Humiliating Halloween
Copyright© 2008 by SBW
Chapter 1
One of the things that turned me on to my girlfriend Gretchen was my appearance. Even when the two of us met during my first week of college, it would have taken very little to transform myself into an early teen. The things I hated about my body, Gretchen loved. On a good day, I reached 5 feet 2 and when we met, I weighed about 115lbs. My boobs, while quite firm barely filled my 32a bra and in high school, guys and girls alike remarked on how I looked like a 12 year old boy (I should have never got the short hair cut.) I had boyfriends from time to time but my junior year experimented with girls. That was even worse for my reputation so I dated a nerdy boy my whole senior year.
In college, I went to where I knew no one and wanted to get back to my true love. I met Gretchen and quickly took a liking to her. A few years older, we hung out at a lame party and then she took me back to her dorm room. One of the things I liked about her was the fact that, unlike me, she was very upfront. She told me she wanted me to be her girlfriend but that certain rules would be set down from day one. I was shocked when she basically described that I would become her submissive. While I had heard of such stuff, it floored me. She promised to always look out for my best interest but stated, I would obey her, no questions asked. Amazingly, nothing turned me on more than these words and the rest is history. Since the school paid for our dorm rooms, she moved me in with her and we used my room for storage or occasionally for other things I'll tell you about later.
The first thing that Gretchen did was controlled my diet and exercise. It took me about 4 months to reach her goal of 95 lbs. Since we met after I started college in the summer, by Halloween I was in shape up to her specifications. It was then she planned a humiliating experience for me.
I got home from class and as was expected stripped naked. Gretchen usually left instructions for me on the table. When I got there, there was a box with a note: "Happy Halloween. Tonight, you are going to go trick or treating in the costume I chose. Shower and shave, especially around your privates, and then you may open the box and dress. Love —G" I was so excited that I ran into the bathroom and followed her orders. I then opened the box and was a bit shocked. Though I have been humiliated before, this was extreme even for her. There was a tiny halter top with a peace sign. Yes tiny even for the 12 year old boy and a very short black skirt along with sandals. As I dressed, I heard the door opening and quickly fell to my hands and knees. The breeze I felt across my bottom reminded me how short the skirt was and there were no bra or panties to be found. Gretchen smiled as she looked down at me and then lifted me to the bed. She kissed me and then braided my hair. After that she got a black marker and wrote HIPPIE CHICK on my belly and handed me a plastic pumpkin.
"You look nice, sweetie. I have never seen your boobs look so big. I am going to drop you off in a neighborhood and you will get candy. At each door, you will say 'Trick or treat'. If anyone comments about you being too old, you will lift your skirt, show your pussy and say 'No I am just a little girl' You will do this every time you are asked unless children are at the door. If you are questioned further, just pretend that it is me asking you questions and answer appropriately. Understand?" My face was so red when I muttered "Yes Maam" and I was escorted to the car. I was blindfolded and we drove about an hour to a neighborhood I didn't recognize. I was unblinded and told to meet her at Jerry's Pub in two hours after she was done. I don't know if it just seemed so or if a lot of thought went into the choice of neighborhood. There were lots of houses with the porch lights on but only a handful of kids around. It was cold and a bit windy and my nipples were hard. I stopped at a few houses and got some candy and dirty looks. It was when I got to about the seventh house when things changed.