Carries Vacation Adventure Day 1

My one friend Lisa who is my roommate and two others, Barbara and Jane, who where actually more Lisa’s friends than mine went to the Caribbean over winter break. Lisa and I were only invited when two of Barbara's friends bailed out at the last minute. I don't think Barbara actually wanted me to come since she seems to view me as a rival. I don't know why since she is quite good looking and never has any trouble with the guys. She has dirty blond hair and is about 5, 5 and probably weighs about 130 to 135. She has an average chest and nice figure. Let me describe the others while I'm at it. Jane is a little shorter with dark hair. She probably weighs around 120 pound but has a much smaller chest than Barbara. Lisa, my roommate, is 5, 5 with long dark hair. She weighs 130 with a 32, 26, 32 figure, very athletic like myself. I have blonde hair and am on the tall side at 5 9. I weigh 125 and have a 36c 24, 34 figure.

Lisa and I met freshman year on the swim team. Don't get me wrong, I love Lisa. We do everything together, but she's always getting me in trouble. Some times on purpose I think. She always gets me started and like a fool I carry through and do something I shouldn't. Well back to the trip. Because Lisa and I made our plans at the last minute we were on a different plane than Barbara and Jane. Their flight was first thing in the morning while Lisa and I were on a late morning flight with a change in Miami. Everything went well until we arrived and I couldn't find my bag.

Well after an hour or so the airline put a trace on it and told me they'd deliver it when it arrived. Barbara and Jane had already left for the resort so we grabbed a cab when we were done. Boy was it hot. Usually you have a nice breeze, but not that day. By the time we got to the resort we were both soaked thanks to our un-air conditioned cab. We ran into Barbara and Jane just as they were headed down to the beach to look around. The room had one bedroom that Barbara and Jane had already moved into and a nice eat-in kitchen. It looked like Lisa and I were living on the pull out bed in the living room area. Not that bad though compared to some arrangements I've had.

Lisa and I needed a shower before heading out thanks to our cab ride. Lisa showered first and had already changed into her shorts and tee shirt when I finished and came out with a towel wrapped around me. Now for the first of what would turn out to be a continuing problem. What to wear? With the airline loosing my bag, the only clothes I had were my jeans and long sleeve shirt, which were soaked. Lisa offered one of her tee shirts but being a little larger up top I couldn't fit it over my breasts. I tied several of her shirts including her bikini top with the same results. Lisa said, "Why don't we just head down to the beach. You don't need anything there."

"Ha ha" I said. I was going to try one of Barbara's shirts but I didn't want to get on her bad side. I decided to call the airline to see if my bag had come in on the next flight. Standing there in only a towel, Barbara and Jane walked in with these two guys they had just met. I explained what had happened and Barbara and Jane just laughed. The guys didn't seem to mind. They echoed Lisa's earlier comments saying you can go nude down here. There I am on the phone trying to communicate with this guy from the airline that I can barely understand me dressed only in a towel with a room full of people telling me that I don't need any cloths down here. "Lots of women go topless and naked," they said. While waiting on hold, Barbara offered me one of her dresses saying, " I hope it fits," as the gang walked out the door. Eventually I gave up and hung up the phone. Lisa said that the others were heading out to a night club and for us to meet them there later.

I tried on the dress Barbara had left me. It was a nice black mini dress that fit pretty well except for two problems. Remember I'm a couple inches taller than Barbara so the dress didn't quite make it to mid thigh on me. That wasn't that bad, I had worn really short skirts before. The real problem was that the dress was suppose to have those optional clip-on shoulder straps, but they were nowhere to be found. Lucky my breasts are a little bigger than Barbara's and it looked liked like the dress would stay up without the straps. At least that's what Lisa kept telling me.

