Carrie's Sailing Trip: The Start

Introduction:

Hi my name is Carrie and this is a story about a trip I took a little while back now with my boyfriend Bob and best friend Lisa and her boyfriend Brad. It was a fantastically wild and refreshing week sailing around the Virgin Islands in the Caribbean. I was down there a couple of years ago with a bunch of friends from college, but it was a little different this time with my boyfriend along.

Let me give you a little background before jumping into the exciting parts. This friend of the family has a sailboat that he now keeps in the Caribbean. I used to help him sail it from race to race. He felt comfortable with me at the helm enough that he offers to let me use it in exchange for looking in on it and fixing things up. Now that’s the kind of friend to have.

The trip consisted of my boyfriend Bob who is a powerboater, so he likes boats just not sailboats. He always says there’s too much work to go slow. I’ve tried to convert him and he is coming along, however he is still a motor boater at heart. He’s about 6’2” and weighs about 230. He’s really athletic and drags me along with him on all his crazy activities. My best friend Lisa, who was my roommate in college, was also along with her boyfriend. Lisa and I are still really close despite living in separate states now. She’s always getting me in trouble doing crazy things that I probably shouldn’t, but I still love her dearly. She is about 5’5”with long dark hair. She weighs about 135 with a 32-24-34 figure. This became a couples trip when she when her boyfriend Brad joined us. He is about 6 foot and probably weighs around 200 or so.

In case you haven’t read any of my other adventures, I’m 24 with blonde hair, which I now have cut back a bit and permed into this sassy look so I don’t have to worry about it. It really looks cool and I don’t have to fuss with it much, which was great. I’m on the tall side at 5’9” and weigh 128 with a 34C-22-32 figure.

In case you don’t already know, I guess I’m a bit of an exhibitionist even though I never would have thought so just a couple of years ago. I get really excited and love that aroused feeling I get when doing something sexy and daring. I used to get so nervous that I’d almost get sick, but lately I’ve found that I don’t get near as nervous. The problem is I also don’t get as much excitement, so lately I’ve been doing things that I never would have considered before.

Ok enough babble, on to the trip. . .

Carrie’s Sailing Adventure - Getting there

Lisa and Brad drove up the day before and Lisa helped me pack. Lisa remembered our trip to the Caribbean where the airlines lost my luggage. Having almost nothing to wear all of that week was the beginning of my exhibitionist experiences. Ever since, Lisa has been daring and challenging me to do more and more daring things.

A couple of weeks prior, we had been talking about this email a friend of mine named Faith had sent about a trip she took to Mexico. She didn’t bring a single bikini top or bra. Every time she went to the beach or hotel pool, she was topless or completely naked. In the back of my head, I wanted to do the same but I remembered being told that it isn’t exactly permitted in the Virgin Islands even though it wasn’t enforced very often.

Also, the last time Bob and I had gone away he gave me a hard time about how much I brought, so this time I was determined to show him up by packing extremely light.

Lisa convinced me that I didn’t need much more than my bikinis except for some going out clothes, so that was just about all I packed. I packed 3 of my tiniest bikini, a couple of hot tee shirts and tank tops, a couple of sexy shorts including one I purchased from Wicked Weasel, and a short dress incase we went someplace fancy. I didn’t pack a single piece of underwear. No bras or panties what so ever, which was going to make wearing my little party dress interesting. We packed a couple of other goodies that I’ll get into later. My entire week’s contents fit in my small GYM bag that I planed to carry onto the plane.

None of us slept very well that night and woke up early anxious to get on with our trip. Lisa was already up and showered as I rolled out of bed. She suggested that we dress for the islands even through it was 50 degrees outside. I pulled on this pair comfy denim shorts. I like them because they’re really soft and comfortable for denim. They’re not the lowest hip hugger shorts in the world, but they are pretty small so there isn’t exactly a lot to them. They were pretty loose so I was a little concerned that you could see up the leg opening since I wasn’t wearing panties but figured why not.

