Compromising Situation Part 3

I quickly found some new sweatpants to put on and after pulling them up, I took off my socks and placed them in the bag in my drawer. After closing the drawer, my roommate walked in. "Who was that?" he asked referring to the girl that walked out of my dorm. "This girl I met, she wanted me to go on vacation with her and her family." "Nice," he exclaimed "me and my new girl are actually leaving tomorrow morning to go on a vacation of our own, so I guess I'll see you after break." He finished filling his backpack and headed out the door. It was only Wednesday, so I still had a few days here. Since my roommate was gone, I decided to go to bed; pulling off my sweatpants, I climbed up and fell asleep.

The next few days were uneventful, I woke up wet on Thursday but disposed of my diaper like the other day and got ready for school. I wore the panties under my outfit and nobody noticed. When I got back from class, I changed into a diaper, did some homework and then went to bed. I woke up Friday, this time dry. I still disposed of it on the way to the showers and wore my panties to classes. When I returned to my dorm, I changed back into my bedtime clothes.

My phone rang, it was Em. "Hey we will pick you up in like 5 minutes, we decided to go shopping tonight to get you some vacation clothes."

"You can't buy me clothes" I interjected.

"Believe me, my mom received a lot of money in the settlement so it's our treat." she responded. "Pack whatever you need in your bag, then wait for us out front." *click* she hung up.

I pulled out my diaper back pack and threw my toothbrush in their. Since I don't need clothes, I guess this is it. I threw on a tshirt and headed outside. After a few minutes, Em's van pulled up. The door opened. "Hey!" I was greeted by the family. I went to the back seat and sat down. "Since we are shopping for Sarah, I thought you should be dressed as her. There is a bag back there with some clothes you can change into on the way." I looked at the bag, "I guess break starts now" I thought to myself. I pulled the clothes out of the bag:

http://www.sportsdirect.com/hello-kitty-kitty-joggers-infant-girls-305021

http://www.shirts.com/tween-hello-kitty-cute-meets-smart-tshirt.html

"I know you have undies and socks, so I just packed the sweatpants and tshirt; just change in the back right there" Em said.

I took off my shirt and put on the new one, then I slid down my boy pants. I started to take off my diaper to put on my panties but I was stopped. "Your pants should cover that fine." I slid on the girl pants over my diaper. I put on my socks from my backpack next, and put my Nike slides back on.

We spent the rest of the time talking about school and about what we planned to do in Florida. From what I took in, we were going to be staying at a hotel near the beach and we were going to go to a concert as well as Disney World. We were going to go to the different parks on different days; I was excited for this as I have never been there before. The ride went by quick and next thing I knew, we were at the mall.

We all stepped out of the van, Em grabbed my hand and started leading us inside the mall. I realized that they didn't do my hair and make-up, so my face still looked the same. I asked Em what to do, she said that I kind of looked like a girl so people I didn't know wouldn't even know. She told me to walk with my head down, so people that I did know wouldn't get a good look at my face. I was nervous, but Em seemed confident so I decided that she must know what she was doing. I kept my head down as Em led us through the mall.

"Let's start with the basics, we will be gone for 2 weeks so you will need socks and underwear. What should we get?" Em's mom asked, looking at me.

"Well I have a pair of XS, but I liked the way the size 8 fit better" I said unsure how I felt hearing myself say that.

"Well all the size 8s are here, so pick what ever you want" she said.

All of these looked like they were designed for children, so I am assuming size 8 was not for adults. I did like the way they felt however, so I decided to roll with it. My underwear went under my clothes anyway. "These ones I guess" I said pointing at a package.

http://www.jcpenney.com/total-girl-10-pk-hipster-panties-girls-4-14/prod.jump?pp...¤tDim=Childrens+Sizes¤tDimVal=8&_dyncharset=UTF-8&colorizedImg=DP0703201517022889M.tif

These were the ones with the most boy colors. "Okay, well there are ten here so you should have enough for the trip; just make sure you don't ruin them" Em's mom said picking them up and placing them in our cart. "Now let's find you some socks. We walked over to the next display. "You will need to pick a bunch, I don't know how often we will do laundry. Which ones?" I quickly pointed to all of the fuzzy socks, those were my favorite. "We can get you a few of those, but it is going to be hot down there, so maybe we should pick other ones too."

