A young boy is forced to wear a pink frilly dress!
My story occurred many years ago when I was eight years old. Like many boys at that particular age, I was not very fond of girls. Girls in their prissy, feminine ways just seemed so strange to us boys. I personally happened to be more bothered and critical of young girls than the average little boy. Every chance I got, I liked to tease, bother, and poke fun at all the neighborhood girls. Name-calling, pulling ponytails, and lifting up skirts was a regular routine for me. Needless to say, I was regularly in trouble with my parents for doing such antics. Many a young girl in my neighborhood would run home crying, telling tales of what that mean Dale did to them. As a result, my parents would receive many angry calls from many parents, teachers, and other guardians. In a vain attempt to straighten me out, I was regularly yelled at, punished, and spanked by my parents. It did little good, as I always resorted back to my girl-teasing ways.
One girl in particular who was a regular and prime recipient of my torture was Michelle Dietrich from across the street. The two of us had little to do with each other, other than having a healthy dislike for one another. The three-block walk to and from our elementary school was an excellent time for me to express my unfounded repulsion toward her. It was during our daily trip to and from the third grade that I would bug her in every way I could think up. As her mother and mine were friends, my mom would get especially mad at me when told of my shenanigans by Mrs. Dietrich after she heard about it from her upset daughter. But my teasing of Michelle became such a regular occurrence, that her mom, my mom, and even Michelle came to expect that kind of behavior from me.
One thing that particularly bothered me about Michelle was that she sometimes had to come to my house with me after school when her mother wasn’t yet home from work. That situation didn’t occur too frequently, but when it did, I was always mad because I had to have one of those yucky girls at my house. After the walk home school, the big event for Michelle & me was to see if Mrs. Dietrich’s car was in their driveway. If it was, it meant that she was home and that Michelle should go home. If the car was absent, that meant Michelle was to go across the street to my house to be watched by my mom until Mrs. Dietrich got home from work. In such situations, my mother always tried to have us play together as if we were as good of friends as she & Mrs. Dietrich were. Of course, I never cooperated, as I believed I had to live up to my reputation as a girl-hater.
On one particularly warm, sunny day in late October, Michelle & I arrived in front of our homes to see that Mrs. Dietrich had not yet made it home from work. I was especially mad since I had arranged with several of my friends to come over to my house that day after school at 4:00 PM. Even though that was still an hour away, the last thing I wanted was the possibility of Michelle hanging around my house while my friends were over. We had big plans that afternoon, determining what we were going to do for Halloween, which was right around the corner. We were going to decide what our costumes were going to be and plan the most lucrative route for trick-or-treating. I most certainly didn’t want a girl around for such important stuff.
As a kid, Halloween was my favorite holiday - next to Christmas. I mean, what could be better that dressing up in a scary costume and go around with all your friends and get as much candy as you could grab and haul in a three-hour time span?
I had to accept the fact that Michelle had to come over to my house that afternoon, and just hope she would be gone by the time my friends arrived. We walked in the house and my mom greeted us with a hearty "Hello!" She asked how school was. I responded by saying "School was lousy because there was a bunch of smelly girls there, and now being home stinks because one of them followed me home!" My mother was offended by my statement, but not surprised, I’m sure. She scolded me for my rude behavior and told me not to act that way when we had company. My mom then suggested that Michelle & me go outside and play while she got together some milk & cookies for us. Playing with Michelle, especially outside where everyone could see us, was the last thing I wanted to do. Being a typical smart-alec, I said "fine!" and ran out the front door and started climbing the tree in our front yard. Since Michelle was wearing a pretty dress, I knew she probably wouldn’t want to skin up her knees by following me up there. Michelle just stood on the front porch, not knowing what to do as she watched me climb higher in the tree. My mom came to the front door and yelled out the screen to me, "Oh, Dale, you are such a pain in the butt!" Why don’t you just be nice for once and come down here to play with Michelle?" I said, "Why doesn’t she come up here with me?" knowing that that wasn’t going to happen. My mom called me a snot and turned to go back in the house. She had Michelle come with her since I wasn’t being very hospitable. They came back a few minutes later, with milk and cookies set out on a tray. My mom thought she was going to lure me down with the goodies. She asked "How about you come down and have some cookies with us?" Although I was tempted, I stuck to my guns. I said "I will have all the sweets I want next week from trick-or-treating, so I don’t need the cookies now!" My mom grumbled something negative in response, and then proceeded to have a pleasant conversation with Michelle as they enjoyed some cookies without me.
