Right Time Wrong Girl

My name is Ben and I am a well paid software designer that gets placed all over the country by my multi-national tech company. This job suits me perfectly, I am single and have nothing anchoring me to a single location, and moving around is highly beneficial financially. I am a pretty handsome well toned guy, and I never have any trouble meeting new ladies.

Last year I was placed in a coastal town, in a rural area, with a thriving social scene. A beautiful part of the world, I settled very easily, and began to enjoy the local bars and clubs early in my stay, with numerous romantic interactions that never really went anywhere.

After a month working in the large office I was assigned to, I began to flirt with two attractive local girls. One of them Shauna, was a statuesque tall exotic model like vixen with a feisty attitude and flawless smile. She was of Arabian descent, and looked and dressed with amazing elegance. She was fun to be around, and I was the envy of most of the office, when we began lunching together each day. Then there was Katie, a dreamer, an artisan, a drifter. She was involved in a casual relationship with one of the other guys in the office Simon, a guy who I considered to be way below what I'd imagine her standards would be. Far less classically attractive than Shauna, Katie was short, carried a few extra pounds but had magical eyes and lips, and a jaw dropping set of breasts that although I never had seen in the flesh,. I fantasized about daily. She would dress far more leisurely and was a bit of a tomboy. She made it clear to me right away that she was attracted to me sexually, and that she was willing to take it to the next level whenever I was ready.

I took the ego choice, cooling off with Katie and made arrangements for a dinner date with Shauna, she would give me the greater status boost, which is something that I crave when being in new environments.

Following our date, it was clear Shauna was smitten with me, and we quickly arranged date two, I was to cook for her in my luxury apartment. She arrived late, and I was really angry with her, patience is not my finest trait. I was off with her and she knew it, to win me over, she began revealing more of herself. Every time I would leave the room, she would look even more sparsely clothed. It was clear to me, that our first time was going to happen then and there. Our conversation became more and more sexually orientated, until we came to the subject of our ultimate fantasies. My one I recalled was having sex with physician after an intimate examination, she revealed that she absolutely loved to watch men strip. I am not sure how truthful she was being, but it was clear that it was a signal to me, and I wasn't going to miss it. I took her hand, and guided her to my sofa, and sat her down, I put on some soulful music, and began to unbutton my shirt. Her eyes filled with excitement, she laughed mockingly but I could see her biting her lip and that her nipples were now erect showing through her blouse. After reaching my underwear, she asked me to finish with a prop. I grabbed a chair from the kitchen and sat back on it, as I removed my shorts revealing my semi-erect penis, which clearly startled her. "Nice cock" she nervously acclaimed. I am pretty well endowed, and I could immediately notice a change in Shauna's scent as I approached her.

She was stiff as a board as I placed my hands on her shoulders and started to undress her. I kissed her gently, and I could feel her breathing begin to become deeper and quicker. We both sat on the couch, and after 10 or 15 minutes of groping and lip-locking, I crossed the point of new return and ventured south to her perfect unshaven pussy. As soon as my mouth reached her lips,, she groaned loudly. I realized that her sense of arousal was intense, and I knew that I could not go too close to her clit, this early. I probed insider her with my experienced tongue, I could almost drink her wetness. She was fragrant and a brilliant pink in her opening, and eating her was a pleasure, not a chore. As this was happening I became more and more aroused, and offered my ample prick to her mouth. She was very reluctant. I sensed that both the length and girth intimidated her, and decided to postpone this approach, and mounted her from behind. My cock barely fit in her. She squealed in discomfort at first, and I used my hand to guide my tip in and out of her dripping gap. Eventually as is normal, she could take almost over it, and I gently screwed her until I could feel her vagina convulse around me, she had obviously had a shuddering orgasm. I knew I had to be patient with her, and I finished by myself and shot over her perky under sized breasts.

This was a work in progress.

