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I Was Crossdressed At School

The Initiation

By: bobbie13
Written on May 25th, 2010
By: bobbie13
Age: 56-60 , Transgender
7,214 people have read this story

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14 responses
  • jennylee911

    My sissy girl wore girls slacks and tops over his lingerie all thru his school days. He actually wore a prom dress to the prom, but was not allowed to enter. He has grown up a a sissy girl and is still one today under my comands.

    May 12
    1 like
  • boyfromwhiterock

    This story reminded me of when I had to go up to high school and that was the intiation rule. Boy had to dress up as girls for the day, come to school as girls and leave as girls. I was forced to put on a wig, makeup, short skirt, blouse, bra, panties, pantyhose. and shoes for the day. It will be a day I will never forget

    Dec 14, 2012
    1 like
  • whitchwyman

    I wish that I could have gone to that school

    May 11, 2012
    1 like
  • WPDP

    Your story reminded me of freshman initiation in my school. I went to a Catholic school which had a week long freshmen orientation program. Upper classmen would auction off the freshmen. There was always more girls than boys, so the boys were always sought out first. Orientation consisted of the routine items and the final day was called "freshman frolic" for obvious reasons. The highlight of the frolic was a mock pageant where the guys would be dressed up for a mock beauty pageant. It was a tradition, and the nuns made sure it never got out of control.



    Even before the orientation started I knew who was going to be my upper class mentor. A neighborhood girl told me she was going to pick me because I was the right size to fit into some of her things. She even told my mother of her intentions and my mother's response was for her to come visit us so we could make sure everything fit right.



    The next day, she came over with her mother and armloads of feminine clothing. My mother took control of the situation and she had me wear a girdle to hide my male parts, a bra, and a slip. Then the others would have me try on things and have me parade up and down the room. There were two long prom dresses and a knee length special ocassion dress. There were petticoats, stockings, and make-up. There were shoes too, but even at 13 years old, my feet were too big for them. For the most part, I could fit into everything except the shoes. They decided on a dress, and then took it back, to make some minor alterations.



    On the day of the event, I dressed for school wearing a girdle and bra under my school uniform. My mother came up with some shoes and a wig and passed them on to my upper class mentor. The pageant wasn't scheduled until after lunch. At that time the girls passed garment bags to the guys and the guys would go into a dressing room to dress up.



    Some of the guys had a terrible time trying to fit into their dresses. Most of them just tried to pull the dresses over their guy clothes, and then they couldn't zip up their dresses. When a guy thought he had done all he could do, then he would step out of the room and ask the girls for help. The girls would then fix them up the best they could and add make-up.



    As for myself, I was over-dressed. I had everything and it fit perfectly. I even wore all feminine undergarments. Few guys had wigs and shoes. So, I was one of the last to step out of the dressing room. When I did several girls squealed, and I received my make-up, including nail polish.



    The pageant was simple enough, when the MC called your name you just walked pass the student body, and presented yourself before the judges (nuns), bowed and answered a couple questions from the judges, and walked back. Then after all contestants had their presentation, we all walked on stage for the judgement. They would thank all the contestants, announce the "best dressed", "best smile", "best make-up" etc. so everyone got some mention. Then they would announce the top three finalist, then the runner-up, and finally the winner. The students would all be cheering for each announcement and we all had a lot of fun.



    Needless to say, thanks to my fine support, I won. I received a little tiara. While the others were told to get dressed back into their own clothes, I was asked to continue wearing the costume, as I was the winner. Good thing too. I couldn't remove the nail polish. And my mom got to pick me up after school still in my prom dress. She had me remove it when we got home, but the neighborhood girl did NOT want the dress back. So it sat in my closet for years after that.

    May 11, 2012
    3 likes
  • dlferris2012

    I like your story. If you were entering secondary school, wouldn't you have been about 14 then?

    Jun 26, 2011
    2 likes
  • theBillyandBudBear

    I haven't as yet read what happened to the kids who humiliated you so horribly? Did all the parents and staff this this was just so cool? Were none of your teachers educated professionals? What was your parent's take on all this, especially shredding all your boy clothes. Did anyone have to replace or pay for them?



    Did no one press criminal assualt charges against those kids, or sue the School Principal and the District? This was clear and simple as sexual assualt in a bathroom by a mob!



    Just curious to learn the rest of the story!



    In my case, eventually that Nun punished the wrong boy almost as horribly as she punished me and well, that boy's parents were outraged and powerful enough in the neighborhood and that Nun was banished to a Convent and never taught children again.



    These days I am actively involved with standing up to school punks and bullies and have assisted many parents in bringing successful law suits against school officials and Boards of Education, the parents of bullies that allow the bullying and humiliation of other students.



    It's not about "suing" but about waking up school officials and parents, and law suits definitle get their attention in a hurry.

