Note: This story depicts scenes of straight, gay and bisexual group sex. If any of these things offend you it is not the romance for you.
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Though it was already late in the day, I still had work to do before I could head home. One of my duties as Director of Corporate Training was to oversee our biannual management trainee retreats. These two month long retreats had become an important part of the company's internal employee development program. Our rapid growth over the last two decades had created a tremendous need for good managers. My program had a record of producing top quality candidates to fill that need. The next retreat started in the morning but due to other pressing duties I had been unable even to review the participants. I made it a practice to know the people I would be working with before I met them. Fortunately due to a slowing of growth the current batch of trainees was small; three men and three women. The groups were usually fairly well balanced as the company had a strict EEO policy in place.
There was a downside to the group being less than half the average size. One of the undocumented fringe benefits of my position was the opportunities presented by trainees who were eager to go above and beyond in there effort to succeed. Extra tutoring sessions frequently led to sessions of a more intimate nature. I had never used force or coercion to gain this particular benefit. It seemed to just happen. Truth is the first time it happened I felt more like I was being sexually harassed than the other way round. Over the eleven years I had run the program there had been many trysts with future top performers in our management team. The nice thing being that once the retreat ended the relationship ended cleanly. The trainees went to their assigned locations which were generally hundreds if not thousands of miles from headquarters. An occasional email thanking me for all my help and the good times was the most that had ever come from these private sessions.
As a life long bachelor who doesn't tend to form long term relationships these short liaisons became something I looked forward to each time a new retreat started. It wasn't due to my lack of sexual relationships that I looked forward to these times. The truth is that I have lived what most would consider a rather promiscuous sex life. I tend to form more casual relationships in that area. Having multiple friends with benefits suits me best. It is the intensity of these brief encounters with near strangers that are so anxious to please that made my trainee hook ups so appealing.
As to why I have never formed a permanent relationship the answer is very simple. I fall almost perfectly in the middle of Kinsey's sexual orientation scale. I am completely bisexual. I enjoy sex with both genders equally. This was something I discovered early in life. Though I had experimented some the first real sex I had was my freshman year of college. It was a threesome. My roommate and I shared what we called back then an easy girl. The evening inevitably included some crossing of swords which served to enhance the experience for me. After a couple more threesomes my roommate and I figured out that we didn't always need a girl in the picture. It soon became clear to me that I could never commit to just one person, because that would mean giving up half of my desires.
I read the list of names of the current batch of trainees: Roger Armstrong, Sarah Bennett, Philip Castlemen, Liam Fitzpatrick, Ronda Germaine, Kim Turner. There truly isn't much that can be discerned from a name alone. At least in this case there were no gender ambiguous names. Fortunately, I was provided with a folder on each trainee that contained a great deal of information. The first one I opened was labeled Sarah Bennett. I was already acquainted with Sarah. She was a headquarters employee who had been with the company seven years. Her current position was assistant office manager for customer relations. She was being considered for a move to the CEO's office. The new position would move her from supervisory to management status. The company felt the trainee program would be a good thing for her. I figured she was not a candidate for special sessions. On top of her working in the same building I worked in she was by all accounts happily married and devoted to her family. In addition, since she was local she would not be staying in a hotel like the other participants. Although, as I stared at the head shot photo attached to the folder I had to admit that she was someone I would like to fuck. I already knew she had a killer body and very pretty face. Looking at the picture reminded me of her oh so kissable lips that I just knew gave great blow jobs.
The next folder was that of Roger Armstrong. He was 26 and had just finished four years in the Marines. His head shot showed his blond hair was still cut to Marine regulations. His blue eyes sparkled at me from the folder. His description indicated that along with his handsome face came a buff body. I was sure I would enjoy getting naked with him. I was equally sure that despite his single status he wouldn't be into same sex play.
I tossed aside Roger's folder and picked up one marked Liam Fitzpatrick. His green eyes peeking out from a face partially covered by a mop of untidy brown hair immediately caught my attention. He was a cute young man that clearly did not bow to convention. Almost every head shot I saw on such folders looked like the person had just come from a stylist. Liam's picture looked more like he had just crawled out of bed. It was a good look on him. His stats, 5'9" 155 pounds told me he very likely had a compact sexy body. Though I generally gravitated toward taller men, the contrast of my 6'1", 195 pound frame with a smaller body seemed an interestingly erotic sight. Liam was 25 and single which made him a possibility for extracurricular activities. But his academic record showed him to be a hard worker and high achiever. Those types seldom needed extra tutoring or favors they imagined fucking me would bring.
