New Home, Unexpected Experiences. (chapter 55: 29/06/26)

[Jonjon2]

But I think the whole point of the challenges is that there is at least a chance that you will lose any dignity and if its not Matt that loses it then it must be Zach I guess?
Great continuation of this series and still keeping us guessing as to what will happen next - but whatever it is I hope that somebody loses some dignity!

[Homo4u]

you make a good point i’m rooting for zach to lose his, as a check on his cockiness/confidence for inviting all those ppl. but ofc that shouldn’t come without struggle from matt.

who’re you rooting for?

[Summers]

I'm hoping Matt wins, but it could go either way.

I know as the author, i should know, as i ultimately do pick who wins obviously, but i go with the moment when i write, and don't force it either way, if matt losing makes sense in the moment, he will lose, if it's Zach, then it's him...

Glad you're enjoying the story, still can't believe how many chapters i've written, and Matt hasn't even been in his new town for a whole week yet, hehe

[Summers]

Chapter Fifty Four

The sound of chuckling and giggling also helped make my mistake even worse, as I suddenly felt something jump on me. I knew it was obviously Zach, but I was completely caught off guard. While also confused, as he wrapped his legs around my waist.

However it was one of his arms wrapping around my head and then slipped down around my neck, before squeezing, that had me worrying. His other arm hooked under one of my arm pits, and I think he must have linked his hands together, as I struggled to breathe.

It was like the hold that Wes had used on me, but instead of from behind. It was from the front, and I had no idea how to get out of it. My legs were useless, as they were keeping me upright, and I knew it would be bad if I fell over.

He also had one of my arms completely immobilised, so I just had one free, and I could only try to pull on the arm around my neck. Which didn’t really do anything except relieve the pressure a little bit.

His legs around my waist were also a problem, as not only were they squeezing around my waist and stomach, but he was kind of bouncing a little too. So with them so tight, I could feel my shorts and even boxer trunks get a little lower.

Thankfully, double knotting the drawstring on the shorts, was a good idea from Jake and Leo. So I was at least safe from him being able to push them more down more than a fraction. Unfortunately for me, that wasn’t what he was really focusing on, as I started to get weaker.

It was getting harder to breathe, and that made it harder to not only stay standing, but also pull on his arm. I could hear the other kids getting excited, as my legs started to shake. However, as much as I tried to do something, my legs gave way, and I ended up on my back.

“Got ya!” I heard Zach then say, as he kept his hold on me.

Which wasn’t as bad as it had been when I was standing up, as his weight wasn’t helping him basically choke me. However, there was no way out of the hold in this position, and despite doing everything I could, my eyes eventually closed.

It only felt like a second, but when I opened them again. I could hear sniggering and giggles from the kids watching. It took me a few moments to come to fully, but when I did, my eyes went wide. My shorts were off, and laying outside the makeshift ring, next to my top.

“Looks like he’s awake.” Zach said, as he stood a couple of feet away from me.

“Aww, he’s so cute, and those undies are so tight.” I heard a girl say, but I didn’t know which one.

I was too busy trying to catch my breath, as I stood back up. To really pay attention to them. I was already embarrassed, and humiliated. A boy that was two years younger than me, had just choked me out, and worse. Had managed to get my shorts off, which made double knotting them pointless.

Thankfully, this time when he tried to quickly attack me. I was at least not distracted by the others around us. So I managed to just about side step out of the way, and trip him. I tried to take advantage of him being off the ground, but tripped over myself.

I ended up on the ground next to him, instead of on top of his back. Something he took advantage of, by rolled over and on top of me. Thankfully, I turned just in time, so he at last hadn’t got on my back.

It wasn’t ideal him being on my front either. Especially after he had choked me out a few moments ago from that position. However, this time I had a bit more control, and managed to hold him off easily from getting any more advantage over me.

“You’re going to lose!” He said, as he tried to wrap his legs around my waist, but I was ready for that.

“Not, a chance!” I retorted, as I managed to roll us over, and onto his back.

I was still a little light-headed, but I knew I had to do something. There was no doubt in my mind, that he would be going for my boxer trunks next. So I needed to start stripping him, and a trainer or sock wasn’t going to do much for me.

