The Girl in the Blue Jean Shorts

Observations of a Sidewalk Café Girl Watcher

This story is an elegy to a beautiful young girl, who lives and works in the coffeehouse neighborhood of the City. If I were a poet, I would write a proper elegy, but I am not so this humble little story will have to suffice.

I have seen her often around the neighborhood. She wore tight-fitting blue jean shorts, with a short sleeve boat-neck blouse. Her blouse is white with blue horizontal stripes. She wore a light cream-colored open-knit sweater loosely hanging off one shoulder. That is how she looked the first time I saw her at the cafe. Who am I? Well, I'm just your average thirty-something sidewalk café girl watcher. I love the outdoor cafes that are so plentiful in this neighborhood. The coffee is good, and so is the people-watching. People reveal quite a lot about themselves when they don't now they are being watched.

Her shorts fit tight ... damn tight! The hem was folded neatly ... twice, so that the bottom of the folds were right at her sit spot ... you know ... the point where her thighs turns softly into her sweet ass-cheeks. When she bends even slightly, you get just a hint of her little ass. But, that was all fine with me since she has a nearly perfect shape in all respects. As my eyes traveled from her jean shorts upward, I noticed that she was young ... very young. She had long brown hair, and brown eyes. She had the cutest face I had seen in a long time. A friend who knew her a little told me she was nineteen. I had trouble believing that, because she looked much younger. Not that I am drawn to that mind you, but I was prepared to make exceptions in her case. The first time I saw her she was standing tiptoe in her red high-top sneakers, bent slightly over the counter showing her shapely ass to best advantage, as she accepted her drink from the barista. I uttered one word semi-audibly without thinking, "Damn!" I guess that says it all.

I made note of the time of day as she was leaving. She walked by my little café table, I removed my sunglasses, and she smiled at me. I watched as she propelled her perfect little ass on long shapely legs until it was out of sight. I had to know who she was. My friend didn't know too much about her, just that she worked and lived in the neighborhood, and she was in his daughter's graduating class a year ago. I really do have a life, and do not have the time to become a stalker ... but I was curious about her. If I were ever going to get to know her, it would be at this little café.

I saw her again on another Saturday, at the café. She was wearing the little jean shorts to which I had become so attracted. I saw her walk in to order. I got up, and standing beside her asked, "May I buy your coffee for you? I have a nice table over here in the shade." A bold move and I had absolutely no idea what her response might be. She looked me up and down, smiled and replied, "Sure! Thank you that would be lovely." Her voice was music, soft and sweet. I paid for her coffee and another one for me, and we sat at the table. Her name is Holly, and she works in a shop about two blocks from here. She is a sweet girl, and from her conversation, seems to be intelligent. I complemented her on her jean shorts, and her pretty blouse. She blushed and said, "Thank you Michael, I love wearing them. They are comfortable and cut off from a pair of jeans I loved."

"Well, you certainly have the figure for them, my dear." I continued with the complements. She then offered a reply that made me twitch a little, "They are so comfortable that I don't wear panties with them." She smiled and blushed again, realizing the over-share. We talked about her job, my job, this neighborhood and what other things we liked about the City. I asked her to dinner, but she said, "Michael, you are sweet, but I hardly know you. M-Maybe we can sometime later, but thank you."

I just had to have this girl! There was just something in her manner and poise that made her seem older than her teenaged years. Since I am nearly fifteen years older than she is, I expected to have rather limited conversation, but she was a delight to talk with. I can't say that I was falling in love with her ... maybe falling in lust! She likely accepted me as more of a peer, because I have kept in shape so I look younger than my years. I love to ride my little green racing bike from my hilly neighborhood, past the park, to the highway along the beach. It is easy to get from there, around the lake and onto the coast road. From there it is as long a ride as you want along the ocean ... my ocean!

At last count, I think there are about a billion and six things to do in and around the City, and I wanted to do some of them with my "girl in the blue jean shorts" for as long as we might still be interested in each other. I could tell that she was interested, but cautious ... smart. I had time; I was busy and could wait. I did not see her every Saturday, but when I did, she started plopping down in a chair at my sidewalk table, and greeted me with a warm smile. Sometimes I would buy, and sometimes Holly would buy.

