Big Sister in the City

Here's a new storyline. Sorry to those folks asking for the continuing of other story lines. I have to go where my creativity takes me. Hopefully if you liked the others, you'll enjoy this one. Mind you, this is a bit different than my others. There is far more exposition and it takes quite some time to get to the 'action' as it were. And, while definitely fantastical, it is not near as over the top. And now the typical disclaimer about how this isn't meant to be realistic, so no need to post messages about "That would never happen, blah blah blah". And lastly, thanks for all of the support from folks who enjoy my work. Your comments and emails are what keep me going!

Josie, Sister - Josie Davis

Esther, Roommate - Esther Baxter

Denise, Roommate - Denise Milani

*

I was a bundle of nerves as I stepped off the plane at La Guardia airport. Here I was; 18, just out of high school, and a Midwest farm boy, and I was soon to be in New York City! On top of all of that, I was going to be living with my sister whom I hadn't seen in three years.

Josie was the oldest of the five of us, with me being the youngest. Seven years my senior. She was also the black sheep of the family. Why? Not for getting into trouble, being a bad student, being an alcoholic or any of the other things that usually upsets parents. No, she had graduated with honors, and had a six figure job. But that job was in New York. That was the problem. Unlike my other siblings who are still living near Iowa city with the rest of the family, Josie went out into the world and didn't look back. When she did come to visit for holidays, my family would make all kinds of snide comments. It finally came to a head a few Christmases back, and Josie finally had enough. A fight ensued and she vowed never to return.

Unlike the rest of my family, however, it never bothered me that she left. I mean, I missed her...a lot, but I was proud of her. Even when we were younger and she would talk about 'getting out of this place', I was always supportive. I knew she wanted bigger things. She deserved better things!

Despite the age gap, Josie and I had always been close. When I was very young she was protective and tried to guide me. As I got older our relationship grew. She'd help me with homework. I'd listen as she talked about friends/boyfriends/school. And when I started getting interested in girls, she gave me lots of advice and confidence. Which I'm not too modest to admit helped me get quite a few objects of affection.

And when she cut herself off from the family three years ago, she and I kept in touch as much as we could. Tons of email and regular phone calls. We had a very open and frank relationship. We could talk about anything. Including when I started having sex my senior year, she was graphically descriptive with advice to improve my skills. And, it worked. I gained quite a reputation from the girls around school. I also have to admit that it put some really...shall we say 'interesting' mental images into my head regarding my sister and her advice. See, Josie is probably the first girl I noticed in a sexual way. And her openness about sex only made it harder not to think of her in that way. Those long legs, tight ass, firm breasts...

Anyway! I had long ago secretly decided to follow in my sister's footsteps. The big city sounded amazing. And thanks to the encouragement and help of my sister, not only did my grades merit being accepted into NYU, but they included scholarships that would make my education nearly free (of course, being a State track champion didn't hurt). Which was great news, since my parents were going to pretty much disown me if I left. And if that didn't do it, the fact that my sister not only offered up staying at my place, but insisted, certainly would.

And here I was. Crowded city airport far from my old home; a place I would likely never be welcome again. But that was alright. The second I came out of the terminal, I was greeted by the beautiful voice of my sister, calling my name seconds before I was caught up in a big hug. I received a big kiss on the cheek before she pulled away and held me at arms length. She looked me up and down, as I had done quite a big of growing in the last three years. While she took me in, I did the same to her. The long legs I mentioned earlier stood atop two inch heels, bringing her nearly to my 5'11" height. A business-like skirt ended just above her knees. A powder blue sleeveless sweater hugged her waist and chest, with the collar of a golf shirt poking out the top. Shoulder length blond hair framed her face and a pair of glasses perched on her nose were windows for the soft blue eyes that scanned my figure. This all happened very quickly before Josie spoke.

"Brian! You look great! And it's so wonderful to see you!" She exclaimed and hugged me again. I caught myself noticing the smell of her hair.

"I look great? What about you? You're amazing!" I said back. It was true. She was turning out to be one of those women that got better with age. She had been great at 22 and had somehow managed to get better.

