Flat-Chested Jill

One day I just made up my mind on the spur of the moment and blurted out, "I want to do that." I stood up and turned around and sat back down on his dick, facing him this time. "I want to do that. I want to go topless on a beach."

Matt just looked at me, his mouth slightly agape, as if I'd caught him completely by surprise, and his expression brought back all my old insecurities. I was heart-broken, and I snapped at him. "You think it's stupid, don't you? Only girls with real boobs should go topless on a beach. That's what you're thinking, isn't it?"

His expression changed to puzzlement now, and he defended himself. "That's not what I was thinking at all."

"What then? What is that that look on your face?" I was pissed.

"I'm just surprised." He wrapped his arms tightly around my and hugged and held me close. "I'm so proud of you." His voice was hoarse, almost choking, and I briefly wondered if he might be crying. Then he pulled back a little, and said it again, "I'm so proud of you."

All my anger was gone now, and I loved him even more. There was no doubt he was sincere. Matt always knew the right thing to say. We kissed now, and one thing lead to another, and I had two orgasms that night, thinking about being topless on the beach, free and open, everybody looking at my boy-chest. Matt told me how beautiful I'd be, topless on the beach, and how much he wanted all the other swimmers to see my beautiful naked body, and he wanted me to feel the sun on my nipples and get an all-over tan and how he'd put lotion all over my body and carry me into the water to swim. I wanted to do that. I really did.

As we were lying in bed, all cuddled up, recovering from the exertion, I asked him, "When are we going to do it?"

I think he had dozed off because he startled awake. "Do what?"

"Go topless on the beach."

He was awake now, and he thought for a long time. "I don't know, Jill. There aren't any topless beaches anywhere near here. This isn't Europe and we're 500 miles from an ocean. How are going to do this?"

I had an idea, but didn't say anything. I wasn't sure I had the nerve, and I wasn't sure it would work.

The next night, we rented Blame it on Rio, and that night while I slept, I dreamt about being topless in public. I was walking down the street—the same street I walked every day to go to work. People I knew passed and instead of saying, "Have a nice day," they said "Nice chest Jill" or "Cute nipples Jill." I went into the Deli topless and the manager told me, completely serious, to "be careful not to get milk in the sandwiches." She took a paper towel and wiped a drop of milk from my nipple.

When I woke up, I was soaking wet between my legs.

Over the next days, Matt and I puzzled over the question of how I could go topless on a beach. We fantasized about jetting off to Europe and bathing on the Riviera, but there was no way we could come up with that kind of money. We found out about some nude beaches in America, and some places where kids go topless on spring break, but those were nowhere near us. We looked at the photos on the Internet and thought about what it would be like to have my nipples on display, warm in the sun, people all around, with Matt spreading lotion on them, but neither one of us could figure out a way to do it. I still had that germ of an idea that I wasn't sure would work, but I didn't say anything.

A few days went by and I didn't see Matt except at the deli. I had a day off from work on Thursday, so we arranged that he'd come over after his morning class, about 11:00. I told him I had a surprise for him.

When I heard his car drive up, instead of coming down to open the door, I shouted out the window for him to come on in and come up to my bedroom for a big surprise. I gave him a big smile and a naughty wink. I don't know what he was expecting. Maybe he thought I'd be wrapped in Saran Wrap or something. Remember Kathy Bates wrapped in Saran Wrap for her husband in Fried Green Tomatoes? But I had something even better in mind.

He opened my bedroom door and he stopped dead in his tracks, his jaw hanging down two inches at least. He was speechless.

"What do you think?" I asked, casually, coolly, as if nothing was unusual.

He didn't speak, just closed his jaw a little, almost back to normal, and came toward me. He looked me up and down, without touching, studying me from all angles. I had cut my hair a little and was wearing it in a pony-tail, kind of like my brother's. I'd cleaned the nail polish off my fingers and toes. I had no makeup and no jewelry. And all I was wearing was my brother's old swimming trunks that I'd swiped out of his room. Nothing but that.

Matt looked at me with a look that was no longer surprise, now more like admiration. He was impressed. It was a long time till he spoke, and I just stood there and smiled and let him look and think and look some more and think some more. Finally he spoke quietly and tentatively, "It might work." He looked some more, and reached out and stroked my nipples, then bent his head down and kissed one, and he patted my butt, through Jacob's swimming trunks, and he repeated, "It just might work."

