Cross-Country - Part 2 of 7

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I stole a girl’s dress. It was the worst thing I’d ever done—and the best!

Cross-Country, by Karin Bishop

Part 2

Chapter 3: The Shopping Trip

After parking at the mall, Mom turned to me and said, “I just realized that I don’t know your sizes, and neither do you! Let me think.”

I figured the whole expedition was doomed, and was afraid she’d get cold feet if we let too much time pass after leaving the doctor’s; I feared Mom might cool on the whole idea. Then she started fishing through her purse.

“Let’s see if I …there you are!” She pulled a cloth measuring tape from her purse, neatly folded and held with a rubber band. “Always good for emergencies! Okay, let’s get out on this side so the car blocks anyone from seeing, and I’ll take your measurements quickly. Here’s a pad and pencil; it’ll go faster if you write them down as I call ‘em out.”

Her purse seemed magical, producing the items we needed; I thought of the old cartoons of Felix the Cat reaching into his bag of tricks! She wrapped the tape around my chest, my waist, my hips, my legs, everything she thought we might need, and I dutifully wrote down the measurement. We sat back in the car while she wrapped up the measuring tape and checked my notes. I was still uncertain how she’d get sizes from the numbers, when she started explaining.

“First stop will be the Penney’s catalog department. A lot of rural America only shops by catalog, so they have diagrams there to convert to the proper sizes.”

I hadn’t thought of this; I’d certainly seen the silhouettes with horizontal measurement lines when I had been looking at the Juniors section of the catalog, and I could see how she was going to pull it all together. Suddenly she stopped writing and looked right at me with a worried expression.

“I just thought about something else we haven’t discussed. Your name!”

“What do you mean?”

“If you’re going to spend some time as a girl, I can’t very well keep calling you ‘Bobby’ oh, I suppose I could call you ‘Bobbi’ with an ‘I’, but that sounds just the same and might get some people wondering, so what are your feelings?”

“Definitely not ‘Bobbi’. I hate that! Well, maybe I hate it because it reminds me of being a boy, but ... Mom, if I had been born a girl, did you have a name picked out?”

“Well, yes, sort of; your father wanted ‘Mary’, but I thought that was too old‑fashioned. I kind of wanted ‘Ann’ since it was my mother’s name, but that seemed old‑fashioned, too. Then we thought of ‘Mary Ann’ and that’s as far as we got, because that’s when the doctor said you would be a boy. And now that I think of it, I guess maybe he was wrong!”

We laughed at that; I was amazed at how well she seemed to be adjusting. She then asked, “And what about you? Do you have any name that you prefer?”

“This might sound strange, but I never settled on a name. I first thought of ‘Susan’, but that’s my cousin’s name, and two of us would be confusing. I thought of a bunch of ‘M’ names; ‘Melissa’ and ‘Melanie’ and ‘Melody’ and tossed ‘em all. Maybe ‘Sharon’; maybe ‘Sheila’; I don’t know. It’s kind of embarrassing, since this is so important to me. Actually, I think I never really settled on a name because it never seemed like it could really happen, you know? And I’d be wishing and hoping too much and it would hurt too bad if it never came true.”

“Well, it’s a real possibility now, and seems like it might come true. You don’t have to decide this minute, you know; so you can experiment a little. People usually get stuck with a name at birth and that’s it for life; you get the luxury of ‘trying one on for size’, so to speak. But if we’re going to start right away like the doctor said, you should pick a nameeven if we change it laterbecause it’ll be difficult shopping and talking without a name for you.”

“You’re right, but I’m so amazed at how you’re taking all this, and it makes me love you so very much, that maybe I should start with the names you’d picked for me. I think Mary’s a bit much, because of the old George M. Cohan tune, but ‘Ann’ ... that could work. Depending on my mood, I could be Ann or Anna or even Annie. Mom,” I said, sticking out my hand to shake, “shake hands with your daughter Ann.”

I could see a tear form at the corner of her eye and I started getting a little choked up myself. We shook hands, burst out laughing, and hugged. Then we got out of the car and entered the mall.