Shortly thereafter, we heard a car horn. Mrs. Dietrich has just pulled her car into her driveway across the street. I heard my mom say, "Mrs. Dietrich is home! Time to take you home, Michelle." She then yelled up to me, "Dale, get down here - we have to take Michelle back home!" I responded, "Can’t I just stay here? I am waiting for my friends to come over at 4:00." My mom shot back, "That’s over a half-hour from now! I am not leaving you home alone for that long, especially up in that tree! Get down now! It will only take a minute to take Michelle across the street!" Reluctantly, I climbed down. As soon as I did, my mom grabbed a hold of my hand and yanked me along as we crossed the street to Michelle’s house. At the same time, she held Michelle’s hand with her other hand and somehow managed to guide her along gently.
When we got there, Mrs. Dietrich got out of her car and started apologizing to my mother. "I am so sorry!" she said. "We had absolutely no food in the house so I had to stop off at the supermarket on the way home to get something for dinner tonight!" My mom said, "No problem!" I always enjoy the opportunity to spend some time with your lovely daughter. You are so lucky. I wish I has a sweet little girl of my own." as she shot a snotty look at me. Mrs. Dietrich took a look at me and said "Well hello, Dale. Did you torture my little girl this afternoon like you always do?" Before I could say anything rude, my mom said, "Of course he did. What a bratty little boy!" Changing the subject, my mom asked Mrs. Dietrich if she needed help bringing in groceries. Mrs. Dietrich said that wasn’t necessary, but my mom insisted on helping. She grabbed a couple of bags and recruited me too, handing me a bag to carry into their house. I reluctantly took it and followed the three ladies into the Dietrich household, hoping that this wouldn’t take very long.
When we got inside, the two adults started putting away groceries and began gabbing. When Mrs. Dietrich offered my mom some tea, I knew it wasn’t going to be a short mission. Michelle & I just stood there, not knowing what to do. After a few moments, Mrs. Dietrich noticed us and said "Why don’t you two go outside & play?" (the standard busy mom request). I groaned at the suggestion. My mom said to her "Forget it. I already tried that one and he wouldn’t go for it." So Mrs. Dietrich told Michelle she could go out to play by herself. After she left, I began to whine to my mom saying "Mom, I want to get home now! I got stuff to do." She responded sternly, "I will be here only a few minutes with Mrs. Dietrich. If you are too much of a snot to go outside & play with Michelle, then you will just have to just sit down and wait for me!" I knew my mom’s idea of a few minutes was really an eternity. I plopped down on the Dietrich’s couch, facing the two women, and began to pout. They managed to ignore me for a while, but I became more and more obvious about my impatience.
So, Mrs. Dietrich decided to pay some attention to me. "What is your big hurry to get home, Dale? Don’t you like hanging out with us ladies?" she said, trying to stir up something with me. I said "I have to get home to go over my Halloween plans with my friends. Plus, I don’t like being at a girl’s house." My mom explained to her that my friends were coming over in 30 minutes. Mrs. Dietrich asked me what I was going to be for Halloween. I responded dejectedly, "I don’t know yet. I still have to figure that out." Mrs. Dietrich thought for a moment and said, "I have an idea for you - it would be a really creepy costume!" I asked half interested "What’s your idea?" She said, "Oh I don’t know if you could handle it. This costume idea would be really yucky and gross, going by your standards." Hearing her description, I became highly interested in her idea. Desperate for suggestions, I begged, "Tell me! Tell me!" She finally said, "How about you go dressed up as a girl? According to you, there couldn’t be anything scarier!" Hearing her lame idea, I became dejected again. I muttered, "Girls sure are gross, but there is now way I would ever dress up like one." My mother said, "Oh, why not Dale? I think it is a good suggestion. You would look so cute in a little dress!" Once again, I proclaimed my dislike of the idea. But the women could see they hit a sore spot with me. It became fun for them to tease me with their insane costume idea. So, they kept it up. Mrs. Dietrich said, "You could borrow one of Michelle’s dresses. You look to be about her size, and I’m sure she wouldn’t mind." Getting more and more irritated, I kept rejecting their comments. My Mom said, "Oh she would look so darling. We could get a wig and a nice little purse for her!" Mrs. Dietrich added, "I think she should carry a little baby doll too!" Being called a "she" really ticked me off. After putting up with numerous similar comments, I finally had enough. I flipped out and yelled at them "I AM NOT GOING TO DRESS UP LIKE A GOOFY GIRL! IT IS A DUMB IDEA AND YOU ARE STUPID FOR EVEN SUGGESTING IT!"
