The 2nd Halloween For A Boy Dressed As A Girl--Part 1 -- A Blissful Young Crossdresser free porn video

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5th Grade. 11 years old. Dressed as a girl again on Halloween. As a cheerleader. My next old sister's cheer uniform. Her idea. Her bra and panty too. My special "Boob" socks to give the appearance of breast. A discussion I had with my next 2 older sisters. How ample were my false breast to be? Normal size for girls my age? Bigger for my ego as a girl, for all the times I have dressed up with them through the years? Dolly Parton size? Because my 2nd oldest sis Joan, made the suggestion that I cut a Nerf football in half. Trust me, I thought real quick of what she said but I did not want to cut that Nerf in half. Besides, those Nerf boobs would give me some very pointy breast. That thought made me laugh. Even at 11 years old, I knew what a bullet bra was. Television helped out with that ;-) Never seen one in person or in the Sears, Pennys and Montgomery Wards catalogs that I looked through. I loved to see all the foundation garments in those catalogs. Imagining myself in so many of those delectable creations. My mother had only so many choices available to me. I settled on 4 socks rolled up for each bra cup. Ample size for my reflection in the mirror. 5th grade for me meant El was now in junior high. Halloween was not celebrated at that school. I would ride the bus to school with my little twin sisters who were 2 grades back. As a girl cheerleader. The 1st time I went to school as a girl on Halloween, was 3 years earlier. That was before we moved and that school was within walking distance. I was a boy that liked to dress up in girl's clothes. My mother's too, of course. The dress up games I played with my 5 sisters kind of went away as the 3 older girls interest had changed as they grew older. But my interest only increased. Girls in school were growing. Puberty was hitting them. But not me. Halloween finally showed up. I was ready to spend the day as a girl. No clock to watch as to how much time I thought I had left being dressed up in female clothes. No worries about getting those clothes and heels back to their proper places. No thoughts about being caught at all. Being everywhere I wanted to be dressed as a girl and not caring who knew. I started the day by taking off the bra I was wearing all night in bed. I put on El's pink panty the night before. I certainly liked sleeping in a bra and panty. Sometimes I wished I had my own nightie to sleep in. I did not want to chance one of their nighties come up missing and have them go looking for where it might obviously be. In my boy PJs for breakfast, today's Halloween costumes were the subject of discussion. Cutting my Nerf football in half to use as boobs came up. Our mother said that I was not to cut that up. "I wasn't going to. That was Joanie's idea to do that. Besides, I don't want pointed boobs". My sisters laughed and our mother just rolled her eyes. Off to my room to get started to spend the day as a girl cheerleader. My oldest sis Mary, gave me a pair of her pantyhose. Pulling up pantyhose always made me start to feel like a girl. Next was the cheer skirt. A purple skirt with white pleats. I checked out my skirted behind in my big mirror for some reason. A little wiggle to make me laugh. Unfortunately being a cheerleader meant not being able to slide my nylon encased feet into some high heels. Such a treasured delight that was to me. I wore my own white gym shoes. I could fit into El's but I did not want to scuff them up. Possibly hurting my chances in the future of wearing more of her clothes ;-) Her bra was a panty matching pink nylon, seamless cup cutie. As was agreed before with El and Joan, I used 4 socks rolled up for each bra cup. No Dolly Parton look for me. Again rolling up my special "Boob" socks my way, to satisfy how I would fill out El's cheer sweater. A simple pleasure it was to squeeze my false breast in the bra for a symmetrical look. I had El's purple cheer sweater to put on to complete my Halloween costume. Mmmm.....I loved the look that greeted me in the mirror. The sight of ample breast jutting out proudly in front furnished me another thrill. Boy haircut but a female body to me! No wig for this Halloween. I came out of my room to El's to use her makeup. An audience was starting to form. "What will it be today for makeup my dear sweet little sister?" So many smart asses in my family. "Mascara and lipstick." "Which color lipstick?" "The one that doesn't make me look cheap. Frosted Pink" The twins and Joanie started howling at my zinger. El just had that smirk on her face that runs in our family. I started with the mascara, looking close in her mirror as I worked very delicately with the wand. Applying it was easy for this 11 year old boy with a history of wearing female clothes. I could immediately feel the heaviness of the mascara of my eyelashes. "Nice job 'blank'. You look like a natural doing that. Try my blue eyeshadow next" "It's mascara El. I'd like to think I am smarter than mascara". Blue eyeshadow was the color of the day back then. "Paint within the lines" said Joan. Painting within the lines, I wasn't sure if I was looking into the eyes of a boy anymore. How many times have any of us seen a woman/girl apply lipstick? At home, television, the movies? Not real difficult to master but plenty fun. Even at age 11, I knew what colors appealed to me. Frosted Pink was absolutely gorgeous! ........................................................................ To be continued

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Sorting Out Part 3: Halloween 1971 By Margaret Rene Claire I remember it was the following fall after my first time "outside" dressed completely as a girl during 6th grade at Halloween 1970. Now it was one year later, and I was12 years old and in 7th grade. My older sister was now a senior in high school and my younger sister was in 3rd grade. I had relegated dressing up to just once or twice a month when no one was home. When my older sister was working or doing something with...

