How many dates until you ask to live out a fantasy?

How well should you know your partner before you ask them to live out a fantasy?

I was embarrassed about my fantasy for years, kept it to myself. The first girl I asked to live it out with, we'd been together for just over a year. She absolutely loved it, we did it loads when we were together, and she was very involved in making it good for me!

That went well, so the next girl I just waited a few months. She let me do it to her, but I think she was just letting me, she didn't really like it. The next one just a couple of months, who loved it. I'm now on the fourth girl I've done this with, and she loves it too! I told her about my fantasy on the third date, and she let me live it out a few dates later. Yum :-)

So how far can this go? Would you let a guy live out a sexual fantasy the first time you sleep together? Maybe I should put my fantasy on my dating profile and get straight to the point :-)

You're probably wondering what my fantasy is... princesses! I love girls dressing up as a princess. I keep a few prom and bridesmaid dresses in ready, and I love feeling the sexy dress fabric against their skin. Normally I'll undress them, get them to put a dress on, add on sparkly shoes, jewelry, tiara/fascinator, maybe some stockings. Then we'll just lie and cuddle, watch some TV. And then I'll lift up the poofy skirt, slide my cock in, and make love to a princess. I love it!