Colleen Ch. 01

(This is the first of several chapters describing a fantasy of mine. The fundamentals are true, the names are changed, but the trip never took place. Enjoy!)

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I had been mentoring Colleen professionally for approximately eighteen months when we got sent on a business trip together to Europe for several days. She had already traveled a couple of times on business, for which I taught her all the normal tricks of dealing with travel and travel accounting. So, I anticipated very little mentoring to be done in regards to travel, although I would be coaching her on her presentation techniques with a foreign audience. Boy was I wrong!

First a little about Colleen. She was in her late 30's and was most definitely the girl next door type. Cute, but not drop dead gorgeous. Curvy in all the right places, and maybe ten pounds heavier than she desired. Her clothes were always the size to fit her desired figure, not her real figure. Which meant that the clothes were just a bit tight without being inappropriate for the office. Her face was round with subtle cheek bone lines, and accented by a small mole just above the left end of her well defined mouth. Her eyes were a charcoal grey that blazed with excitement when she laughed, which fortunately she did quite often. She always had her hair tightly gathered on her head. For me, she was delightful eye candy every time we had the opportunity to interact. Which we did often as I mentored her.

In fact our mentoring experience had made us a bit of celebrities in our company as the company did a training film on mentoring using us as examples of a how to do it well. We enjoyed working together on a set for a week as they shot the series, and boy did I enjoy watching her as she was treated like a bit of a star, which, small town girl that she was, she just ate up.

Oh, yeah me. I am in my late fifties with over 30 years with the company, and am well recognized within my industry as tops in my field. Having been widowed several years earlier, I had poured myself into my job. And hobby. I worked hard at the company, wrote porn on the side, and had no social life other than the occasional sensual massage now and then. I worked out regularly and walked my dogs on our 2.5 mile trek every night that I was at home. I was in pretty good shape physically, if not socially.

Back to the mentoring. In all the time we had interacted, the only thing I knew about her personal life was that she was married with an 18 year old daughter. Sexy daughter, if the picture on Colleen's desk was close to truthful. All of our dialogues had been business focused, with only occasional small talk about anything personal. And, boy was that about to change.

Our trip included one night and one day in London, and then five nights and days in Amsterdam. We rode BA business class on the night flight to Heathrow, and for the most part didn't talk much as we were several rows apart. So, throughout the flight and our afternoon in London, our dialogue was perfectly normal, focused on business and travel logistics. After our afternoon meetings were finished, we agreed to meet for dinner.

By the time our entrees had arrived, we had finished the discussions that were necessary following our business day. To keep the conversation flowing, I casually asked about how her family dealt with her travel. And that was certainly the wrong button to push. Or the right one, depending on perspective. As soon as I asked about her family, she burst into tears. One moment she was bubbly and vivacious and engaged in dialogue; the next moment she seemed to be in utter despair. I reacted and attempted to recover.

"Oh my god, what's wrong? Did I say something?"

She regained a bit of her composure and looked at me. "I'm so sorry; I didn't want to break down like that. It is so unprofessional."

"Forget professional, Colleen," I responded, calmly. "Just tell me what's wrong." She just looked me in the eye, but her face had pain all over it. "That is, if you feel like sharing."

Tears continued to well up in her eyes, but she had pretty much regained her composure. She took a deep breath and then started, "It's either a very short story or a very long one."

"We have a long trip ahead of us. I'm listening. Take your time."

After another deep breath, she continued, "Well, I'm going to tell you the short version first, and then let you decide whether or not you want to hear the long version." I nodded in agreement, and continued to eat my entrée.

"Paul, that's my husband, left me over a year ago for another lover. And not a woman. He moved in with his boyfriend of several years, telling me he was coming out of the closet. Our divorce was final 72 days ago. Then, last week, the guy I had been dating for the past few months ditched me, telling me he was going back to the wife I didn't even know he had. And this happened just a week after I found out that Sarah, my daughter, has been enjoying sex for a couple of years and I had still thought she was a virgin." The tears restarted.

"Wow! That makes for an ugly couple of weeks. I'm ready to listen to whatever part of the long version you want to share. Why would you think I wouldn't want to listen?"