Since I was dressed as Bobby, we decided on a strategy where I would pretend to be reluctantly tagging along as Mom picked up some clothes for my ‘sister’. We’d visit some stores and I’d check things out, we’d discuss them, then she’d return to make the purchase. We spread out our purchases over several stores. Mom had a good eye for sizes, so she didn’t have to expose us by holding something up to me for size. She said she could take things back if they didn’t fit, but our measurements in the parking garage gave her enough to shop confidently.

We picked up some zippered jumpers, in brown corduroy and a herringbone, a couple of turtleneck blouses, tights in white, blue, black, and brown, a yellow gingham shirtwaist dress (“Humor me,” Mom said), a peasant blouse (Id admitted Id always thought they were so pretty), some beautiful sweaters and tops, some leggings and a few tunic tops, a couple of skirts, and I persuaded her to add a denim miniskirt. For casual around-the-house she picked up some shorts and tops, a couple of cute t‑shirts, and an oversize sleep shirt.

As we loaded up from each of the stores, we took the bags back to the car and went back for more. I couldn’t believe how much money Mom was spending, but I wasn’t about to question it because the magic might end.

After our fourth trip to the car, she said it was time for shoes; our plan this time was that she would use that odd metal gadget to measure me, then we’d go somewhere else and she’d pick out a few shoes for me at several different shops while I tried to act like the bored son, dragged along while she shopped for ‘my sister’. There was a discount shoe place that she went to last, and she got to work. We found some black flats, white flats, some strappy sandals with a little bit of a heel, and some oversized ‘foofy’ slippers for bedtime. I wanted to go right into heels, of course, which she vetoed, but she did allow some very hip Mary Janes with a 2" heel. I didn’t want to push it beyond that. As an afterthought she threw in some white Keds of my own.

Back at the car after unloading the shoes, she said she was tired and hungry; did I want to try the food court now? I heartily agreed; I’d only had the salad and was starving. After all, we’d walked all over the mall several times going to all the shops; we’d gone to four stores looking at shoes alone!

At the food court, I decided on soup and half a sandwich, which she approved.

“This may come as a shock to you,” she said with a grin, “but you’re going to have to start watching your figure!”

I laughed with her and then got serious. “Mom, this must be costing a fortune! I mean, the clothes, the doctor, and all ...”

“Don’t worry about it. I’ve got some money saved up for a rainy day, and after all, you can consider this a sort of ‘new birthday’, can’t you?”

I was so happy, but realized that we’d forgotten something. “Mom, I’m so grateful for all you’ve spent today, but, well, what about undies? I mean …”

”Your lingerie, you mean? You’ll have to get used to the real words for things, honey! I haven’t forgotten; I wanted to discuss this with you before we plunged in. A girl your age would already be developing her breasts, so she would have several beginner bras. We’ll find you a few padded bras, and you’ll have to stuff, but most girls your age do, anyway! You’ll need panties, of course, and there’s a wide variety to choose from. We already got tights, and I think it’ll be a while before stockings or—”

She read my mind, obviously, or the disappointed look on my face. “Alright, pantyhose, but only one pair, and only for dressy occasions, young lady!” She thought about what she’d just said. “That felt good. ‘Young lady’ …I liked saying that!”

“Well, you’ve said it before,” I offered, lamely.

“I know, but that was kind of ‘taking it out for a test drive.’” She grinned. “Now, it’s medically approved!”

We ate some more while she discussed other lingerie needs. I talked her into a leotard, even though I wasn’t taking a dance class; I’d always wanted a light blue leotard with short capped sleeves and a gathered bodice, with white tights. She thought it’d be okay as another outfit if I wore it with a wrap skirt or denim skirt—and I ‘might take a dance class somewhere down the line’, she said—so she approved it. We talked about what I might like to sleep in; I told her that since I had longed to be a girl all my life and had thought about it every single night of my life, I wanted frilly girl sleepwear like nightgowns, peignoirs, and so on. She laughed and said I’d soon learn to appreciate flannel pajamas, but she could understand my desire to be feminine, especially while I sorted out what kind of girl I’d be and what kind of styles I’d wear. That led us to what I would be doing with all these clothes.