Over the next year, our relationship grew deeper and deeper. She told me she loved me, I never reciprocated, Shauna was fun, but she never seem to give herself to me completely, especially in bed.

She loved to flirt with other men, and enjoyed a bit of a pretty slutty image at work. I quickly realized, she loved the attention and never took it anywhere. Until one night at the local bowling alley. About a dozen of my colleagues had arranged to go out with work, including Katie and Simon.

By this time, Simon knew that Katie had a massive crush on me, and was resentful and bitchy towards me. He clearly fancied Shauna, and Shauna loves any sort of attention. He asked everyone if they would like to go outside for a cigarette but only Shauna accepted. Before I knew it, they were going outside every 10 minutes. I was pissed off by this, it looked suspicious, Katie whispered to me "this is fucking bullshit". Although not officially dating Simon, she was clearly upset by Shauna encroaching on her territory.

At the end of the night we all went our separate ways. My ego had been hit. She was clearly heavily flirting with a guy far less good looking than myself, and with about a third of the charisma.

That night, I slept in a spare room after a heated argument. We quickly made up, and resumed our fairly mundane sex life soon after.

A week later, I had an instant message from Katie. Without his knowledge she had access to Simons Facebook account and sent me screenshots of messages with him bragging to his friends about kissing Shauna, and how she had sent him some half naked photos. He also told his friend, how not only had he been fucking Katie, who I clearly fancied, he had also slipped the tongue to Shauna, and that must mean I am a complete fraud. "Handsome, witty, and rich but no sex appeal to women is the actual quote." He clearly felt the bigger man.

I was extremely angry, and decided that I needed to teach Shauna a lesson for allowing this humiliation. After several hours of Katie pouring her heart out to me about how she really could not stand Stuart, I invited her to view my webcam. I said I want to show her my tattoo. She was in total shock when I appeared on her screen, naked holding my massive veiny erection in my hand. I am not normally so sleazy, but had become aroused thinking about her as we chatted.

Her sense of disbelief didn't last long, she activated her cam also, pretty soon she was playing with her massive tits, I could see one hand was heavily involved elsewhere also. They were enormous, and so well proportioned. I learned so much to have my cock slide up in between them.

We spent at least an hour masturbating in front of each other. All of our previously unspoken chemistry came out at once. She used a strange looking purple toy, and allowed me to hear her moan and cum over and over.

She was very different to Shauna, Katie was comfortable with her body and it showed. Even though she was flawed, her flaws were sexy, and I became instantly aroused in her presence.

The next day, we flirted on e-mail all day at work. We knew we had to meet. That night we parked both our cars in a country park, she came and sat in my car, and quickly began unzipping my jeans, and placed her heavily glossed lips around my flaccid member. After what seemed forever, of her running her lips and pierced tongue along my length, I put my seat back and gave her room to climb aboard. Straddling over my now pulsating eight inches, she lowered herself up and down my shaft, making sure she let me know how much she appreciated my every inch. After roughly 20 minutes I gave her every ounce of spunk I had, which she swallowed loyally. None of this prudey bullshit, that Shauna had more and more delivered over the last year. We both made it an unspoken truth that we wanted to consume each other's sex fluids, and we both did so hungrily. We met and fucked every single night for the next month. It became harder and harder to cover our tracks. So eventually I just admitted to Shauna, that it was over between us.

Shauna was irate, and for the next year she made my life hell. Vandalizing my car, and spreading false rumors about me in work.

I laughed my ass off when Katie sent me future messages Simon had sent Shauna, trying to take their relationship further. She called him a tiny-dicked loser, who she had just used to make me jealous.

I felt bad that I had believed Shauna had more blatantly betrayed me, but relieved that I had finally realized it wasn't going to last with us.

Katie and I have recently moved in together and are very much in love. I have extended my contract, and am finally settled in this town.

This is the first time I have communicated this story, and I hope it will be cathartic for me. I still hate myself, for making the wrong choice in the first place, and regret not being more clear about my feelings to Shauna earlier on.