Re-Rolling the dice

Pressure building

I sat as bored as ever in class on the last day of school yet we still had hours left, I sat with my head on my desk thinking of all the mounting pressure about starting high school next year, the room was dark and our teacher was playing a movie, I zoned out and thought of all the times of when me and Lily where young and we used to play for hours but now she's sixteen she doesn't want to do it as much and I can tell she wants to but it makes her feel different from her friends. "Ring ring ring" I heard the bell ring to signify the end of primary and the beginning of high school, cheers echoed around the school as everyone rushed from their classes to get home as fast as possible and as I walked out I headed in the opposite direction to most as I had a quick way of getting home. As I walked I heard the sound of trainers hitting the pavement and as I turned I felt a large weight jump on me and as she hugged me I said "hi Ollie, I don't know why your so excited I saw you like twenty minutes ago" "we finished school you idiot of course I'm happy" said an overly excited Olivia who has been my best friend since we where about three. As we walked home she bounced around with the same amount of constant energy she has had since she was about five, "Leo, do you want to stay over at mine tonight? remember I'm going away for the summer so we won't have much time" she said still hyper "I mean sure but I have to ask mum" I replied and she simply nodded. As we walked up our street Olivia ran up to my house forcing me to follow her and as I unlocked the door I shouted to see if my mum was home which she was and once we wandered into the kitchen mum was baking something "mum can I stay at Olivia's tonight?" I said in my politest voice "oh yeah sure" she said as she turned around "oh hello Olivia I didn't realise you where here" mum said clearly surprised. Olivia and I ran to my room quickly and as I chucked some clothes into my bag Olivia walked around looking at things as she does every time she comes into my room, in my bag I put my pajamas and another pair of clothes and lastly my sleeping bag then zip up my bag and as we walk out my room we bump into Lily "where are you two going?" she says for once actually confused "I'm staying the night at Olivia's house" I say before we sprint away and I shout bye to my mum. As we walked to Olivia's house which was only a few away from mine we saw her mums car pull into the driveway and we ran up to say Hi and as we gave her the run down of why I was here she opened the back door and out hopped Olivia's seven year old sister Mia. As we all went inside Olivia's mum made us some food as Mia ran off "where's she going?" I asked inquisitively "oh she probably just needs to go potty after a big day at school" their mum replied with no shame for her daughter, as we ate Mia walked back around the corner and sat with us at the table where we talked about our last day at school and plans for summer which for them was going away for three weeks to Spain. After our food me and Olivia retreated to her bedroom which was next to Mia's and as we walked in I got out my sleeping bag which I laid on the floor next to Olivia's bed, as we talked on her bed I  enjoyed the ambience of her room of the purple walls and her large walk in wardrobe. After only about fifteen minutes Mia walked in and asked if we wanted to play princesses with her and knowing that I wouldn't hate that Olivia nodded as we walked into Mia's bright pink room filled with toys, barbie dolls and other brightly coloured things, Mia was already wearing a pink dress and asked us to put on something similar "Mia what do you want us to dress up as?" Olivia said as I looked around in confusion, "Pink" Mia stated and then forced me and Olivia back into Olivia's room. "Leo I think you might have to wear my clothes but they might be a bit big" Olivia said which annoyed me but accepted that she was taller than me by quite a bit, in fact I was probably closer in height to Mia than to her, as Olivia found a similar pink dress but which was designed clearly for an older child. Olivia handed me a few outfits which all where far to big and I eventually gave in and we walked into Mia's room where Olivia asked if I could wear some of her clothes as her own where to big, Mia giggled at this but nodded and as we looked in her closet Olivia handed me something that would have made most boys petrified but made me simply nod as I had already accepted my fate and I walked back into Olivia's room to change but she followed me "Ollie I'm getting changed can you leave?" I said a little annoyed but she ignored me as she closed the door and gestured for me to get changed. Considering we have seen each other do some pretty odd stuff I nodded and turned away from her as I pulled off my shirt and pants leaving me in just my light blue undies which made her snicker as she revealed her own panties which where virtually the same, "are you gonna get changed or do I need to help you?" she said both to embarrass me but also to check in. I pulled up the pink tights I held in one hand and they felt very tight against my skin but not uncomfortable then I stared at the bright pink dress