“I’ve been thinking about your odd situation; you’ll have to continue in school, of course, so you’ll be Bobby there, but you can become Ann when you get home. But what are you going to do at home?”

“Well, my homework, of course. Housework …you’ll have to start teaching me stuff a girl should already know; cooking and sewing and the laundry and stuff. If we can go where we won’t run into anyone we know, maybe we could go for a walk or something.”

She thought about that. “We’ll see how you look, and how you feel, and I’ll have to check with the doctor, of course. Well, let’s just take each day one at a time. If you’re finished with supper, let’s get your lingerie and get home. Then comes the fun part!”

“Fun part?”

“Yes, silly—my Annie’s going to have her first fashion show!”


Chapter 4: Mom Meets Ann

Mom told me to put all of our purchases in the living room, and we went to study my room. She thought that we shouldn’t completely remodel it into a girl’s room while I still had to spend time as Bobby; although I didn’t really have any friends and certainly didn’t have other kids over, ‘you never know’, she said. But we could go for more neutral colors. It was already white with beige carpeting, and she thought we could keep the bed frame but should add a desk where I could do my makeup and stash my jewelry.

“That comes later, of course; jewelry’s too expensive to experiment with, but I’ve got a variety of pieces you could try out. But we need to make your desk a study area that can convert to a girl’s needs, but still be able to pass as a boy’s if you have any friends over. Thats why I think we shouldnt get a vanity yet.”

“Mom, like I’ve got friends, and when’s the last time anybody came over?”

“Honey, that’s one of the ways that I knew you weren’t happy. I just never imagined it was because of …what’s Dr. Livingstone’s official name? ‘Gender Dysphoria’. But it all makes sense now. Well, if you’re sure that no one will get invited over, we can gradually change Bobby’s bureau and desk into Ann’s. We’ll add a genuine vanity later on. Right now, though, I’ll get a bag and we’ll go through your boy clothes to give anything you don’t want to the Goodwill. We’ll rearrange and make room for Ann to move in!”

For nearly an hour we sorted, tossed, consolidated, packed away, and generally reduced Bobby’s existence in my room and closet. As a boy, I just wore jeans, t‑shirt, and a shirt over that; the rest were excess unwanted clothing from Christmases past, for example. Finally, it was time to un-bag all my new clothes. Mom showed me the special hangers for skirts and blouses, how to fold sweaters, and how to fold and arrange my lingerie. My lingerie!  That felt so delicious to say, after all these years of desire!

“And now it’s time for your fashion show! Now, you can’t try on everything, of course, because it’s late and tomorrow’s a school day. Unless you’d rather wait until tomorrow after school?”

“Mom, I’m totally excited and could stay up for hours trying everything on, but I’m also exhausted, and I know you’re tired, too. This is what I’ve wanted for my whole life, and now that it’s here, maybe I can relax a little.”


“Well, only a little! Tell you what: I’ll wash up and try on my new nightgowns, that’ll be our fashion show, and then tomorrow you’d better be ready for a full‑scale fashion show!”

“You know what, honey? I think you’re growing up!” She started to grin broadly. “What can I say? My little girl’s growing up!”

We laughed and hugged, and she went to make some tea while I washed up. I couldn’t resist using some of her skin cream, and looked forward to having my own cosmetics on a shelf next to hers. I brushed my hair straight back, thinking that I’d have to start learning hair care and ‘brushing 100 times’ and all the rest. My hair was wavy and now reached my collar; I was sure I’d had the last haircut I’d have for awhile. Once again I was glad that long hair on boys was acceptable, but of course I couldn’t style it the way I wanted to ...I used one of her headbands to hold my hair back, and went to my bureau to choose a nightgown.

I chose the frilliest pink one, of course, pulled on some matching panties, and the foofy slippers. Mom was in the living room enjoying her tea, and I decided to wait until she’d put the cup down before making my entrance. It was worth it; I could tell she was genuinely shocked. As she stared at me, I suddenly got shy and nervous and was intensely aware that I was standing in front of my mother wearing only a girl’s thin satin nightgown. I felt incredibly naked and realized I had unconsciously adopted every girl’s stance when she felt vulnerable: my knees jammed together and my arms crossed in front of myself.

