I was raised as a boy. The first time I figured out something was wrong with that was when I was 5.
It was after a time I’d been out with my parents at the mall. During that trip, my father and I went into the public restroom together, but he stood at a urinal and I sat on a toilet in a stall, the only way I’d been taught. By that point I’d picked up that urinals were for peeing, but I didn’t understand how he could do it neatly. When I peed while sitting on the toilet, it splashed all over and I needed to wipe up. That evening, when I asked to be excused from dinner to go pee, he asked me if I’d ever learned to pee standing, and he offered to show me.
He peed first, and I saw his penis, a tubular organ that extended out from his body. Pee came out of the end of it. That was obviously the thing I was missing. I stepped completely out of my pants and underwear, not believing for a moment that I could do this without getting them all wet, and stood there and tried to do what he had done. My pee just came out from a little hole between two flaps of skin, which I tried to hold apart in a bad imitation of what I had just saw him do. It was closer to what he did than I had imagined I could do, getting most of the pee in the toilet, but I still got some on myself and on the floor.
He ignored the difference in our bodies, wiped the pee off the floor with some toilet paper, handed me more paper to wipe myself, and said, “Your penis is a lot smaller, but it will get as big as mine when you grow up. Just keep practicing that and you’ll learn to do it perfectly.”
I wasn’t sure whether to believe that. What I had didn’t look like a smaller version of what he had, but something entirely different. I don’t think I understood negative numbers yet at that age, but if I did, I would have said my penis was of negative length.
Nevertheless, I practiced. I tried different techniques. Rather than just hold myself open with two fingers, I found I got the best control by grabbing the widest part of the flaps that covered up my pee hole between my index fingers and thumbs. Using that technique, I figured out how to keep the stream from splashing on me from the first drop to the last, how to keep it going the farthest distance out from my body, and how to shake off the last drop. This eventually allowed me to pee at urinals through the fly in my pants and underwear without getting myself or my clothes wet.
When I was 7 and had mastered that technique, I had still seen no indication that I was growing a penis, but I overheard some boys talking about a girl’s private parts. One of them had seen the real thing, and was trying to describe it in as much detail as possible to the others. It sounded a lot like what I had. It was hard to find pictures, but I eventually found anatomical drawings labeling the parts, and confirmed I had every part listed in the female diagram visible from the outside, and lacked everything that was unique to the male diagram. So why did my parents think I was a boy? I was clearly a girl.
When I was 8, I talked to my parents about it. It didn’t go the way I hoped. Even when I pulled down my pants in front of them both to show them I had a girl’s parts, they didn’t see it. Instead, they thought I was transgender. Mom ended up having a long talk with me about what that meant, and they both tried to reassure me that being trans was OK. It wasn’t what I wanted, but some of the results were helpful. Mom bought me some girls’ clothes, and also helped me come up with Kelly as a girl form of my given name Kelvin.
All my friends accepted my request to be called Kelly and called me by it, but they seemed to ignore the part where I told them I was a girl. They ignored it when I wore skirts and dresses, too. I worried they were going to taunt me about being a sissy, as I had seen some other boys teased just because they were small, but they didn’t. The boys and girls both simply ignored any attempt I made at being recognized as a girl.
When I was dressed in girls’ clothes, I tried to use a women’s public restroom, and I was told by other women and girls that I couldn’t be in there because I was a boy. They completely ignored that I was wearing a skirt. That first time didn’t stop me, and I sometimes managed to use the women’s room when I got into a stall while there was nobody else there to tell me I couldn’t, but repeated rejections led to me no longer trying to use the women’s room and just using the men’s room. The men didn’t care, even when they saw me go in wearing a dress or other obviously feminine clothes and sit in a stall. They neither told me I couldn’t be there nor made any other remarks suggesting they saw me as a girl.
So as I got older, I stopped trying to be recognized as a girl at all. As I grew and needed more clothes, I just had my parents buy me boy clothes, and they seemed to forget the whole transgender thing as a “phase” I had gone through, though everyone still called me Kelly. After I figured out Kelly could be a boy’s name, too, I privately cursed that fact and wondered how it would have gone if I had decided I wanted to be called Melissa or something. Would that have made them recognize me as a girl? But I stuck with being a boy named Kelly.