in my other hand and then I saw two hands come around my side and Olivia grabbed the dress out of my hand and then she pulled it over my hair and helped me put it on before letting me do the arms and giggling at my appearance "cause it's only us Mia and mum can I do your hair?" Olivia said excitedly which I reluctantly too. As I sat on her bed she pulled my blonde hair into two double buns which surprised me by the fact that I actually have enough hair to do that, as I looked at myself in the mirror I looked almost exactly like a young girl. When we walked into Mia's room she giggled at my looks but enjoyed them and we then all pretended to be princesses but half way through our tea party Mia started shifting a lot in her seat "Mia do you need to go potty?" asked Olivia which Mia nodded to before saying  "Onwy a wittle" "ok but you better not have an accident" Olivia said back as we continued playing. After another five minutes Mia rushed out the room and Olivia and I shared a glance before she went to check on Mia, when they came back Olivia pulled off her dress which revealed her pink panties, only the front was actually more purple and I could tell she had an accident as sometimes when me and Lily used to play in the garden usually with the sprinkler on and her pink clothes would get wet and turn purple. We didn't mention Mia's accident as she changed and went downstairs to watch cartoons and before long their mum called us for dinner and Olivia took out my hair and put Mia's clothes back in her room as I changed into my boy clothes, as we enjoyed dinner I too started to feel the need to pee but shrugged it off as the food was really good. After dinner Olivia took me to their basement to play games and on our way I ran into the bathroom and as I relieved myself I looked around and saw in the bin what looked like a pair of purple panties but as I looked closer I saw that it was a pull up diaper not to dissimilar to my younger cousin's ones but this one was clearly quite yellowed on the front. Me Olivia played on their Nintendo switch for hours and after what seemed to be only our fourth Mario Kart race Olivia checked the time and exclaimed "dam it's already eight, we should probably change into our pajamas" Which I nodded too as we walked up the stairs and as we walked past Mia's room I thought I saw another one of those pull ups. "Ollie does Mia still wear pull ups?" I said as soon as we shut the door "oh yeah she still wets the bed" Olivia said nonchalantly "have you ever had to wear them?" I said but I already knew the answer or I thought I did "yeah" she said calmly "what when why?" I said in utter shock "like two years ago cause we where going on a road trip and I had been bedwetting and Mia was wearing them during the day so I had to wear them in the car" Olivia said again very calmly "why do you want to try one?" she said slyly and I surprised myself my smiling slightly and nodding. "I mean what's the harm in trying it" I said after a few moments of awkward silence and Olivia then just walked out her room and came back a minute later with two bright pink pull ups "why did you get two?" I said shocked "well remember our pact, if one person tries something new around the other then the other has to do it as well?" she replied her usual matter of fact voice as she passed me a pink fluffy pull up with Cinderella on the front. As I turned the soft material in my hand I heard my name and as I looked up Olivia announced "if I'm going to wear one of these with you I'm giving you some rules so listen up if you don't want to do this alone" I nodded as she continued "I will get to change you into it first off and I get to pick your outfit until tomorrow morning and lastly you have to keep it on all night except if you shower or go to the toilet, do we have a deal?" I stood with my mouth gaping open but I nodded as she walked into her cupboard. Olivia came out holding something behind her back "you're lucky I remembered I had a bunch of old clothes in here as well as some pajamas cause I don't think Mia would take kindly to me knicking some more of her clothes" Olivia said as she revealed what she had in her hands, it was a pair of her old pajamas which I remember her wearing a few years back, they where white and pink and had a unicorn design on the front and I blushed as I knew she would be putting it on me. Olivia walked up to me and as I stood there she had me pull down my pants and undies and I covered my private parts as she chucked them to the side before grabbing the pull up and having me step into it before pulling it up and having it snuggly around my waist then she grabbed the shorts and once again had me step into them as she then pulled up up around my waist and I saw a slight bulge under the pink pajamas then she lastly helped me into the shirt. Then she turned away and started changing herself and as she pulled up the pull up I smiled that she actually wore it then she put on her shorts which looked like an older version of the ones I wore then she pulled on her long shirt and as I looked down at myself I saw that when the shirt wasn't fully down it revealed the pink waistband of the pull up which I only just now realised how soft and warm it was.