Hearing my outburst, my mom got one of her trademark angry looks on her face. Seeing that, I knew I was in for it. She hissed at me, "How dare you talk to Mrs. Dietrich like that in her own home! I am so embarrassed!" With that she got up from her chair and stomped across the room to me, bent down, grabbed me by my shoulders, and gave me a vigorous shaking as she continued to scold me. She said, "I have had just about enough from you today! You haven’t even been home from school for an hour, yet and you have managed to make my blood boil with your intolerable behavior towards Mr. Dietrich and Michelle!" With that, she commanded me to apologize to Mrs. Dietrich as she shoved me over in front of her. I could see that Mrs. Dietrich had an embarrassed look on her face too. I said to my mom, "Well she started it!" My mom said, "Nonsense! Now you say you’re sorry!" Mrs. Dietrich spoke up, "He’s right, Mary - I did provoke the boy. You can’t blame him for not wanting to dress up as a girl for Halloween." My mom responded, "But its how he went about expressing it to you. He needs to learn his manners!" With that, I had to start my apology. I muttered, "I’m sorry Mrs. Dietrich." "Sorry for what!" my mom said. "Sorry for calling you stupid", I said. My mom said, "And what else?" I said "Sorry for calling your costume idea dumb". "And what else?" my mom said again. It was one of those kind of apologies - the kind where you are forced to think up things to be sorry about, just to get through the ordeal. When I was finished, Mrs. Dietrich responded, "I am sorry too Dale. I was wrong to tease you. But now maybe you can see that it’s not nice to tease someone because they are of the opposite gender." I rolled my eyes and said, "Whatever!" With that statement, my mom could tell that I really didn’t feel bad for my actions, so she said, "Now you are really going to get it, young man! Your father is going to give you a spanking tonight when he gets home, after he hears how you behaved today!" I winced at the thought, because spanking was the ultimate form of discipline in our home, and when my dad gave them to me, he really gave them to me!
Mrs. Dietrich got a worried look on her face. She said, "Oh Mary, I would hate to see Dale get spanked over this! It’s really not his fault! I am to blame for all this. Please don’t spank him." By her statement, it was obvious that Mrs. Dietrich did not believe in corporal punishment. And why should she? She only had one sweet little girl who never gave her a lick of trouble. My mom said to her, "You aren’t the mother of a bratty little boy. I think you would see it differently if you had to out up with all the trouble Dale causes!" She went on, "He most certainly is going to get a spanking - and a good one too!" Mrs. Dietrich continued her plea, "Isn’t there some other way to teach him his lesson?" Obviously frustrated, my mom responded, "Oh, he never learns his lesson. We scold him, punish him, and spank him regularly, but he never shapes up!" "So why spank him again?" Mrs. Dietrich asked. "If you keep using the same forms of discipline, and he never learns his lesson, why keep doing them?" she said.
I began to think that I was going to get out of a spanking. So, I couldn’t help but to get a little smile on my face. I kept hoping that Mrs. Dietrich’s words might just get me out of trouble. Little did I know that they were about to put me deeper into trouble. My mom might have been persuaded to let me off the hook, but when she looked at me, she could tell what I was thinking. She said, "Oh, we have to do something to him for his bratty behavior today!" Mrs. Dietrich got a thoughtful look on her face and then said, "Maybe Dale would respond to a different form of persuasion." My mom asked "What do you mean?" Mrs. Dietrich replied, "Well, in his apology to me, Dale said that my idea wasn’t stupid after all. That being the case, why don’t we go through with it and put a little dress on him so he can see how it feels to be a girl?" My mom was surprised for a moment by her unconventional idea. She asked, "Do you think that will work?" Mrs. Dietrich responded, "I am sure it will! - No boy would ever want to wear a dress, so I think it would be an ideal form of punishment." My mom said, "I don’t know…" Mrs. Dietrich continued, "And, I think the punishment should fit the crime. If Dale were forced to dress like a girl, then I think he might gain a better appreciation of us girls and quit being so mean to us."
Of course, I didn’t like that idea at all. Hearing the direction the conversation took was beginning to concern me. In a worried tone of voice, I told my mom, "I’ll be good, I promise! You don’t have to punish me that way!" My mom shot back, "You can stay out of this! Any ideas you have will be the last thing we are going to do!"
My mom had to think about this for a moment. She looked at me and saw a fear in my face that she had never seen before when faced with any other form of punishment. Then, she looked at Mrs. Dietrich who had a big grin on her face and a twinkle in her eye. After weighing the facts she finally said, "Let’s do it! I truly believe Dale will learn a lesson from this experience, plus it will be fun too!" I stammered "What! I can’t believe you are taking this seriously!" How can you do this?" My mom responded, "Watch me!" Then she said to Mrs. Dietrich, "What kind of dress should Dale wear?" Mrs. Dietrich squealed, "Oh, Goody! I have the perfect dress in mind or him! I’ll go get it!"
