College Trip to Cabo

About 10 years ago, I was attending a large public university in southern California. I was dating a beautiful blond girl named Jill, and we were just finishing up a stressful junior year. Classes had been rough for both of us, and we were looking for a way to blow off some steam before our summer internships started.

Jill and I decided the best way to blow off that steam would be to take a trip down to Cabo. We were trying to figure out where we should stay and how long we should go for, but we quickly realized that our meager savings probably wasn't going to be able to cover the cost of the trip. As we were talking over our predicament, Jill's roommate, Holly, overheard us.

"Guys, I don't mean to be nosy, but you do realize that Shane's dad is some fancy hotel executive. He can probably hook you guys up!" she said.

Shane was Holly's boyfriend. Jill and I really didn't know him that well. Although he and Holly had been dating for about 8 months, he didn't come around the girls' apartment much. And when he did, it was usually to whisk Holly away to whatever activity he had planned for that night. He seemed like a nice guy, but we had just never hung out.

"Really? You think he could do that for us?" Jill asked.

"Well, I was kind of hoping that he was going to ask me to go somewhere this summer. But I don't think he took the hints I was dropping."

"Well, maybe you should stop dropping hints and ask him directly. And maybe you should ask if he can get rooms for all of us..."

"What? You want me to go on the trip too?" Holly asked.

"Yeah! We should all go together... That would be so much fun! Plus it would give us a chance to get to know Shane a little better!" Jill responded. Obviously, we had not discussed Holly and Shane coming with us before Jill just put it out there. I wasn't sure if I liked the idea immediately, but as I thought about it, if letting the two of them come along was going to get us a nice place to stay, I was in.

"Oh...I don't want to get in your guys' way..." Holly said. Although smart and beautiful, she had a little bit of a self esteem problem. She was always worried that she was butting in when Jill asked her to come along to whatever we were doing, even when it was as simple as going to the movies.

"Nonsense. I really think the four of us would have a blast. We could go separate ways during the days, and then meet up at night and go clubbing!!" Jill said. I knew she was already planning the week's events in her head.

"OK... yeah. That does sound fun. I'll ask him!" Holly said. She was definitely warming to the idea.

So Holly wound up asking Shane, and man did he hook us up! We were going to get a luxury suite with 2 master bedrooms, a living room and kitchen right on the beach! It was at some all inclusive resort, and we were going to get it for FREE!

With accommodations taken care of, we then booked 3 round trip airline tickets for Jill, Holly and myself. Shane handled his own ticket because he was going to fly directly home at the end of the trip. I couldn't believe it! The trip was actually going to happen!

We were scheduled to leave about a week after classes let out. Let me tell you, it was rather hard to concentrate during those final exams with visions of Jill and Holly in skimpy bikinis down on the Cabo beaches. I was secretly hoping to see maybe a little more of Holly during the trip, but wasn't holding out too much hope. Although extremely hot, she usually dressed pretty conservatively. She was pretty tall, probably 5" 9," and had long flowing auburn hair. She was very fit, often going for long daily runs. So just seeing her in a bikini was going to be something in itself.

Finally, we were all done with our exams and only a week away from the trip. Of course, that's when the shit hit the fan. Jill and I walked into her apartment to find Holly sitting on the couch bawling. Apparently, Shane had gone to some party the previous night and had cheated on Holly. They had just had a huge fight, and Shane had stormed out. She was crushed, and needless to say, the trip to Cabo was the last thing she wanted to do. Jill and I tried to console her, but she said she just wanted to be alone and asked if we could call the airline to cancel for her.

We walked to Jill's room and discussed what we should do. Should we cancel our trip too? I really didn't want to, but we were now back in the same predicament we were in when we started. We couldn't afford the hotel costs.

"Maybe Shane will forget to call and cancel the reservation?" I thought out loud.

"I doubt it. But what if he calls half way through the trip? Then we'll be stuck with the bill, and we DEFINITELY can't afford to pay for that place," Jill responded.

"I guess you're right. What should we do?"

"I don't think we have a choice. We have to cancel the flights," Jill said.

Given the change in costs, I reluctantly agreed to cancel the trip. Fucking Shane!

