Sissy Son Story

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Sissy Son Story

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“I'm In Such Pain From Loving You” by Linda Ronstadt, Dolly Parton, and Emmylou Harris
Chicago performance artist John Conners reads from a 1942 book called How To Improve Your Personality , from a chapter instructing men on how to avoid being sissies. (6 minutes)
Chicago writer and actor Dave Awl , who runs a show called the Pansy King Cotillion, on how he accidentally discovered how not to get picked on as a sissy in high school. (8 minutes)
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Though being gay no longer has much of a stigma in some parts of the country, being a sissy still does — even among gay men. In this show we have a number of surprising and unusual stories of sissies, their families, and why people still get so upset about them.
This American Life producer Nancy Updike on a family where the father was one kind of sissy and the son was another kind, and how the family was destroyed despite the fact that no one wanted it to be. (23 minutes)
Seattle writer and syndicated sex columnist Dan Savage , on how there's a stigma against sissies even among gay men. Gay personals ads are filled with men who want "straight acting/straight appearing" partners. Girly boys need not apply. Savage prefers swishier men and believes they actually have to be braver than homosexuals who can pass for straight. (15 minutes)
Original musical scoring throughout the hour by The Aluminum Group .
David Sedaris takes Ira on a tour of his favorite spots in Paris.
Favorite stories by our longtime contributor and friend David Rakoff.
This American Life is produced in collaboration with WBEZ Chicago and delivered to stations by PRX The Public Radio Exchange.

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Why I need to get used to being a girl, I’d dress up for a few pictures then change back again. It wasn’t as if I was going to wear girl’s clothes that much right? “What happened to my hair!” I asked in amazement. “How am I going to explain having light blond hair at school?”
I was only sixteen when my life changed. I know now that the change was definitely best for me, but I had serious doubts during the time the change was occurring. I suppose the biggest problem was that I had no idea what was happening to me or why. But before I get involved in some deep philosophical discussion, let me explain what happened. Liked I said, I was only sixteen and in the middle of my junior year in high school. I didn’t have many friends; I stunk at most sports which definitely cut down on the number of guys willing to be my friend. After all, sixteen-year-old boys don’t give much thought to accepting a look like and what they can do. For that matter, so are sixteen-year-old girls!
Since I wasn’t very good at much and at five foot five inches and one hundred twenty-five pounds, I didn’t look like much; I was pretty much on my own. I tried dating some of the girls in school but got nowhere; the nice ones said they thought of me more as a friend than a boyfriend and the others just laughed at me.
One thing that helped me, though, was that I was very good at acting. I had been with my high school drama group since I was a freshman and had parts in nearly every play the school put on.
This time our junior class was putting on a play called “Charles Aunt,” and I managed to land the lead role. The title of the play referred to the lead character having to pretend to be his elderly aunt throughout most of the story, so I would have to spend a good deal of time dressed like an old lady.
Up until now, all of the rehearsals had been in regular school clothes but next week was to be the first of many dress rehearsals, so mom and I began to work on my costume, an ankle-length dress, and gray wig. We were busy getting things ready the day her friend Shelley dropped by for a visit.
I was standing in the living room wearing the dress over my jeans while mom pinned the hem when the doorbell rang. Mom went to answer it while
I heard the excitement in her voice and wondered what was up. A minute later, I got my answer when she returned to the living room with Shelley in tow. In her excitement over seeing Shelley again, mom had forgotten that I was in costume.
Shelley took one look at me and laughed.
“That dress really doesn’t do anything for you, Jim!”
I’d known Shelley since I was a little kid and had always enjoyed joking around with her son, put my hands on my hip, and began to mince around the room.
“Are you sure about that ?” I asked in my highest voice. “I thought it was just perfect!”
I broke into an exaggerated version of the “Can-Can “ lifting and
“You’re great, Jim,” Shelley laughed, “but why the dress?”
I explained about the play and how I had the lead part. Shelley complimented me on getting the lead, but mom didn’t seem so happy. “If you could find a way to make some money, it would be a big help.” She said. “Acting jobs are not easy to get you to know.”
