My girlfriend is 29, and we started talking when I was 16. Had sex the first time (with her) when I was 17. Now, I'm 19, but people are always surprised to hear this because I'm fairly short (5'1") and apparently I look like I'm 12 or something. It doesn't help that I don't really grow much body hair.
So, yknow I thought it was super awesome (still do, though it's a bit awkward right now) that this older chick was into me. Just thought I was lucky as hell.
So I'm on her computer and I'm on the internet, forget that it's her computer so I go to check my bookmarks. Her bookmarks are absolutely filled with thousands of links to pages and pictures of like, "traps"/crossdressers, and Hentai featuring those kinds of characters but also like cute young boys?
At first I just kind of went okay that's a bit weird, but whatever. But then I thought about it, that's me. That's why she likes me. I'm this cute little boy to her, and it's a perfect situation because I'm over 18 (now, not that I was when we started talking, or when we first had sex) but I still look really young.
And like, I went from, at the start of our relationship i was wearing really baggy clothes to now I wear tighter clothes that show off more skin. A lot of short shorts and tank tops. Because she seemed to be more handsy/want to have sex more often when I wore clothes like that. And she's jokingly suggested I dress up like a girl, but now I'm thinking that was to gauge my response?
I don't know. I'm very confused. She's going to be home in a couple of hours. I don't really feel any differently towards her, I just kind of feel, I don't know, embarrassed? To have this insight into how she sees me?
When she gets home, I'm going to give her a hug. We're going to eat. Then I'm going to ask, as innocently as I can manage, if she wants to dress me up in girls clothes.
- That's Juicy! 15
- Remove It! 0


