Rudy
It was Fall 1963, and my second-grade teacher, Mrs. Pritchard, was trying to conduct class. The impediment was me; I was being my usual class-clown self. In other words, I was a distraction, yet again.

“Rudy! Come up here at once!”

Uh oh. The smile wiped off my face, I shuffled to my feet and made my way to her desk to get my punishment.

She reached into the drawer and pulled out a bit of heavy white paper, cut it with her scissors and started folding it. It started to look like a miniature bow-tie, about two inches wide. She rolled some tape, stuck it on one side, and then, motioning me closer, she stuck it on my head. I was practically in shock. She was putting… a bow on my hair?? I was mortified.

“Go back to your seat. Boys who giggle like girls will be treated like girls.”

I think that must have been the day I learned how to blush. My face was burning and I felt like a giant spotlight was focused on me as I sat down at my desk. I didn’t look to the side to see who was watching, and I sunk down as low as I could in my seat, but I really wanted to put my head down and close my eyes until class was over.

I was as quiet as a stone for the hour until recess. Going outside with this thing on my head?? Last thing in the world I wanted to do. Unfortunately I hadn’t worn a hat to school that day, under which I might have been able to hide it.

Instead of going outside with the rest of my class I hung back at the door while they trooped through, then looked out the window at them all having fun. I could not face the prospect of being outside with a bow on my head. The option of keeping my hand over it the whole time was too ridiculous to consider. The whole thing was too humiliating.

When recess was over and they all came back in I hid in the corner until I could join the end of the procession.

When we were allowed to leave for lunch, Mrs. Pritchard called me over and removed the offending item from my head.

“The next time you feel like disrupting class I’ll bring a dress for you to wear,” she threatened. My eyes widened as I felt the fear of the possible ultimate humiliation.

“Yes, Mrs. Pritchard.”

I walked home slowly, vowing never to act up in class again.

-o0o-

Of course the vow didn’t last more than a few weeks. I couldn’t resist my own nature: to try and make my fellow students laugh. I saw Mrs. Pritchard looking at me, and stopped what I was doing, but for some reason she didn’t say anything.

However, the next day—the day which was burned into my memory—after we had all returned from lunch, she called me up to her desk. She ushered me into the cloakroom and held up a red and white dress!

“This afternoon you will be wearing this dress, Ruby,” she announced to me.

My mouth went dry, and if my feet had allowed it, I would have run as fast and as far as I was able.

“I, I, I’m Rudy,” I croaked out.

“This afternoon your name will be Ruby,” she told me. “Rudy is no name for a giggling girl. Take off your shirt.”

In a dreamlike way I unbuttoned my shirt and took it off.”

She instructed me to put my arms up and lowered the dress onto me. It had little puff sleeves with white cuffs, a white rounded collar, and a white line around the waist. It also had a built-in petticoat, to make it pouf out. She zipped it up the back. It tightened around me and I felt like I was being zipped into something like an Iron Maiden… except that the fabric felt kind of good. But that barely registered. It was a girl’s dress! No boy should ever put on a dress!

“Take off your shoes and socks, and then reach up and take off your pants,” she ordered.

I did, and then I was just standing there, in the cloakroom, in a dress and bare feet.

“I’ve brought these shoes and socks for you. Put them on,” she said.

They were little white socks that came a few inches over my ankles, with a bit of lace at the top. The shoes were, naturally, Mary Janes.

Lastly she produced a brown-haired wig and put it on my crewcutted head.

“All right, Ruby, we’re going back into the classroom.”

I looked at her pleadingly. “Please don’t make me go in there in front of everyone, Mrs. Pritchard. Please!”

“I’m sorry, Ruby, but I warned you what would happen if you kept disrupting my class.”

She ushered me ahead of her as we walked out of the cloakroom. The entire class had their eyes on me, and I instantly looked at the floor, hoping a deep hole for me to fall into would magically appear. Everyone started to laugh, but Mrs. Pritchard put a stop to that.

“Silence, class! This is Ruby. There will be no laughing at her or teasing her today. I have more dresses available, boys, and I might have a few surprises for you girls as well. Do I make myself clear?”

Twenty four heads nodded yes.

“Take your seat, Ruby.”

I was about to flop into my seat when I saw Jane, who sat next to me, motion to sweep the skirt, so I wouldn’t have my bare skin on the seat. Wild-eyed, I did as she suggested. It was hard for me to concentrate on my school work, as I was too aware of what I was wearing, as well as the sideways looks everyone else was giving me. Not only that, the wig brushed my face where I wasn’t used to having any hair. It was all very distracting.

When recess time came I really didn’t want to go outside. I went to Mrs. Pritchard’s desk to ask if I could stay inside.

