The Midwest Apartment

My hope is that you will enjoy this story and your comments are welcomed.

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Stranger events have happened in my life but this one is the one I want to tell you about. My name is Julia, I'm thirty eight years old, work as a mid level executive for a prestigious insurance company. I've never been married and frankly I'm not that interested in marriage. I'm financially capable of providing for myself and do quite well at it. I have a good life with most of any social activities being related to work functions. A few months ago I accepted a major promotion and relocated to the head office in the Midwest. The new penthouse apartment I purchased with by the way is 2000 sq feet on the 23rd floor in downtown Chicago. The view of Lake Michigan and part of downtown is spectacular with many conveniences right there in the complex, including a workout center, pool, sauna, and many other amenities you could expect for residents use in an upscale luxury complex.

My penthouse was just a few blocks away from the office and I usually walked it on nice days. The location was perfect and close to everything I would ever need. After the third month in my new and apartment and new city, I began to feel lonely, especially some of those nights when I had little going on. The weekends were usually pretty busy with corporate functions and promotions that keep me traveling and otherwise keep me too busy to feel alone. I have some acquaintances here in Chicago both male and female, business associates, but like anything else, we all get busy and after only three months, I've not had time to form those long lasting friendships yet. It was on one of those lonely nights while scanning the hundreds of TV channels and finding absolutely nothing of interest to watch that I considered the idea of having a housekeeper and boarder around, not that I needed the income, no not that, more or less just have another real life person around from time to time. At least back in Charlotte, I could always visit with mom or hang out with close friends but now, living in Chicago things are different.

The idea of hosting a college student live in appealed to me even more after one of my employees mentioned that her neighbor's daughter was looking for a place to stay closer to campus. Amanda, as was her name was currently commuting to school and had she realized commuting from the suburbs daily to attend school in downtown was this difficult, she may have chosen another college since her parents were unable to afford the additional cost of housing to live on campus or downtown. I learned that her parents were barely making ends meet and it was difficult for them to even pay for tuition so I thought that this could be something I could do to help someone out and I would gain a companion to help keep my sanity. I pondered the idea for a few days and realized that it was a win situation for both of us. After some consideration, I made the offer to pay Amanda a nominal fee for doing laundry, running errands and tidying up around the condo, not that here was really much to do but she would still be a welcomed help. The arrangement would be convenient for both of us.

When Amanda came to stay her routine was to tidy up or clean up around the condo, do some light dusting, do laundry, mostly undergarments since almost everything I wear is dry cleaned, run errands to the cleaners, and the likes of that. On those days that Amanda came over, it was convenient for her to stay the night. She basically stayed two or three nights a week and for those nights and headed home for the weekends. I set up the spare room for her exclusive use and in the morning, she would go off to classes but not without making me a coffee of which I began to really appreciate and look forward to each morning. Her school was a close six blocks away and in the opposite direction of my office. It was a pretty sweet deal for her all around and I enjoyed her companionship as well. The arrangement for Amanda was working well since she wouldn't have to commute the one and half hours each way for school every day and for me, it was very convenient since most nights Amanda would have diner started and looked after most other things I would have had to do. After a while I began to enjoy this pampered lifestyle. Not only was I able to help someone out I thought, but realized I was actually a very lonely woman at the time and knowing that I had some other interaction on a personal level and not business related was comforting to me. Looking back now, I think Amanda had been the little sister I never had.

Amanda had just turned 21 and I can't say she was a very attractive girl but she was certainly a very nice girl. She was quiet, a little timid, not the party type, studious, and well mannered. She was short, maybe 5'4", a little stocky but well proportioned, certainly not the type of girl that should be wearing low rider jeans but as most girls her age, she did. Amanda had a very pretty face, shoulder length dark brown hair and beautiful dark brown eyes that caught your attention the moment you faced her. Another nice feature about Amanda was her very noticeable breasts. For her height and build, they looked huge on her and were always "in your face" as they say. She was defiantly a "D" cup, solid with no droop. Ah to be 21 again, I mused each time I saw her! In contrast, I have small 32" "C" cup breasts, I'm thin, and I'm 5' 7" tall. I keep my hair short because it's easier to get ready in the morning and I suppose by most men's standards I'd be considered not a perfect "ten" but attractive enough to turn heads. I'm not a natural blond but I'd never let on otherwise.