I must be really getting daring because for a top, I picked this half-shirt top that barely reached the bottom of my boobs. A year ago I would have never dared walk through an airport dressed like that. The top was really sexy because it just hung draped over my breasts leaving a huge gap between my ribs and the shirt. I don’t know why I rarely wore the shirt, because it felt cool like I was hardly wearing a top. Without a bra my breasts just floated around under the soft top.

I was already excited about going on vacation and the additional sensation of my nipples rubbing against the top was starting to show. The combination of the stimuli and the overall excitement of going on vacation were getting me quite aroused.

It wasn’t long before Bob arrived and it was apparent that neither he nor Brad seemed to mind my outfit. We all jumped in Bob’s Explorer and were off to the airport. We left our coats in the care and hoped it wasn’t to cold when we got back.

At the airport I was getting more attention than I had anticipated or really wanted as heads turned to check out my outfit. The motion of my breasts not to mention my nipple poking at my brief top made it obvious to everyone that looked that I had nothing on under it. Going through the security check point was kind of interesting. As I put my bag on the x-ray machine Bob whispered over that he hoped I didn’t get strip-searched. To which Lisa giggled and said, “It wouldn’t take long that’s for sure.” I took all the metal out of my pockets but somehow just knew I was going to get stopped. And sure enough with a great smile, the guard asked me to step to the side.

One guard went through my carry which caused me to start blushing from embarrassment as he went through my sexy clothes. The other asked me to spread my legs and stretch my arms to the side. It seemed rather silly to wand my legs and arms since they were bare, but he did it anyway. Must be some stupid regulation. I could see the others laughing as my embarrassment grew. I had to be careful as I raised my arms so as not to expose my breasts under the short top. It was kind of funny being searched when there was virtually no place to actually hide anything. I tried not to laugh knowing the whole time that my breasts were threatening to make and appearance. Finally they were satisfied that I didn’t have any concealed weapons and we headed to the gate together.

The whole time we sat at the gate, Bob and the others made jokes about me being stopped. Lisa said I should have simple pulled the top and shorts off and save them all the trouble of searching for concealed weapons. Lisa suggested that I use a French accent once I got to the X-ray machine, take all my clothes off, and send them through the X-ray machine. I laughed at that one.

When we boarded the plane, I almost forgot what I was wearing when I went to put my bag in the overhead. I caught myself just in time and asked Bob to put my bag away. After we settled in, Bob and I had a little fun on the flight down, with him grabbing my breasts under my top whenever no one was looking. I think the people in front of us were getting a little annoyed, but it didn’t seem to stop Bob.

After a switch in Puerto Rico we arrived in St Thomas. We grabbed all our gear, all of which made it this time, sorry. Bob rented a car since we knew we were going to be in St Thomas for at least a couple of days.

Once we got to the boat we looked around and tried to figure out the sleeping arrangements. Lisa and Brad grabbed up the forward birth saying they’d leave us the rest of the boat. Bob and I decided to try squeezing into the aft bunk, which really was only designed for one person. We just threw our stuff down and proceeded to check out our home for the next week. Later, we went out to dinner and to this small club for a while.

We had more than enough to drink at diner so we were getting pretty silly. We were headed back to the boat when I suggested a walk on the beach. Lisa and Brad were running out of gas and headed back to the boat, but Bob and I went down to the small beach at the end of the marina. We walked along until the water came up to the hillside and you couldn’t go any further.

It was so beautiful and romantic that we sat down on the grass by the waters edge. It wasn’t long before we were kissing and making out. Bob already had his hands under my top and was working my boobs pretty good, so I decided to help him put and slipped my top over my head. We kissed and made out for at least a half an hour before deciding to head back to the boat.

Bob thought he’d make it a little more interesting for me by grabbing my top and walking off with it. When I caught up, he just put his arm around me and started playing with my nipples holding my shirt in his other hand. I complained that someone was going to see me but that didn’t seem to have any effect on him. However, the feeling of his finger caressing my breast certainly was having an effect on me.

