The Tale of Jessica Moonshadow

Ben was always known for being full of shit. He was a small man with small man syndrome. The only thing about him that was big as far as I could tell was his ego. He couldn't tell of a single event without embellishing it to the point of ridiculousness. He was always the hero of the story, the champion, the tough guy or the ultimate lover or whatever other banal bullshit he could come up with. He could be funny, he certainly had an active imagination but most of the time he was just annoying.

Everyone knew it was all bullshit and occasionally someone would call him out on it but most of the time we would just laugh along. I don't think he had a clue that we were laughing at him and not with him. Over the years that I worked with him, I found that he was a lot like a chihuahua. Small, annoying, loud, constantly yapping and of no real value to me. The thing that astonished me was that, not only did he have a girlfriend but she was very attractive and quite intelligent. I just didn't get it. He was rude to her and belittled her in front of those who he considered friends. I just assumed that it was his insecurities making him act this way in public and that at home he was quite different. Otherwise, what the hell did she see in him?

I was married at the time, although not very happily. I was always faithful as I was raised in a very conservative family but that didn't stop me from fantasising about Ben's girlfriend Jennifer. If even a quarter of what he said about her was true then I was very turned on thinking about it. My wife was raised in a very conservative family too with the addition of strong Christian beliefs as well. This often led to tension between us, especially in the sex department. I had desires and wanted to try new things, I wanted to explore our sexuality, she most definitely did not. It wasn't that she didn't enjoy sex but as soon as I wandered off the straight and narrow path of "very vanilla" she would put a stop to it.

The weird thing is that although she enjoyed she seemed afraid of enjoying it and just letting go. Like enjoying sex was a sin and if it was for any purpose other than procreation then it was wrong and nasty. It eventually led to a complete lack of sex once our kids were born and that led to real animosity between us. Eventually, it reached a point where we couldn't go on together and we went our separate ways.

The next few years were a whirlwind of exploration for me. I met women and had several affairs but always seemed to come across the same old situation. I would say I wanted to explore and try new things and they were all keen until it came down to it and then they were all boundaries. I do understand that we all need boundaries but I had no idea at the time what mine were. Sure they were all more adventurous than my ex-wife but not by as much as I had hoped. Some were into oral sex, but only ever in one direction, as in I could go down on them but they wouldn't go down on me. Or vice versa. Most wouldn't even let you touch their asshole let alone slip a finger or anything else in and they definitely weren't up for doing any of those things to me. They never gave a blowjob without the expectation of something in return. I had read about women who enjoyed doing that just for fun but never met one. Not one of them was interested in exhibitionism or voyeurism of any kind and they never wanted to do anything outside.

I was beginning to think I was the freak that my ex-wife claimed I was and that what I wanted in a partner just didn't exist and that I would never meet the right woman. Was I chasing a unicorn? Don't get me wrong, sex wasn't the only thing I was looking for in a relationship; I wanted a fair, intelligent, equal and genuine relationship. Was it too much to ask that this fair, intelligent woman was also a little kinky?

Ultimately it all led to me going through the longest dry spell of my life since puberty hit, not to mention a deep depression that lasted for years.

By this time I was no longer working in the same place and I had heard that Ben and Jennifer were no longer together. It's not like I thought about her all the time, far from it, but when I did think of her it was always with a smile and the thought.

"I wonder what she's doing now?"

I assumed she was married to someone nicer and probably had her own little family now. Somehow, the thought of that made me feel both happy and sad. As though I had missed an opportunity that was never really there.

Conferences can be dull at the best of times and this one would be no different. It was one of those events, where the only people excited about being there were the organizers. Everyone else either felt obliged to support their workmates or was there purely because their employer sent them. For me, it was the latter, to the point where my boss straight up said.

"I would rather have my eye gouged out with a blunt stick than go to this bullshit, but they are really pushing for a representative to go. Therefore I am sending a representative...you."

