[cators]

To tell a story right, you need to include as many details as possible and this is a great story so I want to share it exactly the way it happened. Trust me, you'll like appreciate it later in the story.
My girlfriend of 8 years is pretty conservative in nature. We are from North Carolina and when she graduated from college, a big group of us went to Florida for a week vacation. At the end of the trip, Lebo and I ( her nickname) went to South Beach. I talked her into going topless on the beach which completely went against the grain for her. When we were in the ocean at one point, I took her top off and she just walked out completely topless back to her towel. My jaw dropped watching this...she's got great tits and I'm sure others appreciated this as well. I knew she did it to make me happy as its nothing she'd ever do on her own. Like I said, she's conservative and while I tried to talk her into other fun adventures, she just wasn't up for it. A group of us went to Fantasy Fest in the Keys a few years later and while all her other girlfriends were getting painted up, flashing, drinking, and having a blast...she just wasn't up for it. she did finally wear a fishnet shirt without a bra one night near the end of our trip. No one could believe she would even do this as prunish as she is.
A year later she landed a big job in banking in Philly. I was working at a college in NC so we agreed to keep dating and visit each other when we could. After two years, she came back home super exhausted, stressed out, and decidedly against the banking world and the 60+ hours per week.
Her best friend lived in Vero Beach, Fl and kept talking to her about being a "cart girl" at this exclusive golf club down there where the cute girls made tons everyday selling beer and whatever else to the super rich. We talked about it... weighed out the pros and cons and how it would affect our relationship...so we hung out for a few months, had great sex..but finally I told her she should go down to Vero for a least a little while as I could tell she wanted to go. She could make some good money, get a tan, build up her funds and then come back and go to grad school. She thought being a cart girl was a little demeaning after her big banking job but I finally convinced her to go down there and get her act together. So we had a plan.
So she was making major cash down there and thus pressed me to help her get into the college I worked at in the Fall to start grad school. She was accepted within the program within a few months so I told her to just keep flirting with old farts on the golf course and bringing in cash throughout the summer. I visited her a couple of times and she came home a few times as well so things were really good.
In August she headed back home and started school. The perfect plan. So as you have probably figured out, its always been a turn on for me to see her to be at least partially naked in public and it was tough to convince her to go that route. During sex, I'd also tell her how turned on I'd be for her to have hooked up in Philly or Miami. She thought I was just fishing to see if she had fooled around. She kept saying she doubted if I'd been totally true so it was always a touchy subject. She'd tease during sex, but later would emphasize that she had never had sex with anyone when we were apart. I think I was 50% glad and 50% sort of like...damn we'd have great sex if she told me a good story.
Near the holidays that year we had finished a bottle of wine and decided to open one more. We just got crazy. Her boobs are big and drive me crazy. We had never done this before but we rubbed massaging oil all over each other and it was really intense. We started our crazy talk when she suddenly stopped, smiled, and said..."i told you i never hooked up and i never had sex when i was gone and that's true. I never did hook up or have sex". I was buzzed and really confused but just said 'okay.' Then she said..."but there was one night at a club in vero beach that i've never told you about. I know we role play a lot but this is the real thing...i'm so turned on right now and want to tell you what happened on the dancefloor."