The conversation was always lively and I spent much of my time with her, starring into her soft brown eyes. They have a fire in them ... a love of life that shows. I was getting as hooked on Holly, as I was my weekly fix of rich espresso coffee. The times she was not there, I spent at sharpening my people-watching skills. People are amazing! They are funny, troubled, hurried, and occasionally you can detect a spark of the divine ... a show of kindness or goodness here and there. It is quite common, sitting at my little table, to hear six different languages spoken on the street, and none of them English. Much of it seems to be Russian and other Slavic languages, Italian, some French, a little German and even some Portuguese.

On the fifth Saturday of our acquaintance at the café, I renewed my offer to Holly of dinner. She smiled and replied, "Yes Michael that would be lovely. Where would you like to go?" I offered her a choice of Italian in this neighborhood, or a very good Thai restaurant I knew of, a couple of miles south from here. She was quick with her decision, and said, "Oh! Italian please, Michael! I love this neighborhood and I love Italian. But you will have to order some Chianti, and sneak me a couple of sips." I laughed and replied, "I think that can be arranged, just dress twenty-one." She giggled and said she would. My heart was pounding in my chest at the prospect of getting closer to being with this lovely creature.

I was five minutes late in picking her up, since I figured that girls always need a little extra time, and it is actually more polite to be just a little late. I dressed in a white shirt sans tie, black sports coat, dark blue jeans with a slight boot flair, and black Italian dress boots. She wore a navy blue dress with a flared skirt that went to her knees, and her hair up. She wore sheer stockings, and three-inch heels. I got a lump in my throat when she answered the door. She was a vision! The nice thing about this neighborhood is that everything is within walking distance, so we walked to the restaurant from her place. This saved us from having to deal with valet parking, which is always necessary in this neighborhood. The City is only seven miles wide, and seven miles long with a population at night of about seven hundred thousand, so parking is always at a premium.

It was a nice night with the scent of eucalyptus in the air. Holly had a pretty blush on her cheeks from the short walk. I had called ahead for a table and the maître d ushered us right in to a table by the window. I love having a table by the window in neighborhood restaurants, because of the people-watching it allows ... "dinner and a show" as I like to say. In fact, I did say that to Holly, and she giggled and agreed, immediately getting the joke. Holly looked twenty-one, and the waiter gave us each a wine glass. I ordered what I consider a good, but not pretentious Chianti, and poured Holly two-fingers to start. I poured a little more for me. My lovely date noticed this, and teasingly complained, until I leaned close and gave her a whispered a reminder of her age. I would be there to make sure Holly did not over-do, so ... no problem.

She picked up her glass, I picked up mine, and Holly made a toast, "Michael, to you and to me for a long and lovely life, and to a promising evening." We clinked our glasses. I was hoping that what she meant by a "promising evening," was the same as the thought going through my mind. The conversation was as lively as always, and we giggled and laughed easily at each of our amusing anecdotes about life in the City. She was born here, but she told me that she never tires of the city. It has so much to offer. I moved here from the Midwest, and it did not take me long to realize that I was privileged to live in one of the queen cities of the world. Our dinner date went well, and I had no idea what to expect when we reached her flat. She had a little too much wine, and wrapped her arms around one of mine as we walked. At the corner, waiting for the light, she turned to me, rose up, and kissed me sweetly on the lips. Then of course, she blushed, smiled, and lowered her eyes.

When we reached her building, she did not reach for her keys, but stood facing me. This is a signal that she is open to a good night kiss. I moved in about eighty percent of the way, she moved in the rest of the way. I put my hands on her hips, and she put her arms around my neck, and we kissed passionately, right there on the doorstep. She then asked, with her arms still around my neck, if I wanted to come up for a while. I said, "Sure, but don't you have a roommate?"

"Yes, I do, but Sally is staying at a friend's tonight ... I asked her to!" she said with some nervousness in her voice.

I said, 'Holly sweetie, I do not want to take advantage of you on our first date, I can wait." She replied quickly, "Michael! I am not a virgin. I would love it if you could stay. We can make a little breakfast tomorrow, and then have some coffee at our table at the café."

I could feed that familiar twitch again and replied, "Okay honey, let's see how it goes." Her face lit up as she said, "Oh, goodie!" just like a happy teenager getting her way.