I groaned in obvious displeasure which gained me nothing more than a chuckle from my boss. He knew exactly how much of a waste of time this would be. As the conference was being put on by a company that supplies us with paint, I would quite literally be watching paint dry.

I sighed as I resigned myself to the inevitable and accepted that I would be going no matter what.

"So where is it going to be?"

Living in a regional centre with several large towns around us I assumed it would be local. Maybe it would finish early and I could do something for myself for the rest of the day, I thought as a glimmer of hope emerged. One advantage of being divorced was that I didn't have to answer to anyone. Changes in plans weren't that big of a deal anymore.

"It's in Melbourne, I've got the details in an e-mail. I'll send them through to you."

Fuck! That meant a couple of hours driving there and then again to get home. I was not looking forward to this at all. Two hours driving in traffic followed by hours of boring presentation, followed by several hours drive home. I was either going to fall asleep at the wheel and die or I was going to be completely stuffed. I went back to my work with murder in my heart and I realised later that I had forgotten to ask when it was. I was thinking about asking for the day after the conference off because I knew I was going to be buggered from such a long day. Not long after that, the boss disappeared for the day and I didn't get to ask him for more details. I was fuming all afternoon until I could sit down at my computer for a while. I opened my e-mails and found the details my boss said he would send.

The first thing I noticed was that he had picked up on my displeasure. The rest I had to read a couple of times to be certain the details were correct.

"Just so you know, it's not as bad as it seems. The company sent the ticket through, which is on an attachment, and because we are more than 200km away from the conference they also sent a certificate for a motel at their expense for the night. Seeing as it is a Friday night and you are doing me a favour I decided to add another night for you so you can make a weekend of it."

This certainly lightened my mood. So instead of having to drive home after the event I could stay in the city and enjoy myself. I had no idea what it was I was going to do but suddenly it seemed to be full of possibilities. Would I go to a bar and perhaps watch a band or go to a flash restaurant or would I do the thing that I had always been curious about but never had the guts, or the freedom, to do. Would I go to a strip club? Because of my past relationship I had always felt a certain nervousness at doing things like that. I knew it was something that occurred quite often with a lot of guys but I had never had the gumption so I was nervous about it.

Thursday night rolled around and I found myself getting a little nervously excited about the weekend. I made sure I had everything I would need for a weekend in a bag and packed in the car by Thursday night. I had my dinner and tried to concentrate on a movie but it was boring and I knew I had an early start so I hit the bed early.

The alarm went off extra early and I felt somewhat proud of my restraint at avoiding throwing it across the room. I crawled, bleary-eyed out of bed and immediately put the kettle on. Today was going to require a LOT of coffee. Within the hour I was dressed, caffeinated, clean and ready to go. I made sure my bag was in the car and headed off. It was a beautiful clear morning as the sun rose behind me but it was not that easy to enjoy it knowing that I would be stuck inside listening to people talk about paint all day. I still hadn't decided what to do with the extra time I had in the city either.

It was like a monotonous daydream as I crawled through the early morning traffic trying to get into the city. I was almost at the point of worrying that I wouldn't make it in time when the traffic thinned and began to flow properly. I had just enough time to check in to the motel after parking my car and walked over to the convention centre. They had just opened the doors and people were milling about getting coffee and name badges as they registered. The company knew that they would need to keep the people caffeinated. That, although appreciated, did not bode well for an interesting day. I looked longingly at the beautiful day outside and caught a glimpse of a tall, curvaceous woman walking away from me. She was wearing a woollen skirt just above the knee and had very sexy curves. I watched as her ass swayed in that skirt while she strutted away. It was almost like she knew I was watching and put an extra dose of attitude in the walk. I wanted nothing more than to follow her and just watch that sweet ass sway for the rest of the morning. It certainly seemed far more entertaining than what I was about to do.