"Flatterer." She said as she broke the hug again. She had a sly grin that told me that she knew damn well how good she looked. But at the same time she was happy that I thought so.

We got my other bags and hopped in a cab, which I should point out was my first cab ride. As we headed towards Manhattan, I gaped open mouthed while looking out the window. Josie pointed out various points of interest. Even so late at night, the city was so alive. I knew I was being a total yokel, and I could see my sister's bemused smile reflected in the glass as she watched me. When we finally pulled up to her building, we were greeted at the door by an actual door man!

"Good evening, Miss Stevens." The well groomed man said, as he held the door open for us. "Can I help you or your gentleman friend with the bags?"

"We're good Arnold." She smiled back at him. "And this is Brian. You'll be seeing a lot of him in the future." He gave me a look which seemed to say 'You lucky dog'. I found it odd that she didn't introduce me as her brother.

While we rode the elevator up, Josie readied me for her roommates. "Now, remember, Esther and Denise can be a bit...gregarious. And they certainly aren't modest. So don't get all embarrassed or shocked by what they say or do. And you'll have a hard time offending them so don't get uptight. Just be yourself. They'll fall in love with you in no time." She smiled sweetly.

"Got it, sis." I replied, steeling myself for my first meeting with Josie's two best friends. I had heard much about them, but never actually met them so I didn't know what to expect. With what Josie had told me the options ranged from between them answering the door naked to greeting me with a kick to the groin.

We exited the elevator, dragged my bags to her door and she unlocked it. From the couch bounced two figures of loveliness. And when I say bounced, I mean it. They both possessed the kind of bodies that even after the main body had stopped, other parts continued to jiggle and sway.

I knew the dark caramel creature was Esther. She wore pajama shorts and a lacy bra that hugged her wide hips and full breasts wonderfully. She gave me a sultry look from her almond eyes. Denise was originally from eastern Europe. She smiled a dimpled smile, like some girl next door. But it was hard to focus on the smile with the enormous pair of boobs threatening to rip through her over-stretched t-shirt. Even though I knew who was who by Josie's descriptions, she introduced us anyway.

"Girl," Esther exclaimed "You did NOT tell us your brother was such a hottie." I felt my face flush.

"Oh, so cute. He's blushing." Denise commented, her voice containing a hint of accent.

I dropped my bags and nervously extended my hand, to shake theirs.

"Oh, I don't think so." Esther said indignantly before pushing my arm aside and enveloping me in a hug. Her big tits squished against me and I felt a stirring in my jeans. When she pulled away, Denise immediately took her place. Her larger bust changed my 'stirring' into 'full speed ahead to erection'.

"Thanks for staying in to meet him, girls." Josie said to her friends.

"There was no way we were going to miss it." Denise beamed.

"As much as you talk about him, we kinda had to. Besides, you're gonna pay us back by letting us take this hunk out on the town tomorrow night." Esther laughed. I blushed again. And then all three were giggling at my reaction. Thankfully my sister came to the rescue.

"I think, ladies, that my little bro has had a long day. A full morning of our family giving him hell and a long flight. I think he needs a full night's rest before he can handle the two of you." This was met with a chorus of 'boos'. Josie just waved them off and pushed me and the bags towards a room.

"Goodnight, studly." Esther called after us.

The room turned out to be my sister's. It was huge, which was saying something for a place in the city. I plopped my bags in a corner and started looking for a blanket. Finding one, I began making a bed for myself on the floor.

"You're kidding, right?" My sister snapped.

I peer up, over the bed at her. She was changing into her sleep attire. Her blue top replaced by a small baby tee that ended just below her apple sized breasts. She was shimmying out of her skirt, revealing white cotton panties. Now, modesty isn't something you can afford in a family of 7 people, but the sight before me caught my breath in my throat. And it refused to come when I realized that Josie wasn't going to be putting anything on over her panties. I have no idea how long I stared before my voice came back.

"Um...sorry. I can take the couch. I just didn't want to be in any one's way in the morning." Josie gave me an exasperated sigh.

"No, silly. I have a king sized bed. More than enough room for the two of us." With that she plopped down onto the bed and patted the side next to hers.