There she goes again getting me into trouble. Lisa loaned me a set of her thong panties, which I wore under the dress. A bra wasn't possible with this outfit. By now it was dark and Lisa had changed into a nicer shorts outfit for going out later. Well we decided to walk around and see the place before getting something to eat. After walking down to the beach area I decided that walking wasn't what this outfit was made for. Well my breasts were holding the dress up but just barely. I had to keep pulling it up to keep it in place. I couldn't pull it up too far through; there wasn't much covering my butt. Lisa made some comment that the towel probably covered more. I responded by saying that it probably would stay on better as well.

We wondered around for a little more until we came across this nice restaurant in the resort. We had a nice dinner and several drinks. By the time we finished we weren't feeling much pain. I didn't really want to go to the nightclub but Lisa insisted; so we took a cab to the place. Turns out it was only about a mile away. Probably could have walked it. We went inside and found Barbara and Jane at a table in the back. When Barbara saw me in her dress her mouth dropped. She said, "I know you have bigger boobs than me but you still could have worn the straps. You don't need to flaunt them at me."

I said, "If I could have found them I would have put them on."

Then Barbara said, "Well, I hope it stays on."

We had all had a drink and talked about what we should do tomorrow. Lisa suggested the beach saying that "unless the airline finds her bag that's the only place Carrie will be able to go." I said, " Not that I have anything against nudity, I just don't want to be the only one." Everyone said, "There will be plenty of naked people at the beach." I said, "I was referring to you guys." Barbara said, "we don't have to, we all have bathing suites." Lisa said " don't worry, think of the tan you'll get." After a while those same guys that Barbara and Lisa had met earlier came by and asked us to dance. Barbara and Jane joined them; I was still concerned about my dress falling down. Lisa ordered me another drink for us, saying, "have a couple more and you won't care."

Then these other two guys came by and asked Lisa and I to dance. I said no, but they insisted, almost dragging me up to the dance floor. The guys were really nice. The guy I was dancing with was Bob and the guy dancing with Lisa was Mike. It was fun but I had to keep adjusting the dress every time it slipped down. Somehow it stayed on however. Then the band started to play a really fast song and I knew I couldn't dance to that without risking exposing myself to everyone there. A couple of times Lisa looked over to see how I was making out. I just kept pulling it back up when it started to show too much. I know Bob saw the problems I was having but I'm sure he was hoping it would fall. The song was just about to end and I started to relax a little. I must have reached a little to high.

Out sprang my breasts for everyone to see. I almost fell over trying to catch the dress before it went over my hips. I pulled it up as quickly as I could but not before the crowd got an eye full. We went back to the table and Lisa just started laughing. Well that was it for dancing for a while. Barbara, Jane and the guys left for a walk on the beach. We said we'd get a ride back or take a cab. After a while Bob and Steve had to leave saying they had to be up early for a dive trip they had signed up for. They said they'd look for us on the beach in the afternoon. Lisa shouted "We shouldn't be hard to find that Carrie will be the naked one," telling them and everyone around us that I had lost my bag and didn't have a bikini to wear." The guys hearing that stayed around for a little longer saying maybe they'd skip the diving. Eventually they left and Lisa and I danced together. This time a little more cautiously though.

When we left we ran into these two girls that were on the flight down with us. They said if you cut though on this trail, it was only a 15-minute walk. I protested saying that, " the dress I had wasn't made for hiking." The girls convinced us despite my better judgment. It seemed I was holding everyone up since I couldn't walk very fast and not have the dress fall off. I complained that they should slow down. Luckily I had on some low cut shoes so my feet were ok. The girls were telling us all about their place and that we had to come down and see the view.

I wasn't really paying attention. I had holding the dress up on my mind. They complemented me on how nice I looked, saying they admired how daring I was to wear a dress like that. Lisa went on to tell than that the airline lost my bag and that I had borrowed the dress. I told them that I don't know what I'm going to do tomorrow since I didn't even have a bikini to wear. They offered to help but they could see that neither of them had anything that would fit me either. After what seem like a half an hour I said "shouldn't we be there by now."

