My Embarrassing Story

BY: Andrea

My name is Andrea and a friend finally encouraged me to write about and share an embarrassing but exciting story that happened to us last year during spring break. We were juniors at a large college in Texas and had a lot of close guy friends on the men’s baseball team. When the second semester began me and three of my friends from my sorority, Katie, Rachel, and Kim began dating four guys on the team. I was dating a guy named Teddy, Katie was dating Tim, and Rachel was dating Eric, and Kim was dating Mike. I think me and Katie were the best looking of us four girls. We both have blond hair and blue eyes and are both very thin and work out a lot. Although my chest is only 34b, I have gotten countless compliments at parties and at the gym on my butt and legs. We all knew each other from parties and stuff before we staring dating. Although we had all gotten to the point that we were monogamous, none of us had gotten too serious yet and we were all kinda just having fun. We were all going to Jamaica for spring break and we were all looking forward to it.

It all started with a bet we had with our boyfriends that they wouldn’t win their first two baseball games. We were at a party one night and we were all kinda drunk when Mike said, “I’m willing to bet you guys that we win the first two games.” Kim immediately took to the bait and said, “What did you have in mind?”

The words hung in the air for a second when Katie spoke up and said “Like what? Loser does the other person’s laundry for a month? I did that bet last year with you, it was great having my laundry done and all but I only needed it done twice and it was kinda lame.”

Mike said, “How bout losers have to go nude on the beach in Jamaica?” For a second I was in shock and my heart sped up. I was no prude and I wasn’t very shy but aside from skinny dipping at night once, I had never really been naked in public before. Rachel answered back, “Do you mean fully nude, for like an hour or so?” Mike replied, “Yeah fully nude for at least an hour.” I spoke up, “But wait, is it legal there to go fully nude? I heard of girls going topless there but not fully nude.” Tim chimed in, “No its legal, I read in an island pamphlet that the beach our hotel is on allows full nudity, and it even said so in the Hotel brochure.” We were all busy thinking about when the guys all started saying they agreed to the bet since they were so sure they were going to win. Rachel and Kim immediately said they were in. I thought for a moment what it would be like to see Tim, Mike and Teddy fully naked on the beach. Although I was very into Teddy at the time, I had seen the other guys without their shirts on many times and they were all very built and ripped, Tim especially. The thought of seeing their naked asses and dicks on the beach for an hour made me kind of excited and I think I turned a little red. Without daring to think what it would be like if we lost, I added that I was in. Katie held out for awhile, but finally she reluctantly agreed.

They won their first game and we were all scared about having to follow through and pay up on the bet when Rachel said, “I got us into this mess, I’ve got an idea to get us out.” “What’s that?” I said. Rachel said, “How bout we propose like a double or nothing. If they lose next week, the deal is off, and all is even.” “What if they win?” Kim said with a smile? We all agreed to suggest it to them and see what they wanted in return for the bet. After all, it couldn’t really get much worse for us could it?

STRIP DARES & HOT GAMES

We told the guys of our proposal they pondered it for a minute when Tim said, “Ok how bout if we lose, all is even steven, and nobody has to get naked on the beach, but if we win, you guys have to stay naked for an entire 24 hour period in Jamaica.” I think we all froze for a second. It was one thing to be naked for a little while it was quite another to have to stay naked for a full day. “Rachel answered back immediately, “What do you mean? We can’t stay naked at night and stuff. What are we supposed to be naked in the hotel?” Teddy said, you can stay on the beach the whole time if you like, I am sure there are bathrooms and you can get food there, plus I bet you can walk through the lobby for a second to the elevators or stairs to go to the room.” I said “I doubt we can do that guys, we would get kicked out.” I was surprised Teddy was so accepting to the idea of his friends seeing me naked for a whole day. Tim said “Ok you would have to be naked for 24 hours, but if you have to put a towel on for a minute or two to go from the beach to the hotel room then you can, but only if they don’t allow it. “Deal?” “What about later at night,” Rachel said. “Are we supposed to not go out?” Tim said “We can hang out in one of our rooms and drink there. Is it a deal?”

We all thought about if for a while. Katie said, “Listen guys, I have to think about this, can we talk alone and let you know?” Mike said, “You guys have five minutes to decide, if you choose not to accept it, we are going to see you buck naked anyway!” That drew more high fives from the guys and got me more mad at Teddy.

