Carrie's Sailing Trip: Day 5

Day 5 - Back to Port

It cooled down over night and we both woke up just before dawn to move down below to stay warm until Lisa and Brad woke up. We didn’t exactly go back to sleep though. Bob had another one of his romantic moments and started to get me all worked up as only he can do. Before long, I felt an orgasm building and was lost in bliss. Not a bad start to the morning at all. Bob said, “See what you miss when you sleep in.”

I don’t know whether our messing around woke Lisa and Brad up, but I was still enjoying my morning bliss when Lisa and Brad got up. There certainly isn’t any privacy on a boat that’s for sure.

For some reason I was feeling terribly under dressed all at once laying there naked, so I got up and wrapped myself in a towel while we got organized and got breakfast. We decided that we had to find a marina tonight since we were running out of supplies. Actually the only thing we were totally out of was beer, but that was probably the most critical item to the guys.

I wasn’t planning on staying naked, but the gang insisted I stay that way until we reached the marina or at least until we ran into more people. So I stayed naked while we pulled anchor and got underway. I had sailed many times before in my bikini, but this was the first time I had ever sailed completely naked. God, if the old crew could see me now.

The rest of the morning and early afternoon was pretty un-eventful. I got things going then let Bob and Brad take charge as Lisa and I laid out up front. I guess a couple boats passed close enough to get an eye full, but overall we didn’t see many boats until we passed close to Tortola.

I should have probably gone below and put on my bikini, but I just rolled over onto my stomach. Unless they passed right along side, they probably would have thought that I just had on a skimpy bikini.

When we did get close, Bob asked me where we were supposed to turn in and asked me for some help. I don’t know whether he planned it that way or not, but he waited till a couple of boats were sailing nearby heading into West End Harbor. I didn’t want Bob to run us aground or anything, but I also didn’t want to everyone to see that I was naked. Figuring the consequence of running aground was worse than being seen naked, I quietly got up and made my way back. On the way, I ducked into the cabin and grabbed my towel.

I confirmed where we were with Bob telling him, “I guess it’s finally time to get dressed.” There was a big boo from both guys as I ducked below to look for my bikini that I had not worn in almost two days. That was the longest period I had ever gone without putting something on.

When I came back up on deck Lisa said, “Bummer. You’re going to ruin that perfect tan.”

I said, “oh well, I guess if the guys didn’t need their beer so badly I could have continued.”

Well to jump ahead, we found the marina and tied up without incident and after a short wait at customs, the guys went about getting some supplies, i.e., more Carib beer and munchies. Lisa and I were stuck cleaning the boat. We did have a little fun hosing things off as we got into a pretty good water fight with the hose. I was on the receiving end until I wrestled the hose away from her and pushed her over the side. When I finally helped her out we looked around and found we had an audience watching from other boats.

Sorry guy, no clothes were torn off.

When the boys got back, we had a couple of beers still in our bikinis while we figured out what we were doing. Eventually we got hungry and decided to get showered up and dressed to go out.

Lisa and I grabbed our bags and headed of to the marina shower. We had already had a couple of beers on an empty stomach, so we were already kind of buzzed. I couldn’t decide what to wear so Lisa made some suggestions of course. We all felt like getting out and having some fun after being on the boat for 2 straight days, but were all so relaxed that we didn’t feel like going to far.

It was still pretty hot so I wanted to dress light. Lisa suggested wearing just my bikini, but I felt like I need a little more than that. I picked out my white wicked weasel shorts that I had only worn a couple of times in the past.

Talk about hot. These shorts are the ultimate in sexy. There short, thin and tight. They certainly weren’t your average pair of shorts. I pulled them up my legs and literally stretched them over my hip. After that I reached my fingers under the edges and stretched the tight material out as best I could. They sit a lot higher on my hips than a lot of the short I have but they probably are the shortest. I don’t have much in the way of butt cheeks, but I felt like half my ass was hanging out no mater what I did. The front has the sexiest V cut which shows off my stomach really well, and below that my labia is clearly outlined by the tight material.