"Well you're my mentor, not my counselor or psychiatrist. And I was trained never to bring home problems into the office."

I understood her last point, having met her father when he was a VP. Talk about Mr. No Personality at the office with no apparent personal life.

I tried to comfort her. "Well, I'd like to think I'm your friend. And, we're not in the office. We are three thousand miles from home in a nice restaurant with some good wine. It looks to me like you might need a friend right now, and I'm the best thing you got. I'm as good as it gets."

The tears started again, but this time she had a small smile on her face. "Thanks, that means so much to me. I trust you more than you'll ever know. And I'd love to consider you my friend. But I am so humiliated, and embarrassed. I thought I could handle it all, and obviously I've failed."

"Hey, given what has been hurled at you, I'd say you're handling it really quite well. I had absolutely no clue how much turmoil you have been dealing with in your private life. Just let me know what I can do to help. In the meantime, I'll try to be good listener whenever you want one."

She spent the next hour telling me the story of her adult life, ever since she became pregnant in her senior year of high school. She worked and mothered while Sarah's father went to school and got a job. Everything went smoothly. After Paul got a good job and Sarah was in school, Colleen got her college degree and got on with my company a few years earlier. They went to church every Sunday, had a nice house, and had started saving for Sarah's college and their retirement. Colleen had pretty much concluded that the problems started when she joined my organization and started making more money than Paul, who was in a dead end job.

I also learned that she had only had two lovers her entire life, Paul and the guy who had just left her, and that while she was angry with Sarah for having sex, she was angry with herself for not realizing it, and she admitted to being a bit jealous that Sarah had already had more lovers than her mother. She declared herself a failure, a middle-aged plain Jane mom with a dour future.

Trying to be supportive, I engaged in debate, telling her that she was not a failure, and was definitely no a plain Jane mom with no future. I told her she was beautiful, kind, caring, responsible, intelligent, and successful.

By the time she finished telling me most of the details, we had finished dessert and the wine. We caught a cab back to the hotel, and as we parted in the elevator lobby, she asked me for my personal email address. I gave it to her, of course, wondering why she felt that she needed it, as she had my company email in her blackberry.

I went for my usual evening walk, checked my email and headed to bed. The next day we met at the appointed time to cab to our Heathrow office. From that time on until we boarded our flight to Amsterdam at 4PM, we only talked business. We were once again in different rows, so the next chat opportunity was the cab ride into the Marriott at Leidseplein. As we finished checking in at the hotel, she told me to check my personal email before supper if I didn't normally do that. I nodded in acquiescence, wondering what she would have sent me. We arranged to meet for supper an hour later in the lobby. I expected to be a tour guide, as she had never been to Amsterdam before, and I intended to take her to one of my favorite little places just off of Leidseplein for supper.

I powered up my laptop as I unpacked, checked my company email, answering two that were time sensitive, and then pulled up my personal email account. I wasn't surprised to see that I had a message from her personal email, but I was surprised to see that it was a fairly large email, approaching 1MB. It turned out to be a short note that asked me to read the attached Word file, which would explain the other couple of attachments, which were labeled a, b, and c.

I opened the Word document and started reading.

Dear Henry,

You have been so kind to me. I really appreciate it, and there is no reason for you to even care about my personal life. Thank you so much! Now, I really have one huge favor to ask. And it's huge!

Will you be my tour guide, escort and protector as I explore Amsterdam?

There it is. But, why is that so huge, you might ask. Well, that's the tough/easy part. Tough for me to say, but easy to understand once I say it. Or write it, which is why I'm doing this by email.

I WANT TO EXPLORE ALL OF AMSTERDAM; NOT JUST THE MANY MUSEUMS, BUT THE DARK SIDE AS WELL; COFFEEHOUSES, SEX STORES, THE RED LIGHT DISTRICT, ALL OF IT!

So, will you be my tour guide? Now about the attachments.

Attachment a shows what I have discovered about the coffeehouses. I've never been stoned and I want to try it. I hope you won't turn me into Security for that.

