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."
"Oh, I don't know why you don't, David. You're really a cute guy."
"Well, I don't know, I guess...well, I don't know why."
"Maybe you're too shy? Do you think that's it?"
"Yeah, maybe, yeah, I think so."
"You know girls are a lot like guys, they want to be complimented and they like a guy who will kind of take charge and be more sure of himself. So, what would you say to me about what you see and what you were looking at when I sat your plate down. Just go ahead and tell me, I won't be mad. Just try telling me what you're thinking."
She was right, of course, I was too shy with girls and maybe I should just do what she asked.
"Well, when you bent over, it was like I could see everything and you're really pretty there."
"What did you see, tell me in detail?"
"Um, your breasts."
"How about my nipples? How did they look?"
" I saw them, yes. Nice."
"Come on, David. If you do better, really try, I might just pull the top off altogether."
If you're wondering if I had a stiffie, well, it was one of a lifetime.
"I saw your breasts and they're really beautiful, so large and full and your nipples are so sexy, all hard and sticking out."
"What would you like to do with these nipples?" she asked as she pulled her right breast up out of her nighty. I thought I'd faint right there.
"Um, touch them, feel them, suck on your nipples, lick them," I said trying to keep myself sane as my heart raced pumping blood southward.
"Tell me more, David. Your sister won't be back until tomorrow morning."
"I...well, I'd love to get you out of your nighty and just kiss you all over," I said trying to think of something, anything to keep this going.
"Where is it you most want to kiss me, David?" she asked as she leaned forward still with her right breast in full view.
Well, I'd never done anything in sex at all but at least I'd listened carefully to the guys I hung around with when they were going on and on about it.
God, what do they call it...cunneylate? I couldn't think of the long word to use, all I could think of was "I'd love to eat you out. Give you oral sex." I did get it out at least.
"Have you ever given a girl oral before?"
"No, but it's something I really want to do. A lot."
I added that last to kind of seal the deal, so to speak.
"We have the rest of the day and all night together, David. I'm guessing you haven't had sex yet, right?"
She said 'yet' like it might be just around the corner, oh, my lucky day.
"No but I really want to. And I couldn't have a more beautiful girl to do it with than you, Brenda," I said as I slid my hand over to take hers. I really thought I needed to make some physical move.
She took my hand and moved it to the breast that was out.
My heart didn't quite stop but I almost thought it might. She was smiling at me as my fingers flexed around her firm, full breast as her other hand reached under the table to grip the bulge in my pants.
"Mmm, I'll bet I know what's in here making your pants swell all up," she said jokingly. "I think you should let me see what's in there," she said nodding to my crotch. "Come on, let's see," she said as she pulled the zipper down and unbuttoned the waistband to pull my pants down and off.
"Oh, this is nice," she purred as her hand rubbed back and forth across the bulge in my briefs. "Let's see what you've got under here, David," she said smiling up at me as I lifted my butt up as she pulled them down and off, my dick springing free.
"Oh, my. Such a nice young cock. Has it ever been sucked?"
My heart was racing as I told her it hadn't.
Without a word, her head dipped down as her lips slid over the crown and began softly sucking while her hand caressed my balls underneath.
I'd jacked-off I don't know how many times, lots and lots, and nothing, I mean nothing, ever felt that good before. She just sucked softly sliding her wet lips back and forth over the tip.
"Oh, that's awesome, I've...I've never felt anything that good in my whole life," I gasped.
She kept sucking and rubbing her soft, wet lips over me as I panted in ecstasy. Then it hit. I had almost no advance warning as I began cumming in her mouth. She was only working on the end of my cock so some of my cum had leaked out the sides of her lips.
When it happened, it happened suddenly, I began shooting my cum into her mouth and she just kept sucking and sucking. She took every drop, then lifted off and wiped her tongue around as more oozed up from me. She licked until there was no more.
She sucked a little more then raised her head and pulled me down to kiss me sliding her tongue inside my mouth as I held her boobs. I was in heaven. And I had until the next day with her, my sister wasn't getting back until very late.
"I think you were kinda horny, David. That better?"
"Oh, lots better, that was the best thing that's ever happened to me," I told her and I pulled her head to mine and kissed her hard. During that kiss, her mouth opened and her warm, soft tongue came into my mouth. I'd not done a lot of kissing but now I tongued her back as my hands fondled her boobs.
"There's more that can happen to you, David. Have you had sex before?"
Yes, I realized that maybe this was the prelude to asking me if I wanted sex with her and I knew I did, I mean, who wouldn't? So, I answered her honestly.
"No, but I would love it to be you, Brenda."
"Oh, our boy is coming out of his shell. Well, come follow me," she said as she got up and walked down the hall to her room.
As we entered, she stopped and turned to me, saying, "Well, I'll just leave everything up to you, David, you're on you're own, I don't plan on stopping you from pretty much whatever you want to do with me. Have fun."
Up to me? Well, here it was. She sure seemed willing to let me, well, I guess even have sex with her. But, truthfully, I was doing all I could to keep from shaking to death. Yes, I was scared. I was an eighteen-year old kid, never done anything in sex and here she is, a grown woman, at least my sister's age, no doubt well-experienced in sex and brimming with self-confidence.
I knew I had to start somewhere, I had to do something, so I put my arms around her and kissed her. Her mouth opened just a bit so I went ahead and slid my tongue inside as we held each other closer.