So Jill called the airline to cancel the flights. I could tell immediately that the phone call was not going well. The very unapologetic airline rep not so politely informed us that we had non-refundable tickets. We could change them, but would cost us $150 per ticket, and would still have to use them within 6 months. After arguing with the bitch for a little while, Jill realized she was getting nowhere and hung up. This trip was turning out to be a disaster.

Holly had heard Jill talking "loudly" on the phone and came into her room. Now the 3 of us talked about what to do. I really didn't want to just eat the cost of the plane tickets, but we had nowhere to stay. I jumped onto the internet and called around, and was finally able to find one hotel that had an opening with a "reasonable" rate. It certainly wasn't an all inclusive, but it was close to the beach, and once down there, I thought we could still have a lot of fun. The catch was, it was still going to be pretty expensive if only Jill and I were to split the cost. It would be much more affordable if we split it three ways...

After much discussion trying to convince Holly that the trip would be a good way to unwind and forget about Shane, Holly finally agreed. I was really relived that the trip was still happening. It was not ideal for my sex life to have to share the hotel room with Holly... or was it? Before, I was excited about the possibility of seeing Holly in less than a bikini. Maybe now that we were sharing a hotel room, I might get glimpses of her getting in and out of the shower?

The week before we left dragged on forever. It seemed like every other hour Holly was changing her mind and trying to back out. But finally the day of the trip came and we convinced her to go. On the plane, Holly was a mess and kept saying what a mistake it was and how she missed Shane. I was beginning to regret my decision to make her come. We should have just payed the extra money.

The first couple of days we were there were miserable. I was on my own because Jill was constantly taking care of Holly, making sure she was OK and comforting her. They would wake up and Holly would head straight to the bathroom, change in there to a loose fitting T-shirt and jeans, and come out. Then she and Jill would head somewhere to talk, and I was left to find my own entertainment. Not only was I not seeing Holly in a bikini, but I wasn't seeing Jill either. Not to mention, absolutely no action at night...

Finally on the 3rd day, I convinced the girls to go to the beach. If they were going to talk all day, at least do it on the beach! Holly once again changed in the bathroom, but while she was in there, I managed to get Jill to change in the room. I helped pick which bikini I wanted her to wear and striped of her tank top and panties that she slept in. I was rubbing her beautiful 36C tits and staring longingly at her beautiful pussy. It had just a small landing strip of hair, and yes, the curtains did match the drapes: both were blond! I then moved my hands from her tits and started to move them to her slit when she pushed my hands away.

"Holly will come out any minute," she said.

"So? She's already seen you naked many times."

"This is different. Plus she's still vulnerable."

"Christ, are we ever going to have fun on this trip?"

"I'll make it up to you. I promise!"

And just like that, play time was over. She quickly put on her bikini. I slowly changed into my trunks, not really caring if Holly came out and caught me. Maybe I even wanted her to. But she took her time in the bathroom, and I was fully dressed when she came out. The three of us then headed to the beach.

We found a relatively secluded spot on the beach, and laid out our towels. Finally, I was going to see Holly in something revealing. I tried to not be too obvious that I was watching her undress. She slipped off her shorts to reveal black bottoms and a beautiful set of legs. They were a bit white since she never got any sun, but they were long, tight and her bikini nicely outlined her ass. Then she pulled off her T-shirt to reveal a matching black string bikini top. It wasn't the most revealing top in the world, but it showed some nice cleavage and looked great on her. Her breasts were actually a bit bigger than I had originally thought. She was always wearing sports bras and conservative shirts. Now that they were a little more free, I guessed that she was a size right between a 34B or C. But she of course picked the more conservative larger top thinking that it would have more material and coverage. What she hadn't anticipated was that it actually created some slack in the material, and as she moved around, at certain angles I was able to see pretty far up the top. Never quite saw a nipple, but I was definitely enjoying the view!

Jill had also removed her top layers, and the 2 girls laid down on the towels to soak up some sun. I had to remind them to apply some sun screen (I didn't want them burning and spending the rest of the week covered up indoors!), and happily watched as they applied it to each other's backs. I was staring at them from behind my sunglasses, pretending to read my book, and 10 minutes later, I wondered if they noticed that I hadn't turned the page!