    Feb 15, 2011
    1 like
  • emil2009

    I am sure with this experience you became very wary of going into boys restrooms, not knowing what to expect. What the boys did was totally wrong, I am sure you did not want to be exposed like this at school, putting your secret out their to be chastised. I don't like to read about boys that were forced to dress-up, my early feelings were nothing like that, my feelings came from infatuations of everything girlish. Please let me know either my mail or personal when you were happiest dressed up. Please continue to send your stories and photos. I am having a very difficult time with your photos, trying to figure out which ones are real, and which were created with your graphic ability. You can send photos to me at anytime, I nothing but respect and admiration for your contributions. Have a wonderful New Year. With your help and others, this year is starting out with some honest, accepting feelings. Elizabethjane

    Dec 31, 2010
    1 like
  • petti100

    Let's see. You must have been about 12 or 13 if you were starting Jr. High, Bobbie. I remember that as a very impressionable age- right around puberty for many of us. Do you think that this experience either started, or reenforced , your desire to be in girls' clothes? I think it would have for me. At that age, it was diapers that dominated my desires, and dresses soon followed. Reading your story, which is very well written by the way, it must be more of a fond memory looking back on it. Did you ever find out if there were other boys that went through this "initiation" that developed a liking for feminine clothes? I've heard it said that these experiences of petticoating humiliation lead to the desire to crossdress later in life. I don't beleive it. I think that the curiosity, and even desire, is already there for those of us who finally pusue this pastime. It's just that our thoughts were very much our secrets at the time. While reading your story, and similar stories of others ( ie., Gigglettt's Nun story ), after the initial shock of the forced humiliation, it must been exciting for you. Like maybe you enjoyed a bit. Now be honest. I say this because I was forceably diapered at about ten years of age, and this is exactly how I felt at the time and afterward (maybe I should write about that). It's kind of like if we could relive those moments, we would actually enjoy the experience rather than being scared to death at the time. It's like, wow, they know about my secret desires somehow! But it's a great story and I hope you can tell about more exploits of your petticoating. Have a Happy New Year!

    Dec 30, 2010
    1 like
  • bobbie13

    Yes, if you read my stories you would see my mother kept me in dresses tilalmost my 17th birthday.

    Sep 10, 2010
    1 like
  • Ieatcreampie

    Your story is very cute and sad at the same time. Did you wear dresses or other girl clothes as you entered your teens?

    Sep 9, 2010
    3 likes
  • aloneinpantyhose

    oh u r so lucky to have been able to dress as a girl when you were younger.

    Sep 1, 2010
    2 likes
  • WetMarie

    cdsubalice, The key thing in this initiation was that it was meant to humiliate and degrade. It was to portray a "boy", they did not know his true inside gender identity, as something male society in its privileged place see as inferior, a girl. Yes for one who's true gender identity is opposite what society placed on them at birth it is a blessing in disguise but the demeaning intent is there.



    I say this from personal experience. I in elementary school never experienced such an initiation. No I actually wore whatever girls thing I could get away with. Early no one really cared. About the fourth grade that all changed. It was then that the teasing turned to verbal and physical abuse. I spent so many days sitting in a stall in the restroom crying. I cried not because of the names or the beatings I endured, no, I was crying because I hated being me. I hated that I was a girl but that awful body of mine wasn't. The Nuns further this humiliation when every first recess of the day held me back as the others filed out. They then pulled my waist band out by my belt and checked to see if I was wearing panties. If I was I was made to go to the principles office and it front of her changed. At first my mother was called to bring a pair of boy's briefs but it was happening so often that they kept a supply at school.



    Then in High School my freshman year our pastor suggested my parents place me in a seminary. There he felt I would see and be a "man"..right. My secret wasn't anything no one knew. The whole school knew the day I arrived...Heres the boy that thinks he a girl. When it came to the seniors play they give for the parents I was chosen to play a major part. This was something a freshman never had done in the history of the school. The play, The Avengers, and my part...Ema Peal. I being on stage most the whole time was tossed, pummeled and humiliated in every possible way. They finally dropped the curtain early because I was curled up in a ball on stage crying uncontrollably.



    Yes I finally a large room full of people including my own parents saw me openly as I always desired, a girl. I was so excited in the days building up to that night. I was so excited every time we dressed for rehearsal and that evening. everyone was so accepting and nice...I felt. Then that curtain was raised and every taunt, every mean and nasty thing and every punch I felt all came back. I was being humiliated and abused up on that stage and it was purposeful. It was meant to hurt. Nothing else.



    It was only about a month later that my parents were called. They were asked to withdraw me and place me in another school, I did not fit their idea of a student.

    Aug 9, 2010
    2 likes
  • cdsubalice

    Yours is not the first story I have heard of such initiations. My regret is that I did not go to your school. I think I would have reacted just as you did -- fearful of potential violence, emoboldened by seeing other freshman were similarly dressed.



    You did not describe how you felt once you realized that not only were others "suffering" the same as you, but that the teachers were understanding.



    I think or hope that I would have relaxed and enjoyed the experience, for it would have meant that I was publicly being made to do what I was already doing in secret.



    And again, if when I got home, and my mom saw me dressed and knew it was part on an school wide initiation, what would have been my future if she had said the same to me as your mom did to you?

    Aug 9, 2010
    1 like
  • WetMarie

    We share many things, many, of our childhood. Hugs

    Jul 18, 2010
    1 like