When I stationed back east about 10 years ago I worked with a young woman named Laura. She had spent some time working before going to college and was in her late 20s when she started working for us. Laura made a striking first impression, with long dark hair, dark eyes, pretty face and great smile. But what was really impressive was her figure. She was fairly short at just over five feet tall with a great ass and huge tits. Her tits were a full D cup and still quite firm.
When she first started working with us, she would often wear short skirts and tight low cut tops that showed a lot of cleavage. We found out later that these were outfits she wore out to clubs, but she didn't have any other clothes for a while. All the guys were disappointed when she swapped her clothes for more professional attire after a few weeks.
We also found out later that she has work at hooters for a few years after high school to earn money for college and I remember often fantasizing about her in a hooters outfit :-) Her low blouses were particularly distracting to me and she caught me staring at her gorgeous tits on a few occasions. She would always just smile and keep the conversation professional. We did flirt with each other a bit, but nothing serious in the office.
After she had been there a few months, we got scheduled to go on a trip to San Diego together with our boss. Our boss ended up having to cancel at the last minute so it ended up being just the two of us on the trip. We flew into CA around dinner, so we stopped at a restaurant on the way to the hotel.
Laura had never been to CA before and was excited about the trip and getting to see the Pacific Ocean. During dinner, she mentioned wanting to swim in the ocean and that she had brought along a new swimsuit. I told her the ocean was too cold to swim in, but hopefully we'd have time to visit a beach on the last day of our meetings. I told her the hotel had a great pool that I used to swim laps when I was there. She liked to swim laps as well and said she'd come join me after we checked in. We decided to meet at the pool about 30 minutes after we checked in, so I got changed and headed down there.
I was very pleased to find the pool empty, so I jumped in and started to swim laps. I had been swimming about 15 mins when Laura came into the pool area. I stopped to chat as she took off the shorts and top she had over her swimsuit. To be honest, I was a bit disappointed to see the suit. It was a fairly conservative light yellow one piece. Her tits did look great in it and her nipples were sticking out a bit when she got in the water. She told me she had bought the suit to swim laps and was glad the hotel had such a nice pool.
I swam laps for about 15 more minutes with her then got out of the pool. She swam a bit longer then got out as well. As she was emerging from the pool I noticed the conservative swimsuit she was wearing had become very sheer when wet. The outline of her nipples were clearly visible through the suit as was a nice strip of dark pubic hair running up her crotch. The pubs were barely visible thru the suit, so it was somewhat lined in that area but the top didn't seem to have any lining at all and you could easily see the outline and color of her nipples.
Her areolas were huge...several inches wide and almost covering the entire top of her breast and two big nipples were poking out the middle of each. I had never seen areolas so big and could feel my cock getting hard looking at them. She came over to dry off and said the suit was great, but was disappointed in the material...she was looking down at her tits and could see how see through it was. I told her it looked great to me and she gave me a big smile.
She was sort of trying to cover herself with the towel, but didn't seem to be trying very hard to hide her tits and I caught her glance at the bulge in my shorts.
She said, "Well at least it covers a lot more than the thong my old boyfriend bought for me to wear."
"Did you ever wear it in public?" I asked.
She laugh and said, "I did a couple of times, but only after a couple of screw drivers."
"Did you like wearing it?" I immediately wished I hadn't right after it came out of my mouth.
To my surprises, she didn't seem to mind answering and said, "I didn't mind when there were only adults around but I was a bit uncomfortable around families with my naked ass exposed. I probably would have been more comfortable completely naked at a nude beach. At least everyone else would be naked with me."
She was standing with the towel wrapped around her waist as we talked, her big tits clearly visible to me and I could tell she had no problem with me staring at them.
I decided to take the flirting up a level. "You know, there is a nude beach just down the road from the hotel that I visited on my last trip out here."
I could tell that she was surprised I had been to a nude beach. "Did you go nude there?"
"Absolutely, it is a nude beach after all." I kind of chuckled. "I have been to a few of them, this was is great. You should try it sometime."
She smiled and said, "That would definitely take a few screw drivers."
I decided to press my luck a bit further. "I'm sure we can find a few of those for you and I'll even buy."
I still wasn't sure how she'd react to this new level of flight, but was presently surprised when she said, "OK, I might take you up on that...as they say what goes on TDY stays TDY right?"
"Yes, that is definitely true. It will be our little secret Laura."
We had meetings scheduled until the early afternoon the next day. I had a very difficult time focusing on the meeting topics, but did my best to make sure we stayed on schedule. Laura had on a very professional business suit that did a fairly good job at hiding her big tits, but I kept staring at them during in the meeting, thinking about how those big areolas were going to look naked.
She caught me staring at them a few times and gave me a knowing smile when we made eye contact. I could tell she was thinking about our plans as well and we both spent a lot of time ignoring the briefings.
The day finally ended and I asked her if she still wanted to go to the beach on our way back to the hotel.
She said, "Yes, but I am bit nervous. I have been thinking about it all day and will go if you're still buying."