It was a tumultuous time in my life when Anna came along. I had just separated from my wife of only three years, of which the last six months had been hell on my emotions. We had had a very outgoing sex life, and in the end that’s what probably cost us the marriage. We had a pretty wild ride, but in the end my ex wanted more than I could ever provide, both financially and sexually. So I licked my wounds, got out while I still had some sanity left, and vowed never to commit myself like that again. I devoted my life temporarily to getting back on my feet and enjoying life again. On the positive side, I did learn a new appreciation for the female form that I could now take with me to my grave. That’s where Anna came in.
She had started working for us in the heavy truck business the summer I got married. Fresh out of high school, she had taken the office assistant job to help save some money for university and to take a break from school, period. Needless to say, the fresh face was welcomed at our place, as most of our clients consisted mainly of overweight truckers who, on some days, smelled like they had been drug through the manure pile. Now, the trucking business is no place for a petite little blonde, but Anna took all the strain and sexual comments in stride. Hell, even giving back as good as she was receiving some days. She seemed at first to be overly friendly, but after a while, it was just taken as second nature by all of us. That was just her – outgoing, good-natured, and sweet, a stark contrast to the clothes she would sometimes wear. Mostly she wore flowered dresses and flats, but every once in a while, she got somewhat daring with high-cut skirts and loose fitting blouses that showed plenty of cleavage. I had to catch myself sometimes from staring too long at her (she was only 18 at the time) but some days I couldn’t help it. It usually would lead to a raging hard-on by days end, which ultimately led to a first class fucking when I got home to my ex-wife.
Now, I’m not overly attractive, I smoke, and have a very average body, but my shining feature is my height. I’m 6’8” and I feel it has gotten me the lay when the other features didn’t seem to carry me through. I used to believe that I was gentle and caring, but a soured marriage will cure that quicker than anything. I was now looking out for number one, and that included women. Most of my experiences since the separation had consisted of liquor-induced lays, which ended as soon as the sun came up. That was until Anna and I took our working relationship to a more personal level.
In the months following the end of my marriage, I began to notice that Anna was developing into a beautiful, young woman. Gone were the last remains of her childhood features, replaced with softer, more feminine curves. Her breasts had grown at least two sizes, from a shallow A cup to a full 34C. Her legs, somewhat gangly and awkward-looking before, now were toned and muscular, no doubt from a little exercise. At 5’3” she was a lot of woman in a small package. I’m sure she was aware of the changes as well, but with Anna she seemed to be hiding it more than showing it off. I’m sure this may have been due in part to the fact that most of the women in our office were older and more professional, so my guess was that she had been told to tone down the outfits, much to my disappointment. Now twenty-one, she had matured beautifully, and I didn’t feel as hesitant as I had in the past to look at her in a sexual way. At twenty-eight, I could hardly be considered an old man to her.
During the summer, Anna’s skin took on a warm, golden glow as she must have spent some time in the sun, being a very out-door person. This year it seemed to bring out her sexual prowess more than ever before. She had become good friends with our department assistant Deana, and the three of us usually took our coffee breaks together, having a cigarette while talking and joking about the quirks of our jobs. Deana is also in her late twenties and a very outspokenly sexual person, so most of the talk is usually about just that – sex. Deana and I had had some pretty risqué conversations before, so it didn’t take much for Anna to be included in on them as well. As time went on, I’d found myself fantasizing about Anna more and more, undressing her with my eyes, wondering what she was (or wasn’t) wearing under her long dresses. I also have a very huge foot fetish, and Anna seemed to unknowingly contribute to my fetish by wearing open-toed shoes or sandals. Her feet were well taken care of, with a fresh coat of toenail polish almost weekly, with no dry skin or bunions visible. In a word - sweet. As time went on, our conversations turned more and more daring, as if we were competing to see who could make the next person blush the most. I must admit that I learned a lot about Anna in just a few short weeks. This inevitably led to us becoming closer, and we flirted with each other endlessly. I never expected it to go as far as it did one night two weeks ago.
I was scheduled to work my normal Tuesday night shift but at the last minute, I switched with a co-worker, which meant that I got a Thursday night shift. I didn’t mind at all though, as that is the night that Anna works late as she has some prior commitment Thursday morning, which means she doesn’t start until noon and then works her normal eight -hour shift. For some reason this evening Anna was more daring and flirty than before. She was wearing a very conservative black flowered summer dress topped off with a white suit jacket and her normal open-toed sandals. But after the last of the ladies had left for the day she took off the jacket, revealing the top of the dress with only spaghetti straps, allowing me a generous glimpse of her ample cleavage. I found it very hard to concentrate on finishing my work when she came down for a smoke as she sat down beside me at the service counter, constantly crossing and uncrossing her legs right in front of me. We made small talk in between customers, and once again the subject turned to sex. For some reason Anna was more forward with her questions tonight. I tried my best to top her comments, joking about her forwardness, but she seemed to be on some sort of mission this evening. When we started talking about tattoos I almost lost it. She had recently gotten one on her right breast and wanted my opinion. As she peeled down her dress to reveal a small rose with a large thorn with a drop of blood on it, my thoughts were confirmed – she wasn’t wearing a bra. As she talked about how much it hurt to have the tattoo done in that tender area, she caught me gazing down between her breasts.
“You haven’t heard a word I’ve said, have you Steve?” Anna blurted out, her deep blue eyes looking directly into mine. It was at that moment that everything that I tried to do to keep my cool went out the window. Here I was, with this blonde Mira Sorvino look-alike showing me her tattoo on one of the most sensual places of her body, and I was looking for more. I hesitated a bit, not sure of what to say. Then a rush of boldness overcame me.
“Yes, but I was just wondering what the rest of that beautiful cleavage looked like.” I couldn’t believe that the words had left my mouth as I spoke, but there was no turning back now. As I braced myself for a slap, I was very un-prepared for what happened next. Instead of feeling the hot sting of her hand, Anna grabbed my crotch and smiled wickedly.
“..And I have always wondered what
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