So, I just had a major realization about why my girlfriend likes me, and why she's asked me to do some of the things she's asked me to do.

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.

Comments

Anonymous

by Anonymous on Apr 25, 2016 at 8:22 AM

The answer she is going to give is yes, then get ready for a wild night of sex! I have done the same.

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Anonymous

by Anonymous on Apr 25, 2016 at 10:25 PM

I cross dressed for her. Conveniently she already had outfits in my size. At first she just wanted to watch me masturbate while I wore them. Then she started playing with my ass. She had mentioned wanting to do it before, but I never really felt comfortable with it before. Maybe it was the cheerleader uniform she had me wearing at the time.

She kept telling me how cute I was, how adorable I looked while she was exploring inside me with her fingers and stroking my cock, using toys on me. We didn't get to a full sized dildo, but we played with a small plug and anal beads.

She asked me to call her Miss, to act innocent, like I didn't know anything about sex, hadn't had it before, etc. and to not try and hide my reactions to how everything felt like I tend to do. She wanted me to act like some of the things she was doing made me uncomfortable.

There was something very different about her while we were doing all this. Kind of creepy, a little scary, like she was looking at me in a completely different way. If she was a stranger I think I would have avoided her, but because it was her it kind of turned me on.

When we were turning in for the night she wanted me to go to sleep first, she admitted it was because she wanted to watch me sleep for a while. It was difficult to get to sleep while she was just watching me, but I did. Woke up with her arms around me and stayed like that until she woke up on her own.

Indulging that side of her was fun, if a little creepy. Pretending to be some innocent boy being played with by a perverted older woman. I'm going to suggest we keep it up for a while.

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Anonymous

by Anonymous on Apr 26, 2016 at 12:20 AM

Run with it. You'll not regret it. If it's really not for you it'll become clear in time... meanwhile enjoy being with her.. you won't regret it I promise

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