Nancy was almost old enough to be my mother. Almost 20 years older than I was. At the time I was 40 and she was in her late 50's. She didn't look it though. She had long red hair, hazel eyes, small c cups, and a great looking ass to hold onto.
Even though she was married, Nancy was a lonely woman. Her husband stopped paying attention to her a long time ago and even though she was miserable, a divorce was not an option for her, fearing the financial outcome of all of it.
She always went to the bar alone or with her female friends but never with her husband. Even though I couldn't say for sure, but there was a pretty good chance she's had a few affairs over the years with a few of the older regular that hang out down there.
The two of us always got a long really well. We sang karaoke together, got drunk together and even went out dancing together a few time. Even though I found her somewhat physically attractive, I always felt that me and Nancy had more of an emotional attraction towards each other. We often consoled each other during difficult times and celebrated during the good times. We overall held the same religious beliefs and shared the same morals.
Yes, there was always some kind of sexual tension between the two of us. I think it more had to do with curiosity than anything else. To me, she was untouchable because she was married and I was untouchable to her because she thought I was too young for her but she always would ask me 'How old are you again?" whenever we would slow dance.
There were always rumors about the two of us. Up until recently, the stories were all false. There was no affair of any kind between the two of us. We respected each other's status and boundaries and we felt pretty safe whenever we were around each other. We spent a lot of time together but we never got intimate. Until now.
I never intended to have sex with her. Sure I often wondered what it would be like when I was alone and jerking off before bedtime but even if I wanted to really, truly have sex with her I couldn't imagine it ever happening. I also couldn't imagine it being enjoyable simply for the fact it would probably be awkward for me being that she is married.
For years we were planning on going to the Casino together. She went often and had perks such as free room and meals. We had planned that one of these days we'd go, drink, eat, gamble and share a room. It's possible she was hinting at something sexual would happen but I never really processed that in my mind. She was simply off limits.
Well the time was right and we were finally able to plan the Casino trip together. She already had the room the day prior and spent the night and I had met her the following day after work. I met her at the hotel lobby and she took me to her room so I could put my stuff down.
I was so exhausted from a long day at work, I took a shower and we headed out to the gambling floor. Whenever I go to the Casino (Which is rarely) I am strictly a slot person. She must have been a good luck charm because within 20 minutes and $10 into gambling I had to stop because I scored a $1000 win on of all things, a penny slot.
The night went on, I watched her gamble and blow more money than she should. We ate at a nice restaurant before going to a bar/nightclub inside the Casino for the rest of the night. We tore the place up with our dancing and drinking. We had a great time.
We left the club earlier than we normally would because we were pretty exhausted. I must admit that I wasn't as fucked up as I could get whenever I go out with her and she wasn't as bad either. We were a little 'Tipsy' but we were having a blast.
We went back to the room to retire for the night. I brought a box of wine to the room earlier that day and I wasn't exactly ready like I thought I was to go to sleep so I began having a few glasses of wine. She had a few herself. She got changed into a nightgown when I was in the bathroom and was getting ready to call it a night. Seeing her in her nightgown was something I wasn't quite expecting. Not that I'm prudish and never seen a woman in her bed clothes it was just that it was her, being almost 60 years old and feeling like I'm rooming with my mother or great aunt.
She brought her tablet along so she could kill time if she had to before falling asleep and she took it out and began messing around with it. I was on my bed (We had separate beds) drinking my wine and watching TV.
"Mike your good with tablets, can you come here and help me with something" she asked me.
It seems she was having some problems with apps crashing on her, so I climbed on the bed and laid down on my stomach next to her (She was laying on hers) as I was trying to help her with the tablet. I was in a t-shirt and boxers.
In the course of helping her with the tablet she started to ask me some personal questions about my love life.
