Family Business & Sexual Adventures

The first couple of double-dates Jim and his girl used his bedroom and my date and I used mine. It wasn't long, however, before the four of us would make out in the living room. Sometimes we adjourned to one of the bedrooms, all four in one bed. Jim and I liked that a lot and most of the girls found it exciting. I liked watching Jim's big cock slide deep into pussy. I tried to time my thrusts to coincide with his. We would look at each other and grin.

Two girls were particularly aggressive and Jim and I swapped mid-stream. Then we swapped back. That was fun. Afterwards the girls giggled and laughed about being shared. A few minutes later we were back in bed. I ate my brother's cum from his girl, and he did mine. The girls said we were the best fucks they ever had. We took advantage as much as possible.

That next summer was rather exciting. Jan had moved on to places unknown. She was in love with my brother and apparently decided it wasn't going to work out. Too much history, perhaps.

Fortunately, Jim and I were highly thought of by the local girls. Money, good looks, buffed bodies. Jim helped introduce me to town girls, some of whom he had already bedded. By the end of that summer I had explored the delights of four different pussies.

As you probably have guessed, our college years were filled with sex. I continued to watch and learn as Jim plied his craft, seducing girls left and right. In almost every case I benefited and gradually took more initiative.

The junior and senior girls especially were fun. Jim would do the initial seduction, then introduce me. He explained that we were brothers and did everything together. "Together?" the girl would ask, guessing where this was headed. "Yes. You get us both. You interested?"

Invariably the answer was yes.

After graduation I joined our family business which included a river rafting company and three outfitter locations. The first thing I did was get certified so I could run rafting excursions. The river was up that year owing to good snow melt, so business would likely be good.

I found opportunities for meeting girls while running the rafts was very limited. Most rafting customers came in groups, families or parts of families, or organizations. No single girls and few pairs. Fortunately, I was in the good graces of two town girls. If truth be known, I was looking forward to snow and skiing.

I am an expert skier, having started when I was five years old. Our family knew the management of the ski resort and I had no problems getting a job as an instructor.

As one of the least senior ski instructors, however, I mostly got beginner groups. I worked hard to teach the newbies the basics but did have to admit that it was boring. I hoped to get some private lessons. The pay was better and most who wanted a private lesson were already reasonably good skiers.

I had a reputation among the ski instructors for being one of the better bump (mogul) skiers. So I was scheduled for two days of bump lessons. That morning I met my student. Wow, what a looker! I later found out she was twenty-one. I was going to enjoy these two days!

Riding a two-person chair lift usually leads to some chit-chat. I had found years ago that it was very easy to strike up a conversation with your seat-mate over the course of an eight or ten-minute ride.

Her name was Cathy. Huh oh, she said she was here with her boyfriend, who was skiing on his own for the moment. Damn, double damn. She was a very nice girl with a bubbly personality. And a great skier. We unloaded from the advanced lift and headed to the blacks.

Even though I knew my chances of bedding this gorgeous girl was zero it was still fun to talk her up. She was from Minnesota and grew up in Lake Tahoe, which explained her skiing skills. She was twenty-one and had been dating her boyfriend for three years. He was a little older and in business. She accompanied him on some business trips, many of which were international.

She said they were staying at the Grande Lodge resort. Wow, that was the super ritzy mid-lift resort. Not only was it almost impossible to get a reservation, it was ferociously expensive. The least expensive suites, I had heard, went for $3000 per day. Cathy said they were staying for most of the season, about three months. Big bucks.

We skied the easier blacks and then moved to the tougher ones. She needed some coaching on checking and using her poles, but all in all was a very competent skier. Each lift ride we became more comfortable with each other.

The morning lesson ended at noon and would resume at 1:30. Usually I would leave my student at that point and have lunch in the cafeteria. But she suggested stopping for lunch at their resort where she planned to meet her boyfriend.

I was surprised. Very surprised. He was, I guessed, about thirty-five, definitely older than I expected for sweet 21-year old Cathy. Good looking, dressed well, and was very gracious. Needless to say, the lunch surroundings were very classy. Cathy enthused about my teaching skill and how much I was already helping her.

After a sumptuous lunch she and I resumed our lesson. Her boyfriend, Stan, was re-joining two others and would meet up later. I mulled over the apparent arrangement. Cathy seemed so nice and innocent but it sure looked like she was a trophy girlfriend, with all that implied. Well, not my place to judge. I still liked being around her and we had a great time skiing that afternoon.

The next day was a virtual repeat. Afterwards Stan said he hoped that I could join Cathy and him for some casual skiing the next day. I arranged to take the day off.

Stan was an excellent skier. Another fellow, George, joined us. He was introduced as a business associate. I later found out that meant body guard. We did all the blacks, a few double blacks, and also throttled down on some tougher blues. It was a fun day for everyone.

He invited me to rejoin them for drinks and dinner. I went home, cleaned up, and changed into my best casual clothes. We met at Andre's in town. I noticed that "George", his body guard, and another fellow were discretely seated two tables away. Ol' Stan must be in some interesting business...

"How about a nightcap at the resort?" he suggested after a sumptuous meal that must have cost him several hundred.

"I would like that. I've heard so much about the Grande Lodge resort. Lunch there was very nice and I thank you for your hospitality."

Their suite was about what I was now expecting, one of the more expense ones no doubt. Two stories, three bedrooms, etc, etc. I also learned that "George" and the other guy were ensconced in another suite, albeit one of the "cheap" ones.

Stan was a gracious host and I had a good time. His driver took me back home in the limo. The three of us arranged to again ski together the next day.

At lunch Stan announced to Cathy that he had to leave for a meeting and wouldn't be back for four or five days. She volunteered to accompany him but he declined. "Not this trip. Stay here and have fun skiing. Spend time with Bob, he's a nice guy." I noticed Cathy look quizzically at him, then turned towards me and smiled.

"Yes, he is. Well, hurry back soon, honey."

Cathy and I had dinner together at the resort. "Stan was my first, you know."

"Your first?" I was slow on catching on.

"Yeah, he took my virginity. I just turned eighteen. We met at a black-tie affair. I was one of the servers, he was one of the honored guests. Three hours later we were in his suite and his cock was in my pussy.

"Not very romantic but he definitely swept me off my feet. Anyway he asked me to join him, to be his girlfriend. We have traveled the world. As you have probably noticed, he is very wealthy. We have an arrangement. When he's on his business trips he's seldom alone. Most places he has a girl or two that he beds. It's just sex. He did that before we met and I assume will after we split up."

"Split up?"

"I'm not naive. He likes me because I'm very young and very good looking. Give it a couple more years and he might move on. I'll understand. I get to see places and do things that would otherwise be impossible. He spends money on me. I know that sounds crass. And he's very good in bed and I found out I really like sex."

"And what do you do when he's on his trips? What did he mean when he told you to spend time with me?"

"He was telling me that if I wanted to go to bed with you, it was ok. He's done it before."

"So you have permission. And do you want to go to bed with me?"

"Definitely. I sized you up that first day on the lift as a guy who is exciting to women. Nice body, athletic, great personality, very good looking, reminds me of Tom Cruise. I like athletic guys, they're usually very good in bed. Are you?"

"With that kind of build-up, I would have to say yes, even if I lied. But to be honest, I've had my share of pussy. Here in town and at college. But you know, there's only one way to find out. Shall we?" This conversation proceeded at such a fast pace but I wasn't about to be reticent.

She took me by the hand and led me to their now-empty suite.