We walked up to her flat, and entered. In the City, mostly properties have an eighteen-foot front, and the apartments are "railroad flats," meaning that there is a hallway down one side, with the bathroom, bedrooms, and kitchen along one side like inside railroad Pullman cars. The hallway opens into a wider living room at the end, usually with windows looking onto a small breezeway, or garden. She put on a CD of some soft popular music, but I noticed that she had some jazz as well; a little Mingus, and some Miles Davis from what I could see. She went into the kitchen, and came back her own bottle of Chianti. Don't know where she got it, maybe an older boyfriend, or a friend of her roommate. She poured the wine; we sat on the couch, listened to the music, and talked quietly. It was not long before the glasses were on the table, and our arm went around each other.

We kissed long and passionately. Kissing her sweet little mouth like this turned me on ... this young girl that just a month or so ago was a fantasy. She has nice medium-sized breasts, which are high on her chest, like most young girls, and puffy nipples, as I soon found out. She moaned as I played with her breasts, and those amazing puffball nipples. Her skin is very soft to the touch, and warm. Those were the words that seeped into my brain at that moment ... soft and warm.

She seemed to be free with her body, and denied me nothing. I slid my hand up the outside of her leg, over the stockings, and onto the bare flesh just above them. My hand ended its journey on her pert little ass, over silk panties. I massaged her little ass, and her moans increased. She pulled back from the kiss a little, with our lips still touching, and said, "Oh Michael, that feels sooo good!" Her words were like little kisses on my lips as she spoke. It tickled, but also sent electric shockwaves through my lips. Her breath smelled so good ... so sweet, and her lips were like cream.

As I leaned back on the couch a little, she twisted her torso to continue kissing me, and in the process, her legs opened a little. I slid my hand from her ass, around to the front, and between her thighs. OH MY GOD! I was in heaven with my hands between those warm, moist, creamy thighs. Like most teenager girls, her thighs were buttery soft. I massaged her inner thighs above her stockings, and when my hand touched her panty-covered pussy lips, she broke from our kiss, and gasped. Then she moaned loudly, and crushed her lips against mine in the most passionate kiss we had shared so far. She moved her hips and opened her legs as I massaged her over her thoroughly soaked panties. She breathed into my mouth, "Oh, Michael! I love your touch, please don't stop."

After I explored her moist crotch for a while, I did stop. She gave me a puzzled look, until I stood, picked her up in my arms and headed for her bedroom, with her pointing to the proper one. I laid her softly on her bed, and crawling in after her, I saw her eyes widen into a pure, sweet and innocent, little girl look. At that moment, she had the single most beautiful face I have ever seen, and the lump in my throat returned as I struggled to breathe. She was so suffocatingly beautiful. As I approached her face with mine, her eyes slowly closed as I kissed her as softly as I knew how. We just moaned into each other's mouths as we kissed for what seemed like a very long time. I broke the kiss, stood and undressed to my knit boxer briefs. She sat up, and I unzipped the back of her dress, and with her help, pulled it off over her head. She reached back, undid her bra, and threw it on the floor. I pulled her stocking off, one leg at a time, and tossed them over my shoulder onto the floor without taking my eyes off her face.

Our eyes locked as I crawled back into the bed. She watched my thigh muscles flex, then my stomach muscles, and put her hands on my upper arms as I lowered myself onto her. I supported my weight on my arms, so that we would both have freedom of movement. I took her puffy nipples into my mouth one after the other, and massaged them with my tongue. This caused Holly to start breathing harder and deeper. I massage her breasts as I rested my hips on hers, and she opened her legs wide. We kissed as we rubbed our still-covered crotches against one another, and moaned into each other's mouths for a long time. We eventually broke our kiss, as she breathlessly said, "Oh ... Mi-Michael!"

I held her for a while until her she cooled down and her (and my) breathing returned to close to normal. I slid her panties off, put them to my face and breathed them in a little before discarding them. Then as I pulled off my boxer briefs, I was completely naked in bed with a girl that just some weeks ago was a dream to me. She looked into my eyes, softly and earnestly said, "Michael, I want you inside me."

