First Femboy - Sex Stories

First Femboy

I'm an average divorced guy: middle aged, dad bod, decent looking, decent cock. I'm primarily straight in that I have only dated women and only find women attractive, yet find sex with someone with a penis incredibly erotic. I've experimented a little and had fun - those memories are often ones I relive in my fantasies.

One day while shopping at the local Trader Joe's, I encountered a being I had never really known about at the checkout. He was tall and thin with long hair and feminine features. He wore feminine clothes and even had a bit of makeup on, but otherwise spoke and acted like a boy. As he rang up my groceries, we interacted a bit and I felt like he was checking me out. I paid and left but was left with the impression that a bit of flirting had just happened with this young man. I was a little flattered and a little intrigued. What would it be like to hang out with such a human? A completely new experience. The thought stuck with me.

A few months went by and the relationship I had been in for a while ended. No good guy, no bad guy - she was just in a different place in her life and I didn't fit.

After being single for a while, the thought of the checker came back to my mind. I decide to go shopping and see what I could find. No luck. I bought a few things and could not find him. Perhaps I had waited too long and he had moved on. I let the idea go and got about my life. After a few more trips to TJs, I wasn't even thinking about it - when who should be there ...

... than my curiosity. I grabbed what I was there for and got into his line even though there were other shorter lines available. When he finally got to me, we chatted again but I lost my nerve. I had not been mentally prepared for him to be there, and then I thought why would someone so young want to have anything to do with me? I bought my stuff and left.

As I was getting to my car, my new friend - Jamie - came up to me, letting me know I had forgotten one of my bags. I thanked him for bringing it out and mustered up the courage to ask if he would like to hang out sometime. He gave me his number and told me to text him. Wow!

I texted him later that day letting him know it was nice to meet him, that I found him intriguing, and asked if he would like to meet for drinks at a local pub. We set something up and met at 8. We had a few beers and told each other the major facts about our lives. For me it was college, marriage, kids, divorce, single life. For him it was just school, lack of sports, a litlle college, etc. After a few more beers I inquired about his sexuality, apologizing in advance for any offensive I might give in my ignorance. He was very open about and let me know that he was primarily attracted to older men - me especially (that was a nice flirty way to clarify why he was here :) - and that he did not have much experience yet. When he inquired about me I let him know my history - primarily women - not attracted to men but that I had fooled around a bit. I also ...