“I’m only sixteen, mom,” I replied sadly. “When I’m out of school, I’ll be able to make some money by acting!” Mom smiled, “I understand dear, It’s just that we could use the extra money now.”
“How would you like to work for me this summer Jim?”
“Doing what, Shelley?” I asked curiously.”I guess you could call it an acting job.”
I should have known better, but I snapped at the bait.
“What kind of an acting job did you have in mind?”
Shelley seemed just a little evasive in her reply.
“Well, let’s just say it would involve some modeling for my clients. Are you interested?”
“I know I’m a good actor and of course I’m interested! I could easily stand there looking cool while getting my picture taken!”
I didn’t expect Shelley to jump for joy, but a smile would certainly have been nice. Shelley, however, just stared at me.
“That’s hardly a challenge for an actor as good as you.” She said coolly. “Besides, you really don’t measure up for that cool look.” That hurt! I didn’t see any reason for her to be nasty after just offering me a summer job! Shelley saw the hurt look in my eyes and went on to explain.
“I’m not trying to be mean, Jim.” She said as she picked up a tape measure mom was using. “Here, let me show you what I mean.” She measured my height and wrote that down, then took measurements of my thighs, my hips, chest, waist, and biceps. She asked me my height and weight and read off the figures as she wrote.
“Biceps 4 inches, thighs, 10 inches, waist 25 inches, chest 32 inches, hips 30 inches, height 5 foot 5, weight 125 pounds.
“So I’m a little on the scrawny side, but what does that matter? I mean, I can act as cool as the next guy!”
“You probably could, Jim, but you wouldn’t look as cool as the next guy, and that’s what counts how you look, not how you act. People can’t see your acting; besides, the cold, hard truth is that my clients want to see the All American Boy type standing around looking cool. You just aren’t that type!”
“Okay, I give up. If I don’t look like the All American Boy and my acting was not going to help, how could I possibly work as a model?” Suddenly I felt a cold chill run down my spine. It was painfully obvious, but I had to be wrong! It’s just that I knew what Shelley was going to say even before she opened her mouth. Shelley looked me right in my baby blues.
“Well, there is another part you could play if you’re nearly as good as you think.”
“You’re not thinking what I think you’re thinking, are you?” I asked, trembling.
Shelley continued looking me right in the eye as she spoke.
“I think you can guess that, can’t you, Jim?”
What else could it be? If I wasn’t the kind of boy she was looking for
then I must be…, no, that’s just too crazy!
Before I could say anything, mom interrupted.
“She has a point, Jim, here look at these measurements.”
I looked at the sheet and noticed that Shelley had circled some of the measurements that she had taken. That chill began to form along my spine again as I saw what was circled — Bust 32 inches, waist 25 inches, hips 30 inches.
“Bust, waist, and hips are not measurements for a boy Shelley!
Especially since I don’t have a bust!”
You’re right, Jim; those aren’t measurements for a boy, but yet they are your measurements!
You’re a skinny little runt of a boy Jim.” Shelley said in a soft
voice. “But with a few adjustments, you’d make a great-looking girl!”
I tried to end the discussion as best I could without hurting Shellys feelings.
“I appreciate the offer of a job Shelley,” I said as nicely as I could.
“It’s nice that you think I’m a good enough actor for the part, but no one would ever believe I was a girl even if I wanted to try! Shelley just smiled at me.
I should have known better, but I shot my mouth off anyway.
“Name it!” I said in as macho a tone as I could muster!
Shelley coolly told me that if she couldn’t make me look good enough, she’d give me fifty dollars. If she could, however, I’d go to work for her. I figured I had a quick fifty bucks coming my way, but I wanted to stack the deck as much in my favor as possible. I picked up my past school year’s yearbook and, after a moment, found just what I was looking for — a picture of the prettiest girl in the school.
“Here’s the deal,” I said as arrogantly as possible. “If you can make me look like her I lose; if not, you owe me fifty bucks!” I was sure I had Shelley beat; this girl had shoulder-length blond hair, a figure that made guys stop and stare, along with a smile that could double as a lighthouse! In the picture, she wore a green velvet dress with a lace collar.
Shelley looked at the picture for a moment then put the book down.
I’ll do it.” Mom stated. “I promise to be fair!”