We moved away and spoke about if for a few minutes. Katie was the only one who was really nervous. I told her look at it this way, if we don’t accept we already lost and you are going to have to go nude anyway right, so with the new bet at least you have a chance that you won’t have to do it at all. If we lose again, big deal, how bad can it be, they will see us naked on the beach for a bit and we will hang out and eat in our rooms and stuff. They will get bored with it after a few hours anyway trust me.” Little did I know how wrong I was.

The second game was a few days later and we were all really nervous. It turns out the best player on the other team got hurt and our guys creamed them. It wasn’t even close. Over the next few weeks me and Katie worked out almost everyday so that we would at least be in shape for the trip.

When we finally got down to Jamaica and were checking into our hotel, Mike asked the guy at the desk right away if the beach at the hotel allowed for full nudity. The guy looked at me and Katie and answered yes with a smile. Mike asked about the lobby and the man said if you were going straight to the beach or back to your room and didn’t really hang around it was ok. We couldn’t believe our ears. Me and the girls were hoping that we would only have to be naked on the beach and in our rooms! The lobby was a whole different ball game.

We decided that we would go nude on our third day there. That way we could at least check out the scene and get tan a little at least so we could look better. The guys said that we could pick the time of day we would start. The girls and I decided that 12:00 noon would be good because we figured that would only leave us a few hours on the beach and then we would go to one of our rooms, avoiding a second day on the beach nude. We drank and partied for a few days, hung out on the beach and checked out the local bars. Our hotel was almost exclusively college kids on spring break just like us.

The big day finally came and me Katie, Rachel and Kim were all really nervous. Tim and Mike came to our room and said that they were heading down to the beach and that they would meet us down there. Before we went down, Teddy told me that I was being a good sport about the bet and that he wouldn’t think I was a slut or anything because of what I was going to do. He told me that it would be fun, and made me promise that no matter what happened, I wouldn’t have sex with any of his friends. I promised and we headed down.

Teddy and I walked out onto the beach just before noon and met the rest of our group. After we put our stuff down, Tim looked at his watch and said, “Ok ladies, its 12:00 noon, lets see some skin!!!” The moment of truth came. The four of us stood up on the beach. I looked around and saw hundreds of college guys and girls all over the place drinking and having fun. A lot of girls were topless or wearing thongs but only one or two women were fully nude, and they were older. I took off my t-shirt and shorts and slowly removed my bathing suit top. The other girls did the same. Teddy gave me a wink as I did it. I looked at the other guys and saw them staring back at my tits! It was such a rush and I turned bright red! I bent down and slid off my bikini bottoms and stood there, buck naked in front of everybody. As my friends did the same I noticed that almost everybody within eyesight had noticed that we had taken our bottoms off too and were looking over at us. As a joke I spun myself around letting our guy friends see my ass and back. They went nuts whistling and cheering. Tim took our clothes and put them in a bag and brought it back up to his room.

Teddy immediately asked if me and Katie could get him and the guys a drink from the bar. I shot him an evil look and looked at Katie. Although she had been the most nervous of us before, she seemed to be taking it situation well. We started walking across the beach, buck naked, toward the bar. Every guy on the beach had their eyes glued on us. They were staring at my pussy, tits, ass everything! When we got to the bar, the bartender smiled at us and said that more people should do what we were doing. A few guys came up to the bar right after us and stood next to us waiting to order drinks. It occurred to me that it was one thing to be naked on the beach and have people see you, but it is quite another when guys were standing right next to you while you were naked! I was shaking and nervous, but I started to get very excited by it. I felt my nipples get rock hard. The guy standing next to me definitely noticed and looked at me and gave me a smile.

We walked back to the guys with the drinks and sat down on our towels. It occurred to me then that we had to put suntan oil on or else we would burn. Me and Rachel had forgotten to put it on in the room so we had to do it there in front of everyone. I took out the bottle and starting putting the oil on. I noticed that Tim, Teddy, Mike and Eric were staring at me as I did it. I had no choice but to rub the oil into my tits as they sat there and drooled. I stood up and rubbed it on my ass which was awful because everyone on the beach was watching that as well. I got really mad when I looked over at Teddy and noticed that he was practically drooling as he watched Rachel rub oil into her chest.

We hung out on the beach the rest of the afternoon and I noticed that a few times our guys had to lay on their stomachs because they had gotten a little too excited. After a while in the sun we got really hot so Katie and I decided to go in the ocean for a bit to cool off. We had been drinking pina coladas all afternoon and by that time we were kinda used to being naked and even Katie seemed to lose her shyness. We told the gang we were going in the water and Katie and I headed for the water.