“Ruby, this is a punishment. You will go out with the others, and I will watch through the window to make sure you’re out there.”

She went in to the cloakroom and brought out a girl’s jacket, which she helped me into. Then she sent me outside.

I walked slowly, dreading the inevitable confrontations.

Outside, several of the girls in my class surrounded me.

“Well, Ruby, how do you like your dress? Did she make you wear panties? I always thought you were too pretty to be a boy.”

I didn’t say anything. I was numb with fear and mortification, just focusing on the ground as they pestered me with questions and comments. The boys stayed far away; this was just too odd for them. They didn’t want to catch whatever it was I had. I saw my friend, Brian, look over at me and just shake his head. Eventually, tired of my silence, most of the girls drifted away.

“Sorry, Rudy, but you do look nice.”

I looked up and saw it was Jane.

“Thank you, Jane, but I’m dying of embarrassment.”

She took my hand and led me to a corner of the playground away from everyone else. We sat down on a bench.

“You should try not to let it bother you. They’re just clothes.”

“But, but, they’re girls’ clothes, Jane! Boys shouldn’t wear them!”

“She didn’t give you a choice, Rudy. You may as well enjoy it. Girls clothes are funner than boy clothes. You can wear all sorts of different colors, dresses, skirts, all kinds of combinations. And they’re softer too!”

“I, um…” I said. Inwardly I agreed that the fabric was softer, and even more inwardly I agreed that the skirt felt kind of nice against my bare legs. But as an eight-year-old boy there was no way I could admit that to anyone.

There was silence for a minute.

“You want to play on the swings?” she asked.

“Oh, okay, I guess.”

We walked over to the swings. Hardly any of the others were using them. We sat next to each other and started to swing. I noticed it made my skirt billow up a little, so I backed off and swung less enthusiastically.

-o0o-

Once back inside, I was able to relax just a tiny bit more. Although I didn’t like being in a dress I did have to admit, as Jane had said, that it was “funner” than my boy clothes. I could feel how different it was in the odd places it felt tighter. Mrs. Pritchard said Ruby whenever she called on me. I really didn’t like it, but somehow I got through the rest of the day. She helped me change back to my own clothes when school was over, and everyone else had gone. I was so relieved to be looking like a boy again.

“I hope you have learned something from this, Rudy. I don’t want you disrupting the class again, or I’ll find something frillier for you to wear.”

“Y-Yes, Mrs. Pritchard.” This dress had been bad enough!

-o0o-

By the time I got home, somehow mom had heard about what happened.

“So, a little birdie told me you spent the afternoon as a girl.”

“How… how did you know?”

“Mothers have ways of finding these things out. How did you like it?”

“What?! I didn’t like it at all!”

“But I understand it did make you behave. Maybe I should find you a dress or two for home. I’m sure Susie has a few old dresses that would fit you,” she said, referring to my sister, who was two years older.

I looked at her in disbelief. She had a little twinkle in her eye, so I really hoped that was a joke.

“I’m sorry I didn’t get to see what you looked like all dolled up,” she said.

“Mom, I was dying of embarrassment just being seen by everyone at school! Everyone is going to be talking about me!”

“Oh, don’t be so melodramatic.”

“What does mello drumadic mean?”

“It means it isn’t as bad as you probably think.”

I sincerely doubted that.

-o0o-

I thought of myself as a pretty normal boy. But what was weird was that as the days progressed I found myself looking at the way the girls at school were dressed. Suddenly, for no reason I could think of, I was interested in their clothes. Wondering what it would feel like to wear this skirt or that dress or even that blouse. I started to think I was going crazy. Mrs. Pritchard had to yell at me a few times to get my attention.

But what was even worse was that at home I looked in Susie’s closet more than once, to see what sort of clothes she had, and even felt the fabric on some of them, especially the shiny ones. It made me feel very guilty. I shouldn’t be in her room, and I definitely shouldn’t be looking at her clothes. It was as if Mrs. Pritchard had lit a fire in me that I was unable to put out. I didn’t like it; I wanted to be back to normal.

At school, for a few weeks, both boys and girls teased me about having worn a dress. In a way I kind of hoped some other boy in my class would misbehave and be forced to go through the same thing. Then at least I wouldn’t be alone in my misery. Even my friend Brian seemed to treat me differently, as if having worn a dress had changed me inside, or given me cooties. The result of all this was that I was unable to forget about the episode and put it behind me.

-o0o-

I was pretty well behaved through the rest of elementary school, and people gradually seemed to forget about “the boy who wore a dress.” I didn’t, although I really wanted to. My demeanor was a lot more serious, taking a lot of the fun out of my natural tendency to clown. There were no more reprimands from teachers.