I didn't know what I wanted, so I told her I didn't know or care. "Do you just want me to pick all of your clothes for you?" Em's mom asked. I really didn't enjoy clothes shopping for boy clothes and I cared less when it was for girl clothes. "Yes" I responded. "Okay, well did you like the way everything fit this weekend?" "Yeah, maybe the swimsuits and outer clothes could be a little bigger" I responded. Em's mom said okay and told Em to take me to the dressing room and she would be over there with some clothes in a few.

We walked over there and sure enough, in a few minutes Em's mom was back with a full cart. The lady at the dressing room said we would could only take in a few at a time, but said she would watch our cart. Em grabbed a pile of clothes and we all headed into one of the stalls. I asked if Bri had to come too, but her mom said that she couldn't be left alone outside.

For the next 30 minutes, I was like a model. Em's mom kept leaving and returning with more piles of clothes for me to try on. For the most part, the clothes fit and after everyone, Em's mom asked if I liked it. I has a realization that I was going to be spending 2 weeks dressed like a girl; I guess that it didn't really matter what I wore because I wouldn't love any outfit. As long as they fit, I told Em's mom that whatever was fine. The designs ranged anywhere from plain, colorful, Hello Kitty, MLP, all the way to Disney and Disney Princess. Em's mom said that I should get a lot of Disney stuff since we are going there. I tried on tshirts, sweatshirts, dresses, skirts, leggings, shorts, overalls, and swimsuits. Em insisted that if I was really going to see if I liked being dressed as a girl, I should try it all.

It was strange changing in front of everybody, I tried using Em as a shield the first few times. I was still not used to people seeing me in a diaper. After changing so many times, I just gave up and stopped caring. This was one of my low points in life, but I was in too deep to change my mind now. After trying on the last outfit, I put my original clothes back on we shopped around for Em and Bri now. I wasn't even sure what we all picked out for me; but I guess that we would find out when I needed an out fit for the day. After hitting all the stores in the mall, we exited. I calculated an estimate of the total amount of money we spent in the mall and it was well over $700.

Em's mom loaded the bags in the back and we took off. Before we went back to their place, we stopped at CVS. Em's mom told us to sit tight and she ran in. She returned and threw a box into the back seat. I looked at the box.


http://www.mumzworld.com/en/pampers-active-girl-value-pack-size-6-33-diapers

"These look too small to fit me" I protested. "Plus I already have some"

"These ones have tabs so they are easier to change and they are the largest size so they should fit. We just want to make sure we have enough." She responded.

Enough? How often did she think I was going to be diapered?

We ended back up at Em's house and we walked out of the car. I asked if Em's mom needed help. She said that she would pack my bag tonight and that for now everything could stay in the car. She said that we should get ready for bed. I asked about PJ's. Em's mom said that since everything was packed that I could just sleep in the clothes I had on. I followed Em to the bedroom and got ready. She took off her clothes and climbed into bed wearing nothing but her bra and panties. "Are you coming?" she asked.

I started to climb up. "You are going to wear those sweatpants? I better wear some pants too". I told her that she didn't have to and that I was actually just about to take these off. She agreed, so I slipped off the pants. I was now climbing up in nothing but a diaper, socks, and t-shirt. I laid down next to her and she threw some covers over us. She then turned her back to me, reached behind her and pulled my arm over her. I put my arms around her and pulled her close, placing the front of my diaper up against her backside. I nodded off to sleep.

I woke up and noticed that the room is empty. I climbed down and walked out the door to the kitchen. I was greeted by the girls. "Good afternoon!" they said. I looked over at the clock and realized it was 12:15. I got nervous, when does the flight leave? I asked. "Do not worry, I got us a later flight." Em's mom responded. "We have to do somethings before we leave."