“Oh, honey, oh ...” Mom sputtered to silence, then shook her head. “I had no idea. No idea.”

I didn’t know what she meant. “Oh, Mom, I’m sorry; I’m sorry if you don’t like it; I’m sorry the whole thing is …” I broke down, blubbering.

“What are you talking about? No, I do like it! I love it! I just had no idea how natural you look as a girl. As Ann. Oh, Annie, honey, don’t cry! I just wasn’t expecting that you’d be so naturally feminine, and such a pretty girl; that just takes a bit of getting used to!”

She stood up from the couch and came to hug and comfort me. For a moment I nestled in her arms and forgot about how old I was, forgot about what gender I was, forgot everything except just resting in the safety and love of her embrace. I truly don’t know how long we stood there, hugging and gently rocking. I sort of ‘came to’ when I realized she was softly singing, “Hush little baby, don’t you cry”. Talk about reverting to my youth!

We ended the hug and she handed me a Kleenex—she always had one ready somehow—and I dabbed my eyes. But I did it as Ann. In some strange way, my little breakdown and our long hug had taken us across a boundary of some kind. We’d crossed into a new land where Ann lived; I couldn’t put it any simpler than that. Any worries or fears I’d had that Mom wouldn’t accept me, or that I should ‘pull back on the girly stuff’, or that I should act tomboyish or just neutral …all thoughts like that were gone. I could be me—Ann.

I decided that after that emotional moment, any fashion show would be anticlimactic, so I hugged her, thanked her, told her I loved her, and went to bed. I thought it would be difficult to get to sleep, with all the excitement, but I went under immediately, because for the first night of my life, I didn’t stay awake thinking about being a girl, and praying for God to make me a girl. That day I’d awakened as Bobby, but finally slept as Ann.


Chapter 5: Day By Day

The next few months were wonderful and bizarre. Each day I’d awaken in my nightgown, take a shower, make my breakfast and dress in Bobby’s clothes. I found that I was thinking and talking about Bobby in the third person and had to be careful around other people. I’d wear Bobby’s clothes and ride Bobby’s bike to school, and everything was like it had been, but I didn’t have to look and think about the girls with such envy. Instead, I studied them. I studied every possible thing I could: how they talked, walked, ran, held things; what they did with their hands, their arms, their legs, their feet; how they moved their heads and body when talking or doing things; and, of course, what they were wearing, their clothes, and their makeup. It was kind of a daily crash course in girlhood.

You’d have thought I’d be too busy studying the girls to study in school, but the strange thing was that my grades improved. They’d always been pretty good, B stuff, but they started to climb even higher! All I could guess was that I was generally happier than I’d been before. After school, I biked home alone like always. Unlike what I’d told Mom, I actually didn’t have any friends; I was friendly with most kids and they with me, but not really close friends. How could I ever have really close friends? The only ones I’d want would be girls like Jane, Dawn, Melanie, and a few others, but that was only if I was just another girl. Well, when I got home each day, I was just another girl.

Once I got home, I’d strip and wash, occasionally taking a shower. Baths I reserved for later at night when Mom was home. After drying, I’d apply moisturizer and a dab of cologne (I’d liked ‘Trésor’ after smelling it in a magazine, and Mom managed to get a little free sample from Nordstrom), brush my hair out and then get dressed. I probably dressed better than the average girl did at home; I knew girls that immediately got out of school dresses and right into jeans and t‑shirts. I was the exact opposite. I’d put on a top, tights, and a jumper with flats; another time I’d wear a chenille pullover with leggings. Occasionally I’d wear the shirtwaist dress Mom had insisted on; I always felt like June Cleaver but discovered that, what the heck—some days a girl just felt like June Cleaver!