While I would have preferred to get his jogging bottoms off, I knew from our position that I couldn’t. So I had to go for his top, and quickly let go of his arms. Something that caught him a little off guard, as he obviously hadn’t been expecting me to do that.

He did recover quicker than I would have liked, but I had already got his top up to his neck. Which had him make a similar mistake to what I had done earlier, and actually helped me get his top off his arms.

It did take a bit more effort than I thought it would to get it all the way off, as he bucked and almost through me off balance. My fight the other day with Wes, was once again coming in handy. Even if that did result in a third naked picture of myself on the website.

“Look, Zach’s nipples are sticking out.” I heard a boy call out, after I finally got the top over his head, and got off him.

To my surprise, Zach actually blushed at that, and the boy was right. His little nipples were hard, and for some reason, that was embarrassing for him. Even though I had no idea why that was embarrassing.

“Whatever.” Zach then said, before once again charging at me.

It seemed like the only opening move he knew, and I easily avoided him again. However, I almost tripped again. Which this time, made me look down. I had been so caught up in what had been happening, I hadn’t noticed that both of my shoe laces were completely undone.

“Hey!” I found myself saying, although it was more to myself, than for anyone else.

“You snooze, you lose.” I heard Zach say, before grunting in surprise, as he tackled me around the legs.

He quickly reached for the waistband of my boxer trunks, but I managed to push him away, and scoot backwards. Unfortunately, he somehow recovered quickly and lunged forward. I thought he would go for my underwear again, but instead his hands grabbed my left trainer, and pulled.

“It won’t be much longer, Matt. I am going to keep going for your underwear, but I will settle for your trainers and socks too.” Zach said, as he stood up and tossed my trainer over to the rest of my clothes.

For some reason, his taunting got to me. I guess it was because I had no idea what to really do. Every time he went for my underwear, I would have to defend against it. However, he could quickly switch to my remaining trainer or socks.

Which I guess didn’t make much difference, and were definitely better than my underwear coming off, but it still made me feel more nervous. So this time, I decided to go on the offensive, and lunged for him.

I had wanted to get his bottoms off, at least that was my intention when tackling him to the ground. However, how we fell, I changed tactics. Instead, going for his sock. Which he was expecting at all, and within a few seconds, I was back on my feet and focusing on him.

I knew one mistake, and I could be basically naked. Sure I would have two socks and a trainer left on, but they would do nothing save my modesty. His look of surprise, gave me confidence as well, because he actually looked a little unsure of himself for the first time.

Although I doubted he was worried about losing, as he still had an advantage clothing wise, but I had definitely at the very least. Got him to be a bit less reckless, and realising that I could strip him of something, just as quickly as he had been doing to me.

This time, we actually circled each other for a few seconds. The first time one of us hadn’t just attacked the other. I had hoped that he would be frustrated or something, but it was actually me that started to get a bit inpatient.

I had tried to ignore the other kids as much as possible, but their comments about my body, lack of hair. Was distracting and embarrassing, and the comments about my bulge, or as some of them pointed out. Small bulge, made me want to get this match over with. So I could get dressed.

Which made me rush my attack a little bit, but thankfully it didn’t turn into a mistake. It just wasn’t quite what I was going for, and instead of being able to get to the drawstring of his bottoms. Which I knew was double knotted.

I had to settle for getting his remaining trainer off, but to my surprise at the same time I managed to pull his off. After struggling a little bit because of how he had tied the laces up, I actually felt my remaining trainer slip off. Which left us both holding the others.

“It was pretty much the same time. So they both count.” I heard Amanda say, as we kind of stared at each other.

“Okay.” Zach said, as I nodded in agreement.

I couldn’t be bothered to argue, and it didn’t really matter. It didn’t change what I had to do, and that was to get his bottoms off. I just needed to get him on his back, and pin him down. Something I hadn’t really been able to do, despite having the size advantage.

Annoyingly, it was becoming obvious that despite my size and age advantage. Zach was definitely the better wrestler, or at least better at what we were actually doing. Every time that I thought I had him in a good position, so that I could untie his jogging bottoms to get them off.

He would manage to pull at my underwear, and even revealed my bum cheeks a couple of times. Which made me retreat back and protect myself. The other kids loved it, and the girls comments were definitely distracting me more and more.