With that, she skipped down the hall to Michelle’s room. I looked back at my mom and said, "This is dumb! I said I was sorry. Isn’t that enough?" My mom said, "No it is not, because you never really are sorry, now are you?" I think we need to do something that will really make you truly feel sorry, and Mrs. Dietrich’s idea is the best idea I’ve heard in a long time."
As I tried to get over my astonishment at this crazy idea, I had to come to grips with the sight of my selected attire. Mrs. Dietrich had returned with the girliest, most feminine dress I had ever seen! It was a little pink dress that was just dripping in ribbons and lace. It had short puffy sleeves with white lace trim and a very short, but very full skirt radiating out from the waist. Underneath, the skirt was all poofed out with layers of sewn-in stiff white petticoats. It was by far the sissiest, most frou-frou choice Mrs. Dietrich could pull from Michelle’s closet. To complete the outfit, Mrs. Dietrich had also brought out a pair of girl’s white socks trimmed with lace, as well as a pair of little girl’s black patent leather shoes. My eyes nearly fell out of my head when I saw what she had. My mom said, "Oh, that is just perfect! I can’t wait to see it on him!" Mrs. Dietrich responded "Isn’t it beautiful?" And with that, she held it up against me and said, "It looks to be his size too!" Faced with this most ridiculous situation, I got my composure and said "No way! I am not wearing that dress! It is too sissy! In fact, I am not going to wear any dress at all!" My mom said "Don’t you start again or you are just going to make it worse!" There was no way I could conceive the situation getting any worse. I got very belligerent toward her and said, "Oh, yeah, I’d like to see you make me! I am not going to put it on myself, and if you & Mrs. Dietrich try to put it on me, I put up a struggle like you’ve never seen! There is no way you are going to make me wear that dress!"
I said this knowing I was going to get in even more trouble, but I knew I was right. If I didn’t let them, there was no way they were going to get that dress on me. And then the only course of action my mom could take was to have my dad spank me. I didn’t like the thought of that, but it was a million times better than having to wear a dress!
My mom replied very calmly and clearly, "Oh, you are going to put on that dress young man. Your punishment will be either that or no trick-or-treating this year! It is your choice." I was stunned by her words. No trick-or-treat! How could she even think it? That was the only other thing she could ever think up that could be worse than having to wear a girl’s dress. She had me right where she wanted me! I was faced with the worse decision I ever had to make in all of my eight years. What should I do? I thought maybe not going trick-or-treating might be tolerable, but after giving it some thought, I didn’t see how I could live with that. Then I thought about wearing that sissy dress. As stupid as it was, I thought all I had to do was put it on for a few minutes so my mom & Mrs. Dietrich could poke fun at me, and then it would be all over. No one else would have to know about me wearing Michelle’s dress and I could still get my big haul of candy.
After a few moments of tense self-deliberation, I could barley utter the words, "Give me the dress." Mrs. Dietrich squealed, "Oh goody! Here you go. And don’t forget the little girl socks & shoes too!" She continued in a sarcastic tone, "I was going to grab a pair of Michelle’s frilly undies too, but we wouldn’t want to embarrass you, now would we?" In complete astonishment, I took the dress from her. She then said, "You can change in the bathroom. It’s down the hall, first door on the left." I looked at my mom one last time to see if I was going to get a last-moment reprieve. She just stood there sternly with an unyielding smirk on her face and said, "Snap to it! You’ve got ten minutes to get that dress on, and I’ll be waiting here to see you in it!" With that, any remaining hope to avoid this humiliating situation was gone. I started slowly down the hall toward the bathroom. When I got there, I went in, turned on the light and closed the door.
I stood there, holding that frou-frou dress out in front of me wondering how I ever got into this mess. I actually had to wear this thing - and parade around in it in front of my mom and goofy neighbor! I nearly choked at the thought of it. But, it was my only way to go trick-or-treating, so I had to do it. Just then, I heard my mom yell, "Eight minutes!" That snapped me out of it. I took off my shoes, socks, pants, and shirt, then took the dress off the hangar. I wasn’t even entirely sure how to get into it, so I just poked my head into the middle of all those short little petticoats under the skirt and kept going until my head came out the other end. I guided my arms through the same way until I found the interior of the puffy sleeves, and then through the armholes. I pulled the whole thing down until it seemed to be in place, and then I took a look in the full-length mirror on the bathroom door. There was my image of me in a pink frilly dress! It was definitely an embarrassing experience, but I had not yet achieved my most embarrassing moment.