After I got the birds and bees talk mainly from Dad, Mom took me aside and started giving me the talk about what happens to girls. She explained how to use tampons and pads and why. I thought for a moment she had figured out I was really a girl, and had been pretending not to know, for some reason. But then she told me, “If you really want to pass as a girl, once you get into middle school, always carry a tampon or pad in your purse.”
So she still didn’t think I was really a girl, but simply remembered when I was, in her view, transgender. She was simply giving me tips to pass better as a girl if I decided to do that again, because it was more complicated after these changes boys and girls were going through. And she was also making sure I would know things that a real girl of this age would know. None of that actually helped my situation, since the other kids didn’t even recognize me as a girl when I was trying to make it obvious.
Mom didn’t understand that I really did need to know about tampons and pads starting a year or so after that talk, nor did she ever explicitly give me any, but I took them from the obvious supply in the bathroom when I needed them. That part of what she described about girls happened to me exactly as she said. She never talked to me about the subject again after that one time, neither to reinforce the lesson nor to ask why her supply ran down each month twice as much as it used to. I wasn’t dressing as a girl at school at this point, but I carried tampons in my school bag, and changed them when needed in a stall in the boys’ room at school.
One thing that didn’t happen was breasts. I thought surely that as I proceeded through middle school I would start growing breasts as other girls were doing, and it would become more obvious that I was a girl. I had made up my mind that when my body unmistakably had a woman’s shape, that I would start wearing female clothing again, partly out of necessity, and believed people would have to recognize me as a girl then. But that didn’t happen. I guess there was a little growth there, but no more than the fat some boys develop in the chest. I saw boys in the locker rooms after gym class who had more there than I did.
What changed was down below. The boys now had larger penises, while I just had a tuft of hair hiding my mostly flat parts. In addition to that, I had some growth in my hips. My legs had become farther apart, and the lack of anything dangling between them should have been even more obvious when changing in the locker room. But not once did any of those boys comment on my appearance there, the way they sometimes teased other boys who developed more slowly, or who they were just bullying.
As this happened, boys jeans started fitting me less and less well. They had extra space in front for the dick and balls I didn’t have, and less in the hips where I needed it more. They weren’t stretchable enough to allow the extra in front to really make up for the extra I needed in the hips. Once I was having to buy jeans a waist size larger than my waist really was and cinch them down with a belt, one time I had the idea to try on a pair of girls’ jeans in a store and I found they fit much better.
After I explained to Mom that girls’ jeans fit me better, she explained to me the different varieties of sizes in adult women’s clothes, which were also an option for me at my size. This was the first I realized how complicated women’s clothing sizes were, but I came to understand it was mainly because women have more variety in shapes. Some women have hips much bigger than their waists, and some only a little bigger. So I had many more sizes to consider trying on than I had realized, and in the end, it allowed me to find clothes that fit me even better.
After that point, every pair of shorts or jeans I got came from the girls’ or women’s aisle, though I went through both different sizes and different size categories as I developed. But I didn’t buy girly-looking jeans with appliques or stuff like that, just plain ones in the shape I needed.
At first, I was still wearing boys’ briefs under them. I didn’t want to switch to panties because I liked having the fly so I could use urinals. As soon as I had gone back to boys’ clothes after that period of dressing as a girl, I had gone back to peeing that way. It had ceased to be a challenge for me, and was instead a convenience to be able to pee without pulling my pants and underwear down and sit and have to wipe up afterward.
It wasn’t until I was 14 that I discovered what one brand called men’s fashion briefs. Other brands had similar styles under other names. They were made of fabric more like panties, were thinner, and had more stretch to them. Unlike boys’ jeans, this stretchy fabric allowed the extra fabric in front to pull around to my hips and make them fit almost the same as styles of panties that covered the hips. And they had the convenience a fly.
