Sorority Boy 22

Well it is the night before Initiation and there is just one challenge left for the Pledge class to face.
Was this going to be the one step too far for Caitlin?

Sorority Boy
Chapter 22

By poetheather

 
Disclaimer:
This is a work of fiction. There should be no way that these characters are like anyone else, but if that isn’t the case, it has definitely been unintentional. Also, if you happen to find that your life is represented in these pages, I’ll be impressed.
 
 
Now that the weekend was here, I was busy getting ready for the party tonight. Supposedly, there was something special about this party and I was a bit worried about what they had in mind as nobody was saying anything. I knew something possibly bad and almost certainly embarrassing to me was in the works by the occasional looks and snickers I was getting from some of the Sisters. I sighed, well, there was nothing I could do about it now except show up and see what they had in mind. I had given my word and there was no way I was going to quit when I was this close.

I headed downstairs and spotted Dawn, who was currently helping Kelly, set up the food table in the dining room. It was going to be another House party with just the girls in the House and any Alums that wanted to stop by and for that I was grateful. I helped with finishing the set up as I had a lot of nervous energy and then it was time to meet.

Everyone from the Pledge class was there, waiting for whatever strange thing was headed our way. Since things were right down to the wire, most of us weren’t talking, just waiting for whatever was next. As if on cue, Nadia came in, “Alright ladies, I wanted to tell you that you have been a great Pledge class and it has been a pleasure to have gotten to know all of you. Now, tonight is the last night before you are initiated into the House. There is a tradition in this House, in this Sorority that was begun by our dear founder as a sort of preliminary… event before your initiation. Nothing mean is meant by this, we have all done this, each and every Sister in the Sorority and you are supposed to have fun going through it.”

Holly raised a hand, breaking Nadia’s stride, “And what is it?”

Nadia sighed and then smiled. “According to one of our oldest traditions, the night before Initiation the pledges go through one last test, to check their resolve to living a new life. So, as such, their Big Sisters will diaper them and the Pledges will be treated like babies for the evening.”

Holy crap? What the fuck? I was stunned as were many others. I know I stood there with my mouth open just blinking in disbelief. Nadia continued, recognizing our looks for what they were, “This event symbolizes the sort of rebirth that occurs when you become a full Sister of this House. It shows a commitment to grow in this House and to become more than you were before. This is the last challenge you face before becoming a member. If you do not think that you would be able to do this you can leave if you want, but that would mean you are leaving the House. I’ll give you a few minutes to decide.”

Nadia left and closed the doors. Once they were shut everyone began speaking at once to the point that I couldn’t really hear myself thinking. Holly quieted us down quickly. “Okay… if this I really the last test, is everyone in?”

Several of the other girls bit their lips in thought. I knew where I stood despite how screwed up this whole thing seemed. I actually wanted to get in this House and this would just be a weird topper to this strange experience. “I’m in.”

Megan nodded, as if that helped her make up her mind as well. “I’m in as well. I think I can do this.”

Alison laughed. “Man, this is the craziest thing I have ever heard of. I totally have to do this or I would leave feeling that I had given up just because things got a bit outside my comfort zone.”

Thuriya frowned, “This is way outside my comfort zone.”

Holly looked over at her worriedly, “Too far outside?”

She shrugged, “I don’t know. To know that all members of this Sorority have done this helps. I have met a few other Islamic Sisters online and if they did this, then I guess I could do this.”

Holly said, “I don’t want you to do something that will make you feel bad.”

“And that is why I can do this. If my Sisters are with me it should be fine.”

Slowly it seemed as if all of us were okay with this crazy idea. We fidgeted nervously, all becoming very aware of each other and ourselves. Nadia came back in when Holly opened the door. “Well?”

“We’re in.”

Nadia grinned, looking honestly pleased with this decision. “Great. This whole thing isn’t that bad… honest, just a bit different. Let me explain what is going to happen. In just a moment, your Big Sisters are going to take you to their rooms where they will change you for the party. Once you are all dressed, you will come downstairs and the party will begin. You will be dressed like this all night, have to drink at least one bottle, then you can use sippy cups, things like that. Then tonight, your Big sisters will put you to bed and tomorrow we have some things to do until your Initiation tomorrow night. Is that clear?”

