I was 21, on my way to visit a friend of mine during a vacation during college. I was flying from Philly to San Diego and had to change in Phoenix because I was flying Southwest Airlines.
At the gate, I kept catching the eye of a woman who i thought was really pretty. I guessed her to be in upper 30's; she was curvy, had dark brown hair, really sexy green eyes, and pouty red lips.She was wearing a medium length black skirt, a red blouse and looked like business-type traveler. This was during a phase when I found older women really attractive (I sometimes still do); had fantasized a bit but never been with one; had played with one a lot online and even on phone who i thought looked a bit like her; so i was a bit intrigued by this woman, and surprised that she seemed to be looking at me as much as i was at her.
Because it was Southwest, we boarded plane with option to sit wherever we pleased. I was in the second group, so she boarded before me. I was debating whether or not I'd sit next to her if her seat was open; trying to work up the courage, but at the same time, hoping that the seat next to her would be taken so I wouldn't have to decide.
As it turned out, there were only about 10 empty seats by time I got there, and the one next to her was open. It was a 3 seat row and she was in the window seat. A senior woman was in aisle. I decided to go ahead and sit next to her.
For the first 30 minutes ,while we taxi'd and took off, we each just read our own books, but occasionally caught glimpses. Finally, she introduced herself as Katherine, a 43 year-old consultant from San Diego. I noticed no wedding ring, but a tan line on her ring finger. I introduced myself as well. We made small talk for awhile; she had had friends that went to my college when they were younger, etc.
We then took a break from our small talk, at which point we went back to reading. I must've dozed off; at some point, I woke up, and her hand was on my thigh (I was wearing jeans); not sure if I was having any dreams, or anything, but when I woke up, I was a bit hard. I was not sure if it was from a dream or from her touching me. I pretended I was still asleep as I was embarrassed. She kept rubbing the thigh, occasionally sneaking a hand further up towards my zipper. It was driving me crazy to pretend to be asleep. She at some point stopped and I dozed off. When I woke up, she was asleep against window, and I went to open my book, and there was an envelope that said, "Please open after plane lands". At this point, there were just 30 minutes left in flight, so I fought my desire to open the letter, which I presumed was from Katherine. I spent time fantasizing about her, hoping maybe she gave me a phone number but figured she probably just had a question about her friends' old college or something.
After we landed, everybody stood up to get their bags. We each went to aisle and got our bags. While waiting behind her, I opened the letter. It said, "I hope you don't mind i touched your leg while you were asleep. I'd love to get to know you better. If interested, wait 5 minutes after de-planing, go to men's room, and go into first stall."