At age 15, not seeing any breast development in sight, I decided to try wearing girls’ clothes again anyway. I was already wearing the jeans. Mom helped me with what were now really young women’s clothes, and other things. I got my first bra, an A cup. Mom showed me how to apply some basic makeup as well. And I decided I would let my hair grow out. I didn’t do much with it, but kept it at shoulder length. But my parents again just thought I was showing my transgender tendency.
With these clothes and lessons, I started once again going to school some days in full girls’ clothing and carrying a purse. The kids at school didn’t notice. I neither got teased for being a sissy boy nor treated as a girl. The girls told me I wasn’t welcome in their restroom. The boys never protested my presence, nor did they hit on me like boys sometimes did with other girls. So I continued wearing the fashion briefs under any clothes that would let me pee at urinals, including some skirts. I had panties to wear with anything else.
Not even in the boys’ locker room for gym class did any boy say anything when I was putting a dress into my locker or putting it on afterward. And yet, it wasn’t like I wasn’t there at all. They sometimes talked to me about things that had happened in class that day. There were even some guys who talked to me about how some other girl was hot as if they thought I’d be interested in her. But I wasn’t teased the way other boys were, nor did any of them come on to me. I was just one of the boys, as far as any of them were concerned.
Other girls were getting asked out on dates, but not me. I even, while wearing dresses, asked a couple guys out on dates. They all politely declined, just saying things like they “didn’t go that way.” After less than a year of this, I again gave up on the idea and just wore boys’ clothes, except girls’ jeans.
The comments from some boys about how certain girls were hot got me thinking. Why not? Eventually I got up the nerve to try asking a girl out on a date. I knew that was going to get weird if we ever got to the point of having sex, but at least I could have something, right? The first couple girls I asked told me they were steady with some other guy, and there were loads I knew I had no chance with, but Lisa, the third girl I asked, accepted.
So I got my first date outfit. A boy’s date outfit: a sport coat and matching slacks, a button-up shirt, and a tie. Fortunately, the slacks were loose enough that they didn’t cause a problem with my hips. The top was no issue, naturally, since I still barely had enough to fill my A-cup bras. There was no chance I needed a B.
The date went well, I guess. We had dinner and saw a movie and we kissed. And we made plans for a second date. I had to ask the question.
“Lisa, do you want to see me dressed like I was this time, or would you rather see me in a dress?”
“I wouldn’t mind seeing you in a dress sometime if that’s something you like, but I don’t want our date to get weird. Just dress normally.”
This was yet more confirmation about how the kids at school simply didn’t see it when I was wearing female clothing. I was worried Lisa wouldn’t even notice when I wore a dress to one of our dates. But per her request, I was still dressed as a boy for our second date. At least she told me I could wear a dress around her sometime. The second date went OK as well, and I got as far as touching her boobs, but she didn’t want me touching below the waist and didn’t try me there.
As we were finishing the date, after a pretty good kiss, I asked her, “Can we do this again next weekend?”
“No, Kelly, I’m acting in the school play next weekend. There are two performances, Friday and Saturday evening, so both nights are out.”
“Could we do something in the afternoon?”
“I have a soccer game Saturday, but Sunday is possible. Except I told the other girls I would go shopping with them in the morning and early afternoon.”
“Oh. Could I come shopping with you? I could wear a dress.”
“I guess that would be OK. The other girls have asked their boyfriends to come on these trips but none of them have come. You would be the first. And I guess it’s fine if you wear a dress then. You’d look like you fit in.”
“OK, girlfriend. I’ll be there,” I replied, emphasizing the word because of how she implied I was her boyfriend now. We’d had two dates. Was that enough?
So after breakfast the following Sunday morning I put on my best dress after a few months of not wearing girls’ clothes. I should point out it was simply the best dress I owned; I hadn’t gone all out on dresses, and only owned about a week’s worth of female clothes that fit me now. This was simply the best of three dresses among them, and the one I’d pick to go on a date if they were my only choices. I was going to be with my girlfriend, but also with some other girls. Did that count as a date? I treated it as such, and Mom seemed to as well, reminding me about how to apply makeup and touching up a couple blemishes on my face, and even styling my hair a little into a more feminine style. At 10, Mom dropped me off at Lisa’s house.