As we walked to the ocean a strange feeling came over me as we snaked our way around all the people laying out in the beach. I could see tons of guys in every direction staring at mine and Katie’s bodies. I got such a rush and started to feel really good. The water felt great. While we were swimming around two guys came over and started to talk to me and Katie. They were wrestlers from Ohio State University and were really cute and built. They asked us if we felt uncomfortable at all being naked. We told them about the bet and they laughed. After swimming with them for a while they asked us if we wanted to go up and get a drink with them at the bar. I looked over at our towels and saw that Teddy was rubbing suntan oil all over Kim’s stomach and chest. I thought that two can play this game. “Sure I said to the guys.”

Teddy and Mike didn’t even see me and Katie walk to the bar. They were both busy talking to Kim and Rachel and helping them with their suntan oil. Eric and Tim were off jetskiing. We sat at the bar with the Ohio State guys and had a drink. The whole time I couldn’t believe what I was doing. I was sitting there with two strangers having a drink buck naked. They weren’t shy about constantly looking us up and down either as we talked to them. One of them finally said, “Hey, you guys wanna do a tequila body shot?” I looked at Katie who seemed to be enjoying the whole thing as much as I was and said “Sure, what part of the body did you have in mind?” The guys looked at each other with a smile and said that it was up to us. One said, “How bout off of your chest?” I don’t know if it was that I was drunk of that they were both so cute, but before I could really think about it I said, “Sure why not.” I thought if Teddy can rub Kim’s chest, then certainly I could have some fun too right? I grabbed an ice cube and rubbed it on each of my nipples to get them wet and took some salt and rubbed it on. Katie did the same. The guys ordered 4 tequila shots. They each took a shot and turned to me and asked if I was ready. I nodded yes. At the same time the moved in and each put their mouths on my nipples. I couldn’t believe I was doing this because I had never even had a threesome before. They sucked on my nipples for about 5 seconds then did the shot and sucked on their limes. “Wow, that was great” one of them said. They turned to Katie who seemed really excited that she was next, and sucked the salt off of her chest also and did the shots. After a few more drinks we said goodbye to them and said that we hoped to see them later.

When we got back to the towels we found Kim and Rachel, both apparently very drunk sitting on Teddy’s and Mike’s backs giving them massages. When they saw us they stopped and the guys turned over. We could see from their shorts that they were both rock hard. They had obviously enjoyed having Kim and Rachel’s pussy’s rub against their backs. Teddy said, “Hey don’t be mad at us, we saw what you guys just did at the bar!” Katie and I looked at each other in shock. Before we could say anything else Teddy added, “Don’t worry, we aren’t mad are we Mike? As long as there is no sex you guys can do anything you want. And besides, we knew what we were all getting into with the bet and all.” He then reached over to Katie who was sitting right next to him and rubbed her pussy for a second. I thought she was going to slap him in disgust but to my surprise she just closed her eyes and smiled.

They sun was going down and Tim and Eric had come back from jetskiing and we decided to go back to our rooms. As we walked back Katie whispered to me, “I hope you aren’t mad at me. You can do whatever you like with Tim if that will make you feel better.” I said that I wasn’t mad and that I knew we were all just having fun. When we entered the lobby we headed straight for the elevators. I suddenly became very conscious of the fact that I was still naked. There were people all over the lobby checking in and just hanging out. They started staring at us and some of the guys began whistling and clapping. The four of us turned bright red and we jumped into an elevator.

We got back to the room in a hurry and ordered some room service. I took a shower and came out and started to get dressed when Teddy said “Hey wait a second, are you forgetting something?” “Force of habit,” I replied and I slid my panties back off. What are we gonna do for the rest of the night anyway?” Teddy said that Mike and Eric went to get beers and liquor and that we were going to have a party in Tim and Katie’s room since they had a really big suite with a big balcony. I figured that was better than having to go to the bar downstairs. Teddy and I ate and then had the most incredible sex we have ever had with each other. I realized it was because I was so horny from being naked on the beach all day. He told me that it really turned him on watching his friends and other guys look at me naked. I told him that I secretly was starting to like it too and said I hope he wasn’t mad about the body shots we did earlier. He said don’t worry about it at all. “You can do more later if you like, Mike said he would get tequila and limes for us.”