The girls said it shouldn't be much further, saying they had walked to the club this same way. I asked to stop for a bit saying, "My arm was getting tired holding this dress up." Saying that the dress was a real pain. We started walking again when Lisa said, "If the dress is that much of a problem why don't you just take it off. There's no one out here but us girls." I thought about it and after a while reached for the hem and pulled it up over my head. The girls we were walking with just stopped dead in their tracks. I apologized for shocking them but said, "I couldn't stand this dress any more."

Well there I was standing there in just my thong bikini panties holding the dress. They said, "What happens if someone comes along"? I said, "Well we haven't seen anyone so far and besides its legal down here anyway." We started walking again and I had to admit it felt better. The cool air felt good, there weren't any bugs, and besides I didn't have to worry about that dress any more. The girls said something about my tan and lack of tan lines, but I tried to ignore it. Then Lisa started to comment on my breast and stomach. I tried to change the subject but Lisa was the troublemaker.

I said, "don't we have anything else we could talk about besides my body?" Lisa said, "under the circumstances it’s an obvious topic" and just continued the conversation. Then it happened. Around the corner came a guy and a girl walking towards us. At that point there wasn't anything I could do. They had both seen me and obviously noticed that except for my bikini panties, I was naked. The girl was first to comment asking if I was hot. When I explained she seemed to be more sympathetic. Her boyfriend just stared at my breasts.

I was going to put the dress back on when she asked where we were going. They said we had passed the turn and we had to go back about a half a mile. They said they'd show us. I figured what the heck they had seen all there was to see by then and I really hated to have to put that dress back on. They showed us where we should have turned and we parted ways. I caught the guy turning around as we left. She said something to him but I couldn't make it out. We walked on a little further talking about what we should see while we're here and I guess I got caught up in the conversation because I had totally forgotten that I was still carrying the dress in my arm.

We had come to the small road that separated the hotel from the trail when one of the girls said, "aren't you at least going to put the dress back on to go through the hotel or are you going to just walk in there naked." I said to her "so what if I do." She said, "I dare you." Well I may have still been a little tipsy despite the walk but I wasn't about to walk through the hotel naked. I pulled the dress over my head just as the lights from a cab came around the driveway. The girls asked us if we wanted to walk down to the beach with them but I had had enough of walking in that dress. We headed up to see if my bags had come. Lisa asked me what I was going to do if they still hadn't arrived by tomorrow. I joked and said, "Maybe just grin and bare it." I said, "Someone has to have something I can wear."

We had no sooner gotten back to the room than Barbara and Jane walked in. They said the walk on the beach was nice but the guys were jerks. We told them that we had walked back and got lost. I left out the part about walking most of the way topless. Needless to say my bag wasn't there. Everyone was tired so we got ready for bed. Barbara and Jane had the lone bedroom so Lisa and I pulled pull the bed out from the couch. Lisa was already in bed when I returned from the bathroom. I don't normally sleep in the raw, but under the circumstances I didn't have much choice. I slipped the dress and panties off hanging the dress over the back of the chair. I told Lisa she shouldn't get any ideas. We talked for a while when Jane came out asking if anyone was hungry. She had on a tee shirt and light sleep shorts.

Lisa said she was thirsty and asked Jane for a soda. Jane brought us both sodas and we talked for while she made a sandwich. Barbara came out a minute later in a tee shirt and panties. She and Jane both had a beer and sat down on the chair next to our bed. I sat up holding the sheet to my chest to hide my breast. I guess Barbara didn't realize I was naked under the sheets based on her shocked expression when I sat up. We talked for about a half an hour on what we were going to do the next day.

It seemed like a beach day on all accounts. Jane then offered me the use of an old bikini she used to use for tanning. She explained that it was kind of small but it was a string bikini so I could adjust it any way I needed. I couldn't help but think that if it was small on her what was it going to be like on me. Again Lisa said, "what do you need a suit for down here." All I could hope for was that my bags arrived in the morning, otherwise it was going to be an interesting day.

To be Continued with day 2