Pretty Girl of the Day, Sept 2, 2016



As a brand new freshman, you can understand, I hope, that the rules here at the College are, well, a little scary to me. So when a boy asked me to prove I wasn’t wearing a bra, I really didn’t know what to do. Of course I know the rules, and I’m happy to follow them. Proud, in fact. So I took down my top, and showed him my tits.

I really thought that would satisfy him, but he wanted more. I asked him if I had to get naked, and he laughed, and said of course not, he just wanted to make sure I was following the Dress Code.

Let me tell you, that was such a relief! He was really looking out for me, it turns out. He helped me understand that I really didn’t need to be wearing so many items of clothing. The top overlaps the bottom, he said, so one of them is superfluous.

“Should I take off my top, then?” I asked him, starting to remove it. He waited for me to take my top off, and held out his hand so I gave it to him. Standing there, completely topless for all to see, I started wondering if I would be okay spending the rest of the day wearing just my shorts. To be honest, I found it kind of exciting. I felt my lips swelling, and pressing against the crotch strap of my shorts.

He could see I was feeling vulnerable without a top, so he came closer, and put an arm around my waist. With his other hand, he stroked my nipples until they got hard. “Do you mind if I check your shorts?” he asked. Check them for what, I wondered. Without waiting for me to answer, he undid my shorts, and felt inside. I was really happy I had shaved completely, and that I wasn’t wearing any panties. When he was done feeling me up, he said, “you should really leave them undone.”

“Why?” I asked.

He explained that some girls wear shorts to try to hide things, you know, like a bush, or even panties. So if you’re going to wear just shorts, it’s good to leave them completely open.

“But they would fall down whenever I walk,” I said.

He laughed. “Yeah, I know that can be embarrassing. That’s why a lot of girls solve their overlap problem the other way.” He must have noticed my blank expression, so he explained: “Girls like to wear a top, and no bottom.”

“Ohhh!” Suddenly it made a lot of sense. If I wear just a top, I can easily lift it whenever a boy needs to check that I’m following the dress code, so it’s a lot simpler than wearing shorts. I took off my shorts, and waited patiently while he handed me my top.


To be honest, I still felt slightly naked. Well, not naked, exactly, I guess you could say I felt “bottomless”. The boy helped me understand that my top was really plenty long enough. After all, he explained, it overlapped my shorts, so according to the Dress Code there’s no need to wear shorts under this top.

I asked the boy if he thought it was okay for my butt to be uncovered. He was so sweet. He tried to tell me my butt really was covered. He tugged on it, and put his fingers on my asshole, prompting me to spread my legs to give him full access. “See?” He said. “I’m reaching under your top to touch your asshole, so it’s completely covered. You have nothing to worry about.”


I really think he was just being nice, because whenever I sat down, and spread my legs, my pussy was fully visible. Even though I was following the Dress Code, I really felt bottomless that day.

That said, no one made me feel uncomfortable wearing that top. Some boys stroked my inner thighs, prompting me to spread my legs, which I was happy to do. When my pussy happened to be wet, I was a little worried I would be consensually raped, which is perfectly legal according to the Code of Conduct, but no one raped me that day. Sure, a lot of boys fondled me, and I even came once or twice, but that was it.

I would say that boy gave me some pretty good advice to wear just a top. I’ll keep it in mind for the future.