I couldn’t believe it! I was wearing a dress! I began to study how it looked on me and began to notice a kind of feel on my body that I had never encountered with any other kind of clothing. I actually began to admire how I looked in a dress. I turned from side to side to feel it brush against my legs. It became a totally exhilarating experience for me. I think I actually almost passed out! I couldn’t believe how poofy the skirt was! This thing was sticking out from my body by a foot in all directions. I also could not believe how short the skirt was either! It barley covered my underwear! I tried to give it a tug downward, but the poofy petticoats underneath kept fluffing it up and out. I was so caught up in the thrill of this new experience that I didn’t really notice the slight commotion that was going on out in the living room.
Then I heard my mom yell, "Five minutes!" With that, I grabbed the socks and shoes and sat down on the edge of their bathtub to put them on. When I sat down, I immediately noticed the abrupt feel of the cold porcelain against my upper thighs and butt. My underwear was touching the surface on which I was sitting! It was like I didn’t have any pants on! Then I thought, I don’t have any pants on - it’s a dress! I could not believe girls had to have their underwear make unobstructed contact with the outside world. Now I understood why girls wore pretty underwear rather than the plain, boring ones us guys had to wear - with a short dress, there was always that chance that their underwear could be seen! And if it could be seen, wouldn’t they want them to look as pretty as their dresses? It was such a foreign feeling to me - but actually an exciting once to my surprise. As I put on the footwear, I began to wonder what was wrong with me - Why was I actually enjoying this "punishment"? As I tried to come to terms with this rush of thrilling emotions, I came to the conclusion, not only was this discipline better than spanking, but that it was more fun than anything I had experienced in my life! But then, I was ashamed of myself for thinking this way. I realized, as weird as it was, even though I liked it, I could never let on to anyone how much I enjoyed wearing a dress. At that moment, it re-occurred to me that I was going to have to model this outfit to my mom & Mrs. Dietrich. I began to tense up again at the thought of confronting them in this way. I could hear my mom counting down loudly from 10. That was my cue. My time was up. It was time to present myself to others in this pink, frilly dress.
I opened the door and poked my head out into the hallway. I looked down at the other end and could see my mom sitting on a chair in the living room. She said, "Step out in the hall where I can see you dear." I did as she said, feeling my stiff, petticoated skirt brush against the doorframe on my way out of the bathroom. I just stood there as she looked at me in Michelle’s dress and started to snicker and tried to keep a straight face. I could hear Mrs. Dietrich say, from out of my view, "Is she coming?" My mom replied, "Here she comes now." as she motioned for me to come towards her. I walked down the hall with a strange mix of emotions. I felt silly knowing I was going to be seen by the women in this ridiculous get-up, but at the same time, it was a thrill to feel the sway of my poofy little skirt as I walked. When I got out to the living room, all it could do was watch my mom & Mrs. Dietrich gaze at me in wonderment as they started commenting on my attire. "Oh, doesn’t she look pretty!" said Mrs. Dietrich from the couch. My mom replied, "Oh, she looks just darling! She should wear dresses more often!" My mom commanded me to turn around to give them the whole show. I did as she said, but it was not to her satisfaction. She said "Quicker!" This time, I gave more of a spin than a turn, and listened to the ladies burst out in laughter. I knew they were getting more than a glimpse of my underwear. I tried in vain to pull the dress down a little further on me. Mrs. Dietrich asked me, "Doesn’t it feel great to wear a dress?" Lying to her, I replied "No." Mrs. Dietrich said, "You have to be joking! I think this little girl is telling us a fib, Mary!" My mom said, "I bet she just loves her new outfit! We are going to have to run out to the mall to get her some of her own dresses!" As embarrassing as their teasing me was, I still had not yet reached my most embarrassing moment.
As much as I secretly liked wearing the dress, I felt I had just about enough of the teasing from the ladies. I told my mom, "O.K. I did what you said. You got to see me in this goofy dress and now I am going to change back into my own clothes!" As I started to turn away, my mom said, "Not so fast. How about you come sit down with us and enjoy our little tea party?" I knew there was no choice in the matter, so I grudgingly did as I was told. I walked across the living room to the empty chair in front of the large bay window. I must have looked visibly uncomfortable as I sat down, trying to mind my skirt as I did. Mrs. Dietrich said, "Is something wrong, Dale?" I said, "Would you mind closing the curtains on this window please?" Mrs. Dietrich responded, "Why should I do that, Dale? Don’t you want to show off your pretty new dress?" I replied sarcastically, "I’d rather not, thank you!" Mrs. Dietrich replied, "Nonsense! A pretty little girl like you should love showing off her frilly little dress - AND HERE’S YOUR CHANCE!