He gave me a big smile and an even bigger hug. I took Matt by the hand into my brother's room, unzipped him and pulled down his pants and pushed him onto Jacob's messy bed with the sheets that hadn't been changed in at least a month. I threw Jacob's swimming trunks into a corner, got into the bed, and pulled Matt on top of me. We made a big wet spot on the sheets, but I didn't worry because I was sure it wasn't the only wet spot those sheets had seen. It would dry.

After we were done having sex, we stayed for a while in Jacob's messy bed talking and thinking, and we decided that we'd do it. I would go to the beach as Matt's little brother. His topless little brother. I'd pretend to be 13 years old. My name would be Joel. That's like Jill, just a little different. We'd have to plan it out and be careful, but it was possible. All we had to do was figure out the details. We could do it -- if I could work up the nerve.

That was a big if.

-- --

Matt and I had a lot of work to do to get ready. The location wasn't a problem. There was a popular lake about two hours away with a nice sandy beach. I'd been there as a kid and really liked it, but that was years ago and I was sure nobody there would know me. It was the perfect place.

Matt and I made a mental list of things we needed to work on so that I could pass as Matt's little brother. We decided that my face was no problem. With a little bit shorter hair, I looked an awful lot like Jacob. I was a little effeminate for a boy, but not much more so than Jacob, to tell you the truth. I had no beard stubble of course, but lots of 13-year old boys don't. I'd have to let my plucked eyebrows grow out, but that was easy.

My voice was incurable. It's high-pitched, even for a boy whose voice hasn't changed yet. I'd have to make sure not to talk where other people could hear. That wouldn't be easy for me—I love to talk -- but I could do it.

Then there was hair. Not the hair on my head, but body hair. I had no chest hair, of course, but neither did most 13-year olds. The problem was that boys don't shave their legs and armpits. It was an easy problem to fix, but it would take time to grow out. We figured it would be six weeks till I could show those parts of me as a boy. That would give us time to work on everything else that had to be done. My parents and friends would wonder what was going on, but I'd just tell them I was trying out the natural look.

My nails were long for a boy. I could trim those. I have a butterfly tattoo on my ankle and there was no way to get rid of that, but we experimented with a band-aid and were able to cover nearly all of it. Nobody would notice. I had tan-lines, both on my chest and my butt, where my two-piece bathing suit had covered me. Those would go away in a week or two if I stayed out of the sun.

No problems. As soon as the hair grew out, we could do it. I could be topless on a beach. I could be Joel.

Matt wasn't so convinced. "Jill, I don't mean to be insulting..."

I gave him a dirty look. "What?"

He hesitated, so I amplified the dirty look and he relented, hesitating. "You kind of -- well -- you act like a girl."

He said that like an insult, curling his lips on the word "girl," like it was disgusting, and, at first I grew angry. Then he smiled and we both giggled, and I taunted him, "So I'm gay. So what? Lots of boys are gay." I thought about all the sex we'd had, and the kissing, and the nipple sucking, and the orgasms riding on top of him, and him squirting in my mouth, and I decided that if I was going to be a boy, I wanted to be a gay one.

Matt shook his head. "You're not just gay, you're a flaming queer. Nobody is that gay." Then he imitated me, with a big smile on his face and my animated expressions, hands gesticulating as I talked, and I knew what he meant. He was right. Nobody is that gay.

So the project became a lot harder. It was comparatively easy to look like a 13-year-old boy. Much harder to act like one. This would take practice. I'd have to learn to walk and act like a teenage boy-- some vague combination of sullen and withdrawn and insecure and flirty and manly and physical and strong and aggressive and vulnerable.

So that's what we did. I spent weeks practicing to be Joel, working hard every day, sometimes with Matt and sometimes by myself. I studied Jacob and his friends and, when they weren't around, I tried to imitate them. I watched my face in the mirror as I talked, trying to keep my facial expressions calm and under control. I practiced drinking from a can of soda with my fingers firmly wrapped around the can, and for good measure, I crushed the can with my hand when I was done. I practiced sitting down in a chair firmly instead of daintily.