After a little exchange, where I got both his feet barefooted. While he had managed to leave me with just one sock and my boxer trunks. I was getting nervous, as I hadn’t even managed to loosen the knot on his bottoms. Despite have a few attempts at it already.

Then a moment that had me mortified came, and even though it had an upside. It definitely didn’t feel that way, as he held me in what I think they call a spladle or banana splits. Which all came after I thought I had finally trapped him, and could work on that stupid knot.

[Jonjon2]

The tension is building - a terrific last sentence; just leaving us wanting to know what happened? Great!!

[colomale2]

Great chapter! Now it is clear Matt will lose again

[Summers]

Chapter Fifty Five

I had no idea how he had managed it, or even what had happened for a few moments. One moment I was reaching for the knot, and the next we rolled over a couple of times. He had somehow hooked one of my legs at the knee with his legs, and the other with one of his arms.

“Oh my god!” I heard a couple of the kids call out, with a mixture of giggling and cheers added by everyone else.

I was trying to get myself free, but no matter how hard I tried, I was stuck. I had no idea how to get out of this hold, and wasn’t even sure if I could. I had heard of it, and remember seeing some videos on Youtube, but never really gave it more than a chuckle.

“Get… off!” I found myself saying in frustration, as my legs, back, and neck started to ache.

It wasn’t that painful, but it definitely felt uncomfortable. Which was nothing compared to how humiliated I was feeling at the same time. My legs were completely spread open, and I was kind laying on my shoulders. So the comments I was hearing, were making me blush more and more.

“You’re so lucky you aren’t naked.” Zach then said, as he tugged on my spread legs a little more.

“Look, you can kind of see his balls and willy through his undies!” I then heard a boy call out, and my eyes opened wide.

I tried struggling again, as I realised that while they couldn’t see anything directly. They could obviously see the shape, as my boxer trunks were already tight. So I knew in this position, that they were giving everyone a good view.

“If you agree to take your underwear off, I will let you go.” Zach then offered, and even though it was a little awkward to turn my head to look at him. I couldn’t help but give him a surprised look.

“No way!” I then responded, with a shake of the head.

There was definitely no way I would do that. Not only would it leave me with just a sock on, but I would be completely exposed for whatever was left of the match. It was bad enough that they could see the shape of my bits through my underwear.

Them seeing them in the flesh, was definitely not going to happen. However, as I tried to break the hold again. I found myself getting more and more tired, and realised that I really might not be able to get out of the hold.

“Hey! What… stop that!” I then called out in panic, as I felt his hand on my underwear.

“Doing what?” He asked, as his hand kind of just rubbed and pressed over my willy and balls.

He wasn’t grabbing them or anything, but just rubbing in gentle circles. At first because of the shock, I didn’t really understand what he was doing. However, after a few moments, I realised that something was definitely reacting to his hand.

The other kids were obviously watching, and I could tell that at least a few of them realised what Zach was doing. There giggles and chuckling, made it obvious, and the comments weren’t helping either. Neither was my struggling, as he easily held me in this embarrassing position.

“Stop it!” I called out, but quietly.

“You know the deal.” Was all he said, as he kept up the rhythm of his rubbing going.

When I started to get hard, he started to grab it a little bit as well. Making it react even more, and I couldn’t believe what was happening. There was no way I wanted to end up naked, even if I would still have a sock on. Although, I also didn’t want him to keep rubbing me.

It wouldn’t be long before I was fully hard, and I honestly had no idea if he would stop rubbing or not when that happened. A part of me thought he would be too young to know what he was really doing, but I also knew this place was different, and not like where I used to live.

A new problem came up though. Which ironically was caused by something else coming up. That made me agreeing to strip even more mortifying. I was now fully hard, and he wasn’t stopping. In fact his fingers were wrapped around it now, and it felt good.

Being naked in front of everyone, was definitely not something I wanted to do. However, I had almost gave in and accepted his deal. The problem was, that now that I was hard. It would be even worse. I couldn’t be naked and hard in front of them all.

So with a monumental effort, and having no idea what I was even trying to do. I rocked as hard and with as much effort as I could. Back and forth, and while I didn’t know if this was even the way to get out of the hold. I think I caught him completely off guard, and he wasn’t ready for it at all.