'What the heck' I thought. It's not like anything was going to happen. I would just have to be sure not to poke her with my morning wood, and everything should be fine. Feeling exhaustion creeping up, I quickly peeled my clothes down to my boxers. When I turned to shut off the light, I noticed my sister staring at me. She looked at me intensely, before shaking her head slightly and then smiling broadly. 'What was that about?' I wondered.

I crawled into bed and faced my sister. In the low light I could see her blue eyes gazing at me, a soft smile on her lips.

"Brian, I'm so glad you're actually here." She finally said, bringing a hand up to caress my cheek.

"Me too, sis. I've really missed you." her smile widened.

"I missed you too." She said softly. Then she moved toward me. I expected a kiss on the forehead or cheek. To my surprise she kissed me on the lips. It was soft, but lingered far longer than a simple peck. When she broke, she simply said "Sleep tight." closed her eyes and sighed.

That little kiss...a kiss that couldn't have lasted much more than a few seconds, kept me up on and off all night. I knew that I was reading too much into it. I mean, not only was she my sister, but she was an older woman...and way out of my league. And why was I even considering whether she was in my league!? I know I have always had a crush on Josie. And honestly, more than once had thoughts of her come up when I was masturbating, but I knew it was wrong...wasn't it?

I woke up on and off all night thanks to a combination of sleeping in a new place and the presence of my sister next to me. I could hear her breathing softly as she slept. A couple of times I lifted up enough to look at her face. That same smile was on her lips. She looked so content. Sometime in the early morning I think I finally drifted off to real sleep.

When I woke again, the sun was up. Josie was softly calling my name and gently rubbing my chest. I opened my eyes and saw she was dressed in business attire, sitting next to me on the bed.

"Sorry to wake you, Brian. I just wanted to make sure you remembered that we all have work today. So you'll have the house to yourself. Keys are on the counter and Arnold will help you with whatever you need." She whispered and then bent to kiss me on the cheek. I made note that it was only on the cheek...and that I was disappointed about it. And she bent lower and whispered in my ear. "And kudos on your tent making skills. Very impressive." Then she giggled and left.

Still half asleep I pondered what she meant until I realized I was sporting my usual morning erection. I felt like I should feel embarrassed, but part of my brain was convinced that she hadn't been kidding about being impressed.

Now that I was awake, I got up and used the bathroom, willing my erection to go away. Assuming that everyone was at work , I stumbled out to make myself breakfast. It never occurred to me that people might leave for work at different times. When I stepped from my room, seconds later Denise stepped from the bathroom she and Esther shared. She had a towel wrapped around her hair, and nothing else. Her enormous breasts, looking so much bigger because of her tiny frame, swayed hypnotically before they disappeared into her room.

"Need help picking your jaw off the floor, sugar?" I heard a voice ask. Esther was coming from the kitchen, dressed for work. Josie had told me that Esther was a teacher. I could now see that she was the kind of teacher that none of the male students heard one word she said, since all their blood spent the entire class in their crotches. On a normal woman it wouldn't have been so bad, but her full hips, gorgeous ass, and plump breasts pushed her outfit out in all the right places. And, even though she hadn't been wearing glasses the night before, she was now. It completed that whole "naughty teacher" look. I could only guess that she enjoyed teasing her students like she seemed to enjoy teasing me right now.

She had her books and bag gathered, obviously heading toward the door. As she passed, she glanced down at my crotch, and smiled slyly.

"Your sister wasn't exaggerating." she said in a husky voice, and slinked out the door. Dammit! The combination of a naked Denise and Esther's sexy, hip swaying walk had put me at full attention again.

My brain started working , and I made my way to make breakfast. About ten minutes later I heard the sound of a door slamming. "I'll see you tonight, Brian!" called Denise. And then the front door slammed. And I was alone.

I spent the day mostly vegging out. The girls had a gym, so a spent an hour on the elliptical, but for the most part I watched TV. Josie had about a hundred times as many channels as back home. And some of them were the racy kind. Which, combined with my run in's in the morning had me stroking one out in no time. Actually, it wasn't one. Over the day I did it four times. It got me to thinking that staying here was going to give me carpel tunnel syndrome.