Lisa saw me and exclaimed, “Oh, Kelly, that dress looks really nice on you! Some people might not even realize you’re a guy! I’m not sure what I expected, but I didn’t expect you to look this good.”
That was totally not the reaction I had hoped for from her, but at least she did recognize that I had worn a dress, and she seemed to think I looked nice in it. Two out of three, I suppose, when the usual I got was zero out of three.
We didn’t have to wait long for the other girls to show up, which turned out to be just two other girls, Sabrina and Kayla, who arrived together since they lived next door to each other.
It was Sabrina who commented first, “Wow, nice dress, Kelly. I didn’t believe Lisa when she told me you were going to be wearing a dress on the trip with us.”
The same two out of three: She was giving me a compliment, and she actually saw that I was wearing a dress. It was clear that somehow she still thought of me as the male Kelly, though, despite me wearing clothing no ordinary guy would be caught dead in, but it was more than most people could see.
Kayla added, “Yeah. I like that we’re all wearing blue. Nobody planned that, right?”
Everybody denied having coordinated colors for this get-together, but Kayla was right that we were all wearing blue, even though we had four different dresses in different shades of blue.
When Lisa told me we’d be all walking to the mall, I am sure I gave her an awful look. She explained that one end of her street came right up to the mall, and that was why the girls all met here. That end was obviously not the end Mom drove through to bring me here, because I would have noticed. Pretty soon we left Lisa’s house and walked to the mall.
It was actually more of a walk through the mall parking lot than it was from her house to the edge of the mall property. I wished I’d been wearing sneakers, but at least my girl shoes were flats. Mom had advised me to get these shoes, black slip-ons with a strap across the instep that had virtually hidden elastic, if I only got one pair of girl shoes. Black went with anything, and I wasn’t going to have to relearn how to walk.
Sabrina had the highest with three-inch heels, but she was obviously practiced with them and only had difficulty on one irregular patch in the parking lot. And they matched her dress. That was a thing I picked up from Mom’s explanation that girls did with real date outfits. But this had been on short notice, and I hadn’t gone out and bought any new clothes for it.
The actual reason for the walk was probably not to avoid bothering Lisa’s mom to take us there and back, but for gossip. The girls chatted non-stop until we reached the door to the mall, mostly about other girls at the school and who they were dating, and other guys at the school they’d want to date if they could manage to pull them away from their current girlfriends. I felt a bit left out, but I was able to contribute one bit when the discussion became an actual dick-measuring contest.
“Hey Kelly, you have gym with Brad and Randy, right? Have you seen their dicks?”
“Well, I haven’t seen them erect, and I’m not looking at them on purpose, but I think Randy has the biggest dick, limp, out of all the guys in that class.”
And I wanted to add, “And I have the smallest,” but I didn’t say it.
Shopping was as I expected. We went into many stores but bought little, as we were all sophomores in high school with limited budgets. The girls tried on several dresses. Annoyingly, one time while I was waiting for one of them to get dressed, another woman objected to my presence in the women’s dressing room area. Even dressed the way I was, a stranger who hadn’t known me at all thought I was a boy!
“He can’t be here.”
But Sabrina defended me, “Kelly’s with us.”
I did note, though, that she didn’t say “She‘s with us.” Sabrina still thought of me as a boy.
We stopped for lunch at the food court, with our total purchases so far being a blouse for Lisa and a skirt for Sabrina. Then it was back to shopping. A couple stores later, Kayla was modeling a pink dress for us that we had all given her compliments for.
Kayla suggested, “Hey, if I wear this the next time we go shopping, can you all wear pink to match?”
Lisa and Sabrina said they could. But I responded, “Does that mean I’m being invited to another shopping trip with you?”
“Sure,” Kayla replied.
“Why not?” Sabrina said.
“You seem like you’ve enjoyed it, and I enjoyed having you with me, something that these girls’ boyfriends would never do,” Lisa added.
