Lightly Touching Gail

This happened when I was a hotel employee long ago.  One summer I got a job helping with larger, catered parties at a large hotel.  My job was to keep the bars stocked with all types of beverages, ice, napkins, and anything else that the bartenders might need.  On the really busy nights, I would set up any number of these bars at the beginning of the night and spend the entire night moving between the parties because most had open bars and the consumption levels were high.  On an occasional slower night, usually a Monday or Tuesday, I would have to set up a few, but after that if the parties were small, there was plenty of time in between tasks as I could check them all within about 15 minutes and even slightly overstock them with supplies so there was no way they would run out.  Many of the small ones had no servers, but some of the medium and larger ones had one or more cocktail waitresses. On the night in question, I had only three to handle.  One was larger, and the other two were quite small.  The larger one had a single waitress, Gail, who I had known for about a month.  She was about 28 or 30 I would guess, and she was a really nice woman.  She was also what today we would call a MILF—good looking in all the right places.  She was nicer than all the other waitresses, at least to me.  She was in an unusual situation in that her husband was away in Europe on some kind of assignment from June through September.  Previously, there had been a night when Gail was having a really hard time.  I had seen one of the many managers berate her in front of customers, and she was not in a very good mood in the first place.  I was in the room she was handling much of the night, and we talked a few times during the slow parts of the night.  I just tried to sympathize with her about the bosses, and reminded her that the problem was them, not her.  She cried a little, and I had at one point put my arms around her from the side, and she clearly appreciated the thought.  She even moved into me rather than away from me, so we ended up facing each other.  I was not trying to put any move on her, and she knew it.  One thing I had noticed after that tough night for her was that she acted differently toward me than the other waitresses.  The bigger rooms in this hotel were set up so the waitresses had a sort of private runway behind the bar.  No customers were allowed past the front of the bar; anyone who wanted to could just go to the front of the bar, where there were one or two lines if they didn’t want to wait for the waitresses.  There was usually a chair back there to sit on, and I frequently did after going around to the other bars.  The bartender can’t see you if you’re sitting in the chair because the chair is low and the bar is pretty high and the bartenders had to reach pretty far to pass the drinks to the waitress.  Anyway, when I sat back there, the other waitresses would naturally move away from their normal spot and away from me.  Gail, on the other hand, would often move right next to me.  When she did this, I was sometimes almost touching her when she was putting in drink orders or picking them up.  Obviously, I didn’t mind at all, and sometimes we would talk a little back there.  On this night, since I had little to do, I was in the chair quite a bit.  Since Gail didn’t seem to mind my being there, I was inching the chair closer to where she had her drink supplies.  I’m not sure how soon she noticed, but although I expected her to move away a bit, she did the opposite, and stood just an inch or two from me.  The outfits they wore were essentially red mini-dresses with black hose.  Gail had great legs and looked fantastic in her little “uniform”.  I was reading the newspaper and when she came back there to place an order, she reached across the bar to her right to get more straws or something, and she leaned right into me so her upper thigh was resting against my upper arm mainly.  I didn’t say anything and she didn’t either.  She went back with her drinks, and I was wondering what was going to happen next.  She had to make a few more trips and did so pretty quickly.  When she returned, I could hear her tell the bartender that she was “caught up” for now.  I thought she might ask to sit down, but instead she grabbed a section of the newspaper I was reading, and she put it on the bar and started reading.  She was again standing almost against me already.  I very lightly touched her right arm (which was hanging down) with my fingertips and was going to say something, but she sort of turned away, and as I ran my fingers part way up her arm (but not high enough where anyone could see), she sort of shivered a bit and moved even closer to me.  She could see most of the room from back there, but no one else in the room could see her below about chest level.  Now her right leg and hip were right against me, so I ran my hand extra lightly down her leg toward the floor.  She didn’t move, didn’t acknowledge me, and she especially didn’t move away.  I ran my hand gently back up her leg, along the outside, and I really enjoyed the feeling of the smooth hose and her shapely leg.  A minute or so later, she must have seen a customer waving for her, so she left to get them drinks.  After that, she again grabbed the paper and stood right next to me.  I put my hand against her right thigh, and she again didn’t flinch.  Then, I reached around and touched the outside of her left leg, again very softly.  After a minute, I started touching her right leg, the one close to me, all around it on her calf.  Still no reaction.  Thankfully, I was wearing newer, tight briefs that at least kept my hardening cock from going vertical.  I moved slowly up her leg, and soon had touched pretty much her entire leg up past mid-thigh.  I was now using both hands, and just in case I wasn’t clear on her feelings, she moved her right leg toward me, spreading her legs several inches more.  After touching her left leg in a similar way, I went back to the right leg and started inching up.  I picked up the newspaper again in case anyone appeared suddenly, but kept my right hand moving on her right leg.  I slowly moved up her inner thigh and just brushed against the beginning of her crotch when she flinched slightly but made no other move or sound.  After that, I moved it all around her vulva without touching the key points.  Then, I moved my fingers as gently as I could right between her legs and into the area of her slit.  I barely touched her, but moved slowly up her slit and back down a few times.  She seemed to be fidgeting a bit up above the bar, but if anything she moved closer to make it easier for me to reach.  I kept going for another couple of minutes, and then she finally stood up tall and grabbed her tray and walked away.  I had figured on this because soon it would have been obvious to others that she wasn’t just reading the paper.  She was gone for 5 or 10 minutes, and of course I was fantasizing about what she was doing while she was away.  The best part was that she never mentioned it to me, and it was understood between us that we would never get involved with each other.  Her smile was maybe a little warmer, but it was clear that she didn’t want anyone to guess that we were involved somehow.  The little secret was ours, and was repeated a few other times, mainly to just a limited degree because it’s usually too busy for this.  That night, as I came super hard thinking about her, I was hoping she was in her bed also coming very hard.