I told Matt I needed to learn how to hold a book in a more manly way, but Matt told me that if I really wanted to be a 13-year-old boy, I should not touch a book at all. He got me a copy of Car and Driver, and we practiced reading that, folding the pages around the back and holding the magazine scrunched up in one hand instead of two.

One of the hardest things to learn was how to walk without wiggling my hips. I didn't even know that I normally wiggled my hips. It wasn't intentional, but Matt says that watching me walk, with my hips wiggling, gives him an instant erection. Most of the time that's a good thing, but not when I want people to think I'm a boy.

Do you remember the scene in The Birdcage where Robin Williams is teaching Nathan Lane how to walk like a man instead of like a drag queen? If you haven't seen it, you should rent the movie, if nothing else, just to see Nathan Lane walking like John Wayne. Hilarious. That was what Matt and I did, with Matt teaching me how to walk like Joel. Matt even supplied the wisecracks just like Robin Williams had. The trick is to keep your feet a little separated, not to put one foot in front of the other, and to be careful how you swing your arms. Nathan Lane never accomplished it, but I did.

I spent a lot of time watching myself in the mirror, controlling my facial expressions, my hand movements, my eyebrows, my body posture. I carefully watched Jacob and his friends and, little by little, got to be more of a boy.

Eventually we decided that I was ready to go out in public. We would do something safe like walking down the street in normal clothes, not topless at the beach. That way, if I did something stupid or got caught, it wouldn't matter much -- I wouldn't get arrested. Also, the hair on my legs and under my arms wasn't quite ready yet, and I still had some bikini tan lines, but that wouldn't matter if I were wearing clothes. Walking down the street would be great practice.

We picked a location on the other side of town where nobody would know me, and I borrowed (stole) a pair of Jacob's jeans and a t-shirt. Matt thought it was best if I wore Jacob's underwear instead of my own so I did that, and I took his white socks and sneakers too. The sneakers were too big on me, but there was nothing I could do about that. We decided that when I was finished with it, I'd put the used underwear back in Jacob's drawer and see if he could tell by the scent that I'd wore them. That would be fun, but I wouldn't do that with the socks. That would be too cruel.

We worked on my hair, getting it just right, and sneaked out of the house undetected. I was nervous as a cat, but I don't know why. Even if I messed up and people realized I was a girl, it wouldn't matter, just walking down the street. I guess it was just stage fright.

There was really nothing to it. There were people around, but it wasn't crowded, and we just walked down the street. I remembered not to talk when there were people around. I kept my feet apart and didn't wiggle my butt. I slouched a little and moved my arms the right way.

My first real challenge was when we walked past a shoe store with a great selection of summer sandals in the window. There were people all around now so it was important that I not look-- and I didn't. Not even a glance. There was a jewelry store too, and I just ignored it. I was very proud of my self control. But when we were away from the crowd, Matt stopped and looked at me. "What are you doing?" he asked, with a big attitude in his voice.

I couldn't figure out what I'd done wrong and I was pissed at his tone. "What are you talking about? I didn't look. Not at the shoes, not at the jewelry. Nothing. What did I do?"

He looked disgusted. "I don't mean that. I mean you were smiling at everybody."

"I can't smile?"

"Have you ever seen a teenage boy smile at strangers?"

I thought about that one. Boys would sometimes smile at me, but I'm a cute girl. I guess a teenage boy wouldn't smile at mothers pushing baby strollers and certainly not at the babies. "I'm not allowed to smile?" I asked.

"No!" He was emphatic. "Maybe at a cute teenage girl if you want to flirt, but that's all."

He was right, of course. "What am I supposed to do? Sneer at them?"

He laughed. "If you're in the mood, you could do that. Probably better to just look away. Down is always good. Or at me. Not at jewelry though."

I vowed to do better, so we resumed walking. We passed a crowd of people and I didn't smile and didn't sneer. Not at the children, not at the couple eating ice cream, not at the old lady with her dog, and not at the priest. I was doing better. I even stopped to look in the window of a sporting goods store that had boxing gloves on display. Maybe that was over the top, but Matt didn't criticize.

When we had just passed the crowd, I was pushed to the side, hard, and I struggled to keep my balance. I looked over and saw that Matt had shoved my shoulder and was giving me a big smile. What the hell was he doing? "What was that?" I demanded.

