This is a work of fiction. Please let me know what you think and if I should continue Chubbysissy42c@yahoo.com
The Dress
I had spent all of my teen years at an all male boarding school and had become down in the dumps. I was not a jock like majority of my classmates and often had trouble fitting in. The dorms at night just wreaked of teenage testosterone and you could hear the dirty jokes flying everywhere. I was more of a geek and very book smart as opposed to the rest of my peers. I was a chubby kid surrounded by these large jocks that all dreamed of playing sports in college. We barely had any females around our school at all and when one did come by the garnished a lot of attention. It came time for our spring senior play and our professor always had a hard time picking one out that all of the jocks could actually perform in. He came up with the wizard for oz for us. Everyone chuckled at first knowing that the yearly tradition of finding someone to play the female role was now upon us.
It did not take long professor Johnson was texting me that night and asked me to take the lead role. I told him I would think about it that night. My roommate Keith laughed when I first told him but then told me that I will get out of class all the time and they usually throw all sorts of perks at the lead role. It was always a favorite movie of mine and when I awoke the next day my decision was made. It took a week to sort out the rest of the cast but all the guys knew I was going to take the role of Dorothy. Our history teacher made it easy on all the other boys and said she would be the wicked witch. We practiced for the next few weeks without costumes while learning our lines and I was getting into my role. Then reality hit me my professors wife showed up with my blue dress. I could see all the guys snicker as she held it up to me and she told me I would have to come over to get it fitted.
I went over after school the next day and she quickly took me up to her sewing room telling me how much fun it was going to be. Before I knew what was happening she started pulling off my uniform and told me her husband wants me all fitted by that night so we have to hurry. She was a cute chubby woman herself and had on a tiny tank top and bra and little shorts. I kept peeking down her top and could see her looking back at me smiling. As I stood in just my boxers she started measuring me telling me I had a girlish figure and the dress should fit well. Before I knew what was going on she pulled off my boxers and was measuring my hips. My little cock sprung to life quickly and she just ignored it. I was turning red using my hands to cover what I could when she reached out and squeezed my chubby boy boobs. She blurted out that they are nice and big and pointed to hers and said at least they are not this big. Next thing I knew she pulls out a shopping bag full of girls under wear and starts having me get dressed. The panties she chose were baby blue just like the dress and had flowers all over them. Next thing I knew she starts looking at the bras she had picked out and holding them up to my chest trying to figure out the right size. She told me normally we have to stuff the bra but mine are quite nice and perky like a girls. She left me alone in room and I could not stop touching myself my hard on would not go down and the underwear felt great on my chest and bottom. She came back in and had me step into the dress. It was so frilly and girly just like I remembered from watching the movie over and over. It did not take much to get me fitted into it and then came the rest of the outfit. I put on the wig and a bit of makeup. I don't know why but it just felt to good to wear and I loved how I looked. She sent me home for the night but told me to skip my last class and meet her at the house again. Without thinking though I put on my uniform over the bra and panties and took off for the dorms. I skipped along singing and could not wait until the next day.
I walked in front hall and that was when reality hit. I still had makeup on and never took off the bra and panties. I ran to my room hoping no one saw and walked right into my roommate changing from practice. He started telling me about his day and laughed a bit at the makeup but told me I made a cute girl. I didn't know what to do he was not leaving and I could hear all the guys already in bathroom. I sat back and climbed on my bed and listened to him chat away and for some reason found myself eyeing him up and down. He just would not leave and then proceeded to get naked and ready for a shower. He walked out of the room towel around the waist and I jumped up and stared to undress. I was down to the bra and panties and turned around to see him staring at me in just his towel. I never heard him come back in. He told me the showers were full and he would have to wait. I grabbed my robe and put it on and told him to not laugh. He started rubbing my shoulders telling me it is ok that he knows I have to play the girl in the play. He took off and went in shower and I changed to boys clothes taking off the makeup the best I could too.
He never said anything else bad to me and the next day I went to pick up the dress to go to practice with. She hands me shopping bags loaded with multiple pairs of bras and panties telling me it would be disgusting to wear same pair everyday. She helps me get dressed again and grabs my hand and tells me time for rehearsal. She grabs all my things and escorts me out the door in full costume. I felt like the world was staring at me. The breeze felt so good up my dress onto my panties and hard on that would not go away. We got to stage and everyone stopped and looked at me. I could hear some giggles and a few whistles too. No one else was in costume though. That was when he broke it to me that he wanted me in costume first so I got used to being the female role. He then told all of the guys that they were to treat me as a girl 24/7 to help me get ready. I stared at him not believing he just told a bunch of school boys that. When practice ended I was trying to change but quickly realized there was no where safe without showing them that I was in full girly clothing down to underwear. I grabbed my things and begged the professor to use his office he said no problem but proceeded to come in with me.
We started talking a bit and I wanted to change but not in front of him. I sat back in a chair near him and he pulled up next to me. He told me his wife told him I seemed awfully excited to be the lead role and it took a special boy to fill out the girls role around school. He started rubbing my wig and gently touching parts of me and told me what a cute girl I was. He then stood up and started to strip off his clothes right in front of me. He asked if I was going to change as well. I stood up and figured I had to do it at some point. I went to take the wig off and he told me to keep it on. He starts unzipping me and takes the dress off so I am in shoes bobby socks and bra and panties. I turn around and he has stripped naked and has a raging hard on pointing right at me. He starts squeezing my chubby boobs telling me that those are an added bonus. He continues talking and explains to me I have a lot more to do then just be a girl in the play it is a school tradition. He gives me a a kiss on the lips and then pushes me back down into the chair. His cock touches my lips and he tells me to open up. I had seen tons of porn and knew what to do but always saw myself on the receiving end.
I open my mouth and he forces it right in gagging me in process. He keeps talking and fucking my mouth telling me all the boys know about the tradition and that I am going to be busy for weeks. Before I know it he holds his hand to the back of my head and I start choking on his cum.
Shall I continue?