Attachment b captures a couple of web pages from an online sex store that supposedly has shops here in Amsterdam. I want to go to the store.

And finally Attachment c is an article about the Red Light District. I want to walk through it, see it, and even go to a live sex show. If you'll take me.

Thank you,

Signed Colleen.

My mind reeled. Not because of what we would do, but at the thought of doing it with her. I always enjoyed my travels to Amsterdam; I was still a hippie at heart, and I had always been a voyeur. So walking the district and getting stoned was a regular part of my visits to Amsterdam. I reeled at the thought of doing it with Colleen; a gorgeous young lady that I had lusted after from time to time, but she was my mentoree and there wer company rules as well as ethical issues associated with her request. If I said yes, she would obviously see me in a state of lust that would be inappropriate for our reltaionship. And I was going to, but somehow I had to make sure that she knew what she was getting into. I emailed her back.

"Wow. Before I say yes, I need to ask if you are prepared to be with an older gentlemen who is not immune to the effects of grass and the red light district. I can promise you that I would definitely not be politically correct. And I will most likely make very lewd and lascivious comments during the time we were touring. Are you prepared to see that side of me?"

She was obviously awaiting my email, because within a minute or two I had a response.

"I hope to. To be honest, I've always wanted to come here and see it. I'm here now and unattached. So, I'm going to try to enjoy it. The way I figure it, 'What happens in Amsterdam stays in Amsterdam.' So yes, I am absolutely prepared."

I responded, "Ok, see you downstairs in about 10."

I got to the lobby first, but had only been waiting a couple of minutes when she walked off the elevator. I needed to do a double take to make sure that it was Colleen. She was wearing a pair of denims that had to be painted on and a tied dyed tee shirt that left no doubt that there was no bra underneath. Her nipples jutted out from her very firm breasts making their presence know to whomever glanced. She let her hair down and I realized for the first time that it fell well below her shoulders. The very light curl of her hair accented her still pretty face in a sexy way that made her look about 20 years old.

She walked up to me and seeing the smile on my face, she asked, "You like?"

"Oh, yeah," I muttered. "What's not to like? You're gorgeous and if I didn't know better I'd guess you to be about 21 years old. Now I know I'm going to end up being lewd and lascivious tonight. And probably over you. So, I'll apologize now for any inappropriate behavior you might see in me tonight."

She beamed. "No apologies needed. I am looking forward to being the young tart on your arm. For the next five nights I am forgetting about my problems at home and I am focusing all of my energy on catching up on some of the things from the seedier side of life. And to have you as my escort is more than I could hope for. I was worried I was going to have to do it by myself. And I've been telling myself to do this ever since I found those web sites about Amsterdam last Saturday."

As we walked the three blocks to the restaurant, my mind considered the possibilities while Colleen absorbed her first impressions of the city. Over dinner I told her of some of my many visits to Amsterdam, providing the slightly R-rated version of the stories. Anyone who has been to Amsterdam knows that there isn't an R-rated version; only the hard core triple xxx variety once you headed into the Red Light district. But I was sure that if she had explored the web sites at all, Colleen knew what was she was going to see and experience over the next few evenings.

And she proved it when she finally said, "Look Henry, quit treating me so tenderly. I may be inexperienced, but I am not naïve'. I have voraciously explored the internet on all aspects sexual, and I can't wait to get started with ridding myself of the inexperience label. I want hard core sex and drugs this week. I just want to be safe. So, Henry, please just let go and treat me like your young girl friend." She paused, pursing her lips in thought. "Except don't be possessive. Let me do whatever I want. Just be at my side and keep me safe. Okay. Oh, and one more thing. I can't wait to see you with a hard on. I'm already wet thinking about it."

After dinner we walked a couple of doors down to one of my favorite coffeehouse. She turned a delightful shade of red when I showed her the menu, explaining that all of the choices were different types of hashish or marijuana. She was completely beet red when I had her buy our smoke for the night. We found a place to sit next to a couple of barely 18 year old kids and I showed her how to roll a joint. The kids giggled as I had to show her how to toke and hold it without coughing.