Since she was a teacher, Esther was the first one home. She greeted me warmly before leaving to change into something more casual and then returning to keep me company. We chatted about this and that, nothing too deep. I noticed that, while still flirtatious, she wasn't anywhere near as intense as she had been this morning.

Denise came home about an hour later and joined us. Where Esther was blunt and saucy, Denise was bubbly. She laughed easily and often. The two of them were definitely making me feel more at ease. And their combined flirting was giving my ego a big boost! And they kept it light enough to keep me from going all shy on them. I mean, I'm not usually shy around girls my age. Josie had long ago given me confidence in that area. But these were highly attractive, more experienced, city women. After a while, the ladies told me to get changed, since they were taking me out on the town.

I was of course, dressed first. Denise later emerged wearing a pair of painted on low rider jeans and a white top that resembled a fancy tube top, or maybe a corset. It started just below her nipples and ended just above her sexy little navel, showing off the disparity of her tiny waist and her enormous chest. She had cleavage for days. She posed for me for a second as I gave a long whistle, as she flashed me her dimpled smile.

Esther came out shortly after. Her top looked like someone had mixed a button down shirt and a bra. It had see through sleeves, and buttons down the middle (which were all undone). At the bottom is scooped under and supported her big boobs, and ended leaving a large portion of exposed flesh before you came her her barely there skirt. She spun for me, causing the skirt to fling out a bit and show off her black thong. Denise giggled as my eyes bugged out.

Not long after we were all ready, Josie returned home. First to leave for work, last to get home. That was just like her. But that's also probably why she was doing as well as she was. She looked really stressed as she came in the door and plopped on the couch.

"Josie," Esther started, seeing my sister's state. "Don't you be like that. We're going out tonight, remember?"

"I don't think I would be much fun. We had a really bad screw up that I had to fix, and I'm definitely not in a good mood." I could hear the edge in her voice.

"Oh, poop!" Denise cried. Even her curses were cute.

"Don't worry D, she's going. She's smart enough not to leave us alone all night with her handsome little bro." Esther grinned. Josie glared at her. Clearly not in the mood for games.

"Ladies. I think I might be able to solve this to every one's satisfaction." I declared, as an idea came to me. As I mentioned, Josie gave me lots of advice on women. And I took them to heart Some of the advice I just picked up from hearing her complain about her various boyfriend's short comings.

I got up and sat on the back of the couch, behind my sister, swinging my legs in either side of her. She tilted her head back and looked up at me quizzically as I grinned down at her. Then I gently pushed her head forward and took hold of her shoulders and started working. You see, I long ago picked up that women dig massages. So I checked out some books from the library and practiced on any girl that would let me. And I had a lot of practice.

Josie's back and neck were all knotted and tight. Under my ministrations however, it only took a few minutes before a contented moan escaped her lips and she visibly began to relax.

"I have never seen anything calm her down so fast." Esther said, in awe. "You must have some magic hands!"

"God," Josie groaned "He sure does."

"Me next!" Denise laughed, bouncing up and down. I had to focus extra hard on the task at hand or risk drooling on my sisters shoulders.

After a good fifteen minutes of work on her shoulders back and neck, my sister's sweet smile returned. Mind you, she didn't say she was done, but her friends noticed and rushed her off to get ready. I think they were only halfway concerned with her getting ready. The other half was them wanting a turn.

Denise went first. I had to alter my pressure as she was a fair bit more delicate than my sister. Not to say my sister was big. But she definitely worked out, and was nicely toned. Denise seemed very soft. Especially the twin orbs I now had an aerial view of. I felt like if I fell forward, I could get lost in her cleavage. She purred the whole time and even eventually started stroking my calf as I worked.

Esther butted in, making sure she got some time. After about ten minutes, she spoke up.

"You know Brian, if your hands work this good on places other than shoulders, you have a free pass to my bedroom, anytime you want." Denise gasped at her friend.

I'm not sure where it came from, but I think I was building my confidence under the assault of Esther's rather direct flirtations, so I responded "I'm not sure you could handle it, Esther." She turned on me immediately, kneeling on the couch in front of me and stared into my eyes intently.