I’d do my homework and then do jobs Mom might have left on a list. These were usually small things like taking care of the laundry, or scrubbing the bathtub, or whatever. I’d change from my ‘homework’ clothes to my ‘housework’ clothes, which might actually be jeans and a t‑shirt if the job was dirty, but took care with my hair, usually tying it in a kerchief or pony tail. Some kids at school had started to comment on how long my hair was, but they actually approved as a counter‑culture, ‘hippie or rocker kind of thing, never guessing the real reason. I found that my hair was getting long enough for a decent ponytail that I could actually feel move when I walked! It was so strange and delightful the first time I felt it, and I began to really experiment with hairstyles now that I had enough to work with. Of course, I had no skills, but like every teenaged girl I had that software program, hairstyle magazines and determination!

As the weather began getting warmer, I switched from jumpers to skirts and shorts. I cut up Bobby’s jeans to make cutoffs, and the typical boy’s worry that I might cut them too high didn’t apply—I wanted cute cutoffs! The only problem was that I couldn’t shave my legs while I still had PE as Bobby, and although I didn’t have much hair anyway, it still was enough that it bugged me. Even though I knew lots of girls didn’t shave their legs, I wanted to be as feminine as possible, and longed for the day when I could shave my legs and underarms. With the warmer weather I could wear sleeveless tops, and even a short midriff top, but couldn’t go out back in the sun because the neighbors might see, and I might get tan lines that would be hard to explain in the boys’ locker room!

Often I’d experiment with makeup and nail polish, but I was always careful to remove it before bedtime. One night I’d been too sleepy to remove my nail polish, and then overslept in the morning. I had to have Mom call from work to tell school that I’d be ‘officially’ late, while I was frantically removing all traces of the polish. After that I vowed to only use polish on weekends! My nails were growing, since I used to be a nail-biter, but I had to carefully keep them just long enough that they didn’t cause comments at school. By and large, I just tried to disappear at school.

In fact, I found that by thinking of Bobby in the third person, he became less real, and I moved through my school day as a ghost. I only really came alive when I could go home and remove the Bobby costume my mom called it ‘our little masquerade’ and could become Ann again. Simply, I began feeling that Ann was real and Bobby was not. Mom noticed that I sometimes seemed a little restless; well, Ann wanted to go somewhere and do something! But I knew that I couldn’t, at least until after school was over. Maybe for summer vacation I could begin to leave the house; we could go to a distant mall where nobody knew us, and shop as mother and daughter. I guess I was going a bit stir crazy.

One night I was in a yellow sundress watching TV. I really loved this one; it had a shirred bodice and wide shoulders so my bra straps wouldn’t show. And, yes, I wore a bra, with two little gel inserts that Mom had produced one night. She’d frowned at them with some displeasure at first and just shook it off as ‘something from my past’ but gave them to me lovingly. It felt kind of fake to put them in, but once they were in, they warmed and jiggled and were the closest thing until I had breasts of my own. So this sundress was my favorite because it had the gentle swell of my bust, and was also short enough to show off my legs.

Dinner was done; Mom was reading the paper and it was just a generally lazy time. Once Mom absent‑mindedly said, “Knees, dear,” reminding me that I wasn’t sitting in the most feminine way. She did this as needed, but I was generally pretty good about keeping my knees together, or about crossing my legs at the knee. Occasionally I’d forget, but more often she’d remind me about sitting and getting up; I hadn’t quite mastered those movements naturally. We agreed it was because I had to avoid those movements during the school day; half-and-half lives was frustrating and kind of confusing. But keeping Bobby in the third person helped, because in my head I was always Ann.

Suddenly Mom looked up from the newspaper. “That new Julia Roberts movie starts in fifteen minutes. If we leave right away we can just make it.”

“But I’ll have to change and we’ll lose time. We’ll never make it!”

Mom looked at the paper, then at me, then decided. “Just grab that white sweater if it gets cold. You’re fine as you are!”

In a daze but quickly I got the sweater and we headed for the garage. As the door was opening, I grabbed Mom’s sleeve.

“Mom, are you sure about this? I mean I’ve never been outside as Ann.”

“No time to waste! Get in the car, Annie, and we’ll talk about it on the way. Julia’s waiting!”

I was just amazed at her. Here I was, Ann, with my hair in a pony tail, wearing a bra and panties, dressed in a yellow flower‑print sundress, white flats, and a white sweater over my arm, going to a movie. No big deal about that, but I was her son!  Of course, I didn’t really feel that way anymore, but I was still afraid that she might think that way. After that first night when I broke down and cried in my new nightgown, I never thought about her questioning what we were doing as long as we were in the privacy of our own home. But how would she react in public? What would she think?