"Wow, you must have been thirsty last night." Bri exclaimed. At first confused, things started to make sense as I looked down. My diaper was sagging tremendously. I covered myself with my hands. Em's mom noticed and tried to cheer me up "It's okay, that is what they are for".

"We have to get you ready to go anyway, so follow me." she said grabbing my hand.

We went to the bathroom and she started the tub. She told me to take off my diaper and throw it away. I did as instructed. She said that since I was all packed that I would have to wear the dress that I wore the other day to the airport and the socks and underwear I brought with me. First, lets get you shaved and do your make up. We went through the same process as we did on Sunday, except she used pink lotion on my skin after shaving. She said it would help to make sure it didn't grow back as fast. She didn't do my hair though.

Next, Em came in holding the dress and my socks and underwear. I got dressed and entered the living room. The girls said that we were all set and ready to go. I put on my slides and entered the van.

We had 1 more stop to make, Em's mom said. We stopped at a house.

We walked into a hair salon and Em started to talk to the lady at the front. Em's mom explained to her that we were going on vacation and that we all wanted our hair done before we left. We then followed the ladies to the back. We all sat down. The lady went to work, straightening and placing other products in my hair. It wasn't until she pulled out the scissors that I asked what was going on.

Em's mom explained that it was so that people wouldn't suspect anything on vacation and that when we returned I could just get a haircut. Knowing that I wouldn't win this battle either, I agreed and let her continue. The ladies finished up what they were doing, adding some finishing touches. She placed a headband in my hair with a bow on top. I looked in the mirror, there was no way I was getting mistaken for a boy, I thought.

Em's mom paid the lady and then we headed to the airport. We got out of our van and emptied out the back. Em's mom had packed me a large suit case, a duffel bag, and a backpack. We went and got our luggage checked and walked through the metal detectors. This took a long time. After that we went to our boarding area. As I was sitting there, I was noticed that it was getting late. We had eaten before we left, but that was at like 2. It was now around 830. I asked Em's mom about dinner. She said that she had completely forgotten and decided that we could just eat at Wetzel's Pretzels. We got our food and sat back down.

We ate and talked, each minute we started to get more and more excited about the trip. I got so excited, that one time I threw my hands up. This caused the cheese I used for my pretzel to flip and spill all over my dress. Em's mom told me to follow her so I could get cleaned up. I followed her into the bathroom.

There was a long line, so we waited outside. "I was going to save this for the plane just incase you got tired; but I bought you pajamas. They will definitely be more comfortable and it might be easier to change in here than on the plane." Her logic made sense, so I agreed. We finally got to the front of the line and a stall opened up. It was one of the large stall. We both walked in and she unzipped her carry on bag. A took of the dress and handed it to her. She pulled out something from her bag- it was not pajamas though.

"I think that since it will be a long flight and that since you might fall asleep we should be careful. I know that you have been having accidents in your sleep so we are going to put one of these on you just in case. It was a diaper- not like the pull ups that I had been wearing, but a diaper from the box she got yesterday. I didn't put up a fight. She went to the wall and opened the thing on the wall. She then told me to sit up there. I did as was told and sat on the plastic. She then told me to lay down, so I put my head to the edge and let the lower half of my body to hang. She slid off my panties and place them in the bag and unfolded the diaper.

She lifted my legs and placed the diaper under me. She then doused the diaper and the region it covered in baby powder. After that, she tucked myself between my legs, then pulled the front of the diaper up. She reached for one of the tabs and stretched it as far to the front as possible and put it in place. She then did the same for the other side. She told me to stand up and asked if I was good. "It is really tight" I said trying to take a step. I couldn't really walk right though, so I had to waddle a little. "That's okay, it makes sure that there are no leaks. This one will hold more."

She reached back into the bag pulling out something else. "I know that you said that these felt good, so I figured I'd get you your own special PJ's" she said handing me something.

http://www.kohls.com/product/prd-2129892/carters-cupcake-footed-pajamas-girls-4-...