I did a little spin for Lisa who couldn’t get over how good they looked on me especially with my tan that was really starting to come in. She said “You look really hot especially if that’s all your wearing?”

I laughed and said, “Don’t be silly” as I searched my bag for just the right top. I decided on this loose fitting tank top to balance out my tight shorts. It also showed off a generous amount of flesh perhaps a little too much since I didn’t have a bra to wear under it.

We finished our hair and makeup and headed back to the boat to pick up the guys. Bob gave me a whistle as I came aboard.

We ended up at this quiet restaurant right near the marina, so we didn’t have that far to walk. The waiter did a double take as we came in smiling as he checked out my outfit. He couldn’t help but stare down my top as he took our drink orders. That’s when Lisa got up and went over say something the bar tender. I didn’t think anything of it at the time but found out the next day that she had asked to bartender to mix mine extra strong since it was my birthday, which it wasn’t.

We had several more drinks as we ate, thanks to the waiter’s attentive service. I wonder why. Soon we found that the place had pretty much emptied out except for a couple of tables and some people at the bar. About a half hour later, the waiter comes out with a birthday cake and everyone starts singing happy birthday to me. Now I’m trying to explain that it isn’t my birthday, but no one is listening. Then the bartender comes over with a round of shot glasses. We all downed our shots like I really needed anything else to drink.

I can usually keep up with the best of them, but by then I was pretty drunk. We were all pretty silly and loud and I was feeling no pain. Bob had been stroking my thigh for quite a while and I was getting pretty mushy and tuned on which was evident by the way my nipples were poking against my thin top.

Lisa interrupted our making out when she pulled out a deck of cards and dared me to play that luck of the draw game that I had told her about. This woman had dared me to play this card game where depending on the card I drew I had to do certain things. The original dare had me draw a card every 10 minutes. If I pulled a numbered card, no problem, but if I drew a face card it got interesting. The jack and queen had to do with wearing a skirt so Lisa suggested an alternative around going topless at the beach for the Jack and naked for the Queen. Considering the fact that I was drunk and it was at the beach I agreed.

The king was even worse. Lisa had brought Karen’s vibrator along and I was to put it in, on high under my shorts, till I drew the next card. The aces were really interesting cards. Each ace originally represented a different article of clothes, but since I only had two articles of clothing on, we came up with some alternate rules. For both the ace of clubs and diamonds I had to take off my top right there at the table. For the Ace of hearts I had to take off my shorts. For the ace of spades, I had to strip completely.

I told them I couldn’t just strip in the middle of the restaurant, but they had all ganged up on me. By then I was pretty turned on from Bobs attention not to mention from being drunk from the booze, so I stupidly agreed not really thinking through what could happen not that I could really think clearly any more.

Lisa pulled the vibrator out from her purse and made sure it worked which raised the curiosity of the guys. That kind of sobered me up, but not to the point that I stopped the game.

By then some others that had been hanging around got interested and came over which only added to our silliness. Lisa put the deck down and I stared at it for a second as I worked up the nerve to turn over the first cards. I told them I was only drawing 5 cards.

The first was a seven of clubs so I was safe. We all looked at each other and someone said go ahead and pick another. I complained that I still had 10 minutes but they convinced me to get it over with. Well 10 minutes had probably passed by the time we stopped arguing, so I begrudgingly picked the next card.

I turned over the next cards and it was a two of clubs. Again I breathed a sigh of relief.

I had been lucky so far, but the odds went up as I drew more cards. And that’s exactly what happened as I drew the jack of spades. But even that wasn’t that bad since I didn’t affect me immediately and I would probably gone topless anyway. My 4th card was the dreaded king of hearts.

My head slumped onto the table as I told everyone I couldn’t do it. Lisa complained saying that I had done it when I was with Karen and Sue, so why not now. I was bombarded with comments, but the one that ticked me off was when they called me chicken and started making fun of me.

