I've been fantasizing about this roleplay scenario and would love to act it out with the right woman.
I have a crush on a former high school classmate of mine who works & lives in Manhattan. She is currently engaged. I'm kind of bummed that I never revealed to her how I felt about her.
So my fantasy is that I'm up in New York for business. While I'm in Starbucks, my crush recognizes me and comes over to give me a big hug. We sit down for a few minutes to get caught up. She tells me that she's engaged (she shows me her big engagement ring), but tells me things have been rocky with her fiancé lately. I console her and tell her she deserves better. I work up the courage to give her a heartfelt talk about how much I liked her in high school & how much she secretly meant to me. She is really touched and tells me how much she wanted to go out with me, but because I was so shy, she thought I didn't like her.
She tells me that her fiancé is out of town on business. She suggests that she could use some company back at her apartment. She tells me that she has been trying to get pregnant, but has been having trouble with her fiancé. She asks if I would have any interest, and I happily accept. On the way to her apartment we stop at a pharmacy to pick up some lube/lotion and a pregnancy test (I have a fetish for these things and it would turn me on to buy these with a woman).
When we get back to her apartment, to get in the mood, I suggest that we slow dance together like we did back in high school. It turns into a lot of kissing and you can guess where it goes after that. (of course we use protection, it's all for fun and roleplay the whole pregnancy stuff)
This might be kind of fun to continue to roleplay on a second date. You could wear a pillow or something under your top, LOL
I am looking for a white woman, preferably early 20's to mid 30's.
If you like the idea of this roleplay, please get in touch.
Thanks!!!