I put my arms underneath her shoulder blades, flexing my chest muscles against her soft tits, adjusted my body between her legs, and slowly entered her. My beautiful "girl in the blue jean shorts" was completely mine, if only for the briefest of moments. I slid myself into her pussy all the way in one slow smooth stroke, and just left it there for a moment, holding it in as far as I could. She was shuddering ... I could feel it. She softly said ... in almost a whisper, "Michael, my body is tingling ... all over. Please make love to me." The only thing that occurred to my poor brain to reply was, "Holly you are so beautiful. I want to make love to you all night." I know, kind of lame, but she smiled and in the softest voice ever said, "Okay Michael darling."

I slid myself out a little, and then slowly back into her tight pussy. The friction was getting me close very quickly. I could feel her breathing faster and shuddering a little more, with my smooth strokes in and out of her wet silky pussy. I wanted to save myself long enough for her to get close. She came once while I was stroking in and out, and I was coming very close. As I started to pull out of her, she breathlessly whispered, "Mi-Michael ... you ... can ... come in-inside me. I w-want you to." After a few more strokes with her moaning and shuddering into another orgasm, I stiffened, pushed myself into her all the way and exploded into an orgasm I could feel in every part of my body. She shuddered again as she felt my release deep inside her. We lay in each other's arms, breathing hard, convulsing, and kissing. After a while, I rolled off Holly onto my back. We looked over at each other and laughed very satisfied laughs.

She said, "I'm hungry again Michael, let's get something to eat!" We rose, and headed into the kitchen. She threw on a t-shirt over her perfect teenaged body, and I pulled on my shorts again. She had a thought, and she sliced and buttered up a baguette, and stuck it in the oven, as she asked me to chop some tomatoes, onions, garlic and basil. These last two items are staples in the City; everyone has them. We continued to work in silence, and then had the bruschetta along with the rest of the Chianti. I did the pouring and kept little miss teenager's portion small.

We ate our bruschetta lustily, and drank our wine, laughing and giggling about everything that occurred to us. We were still coming off the endorphin high from the sex, so everything was funny. We cleaned up the kitchen, and headed for the shower. Holly went first, and as soon as she was in, she opened the curtain, and said, "Ah, Michael! It's sooo lonely in here, care to join me?" I was out of my briefs in a shot as I joined my little teen princess in the shower. We soaped ourselves up, and just rubbed and slipped as much of our bodies together as we could as I laughed and she giggled. I fucked her again in the shower, and we both came quickly. After we returned to the bedroom, we made love slowly for several hours, until we fell asleep in each other's arms.

In the morning, we made a breakfast of omelets, grits, and sliced kiwis. I think it was as much playtime and cooking, but it was fun and the outcome was actually edible! We decided to walk around a little after breakfast. One of my favorite places is the neighborhood around a prominent hilltop monument. The bay side of the monument descends steeply into terraces of gardens and hundreds of steps and for my money is one of the City's prettiest places. We wound around this neighborhood, and ended up at our favorite little café a half mile away. Holly was wearing a halter-top, and tight jeans, with her red tennies. As she strode over to a table on the sidewalk, every set of male eyeballs was on her ass. I noticed this and just smiled, as I went in to order our favorite coffee drinks.

Later in the day, we went back to her flat, and she changed into her blue jean shorts, sans panties, so we could drive down to the beach, and just wade and play in the inland strait running along the top edge of the City. Our favorite orange Art Deco style bridge was in the background, making this a very good place for photos of each other, her in her jean shorts, and me in my swim trunks. We returned to the car later, and drove to an isolated spot I knew of, up behind the park, and Holly quickly lost her shorts, as she straddled me and we made love to very satisfying simultaneous orgasms, with me pulsing my juice deep inside of Holly's pussy. Holding her soft and pretty little ass in my hands was amazingly arousing as I fucked her. Back at her place, I watched Holly put on another pretty dress for dinner, and we had dinner at a nice Thai restaurant.

Holly and I played and fucked as much as we could that summer, until she moved with her roommate Sally, down south. She was working on a degree in engineering (I told you she was smart). She still writes to me occasionally, but dates one or two of her fellow engineering students. My time with Holly has passed, but I will always remember that summer with my sweet little "girl in the blue jean shorts!"