At age fourteen I was still shorter than most of the boys, and some of the girls who had already had their growth spurts. Some guys were already thinking about dating and they were actually finding dates. These were generally the guys who were already growing sideburns and shaving… unlike me. I wasn’t sure how I felt about actually dating girls, but I was starting to like them, and to admire their bodies.

Jane, who was still a classmate, apparently already knew how she felt about boys. We were friends in a very casual way, but one day, out of the blue, she asked if I was interested in going to the art museum. There was a movie being shown there, aimed at teens, that she was interested in. It sounded okay to me.

“I guess so,” I said. “How much is it?”

“It’s free.”

“Oh! Well then, sure!”

Her mother drove, picked me up from my house and we had a nice time together. Both our moms had given us a little money to grab something to eat at the museum’s café. Jane and I found a lot to talk about, and I decided I liked her more than I had before. It was my first time out with a girl, and it went better than I thought it might.

-o0o-

I didn’t think much more about this. I hadn’t considered it a “date,” as such. Probably I was really clueless, especially since gallons of testosterone were not yet washing through my body. If Jane was expecting me to suddenly start being interested in dating her, she didn’t show it. But she did start to invite me to other events, as well as to just hang out. I was getting to really like her, and thoughts about kissing her would sometimes pass through my mind.

One day she asked me over to her house to hang out on a Saturday. It wasn’t that far, so I walked over. She met me at the door in a nice skirt and blouse. That surprised me a little, since it seemed a bit dressy for a Saturday.

“Hi Rudy! Come on in.”

“Hi Jane. Thanks. You look nice.”

“Oh, thank you. I wanted to look good for you.”

I wasn’t sure how to respond to that, so I just smiled.

We went into the kitchen and had drinks. There seemed to be no one else home. At my house it seemed like there were always people home.

“Where’s your mom?”

“She and my dad spend Saturdays at the country club, but I don’t always feel like going.”

I nodded. I wasn’t exactly sure what a country club was, or what people did there. I pictured a little wooden clubhouse out in the country, maybe a little bigger than the kind they had on The Little Rascals,* if adults were going to be going inside.

“Come on up to my room,” she said, starting up the stairs. At fourteen I was unaware that boys and girls weren’t supposed to be in either one’s bedroom, at least, not with the door shut, so I was happy to follow her up.

We entered a fairly girly room. The walls were pastel colors. She had a desk and chair, in addition to her bed and dresser and a big mirror. It was comfortable and neat, with some stuffed animals and a bedspread with birds all over it. We both sat down on her bed.

“Do you like my room?”

“Yeah, I do. It seems clean and comfortable.”

“Thanks. I couldn’t live in a room that’s messy all the time.”

“Oh. Um, me neither,” I agreed. My room wasn’t a pigsty, but it was nowhere near as clean as this.

After some talk about our classes, she suddenly changed the subject.

“Hey Rudy, do you remember when Mrs. Pritchard made you wear a dress?”

Did she have to bring that up?!

“Um, yes, I do. Why?”

“I just thought you looked really cute that day. You seemed so lost.”

“That was terrible, her letting everyone see me like that. I should have been really angry. Kids teased me about it for weeks.”

“But it did get you to behave, didn’t it?”

“Yeah, it sure did! I was afraid to even squirm at my desk.”

She moved a little closer to me on the bed.

“Was there…anything at all you liked about it?”

I began to fidget and blush, as I tried to think of what to say.

“Uh, well, I remember you telling me that girl clothes were more fun, and by the end of the day I kind of thought you were right.”

She stared me right in the eyes, until I looked away.

“How would you feel about wearing some girl’s clothes again?”

My eyes widened at this. I had never quite lost the desire to try on a dress again, but I had squished it way down so it couldn’t keep popping its head up.

“I…I…really don’t know. I’m not sure it’s a good idea.”

“Hmm. Well, how about this: you wear a dress and then we can make out a little?”

Talk about sweetening the pot! I have to admit that the thought of kissing Jane sounded really good to me. The dress part seemed really weird though.

I smiled. “That making out part sounds pretty nice, actually.”

She clapped her hands together and smiled too.

“That’s wonderful! I have something in mind for you,” she said, going to her closet.

I wasn’t at all sure I was doing the right thing, but she was so excited, and I did look forward to making out with her, although I wasn’t completely sure what that entailed. She finally pulled out a dress that looked like it was to be worn at a kind of formal event, which I thought would look really nice… on her. It was a green floral print dress with four frilly white lace trim things running down the front to the waist, a frilly lace collar, puff sleeves and a very full skirt. I’m not sure it was possible for her to have picked anything more girly than that.

“I used to wear this to church a year or two ago,” she said, smiling.

“Take off your clothes, Rudy.”

Oh. Yeah, taking off the clothes. This was embarrassing. I was soon in my underwear, displaying my hairless body.