Ronda Germaine at 35 was the oldest of the batch. She had been recruited from our competition. She was already an accomplished manager but had requested to attend the first available retreat after her hire. She had been with our company for seven months and her record was exemplary. She clearly didn't need my help and even if she did there was an item on her résumé that indicate she wouldn't be using her body to curry favor with me. Under affiliations she listed her membership in two non-professional organizations: The National Center for Lesbian Rights and The National Gay and Lesbian Task Force. I have nothing against lesbians and have even slept with a couple who like to occasionally feel a live warm cock inside their pussy. But I couldn't imagine that a person so out that they put such affiliations on their resume would have anything to do with straight sex. The fact that she listed a life partner on her benefits sheet pretty much cemented that opinion.
The third man, Philip Castlemen, was 30 and married with two children. He was a computer programmer who aspired to move into management. His goal was to one day be in technology management. However, our company did not believe in having managers anywhere that did not know our core businesses. If Philip wanted to break into IT management he would have to first successfully manage outside of the technology area. His head shot showed him to be a pleasant enough looking guy; just an average Joe. In fact almost everything in his folder indicated he was pretty much an average guy. Though I knew average guys who were married and by all appearances were totally straight sometimes sucked cock on the side, there was nothing to suggest Philip's possibilities in the folder. Of course even if he had never had his lips on a dick before, he had put forth a lot of effort to get into training program so he might well be willing to go the extra mile.
The final folder was marked Kim Turner. She was 27 and single. However, the freckled face that looked out from a head full of red curls looked much younger. The little bit of cleavage I could see in the picture indicated she had the ample breasts of a mature woman. Add to the picture her 5'2" hundred and fifteen pound frame and I could see she was likely a little bit of dynamite. Nothing I enjoy more than a little redheaded spitfire bouncing up and down on my rigid pole. However as I was approaching my forty-fifth birthday I had become increasingly aware of how it looked for an older man to be screwing young women especially ones who looked as young as Kim. Besides a cutie like her likely had a stable of hot young studs standing in line to fuck her. Still as I contemplated those big tits and red curls bouncing around as she rode my cock I couldn't help but reach down to my crotch and rub my growing bulge through my slacks.
My review of the new crop of trainees complete I had decided the chance of extra curricular activities was slim at best. I was also horny as shit from my fantasy musings about fucking each of them. I decided to call an old friend of mine, Tom Hastings. I had known Tom for twenty years. I had known his wife for fifteen of those years. Before he got married Tom and I were friends and occasional fuck buddies. The sex continued right up to his wedding day. Even though he had been open with Cheryl about his past gay encounters and she was accepting of his being bisexual, he had decided to go the straight and faithful route. A few months after their honeymoon Cheryl admitted the idea of Tom sucking cock turned her on. Their experimentation started by him talking about sucking cock while she sucked him. It moved to him sucking a dildo while she watched. Neither had the nerve to suggest what they both increasingly wanted; bringing another man into their bed.
Though all this time Tom and I had remained friends and I became more acquainted with Cheryl. For whatever reason Tom had never told her that I was one of the guys he had had sex with in the past. About a year and a half after the wedding Tom was at my apartment. He told me all about their sex play. He added that all the fantasy had made him crave a real cock. We took care of the craving in my bedroom. He sucked me for hours coaxing three loads from cock. I had never seen a guy happier to eat cum. A few weeks later I got a call from Tom. He wanted to meet me because he had a favor to ask. I figured he just wanted to suck my dick dry again and invited him to my place.
As it turned out Cheryl and he had made the decision to bring another man into their bedroom. Their idea was for her to watch as Tom sucked and got sucked and maybe fucked. The other guy wouldn't get involved with Cheryl except to watch her masturbate or get eaten by Tom. He had already told Cheryl that I was bi and a former sex partner of his. I thought the whole idea sounded fun. I liked being watched, Joe was a great cocksucker and had a nice cock that I enjoyed sucking. In addition, though we had only down anal twice he was a pretty good fuck for a guy. I have never been a big fan of anal intercourse at least not when there is pussy to be had. But if Cheryl wanted to see her man take a cock in the ass I was happy to accommodate. There was one other incentive. Cheryl has huge tits and I had wanted to see them bared since I had met her.
Cheryl is about 5'5" and easily fifty pounds heavier than what the charts recommend. While she is not what anyone would call a BBW she definitely has more than the required padding. Even though she had small love handles most of her extra weight found its way to her tits, hips and ass. She was a curvy, chubby bundle of sexual energy I soon learned. The first time I arrived at their house for a date I was greeted by Tom who was wearing only a robe. After showing me in and fixing me a drink he called Cheryl to join us. She was wearing an extremely sheer sexy nightie that was not made for sleeping. It was made of a translucent plum colored material that left almost nothing to the imagination. Her large tits filled the top perfectly and the material showed off her nipples and big, dark, round areolas. It was clear that she kept her pubic hair neatly trimmed. I could see the dark circle above her cunt that constituted all the hair she had below the waist. Suddenly I wished our evening was going to include more than just seeing her body.