As she said those last few words in a vengeful tone, I only had to wonder for a moment what was going on. Then she yelled out, "O.K. GIRLS - NOW!" At that moment, the front door swung open and standing on the stoop was Michelle and four of her friends! It was at that moment that I realized what the slight commotion was that I was hearing from the bathroom as I put on the dress. The moms had been organizing this ambush! All the girls came rushing into the living room squealing with delight. They all stood there pointing and laughing at the sight of that rotten Dale having to wear girly clothing! I was humiliated! Five girls from my class were seeing me in a pink frilly little dress! I would never live this down! But, as embarrassing as it was, it was still not my most embarrassing moment.
I immediately jumped up and tried to run out of the room. I rounded the corner to head back towards the bathroom. Mrs. Dietrich anticipated this move and jumped up too, squeezing through a small gap at the other end of the couch. As she was blocking my access to the hallway, I tried to stop. Since I was not used to wearing little black patent leather girl’s shoes, I didn’t realize what little traction they had. My feet slipped out from under me and I fell flat on my back on the floor right if front of Mrs. Dietrich. With my feet up in the air, all I could see in front of me was a bunch of pink & white as my petticoated skirt flew up in my face. I immediately felt a draft around my lower extremities. My underwear was on full display to the delight of the roomful of females! I pushed my petticoats back down as I struggled to get up. Mrs. Dietrich reached up on a high shelf and pulled down a strategically-hidden camera. She said, "This looks like a Kodak Moment to me!" and started snapping lots of pictures. Right about then, it felt more like a Maalox moment to me!
I ran the only other direction I could go where there was no one to see me like this - towards the kitchen. When I got there, the group of girls and moms simply followed me in so they could get some more laughs as they stared at the snotty neighborhood boy in a dress. Since there was no other place I could go in the house, I went the only place I could - out the back door! I pushed the screen door shut behind me and held it shut in a desperate but lame effort to keep them from following me. As the girls ran through the house to the front door, Mrs. Dietrich said, "Oh, I didn’t realize you wanted to go outside to show off your new pink little dress to the whole neighborhood. We’ll leave you alone." And with that she flicked the lock on the door handle and sat back, laughed, and watched me out the window as Michelle & her friends ran around the side of the house to see me again in the back yard.
All the girls gathered around me and started calling me names and making fun of me - just like I had done to each them many times in the past! One of girls behind me reached out and lifted up the skirt of my dress! I was humiliated. They were seeing my underwear again - and much more than the occasional glimpse the short, poofy dress already allowed them to see! As I turned away from the first offender, another one was there to yank up my dress. I felt so violated - and vulnerable! At that point, I felt as embarrassed as I ever had felt in my life - but my most embarrassing moment had still not yet occurred.
Such antics must have went on in the Dietrich’s back yard for several minutes, but it felt like an eternity in hell to me. Finally, my mom came to the back door, opened it, and spoke to me through the screen door. "So, now do you know how it feels to be a girl?" "Sort of", I replied". Then she said, "And now do you understand how it feels to be teased just because you are a girl? "I guess so", I replied. "Are you ready to go home now?" she asked me. I quickly responded, "As soon as I get my own clothes on, I am!" My mom said, "Oh, that won’t be necessary just yet." She continued, "I have your clothes right here." as she held up a brown paper bag to show me. "I believe Mrs. Dietrich came up with a marvelous way to discipline you and I think you could use a little more time in that dress to thoroughly learn your lesson. Mrs. Dietrich was kind enough to let us borrow Michelle’s dress for a little while. So, not only are you going to wear it to go home, but I believe we have determined what your costume for Halloween is going to be." Then she said, "I will still allow you to go trick-or-treating this year, but only if you dress up as a little girl!" With that, all the girls and Mrs. Dietrich laughed at the thought of my unplanned Halloween costume. As much as I initially liked putting on the dress by myself in the Dietrich’s bathroom, the last thing I wanted was the humiliation of having to wear it as my costume for everyone to laugh at! Before I could gather my thoughts to express any protest, my mom opened the screen door, stepped out, and took my hand. "Let’s go home now, dear." she said. We started walking up the Dietrich’s driveway towards the front of the house. All the girls laughed and skipped along with us as they continued to marvel at the sight of that nasty Dale in Michelle’s pink frilly dress.
