Dear Auntie Helga, I really enjoyed Prim's school sissy article in your February issue, although it also brought back some very shameful and painful memories. You see, while I doubt that there have ever really been any schools with an official school sissy, I'm sure almost everyone can remember being in a class where there was an effeminate boy who was the unofficial class sissy who got teased a lot for being a sissy. When I was in grade 5, I was that boy.
I was pretty smart when I was a kid, young for my grade even when I started school, and then I skipped a grade, so when I was in grade 5 I was easily the youngest in the class. I was also small for my age, kind of a skinny little kid, and not very good at sports. My parents divorced when I was a baby, so I was raised by a single mom who was perhaps a bit overprotective. Basically, I was quite the momma's boy, and shy and timid too, shading toward being quite effeminate. I even had pretty long hair for a boy, mainly because my mother really liked how I looked with long hair.
At school, I was used to being teased sometimes and called a sissy for preferring to play with girls (because boys played too roughly for me), but it had never been really bad until 5th grade. That year, right from the first day of school, there was this group of three girls and two boys in my class who started picking on me and teasing me and bullying me. From that first day they called me "sissy" instead of using my name. I was quite fearful of them, and after school each day I did my best to avoid them on my walk home. But on Friday of that first week, they cornered me on my way home, started teasing me and laughing at me for being a sissy, and then one of the girls said that because I was such a sissy, I should wear panties instead of underpants, and then another girl said that if I didn't want them to spank me in front of a lot of the kids in the class that I would have to come to school in panties on Monday.
I knew they were serious, and by the time I ran home I was crying, and told my mom what had happened. She gave me a hug, but was really angry about what those kids had done. She said that she was going to go to the school on Monday to talk to my teacher about it. I didn't want her to do that, because I figured it would just make the kids madder at me and it would be worse for me, so I begged my mom not to go. After a lot of begging, she relented, and said OK, and then we drove to a department store to buy a pair of panties for me to wear on Monday.
On Monday I wore the panties, which were pink with white lace around the waist and legs and a little red bow on the waistband in front. I was nervous as could be, and tried to stay away from the kids who were bullying me, but at recess they surrounded me and made me pull down my pants enough to show them I was wearing panties. They all laughed, and then said that they couldn't wait to see what color panties I would be wearing the next day. When I said that I thought I had to wear them only the one time, they said no, that I had to wear panties every day because I was a sissy every day. Again, I ran home in tears and told my mother what had happened. And again, she said she was going to talk to my teacher about this problem, but I talked her out of it, and the two of us then went to the department store for more panties so that I would have enough. This time, as we entered the girls clothing area, to my horror a saleslady came over to help us. My mom told her we were shopping for panties in my size. I wanted to leave right then and there and told my mom I was going back to the car, but my mother insisted I stay because she wanted to make sure that we got panties that I would like, now that I'd be wearing them every day. I could see the saleslady smiling quietly when she heard that, but she was then quite professional in helping us pick out ten or so pairs that would fit me.
After that, I wore panties to school every day, and every day I had to show the kids who were bullying me which panties I had on that day. It didn't take long, of course, for all of the other kids in the class to learn about my panty wearing, so basically all of them started calling me sissy. And then, a few weeks after that, the bullying group caught up with me after school one afternoon and one of the girls took out some nail polish and they polished my fingernails and toenails and then put lipstick on me and some other makeup too. When I got home in tears that day, my mom absolutely insisted on going to the school to talk with my teacher, even though I knew it wouldn't help things.
My mom talked with my teacher that afternoon, and when she came home she told me everything was going to be fine, that my teacher would make the other kids stop bullying me. Even so, the next day I still wore panties to school just in case When school started, my teacher called me up to the front of the class and while I stood there, she said to the class that she had been told that some of the kids were making me wear panties every day and calling me sissy and that she wanted those kids to fess up and to stop doing it. All the kids in the class were staring at me then, and I could see how angry the bully group kids were and I knew there was no way they would admit it had been them. One of those girls did speak up, but what she said was that if I said I'd been forced to wear panties that I was lying, and that I wore them because I was a sissy and that I liked wearing panties. My teacher turned to me and said that she could see that I was wearing panties, and asked if it was by choice or whether I was being forced to do it, and if forced, who was forcing me. Well my problem at that moment was that I knew that if I said I was forced, the bullying group would get me after school, probably spanking me in front of a lot of other kids, maybe hurting me worse than that, so I really had no choice: I said I was wearing panties because I wanted to. All the kids laughed and my teacher quite angrily told me to sit down, and said that because I'd lied to my mother about supposedly being forced to wear panties when really I liked it, and because I was blaming other kids who had done nothing to me, that my desk was being moved from the boy's side of the room to the girl's side of the room and she was going to call my mother to tell her the truth.
