I have been married to my wife for about ten years and we are very happy together. That doesn’t keep me from looking at other attractive women though. My wife’s littlest sister, Tina, is about 10 years younger than she is. Tina is in her last year at a large Midwestern university. Since you can do the math, I have know Tina since she was a small child. She has always been cute, but she has blossomed since high school. She is about 5″ 4″ tall with a great ass and legs that match. She has very small breasts though. Her lips are naturally rose colored and her dishwater blond hair beautifully frames her deep brown eyes. Since Tina was in high school I have fantasized about her but, obviously, I could do no more than that. After she left for college in a town nearby my fantasies continued but I was always afraid to try to do more. Tina was always very shy and seemed to lack confidence in herself.
Even though she is beautiful and intelligent, she didn’t date. However, recently she started dating a guy and I have noticed a major increase in her self-confidence. She occasionally flirts with me now and I have flirted right back. I have been curious what brought about her rise in self-confidence so I thought I would take her to lunch and do some “investigating”. On one Thursday afternoon I picked her up at her apartment and under the guise of seeing how classes were going, I took her to lunch at a campus watering hole. When we arrived at the bar, we grabbed a booth and got our menus. While the waitress came by to take our orders, I watched Tina carefully. Tina’s eyes could make me melt and her skin looked like pearl. Earlier, when I picked her up I noticed her cut-off jean shorts. Now I noticed the tank top she was wearing and how tightly it snuggled up to her tiny tits.
While we waited for our burgers we both had a beer. Conversation was a comfortable and the beer helped loosen us up more. I told her that I noticed how she seemed like a different person since she began dating. She asked if that was good or bad. “Definitely good,” I said. “In what way?” she wanted to know. When I explained that I had always thought someone as attractive as her should have more self-confidence, she wanted to know more. I told Tina that she should be proud of herself and use her attractiveness to her advantage. She smiled and said she knew what I meant because she has just learned that herself. Now I was curious! “How have you learned that?” I asked. She blushed again and just said that things have been going “well” with her boyfriend.
Our food came and along with it another beer. We shot the breeze while we ate and ordered another couple of beers when the food was gone. We were both losing our inhibitions and I managed to direct our conversation toward sex. I asked Tina if she and her boyfriend “messed around”.
She giggled, blushed and said, “Yes. Well, what do you mean? We have done some things.”
“Have you two made love yet?” I asked. Her look of embarrassment was enough to give away the answer.
I pressed the issue a little more, “Did you like it?”
“Yeah. It’s better than I thought.”
“Really? What did you think it would be like?” my interest (and other things rose).
“Well, I was afraid it would hurt. Or that he wouldn’t like me,” she said.