“OK, but I don’t have a pink dress.”
This resulted in the group deciding they needed to find me a suitable dress, so after Kayla paid for hers, the rest of the trip was devoted to that. Now I was the one going into dressing rooms and trying on dresses. Eventually we found one that everybody liked and thought looked good on me. It was when we went to pay for it that I realized my problem.
“Dad gave me forty bucks because he knew I was going shopping with you, and I have another fifteen in here, but this dress costs sixty. I’m going to be a little short. If only I hadn’t bought lunch...”
All three of the girls volunteered to pay what I was short. Ultimately, Lisa paid it, saying, “Kelly’s my boyfriend. I should be the one helping with this.” And Lisa actually gave me twenty, so that I could keep the other fifteen I had. I thanked her for not letting me go home broke.
We all walked back to Lisa’s house, with more gossip, and called for rides home. While we waited, Lisa went into her room and modeled for us the blouse she had bought together with a skirt she already owned that she thought went with it. We’d seen the blouse on her before, but it was with another skirt from the store that she had only tried on so she had something below the waist after taking off her dress. We all agreed it looked better this way than how she had worn it in the store.
I was now committed to going shopping with the group again, wearing the pink dress. Dad gave me money again, but during the second trip, the suggestion was made to wear green the next time we shopped, and I told them I did have a green dress, so I didn’t end up buying a dress. What they did suggest, though, was buying a padded bra. It was designed to make my A-cup breasts look like Bs.
“Your dresses have more space for breasts that you aren’t filling out,” Kayla commented.
“With this you’ll look even more like part of our group,” Sabrina suggested.
Privately, I hoped it would help strangers see me as a girl, but somehow I doubted it would work.
It was a while before we all got together again, with one or another of us traveling or otherwise unavailable, and the girls agreed to wait until we could all be together again before dressing in green. I went out with just Sabrina and Kayla once, all wearing more casual blouses and skirts in mixed colors, and we didn’t buy any clothes.
One good thing came out of that trip; Sabrina let slip that a store that sold sex toys (among other things) that was supposed to be restricted to age 18 and up didn’t actually check IDs. While I didn’t go there with them present, since they’d probably think I was buying something for Lisa and ask her about it later, the next time I was in the mall with Mom, dressed female, after giving an excuse of going to the restroom, I slipped in that store quickly and used the money I didn’t spend while out with Sabrina and Kayla to buy myself a vibrator. It seemed like I was never going to get an actual man, so at least I’d have that. I slipped it into my purse on the way back to Mom and she was none the wiser.
On a weekend that Sabrina was away, I finally had another date with Lisa. I guess my appearance during our shopping trips had made an impression on her, since she’d made a U-turn from “I don’t want our dates to get weird” to “Wear the blue dress you wore on our first shopping trip together.” The date went well, though she still shut me down when I tried getting intimate.
Lisa explained, “My family is sorta strict, religiously. They’re fine with you dressing as a boy or as a girl, but I can’t have sex until after I move out of their house. I can let you touch me down there, but only touching. No putting fingers in me, no excessive rubbing, and no removing my clothes any more than you need to to get a hand in there.”
So she let me touch her. While I had my hand there, I told her, “You’re welcome to do the same. My family has no such issues, though I understand if your religion limits you to touching me no more than I am doing with you.”
“OK, I guess,” she said, and worked one hand under my dress and into my panties.
“It doesn’t feel like I expected it would,” Lisa said with her hand still on my private parts.
“That’s because I’m actually a girl,” I told her.
“No, don’t be silly. This is your penis,” she said while running two fingers down the flat part of my vulva between the vaginal lips, stopping just short of my vagina, “And these are your balls, well, no, part of your ball sack. Your balls are tucked down under your dick,” she added, grasping the stretched-out tab on one side and then on the other, the places I grabbed while holding myself open to use a urinal.
As she pulled her hand out, she said, “They are smaller than I expected. I thought you’d be big and hard by now.”