“You’re not hairy; that’s nice! Take off your shoes and socks too.”

After I did so she approached me holding a bra! I backed up a little.

“What’s the matter? It’s just a bra. A dress won’t look right without something to fill out the front,” she said, reasonably. “Come on, turn around.”

I did so, thinking this was definitely starting to look like a big mistake on my part. And yet… I said nothing. She got behind me and pulled the straps along my arms, fastening it in the back. I shivered a little bit, feeling her fingers on my bare back. She quickly plopped something into each cup, so that I had little breasts. I started to peer down at them, but before I could get a good look, she asked me to put my arms up and a full slip slid down my body, followed by the dress, which she quickly zipped up.

This seemed nothing at all like my experience in second grade. Where that was merely horrifyingly embarrassing, this was embarrassing and… it was exciting me somewhat.

Grabbing my shoulders she turned me towards her and took a critical look at me. It being 1970, my hair was a lot longer than when I was a kid, and she took her brush and changed things around until she was satisfied, then added a barrette. Having gone through her growth spurt, Jane was a half a head taller than me, and in addition had two-inch heels on. She had on a big smile and looked down at me. I felt very small, standing there barefoot in a very girly dress in front of her. She walked me over to her full-length mirror and stood behind me. Next to her I looked like a little girl. In fact I was extremely surprised I looked like a girl at all.

“I think you look very pretty, Rudy, or should I call you Ruby for now?”

“I, um, I never did like her calling me Ruby.”

“Well, we’ll have to call you some girl’s name, or I’ll never be able to get in the mood we’re after,” she said.

Huh? What did she mean by that??

“Let’s see…how about… Ruth?”

“I don’t really feel like a Ruth, Jane. Pick a different letter.”

“Okay, we’ll go with a J, like my name, and you can be Jenny! How’s that?”

“Uh, sure, fine.”

“Okay, Jenny. I’m going to kiss you now,” she said, stepping up right next to me.

Ever so slowly she gently took my cheeks in her hands, slowly leaned over and softly kissed me.

Until that moment I didn’t realize just how much I wanted to kiss Jane. The desire hit me like a sledgehammer, and I wrapped my arms around her waist, turned my head up and urgently found her lips. This kiss was a lot more intense. She wrapped her arms around me and we were holding each other very tightly. The kiss lasted and lasted, and, flicking my lips apart with her tongue, she introduced me to French kissing. If I had been told about it before it happened, I think I would have been grossed out, but this way of showing me almost made me swoon with delight.

When we finally broke the kiss, she looked down at me.

“That was wonderful, Jenny.”

I was almost speechless. “Oh yeah!” was all that came out.

“Care to sit down on the bed?” she asked.

“I’d love to, Jane,” I said, acting just a little girly for her.

We then launched into the promised make-out session, which was way beyond any expectations I might have had, if I had had the chance to build up expectations. We felt each other all over. She petted my fake breasts, and allowed me to caress her real ones. I hadn’t thought too much about breasts until then, but my hand really liked stroking her breast, even through her blouse. It was such a nice rounded shape and felt…just…so nice. She seemed to enjoy my touch, which made me happy.

We must’ve spent an hour kissing and caressing. Our lips were both chapped red. Then we sat there next to each other holding hands and just talked.

It wasn’t until it was about time for me to leave that I remembered what I was wearing, and I was kind of flabbergasted at that. The fact that I could forget I had a dress on (and breasts) could hardly register itself in my brain.

Jane unzipped me and I changed back into my clothes, and brushed my hair back the way it usually was. We smiled at each other dreamily and gave each other a kiss before I left. I walked on air the whole way home.

-o0o-

Of course Mom noticed I seemed happy when I arrived home. When she asked me why, I thought about it a minute.

“I think I have a girlfriend.”

“Why don’t you know?”

“We, um, didn’t actually say anything about it. We just had a good time.”

-o0o-

Jane
Even in second grade I liked Rudy. He made me laugh with the funny faces he made and just the way he clowned around. I felt bad for him the day that Mrs. Pritchard put him in a dress, but I really liked the way he looked – so cute! I decided to be his friend that day, even as other people didn’t want to come near him.

We went to the same junior high school and had a few classes together. Like many other girls, I went through puberty earlier and got taller than a lot of the boys. Rudy stayed short, and it was obvious he wasn’t shaving. We were friendly to each other, but he didn’t seem interested in being more than that. When I talked to my mother about it, she just said that boys develop slower than girls, and some really took a long time to notice us!

There were other boys who were interested in me, but I wasn’t sure exactly how much I liked boys. I kept hoping that Rudy would ask me out. I could never get the image of him in a dress out of my head, so I never thought of him as a typical boy. By fourteen I was kind of tired of waiting, so I asked him out, to a movie, and we had a good time together.

