The Bet
by Amyscute2000©


My name is Amy 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 New England and had a lot of close 
guy friends on the men’s lacrosse team. When the second semester began me and 
three of my friends from my sorority, Katie, Rachel, and Jen began dating four 
guys on the team. I was dating a guy named Teddy, Katie was dating John, and 
Rachel was dating Eric, and Jen 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 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 lacrosse 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.” Jen 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 down 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.” John 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 immediately said she was in. I thought for a moment what it would be like 
to see John, 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, John 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. 

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 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?” Jen 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?

We told the guys of our proposal they pondered it for a minute when John 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. John 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?” John 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 board of 
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 Jen were all really nervous. 
John and Mike came to mine and Teddy’s 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, John 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. John 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 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 John, 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 Jen 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 loose 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 Katie’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 Jen walk to the bar. They were both busy 
talking to Katie and Rachel and helping them with their suntan oil. Eric and 
John 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 Jen 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 Katie’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. Jen 
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 Jen 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 Katie 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 Katie 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!” Jen 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 still 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 John 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 John 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 John 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 John 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 John 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. 

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.