I got to know him, I once was lucky enough to visit his house. I remember he showed me his room and we played some of his nintendo games. At one point he had to use the toilet, so I was alone in his room. I couldn't help myself, I HAD to look in his underwear drawer. In the top drawer of his cupboard were about 6 or so pairs of bikini briefs, all of them different colours. They looked quite normal, but they did look as though they might be a bit small for him. However they looked familiar to me, I think I had warn similar underwear myself. I looked at the tags - they were "solutions" brand which I now know were available at Kmart. I looked at the sizing and noticed that some of them were size 10-12 and others 12-14. We were both 14 at the time, so they were certainly a bit too small for him, but even more noticeable was that his underwear looked a bit old and warn out. The I noticed a basket on the other side of the room - it was his washing basket. I searched through and near the top was a pair of dark purple bikini briefs that looked quite old, size 10-12. I remembered the previous day, Friday, he had been picking his wedgies constantly so it was very exciting to see them.
As I was to discover, these "solutions" undies were very cheap, and the elastic around the leg-holes was quite lose, causing them to shift and not stay in place properly - I bought a packet for myself a little while after to try them out. From the beginning of Grade 10, Shane's picking had become much less frequent - he must have got some new underwear. But I will never forget when he had such intriguing troubles with his underwear the previous year. The whole situation was so sexy to me, and I loved thinking about all of the factors that probably contributed to his problem. First of all, his bottom was a bit large for his size and its shape seemed to cause a problem with wedgies for him. Secondly, his underwear was obviously old, too small, and bad quality. When he told me about his situation with his father and siblings at home I later thought that this must have contributed - a more stable parenting situation might have avoided him missing out on new underwear when he needed them. They must have got him some boxer shorts, as he mentioned, but they weren't suitable for him - he obviously preferred the support of briefs, even if it meant dealing with constant wedgies. But also, the commonly tight AFL shorts and types of underwear worn at the time must have contributed to the problem as well. Furthermore, it really seemed as though Shane was used to this little problem, so I imagine that he probably had wedgie problems (considering his bubble butt) since he was a kid, and AFL seems to involve wedgie picking to some degree anyway, considering the the wedgie-causing type of shorts worn at the time. So Shane probably accepted his wedgie problem to a degree for these reasons. Regardless, I found it extremely sexually arousing that this fit young man was forced to deal with such an uncomfortable clothing situation, but he accepted it, and his habit that developed from this had me absolutely mesmerised with him!