It wasn’t worth trying to explain to her that I was a bit aroused. That was the only reason two fingers had fit between my vaginal lips without her having to pry them open. Since we weren’t going farther than this, I realized I was never going to convince her. I could have grabbed her hand and plunged her fingers into my vagina, and then maybe she would have been convinced, but that was also going to violate her religious limit, and probably result in us never dating again. So I had to let her continue believing I was a boy.
I halfway considered breaking up with her anyway. Maybe it would be easier to convince someone else I was a girl. I considered candidates. The other girls from our shopping trips were out. Though they talked about other guys and even compared them to their own boyfriends, it seemed that that was only talk and they weren’t actually considering dating other guys. The gossip had explained several other girls were firmly attached to certain guys as well. I got down to a short list of about half a dozen who I actually asked. Some said they wanted someone more manly, and the rest said that they didn’t want to cheat on their current boyfriends. Of course I wasn’t manly enough for them, since I wasn’t even a man, but absolutely nobody was accepting me as a woman, even when I dressed the part.
So I ended up sticking with Lisa through the rest of high school. We had a lot of dates, mostly with me dressed as a boy, but once in a while as a girl. She insisted that I dress as a boy for the school dances; she didn’t want to be seen as a lesbian by the others at school, even though it apparently didn’t violate her family’s religious code. She clearly didn’t realize how the entire rest of the student body, apart from our little clique, never noticed the female clothing I wore to school at least two days a week at this point.
And I went on a number of shopping trips with the three girls. I usually got one new article of clothing each trip. After about a year of these shopping trips once or twice a month, and some extra, more ordinary stuff I’d gotten on trips with Mom, I had enough girls’ clothing to dress as a girl all the time. For most of junior year and all of senior year of high school, I did so. And it was still the same way. My parents and the three girls recognized that I was dressed as a girl. Everybody else continued to ignore it.
Every Friday the girls sat together at lunch, rather than with their boyfriends or other friends, and once I was dressing as a girl, they invited me to join them in these get-togethers. Everybody else just thought I was there because I was Lisa’s boyfriend; that was public knowledge. I somehow managed to get one more girl to recognize that I was wearing girls’ clothing, though she also believed I was trans rather than a natural girl, but that was it, no matter how many people I told or how I tried to tell them. She joined our Friday group when the other girls approved of it and I invited her.
There was one other exception, an incident my senior year when I was out shopping with the girls. I dropped a dollar bill when I was putting my money away as I walked out of a store after buying something. A little boy who must have been about 5 saw it, and came running over, picked up the dollar, and yelled, “Hey lady, you dropped this!”
The boy’s parents followed quickly behind, reaching him just after I accepted the dollar from him. His mother scolded him, but not for running off or for talking to strangers. She said, “Timmy, that’s clearly a guy. You apologize for calling him a lady.”
“No, Mommy, she’s a lady.”
The boy’s father picked him up and said, “We’re sorry for bothering you, sir.” And the family quickly rushed away.
I would have given the little boy the dollar back for his honesty. After all, it was only a dollar. I didn’t have much, but I could afford that. But his parents were embarrassed over the fact that, in their eyes, he had called a guy a lady. The interesting thing was that the boy didn’t just see that I was wearing a dress, but actually identified me as female. I could easily have seen a little kid like that saying there was a guy in a dress, but that’s not what he did. Nobody else in all my 18 years of existence had recognized me as a woman, even at times like this I was trying to make it as plainly obvious as I could, and here some random 5-year-old does it.
The girls I was with all considered me trans at this point, and they didn’t notice what was special about that moment. I did, though, and I wished I could have spoken with the family and somehow found out how he recognized me as female, but they rushed off into the mall quickly, and I would never find them.
As senior year was coming to a close, I found out that Lisa was going off to some Catholic college. Since I was going to our state college, the best that I and my family could afford, we agreed to end our relationship after the senior prom with no hard feelings. I think she was a little disappointed, in part due to not getting the chance to have sex with me, but she would have been disappointed anyway since she was expecting to get my dick into her, a dick that didn’t exist. So it was probably kinder this way, I felt.