Penny -- (Author) gbab65

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Author: gbab65
Timestamp: Mar 16, 2025 at 4:27 PM
Content: PennyI was 8 years old and on holiday with my mom and 4 year old sister Sally and we were staying in a caravan on a site just up from the beach. It was one of those dreamy summers we all remember when it was day after day of bright sunshine and heat, unbelievable heat.

All of the caravans had decks down one side and across the front that had picket fences around but you could still see through. Me and Sally would go out still in our PJ’s to have breakfast on the decking at the table under the umbrella and looking round, most of the other families were doing the same thing.

At the caravan next to us, 2 girls would also come out in just their nighties to eat their breakfast at their table. The older one looked a bit older than me and the younger one about the same age if not a bit younger I thought at first. That was until I saw them sitting at the table and could see under her nightie that she was wearing a nappy like Sally does for bed and trips, I figured the younger one must be a lot younger than I thought.

After breakfast, Sally and I went off our decking to play on the grass area just in front of our caravan and started playing catch with a tennis ball. Sally was not very good and kept falling over with her legs in the air. This showed that she had still not got changed from the night before as her nappy was in full view to me, something that I secretly envied.

The next day and again Sally and I were playing with the ball after breakfast when the two girls from next door came over to us. They were Nickie who was 10 and Penny who was 7 and we were soon all four of us playing catch. We split into teams with me and Penny vs Nikie and Sally. It soon became pretty obvious that Penny and Sally, whilst been 3 years apart, were very similar in their actions and dress with them both rolling around legs in the air showing off their nappies to the world. I was now even more envious.

A bit later on after we finished playing, Nickie and Penny went back to their caravan as we went to ours and we all got dressed.

It was a really hot day and mom was on a sun lounger on the decking reading her book, Sally was in her room playing with her dolls and I was bored so I went exploring around our caravan. Between our vans, I found Penny who was looking at some creepy crawlies as she was also bored. I said we should go to the playground as they had swings and slides so I told mom and Penny told her mom. Heather, and we off on our adventure.

It didn’t take me long to see that Penny was still wearing a nappy under her shorts, in fact her stretchy shorts failed to hide it at all, a 7 year old out wearing a nappy without a care in the world.

We were soon chasing each other around the playground and having fun on the slides when Penny went under the slide and squatted down, just for 30 seconds and then stood up again with big grin on her face. Her nappy looking a bit more bulky and I realised that she must have stopped for a wee. We had been playing for quite a while when Penny’s mom called her in for a quick break. We agreed to be back out when her mom had finished with her.

I went into our bathroom for a wee and seeing Sally’s pack of nappies in there and feeling adventurous, decided to see if I could wear one too and it fitted, it was very tight but it fitted. I was now wearing a nappy too so pulled up my shorts to hide it and went back out to play.

This time though, going back to the playground, Nickie had come out with Penny and Sally had wanted to come with me so the four of us were off playing.

Over at the playground, they also had a toddler paddling pool and with it being so warm, we were soon all splashing about in there. As it was during the day, Sally had got dressed in her swimming costume and just put her shorts over the top, no nappy, Nickie Penny and me were all wearing T shirts and shorts. Predictably, Penny slipped over in the pool and we were all laughing and as expected, her previously discreet nappy was now a bit more obvious as it had swelled under her shorts but no one cared and we continued playing. I then slipped onto my bum in the water as well but I got up quickly, so I was convinced that I had got away with it. But still everyone was now laughing at me because I had a wet bum.

Fun had, we were off back to the caravans. All four of us now looking like drowned rats, I was quite impressed with how Penny’s nappy had expanded and looking down at my front, I was quite pleased mine was still discreet. Standing on the deck watching us walk back and passed to the gate and steps up, mom said

“Looks like someone is ready for a nappy change!”

“Yes” I said, “Sally fell over in the paddling pool”

“I can see that but she’s not the only one though” mom replied as I walked up on to the decking towards her

“No, Sally has got her swimming suit on” I corrected but mom knelt down in front of me and pulled my shorts down exposing my nappy

“Yes, I know Sally has got her swimming suit on, but you seem to have her nappy on” as mom squeezed the back of it “and it’s wet”

“errm but errm, I was just trying it to see how it felt and I slipped in the pool and its only water and I didn’t mean to and I was going to put it back”

“OK OK lets go and get you changed anyway, I want to go out into town in a bit”

Mom led me and Sally back into the van and took Sally first to get her changed.