I’m not sure what possessed me, but I really wanted to see him in a dress again. Now he had much longer hair, and it hid some of his face. I thought if I could get him into a dress he’d look just like a girl. That thought excited me, although I couldn’t say why. I asked him out to do other things, like go to the mall, and to hang out and he always seemed willing to go with me. But all the time I was wondering how I could get him to willingly put on a dress.

Ultimately it came to me: just offer to make out with him! All boys liked that, right?

When we were alone at my house one day, and I made the offer of making out, he went for it right away! And once I had him dressed up he did look like a cute little girl. I named him Jenny, and I could hardly wait to start the kissing.

I gave him a preliminary kiss, and I could tell he really liked it. He grabbed me and we had a really long, wonderful kiss that left us both breathless. I invited him to sit on the bed, and I really enjoyed how he replied in a kind of girly way.

Needless to say the make-out session exceeded my expectations. Making out with a girl who was really a boy got me very excited. I even let him feel my breasts, which I hadn’t been planning on initially. I kind of hoped Rudy wouldn’t get any bigger or hairier. I wanted him to stay as my little girlfriend.

I kept wondering why I wanted this, but I didn’t get any answers, and it was hardly the kind of thing I could discuss with other girls. I didn’t feel bad about it, because he really seemed to like it too. I mean, I wasn’t really forcing him to get dressed up.

-o0o-

Rudy
That night as I lay in bed many thoughts competed for attention in my head. I had let myself be dressed up like a girl in order to make out with Jane. What did that say about me? I mean, I really, really enjoyed the making out, and yes, I had forgotten about the clothes in the sheer enjoyment of being with her. But…did it make me a sissy? I didn’t feel like I was a sissy. The dress was fun to wear, and the whole feeling of those clothes was just so different for a while. About the only thing I knew for sure was that if she asked me to do it again, I would.

I wondered why Jane wanted me in a dress. Aren’t girls supposed to like boys? But then, I was still a boy, even if I hadn’t looked like one. It all became too hard to understand, and I fell into a confused slumber.

-o0o-

Sunday afternoon Jane called me and asked if I wanted to go for a walk to the park. I told her sure, and we met halfway between our houses. She took my hand and we walked in silence for a while.

“Jane, are we girlfriend and boyfriend now?”

“After yesterday I would say so!” she said enthusiastically. “But… I would also like you to be my girlfriend.”

That startled me. I mean, at some level it was obvious that was what she wanted, but my brain hadn’t made it to that level yet.

“Um, I’m not sure I understand how that would work.”

“Well, it would mean that we’d go steady like a girl and boy, but when my parents aren’t home, you’d come over and be my cute little girlfriend.”

Huh! That didn’t actually sound too bad, as long as it was just us two. And especially if there was a lot of kissing involved.

We entered the park and headed for a shaded picnic table. There was almost no one else in the park.

We sat down together and she turned to give me a gentle kiss, which brought a big smile to my face.

-o0o-

It has now been six years since I last saw Jane. Our last year of high school we had a fight over something stupid—I don’t even remember what it was—and she broke up with me, which I found really devastating. But the preceding four years had been very pleasant. We went on dates, but I’d go over to her house whenever she was alone—usually a Saturday—she’d get me dressed up, and I would be her little girlfriend. I actually came to enjoy this. Wearing the clothes was fun. For variety she started to put makeup on me too, and then to kind of teach me how to act like a girl. We still had our make-out sessions, and both of us really enjoyed them. I wasn’t sure, though, but by our senior year I felt that maybe she had decided she might be a lesbian, which, for her, may have caused some conflicting feelings about my male anatomy. I don’t know, and we never discussed it.

I still wasn’t sure what I was, other than a normal guy who liked wearing girls clothes now and then. By some miracle we had been able to successfully hide our activities from both sets of parents. They accepted that we were going steady, and I think my parents, at least, were a little sad that we had broken up.

Within two years after the dressing with Jane started I had grown a bit, but was still a couple inches shorter than she was, so I could still wear her clothes when we had our sessions. My looks did not sharpen into manly chiseled features, but I grew several whiskers.

Now I had an office job and was living on my own in a new city. My job didn’t take advantage of my English degree, but it paid well enough for me to have my own, decent, apartment.

On my own now, and alone most of the time, I started to feel the urge to collect a small female wardrobe—mainly older fashions—from thrift stores. I wasn’t sure where this desire came from, but I didn’t see any harm in indulging it. As time passed I also amassed my own collection of makeup. I’d get home from work sometimes and change, or spend the weekend en femme, but I still had no intention of going outside dressed up.

