Flat-Chested Jill

My favorite sites had been the ones with naked men. Most of the sites with naked men are hard-core gay sites, which I didn't really like. You can call me a bigot if you want to, but I don't want to see two men kissing or sucking on each other. But there are soft-core gay sites that are good. Also, there are nudism sites that are mostly women but have some men too, but they're usually old and fat. And then there are sites where people post pictures of themselves. Those usually have good close-up pictures of hard dicks, but usually the men's faces are blurred or cropped out, which is disappointing. The face is important too.

I often showed Matt these sites and he was very nice about it. He didn't act grossed out or anything. He'd let me spend a lot of time looking at naked men, and we'd compare one dick to another, and, of course, the dicks on the screen with his. His is very nice.

I was fascinated with his dick, and played with it even when we weren't having sex. I liked watching it dangle and swing when he walked, and I liked making it flop around when it was soft. I didn't get to do those things much because as soon as I started playing with it, it would start getting hard, but that was OK because there are a lot of things you can do with a hard dick. (I bet you already knew that, didn't you?) I liked touching the soft silky head, and catching the little drops of wetness that come out of the tip when it's hard. I liked to trace the veins that run under the skin. I liked watching it get hard, which it did quickly, and watching it get soft after it squirted, which was slower. It took me a while to figure out what foreskins are about because Matt didn't have much of one, and even longer to figure out balls, which are tricky things. Sometimes you're allowed to touch them and sometimes it hurts if you do, and they're different every time you look at them. What's that about?

Have you ever seen the movie Personal Best? There's a scene where Mariel Hemingway holds her boyfriend's dick while he's peeing and tries to aim it toward the toilet for him. We did that. My aim wasn't so good and it made a bit of a mess that we had to clean up, but it was worth it. Dicks are fun even when they're soft.

I guess Matt understood why I was so fascinated with his dick. One day, he asked me, "Have you ever seen anybody else's dick?"

I shook my head.

"No boyfriend? Not even your Dad or brother?"

"Not since Jacob was little. That doesn't count."

"No, that doesn't count. Did you want to—see other dicks, I mean?"

Of course I did, ever since I was ten. So I nodded, "Sure. All girls do, don't they?"

Then he was quiet, and I could see he was thinking, then he said, "We'll have to do that some day." I didn't know what he meant, so I let it pass. He didn't elaborate.

He knew I was interested, so sometimes he'd tell me about the dicks of his friends and the dicks he'd seen in the school showers or at the gym locker room, but of course those were soft. He had one friend in seventh grade that he'd seen hard, and also his brother, and he told me all about them and what a shame it was that I'd only seen his.

We didn't look at just porn sites of men. We saw lots of pictures and videos of couples having sex. I'd mouse around until I found an interesting one, of people doing something new and different. We'd look carefully at what they were doing, and if I liked it, I'd say, "Let's do that." And we would. We found good positions that way. I discovered that I really liked the spoon position, when Matt would reach around from behind and play with me while we were doing it. It's very relaxing, when I wanted to be relaxing. There's also the reverse-cowgirl, for the same reach-around reason. We tried doggy-style and I didn't really enjoy it, but a lot of people on the Internet seem to. I guess everybody's different.

We found instructions for how to give a blowjob, complete with close-up photos. I knew he would want that and it looked interesting so I said, "Let's do that." Needless to say, Matt was happy to do that, and we've practiced a lot, using the Internet to improve my technique. Matt showed me how to use my hands along with my mouth, and I'm getting better every day. It's actually kind of fun, and I like watching him squirt, which I don't get to do if he's inside me. It goes all over his stomach and it takes me a while to clean it up. He's got a hairy stomach and it's tough to clean.

We also found porn sites with men giving oral sex to girls, and I wanted to try that but it seemed rude to ask. It looked pretty gross to me. But Matt spoke up for me. "Let's do that," he said, and I smiled, and we've practiced that a lot too. It feels good, but not as good as when he's inside me. He does it whenever I ask, and he's trying hard, but I'm not sure he likes it. I guess it's an acquired taste, if you know what I mean.

We stumbled into a site with anal sex, and I was afraid I'd hear "Let's do that." He was quiet, though, and I was glad. Maybe some day I'll offer him that, maybe for his birthday or something, if he really wants to. He hasn't asked for it.