He didn’t give me my top until we were just at the entrance to the marina.

We expected Lisa and Brad to be fast asleep or at lease taking advantage of our absence, but they were in the cabin in each others arms having another beer. Bob and I also grabbed a beer and we all talked for a while before deciding to call it a night at half past 2 in the morning.

Lisa and Brad retired up forward and Bob and I got ready to squeeze into our little nest back aft. I let Bob slip in first and then pulled my top over my head and wiggled out of my shorts leaving me completely naked to slide in next to Bob. I slid in over him practically poking him in the eyes with my hardened nipples. I can be such a tease sometimes, but Bob didn’t seem to mind from what I could tell. I slid down his bare chest and felt his penis poking me through his boxers as I slid over him to the other side of the bunk. I was still really horny so we fooled around for a bit. I was lost in the passion of one of Bob’s kisses when I felt his hand rub my now very swollen labia. I let out a noticeable moan as he worked his magic. I told Bob to stop, not wanting to let Lisa and Brad know we were messing around only a few feet from them, but Bob continued getting back at me for my teasing of him. After a couple of increasingly weak pleadings for Bob to stop, I simply rolled over. After that, I was lost in my own emotions. At first I tried to be quiet but by now I didn’t care who heard me as I felt my inevitable orgasm starting. Every muscle tightened as my orgasm hit. As my body settled down, I collapsed into Bob’s arms and we both fell asleep.

Carrie’s Sailing Adventure Day 2 - Getting Things Ship Shape.

The next day we woke to a light rain falling. Bob and I were still in our little nest behind the navigation console when Lisa and Brad made their appearance. Since we didn’t bother with a blanket or sheet or anything because of the heat, it wasn’t really possible for me to hide my naked body from their view. I guess I was having a rare touch of modesty, but there was little I could do at the moment. I half expected some comment about how much noise we had been making the night before, so I quickly suggested a trip to the marina shower to see if Lisa was mad as me for being naked in front of her boyfriend.

Lisa didn’t seem upset at our antics when she suggested just stepping out and showering in the rain. I didn’t wait for Bob to get up and slid back across him rubbing almost the whole length of my body against his face as I did. I then quickly picked up a nearby towel and wrapped my bare body in it, tucking it in tight around my breasts. I then picked up my bag and headed for the ladies room. Lisa was fine with everything and even dared me to walk back from the shower to the boat naked since it was raining even harder when we finished up and I hadn’t brought any rain gear from the boat. I told her maybe sometime but for now so I put on my white bikini.

We walked back to the boat with me in my bikini, which was in stark contract to Lisa in her rain jacket. I don’t know what it is, but I really get off on the exhilaration from the coolness of a light breeze blowing across my bare skin. I did pull on a pair of shorts for our trip to breakfast but that was it, figuring I would dry out faster than my clothes would. The rest of the day was spent getting the boat ready. We had to made several trips to the local marine store trying to fix a problem with the lights on the boat. We did take a break in the afternoon to go for a swim when the rain ended.

That night at dinner, I wore a sexy tank top with a pair of shorts. This top while reaching almost to my navel, left half of my breasts exposed over the top of the material. Without a bra anyone looking would have a clear view down my chest if I bent over at all. It was no wonder the waiter paid particular attention to our table. It didn’t seem long after we sat down that the subject of dares came up. Lisa brought up this Luck of the Draw dare that I had told her about and she brought up that I was going to try to repeat it this week. The dare basically had me drawing 10 cards, one every 10 minutes. The numbered cards were no problem but the face cards all involved me doing something. Lucky we weren’t prepared to do it them.

Lisa kept talking about various dares I had done. Bob had heard most of them before but Brad seemed to be getting into it and kept asking what else I’ve done. The whole time I was getting more and more embarrassed. The place wasn’t that crowded but I know people around us were listening in. By the time we left I’m sure they thought I was some kind of nut.

That night back at the boat was pretty uneventful except for me teasing Bob again as I slipped in along side him naked. We fooled around again before falling asleep.

To be continued