“Does it have to be that dress?” Shelley asked.
“I’ll forget about the dress,” I said graciously. “But that’s it!” I meant, of course that I just wanted Shelley to make me look like the girl and not worry about clothes. Shelley had other ideas, though.
We shook hands on our bet then Shelley left, saying she had to pick up a few things. She promised to be back in a little while to win the bet.
I wasn’t worried, just amazed that a smart woman like her could have agreed to the kind of terms I insisted on. What could she have been thinking?
Mom finished fixing my old lady costume, and I went to my room to study for the play. It was about two hours later when Shelley stuck her head in my door and asked if I was ready.
“I hope you stopped at the bank; I expect to get my money right away!”
“Just follow me,” Shelley replied, “You haven’t won yet!”
I followed her to Mom’s room, where I was surprised to see that the full-length mirror was covered up, as was the one on the dresser. I asked why but Shelley told me to strip to my shorts and not to ask dumb questions.
I was uncomfortable about standing there in my underwear, but I consoled myself by thinking of what I was going to do with my fifty bucks.
Shelley placed a bra around my chest, fastened it, and stuffed some tissue into the cups. Next, she had me put on a pair of pantyhose followed by a half slip.
I decided things were getting out of hand and wanted more control. “I told you the clothes weren’t necessary!”
Shelley made no reply; she handed me one of Mom’s robes and told me to come with her to the bathroom. Once there, she made me stick my head in the shower while she rubbed some shampoo into my hair. after making sure it was worked in completely, she rinsed my hair, and we were off to the bedroom again.
Shelley had me sit at the vanity while she dried and styled my hair with a brush. It felt so good to sit there and have her fuss over my hair that I hated to have it end. I tried to stop her when she began to apply makeup to me, but mom told me to sit still.
“You picked the terms, remember, now play fair and let Shelley try to meet them!”
I wasn’t happy about it, but mom was right so I let Shelley continue making up my face. First came to cleaning with a liquid which stung like crazy then a second liquid was smeared all over my face and neck.
This was followed by the application of blush to my cheeks, mascara to my lashes, and eye shadow to my eyelids. As a finishing touch, I had a maroon-colored lipstick applied.
Shelley then had me stand up and remove my robe. Just when I thought it couldn’t get any worse than standing there in a slip, bra, and stockings Shelley went to the closet and brought out a pink dress with lace-trimmed sleeves and collar.
“I was ready to give up,” Shelley said. “When I remembered that I had this outfit back at my studio! Lucky huh?
“Yeah Shelley,” I said dripping with sarcasm. “Lucky for me!”
Mom unzipped the dress and lowered it over my head, taking care not to screw up my new hairdo. She straightened it out, zipped up the back, then had me step into a pair of pink shoes. Mom helped me to stand up while Shelley uncovered the mirrors. I didn’t really want to look in the mirror, I was afraid of what I might see. I had plans for that money and was scared silly of what would happen if I lost the bet.
I heard Shelly’s voice but couldn’t bring myself to look.
“ Come on Jim, open up.” Mom pleaded. “Don’t be a sore loser!”
I was so stunned that mom had sided with Shelley that I opened my eyes.
Staring back from the mirror was a pretty blonde-haired girl in a dress, stockings, and heels. I blinked hard, took a deep breath, and looked again. Although it wasn’t the girl from my yearbook there was no denying that I had just lost fifty bucks! “What happened to my hair!” I asked in amazement. “How am I going to explain having light blond hair at school?”
Fortunately, Shelley explained that my new hair color would come out with shampoo so I wouldn’t have to explain anything. The only thing left was to admit defeat.
“Okay, you win. I just hope no one sees me like this.” Shelley told me that to be perfectly honest there was no way to tell how many people would see me dressed as a girl. My picture would be used by a national department store to promote their line of clothes for teenage girls. I would be included in the Sunday paper in millions of homes across the country. I was about to die when she explained that no one would ever know it was me. As far as anyone was concerned I would be just another pretty model.
“Trust me, Jim,” Shelley said. “The way you look right now is nothing compared to what you’re going to look like. I have a feeling that you’re going to make a lot of money for me!”