What I really wanted was to find another Jane, because, to be honest, I was lonely. There were just a couple people at work I was friendly with, but not invite-them-to-my-house friendly. I just wasn’t enough of an extrovert to go out and make new friends. Jane, who had become a real take-charge person, had always made me feel good, and I had really fallen in love with her within six months of us starting to go steady. I still had very fond feelings for her, in spite of the way she broke up with me.

-o0o-

My sister, Susie, wrote me to say she was going to be in town for a business meeting, and could she stay overnight with me. Since we always had gotten along fairly well, I wrote back, including a key, and said sure, she was always welcome.

It was only about an hour away, so she chose to drive, and arrived at my place before I got home from work. Since she had the key, she had already settled in. We greeted each other with a hug, and then went out to dinner, my treat.

Once back at my place we sat down to chat some more.

“Are you mostly alone here, Rudy?”

“Yeah, you know I’m not all that social.”

“Are you telling me that you haven’t even dated?”

“Hey, I’ve tried to date,” I said, defensively. “They just never seem interested.”

“Have you even had a date since you and Jane broke up?”

I winced. Did she have to ask about Jane?

“No, Susie, I have not,” I said, through gritted teeth.

“What happened between you two, anyway? I saw the way you looked at each other.”

“There was an argument; I can’t even remember what it was about, Susie. It was a long time ago. I know it was about something stupid though.” I had no intention of telling Susie of my suspicions about Jane’s sexual preferences.

There was a minute or so of silence.

“So… Rudy. How long have you been a cross-dresser?”

I must have mis-heard. There is no way on God’s green earth Susie could know about that.

“Excuse me?”

“You heard me. I saw all those female clothes in your closet. I’m not judging you, just curious.”

Oh. My. God.

“Susie, I… I don’t know what makes you think you have the right to root around in my closet, but this subject is, A, none of your business, and B, not up for discussion.”

“Don’t get angry, Rudy. I have no problem with it. I think I would have liked to know I had a little sister as well as a little brother. I was in there looking for a clothes brush.”

I was upset. As far as I knew, Jane and I were the only people on earth who knew about this. Now an uninvited guest had barged into the private room. And… a CLOTHES brush?? Do I even own a clothes brush?! Why would I keep it in my closet? I closed my eyes and tried to calm my breathing.

“Rudy,” she said softly. “I’m not going to tell anyone. Just talk to me.”

“What do you want?” I said, still keeping my eyes shut.

“I just want to know how you started and why. I think it’s interesting.”

I took a really deep breath, and opened my eyes, just looking into the distance.

“You may remember that my second-grade teacher punished me by making me wear a dress one day.”

I saw her nod out of my peripheral vision.

“Well Jane was the only one who was nice to me that day, and she thought it was cute. A few years later she asked me to dress up for her in exchange for a make-out session.”

Susie giggled at that. “I’m sorry. It just sounds kind of funny.”

“So anyway, it was Jane who got me started. We had a pretty good time with it, but we never left her house. After we broke up I never did it again until after I moved here. It makes me feel a little less lonely,” I said, looking down now.

Putting two and two together Susie said, “So, I get it. You are afraid to date, because your date might find out about this and dump you.”

This was not something I enjoyed hearing spoken of aloud, but she was right. I closed my eyes again and sat back on the couch.

Susie shifted over next to me and put her arm around my shoulders.

“You poor guy,” she said. “I’d hate to see you spend the rest of your life alone because of this. You’re a good guy. There has to be someone out there for you.”

“I’m not holding my breath, Susie.”

Soon after that we both got up and went to bed. The subject was not raised again while she stayed with me, thank goodness.

-o0o-

Jane
Rudy and I really enjoyed our little relationship, and I really enjoyed Jenny’s visits. There was just something about her… I fell in love with her. Well, I fell in love with Rudy too, but… she and I got along somewhat differently than I did with Rudy. It was hard to explain, but I felt warmer about her than about Rudy. She was softer, prettier (of course), and, I don’t know, just girlier. I’m not even sure Rudy was aware of how different Jenny was. I taught her about makeup and more about being a girl, and that was really fun.

But by the end of our senior year, I had started to feel that maybe I should be seeing a real girl. I wondered if I was missing out on something by seeing someone who didn’t have the same kind of brain and plumbing I did. We had learned something about gay and lesbian lifestyles in health class, and I was tending toward thinking I was a lesbian. I had my eyes on girls a lot at school. I didn’t really want to drop my girlfriend, Jenny, but I did want to start experimenting. There was no easy way to do this while we were going steady, and I really hated to break up such a nice relationship, but I went and picked a fight with Rudy about something small and trivial, and we ended up breaking up. I’m sorry to say I was very unpleasant to him.

During college I indulged my curiosity with several girls, and it was fun, all right, but it always seemed like there was something missing. One of them, Carol, even accused me of not really being a lesbian, which stung a bit.