Since moving here, my time is mostly spent around work and work related events. I have a chance to meet many new people but all of them on a professional basis leaving very little time to have a personal social life and certainly no one to have sex with. A girl can become very restless in the big city after awhile. As you might already have guessed, I have resorted to other measures. I enjoy very much to satisfy myself sexually and to the point where it has become a nightly ritual with me. I've looked forward to bedtime lately because that's when I can take the time to explore my body and bring myself to a frenzied orgasm.

I didn't know this at the time but Amanda later revealed to me that she didn't date very much, actually not at all. Her early sexual experiences with boys were not pleasant either. When Amanda was eight years old her girlfriend's brother forced her to give him head or do drugs during a sleep over. That was the event that disgusted Amanda the most about boys. In high school her dates were not pleasant either. On one occasion during some heavy petting her boyfriend at the time hurt her while fingering her. He insisted she should give him a blowjob but she didn't and ran away in fear. Amanda felt disgusted by the whole experience and gets disgusted at the sight of a penis. Since then she has resorted to self-stimulation. Over time her friends saw a change in her and didn't quiet understand her or how she felt. Shortly after she was off to college and lost touch with most of her friends. As a result Amanda has not had a meaningful relationship with any boy and had some trust issues with men as whole. In high school Amanda's social life evolved around sports and school and now in college, it evolves around her studies. Like I said, I didn't know all of this at the time but had I know perhaps our relationship would have developed sooner.

This new living arrangement was working out quite well for Amanda. She had the freedom of being out of the house and sort of on her own on some nights while also being closer to school and saving herself the commuting time and money to get to school. In exchange for Amanda's help around the apartment, I would pay her a small nominal fee and of course a place to stay in town. I was thrilled by the idea of having a live in maid and basically not worry about anything else but work or freeing up my time to do whatever I wanted. I was even able to get in a few workouts and brisk walks around downtown.

The only draw back to all of this I thought was that on those nights when Amanda would stay over I would have to be careful and remember not to walk around the apartment semi nude as was my habit. I loved walking around in just panties. The main view of my master bedroom balcony was Lake Michigan, it was private enough that no one could see in. Of course if you were flying overhead in a plane I guess one could see looking down but that's unlikely. I've never had any complaints. Sitting out in the balcony sipping tea in just panties or completely nude on a warm summer night was so relaxing that I would sometimes doze off to sleep. On occasion I would even masturbate out there and on a clear night there might even be a star or two trying to peek through the lights of the city. Now with Amanda here I kept forgetting I wasn't the only one around anymore. I had to also be very discrete when I masturbated in my own room so that Amanda wouldn't hear me. Other than that, the arrangement was working well. As I got to know Amanda better throughout the school semester, we had become good friends and companions for each other. Many times I would help her with her research papers and we chatted about things as two close friends would. I enjoyed helping her with her studies because I was learning a lot as well but I think the real reason I enjoyed tutoring Amanda was that I had a perfect excuse to be in very close proximity to her and I realized I was beginning to enjoy the physical closeness. As goes in any conversation among friends, it migrates to the subject of sex. I noticed whenever past sex experience conversation came up she would remain quiet and not really discuss it. I never pushed her to talk to me about it and I didn't talk to her about my sex life. Like I really have a sex life anyway unless you consider self-satisfaction on a regular basis as a sex life.