I thought I heard Amanda say something, but it was hard to hear over the cheering and hollering of the other kids. Not that I really cared that much, as I had somehow managed to roll over him backwards, and free of his hold.

“Not so fast!” I then heard Zach say, and my heart sank a little.

I felt him pulling be back over, and felt his legs hook under my left one again. However, either he was rushing it, or I reacted faster this time. Because I managed to not only block his attempt at another spladle, but I pulled him over me into a series of little rolls.

It felt a little dizzying, but finally my size and strength advantage seemed to pay off. I managed to get on his chest, with his arms trapped with my legs either side. Most importantly, I was facing his feet, and crouched over. So my erection was at least hidden from view.

“Got you now!” I decided to say, as I leaned forward and began to work on that stupid knot, that was holding his jogging bottoms in place.

“Get off!” I heard him say, and actually struggled a little to keep my balance, as he bucked and rocked under me.

Instead of saying anything else, I just concentrated on keeping my balance. While getting the knot untied, which I had to give him credit for again. He had triple knotted the string, and it took me a lot longer than I wanted it to.

I think even the other kids were getting a little bored, as their excitement seemed to turn into insults and teasing, directed at me. Something that made me start to blush again. However, the time it took me, also worked to my advantage.

Zach had been trying to get out from under me the entire time, and almost got me to lose my balance a couple of times. Which I didn’t blame him for, but by doing so. He had also tired himself out, and he barely managed to put any resistance up, when I got off him and pulled his bottoms off.

To his credit, he didn’t blush that much or seem that embarrassed. Something that shouldn’t have surprised me, after what everyone I had spoken to about Zach, had told me. Although I could tell that Amanda’s teasing did seem to bother him at least a little bit.

“Looks like Matt has the advantage now. One sock and undies, against just undies.” I then heard a boy call out, but I had no idea who it was.

It wasn’t even that much of an advantage. He would definitely be going for my underwear, just like I will be doing to him. Because even though I would have a sock left on, I would be effectively naked, and even though I had been seen naked more than I would have liked already.

I was worried I would freeze or get too embarrassed, and he would easily get my sock off. So I had to make sure he didn’t get either off me, and I ended the match by fully stripping him. I just had to not do anything stupid.

“Nice tent, by the way.” I then heard Zach say, and my plan of not doing anything stupid, lasted a few seconds.

No sooner had I looked down, to see that despite there being a little bit of a bigger bulge than usual, I wasn’t hard. I heard the other kids get excited, and barely had time to look up, before I felt him tackle me around the knees.

I wanted to call him a cheat, but almost as soon as we hit the ground. His hands were reaching for my boxers, and I forgot all about speaking. My instinct was to reach down, but I didn’t want to get into a tug of war with my underwear. So instead I used my feet and legs to push him away.

Something that probably wouldn’t have worked out well for me at all, earlier in the match. However, he seemed completely caught off guard by it, and he was obviously pretty worn out as well.

Earlier he would have been on the attack again, but he only rolled onto his knees. I could see him panting a lot, and went on the attack myself this time. Which almost turned into my second being stupid moment, as he grinned.

He had been baiting me, but not completely. Something that saved me, as he tried shift to the side and reach for my boxer briefs. Which again, I think earlier in the match. Would have worked, but he was genuinely tired, and I managed to grab his wrist and pull him with me.

Forcing us into another few moments of rolling around the make shift mat that they had set up. I could hear the other kids cheering and calling stuff out, but it was almost impossible to understand most of it.

Especially as I felt his hands gripping the waistband of my underwear and pulling them down. Luckily, he only managed to expose the top half of my bum. Before we rolled over again, and he lost his grip.

“Fuck!” He then called out, as I returned the favour.

Only this time, us rolling over didn’t break my grip, and as he tried to get away. He just helped me pull his briefs down. For a moment, I almost lost my grip, as they reached his knees, but his momentum, again helped me.

“No!!!” I heard him calling out, as his attempt to get free, ended up costing him the match.

“Yes!!!” Was my response to that, as I rolled over onto my knees. With his briefs in my hands, and a grin on my face.

[mars357]

Yaaaay! Go Matt! It's actually nice, given how the game goes and everything, to see something go well for him as well now and then!!!