At about 10 o’clock Tim called and told us to come on up. Mike said ok, then reached into my bag and pulled out a pair of my black high heel shoes. He said, “Here, wear these. Me and the guys agreed it wouldn’t be a violation of the bet, and the other girls are going to wear heels or shoes too.” I put them on and walked into the hall. Two guys saw us in the elevator on the way up and said, “I wanna go where she’s going!!!” Teddy smiled and said that we were having a party upstairs and gave him the room number and invited them to stop by. It occurred to me that with the heels on I looked kinda like a stripper. My nipples got hard again when I saw the two guys staring at my pussy. Teddy looked at me after they got out and smiled and said “I hope you don’t mind?” I gave a nervous laugh and said, “If its ok with you its ok with me.”

When we got to Tim and Katie’s room I noticed that in addition to our group of 8 from school, there were about 10 other guys and girls from the hotel hanging out and drinking beers. Everyone but us 4 girls were fully dressed. I walked in with nothing but my heels on and said hello to everybody. Mike and Eric had bought several cases of beer and bottles of hard liquor and mixers. I had sobered up from the afternoon at the beach and quickly started drinking vodka tonics to calm my nerves. I had gotten used to the beach, I guess I would get used to this I told myself.

After a while if drinking and hanging out, Teddy walked away from me and went to mingle with everybody. After a while we ran out of ice. Mike handed me a garbage pail and asked me if I could go and get some more. “Me!” I said, “Come on, can’t one of you do it? I am naked for God sake!” He looked down at my heels and rubbed his hand over my ass and said, “I am sure you will be just fine.” I looked over at Teddy to see him doing a body shot off of Rachel’s tits. Fine I thought, I can do it.

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I left the room kinda mad at Teddy again and went looking for the ice machine. The one on that floor was broken so I tried another floor. It was broken too so I went to use the one next to the elevators in the lobby. Luckily nobody was around. On my way back into the elevator I heard a guy say “Hey beautiful, what are you up to?” I turned around and was relieved to see it was the two guys from Ohio State that we had me on the beach. I told them that we were having a party upstairs and that they sent me to get the ice. One of them offered to help me carry it and I invited them upstairs with me. In the elevator I felt kinda silly being naked in my high heels. One of the guys put his hand on my ass as we walked down the hall back to the room. I smiled and said that it was ok as long as he controlled himself. I figured I it would help me get even with Teddy.

After a while there were about 30 people at the party. To my surprise everyone was pretty well behaved with us. I let the Ohio State guys do some more shots off of my chest and made sure that Teddy saw it. He didn’t seem to mind. He was talking to Katie in the corner and I saw that he was rubbing her pussy very casually as he talked to her. She seemed to be enjoying every minute of it

One of the Ohio State guys asked if he could do another shot. I said sure and asked if he wanted to do it off my belly button this time instead. He said, “No, I had another idea.” He looked down at my pussy, which by this time was a little bit wet. I looked over at Teddy who was still enjoying Katie’s company, I was drunk again by then and said sure. I jumped up and sat on the liquor table and put my legs around him, digging my heels into the back of the couch. He took a cup of salt from the table and rubbed it all over my crotch. Everyone kinda sensed what we were doing and looked over. A few guys whistled and that got Teddy’s attention. Teddy looked over at the Ohio State guy who was standing between my legs and nodded that it was ok. With Teddy’s approval, he bent down and started eating me out right there in front of everybody! I moaned a little and everybody went nuts! When he was sure he had gotten all of the salt, he threw back the shot and sucked on his lime and pumped his fist in the air and yelled “Yeah baby! That was awesome.”

After that everybody started doing body shots off of everybody. Even the other girls at the party started to let guys do shots off of their belly buttons. Some guys took their penis’s out and Rachel did a few shots off of them. Eventually we ran out of tequila and the party started to wind down. It was about 3 o’clock in the morning and Teddy and I decided to head back to our room.

We went back to our room and Teddy and I had more incredible sex on our balcony. We then slept until about 11:30 and ordered breakfast. When it was time to go out to the beach I walked out of the room still naked. Teddy looked at the clock and said, “It’s after 12:00 you know, you don’t have be stay naked anymore.” “I know” I said smiling, “But I kinda like it now, is that ok with you.” He said of course and we headed down for another day at the beach.

The rest of the vacation was great. Me and the other girls stayed naked on the beach for the rest of the week and got great tans needless to say. The only time we got dressed after that was when we went out to the clubs. All in all it was a great time and I am sure not one any of us would ever forget.

Andrea