We parked across the street and stood at the end of a line. I was intensely conscious of wearing a dress in public. Then I realized nobody seemed to notice, other than one boy farther up the line. I froze for a moment when I saw him looking at me, and frantically searched my memory to see if I knew him, but suddenly I recognized thelook and the smile he gave me—he was checking out the girl in the yellow sundress! Me!

This was something I actually had never thought about before—boys. Mom kept saying I was pretty, but let’s face it; every Mom tells every daughter she’s pretty. I was kind of surprised how naturally I could look like a girl, and a sort of pretty one at that, but it was still all so new to me that I had no objective way of telling until now. I had actually been scoped out as a ‘babe’ and suddenly I knew that Mom and I and Dr. Livingstone would have a lot to talk about at my next visit. My thoughts were broken by Mom turning to me as we advanced in line.

“I was just thinking we’ll have to get you a new purse. Your old one’s so far gone, it’s like having no purse at all!” she said with a grin and a twinkle in her eye.

I quickly understood. What she was really saying was that I should be carrying a purse right now, like every other girl; we both knew that I had no purse, but she was graciously letting me know that I should have one, and that I’d soon be getting one! She was well aware of the other people in line who might eavesdrop. I loved her so much for her discretion, and I thought my mom could’ve been a great spy, talking in code! I wanted to play along, but wasn’t confident enough in what my voice would sound like, so I just smiled big and nodded.

Once in the theatre, I started heading for the ramps leading to the seats, but Mom pointed down to the restrooms.

“I think we’ve got time before it starts. Shall we?”

Dumbfounded, I followed her into the Ladies’ Restroom. Once, I’d sneaked into the empty Girls’ Restroom at school between classes, but felt like such a guilty burglar that I dashed out and pretended it had been a mistake. All my life I’d wanted to do it as a natural right, and now the first time I got to enter as a girl, I was stumbling around like I was doped up! There were two women at the mirrors, and one stall was free. Mom told me to go ahead, and I walked into the stall, locked it, lifted my dress up and my panties down, sat down, and actually peed in a Ladies’ Room! I wiped, adjusted my dress, flushed and left, just like I’d been doing all my life, but now it was so incredibly different! Mom had found a stall right after I went in, and came out just as I was beginning to panic without her. She walked to the mirrors and handed me a brush although I really didn’t need it with the ponytail. A quick wash and check of her makeup, and out we went to see the movie.

After calming down from my restroom adventure, I watched the film but it felt different somehow, and then I realized that I was watching a movie as a girl for the first time. I found myself studying the male lead, well, differently than I’d ever looked at movie stars. And I really checked out the women in the movies—and the girls I saw in the theater lobby—for style tips. I still enjoyed the movie, and we talked about it on the way to the car, Mom reassuring me that my voice was fine for a girl …when she surprised me yet again.

“By the way, Annie, I told you were pretty!”

“Well, yeah, but—”

“Don’t tell me you didn’t see that boy in line notice you?”

“I don’t know what you mean.” But my heart was racing at the thought ...

“Ah, Annie, if I had any doubts about you, you reinforce how much you are a natural girl. First of all, you’re pretty. Take that as a given. Then a boy checks you out, you check him out checking you out, and then you demurely deny it with ‘I don’t know what you mean’.” She laughed. “Just what every woman has said since the dawn of time! You make me laugh, honey—you’re so naturally feminine and you don’t even know it. No wonder you seem so normal!”

“Hey, watch who you’re calling ‘normal’, buddy!” I said with a mock‑Western sheriff tone.

We were still laughing when we got in the car. She turned to me and said, “Whaddya say to a nightcap? Maybe a raid on Dairy Queen?”

“Sure,” I said, laughing, “But remember—”

We said it in unison. “A girl’s got to watch her figure!”

End of Part 2

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“Hey, watch who you’re calling ‘normal’, buddy!”

Thank you, for showing the normalcy of how a T person feels about themself.