Realising that this maybe my only chance ever to try it, I wanted to know what it was like to wet a nappy. I stood there thinking about and trying to relax and felt a little trickle that then grew into a full on wee. I was standing there wetting my nappy and I was overwhelmed with the feelings I got from the heat between my legs as I flooded it. It was everything I thought it would be and more and now I was going to lose it, but at least I got to try it.

Sally came out of her room, now dressed in a little dress and sat on the floor in front of me trying to put her shoes on, this exposed her underwear to me and she was now back in her nappy.

Mom followed her out and into my room saying

“Come on the, let’s get you changed too” mom then proceeded to pull my shirt off over my head then leant forward and pulled the tapes off my nappy letting it fall on the floor with a thud.

“OK mister, nappy or pants” a comment I had every morning when Sally first started potty training. I just stood there trying to comprehend what was happening.

Unexpectedly, mom then got another nappy and spread it on the bed before picking me up and placing me in the middle of it. I just lay there speechless as she fastened it around me.

“if you can’t say it, then it obviously isn’t pants”

Mom then slipped a t shirt on me, quite long and covering my bum.

“You’ll be OK like that for a bit until we go out”, we walked out into the living area and mom made me us glass of squash each

“When it’s hot like this, you have to make sure that you keep drinking, OK”

Me and Sally went out on to our deck and saw that Nickie and Penny were playing catch by our van so went and joined them. All 3 of the girls were wearing short dresses and I soon caught sight that Penny was in a nappy too and both me and Sally were in nappies and my T shirt only a smidge shorter than a dress.

“I should get paid for looking after you lot” said Nickie “after all, I must be the babysitter as I’m the only one not in nappies”

“I thought mine was hidden” I squeaked

“Well, it was not very noticeable at the front but you had a big square bum at the back” Nickie giggled. I just relaxed and stated to play, It was now how it was now and I was loving it.

Mom came out a few minutes later with another glass of squash for us seeing Nickie and Penny, she brought extra glasses too.

“I can’t keep drinking this much” I said but mom smiled and said

“you need to, I’ve just balled your wet nappy up and your wee is not clear so that means your dehydrated”

“But if I keep drinking then I will need to keep weeing”

“I know” she said “But it’s not a problem I’ll just have to keep changing nappies.”

Before going on holiday, mom had been potty training Sally and Sally had only really wore nappies for bed or for really long trips like coming on holiday, but with me now in a nappy, Sally was too. I was getting exactly what I had longed for.

Sure enough. Me and Sally wore nappies for the journey home too and I was having no difficulty using it however, once back home, I was back into underwear and penny was only in nappies for bed.

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Author: gbab65
Timestamp: May 18, 2025 at 3:17 PM
Content: 5 years later and we went back to the same caravan and unbelievably, Nickie and Penny were there again. On asking, it turns out that they owned their caravan and they were there loads of times throughout the year and every year. There were times that they let friends use it, but it was mostly them.

There was no hiding that Penny was still wearing a nappy as her leggings emphasised it rather than hide it. Seeing my obvious realisation, Nickie went on to say that Penny had been diagnosed as autistic and while she was really clever in some ways, she was quite delayed in others. Being as we now classed ourselves as real friend’s and not just acquaintances, we all swapped addresses too so we could stay in touch in future.

Sally was now 9 and completely out of nappies, I on the other hand now 13, would get and wear a nappy whenever I got the chance. The new largest disposable nappies fitting me easily as I was still one of the smallest in my year at school. Nobody ever mentioned me wearing nappies, so I assumed I was getting away with it undetected.

As before, I was mainly playing with Penny. I was just attracted to her and loved the fact she was still in nappies rather than being put off by it.

Whilst round at next doors van with Penny, Heather did openly ask

“Does anyone need their nappy changing?” obviously assuming she was only talking to Penny in her normal joking manner. Heather never got cross or serious with Penny about her nappy and always kept in a joking manner as if it were just a game they were playing and Penny, responsible for choosing her own clothes in a morning, just wore what every other girl her age might wear even when it was revealing stretchy leggings.

I on the other hand, always wore my baggiest shorts to hide my padding even if some of them were very short, they still hid everything.

That autumn at home, mom got a call from Heather asking if we wanted to go down to the caravan with them for Halloween weekend. Mom could not go as she was working and Sally did not want to go without mom, but I gladly accepted.