We all looked at each other and silently conversed with looks and gestures. Holly looked back at Nadia, “Will there be any men around or will we have to go out in public?”

Nadia shook her head. “Nope, you all stay inside the whole time. This is one of the House secret traditions and we don’t share it with anyone not Initiated. Now, shall we get started?”

We all nodded our heads. What the hell was going to happen now? Everything else had been easy but this one really changed things. Soon enough, I was being led by the hand to Gwen’s bedroom, my old room before getting together with Meredith. She gave me a hug once we were inside. “I am so excited Caitlin. You are my first Little Sister. This is cool. Now do you have any questions before we get started?”

“Uhm… yeah… are we able to use the bathrooms?” This was a kind of big issue in my mind, seeing as they seemed to be taking this baby thing seriously.

“No, except in one condition. I know, it’s kind of ooky but I had fun when I went through this so don’t stress over it. Also you get to keep the outfit I got you. It really will be okay Caitlin. A lot of Sororities do something similar, but apparently we go a bit over the top with it, go figure. It’s fun. Do you trust me?”

I sat on her bed and pondered this issue. It was crazy and strange but I guess not as strange as me being in this House at all. I mean a guy in a Sorority? Who would ever believe that? We had all agreed to do this, so why should I balk now? “I trust you.”

“Okay, you get undressed and I’ll get everything ready. Okay?”

“Sure.” With that, I began to undress and I got down to my bra and panties.

She turned around and I could see that she had laid out the usual stuff for babies and there was an adult diaper sitting there on a towel. I closed my eyes and reminded myself of why I was doing this. If I could actually live as a girl and not spaz surely I could do this for one night. Gwen looked at me and said, “Well, you can leave the bra on but you are going to have to loose the panties.”

I nodded and pulled them down, blushing furiously. I was wearing the new vagina that Meredith had made for me, because it made me feel… I don’t know… safer some how but I did feel just as exposed.

She laid me down on the diaper, helping me get centered on it correctly. It felt strange and I told myself that it would be okay. God, I hadn’t felt like this since this whole thing started. She covered me in baby powder and then she closed it up. Once that was done she helped me up. “Ready for your dress?”

She went to the closet and pulled out this baby pink dress with frills and ruffles all over it and the outfit looked like something you would put on a doll, not on a person. I felt like I was seeing someone I knew pulling out an evil magical item to use it on me. “Hurry up, we need to get downstairs.”

She put the evil dress on me and made me step into some loose lacy panty things. I felt like an idiot. Then came lace ankle socks and Mary Janes. Once I was properly dressed, she was messing with my hair doing something to it; my guess was giving me pigtails. Once she was finished with that, she clipped a pacifier on the dress and stood back to look at her work. She squeed, “You look so cute.”

I groaned. Of course, it had to be cute. She took several pictures and then led me downstairs to get to the party. I got to see all of the others there. Alley was dressed like a gothic baby, which was impressive and amazingly enough, looked fairly normal on her. Devin was in a dress with Barbie on the front and seemed amused by this. Megan’s had My Little Pony on it and she was blushing furiously. I guess the Big Sisters did put some thought into this in terms of getting clothes for us, but why was I stuck in something so obnoxious. The last few stragglers came up and then we were all there, dressed like big babies. It was strange and we all fidgeted nervously.

Sandra came up then and looked over us all, smiling, clearly pleased with things. “Your Big Sisters should have explained everything to you by now. Stick to your Big Sisters and have fun.”

Then the party started. The other Sisters of the House came by and oohed and ahhed over us quite a bit. I felt very strange when several of us were photographed time and again with different sisters. Meredith came by with a bottle and handed it to Gwen. Gwen smiled and handed it over to me. “Here you go Caitlin! Have fun with your nummy baba.”

I took the bottle, looked at it, looked at Meredith and Gwen who were looking intently at me, to see if I would do anything. I sighed, realizing that I might as well get this over with. It took me a while to get the nipple working, as it was not an easy thing to get the hang of but then I got a taste of what was inside, some sort of chocolaty almond drink that had me moaning happily. I kept pulling at the bottle, trying to get more of the tastiness out. It was good and motivated me a lot more than most anything else might have.