1 year ago
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Shibuya Halloween Part I

Hi, this is Hye-jin again, the young Korean-American with a passion for sheer stockings. After my stocking adventures in Jamaica and nuru massage experiences in Tokyo, I thought of another opportunity to push the limits of daring ecstasy - flashing in stockings during Halloween in Japan. In Japan, it’s Halloween mania during the month of October, particularly in the Shibuya district of Tokyo. I would have the perfect chance to wear my sexiest lingerie and finest stockings out in public without...

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3 years ago
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Accidental Slut A Halloween Party

Hi! My name is Mollie and I'd like to tell you all about the Halloween party at my brother Jake's house.Wait...Let me back up a step or two.Picture a gorgeous 19 year old with huge 36D melons and a perfect bubbly ass and gorgeous green eyes and the whitest blonde hair that naturally curls all the way down to the top of my butt.At least, that was what I was going for. The original costume. Before I lost the blonde wig that would have covered by straight brown hair that comes about half way down...

4 years ago
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Best Halloween Ever part 1

Best Halloween Ever - part 1 By strangefun It started innocently enough, with the office Halloween party. I was working as an IT contractor for a small marketing company, and in the office with four girls I was the only guy, which made me popular. The girls enjoyed a "presence of a man" and were extra giggly and dressed-up on the days I was in the office. They were all young, including the owner, and very attractive. What they didn't know, or at least that's what I thought, that I was...

1 year ago
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Julie and Moms Halloween Party

After Klintuck and I visited mom, we went back to our place, Klintuck’s ship, and mostly just relaxed for a few days. It was getting close to Halloween so most of my attention and energy was drawn to figuring out what to do for one of my favorite holidays. I wanted to have another Halloween party, like I had gone to with mom so many years ago, but now I wanted to host my own. I wasn’t sure as to where I was going to have it quite yet, but I figured with it being close to Halloween, I would...

Trans
3 years ago
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Fifty Years of Halloween Costumes

An elderly couple loves Halloween, almost as much as they love one another. Sadly and tragically, Bonnie and Andy never had children. She couldn’t because of a horse riding accident that happened to her when she was young, a lifetime ago. Ironically not fair that those couples who should have children don’t and those couples, who abuse their children have an entire brood. Who knows, maybe had they had an entire brood of children, they would have abused them, too. I don’t know. A gift and not...

3 years ago
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Bewitched at a Halloween Party

Looking back at some of the crazy shit we used to do when we were younger, I'm amazed that most of us are still alive and have maintained our sanity, what little we had to begin with anyway. Thirty some years ago, several friends and I threw what turned out to be one crazy Halloween party at which I was bewitched. Although parts of this story are based upon what happened at several different real parties, a large part of this story is completely fictitious and a product of my over active...

3 years ago
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The Halloween Party

Gina Matthews was a pretty ordinary girl with a pretty ordinary life. She was eighteen years old, a freshmen at Westhaven University, and a server at a fast food restaurant that wasn't well known or very successful.However, her ordinary life would completely change when she was invited to a party by a cute guy named Josh Kelman.Gina was walking through a campus hallway one evening when Josh approached her. He held out a black and orange card to her."Hey, Gina, I'm having a Halloween Party this...

4 years ago
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The Halloween Party

Gina Matthews was a pretty ordinary girl with a pretty ordinary life. She was eighteen years old, a freshmen at Westhaven University, and a server at a fast food restaurant that wasn't well known or very successful. However, her ordinary life would completely change when she was invited to a party by a cute guy named Josh Kelman. Gina was walking through a campus hallway one evening when Josh approached her. He held out a black and orange card to her. "Hey, Gina, I'm having a Halloween Party...

College Sex
2 years ago
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Ghost story for halloween

I_'_m _ n_o_t _ a _ v_i_r_u_s_. _ I_'_m _ a _ g_h_o_s_t_. L_o_o_k _ a_t _ t_h_e _ k_e_y_b_o_a_r_d_. _ _ T_h_e _ k_e_y_s _ a_r_e _ m_o_v_i_n_g_. C_o_u_l_d _ a _ c_o_m_p_u_t_e_r _ v_i_r_u_s _ m_o_v_e _ t_h_e _ k_e_y_s _ o_n _ y_o_u_r _ k_e_y_b_o_a_r_d_?_" Good, you believe me. That makes things a lot easier. And, no, you don't have to type, I can hear your thoughts. That would be a dog. As I said, I am a ghost. I know that, for the past several weeks, you have been trying to...

2 years ago
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Hot Lactating MILF in Overalls Gangbanged at Halloween Party

My name is Jason, and my wife, Katie, and I are in our mid-thirties now, still living a cuckold lifestyle, that began with us agreeing to try swinging with our close friends, when I was twenty-seven years old, Katie was twenty-four. Our daughter was only five months old then, and Katie was breastfeeding her.Katie and I live in Memphis, where we moved when we got married, right after graduating from UT; me with a law degree, and Katie with an accounting degree. I was recruited by a law firm in...

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