“What about me?” I shot back. “I just lost fifty bucks and now I’m going to have to pose in front of a camera in girls’ clothes. What do I get out of this?”
“How about $400 a week for a paycheck?” Shelley coolly replied.
Four hundred dollars a week! Good grief, that’s more than my mother made as a secretary. I was already dreaming of ways to spend that much money and had to work really hard to remember what I had to do to earn it.
Shelley explained how I’d get paid and what I’d have to do to earn it. She rattled off figures that made my head spin as if talking about pocket change.
“But what will the guys at school say about me? I’d be ruined!”
Shelley looked at me as if I was joking.
“This isn’t something I’d brag about to my friends if I were you!”
“I wasn’t planning to. “ I replied. “But what if one of the guys from school sees me?”
“He’d probably ask you for a date!” Shelley laughed. “Trust me, you’re going to become a gorgeous model, no one would ever believe you’re not a girl!”
Mom put her arm around me and held me tight.
“It’s up to you Jim, it has to be your choice. If you want to give it a try and think you could do it I’ll help any way that I can.” I was totally confused at that point, I wanted that money so badly I could practically feel it in my hands. All that I had to do was to pretend that I was a girl and have my picture taken. Once I got done I’d go back to being a boy! Sure it would be easy, just another part in another play! I told myself that over and over again hoping to convince myself that it was true.
Shelley and mom would make certain that I was ready, I’d have to spend the next couple of months practicing to make sure that everything was perfect. Since Shelley had clients lined up for the rest of the summer I wouldn’t be able to quit before the end of summer.
After talking everything over Shelley had to leave but promised to be back soon to help me get started. She certainly lived up to that promise by showing up bright and early the next Saturday carrying several bags from a local discount store.
Shelley told us that she had stopped to drop off a few things that I would need to get started and began to unpack some of the bags.
Shelley unpacked a couple of pairs of girls’ jeans and tops along with enough dresses, skirts, and blouses for several girls! Shelley told me that I could wear jeans occasionally but I was to spend as much time as possible in a dress or a skirt so I got used to being a girl. I couldn’t imagine why I need to get used to being a girl, I’d dress up for a few pictures then change back again. It wasn’t as if I was going to wear girl’s clothes that much right? I was grateful for the jeans even if they were girls, I only owned two pairs of jeans and I hated to wear anything else but them! I wasn’t quite as grateful though when Shelley handed me a bag full of panties, bras, slips, and stockings and insisted that I wear them anytime I wore girl’s clothes which she stressed was to be anytime I wasn’t in school!
I complained that I couldn’t do that I just couldn’t be wearing girl’s underwear when I was fooling around with my friends but mom scoffed saying that I didn’t have any friends to fool around with anyhow! I was to wear panties to school and change into one of my dresses when I got home, if I had to go out for anything I’d wear my new jeans and save my boy’s clothes for school. I had a sick feeling in my stomach that something was going very wrong, mom and Shelley just seemed too intent on making a girl out of me.
Mom would help me by teaching me the basics of being a girl like walking, sitting, setting my hair, makeup, and other small things l while Shelley would provide the polish I needed to be a model. This polish would be along the lines of walking in heels, coordinating my wardrobe, fancy hairstyles advanced makeup, and how to pose as a model.
One last thing remained before we were finished — my name. Jim just wasn’t an appropriate name for a girl so after much debate I was rechristened Janice Lynn Marshall, the last name being mom’s maiden name to avoid any chance of my being recognized.
She promised me that she’d drop by from time to time to check up on me and expected to see Janice when she did.
After Shelley left I took my clothes to my room to put them away. It felt odd to see brightly colored nylon panties next to my DVDs and really strange to push the few shirts and slacks in my closet aside to make room for all my new dresses. Mom insisted that I change into my new clothes and picked out a dress for me to wear along with a slip, panties, bra, and stockings. I took my time getting changed, needing Mom’s help to put on my padded bra. Mom remarked that the cup size seemed a little small but after stuffing them with stockings she seemed satisfied. Mom asked if I wanted her to show me how to put my stockings on but I said that I wanted to try it myself and after a few minutes of fumbling I managed to pull on a pair of tan on
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