I figured that Matt would want to see sites with naked girls, so I browsed to some of those. I don't normally like looking at naked girls. It's not a fear of being a lesbian or anything like that. It's that they always have big boobs -- or at least bigger than mine. I don't want to look at girls with D-size boobs. Let's be honest— I'm jealous. It makes me tense. But I knew Matt would want to see, so I pulled up some of those.

The surprise was that Matt wasn't interested, or at least he said he wasn't. Maybe he just knew how I felt. (How could he not know?) But he had other ideas. He did a search for "tiny tits" and came up with some places I'd never seen before. "These are much better," he said. Matt always knows just what to say.

The girls on these sites were nothing like the D-cup fake teenagers we'd been looking at. This was different. They were real. A lot of these girls had more than me, to tell you the truth, but not a lot more, and some had "boy-chests," just like mine, with no boobs at all. They just had nipples, big or small, pink or brown, pointy or puffy, all on full display, proud and uncovered and sexy as hell. Sexy as hell.

These were very pretty girls, about the same age as me, with beautiful hair and makeup and perfect legs and butts, and you could tell by looking at them that they could have any man they wanted. There were white girls, black girls, Asian girls, Latin girls, blondes and brunettes and redheads, all with tiny boobs or no boobs. Just like me! Exactly like me! Not one of them was the slightest bit embarrassed. They didn't wear silicone inserts, they didn't want boob jobs, and they didn't hold their hands over their chests. They wanted everybody to look.

Some of these girls were just posing naked by themselves, some with their legs open and some not, and some were posing with other girls, small as themselves. But some were having sex. They had big handsome partners with big handsome dicks, sliding in and out of them, in all sorts of positions. The men were kissing and touching and sucking and caressing their nipples and the guys were loving it and the girls were too.

I was transfixed. It was a revelation-- these girls were gorgeous and sexy and people had paid them real money to take naked pictures of them, and other people were paying real money to see the pictures. Small boobs weren't holding them back. They loved their small boobs-- their teeny tiny boy-chest almost-nothing boobs.

These were the girls Matt wanted to look at! He wasn't interested in D-cups -- he wanted to see these! His dick was very, very hard against my butt as I sat on his lap, so I knew it was real. He wasn't just pretending. He really loved tiny tits. He really loved boy chests. He really loved me, the real me, just like I was.

I felt like hugging him to death.

We spent a long time at those sites, and Matt carefully admired each and every girl, most especially the ones with the very tiniest boobs, comparing their nipples to mine and wondering what they would taste like. He'd sometimes take a break from browsing to pay attention to my real-life mini-boobs, touching and kissing and sucking and telling me how beautiful they were.

He loved the tiny tits sites. One night, he pulled his credit card out of his wallet and actually bought a month's subscription to the very best boy-chest site. We'd never paid for porn before, so this was special. God, this was special. I watched him pay and I saw the love in his eyes and the hardness of his dick.

I don't have to tell you how this made me feel. I grabbed Matt and threw him down on the bed and climbed on top of him, cowgirl style, and we did it like we'd never done it before, with his hands all over my boobs. My beautiful, boy-chest, size AAA, training-bra tiny boobs. All over them. My boobs. My real, sexy, lovable boobs on real sexy, lovable me!

That was the night that I had the very first orgasm of my life. I was riding on top of him, feeling his hands and his lips and his tongue on my nipples and he was telling me how beautiful my boobs were, even better than the girls on the Internet, and how good they tasted and how he thought about them all day when he was at school and how he wished he could kiss and suck them every minute of every day. At first, I felt the sensation rising up in me like it never had before, so I rode him harder and faster and moved myself so that I was rubbing my crotch just the right place against his dick, and his pubic hair was against me, and Matt's thumbs were one on each nipple.

Then it happened. I had a great big mind-numbing toe-curling authentic orgasm, and I sounded just like Meg Ryan in When Harry Met Sally, but it was for real. No faking. I had what she was having. I felt like opening the window and screaming into the street, just like Peter Finch in Network, but I'd scream "I'm sexy as hell and I'm not going to be embarrassed any more!" I wanted everybody to know!