If I wasn’t self-conscious before, I really was now, because we lived on kind of a busy road. Just when I thought it couldn’t get any worse, we reached the front yards and saw the Dietrich’s next-door neighbor, Tony out raking leaves. When he got a load of me, he stopped what he was doing and whistled at me. He called out, "Nice Halloween costume!" as we started across the street. Just then, we encountered Jennifer Walmsley riding by on her ten-speed bike. Jennifer was a local teenage girl who used to baby-sit me until she couldn’t take the abuse anymore. She had quit doing that job about a year ago due to my shenanigans. As she rode by, she slowed down and busted out laughing at the sight of me. When we got to the other side of the road, we saw our next-door neighbors out on their side porch, enjoying the unseasonably warm October afternoon. The Doberninks were an old retired couple who usually weren’t very interested in me, due to the trouble they claimed I regularly caused. But now, under these unusual circumstances, they wanted me to come speak to them. My mom guided me over to them and said, "Doesn’t she look pretty in her new dress?" She made me explain to them that I was wearing girl’s clothes as punishment for all the teasing I had done to all the neighborhood girls. My mom added that it was going to be my Halloween costume that I was going to wear for trick-or-treating, as well as to the costume party next Friday at school. That last part was most certainly unwelcome news to me. My mom also told them that we were going to hold onto the dress for a while after Halloween, and if my mom got any new reports of bad behavior from me, she was going to make me wear it again. The Doberninks proceeded to ask me a bunch of dumb questions like "Did I have on girl’s underwear too?" My mom told me to show them, so I reluctantly had to hold up my skirt to reveal my own underwear. They continued with questions such as, "Did I like wearing a dress?, Was this the first time I had worn a dress?, Did I own any more dresses?", etc. While I found this all very embarrassing, I still had not yet achieved my most embarrassing moment
As I answered their stupid questions, I had no idea that my mom, standing behind me, had gestured to the Doberninks that they should remain quiet as she sneaked away towards our house. After standing there for a few minutes in my neighbor’s yard, preoccupied with the inquiry, my mother finally called out to me from our front porch. Surprised to hear her voice calling out from that distance, I turned to face her. She said, "Well Dale, you wanted to get home to meet with your friends to discuss your Halloween plans! So why don’t you show them your costume? Here they come now!"
Hearing those last few words, I broke into a cold sweat as I turned to look at the front street. At that moment, all four of my best friends rode up the driveway on their bikes and pulled up along side of me, gawking at me wearing a pink frilly dress!
And that was my most embarrassing moment!
In closing, I have to say, there is no words you can ever say to talk your way out of the fact you are wearing a pink frilly dress. I tried to explain to my friends the strange circumstances, but there was no accepting me in my sissified state. After their initial astonishment, they proceeded to have a hearty laugh at my tremendous expense, made numerous snide comments at my predicament, and then turned to ride away, leaving me alone in my humiliated state.
As tragic as this seemed to me at the time, the experience was beneficial to me in a couple of ways. One, I never made fun of any of the neighborhood girls ever again. The harsh lesson taught me to me a respectful, well-mannered little boy. Two, while I found being publicly displayed this way to be embarrassing, the situation introduced me to the wonderful joys of wearing pretty petticoated dresses!
My mother lived up to her word and "made" me wear Michelle’s pretty little pink dress as my Halloween costume. She rounded out my attire by putting one of her old blonde wigs on my head and putting in pigtails. She applied a little makeup to my face to achieve a greater feminine effect, and finally, she borrowed that pair of Michelle’s white lacy undies that Mrs. Dietrich originally suggested to wear out over top of my own underwear. Either way, showing off my own underwear or the girly ones to the world from under my short poofy petticoats was equally embarrassing. But the girl’s underwear gave me even more of a thrill! I "had" to wear this outfit to my school Halloween party that next Friday. The whole school got a laugh seeing Dale dressed up as a little girl in the most feminine dress they had ever seen. Taking part in all the games and contests that day at the party was a real adventure too! If you have ever tried running a relay race, bending over to bob for apples, or climbing to the top of a high school yard slide and slide down it while wearing a short little dress, you know what I mean!
And I had to go trick-or-treating around my neighborhood that evening dressed up as a little girl too. Of course, my friends had nothing to do with me that night. They went trick-or-treating for candy without me, as they wanted no part of that Dale in his girly dress. But I was not left alone that evening. Realizing my predicament, my mother arranged with Mrs. Dietrich to have me go trick-or-treating with Michelle and her friends. They were all dressed as ballerinas, princesses, and fairies, so I fit right in with them, wearing my pink frilly dress. As I went door to door to get my treats, I got many comments from people. Most did not even realize I was a boy dressed as a girl. They would say I was a pretty girl in my beautiful pink dress, but wondered why I wasn’t wearing a costume. Of course, I had to explain to them that they were talking to a boy. Then I would see the looks of astonishment, humor, and then finally understanding that this truly was a costume.