Within a few weeks I could sense there was something different about Amanda but I couldn't put my finger on it. I figured that she was just more relaxed around me now that she got to know me a little better but I became aware there were times when I would catch her staring at me but I didn't let on I knew. While sitting close to her during our tutoring sessions I would steal glances of Amanda's breasts and take in her body with my eyes. At times I would stand up next her while she was sitting looking over her shoulder at her work and I would enjoy looking at her and bending down to point out some correction or something. From my vantage point I was always able to see her large breasts and the deep cleavage of her mounds through her tops. I don't think she had any idea I was checking her out. On the other hand, I had no idea prior to now that I would be interested in even checking out any other woman at least in a sexual way so this was a new twist for me.

On one occasion I had just gotten out of the shower and slipped into a robe. We were sitting at the table having a cup of tea and looking over a school assignment as was our custom now to do just before bed, when I caught Amanda staring at my breasts. I casually looked down and noticed my robe had opened up enough to expose most of my right breast and a good amount of skin. I never gave it much thought at the moment and casually covered up and continued our chat. Not that there is much to see there anyway I thought to myself.

After that evening, I noticed Amanda began to wear her robe for our evening tea and homework review instead of her usual sweats. Secretly I preferred it that way and was pleased to see that she was more relaxed and casual around me. Seeing her two large breasts in a thigh length robe was a pretty sight and I noticed right off that she had to constantly keep her tight fitting robe from opening up at the breasts or from riding too high up her thighs as she sat. I remember thinking how sexy she looked, and since she always sat across from me, the only time I could get a good glance at her nearly fully exposed thighs was when I got up to freshen the tea pot or when I was standing over her shoulder reviewing her assignment or something like that. Then I was able to steal a good look at her without being conspicuous. I found myself wanting to steal any opportunity I could to sneak a glance and I was surprised at my rising interest level in this newly discovered fantasy. To the extent that I would do silly little things like getting up often to get the milk in the fridge or more sugar, or whatever I could come up with just to give me an excuse to get up and in turn, steal peak. I even turned it into a private game as to what I could do to see more of her exposed body without getting caught of course.

As time went on, I questioned my motives and why I enjoyed checking Amanda out. I wondered why this new peeping Tom thing I was playing had turned me on and I found myself even thinking of her at night when I lay in bed with my fingers caressing and plunging deep into my pussy. I wondered what it might be like to actually have my pussy licked by her. These were crazy and different thoughts than what normally goes through this mind of mine because apart from a little petting in college with another girl, I hadn't really thought about having sex with another woman. Looking at another woman in a sexual way and especially with a girl almost half my age had now become a constant turn on for me these days. The more I thought about my options, the more appealing it became and the more the more intrigued I was at the thought of further exploring these new felt feelings.

On one particular night I had the tea ready by the time Amanda had finished her shower. She emerged into the kitchen wearing her thigh length robe, I poured her a cup and passed her the cream. We chatted about school and work and all the while as she moved and squirmed about in her chair, her robe would open more and more as if her huge breasts were on a covert mission to escape the confines of her tight robe. Feeling rather bold this evening, I decided to take this a little further. I purposefully did not adjust my robe and hoped that it would open on it's own to reveal my small but sexy breasts, but on this night I had done too good of a job tying things up. I excused myself and went to my bathroom so as to adjust things just perfect. By now my pussy was damp at thought of my devious plot. I emerged back in the kitchen in less then 30 seconds and sat back down across from Amanda. This time I knew my robe would slowly open and I would pretend not to notice. Amanda sat there across from me carrying on her conversation as if nothing was going on but meantime my pussy was getting wetter and wetter and I knew that tonight, when I alone in my room, my fingers would be busy giving myself one hell of a cum bath.

Amanda's robe was eventually doing what I had hoped it would do. Open more and more, and slowly with each of her movements as she reached for the sugar or milk and just plain squirm about on her chair and spoke in her animated method of arms and hands moving about, I watched attentively but not to be obvious. I on the other hand realized my breasts were partially exposed and felt accelerated at this new voyeurism game I was engaged in. I realized that Amanda had noticed my partially exposed breasts as well for she kept darting her eyes from my breasts to my eyes and back again as we carried on our conversation, and I'll be darned if I could remember what the heck we were chatting about but it wasn't important anyway. With all that was going on, my mind was reeling with excitement and I felt myself actually cum. What a turn on! I thought and what kind of a pervert was I becoming.

