Chelsea the Insecure Waitress

Chelsea and I knew each other for a long time. We'd been friends in high school, then met in our early 20's and hooked up. She was quite the catch. She was very pretty, with pale, pinkish skin, an oval shaped face, straight dark brown hair and big doe eyes. She was thin (maybe too skinny), but had some surprising curves. She was cool in a mysterious, serious, sort of gothic way. She was also a hard worker, holding down multiple waitress jobs to her and her cats and dogs on their own.

As I spent more time with her though, I learned more and more. It turned out Chelsea was very insecure. I learned about it in more and more ways. First of all, she was reluctant to have sex with the lights on. She also kept her bra, or sometimes her shirt on. Then, as things progressed, those barriers broke down and I learned why. It turned out, she was very insecure about her small boobs. And they were quite small. She didn't look like she had big breasts, only about a B cup, but then I found out almost every bra she had was padded. Not a ton, but underneath the padding: well, I wasn't going to pry and ask her cup size, but... AA? If she needed a bra at all? Just two perky little mounds, maybe the size of kiwis, with two pink, shockingly erect nipples (I like to thank that part was due to my presence, but honestly she was probably just excitable). Anyways, she was extremely shy about her small breasts. I think part of this had to do with her sisters. She had two sisters that were each C cup if they were anything. All three girls looked extremely alike, and Chelsea often compared herself to her sisters unfavorably.

I learned more and more. She was extremely skinny in part due to an eating disorder in her youth. That may have contributed to her very undeveloped chest. She still worried about her weight constantly. I guess she was a heavy set kid and the cruel comments got to her. Now, in her early 20's she was very thin, but still concerned about her figure. It was true, she had a slight belly, which did kind of stick off her thin torso. And, despite her longtime concern, She had a surprisingly large butt that she viewed as unsightly. I suspected this was why she often worse skinny jeans, to make sure no jiggling ever showed in public. Luckily, I got to see plenty of jiggling, and I found every inch of her backside (and whole body) totally perfect. She also thought she had stubby legs. This was probably just do to her long shifts waitressing on her feet, giving her thicker legs then her thin upper half, but anyways it was another thing she viewed as a flaw.

She was so insecure about her appearance it seeped into her dreams. Once she told me she had a nightmare where she showed up at work in just her underwear.

"That's embarrassing!" I said. "Do you have that kind of dream a lot?"

She was visibly blushing thinking about it.

"Pretty often yeah..." She said. Sometimes I'm naked in public. I don't want to talk about it."

Now, this became a bit of a fantasy for me. I'd think about her exposed in public like her dreams. I know that these dreams were a byproduct of her insecurity, and I feel bad that she can't see her beauty. but something about her nervousness, combined with her frankly extreme arousal (She was an exceptionally easy girl to get off, probably a byproduct of repression), just morphed into an erotic fixation. I wanted to see her exposed. I wanted her embarrassment dreams made real!