Having to wear this outfit for all to see for an entire day made me get over the embarrassment of having to wear a pink frilly dress publicly. While I could have done without some of the teasing I endured, the experience made me realize that I really enjoyed wearing this pretty, poofy dress. As my mom planned, the dress did stay in our home for a couple of weeks after Halloween, in case my mom saw the need to punish me and make me wear it again. But, it was not necessary, as I had been totally reformed of my girl-teasing ways from the initial experience. And besides, wearing a dress had not really become a punishment to me anymore. While we still had Michelle’s dress, I would go into my room, close the door, and take her dress from my closet and put it on to wear while I played. I tried to keep this a private affair, but several times, my mom would walk in on me in this state. Rather than being mad, she would just smile sweetly and let me be.
But eventually, my mom had to return the dress to the Dietrich's. Although I didn’t express it outwardly, that was a sad day for me. My mom knew this, and felt bad. She hated ruining my new fun secret. So, she did the next best thing. To my surprise (and great pleasure), she came home one day from the mall with several packages, claiming she had presents for me. I was curious as it wasn’t my birthday or Christmas yet. When I opened them, I could hardly contain my joy as I saw that she had bought me my own pink frilly dress! This included socks, shoes, and panties too, just like Michelle’s outfit! So, now I had my own dress to play in. Since it took a couple of months for my friends to get over the shock of seeing me dressed as a girl for Halloween, they hadn’t been coming around to see me. So, for lack of having anyone else to play with, I would play with Michelle and her friends. This really wasn’t a problem for me any more since I had learned my lesson so effectively. I actually enjoyed playing with little girls and doing all the little girl activities. Michelle and I would go over to each other’s houses and play dress up, putting on pretty frilly dresses and thoroughly enjoying ourselves. Another great thing about this experience was that Michelle and I became best friends - and eventually life-long companions. After a while, my own friends started coming around again, and I resumed doing regular boy-type activities. But, I would split my time between the girl and boy realms, one day climbing trees, the next, having beautiful tea parties dressed to the nines in my pretty pink frilly dress.
This went on for a few years. Eventually, I outgrew my dress and there was no new one to replace it. My mother never seemed to worry about me having a "girly" side to me, but she didn’t continue to support this behavior when I got older. It was never really a problem in her mind, but rather just a stage that she thought I would eventually get over. That was one thing she was wrong about - I never really got over my love of wearing pretty frilly dresses. When she introduced me to the wonderful world of frou-frou feminine attire that day so many years ago when she punished me as a child, she had no idea how that event would effect me for the rest of my life. As an older child, I would secretly poke around in her closet and try on her clothes when no one else was home. This continued into my teens when I began experiencing the joys of adult woman’s dresses, petticoats, brassieres, stockings, garter belts, high-heeled pumps, etc.
As Michelle and I continued our friendship through the years, our relationship turned into dating. All the while, she was always aware of my love for wearing pretty women’s clothes and never once had a problem with it. Of course, most women would probably have a problem with the guy they were dating if they knew he dressed in women’s clothing. But since she had been involved in this matter from the beginning during our childhoods and was present during most of its evolution, she never recognized the situation as a problem.
We went to our senior prom together and had a wonderful time. She wore the most beautiful feminine dress I had seen, since the day I donned her pretty pink childhood dress. I think she intentionally selected a pink prom dress to wear that evening with beautiful white petticoats filling it out underneath. She did this as a reminder of that special moment years ago and the many fun dress-up times we had together thereafter. That evening, after the dance, we had a wonderful time at a local motel, dressing me up entirely in her outfit including Michelle’s lingerie, petticoats, heels, etc. We proceeded to make the evening extra special by venturing into the first sexual encounter for both of us.
I am very happy to say we committed the rest of our lives together by eventually getting married. I knew there was no other woman for me. I loved her dearly and knew no other woman would understand, support, and encourage my "hobby" the way Michelle did. Presently, in our adult lives, I continue to dress up in women’s clothes. With my wife’s help, I wear the most beautiful feminine outfits. I especially love full petticoated skirts. But, as many of us know, this style has gone the way of sock-hops and drive-in movies. Petticoats are difficult to find now in this modern era. But, because of this modern era, I was able to discover the Pettipond website. Thank god for the Internet! Now I can appreciate the lost art of wearing petticoats by viewing other’s pleasures in this fetish and ordering my own to wear. I am able continue my lifelong tradition of wearing full petticoated dresses and skirts that started so long ago in my childhood. What had started out as my most embarrassing moment has become a life long thrill!
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