I brought the bottle down. Gwen grinned at me, “Will that work?”

I nodded, “This will work.”

Once the drinking began, the fun really started. About an hour into the party, it turned out Holly was the first of us to be changed. The Sisters sang a silly song about it while Holly stood there blushing, being led out by her Big Sister. Esperanza was hamming it up with Brittany, having a lot of fun and seemingly had few issues with all of this. It was probably a Buddhist thing.

Brittany was next and she sang along with the other sisters, having apparently picked up the song after hearing it once. She even did a little dance which made me laugh, which had the unfortunate consequence of me needing a change right afterwards.

As Gwen led me out of the room, the song started again and I had to laugh about it. Okay, despite how screwed up I looked in this dress I was having fun. The various girls were coming together thanks to this and I was meeting girls I hadn’t been introduced to yet, as well as a number of Alums, who were telling me stories of their Baby Night. The Sisters of the House were clearly having a great time as well. Maybe this wasn’t as bad as I had thought.

After my second bottle, I had apparently upgraded to a sippy cup, which was nice as I wanted to have more of that chocolaty goodness. At some point, I was talking to Alison, who was amazingly adorable. Somehow her Big Sister had gotten baby style bows for her pigtails that were black and had skulls on them. I had never even thought that there even could be something like this. “I have to say, you look great Alley.”

“Thanks Caitlin. This dress isn’t so bad. You know, this outfit is great and I am definitely going to be wearing to the club a few times to get some extra wear out of it. I am sure that it will get a lot of comments.” Alison looked pleased by this.

“I look like a frickin doll in this.” I grumbled.

“You look cute Caitlin. All of us do, so just relax, have a drink and enjoy.”

It was then Amy’s turn for a change. Alison and I joined in on the song, then giggled. Okay, that part was kind of fun. The song was cute and certainly helped break the mood, keeping things fun rather than embarrassing. “So how are your classes going?”

“Not to bad. I am leaning more and more towards Linguistics, as it is really cool and the teacher for the Intro class is pretty nice, even though he is a TA.” She took a drink out of her sippy cup.

“Cool. I am still a bit unsure about what I am going to do. I have been looking at some of the major non-profits out there and they look good and I guess being a lawyer would help me out there. What do you think?”

She looked thoughtful for a moment, which was cute because of the pigtail bows. She was incredibly adorable in that outfit. “Look, don’t worry about that yet. Follow your bliss and try to figure out who you want to be. The rest can be taken care of later.”

We both paused, and I looked down at myself and then back up at her. We started laughing. I tried to speak between laughs, “I… I am working… on it.”

Gwen came by to check on me, looking at the two of us quizzically. A lot of the order of the party had faded by this point. “Need a refill?”

I shook my head, “Not yet. I still have plenty.”

“Need to be changed?”

“No, I’m good.” I smiled at her.

We then drifted towards the food, as I was getting hungry because I hadn’t had anything for dinner. They had all sorts of finger foods laid out and it was impressive. I had some of the sandwiches and a few of the gyoza and pirogues. It was all pretty tasty and very filling.

Things grew blurrier as I had more of that drink. After my second or third change, there was one point where the whole pledge class was dancing together to YMCA, giggling at the way our dressed bounced along with us. It was a hoot. I knew there were lots of pictures and video taken of the event, but I could barely remember who had taken pictures of who.

There was one other bit of fun during the evening. At some point, all of the members of the Pledge class had pictures with our Big Sisters and then one with the whole Pledge class together. I was looking forward towards getting to see how the pictures had turned out. I was sure they would be really cute.

When I was stumbling and yawning, Gwen took me back to my room. She changed me, hung up my dress, and put me in a cute nightgown she had gotten that was also the same color of pink. When I lay down, I pulled my bear into my arms. It had been a weird night but I had to admit it had been a lot of fun. A hell of a lot more fun than I thought it would be when the night started. I yawned again and then closed my eyes. I fell asleep as only the drunk could. I was probably snoring for all I know. I cuddled my bear to me as I fell asleep.



To Be Continued...
 



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