Nickie and Penny only lived ½ hour away from us at home even though it was a 4 hour drive to the caravan. On the Friday of the Halloween weekend, mom me and Sally all drove down to their house so I could travel to the caravan with them. Mom and Heather went off for a private chat while we were all getting reacquainted. I could not take my eyes off Penny, I thought she was just the most amazing girl I had ever seen and I so jealous of her still being in nappies when I was no longer able. Penny then asked me

“Have you got a nappy on your bum?”

Not willing to let the truth out, I denied it with

“No, I can’t anymore. It’s not really fair but I’m too big” Mom and Heather then reappeared as mom was getting ready to leave. Penny then stood up and to everybody and nobody in particular, she said

“It’s not fair that Gary can’t wear a nappy anymore”. Nickie stood there trying to control her giggles, Sally laughing too and mom and Heather looking at each other like they knew something.

I got the full warning off mom, before she left, that I was supposed to do exactly as I was told by Heather. Then mom left leaving me ready for my adventure.

We were driving down that evening and Heather had been busy packing the car before coming in to tell us

“Right, nearly ready, just last things to do. OK Penny, can you come with me please” at which Penny and Heather went into the back room. Nickie said

“She is just getting her nappy changed ready for the trip down” Heather and Penny then reappeared after only a couple of minutes

“OK Gary, your turn” and I started to follow Heather and I heard Nickie say

“And Gary is getting his nappy changed too” Looking at my shocked expression, Heather said to me

“Don’t worry, I spoke to your mom. She said you’ve been having some wet dreams and that it was OK for me to put a nappy on you. That is if you don’t mind. It just helps me to keep things clean and tidy and after what Penny just said, I think it is what you want as well” I didn’t know where to look or what to say so I just let Heather carry on. There was a changing mat on the floor with what was clearly a baby’s nappy already open on it waiting for me.

Heather pulled my shorts and pants down to my ankles

“OK, I see you got yourself ready for this trip but this looks a little small on you.” before untapping my nappy and spinning me round and landing me on the nappy. Nappy pulled up between my legs and each side expertly and tightly taped into place. “See, I knew it would be a better fit. These are special nappies for special kids” Heather commented while standing me back up. “Take your underpants off, you won’t need them and pull your shorts up” which I did. My shorts went over my nappy but only just and there was no hiding that I too was now wearing a nappy.

Getting into the car, I was given no choice but to get in the back with Penny. The armrest pulled down between us gave somewhere to put our drinks bottles. That said, Penny’s drinking cup was an anyway up cup like you’d give to a toddler.

“babies in the back and grownups in the front” Nickie commented as she got in and settled herself for the drive.

We had been driving for a while and I had emptied my bottle and started feeling the need for a wee.

“Are we stopping soon” I asked.

“no net yet, we normally stop about half way and that is another ½ hour yet. Are you OK. You don’t feel sick or anything do you?”

“No, I just need a wee” at which Nickie started giggling

“You’ll be OK. If you can hold it until we stop then you can get out but it doesn’t matter if you can’t, you’ve got your nappy on” I just sat back in my seat and let the inevitable happen as I wet my nappy, feeling the heat radiate between my legs and onto my bottom. A musty smell then started to drift through the car

“I think someone else needs their bum changing too, is that right Penny?” Penny just sat there giggling, I may have filled my nappy with wee but she had just done the other.

½ hour later and sure enough, we pulled into a service area.

We got out of the car and trapsed into the service area. I was very conscious of my nappy and looking round I was very aware that it seemed that there were loads of toddlers in there and all with obvious nappy bulges.

Heather took penny into the baby change leaving me and Nickie to wait.

“so have you got a wet bum too then”? Nickie asked me out of the blue.

“I.. errm… ehhh…” I failed to say

“So that’s a yes then. It’s OK it doesn’t matter to us and it’s nice for Penny to have someone who is a bit like her.”

“But I’m not really like her”

“Well, you are a bit as you didn’t fight when mom put you in a nappy and you didn’t fight it when you wet yourself, so you are a bit like her and I know you like her as well.”

Heather and Penny came out and then Heather took me in and changed my nappy in a flash. As we went out, there were a couple of teenage girls with a toddler waiting to go in. Seeing me and Heather coming out of the baby change, they went in now giggling to themselves.

Grinning widely, Nickie commented

“They know too, hehehe” as she swatted my bum with a dull thud.

We got some more snacks and some more drinks and we were back on our way.