By the time I graduated I wasn’t sure what I was. I knew I missed Rudy and Jenny, but I had kind of burnt that bridge, and wasn’t sure where or how I could find another boy/girl like that.

Now, two years later, I was living back in my old hometown, and working for my father’s chemical company. I was making a good salary and had my own place. I sometimes went to clubs and picked up girls, but they seldom lasted longer than one night. I even tried a couple real he-men, just as a test, and those experiences really turned me off.

-o0o-

One day I was really surprised to get a call from Susie, Rudy’s sister. We had been friendly until I broke up with Rudy, six years ago. She was already in college by then, so we had no occasion to see each other. Now she invited me to lunch, and I happily accepted. At the restaurant she asked me about myself and my job and social life. Then…

“Jane, tell me – what really happened between you and Rudy? You seemed like you were in love with each other.”

This was kind of out of the blue, but I didn’t mind telling her.

“This is going to sound bad, but I thought I was a lesbian, so I picked a fight with him in order to break up and start seeing other girls. I didn’t want to cheat on him, and I didn’t know how else to break up. Telling him, ‘I want to break up with you,’ would have hurt him too much, and he’d want to know why.”

“You said you thought you were a lesbian. Does that mean you’re not sure now?”

“It does. I don’t know if there’s an exact word for what I want.”

“I’m not real happy with the way you kind of used my brother,” Susie stated. “But I think he still carries a torch for you. He’s sad and lonely because he’s afraid anyone he dates will find out he’s a cross-dresser.”

My eyes opened wide at that. “How did you know about that?”

“We had a little talk recently.”

“I hope I didn’t cause this. I wouldn’t wish for Rudy to be lonely.”

“As much as I’d like to blame you, Jane, I understand that the urge to dress isn’t implanted by someone else. You probably did trigger it by getting him to do it, though.”

“I’m really sorry, Susie. I really did love both of him, but I just wasn’t sure about who I was. And I was not very nice to him when we broke up. I doubt he’d want to see me again.”

“I’m not so sure about that, but he does live an hour away, so even if he was interested, I don’t know how well a long-distance relationship would work.”

We talked more and she told me a little about his life and habits. I should have been surprised that he continued to cross-dress, but I wasn’t. At least to me, Jenny was a real person. You can’t just stop being someone… can you? It did sound like he led a lonely life. I remembered Rudy wasn’t really an extrovert at all, and I was sad to think of him sitting alone in his apartment all the time.

-o0o-

Rudy/Jenny
It was another weekend. I was all dressed and perfectly made up with no place to go. I had already tidied up my apartment and had started to think about making lunch, when someone knocked on my door. That was odd, unless it was a neighbor. You had to be buzzed in to the building, and frankly, I didn’t know any of my neighbors.

I had no intention of actually answering the door en femme, but I went to look through the peephole. To my utter astonishment, there stood Jane! My jaw dropped. Should I let her in? I stood there in indecision.

In a soft voice she said, “Let me in, Jenny. I want to see you.”

Jenny.…No one had called me that name in six years. In a daze I opened the door and we stared at each other. She looked great, in black slacks, and a pink blouse showing through her open jacket. She looked me over and smiled.

“You look wonderful,” she said.

“So…so do you.”

“May I come in?”

I stood aside and she walked in, glancing around the room.

My manners reasserted themselves and I offered her a seat. I sat down across from her, with my hands in my lap.

“How did you know it was me and not Rudy?”

“I heard your heels on the floor.”

A silence descended, and I sure wasn’t going to be the one to break it.

“I’ve missed you, Jenny. It’s a little late, but I want to apologize for how I ended our relationship. I was confused about what my desires were, and I didn’t want to try things behind your back.”

I nodded. “I suspected something like that.”

“You did??”

“I saw the way you looked at those other girls at school. I began to think you might be a lesbian.”

“I thought so too, but after I tried it, I still wasn’t satisfied. You are really the only person with whom I was completely happy, and I threw that away. I know I hurt you.”

I said nothing. What was she really here for?

“The fact is, Jenny, that your sister came to see me, because she’s worried about you. And since I’ve always regretted ending our relationship, I thought I’d come and see how you felt about me.”

I tilted my head and looked at her, thinking. How did I feel about her? She had really hurt me when we broke up, but I had eventually guessed why she did it. The real question was, do I trust her enough to try again? I remembered nights of crying into my pillow, and I didn’t relish the idea of that happening again.

She was starting to look sad, as I sat and thought.

“Jane, you did break my heart back in high school, but we are theoretically adults now, and should have learned a few things. We don’t really know each other anymore, and the Me you’re remembering is six years out of date. I’ve never stopped thinking of you, but I just don’t know how much I trust you.”