Everyone began flowing into the room like flotsam on a human tide. I held back hoping to get another glimpse of the woman in the skirt but it wasn't to be. I finally made my way in and sat in the back row against the wall. If I was lucky the place wouldn't fill and I might be able to catch a snooze against the wall if things got too boring. Everyone settled down and there was a murmur humming through the room as people chatted quietly with the others they knew there. Most people had come in groups of two or three and were no doubt discussing the fact that they would rather be at work than sitting here. There was a noise from the front and everyone looked up to the stage.

The talks began with the director of the company giving a run-down of what they were all about then introducing several key members that would be talking later in the day. Bloody hell, It was only twenty past nine and I was already zoning out and yawning. No amount of coffee was going to get me through this. I tried again to focus on what was being said.

"...and Jeff Knowles will be up after lunch to talk about the financial benefits of our primary range. Finally, we will be winding up around four o'clock. So first off the rank is Miss Jennifer Moonshadow to talk about our new ranges coming out in spring."

I swear my jaw hit the floor. There surely couldn't be more than one Jennifer Moonshadow in Australia. When she walked out on the stage I was given a double surprise. First, it was the Jennifer I knew, and second, that skirt was, indeed, the one I had been watching strut across the foyer earlier. Wow! She looked stunning albeit a little nervous. She had dark-rimmed glasses on and a business shirt that, while very professional, gave her an air of "sexy librarian". She certainly had the attention of the men in the room and I dare say some of the women. She was now talking but all I could focus on was how gorgeous she looked. My mind was playing back all the memories I had of her at work events back in the day. She had always been a woman that I found attractive but she always covered up a lot. Jeans and a thick woollen, over-sized jumper were her standard fair. This skirt did a great job of emphasizing her ass and legs while the shirt was very well-fitting and emphasized the curve of her waist and her breasts.

I was mesmerised as she spoke animatedly about products that I had no hope of remembering. I hoped they would have pamphlets later so I could have a read through them before I went back to work because nothing was staying in my head right now. She seemed to be scanning the crowd as she spoke and when her eyes met mine I swear she smiled in recognition. I was suddenly very glad I had come and I was already hoping I could catch up with Jennifer. Would she even want to talk to me? She did smile at me after all, but she may have just been being polite and I may just be a reminder of her relationship with Ben. Jennifer was now standing with her back to the audience while she used a laser pointer to show the different details on a projected display. Every time she moved, her ass jiggled most delightfully. My mind had wandered to the things I would love to do to that ass and I felt my cock harden in my pants, which I couldn't resist giving a bit of a squeeze. I glanced around quickly to make sure that no one else had noticed and was grateful for my decision to sit in the back corner. I watched her ass for a good ten minutes while slowly, rhythmically, squeezing my cock.

Jennifer turned back and looked me straight in the eye. It was like she could see my every thought and knew exactly what I was doing. I could feel myself blushing then she smiled a very seductive smile at me. The whole interaction lasted probably less than five seconds and I doubt anyone else noticed much more than her smile in the direction of the back of the room but it was very intense for me.

I doubt I could recall a single word that was spoken by her for the entire speech but the image of her was burned into my mind. People started to applaud and she smiled broadly at the crowd as she left the stage. It seemed cold and lonely now that she had gone and I was disappointed to see her go. The man who came up next reminded me of a sleazy used car salesman and given that he was talking about the drying properties of paint he almost couldn't have been more boring. Quite a step down in my opinion and judging by the way the audience was shuffling and quietly talking they thought so too. I spent the next hour daydreaming and trying not to yawn too obviously. When I felt my phone vibrate in my pocket I was grateful for the distraction. I opened it up and there was a message from an unidentified number.

"Hi... I thought it was you I saw in the crowd. I got your number from the registrations, I hope you don't mind. Would you like to meet me for lunch? We can catch up on life."

Now that was an opportunity I didn't want to pass up.

"I have to admit I was excited when I saw it was you. I would love to catch up for lunch. Can we go now? The only thing more boring than watching paint dry is listening to this guy talk about it. Lol."

"Hmm You did seem a little excited at one point there ;-) Better not, the boss will get cranky if I disappear too soon. I'll meet you at the door when you are all let out."

