Teasing | Working It For a Stranger

I had every intention of getting this posted yesterday for you guys but Blogger for some reason wasn’t playing along. It might have something to do with half of the city being without power after some pretty nasty weather. One guy even described the hail as being as big as Timbits …only in Canada, eh!

Crazy weather…which is a suitable analogy for my crazy lifestyle these days. Well, a tornado might be a better comparison than Timbit hail.

This was something that a guy asked me a while back and I’ve been putting some thought to it along the way. He was asking me to share an experience where I intentionally teased a complete stranger, and things like my website and Twitter did not count.

So for me, I was thinking that I wouldn’t get too much into this summer’s silliness with flirting contests and such, but rather visit one of those memories that I think was a turning point for me on this sexual adventure.

You’ve already read about the moments where my bisexual curiosities came bubbling to the surface, and that small moment of regret I have where I could have taken a bit more control, but drunkenly let the moment slip. Well, this is from the same conference, the previous year. And it’s funny because I’m starting to wonder how we ever managed to take in any of the education from the sessions each year.

I had bought this great brown suede skirt and stiletto boots to wear. On the first night of the conference - before the crazy really set in - my co-worker and I made our way down to the keynote dinner. It was a somewhat dull affair - as can be the case at these events - so after everything had wrapped up, we were in need of a drink. Instead of hanging out with a bunch of frumpy women in sensible shoes discussing the scientific aspect of the speaker’s presentation, we headed off to the hotel bar with the idea of loosening things up.

The great thing about where this conference is held each year is that it is in a hotel attached to an international airport - and that means lots of hot guys passing through for business.

So there we were in the lounge, thinking we were hot stuff, and basically just washing away some of the day’s work and stresses from back home. So much like the stereotype stories, a little bit into the evening a couple of drinks show up for us from a few guys sitting in lounge. Now, at this point in my life my level of flirtatious bravery was pretty minimal as I was just really beginning to discover myself and my desires, but my co-worker has one of those great attitudes about life and it wasn’t a minute later that I am following her to where the guys were sitting.

The conversation was pretty typically for a bit - what we were doing there, what they were doing there, etc. - and as the night continued on a couple of the guys went to their rooms, leaving just these other two guys, my friend and I to carry on. I guess those boys figured there was no chance of bedding a couple of pharma science geeks - especially with the gold bands we were sporting on our left hands.

But for the four of us left behind in the comfy chairs, none of us was feeling any pain and a lot of the inhibitions had softened. One guy and I were getting into quite the conversation. Like me, he was married, so in a way I felt no threat or ulterior motives and the drinks were making it easy to be a lot more open.

At one point he commented on my boots - a flirtatious move, for sure. I hadn’t really been paying too much attention to myself, but as I looked down to my legs after his compliment I realized that my already short skirt was riding pretty high. In fact, given the chairs we were sitting in, I had no doubt that the guys would had been sitting across from me had been getting an awesome look at my panties when my legs weren't crossed.

I would have thought my friend would have said something, but she was really into her own conversation with the other guy…and as I learned the next year, she was also probably enjoying the view herself.

So, what’s a girl with more than a couple Caesars in her system to do? Some would pull the hem down, but no, not Andee at this point. I did one of those stretch-one-leg-straight-out moves so this guy could get a really good look at my boots - and an awful lot more leg than was originally intended at the start of the whole night.

And this all opened the door for the conversation to go in a more intriguing direction.

As we got more and more comfortable with each other, the innuendo got a bit more racy, until the point where we were openly discussing sexual preferences, experiences and fantasies. I found myself sharing some pretty intimate thoughts ranging from why my favourite sex position is that particular one to the craziest places I had done it. I think I may have dropped the idea of being picked up in a hotel bar by a complete stranger for a night of anonymous sex, but that may be just my shaky memory ...

Anyway, there comes a point where things shut down, so as we wrapping up our night in the lounge and those responsible little voices in the back of our heads say “time for bed married women,” my new friend said a polite goodnight and how nice it was meeting us, yada yada. I took the opportunity for what I thought at the time was a pretty bold move, took one of his hands in mine, leaned in and gave him a little peck on the cheek. In my hand I had passed him a piece of napkin on which I had written the address to my website.

“That’s just in case you want to see more of me,” I whispered before trying my best “I know you are watching my ass in this miniskirt” walk out the door towards the elevators.

I went and quietly masturbated in the bathroom ... He joined a couple days later …

Andee     xoxo