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.