These will fit a little bit better, they are bigger than Bri's. I looked at the footed pajamas, then down at my diaper. Dora was staring back up at me. I decided to put on the PJ's so she wouldn't stare at strangers. I went to lift my leg, but could only lift it to the side since the diaper was so tight. Em's mom noticed my struggle, so she picked me up sitting me back down on the table. She placed my feet in the PJs and stood me back up. I placed my arms through the holes and looked for the zipper. It was all the way down at my feet. I bent over and zipped it up. I started to walk out of the stall, but was waddling really slow and clumsily. "Here I'll make it easier" Em's mom said lifting me up and carrying me like a toddler. We exited the bathroom, returning to the girls.

"Those look cute" Bri said. "And comfy too" Em chirped rubbing my back as her mom held me. She reached my diaper, I felt her hand stop. "All ready for the flight" she said patting my diaper. "Yep" Em's mom said as she starting bouncing up and down. I turned away from Em, hiding in shame and placed me head on her mom's shoulders as the bouncing was making me nauseous. Em's mom started to repeatedly patting my diaper, the sound was taunting me. I closed my eyes that way I didn't look at anybody.

I was in a diaper and footie pajamas being held like a baby. At least we were going to Florida I thought to myself. While this was happening, I noticed that my body was becoming less tense and how soothing the bouncing and patting felt. With my eyes closed, I ended up falling asleep.


I woke up, Em's mom reaching over me, fastening my seatbelt. I looked around, the plane was crowded; there appeared to be no open seats. After Em's mom fastened my seatbelt, she walked away. I was sat in a window seat, Em sat next to me, then Bri sat on the outside of our section. Em's mom sat behind us as there were only three seats per row.

I looked at the reflection in the window, it was no longer me but Sarah. Sarah had a pink flower clip in her hair and her makeup done; she had all of my facial features, but for some reason she looked nothing like me. I was a boy but Sarah was definitely a girl. I had to remind myself that I was actually Sarah. I looked down at my clothes. My body was covered neck to foot in purple fabric decorated with cupcakes. Looking past the design, I realized how comfortable my current outfit was.

The cotton fabric kept my entire body warm, my socks tickled my fit, and even the diaper I was wearing -while tight- made me feel secure. I looked over at the girls, we hadn't even taken off yet, but they were already fast asleep. I couldn't really blame them though- I had already fallen asleep once and it was getting really late. Em's head leaned over on my shoulder so I placed my head on hers, closing my eyes and falling back asleep.

I woke back up and looked around, everybody was still sleeping. I had a familiar feeling but couldn't put my finger on what it was; that is, until my stomach rumbled- and no, I wasn't hungry. I had to release my bowels. Em was still leaning on me, I looked down and tried to unbuckle my seatbelt but couldn't get it. I hit my button that called for a flight attendant. She arrived shortly, "can I get you something? A pillow or a drink?" she asked.

"Can you tell me how to unfasten my seatbelt?" After her explanation, I freed myself. I slowly stood up and snuck past the girls. I forgot that I couldn't walk very well, but I slowly waddled to the bathroom. It was occupied so I leaned against the wall and waited. A couple minutes later the door opened and the man inside exited. I entered the bathroom and shut the door behind me. There was not much room in here at all. I started to unzip my pajamas and got about halfway down until I realized that I could not bend over. Since the bathroom was so small and my diaper was so tight, I struggled to lean over and unzip my PJs the rest of the way. I slipped my arms out and started to wiggle my clothes off, exposing my diaper. I looked down and noticed the tabs. I couldn't slide these ones off and if I undid the tabs, I wasn't sure if I could refasten them. I did not want to go back out there and ask Em's mom for another diaper or to change mine; especially since there was no room in here so she would have to change me in the open.

