My Shemale Fantasy

She was dressed in heels, stockings, a black dress that came to her knees, and half long black hair, clipped up. She wore make up, but not too much. I think she had a B cup, dark red lipstick,…u can guess how i felt by now. I always had a hard time talking to women, but these few drinks that i had did make me feel more courageous. When the bartender charged her for her drink i volunteered to pay for it. “Now why would you go on and do that?” She said with a smile. I answered that this is probably the only chance i’ll get to spend time with a beautiful woman. This came across as maybe too bold in my mind, but to my utter surprise she was flattered and asked how old i was. “23” I said. She introduced herself as Bianca, 32 years old. We started talking..and drinking more. I found out she didnt go out too much, as she was busy with her job and that she feels rather insecure when being so “out in the open.” This surprised me, cuz i imagined every guy probably wanted to hit on her the second she walked in. Who wouldnt be flattered by that? We got to talk and laugh about common daily things, like what went through our minds when waiting in line at the supermarket behind some old lady with change, how we both loved italian food,…The second she decided to pay for the next round, i knew that i was going to at least have a few hours of fun with this beautiful woman who actually had a thing or two to say. Quickly she changed the subject by: “So, does your girlfriend know you’re talking to another woman? An older one might i add?” I answered that “I didnt have a girlfriend and that most women i met didnt quite do it for me. She asked me what my type was then…”older women….they have more to offer” She hesitated and looked insecure and i asked what was wrong. She said she wasnt used to made feeling this way….As the drinks passed on, and we talked about our past lovelife, i asked her what was the barrier between her and some sort of relationship, pure sexual or something more “real”.