I think a couple of them expected me to just pull down my shorts and slide it in right there at the table, but I wasn’t about to do that. Eventually after I couldn’t take it anymore, I grabbed the vibrator from Lisa and got up to got to the ladies room. She immediately got up to come with me. I think to make sure I didn’t cheat even though she said it was to make sure I was alright.

In the bathroom I started to plead with Lisa, but then I got pissed and just figured I’d show her. I pulled my shorts down my legs and she handed me the vibrator already running on high. I stuck it under the sink to warm it up and lubricate it and started to slide it up my vagina. I let out a noticeable moan it touch my pussy. I was already pretty wet so it slid in easily bout Oh My God What a sensation!

I had to wait a second to get use to it before pulling my shorts back in place. I had only just put it in and already it was having its effect. I was pretty tipsy and my inhibitions, what few I had, were pretty much gone but this was a whole new sensation. I stood there trying to collect myself but found that the long I stood still the worse it got.

Lisa leaned over and held my arm asking, “Are you alright?” I just looked her and whispered, “Oh my God, I can’t think straight.” Lisa said, “I don’t thing the idea is for you to just hang out her in the bathroom for the entire 10 minutes.”

I was succeeding at maintaining a level of control over my emotions, so I agreed to go back to the table. As I took those first couple of steps I realized that the process of walking was actually helping take mind off the sensation in my sex, despite the weird feeling of the vibrator moving around inside of me.

I was already feeling all warm and clammy as I go back to the table. I looked over at Bob and told him, “You’d had better be ready tonight.” To which he responded, “Ok well I guess its time to go everyone, See you back at the boat.” No one laughed at Bob’s attempt at humor.

I sat down and immediately felt the vibrator move inside me. Everyone one was laughing and talking as I tried to maintain control. Bob put his arm around me as I sat there. It was obvious by my glazed eyes and rock hard nipples that I was aroused. Everyone was waiting to see what happened next.

I was determined to maintain control. I tried to think of everything but sex but everything came back to that. It’s funny how the mid plays tricks on you. Beads of perspiration were forming on my forehead as I waited for my 10 minutes to be over.

As time came, I went to get up and remove my source of torment, but someone suggested picking the next card in case it was another King. I picked up the next card immediately wanting to get this over as quick as possible. It was another Jack so I got up and all but ran to the bathroom. As I did I relaxed a bit and immediately felt the unmistakable feelings of and upcoming orgasm building quickly.

I ran inside the ladies room and braced myself up against the sink. Luckily there was no one there because there was no controlling my body release. I was just coming down when the door opened. I turned to see Lisa, asking if I was alright. I nodded my head unable to speak.

Once I stopped climaxing, I ducked in one of the stalls and gently remove the vibrator from my wet pussy. I cleaned myself up as best I could but the smell of sex was impossible to miss.

I splashed water in my face and looked at myself in the mirror as my face returned to its normal color. Actually the release was exactly what my body needed because after I felt like a new woman. More relaxed and even more sober. I freshened up a little more before returning to the table.

The group surrounding out table had grown even more or perhaps I just didn’t notice them previously. I had barely sat down when someone handed me another shot class and suggested strip poker next. I raised my glass to a toast to my success and firmly said I was done with dares for the night.

Bob once again got real romantic until I told him that he had missed his chance. I told him, “who needs a man when she has a vibe.” That kind of surprised him and knocked the wind out of his sails. I couldn’t be that mean, so I reached over and gave him big wet kiss on the lips right there in front of everyone looking on. I was starting to get into it when I felt his hand grab my breast under my shirt.

I had enough to drink and the crowd slowly started to disperse when they realized the show was over. We paid our bill which was enough to shock us back into sobriety and we all staggered back to the boat. I was staggering pretty good but no worse than Lisa. I barely remember taking off my clothes and going to bed. The next thing I remember was waking up naked in Bob’s arms in our little nest behind the nav station.

To be continued