"That was a hug."

"A hug? Are you out of your mind? You nearly knocked me over!"

"That's how boys hug," he explained. "Girls express friendship by hugging. Boys shove each other. That was a boy-hug. It means I like you."

I looked at him in disbelief. "A hug? That was a hug? What am I supposed to do? Hit you? Yell at you? Blow you a kiss?"

"No kisses. Just shove me back. That means you like me too."

"You're kidding?"

"Nope. Shove me back," he answered. "Go ahead. As hard as you can."

I thought for a moment, then gave him a shove on the shoulder. He wasn't impressed. "Act like you mean it," he said. "Don't you like me?"

I gave him a big shove this time, trying to knock him over. He laughed. "That's right." He thought for a moment then added, "By the way, this is a time you can smile." I shoved him again, even harder, and he shoved me again, and we smiled at each other, and I actually started to understand. We liked each other.

After the shoving lesson, we decided that I was ready for a more advanced challenge so we went to a pizza place. I grabbed a manly fistful of too many napkins and sat down ungracefully at a table, yanking the chair back from the table and dropping into it. Matt went to the counter and came back with two big slices and two cans of Coke. I watched how Matt ate the pizza, curling it up almost into a tube and taking big chomps out of the pointy end, and I copied him. I drank heartily from the soda can, holding it with strong fingers, but Matt didn't crush the can so I didn't either. I thought about John Travolta walking down the street eating two pizza slices at once, layered one on top of the other, at the beginning of Saturday Night Fever, but I couldn't tell Matt about that. There were people close by and I wasn't allowed to talk.

When we'd finished eating, we threw the paper plates into the garbage and threw the soda cans there too, even though there was a recycle bin right next to the trash barrel. We were real men. Then Matt looked at me with mischief in his eyes, and said, "I need to hit the head. You coming?"

I could only imagine the look on my face when he said that. Probably like the proverbial deer-in-the-headlights. I hesitated, not knowing what to do and not being allowed to talk. Matt started walking toward the restrooms and I couldn't be left behind by myself so I followed. We got to the restroom doors -- women to the left, men to the right, and I looked at Matt, not knowing what to do. He motioned for me to follow, so I turned right.

Fortunately, there was nobody else in the men's room. There was a smelly urinal, a toilet stall, a sink, and no tampon dispenser. I looked for a condom vending machine but there wasn't one. Matt went to the urinal and I did the obvious thing, entering the toilet stall. It was no different than the ones in the ladies' room -- maybe a little dirtier-- and I briefly felt at home. I peed and looked at the pornographic drawings some kid had scratched into the paint. It was a dick with hairy balls. That's something you don't see in the women's room.

I heard Matt flush and run the sink, and I flushed and came out to discover that there was another man at the urinal. I kept my cool, didn't look, and went to the sink, with Matt watching me, obviously trying hard to keep from laughing. Just as I was ready to turn on the water, my cell phone rang. I thought fast and realized that I wouldn't be allowed to talk, so I reached into my pocket and muted it, but I saw that the man at the urinal was giving me a strange look. I didn't know why. Am I supposed to turn off my phone before I go to the men's room? I washed my hands and tried to dry them with one of those air-dryers that never does anything useful. Matt seemed like he was in a hurry and was giving me subtle hand-signals, so I wiped my hands on Jacob's jeans and followed him out.

When we got out of the pizza place, Matt was disgusted again, not speaking, just giving me a dirty look. I gave him an even bigger dirty look back and he spoke first, "The love theme from Titanic?" he asked, incredulous.

Now I knew what I had done wrong. It was the ring tone on my cell phone that had given me away. That's why the man at the urinal had given me that look. I had just down-loaded it last night so Matt had never heard it. "Sorry," I mumbled, and I took the phone out of my pocket and powered it off. I looked up at Matt apologetically.

I had a lot to learn about being a boy.

-- --

There are some movies about women who try to pass themselves off as men and vice versa. I don't mean movies like Tootsie or Mrs. Doubtfire or Some Like It Hot or To Wong Foo or that Big Momma junk, with men dressing up in drag for laughs. I'm talking about movies where a woman is really trying to make people think she's a man. Maybe these movies could help me be a better Joel. Matt and I watched some of them, studying them for hints and clues.