After weighing my options, I decided that it may be best to use my diaper for its intended use. I sat on the potty, since I couldn't keep my legs together, which caused Dora to stare at me once again. "Sorry" I whispered to her, not believing that I was actually choosing to mess myself. I thought about the consequences. It might smell out there, but I didn't think we had much time left in our trip. I closed my eyes, that way I didn't have to look Dora in the face. I pushed and relieved myself. It took me a little bit but I think I got it all out. The diaper pushed back when I was pushing out, so I could feel the waste spreading all over my backside. After, I sat in defeat. I sat there for a while, not wanting to go back out there; however, the flight attendant knocked on the door asking if I was alright. I said yes and struggled to pull my jammies back up. I headed back out to the plane. I thought walking was hard before, but it was nearly impossible now. I waddled back to my seat. I slid myself back to my seat, making sure to keep my smelly backside out of the girls face. I sat back down and buckled up.

I couldn't fall back asleep, but shortly the flight attendant began walking around waking people up and telling them to buckle up. I must not have smelled too much because nobody had said anything. We landed after a few minutes and were told to exit our flight. We stood up and Em grabbed my hand. Em's mom exited right behind us and noticed how bad I was struggling to walk. She decided to pick me up and walk me off the plane. When she did, she noticed what I had done a few minutes earlier. "We are going to have to get you changed" she said.

Eventually, we exited the plane into the airport. We waited for our luggage at the carousel, when it came, Em's mom grabbed hers and asked Em to get mine. Em's mom looked for the closest bathroom. We found one with a long line but the girls were ready to leave. "We have to get our rented car anyways, so you wait in line with him and I will do that. If I finish before you, I will wait for you outside the restroom." She set me down and started to dig in her carry on bag. She handed Em one of my diapers, told Bri to help grab our stuff, and headed to get our car. Em looked at the diaper, placed it at her side, then grabbed my hand with her free one. I started to waddle slowly and she became impatient. She really wanted to go back to the hotel, so she picked me up and started to walk to the bathroom.

"I can't wait to go back to sleep" she said. "It'll be much more comfortable than the plane. We will have pillows, blankets, a soft bed, plus we will be able to snuggle". I looked at her, then back towards the ground. I really liked her and she really liked me, so I knew I had to overlook the fact that she was carrying me to go get my diaper changed. We waited in the back of the line. We talked about what we were most excited for on the trip and she told me how glad she was I came. After what felt like an eternity, we still hadn't moved much. Em's mom had returned with Bri, the luggage, and car keys. "Wow, you haven't moved much, it might be another 30 minutes before you get inside." Em's mom said. The girls groaned. I didn't want to sit in a dirty diaper all the way back to the hotel, but I also didn't want the girls to get mad at me for making them wait. "I can just get changed when we get back to the hotel" I chirped.

The girls were totally on board with that idea, so Bri and her mom grabbed the luggage as Em carried me out to the rental car. We approached a van, much like the one they had back home. We loaded up the car, our bodies included, and headed to the hotel. The smell coming from my diaper filled the van which made everybody roll their window down. I realized that I had to go potty again and thought I should hold it. Then I remembered what Em's mom had said about this diaper holding more, so I decided that maybe I should just go. I wet myself. The warmth filled my diaper.

We pulled into the hotel. Em's mom told the girls to get the luggage and that she would check us in. She then picked me up and headed inside. I didn't want the people there to know that I was being carried because I couldn't walk with my diaper, so I pretended to be asleep. The girls came in behind us. We finished checking into the hotel and headed to room 127. Em used a key card to open the door and we piled in. Em's mom sat me on the bed closest to the window and said that would be mine and Em's bed and that her and Bri would have the one closest to the door. Our bags were scattered on the floor. The smell began to fill the room. "Go start to get your PJ's off and I'll be in the bathroom to change you in a minute" Em's mom stated.