Then I backed away a bit and looked at her, then took the hem of her nighty and pulled it up as she raised her arms helping me take it off.
Beautiful, stunning, just as pretty as any girl I'd ever seen in Playboy, that's for sure.
My hands took her breasts, they were firm and full, so warm and soft. Then I knelt down on one knee and took her panties and pulled them to the floor as she stepped out of them.
I was face-to-pussy with her, she was all smooth and shaved clean, her plump slit dewy with moisture. I leaned and kissed her softly there, then licked in her groove as she looked down at me.
"Mmm, that's nice, David."
I stood up and asked her to get in bed with me which she did.
She was on her back so I knelt there next to her leaning over her kissing and licking her body from her neck down.
Her nipples were awesome, hard and erect, wonderful to lick around and suck on. As I leaned over her sucking one, I felt her hand take my cock, I almost fainted. She didn't do anything, just held it, softly squeezing me every once in a while as I kissed down her body.
I got to her abdomen and was really getting excited. Her pussy was right there, next in line. I moved that vital few inches, then kissed softly followed by a lick along the crevice between her legs.
Her knees parted widely, I knew it was an invitation so I moved down below her, between her long, beautiful legs to begin licking up and back tasting the first pussy of my life. I knew then that I would always crave the taste of women.
Her hands came down to pull herself open as I lapped and flipped my tongue around where she opened to that lovely mysterious passage where I wanted to put my cock.
"Mmm, good, David, feels good, right in there, oh, yes," she cooed as she moved her hips around while I tongued up into her. "Mmm, you make my pussy feel so good, I'm really glad you came to visit."
As much as I wanted to put my dick into where I was licking, I was just loving giving oral sex. When I'd heard guys talking about it, well, I wasn't sure I wanted to do it. I knew I wanted to fuck, that was easy, but putting my mouth and lips and tongue down there, I wasn't so sure.
Oh, now I was, it was such a beautiful place to kiss and the effect it had was more than I thought it would be. She really loved it and it kind of made her crazy.
"More, oh, yes, YES, um, make me cum, oh, so close," she groaned then she began shaking and cried out in a way that almost sounded like she was in pain but it was just the opposite.
But I kept doing what I was doing, licking and driving my tongue in and around her open pussy until she screamed and locked her legs around my head pulling my face hard into her pussy.
What had happened was incredible, so strong, so intense. I'd never given a girl or a woman an orgasm before, I had no idea what it would be like. I just imagined it would be like when I cummed. Oh, this showed me how wrong I was about that.
She let my head loose and pulled me up on top of her, kissing me over and over.
"Mmm, oh you...you were good, David, you must do that to a lot of girls back home," she said still trying to get her breath back.
"I've never done it before, this was the first time I've done that."
"Oh, you're already as good as most guys. Mmm, I'll have to show you a few things so you can even be better," she said as she held me tight.
I couldn't really help it, I was on top of her, her legs were kind of open and my dick was right between her legs. So, I kind of pushed.
"You trying to fuck me, David?" she said.
"Oh, no, I just...I didn't mean to..."
She interrupted me with, "You can if you want to, I think I'd rather enjoy it about now."
"You really mean it?"
"I really mean it. Yes. Have you done it before?"
"No, this would be my first time," I admitted.
"Oh, Jimmy McWilliams," she sighed.
She laughed and told me then that he was the first boy she ever had sex with. It was her first time and his as well. And that the second virgin she'd ever had sex with was going to be me and she told me to go ahead and push into her.
I couldn't believe she said that. I'd really thought she was kidding me about sex earlier, I mean, I was eighteen, a kid, even a small-town kid, and she was a mature professional woman in a good-paying job and probably had all kinds of business guys all over her all the time. And she was telling me to go ahead.
I pushed my hips forward and felt myself slip between her pussy lips, all nicely moist from my licking her and I just pushed right up into her all the way.
It was that moment when I realized just how wonderfully the female body was constructed to receive the male to the absolute joy of both. Nothing equals it.
"Mmm, nice, David, you like it so far?"
"Oh, I...I...you feel incredible inside, it's just wonderful," I stammered as I began moving back and forth. Oh, that was simply the best feeling of my life. No wonder everyone does this, I thought. My dick was in heaven.
She was smiling at me as I rubbed and squeezed her firm boobs while my dick went back and forth. There was no way I could hold out from cumming, it just felt too good and, yes, I went off inside her after only a couple of minutes.
"Oh, uh, oh, I did it. I'm sorry I was so fast. I've just never..." I got out when she pulled my head down and kissed me fucking my mouth with her tongue.
"Don't worry, David, it's fine. I pretty much expected it, after all, you're pretty excited, right?"
"Oh, am I. This is just the best thing in my whole life."
"You still feel pretty hard to me, so let's just go on," she said softly as I moved my hips back and forth.
She was smiling up at me knowingly as I went in and out of her. Then, she said, "Hold on, I want to get on top," and she gripped me tight and rolled us over and got up to begin fucking me up and down as I held her wonderful breasts.
"Oh, I like this, I get to play with these," I told her.
"I like it on top, too, you'll find that out, David, and you can pinch my nipples, that really gets me hot. Or nibble them," she said as she leaned forward to touch a nipple to my lips which I opened to take it in and suck.