Holy crap. Had I said too much? Had I been too flirty, too desperate? Shit, could she tell I had been squeezing my cock while thinking about her? A million thoughts ran through my head but only one thing mattered. She had contacted me and she wanted to catch up with me. Any excuse would do me at this point.

I spent the next twenty minutes watching the clock, willing the minutes away. I know I sound pretty desperate, but you have to realize, it had now been over a year since I had been on a date of any description. My love life pretty much consisted of my right hand, some lube, internet porn and shame. Right about now, I was almost ready to explode at the thought of any female attention, let alone someone that I had admired for years.

I had to calm myself down. I gave myself a stern talking too.

"Christ, talk about getting ahead of yourself. Get a grip and stop being stupid about this. She has only said that she wants to catch up, nothing more."

The rest of the morning dragged on interminably. It was like dying a death of a thousand paper cuts. Eventually, they freed us and I had to wait for those that had stampeded for the door to go first. I finally made my way through the door to where Jennifer was waiting for me with a big smile. As I reached her she wrapped her arms around me in a big hug. Something I was not really prepared for, and when she let go of me she laughed at my shocked reaction.

"Oops sorry about that, I sometimes forget where I am. I know this sounds a bit weird but I am just really happy to see you."

"You know what? I have to admit that you have made the day worthwhile for me. I'm very happy to see you too."

She blushed a little but didn't stop smiling for a second. She reached out her hand and it seemed the most natural thing to do to take it and let her lead the way. She squeezed my hand and looked down at it as though realising that this wasn't a normal interaction between two people who haven't seen each other in a long time. She smiled at me once more and nodded towards our hands.

"So we don't get lost or separated in the crowd. Follow me."

Jennifer led the way out of the crowd and towards the large double doors that had been propped open. She led me outside into a beautiful sunny day. We made our way across the street and into a strip of shops that were all spaced along one side of a walkway. They all sold food or drink of one description or other. On the other side of the walkway was a park with a few trees and benches for people to sit around.

The crowd thinned considerably as we walked along the path but neither let the other's hand go. I felt a little giddy with excitement and I couldn't stop checking out her ass whenever I was sure she couldn't tell. She stopped walking and turned to me.

"So what do you want to eat?"

I'm pretty sure my inner thoughts must have been written across my forehead because she laughed.

"Not on the menu mister, for lunch anyway. I'm going to have a roast roll, do you want one?"

I was still in shock about what she had said about the menu. All I could do was nod in agreement and reached for my wallet. Jennifer laughed although I don't know whether it was because of the look on my face or the fact that I had reached for my wallet. She waved a plastic card in the air.

"Don't be silly, company card."

"Oh, okay. Should I find us a seat then?"

"That would be good."

I wandered off in search of a suitable table and when I looked back at one point I noticed she was watching me walk off and admiring my ass. I smiled to myself as I thought this was going better than I could have hoped. I sat down and watched her as she ordered and waited for the food. She seems so different, I thought, as I remembered the girl she had been. She was always nice to me but never flirty like this and she always wore those oversized jumpers as though trying to hide that shapely body.

She picked up the orders and walked back towards me and she had such a sultry smile and a swagger in her walk that by the time she got to the table I was hard as a rock. I loved the way her nipples were pushing at the material of her bra and making points in her shirt. My cock was so hard it hurt in my pants and I wanted to adjust but I didn't want to make a scene in front of Jennifer. She was still smiling that sultry, I know something you don't know smile, as she sat down and handed me my lunch.

"Thanks very much for this."

"You're most welcome."

She looked at me with an inquisitive smile.

"Is everything okay?"

"Ah yeah, it's good, just a little uncomfortable."

I couldn't believe I was putting it out there so casually. It was like she had me under some kind of spell. I figured though that it's out there now and gave myself a quick tug in the right direction and was very relieved to have found more room in my pants. I was trying to be very casual but I am sure that my face was glowing. Jennifer was laughing and smiling even more at my obvious awkwardness.