Fifteen years ago we were a young high school couple going through puberty and exploring ourselves. We would often find ourselves on the couch at my parents' house deeply kissing and groping one another, but the clothes never came off.
A few years later after fading apart, we were re-acquainted in college and I decided that I wanted to be with Heather and to be a better boyfriend. She had developed into a beautiful woman. She was 5'6", 135 lbs, had a beautiful smile, deep blue eyes and double D breasts. When I finally had the nerve to tell her, she had news of her own. She had a boyfriend and she was no longer a virgin. The next year consisted of us getting together every month or so and her talking about getting her brains fucked out by her boyfriend who didn't really like being with her very much.
Heather eventually went on to cheat on him with various other guys and she loved telling me about it. When I finally told her that I was still very attracted to her, she shrugged it off at first, but then realized it was pretty serious. We had plans to get dinner and to talk about things and my feelings for her and she showed up 45 minutes late and she was not herself. I was proposing for her to break up with her boyfriend and to be with me, but instead she found a freshman boy who she found attractive and let him fuck her brains out.
A few weeks later I put the moves on her, we were making out and groping one another, and she put her hand down my pants. Within a few minutes she stopped everything and said, "we can't do this."
More than a decade later after that frustrating scenario, I happened to be in LA and decided to look Heather up and call her. I was fresh out of a divorce and had nothing to lose. We had dinner and caught up on old times and really hit it off like not a single day slipped past us. She was in yet another bad relationship, not into her boyfriend at all, and cheating on him from time to time. She was afraid he'd find out and was getting ready to break up with him in fear of his reaction.
We were really hitting it off at dinner and she asked if I wanted to go get drinks nearby. We walked to a bar and sat down. It was darkly lit and pretty loud. We had a small booth table and though we were surrounded by other people, it felt intimate. After a few drinks she mentioned that she felt badly for cheating on her boyfriend, even though she didn't like him. She then made a comment that implied that she was going to cheat on him again with me.
I said, "I'd be so happy to have you in my life that I'd be ok with you cheating on me."
She almost spilled her drink, "no you wouldn't."
"yes, I would. I've masturbated so many times to the dozens of stories you've told me about over the years - where you fucked the waiter, your co-worker, your professor, the freshman boy. All of them get me so hot."
"and you'd be ok with me cheating on you if we were together?"
"it wouldn't be cheating...who in this room would you want to fuck?"
she moved over closer to me and for a second I thought she was going to say me...especially when she slowly started sliding her hand down my pants.