Chapter 2: Dinner and the Incline

My thoughts were interrupted when Greg pulled into the driveway and I stood there waiting for him at the door. What the heck, I was dressed up like a lady so why not have him treat me like one and walk me to his car from the door! I hurriedly put on my heels and waited impatiently. Greg was dressed nicely in a handsome suit that looked like it was brand new and he looked really sharp. He opened the door for me and then closed it as I got into the car and we were off. I looked back and couldn’t help but smile as I wondered how long it would be before my parents realized I’d gone. Well, for their sake I hoped it wouldn’t be for a while yet!

Greg drove me to dinner at a fancy restaurant overlooking the city. We parked and then rode The Incline up the steep hill from the parking lot to Mt. Washington. Several other couples were in the cab with us and it was a quick ride to the top. From there it was a short chilly walk to the restaurant but fortunately I was wearing a warm jacket which helped. Once inside the host looked at us a bit quizzically and once he seated us I realized why. We were by far the youngest couple in the place and probably half the age of the next youngest. Looking at the menu I realized why. My God, the prices were exorbitant! I sucked in my breath and Greg must have noticed.

“Don’t worry Kelly,” he assured me holding my hand across the table, “I wanted tonight to be special and you’re more than worth it.”

Well, it was indeed a wonderful dinner. The whole thing took close to three hours during which we had a great view of the city at night looking through the full length windows lining the exterior of the restaurant. It was years later before my dad confessed he had helped Greg with the reservations, using his pull to get us an in credible table. Greg was a perfect gentleman throughout and the waiter even treated us like adults and not a couple of teenage interlopers crashing a fancy restaurant. Although we didn’t have any wine, which undoubtedly helped to keep the tab low, I stole a peek at the bill afterwards and saw it was close to $150! Well, this certainly qualified as the most expensive dinner anyone had ever bought me other than my dad.

We headed back to The Incline and this time there were no other passengers waiting to board. Having ridden it many times, I knew the trip only took a few minutes but why waste such an opportunity? As soon as we got in the car I slid close to him in the seat and put my hand firmly on his crotch. This was actually the first time all night anything sexual had come up between us so I figured he had to be horny as hell waiting for me to make a move. I looked Greg in the eyes and he smiled back at me which was all I needed. Quickly I unzipped his pants and reached in for his cock which was already Mellon its way to be a full erection. The car lurched and we started our journey down the hill as the cable slowly lowered us. I leaned over and took his cock in my mouth and started sucking it, nothing fancy as we didn’t have a lot of time, just a simple up and down motion as my mouth pulled on his cock and my tongue ran all over it. He got totally hard almost instantly which was amazing considering how big he was when he was erect.