When I got home that afternoon I could tell that my mom was really angry with me. She said I'd lied to her about being forced to wear panties and that I should have just told her that I wanted to wear them. She also said that she had taken all of my boys underwear out of my dresser and put all the panties there, and that from then on I could wear panties all day every day, and night. She also warned me not to lie to her again like that and not to blame other kids unfairly like that. I tried one time to explain that actually I was being forced to wear the panties, but my mom angrily told me to stop lying.
After that, I became, for all intents and purposes, the class sissy, and almost every day brought some new humiliation. I know this letter is already getting pretty long, so I'll just mention a couple of the things that happened after that.
In October, one of the girls invited all of the kids in the class to a halloween party at her house. We were all supposed to wear a costume, and I thought I'd go as a doctor because that's what I wanted to be when I grew up (and that is what I eventually became). But the bully kids had a different idea. They stopped me after school and said that if I wanted to avoid some real pain I would come to the party as a princess and I would tell my mother that that's what I wanted to wear to the party. When I got home I showed my mother the invitation and told her that I wanted to go as a doctor but that the kids bullying me told me I had to go as a princess. My mom didn't believe me though. She got quite angry and told me that she'd warned me about lying and blaming others and that she knew I was a sissy and that she wasn't surprised at all that I would want to go to the party as a princess and that she would help me with my costume. There was no point in arguing with her, and I knew I had no choice about a costume, so I ended up a week later being dropped off at the party while wearing red shoes, white stockings, an ocean blue satin dress, faux pearls necklace, fingernails polished red, my longish hair brushed into a girlish style and sporting a tiara. When I got to the house and was ushered in by the parents, it was obvious they had no idea I was a boy, but then when one of the kids in the class saw me, a whole bunch of the kids in the class came over to laugh at how I looked, and the girl whose house it was said to her parents that I was the sissy she had told them about, and the mom laughed and said I was about as much of a sissy as any boy she had ever known.
Another particularly shameful time occurred in mid-December, just before school let out for the Christmas holidays. Two of the bullying girls stopped by my house on a Saturday afternoon and gave my mother a package for me. They said it was a gift and they were sure I would like it, and then left. I was nervous about opening it, but had no choice, so while my mom watched, I unwrapped it and opened the box. Inside was a note, and three sets of sleepwear. Girls sleepwear. A red flannel nightgown, a frilly pink nightie, and a pair of girls pajamas that were white with red hearts on them. The note said "Merry Christmas to our class sissy. You had said how much you wanted to start sleeping in a nightie, so we're sure you will enjoy spending your nights in all of these. We'll be expecting you to take pictures to show us how you look in each of them." I was shocked, and told my mom that I hadn't said that to them and that this was their way of teasing and bullying me, but my mom got angry and said that I was lying to her again and blaming others when it was obvious I'd told them I wanted to wear a nightie. She then sent me up to my room to put on the nightie and she took a picture. I then wore the nightgown the next night and the pajamas the night after that, and my mom took my picture each night and then had prints made and she mailed the prints to one of the girls who had dropped off the package. My mom also cleared out my boys pajamas and bought me some additional nighties and girls pajamas and that was all I wore at night for the rest of that year.
There are lots more stories of shameful experiences I could tell you about, but this letter is much too long already. I hope it hasn't bored you.
Dear Shelly, I'm sure it must have been quite humiliating being the school sissy but it also seems to have shaped your life to some extent, case in point that you wrote such a delightful letter to us and seem to be a regular reader. With that in mind it is my pleasure to share this with my other readers who will appreciate the trials and tribulations you went through back then.