When it was over, I fell onto his chest, my heart pounding, sweating all over, and kissed him, with all the passion that had been welled up inside me for all these years. Then I rolled off and cuddled up next to him. I knew then that my life was never going to be the same. A new adventure was beginning. A great, big, new adventure for a sexy new me.

You know what else happened that night? He told me he loved me. Just like that-- he said it. "I love you Jill." I had my head on his chest and his arm was around my sweaty back and I could feel his chest hairs tickling my face, and he said it. He said it. And I said it too. And I meant it.

That was the night my life changed.

-- --

After that, we spent even more time on the Internet. We hardly went out at all unless there was a good movie on campus. Instead, we spent the evenings in my bedroom, looking at tiny tits, then making love and having orgasms. Lots of orgasms.

Matt knew a lot about girls with small boobs. I guess he's been studying the topic for a while. He showed me photos on the Internet of celebrities with small boobs. There were beautiful, famous, sexy celebrities, with boobs not much bigger than mine. Natalie Portman. Calista Flockhart (yes, Han Solo's wife). Julia Stiles. Keira Knightley. Lucy Liu, and more. Some of them even had topless pictures.

I saw that Goldie Hawn used to have small boobs when she was young. We watched her daughter Kate Hudson, dancing topless, in Almost Famous. It's a very short scene, but you can clearly see her pointy AA's if you pause the disk at just the right time. I was disappointed to learn that she'd gotten implants since then. Oh well.

We learned that Sandra Oh is almost as small as me and she did a nude dance scene as a stripper in a movie. She didn't mind showing off her boy-chest. There were nude photos of Brooke Shields too, completely flat-chested, from Pretty Baby, sexy as hell, but she was just a kid then so that doesn't count. She has bigger boobs now. I don't know if they're implants.

We streamed Dancing at the Blue Iguana, which is the Sandra Oh movie. She has a scene where she dances for a long minute or two wearing only a G-string, and there are some good close-ups of her boobs. She's probably a AA, a little bigger than me, but not a lot bigger. We didn't pay much attention to most of the movie, but we watched that scene over and over. About the third time through, I decided that Matt was having such a good time that I'd blow him while he watched, so I got down on the floor in front of the desk chair. He was really into it, each time rewinding so he could watch the scene again, pausing the movie at just the right time to see her boobs.

He was enjoying the movie (or maybe the blowjob) so much that I didn't have the heart to pull away at the last minute, so instead of squirting on his stomach or on me like normal, he squirted in my mouth. I thought it would gross me out but it really wasn't bad. I guess I could do that again for him. He's so sweet to me, it's the least I can do.

One day, I was sitting naked on Matt's lap and we were looking at porn-site pictures of girls with boy-chests. I had a germ of an idea. "Do you think my body looks like a boy?" I asked.

Matt laughed. "What made you think of that?"

"These girls. The site says they have boy chests." I turned my head and looked at him, "Answer the question. Do you?"

Matt laughed some more. "Can you feel my dick against your butt?"

"Yea. What's that got to do with it?"

"Does it feel like he thinks you look like a boy?"

His dick was as hard as a baseball bat. "I guess not," I answered quietly. I didn't pursue the point. I noticed that he hadn't really answered the question, and I wondered whether that might be a good thing. I didn't know what I thought, but I bet Matt did.

Matt couldn't stay overnight that night, so after he left, I popped a DVD into the player and watched Victor Victoria. It made me think.

-- --

Ever since we'd starting making love, Matt had wanted me to go out in public au naturel. I don't mean naked, of course. I mean without my bra inserts. Or maybe -- he dared suggest -- without a bra at all. I wouldn't do it. No way. Nope. No can do. But then there was the night my life changed--the night that I discovered that tiny tits are sexy.

Then I started listening to him. He told me that my boobs were as beautiful as the rest of me. He'd been telling me that all along, from the first time he saw them, but I was able to hear it now, and, little by little, I started to believe it. I looked at naked girls on the Internet and didn't get tense or jealous, even if they had B, or C, or D boobs.

I still put on my bra with the inserts every morning, but now I started to think of them as a habit, not a necessity. I would possibly have been willing for people to see me without them, but I knew that everybody would notice the change and I didn't want it to be a topic of discussion. Can you imagine the looks I'd get, and the rude remarks-- "Hey Jill, what happened to your boobs?" I didn't want people to be snickering behind my back, so I wore the inserts.

