This story was recalled when I was asked where was the most unusual/daring place I had ever had sex. Though I've had some really great sex in many different places, the following story has to be one of my favorites.
I used to live on a sailboat when I first got out of collage. Not real big, but she was nice. I've been an avid sailor my whole life so it was something I always wanted to do. Anyway, I had gone out on a date with a girl named Michelle a couple of times. We had done some pretty heavy necking in my car, but everything over the clothes to that point. On our third date she wore a light summer dress that really showed off her body. I'm not usually a legman, but she had great legs and a great butt. But what was killing me that night was she was not wearing a bra. And her nipples seemed hard all the time.
Anyway, after dinner we went for a walk down along the marina. Michelle new I lived on a boat but was deathly afraid of the water. I was really proud of my boat and wanted to show it to her, but it took some doing before she would walk down the floating dock to where my boat was moored. As we walked down the dock she had a death grip on my arm. I have to admit it felt nice having her push her body up so tight against mine. Now to get from the dock onto my boat you had to climb up two steps and then step across the water onto the boat. This is usually easy for any child over 8 years of age. However, Michelle was too scared to try. I had to physically pick her up and carry her across. This too was not all bad. As I lifted her up in my arms my hand cupped her right breast. It felt wonderfully soft through the thin material of her dress. Michelle was so scared that I don't think she even realized my hand was cupping her breast. Once she was in the cockpit of the boat she was feeling much more secure and relaxed quite a bit. As I recall, it was late summer and even down at the water is was a balmy night out. We sat in the cockpit and talked for a while. I then went down below and got a couple of cold beers for us. When I came back on deck Michelle had changed seats so she was now behind the Wheel. I handed her the beer and went and sat with my back against the cabin so I could face her. The wheel of my boat was very large in diameter and only cleared the floor of the cockpit by a couple of inches. Because of the design, it was very natural and comfortable to place your feet on the spokes of the wheel, which Michelle did in short order. This did however; bring her knees up and apart, lifting the hem of the dress temptingly up her thighs and exposing a lot of inner leg. I had left the cabin light on and the hatch open. Michelle was bathed in a soft warm light that was at a rather low angle and illuminated her legs beautifully.
We talked for some time, and I did my best to look her in the eyes, but couldn't help but try and sneak peaks of her whenever I thought I could get away with it. As the conversation went on we started talking about ourselves. Somehow it got on the subject of strange idiosyncrasy we each had. I told her how I had this strange habit that whenever I got dressed; I always put my socks on before anything else. I had to admit, I would sometimes look in the mirror and see myself naked except for a pair of socks and think I looked rather silly. We both laughed, then she told me that the only thing she could think of about her self was that she always (and she emphasized "always") had to wear matching bras and panties. Now, I had heard of other woman that liked to have their bras and panties match... but there was something about the way she emphasized the word always. OK, so I'm not always the sharpest knife in the drawer, but it suddenly hit me that she was very obviously not wearing a bra that night. Did that mean... Looking over at her I see this knowing little smile on her face. Oh man, I think I got a little dizzy the blood rushed so fast to my cock. She then spread her legs a little more, and with the light from the cabin I caught a glimpse of her shaved pussy. I think I heard a couple of the seams on my jeans pop.
Like I said, I may not be the sharpest knife in the drawer, but I'm not completely dull either. I quickly moved over next to her, and soon we were locked in a passionate kiss. Our tongues were like two fencers, parrying and thrusting, each looking for an advantage but enjoying the competition. As our tongue battle continued, my hands started to roam over her body. While my right hand moved up and down her back my left hand soon was rubbing and cupping her right breast. I felt her nipple stiffen through the thin material of her summer dress. I started to lightly pinch the nipple between my thumb and forefinger, drawing the fabric of her dress across her sensitive nubs. With this her tongue started to win the battle. Low moans began escaping from her throat and I was left defenseless. My hand soon migrated to her left breast and found the nipple already hard and waiting for my caress. By now my mouth had moved from hers and was kissing and nibbling on her neck and ear as the moans coming from her became louder.
I next moved my hand down her body and onto on to her exposed thigh. Slowly I started rubbing in small circles. Gently moving up her thigh, past the hem of her dress. Soon my hand was on the upper outside boundary of her thigh at the juncture where the thigh meets the hip. I so much wanted to slide my hand across and down into the sweet valley I knew was just inches from my fingertips. And I knew from the way she was squirming on her seat, Michelle wanted me too as well. But despite my longing to feel her wetness, and the fullness of her lips, I wanted to tease her a bit as I now knew she had done to me all evening with her sexy dress and no bra.
Wanting to take things up a notch, I remembered the hammock that I use on the foredeck when I go to Catalina. It is a simple hammock that attaches to the mast at one end and the forestay (a wire supporting the mast) at the other. It only takes about 2 minuets to hook up and I thought it could be a lot of fun. I slowly pulled away from Michelle who gave me a very puzzled look. I told her I had a surprise in store for her and that I would be right back. I ran up to the foredeck, pulled the hammock out the anchor locker, and had it up in record time. I then returned to the cockpit, took her hand and asked Michelle to come with me. When she realized we were leaving the safe confines of the cockpit I could see the hesitation on her face. I pulled her close to me and started kissing her again. I'm sure she could feel the swelling of my cock as it pushed against her stomach. As we kissed my hands ran down her back and started to knead her shapely ass. I was just about ready to forget the hammock, take her below and bend her over the chart table, when she pulled away from me and said.
"OK, but hold me tight"
"Like I would hold you any other way." I said with a big warm smile.