She gulped, and said, “Then I’ll just have to work at earning your trust again.”

“All right then. I’m game.”

“May I give you a hug?”

I stood up to receive it, and I have to admit it felt pretty darned good.

She smiled, then changed her tack.

“Jenny, do you ever go outside?”

“Never. I’d never pass, and I’d probably be too nervous.”

“Well, let me tell you, if I didn’t know you, there’s no way I would think you’re anything but a very attractive woman.”

That was pretty hard to believe. “Ummm, what are you suggesting?”

“I’m suggesting that I take you out to lunch somewhere. There has to be a nice restaurant in this town of yours.”

I blanched. The idea of going out in public was terrifying. It brought me some flashbacks of going on the playground in Second grade.

“I, I, I really don’t think I could do that, Jane.”

“Okay, Jenny. Hmmm. What do you think of this idea: we drive somewhere and just eat in the car?”

That was a little better, although it would still mean being seen by people.

“Jenny, just how many people in this city do you know?”

“Well, a few people I work with is all, really.”

“Anyone in this building? Have any of them met Rudy?”

“No, it usually seems deserted when I’m in the halls.”

“Well no wonder you’re lonely! So, no one knows you except for a few people at work, which means that no one could recognize you outside. Right?”

“Technically, yes.”

“Will you let me take you out, then? You look so fabulous it would be a shame to waste it all inside.”

I was pretty sure this would be the biggest mistake of my life, but I kind of sagged in defeat. At some level I really did want to go outside.

“Okay.”

“Oh, do you have a purse, or any jacket or coat?”

“Well, no, since I never planned on going anywhere.”

“Okay, the purse isn’t a big deal. Let me see Rudy’s jackets.”

I showed her to the front closet, and she looked it over. She pulled out one of my nondescript jackets and put it on. Handing her jacket to me, she grinned and said, “You wear mine, since it’s obviously a woman’s, and you were always girlier than I was anyway.”

Trembling a bit, I put it on and grabbed my keys. She ushered me out my door and out of the building to her car, where she opened the passenger door for me.

I directed her to a fast-food restaurant, and we went through the drive-thru. I then told her how to get to a nearby park. We parked and sat there, and were about to open our food wrappers.

“Jenny, there is no one, and I mean no one in this park. What if we sat at that picnic table to eat? It would be easier than eating in the car, and you’d be less likely to get anything on your nice dress.”

Against my better judgment I got out of the car, and we sat at the table and ate. She smiled at me a lot and I started to loosen up a bit. She told me about her college years, and what she’d been doing since then. Her personality, the one I had loved, started to shine through. She even told me about her experiments with girls and the two guys.

“But somehow they never measured up to you, Jenny. There was always something missing.”

My mind made itself up, and I reached across the table, smiled and grasped her hand. “That’s nice of you to say, Jane.”

“Does this mean you’re going to give me another chance?”

“Yes, but it brings up the whole problem of not living in the same city.”

“We’ll figure something out.”

When we were finished eating the park was still deserted. The picnic table was fairly secluded, so she sat next to me, put her arm around me and gently turned my chin to her and kissed me. It was a long kiss and reminded me of what I had been missing all these years.

“I really have missed you, Jenny. Your kisses are still just as sweet.”

That was very nice, but at the back of my mind I was wondering if she had missed Rudy too. She’d hardly mentioned his name once. Did she miss both of us or only Jenny?

We kissed some more, then got back in the car and came back to the safety of my apartment.

“Jane, I can’t help thinking that you haven’t said one word about Rudy. Do you even like Rudy?”

“I’m so sorry, Jenny. Yes, I always loved both of you, although I do admit Jenny always turned me on a bit more. Part of my evidently unbalanced bisexual nature, maybe.”

I wasn’t really sure how I felt about that. To me I was more Rudy than Jenny, who only appeared on weekends. If it turned out she was really happier with Jenny, I could foresee rough waters ahead.

We went to bed together. She did ask me to keep the bra on, and I figured I could do that for her. But I also determined that Rudy was going to make enough appearances for me to judge for myself if she really meant it about loving both of us. When I thought back to our school days, she did seem to have liked me either way. Yes, I guess I was aware that she seemed more excited when Jenny was around. Could I live with that?

If everything else balances out, I think probably I could!

The End

* The Little Rascals, also known as the Our Gang comedies, were short films made mostly in the 1930s by the Hal Roach Studios.

I had this teacher for second grade. (No, her name was not Pritchard.) She did put the stupid paper bow on me, and threatened me about the dress, but never carried through on that threat, which is good, because I think I might have had a heart attack and died right then and there. (Also, in my imagination, she was going to bring one of her own dresses, not one sized for a second-grader.)