It was getting close to lunch time and I volunteered to go get some lunch. Just down the street from the beach, I found a local taco shop to pick up some cheap food to go and some beers to bring back to the girls. While I was there, I saw some flyers for a nightclub that was having a ladies night with cheap drinks and a homemade bikini contest. Just the thought of Jill and Holly prancing around on stage in next to nothing made my dick start to stir, but I quickly dismissed the thought. There was no way the 2 of them would ever do anything like that. Especially Holly.

There were actually two versions of the flyer. The first one just advertised that it was ladies night and had dancing with drink specials, and the other mentioned the bikini contest. I grabbed a couple of the first ones and headed back to the beach with the food. Hell, I could play dumb and try and convince them to go to a night club. Then, even if my girls wouldn't do it, maybe I could still see some skin from some other girls!

As I headed back to the beach and the girls, I noticed Jill and Holly were both lying on their stomachs with their tops undone so they wouldn't get a tanline on their backs.

"Who's hungry?" I asked.

"I'm starving. Thanks for doing that, sweetie," Jill replied.

She propped herself up to grab a taco, but didn't fix her top! She just sat up and grabbed a taco and a beer! She looked amazing just sitting out in the open, topless on the beach!

"Jill, what are you doing??" Holly exclaimed as she fumbled with her strings behind her back, her breasts still firmly pressed on the ground.

"Oh, what's the big deal?" Jill said as she shot me a wink. Apparently, this was how she was making things up to me! "We're here on vacation on a mostly deserted beach. Even if someone does walk by, it won't be anyone we know. Let's live a little!"

"Well, that may be okay for you... But Tom's here. And I know him."

Holly finished fixing her top, sat up and grabbed a taco. Damn...

"Besides, I'm not that kind of girl," she continued.

"Wait. What does that mean?" Jill asked, as she took a bite.

"Oh nothing. It's fine if you want to do it. I just don't think it's for me."

"Well, I think you should lighten up!"

I just sat there eating while enjoying the view. Even if Holly wasn't going to partake in Jill's new found freedom, I was happy. Finally this trip was starting to pick up.

"Well, ladies. While I was getting lunch, I think I found something cool to do tonight. There's a club downtown throwing a ladies night with some cheap drinks. It looked pretty fun."

"I don't know," Holly said. "I'm just not sure if I'm up for that yet."

"Well, I think it sounds like fun. Why don't you think about it, but I think Tom and I are going to go and have a good time."

The rest of the afternoon was great. I think I read about 1 page of my book. I just kept staring at Jill's tits exposed out on the beach. I had seen them many times before, but there was just something different about seeing them out in public. A couple times people walked by and she made no effort to cover up. What an amazing girl.

There were several times when I caught Holly staring at Jill's tits, too. I think she was jealous of how Jill could let loose. Holly was always so uptight, she really needed to let her hair down. Or take her top off as the case may be! I figured we still had 5 days here in Cabo... maybe by the end she'll come out of her shell. But I knew to not push too hard too early.

It was starting to get late in the afternoon, and we headed back to the hotel room. We all showered (unfortunately, one at a time!) and when I got out last, I came back in the room with the girls still in their towels talking about what they were going to wear tonight. I was floored for two reasons. One, somehow Jill had convinced Holly to go out and she seemed into it, and two, Holly was still only wearing her towel! Normally, she would never let me catch her this way!

These hotel towels were rather small, so with the top covering her tits, the towel was barely long enough to cover her ass cheeks. I had probably seen more skin out on the beach, but just knowing that there was nothing on under that towel was driving me nuts.

The girls decided on which skimpy outfit they were going to wear for the night, and Holly disappeared back into the bathroom to change. Jill then dropped her towel and put on her thong and little black dress. No bra. She looked amazing. I wanted to take her right there, but decided it would be better if I behaved myself. I threw on some shorts and a shirt and we waited for Holly to come out. She opened the door and emerged wearing the sexiest thing I had ever seen her wear. She had borrowed a very small skirt and loose fitting top from Jill. And from the plunging neckline on that top, it was obvious she wasn't wearing a bra either.

We headed out, had a nice dinner, and headed to the club. As we turned the street corner, we could hear the music thumping out of the club and the girls we already swaying. They were READY to dance!