She mastered it on her third toke, which she held for what seemed like forever. She let it out slowly, and although I knew it hadn't hit her yet, she was already well on her way to becoming royally stoned. We alternated tokes back and forth finishing the entire joint between us. If the stuff we got was as good as the typical stuff here, we would both feel it very soon. Supposedly, it was really good at generating visual effects. I fetched us a couple of beers, watching her from afar just to be sure she didn't have a panic attack. She had lounged back and relaxed with her arms behind her head. I presumed that she was bright enough to know that caused her breast to swell outward and beg for attention from all of the heterosexual guys and lesbian girls in the room. If the evening continued like this I knew I would have many images to masturbate to that night after the evening was over.

By the time I returned with the beers I could feel the effects of the joint and it was hitting me pretty hard. She opened her eyes dreamily when I spoke her name, clearly under the influence. She smiled and said, "I think I'm stoned."

"Yep, I think you are. How does it feel?"

"Sublime would be the first word I'd use. But at the same time I feel like all of my nerve endings are at the highest level of attention, feeling everything. It's intense, but I'm so laid back it doesn't stress me out. It's very nice."

I sat down next to her and laid back. "Oh, yeah," I muttered, in stoned agreement. I relaxed and allowed the onslaught of visuals that I hoped would arrive. I rolled another joint and lit it. I toked and passed it to Colleen. She took in another deep toke and then smilingly offered it to the teens next to us.

"Is this your first time getting stoned?" the girl asked, graciously accepting the proffered joint.

"Oh, yeah, and it's great."

"Just wait till you have sex while stoned," the girl shared. "It's so fucking awesome!"

Hearing that comment, I opened my eyes just in time to see Colleen smile, saying, "Oh, gawd, I bet. It must be. I can't wait." She looked at me and smiled. The four of us finished the joint and fell into the typical stoned trance enjoying the music and the ambience of the coffeehouse. After several minutes of quiet stoned bliss, I felt motion next to me and I looked over to see the teens necking. Heavily necking. From the jaw action I could see, their tongues were fully engaged with each other, and her hand was visible caressing his crotch. His hands were all over her breasts.

As much as I enjoyed the show, I knew they would get kicked out if they allowed this behavior to continue. The coffeehouses had pretty strict expectations on allowed behavior, and blatant sexuality was passé. Turns out it was their first time in a coffee house, having just arrived from the states. They had gotten stoned many times but this was the first for them in public. They quickly apologized, and I waved it off. We chatted for a few minutes, but they were both so hot they left to go back to their hotel room and screw. Colleen gave them her card telling them to call on her cell if they wanted. The girl sensually ran her tongue all around her pert little mouth, and then whispered just loud enough for us to hear, "Oh, I want." I was pretty sure she was going to get what she wanted tonight. And with that she turned and left.

When I turned to Colleen, she said, "That girl is smokin' hot. Isn't she?"

Wow. I hadn't even noticed. I tried to remember whether she was or not, but couldn't.

"To be honest, I didn't notice."

"What, you didn't notice? I know you're older than me, but I was hoping you weren't dead yet!"

"Oh, I'm not dead. To be bluntly honest, my eyes have been solely focused on you tonight, Sorry 'bout that."

She laughed and her eyes sparkled. "Come on now. I know you were watching them. But thanks for the compliment." She was still laid back in the chair, and even in the dim light of the coffeehouse I could see her tits pushing the tee shirt out. My eyes lingered longer than they should have. "And, believe it or not, I am enjoying your staring at my boobs. Enjoy it, and I'm pretty sure you'll see a lot more than that."

I figured the pot had gotten to her, as I was still struggling to rationalize tonight's behavior with the previous evening's emotional outpouring. "We'll just have to see where we go from here," I answered ambivalently.

We took another couple of tokes, guaranteeing that we would both be completely ripped when we went back to the hotel. I fetched us two more beers, and we drifted back into the pot-induced reverie. In my mind I had already fucked Colleen, but I wasn't completely sure that we would get that far in reality. I didn't want to screw up our relationship, and I really wasn't completely sure where her head was with all of the shit she'd been dealing with. We grooved on the music for another hour or so, when I suggested that we head back to the hotel and crash.