Then just out of the blue my thoughts were refocused, "Julia, you have a nice body" I heard Amanda say. "My mother is about your age and you look, .............well......., you look so much sexier than she does." Amanda told me, and I sensed her relief after she said it as if it took all she had to blurt that out.

"Well thank you," I answered in amazement and surprise. "That is very sweet of you to say that Amanda" I said and returned the compliment with "and you're pretty sexy looking yourself"

"Now that we're on that subject, and in case you hadn't noticed that your breasts are almost out of that robe of your" I told her with a big sly smirk on my face and she looked down, "I think you have a nice set of breasts that most woman would envy to have"

Amanda still looking down and now covering herself blushed and thanked me for the compliment.

We both looked at each other and laughed at what had just transpired.

"No worst than you show off" she joked, and she pointed to my breasts and laughed nervously as I looked down at my own breasts but made no attempt to cover or adjust.

"You knew my tits were hanging out and you didn't say anything?" she asked jokingly.

"Nope! I hadn't noticed" I said kidding her. "The truth is I liked seeing them peak out from time to time, they are so much larger and firmer than mine" I told her, "I've always wanted bigger breasts and besides I wanted to check out what I didn't have."

Again we laughed about it.

There, the ice was broken I thought but I may have gone too far and I immediately regretted saying what I said.

Amanda's face went beet red!

"Are you blushing? I'm so sorry Amanda", I told her, "I didn't mean to embarrass you."

Amanda raised her head and looked at me, "I'm not embarrassed" she said. "The truth is that I like it when you compliment me and I liked your compliment just now." and trailed off saying "I wish my breasts a little smaller, more like yours, you know what I mean?"

"Nonsense! I told her. "I think you have a great figure and tits that most woman envy. I'm sure everyone notices them, heck I even like looking at them and you should be proud of your body."

"Ya, that's the problem Julia, everyone notices them and I'm not sure I like that kind of attention, I don't think my breasts are very pretty at all." Amanda explained.

"Oh stop it," I told her in a compassionate tone of voice. Why don't you let me be the judge of that and stop being so hard on yourself."

I saw my opportunity to step this up a notch and decided that now was the moment.

Boldly I said, "If you don't mind, let me take a good look at them and give you an honest critique and I'll show you mine and we can compare." I could sense a little nervousness in her body language and added, "heck it's just us girls, no big deal"

Without waiting for her approval I opened my robe to fully reveal my small perky breasts and my Victoria Secret panties. By now my nipples were so erect that I noticed them clearly through my shear bra and they were sore. If I didn't touch them soon and provide relief, I didn't know what I was going to do.

As if in a trance and in what seemed slow motion, Amanda followed my lead and opened her robe as well. I was amazed at the actual fullness and firmness of her breasts. I knew they were round and firm but with nothing to obstruct the view they were even more beautiful than I had expected. We stared at each other's exposed breasts for a few moments and I propped mine up from underneath with both my hands and she did the same. With my index fingers I touched each of my nipples for a brief moment and quickly stopped realizing what I was doing. Amanda apparently was doing the same.

"You see Amanda! I told you, your breasts are absolutely perfect. No sags, they're firm and round...you have every girl's dream breasts."

"Look at mine" I told her, still propping them up with my hands, "mine are just plain old little droopy mounds of flesh in need of a good boob job" I laughed and noticed Amanda, more at ease now and laughing with me. I went back to sipping my tea while leaving my robe open for her viewing pleasure. This was so out of character for me, I mean I was doing what I loved to do, expose my breasts but this time I wasn't alone. It was such a hot turn on for me.