As we were waiting in line to get in, Jill noticed a sign for the homemade bikini contest.

"So, Tom... is this why you wanted to come here tonight?"

"No!" I lied. "I had no idea this was going on. I just saw the ad for the club and thought it would be fun."

"Oh, sure!" The girls looked at each other. I sensed they were silently debating whether to stay or not.

"Hell, it's still ladies night, the drinks are cheap, and the music sounds good from here. I say we give this club a shot," Holly said. Jill and I both looked at each other shocked.

"Sounds good to me!" I said.

We got in and immediately hit the bar and got some pretty stiff drinks. We all alternated dancing and getting rounds of shots, and it didn't take long before we were feeling really good. The club DJ made an announcement that the bikini contest would start soon, and anyone who wanted to enter the contest should sign up at the bar.

"So what does this contest entail?" Jill asked.

"I'm not sure," I replied, actually telling the truth. I really didn't know what the contest was going to be like, but I imagined it would have girls parading around in "bikinis" so I was in! "Why? Are you interested?" I asked.

"I don't know... I think it might be fun," Jill said.

"You're crazy!" Holly told Jill.

"Oh, come on. We're on vacation! Let's see what it's like."

I couldn't believe that Jill was actually considering it. We walked over to the bartender and asked about it. He called over the girl in charge of recruiting for the contest. She explained that there was a room in the back filled with all kind of props that girls could use to create their own bikinis. Once the contest starts, each girl that had entered would come out one at a time and dance for a couple of minutes. Then after every girl had gone, everyone would comeback out on the stage and there would be a vote for 2 finalists to go on to the final round. There would be another round of dancing and then a final vote, where the winner would win $500, and the other finalist would get $100. There was one final twist that girls could team up and go together, but they would have to split any prize money. And everyone that entered would get free drinks for the night.

"Wow!" Jill exclaimed. "That's a decent prize. It would go a long way to help pay for this trip."

"Really?" Holly asked. "You're REALLY considering this!?!?"

"Look, I already told you. We're on vacation and no one knows us here. I think it would be fun to let loose a little. And if we win, that would really help. AND... I really think we should do it together."

"NO!!!!" Holly gasped.

I wanted to offer some encouragement, but I knew to just keep my mouth shut. Jill was already doing an expert job at handling Holly.

"Holly. I love you. But come on. You've been moping around on this trip and it's time to move on. We need to show this town we know how to party!"

"I don't know if I can. How much will we have to show?"

"Who knows. I'll probably flash my boobs a bit. You can do as much or as little as you want. But you ARE coming up there with me."

This was great! Jill was so caught up convincing Holly that she should let loose, that she had just decreed they were both going to enter the contest. My dick was stirring thinking about what was going to happen. Jill then called the contest organizer back over and signed the consent form. Then she handed it to Holly.

"She and I are entering the contest as a team," she told the girl.

Holly stared at Jill for a second contemplating what to do. For a second I thought she was going to storm out of the club, but she looked down at the form, hesitated for one more second, and signed her name.

"Great!" the girl said. "It's almost time, so you girls can head back and build your bikinis." She turned to me. "You'll have to wait out here," she said to me, winking.

"No problem!" I replied, still in shock at what just happened.

It was good that the girls had to head back to the room immediately. It didn't give them time to think about what they were going to do and back out. I kissed Jill and wished her luck. She looked at me with wide eyes, the reality of what she was about to do starting to sink in. I just winked at her and told her I loved her.

I wandered around a bit, and couldn't wait for the contest to start. I got a drink, and headed up to the stage to get as close as I could to the action. Finally the lights on the stage brightened and the DJ announced the start of the contest.

Right from the start, I knew this contest was going to be amazing. The first girl to come out on stage was gorgeous. She was tall, around 5' 7," blond, and wearing next to nothing. On the bottom, she had clear saran wrap covering her very small black thong on underneath. And on top, she had bows that you would find on gift packages covering her nipples and nothing else. She danced around on stage, her 36C tits jiggling and bouncing nicely. Toward the end of her dance, she popped off the bows, and flashed the crowd, which was greeted very nicely. Then she stuck them back on and disappeared behind the curtain.