But Matt had a good point. Maybe it would be ok if we went out where nobody knew me. If they'd never seen me with boobs, they wouldn't notice a difference and it wouldn't be a big deal. He was persistent, and I really wanted to do it, so I agreed to go shopping, reserving the right to back out if I got embarrassed or scared. We drove to a mall an hour away to make sure I wouldn't see anybody I knew and I shopped for a top that would fit me properly without B-cup fake boobs. I wanted a pretty, sexy top. Girlie, not boyfriend.

I looked through the racks and picked out a few possibilities, and went into the dressing room and tried them on. I looked in the mirror and liked what I saw, so I came out of the dressing room wearing a pretty pink-on-pink one. I went in with B-cups and came out with the real me, my bra in my bag.

Matt liked what he saw, and I liked the look on Matt's face. He was perfect, with a look full of sweetness and love, and he told me how beautiful I was and I knew he meant it. I looked in the mirror again, and he was right. I was as beautiful as the girls on the Internet. I bought the top, took off the tags, and wore it out into the mall. The old me was in my shopping bag. The new me was in public at the mall.

I quickly learned some of the advantages of going braless. As I walked, the top rubbed against my nipples and made them hard and it felt good and made me feel sexy, with lots of hormones running around inside me. Best of all, Matt had easy access. When we got in the car after shopping that first time, Matt leaned over, kissed me, and stroked my nipple through the top, with no bra in the way. Then he put his hand under the cloth and massaged my nipple, right there in the parking lot of the mall. I knew I was going to like being braless.

Little by little, I got braver about going braless. I'd do it whenever it was just Matt and I, away from people I knew. Matt would take every opportunity to sneak a peak or put his hands in naughty places when nobody was around, and that made it even more fun.

I worked up the nerve to not wear inserts when I was with my family. I told Mom in advance so that she'd make sure Jacob would keep his mouth shut. He knew what my real boobs were, of course, because he'd seen me in my nightgown or pajamas and I wore no bra then, but I didn't want to hear his comments when I was in regular clothes. He would certainly have come up with a series of wise remarks, and I didn't want to have to smack him. (Normally it would have been fun to have an excuse to smack him, but not this time.) Mom promised to keep Jacob under control and, by the way, told me how glad she was that I'd learned to be happy with "my beautiful self."

Of course, I kept wearing inserts to work. There were too many people there who would have made my life hell with their imitation of humor. That was non-negotiable.

I felt so free now. I was the real me.

-- --

It was summer now, time for swimming, so Dad filled up the pool in the backyard. It's not one of those expensive fancy in-ground pools, but just a simple above-ground kind with a ladder that gets you to the top. I bet you're wondering if I wore a bathing suit without inserts, but I have to confess that I didn't. Not around people I knew. I wore the inserts.

One day, my brother had some friends over to go swimming. I sat in a lounge chair, watching all his friends in swimming trunks, and I looked at their chests and thought about mine. People have always said that I look a lot like my brother, with the same nose and the same hair. Matt says we have the same beautiful eyes, but I told him not to say that to Jacob. I don't think Jacob would consider it a compliment. Looking at Jacob in his swimming trunks, I thought that we looked alike in other ways too, but I put that thought out of my mind.

Matt and I spent less time on the Internet now, partly because we were running out of new free porn sites to see and partly because it was more fun to have sex ourselves than to watch other people do it. Also, we were more experienced now and had less need for instruction or ideas. We did spend some time though at the "Nude in Public" sites, looking at girls flashing at Mardi Gras, or at Key West, or in wet t-shirt contests. The girls always had big boobs, but that didn't bother me anymore and I enjoyed looking.

Of course, there were the nude beach and topless beach pictures, mostly from Europe. I guess they go topless a lot there. There were girls wearing nothing but thong bottoms, with crowds of people around, and they weren't the slightest bit embarrassed. They weren't even drunk. Just relaxed, casual and care-free. When we porn-surfed, I was always the one sitting on Matt's dick and driving the mouse, so I spent a lot of time at those sites, and I wondered if he knew what I was thinking.