Chapter 1
It was winter vacation during my senior year of high school when my sister invited me to spend the holidays with her in Chicago.
I'd never been to a city that size and just the thought of it was pretty exciting. I knew she lived in the heart of the city where I could just walk around and see the sights. Also I knew that there was plenty of bus service as well.
So, I was really psyched. What eighteen-year old kid from Norman, Oklahoma wouldn't be? The big city, the bright lights. And I knew there would be several times while I was there that my sister would be flying, she's an airline flight attendant, and I could really explore the city on my own.
She lived with another flight attendant, Brenda, she'd said her name was, and that she'd be gone when I flew in.
So, on the nineteenth, my parents took me to Will Rogers Airport on the outskirts of Oklahoma City and I got on a flight that went to Chicago nonstop.
Now, you may have flown all over the world but, for me, it was something new and I must say, it was pretty exciting to sit at the window and watch the takeoff and, two hours later, the landing. It was a toss-up which one was more fascinating.
I really didn't have any checked bags so I went right out and there was Debra, my sister, waiting for me. I hadn't seen her in almost a year and she really looked terrific in her uniform which she still had on as she'd just returned from a flight that afternoon herself.
We hugged and she began gushing about how grown-up I was looking and how I was turning into a 'hunk.' That's the first time I'd ever been called that and chalked it up to her not having seen me in so long.
But I did tell her how pretty she looked in her uniform and asked her if she gets guys asking her out a lot.
"Oh, yeah, some, but it's hard to tell which ones are married. I know some are, you can see their rings and all and they just make a pass anyway. But that doesn't get them far. Most aren't cute, eligible hunks like my little brother," she said as we caught a bus to where her car was parked.
We got to her place, parked in the garage and took the elevator up to her apartment.
As soon as we got inside, I went right to the long window across the main room and looked out at the city. The view was amazing to small-town kid like me.
"There it is, The Windy City, David. Welcome to Chicago, I think you'll have fun here."
"Yeah, this is so cool and so, not Norman, Oklahoma," I told her as I stared at the city out there, all busy and bustling, just amazing to this eighteen-year old country bumpkin.
I was a fairly sophisticated kid, actually, really into computers and other kinds of technology, but the city below me seemed amazing, just thrilling.
She told me to put my stuff away and that I'd be sleeping on the sofa when she was home but when she was scheduled, I could use her room.
"I'll be leaving tomorrow about noon but Brenda is due back tomorrow night late. I've got some stuff in the freezer, pizza and stuff, for tomorrow night but tonight I'm taking my little brother out for Italian food, Chicago's got great food, just wait."
So, I put my things away and went back to look out the window. Debra came out of the bedroom over to me and stood next to me looking out.
"This is so exciting, I just can't believe I'm here," I gushed.
"Well, there are muggings, killings every day; being up here, high above it all, it does look great. And in a lot of ways it is. But there's a dark side to it all as well. You just need to stick to the really populated and well-lit areas at night. It's not Norman, Oklahoma."
We went out later to an Italian place where the people seemed to know my sister. The food was just the best, some things I already knew about but they had lots of things I'd never heard of. I'd told myself that this trip was going to be one where I was going all out to try new things and I ended having two appetizers and a pasta that were out of this world.
Deb and I walked around the fancy shopping district near the Water Tower and I saw more super-expensive stuff than I ever imagined existed. She even took me into a woman's lingerie shop that was giving me a hard-on with all the stuff on display. Welcome to Chicago, I thought.
Then we walked some more and ended back at her building, went up and I got ready for bed. It had been a long and exciting day.
She kissed me goodnight telling me that she'd probably be gone by the time I woke up and to stick within a few blocks of her building if I went out. I did plan to check out a game shop I'd seen and made a note to remember how to get there.
So, the next morning about eight-thirty, I woke up and got some breakfast. Then I did the usual things like shower and stuff, watched some tube and went out.
I was back for lunch after spending time in the gaming shop and made some lunch.
She had told me they had a pool and workout spa that I could use so I put on my trunks and went up to the pool level and swam for about an hour.
After that, I went out again, walking around a while then back to her place where I had a pizza and watched some DVDs she had.
Then, tired again, I went to bed on the sofa, forgetting that she'd told me to use her room when she was traveling, and went soundly to sleep.
I heard something the next morning, like someone was in the kitchen and looked at the clock. Nine-twenty-seven.
I got up and was sitting there on the sofa when out of the kitchen came a beautiful woman in a nighty. It had to be Brenda, my sister's roommate.
"You're David," she said as she approached me with her hand outstretched. "I'm Brenda, your sister's roommate. Welcome to Chicago."
I had to stand up, that was the way I was taught growing up but seeing her had already given me an erection. I hadn't jacked-off since I'd come to Chicago so I was helpless to control my runaway horniness.
So, I was kind of stooped a bit trying to minimize my showing as we shook hands.
She was standing there in what I've since learned was a baby doll nighty, a white lace one which contrasted beautifully with her dark, tanned skin. Most fascinating were her dark nipples showing through making me even harder.
"I'll bet you're hungry, come on, I'll make you breakfast," she said and turned to walk to the kitchen. What a figure. She was Playboy material for sure.
I pulled on my chinos and went to take a pee and was soon in the kitchen watching her make toast and eggs. It was when she brought my plate over and put it on the table that I saw the tops of her wonderful boobs. If she knew she was giving me a show, she sure didn't seem to care.
Right as she sat the plate down, her eyes looked up and caught me staring down into her nighty. She looked down and saw the top was gaping open, then said, "Ooops, guess I gave you a little show, sorry," and stood back up.
Softly I said, "I'm not sorry," and grinned.
"Well, I suppose that's a compliment and I thank you for it. Did you like what you saw, David?"
"Oh, I liked it very much," I managed to squeak out.
"So, what kind of girls do you like? Are you a 'breast-man,' is that it?"
I couldn't believe I was sitting there with this beautiful, scantily-clad woman talking about whether or not I liked breasts.
"Um, yeah, I guess so."
"Does your girlfriend have big breasts?"
"I...I really don't have a girlfriend."