I waddled into the bathroom. When I entered, I stopped to look in the mirror. I then unzipped my jammies half way down like I had done earlier and slid my arms out. I saw that Dora was trying to peek her head out. I then wiggled my hips which caused my jammies to hit the floor. I looked back up in the mirror and saw how bad my diaper was sagging. "Lay down" Em's mom said entering the bathroom. I laid back on the cold tiled floor. She ripped the tabs off causing my diaper to plop to the floor. I asked her if it had leaked. "Nope, you had room for plenty more. I told you they held alot" she responded. She continued by lifting my legs in the air, wiping my bottom and front with a baby wipe. She folded up my dirty diaper and slid a new one under me. She filled it with baby powder and re-diapered me, pulling the tabs tight again. She then put me back in my jammies and zipped them up. I waddled out of the bathroom and saw Em putting the last of our clothes in the drawers. I went to her. She pulled open the top drawer, "These clothes are yours" she said as well as the ones hanging on the left side in the closet." "Now let's go to bed, I whooped" she said kissing me on the forehead. She began to take off her clothes, changing into her pajamas. I climbed over into our bed.

She climbed in shortly after, wrapping my arms around her and pressing my diaper against her bottom.

I woke up. Bri was sitting on their bed watching Spongebob. I sat up and heard Em and her mom in the bathroom. Bri must have already gotten around for the day. I started to watch TV. I know that Spongebob was meant for kids, but it was kind of funny. Em came out of the bathroom. "Good morning sleepy head" she said kissing my cheek. "Good morning" I said. "Go pick some clothes for the day. Me and mom are almost finished, then you can get in here. We are going out to breakfast since we slept in past the hotel's breakfast times. After you shower and change, we will teach you to do your hair and makeup." Em then headed back to the bathroom. I got up and went over to my drawer. I had no idea what I should wear.

I decided to start at the underwear as that was the easiest choice. I just grabbed the first ones on the pile. It was the one with the stars from the package I picked. They were white with pink elastic bands. It was covered with purple, green, pink, orange, and yellow stars of various sizes. That was the only thing that I picked out while shopping. I then decided that since we were in Florida that it was probably warm. I should either wear a dress, skirt, or shorts. I picked up a skirt since I remembered liking the feeling of the wind when I was wearing a dress and I knew that nobody would recognize me down here. I grabbed the first skirt I saw:

http://www1.macys.com/shop/product/jessica-simpson-girls-plaid-skirt?ID=2352101&...

Next I needed a top. I looked for something that matched my skirt. I decided that the white shirt with pink sleeves should do.

http://www.jcpenney.com/disney-frozen-graphic-raglan-tee-girls-7-16/prod.jump?pp...

I saw that there were some white flip flops with a large flower on top of the toe divider. I thought that those would go good with the outfit I picked out. I grabbed my clothes and sat them on the bed. When Em and her mom were finished, I entered the bathroom. I got inside and closed the door. I then started the process that was taking off my jammies with a diaper on. After I slid them off, I looked at my diaper. It was soaked. I had wet myself in my sleep again without realizing that I had, I had painted Dora's sky yellow with urine. I took off my tabs and folded up the diaper like I saw Em's mom do the night before. I placed the diaper in the trash can, right next to the one I had messed yesterday. I then hopped in the shower and showered. I was hungry so I did that quickly. I rubbed the soap on my skin, which was still smooth so I wouldn't need to shave again. I hopped out and dried off. I slid the star undies up my legs and onto my waist. I then slid up the skirt after. Next I put on my shirt and headed out of the bathroom.

The girls commented on how they liked my outfit. Em and her mom led me back into the bathroom and showed me how I should brush my hair, which way to part it and how to put a clip in. They then took it out and asked me to do it. I did it and it didn't look bad, but I asked if they could do it again so it would be perfect. Em's mom said that she would just show me another hair style. She proceeded to show me how to put my hair in pigtails. She placed the two hair ties in my hair. Next, they showed me how to apply makeup. Lipstick, eyeshadow, blush, eyeliner, the whole nine yards. Finally, they showed me how to paint my nails, both my toe and fingernails. Since I was wearing a pink outfit, we used the nail polish that matched. We let my nails dry and then I proceeded to put on my sandals. We were ready to go to breakfast. It was the first day in Florida with us four girls...