A Wor Fling

So my story is back in the day when I used to travel a lot for work, usually away from mon-fri somewhere. On this occasion (2001 I think) I was working in our main office so this often meant there were evening gatherings of those office based and the remote workers like me. This particular evening a group of us had gone out for a meal and then back to the hotel most of us were staying in for some drinks. This was the days of almost endless expenses, particularly as the boss was also there and he signed off all of them!! The girl in question was late 20's/early 30's, full figured, short black hair and lovely blue eyes, we had always got on but nothing untoward. The drink obviously was having an effect and we were flirting and finding excuses to make physical contact.

As the evening started to wind up, she asked for someone to walk her to her car (she lived locally), looking pointedly at me. Gentleman that I am, I of course offered but so did my boss. I still wonder if he realised what was happening so was trying to intervene. I was married with 2 kids although she was single with 1 kid. So we both saw her safely to her car, the evening ended and I went back to my room. Shortly after I got a text and it was from her, thanking me, I replied and then we had a bit of back & forth before she asked if she could call me. This was a pre-smart phone so no pics or video chat.

The chat got very flirty and she finally said that if I had walked her back on her own, she would have snogged me! Those actual words, remember them very clearly. The call then very quickly became phone sex and we both had a very happy ending. Next day was Friday so it was my last day in the office that week. We were in meetings together and she kept avoiding my eye so I figured it was a drunken one off event. Late in the day we found ourselves alone in a conference room and she mentioned how embarrassed she was but she had enjoyed it, I agreed so things were left open ended.

Whether it was the following week or later, I was down there again and since we had been chatting using the company Sametime, we arranged to go for a drink. She picked me up, having to be discreet since once again others were in the same hotel and went to a pub out of town a bit. We still managed to bump into someone from the same company but not our immediate team. Very pleasant evening was had and she drove me back to my hotel, parking at the back of the car park. We chatted a bit longer until she said "You decide what happens next?" so I leaned over and kissed her, very quickly moving onto french kissing and roaming hands.

We then decided to move into the back seat and I got her blouse open and her tits out. They were a good D/DD cup and lovely pert nipples which got nice & hard with my mouth on them. She quickly got my cock out too, which was not surprisingly very hard! She then told me to pull my trousers and boxers down before she went down on me and gave me a blow job to a conclusion. She swallowed too, she loved to please that girl. Things calmed down after I had cum, it was too risky to go to my room so we called it a night there. We would exchange messages during the work day, often dirty ones too but luckily it was not monitored.

Next time I was there again we arranged to meet for a drink and this time I picked her up. I recall we spent less time drinking and quickly drove somewhere quiet. Still too risky to go back to my hotel and she had her kid at home being babysat. Straight into the back seat and more clothes off this time. I certainly got inside her and was humping away but warned her when I was close to cumming. So I pulled out and she went down on me again, swallowing all my spunk. Third time was much the same but she was driving and was also on her period so straight to the blow job again. She always said she loved giving them, she also told me she would let me do anal with her but sadly never got to take her up on the offer.

After that it must have been towards the end of the financial year and they cut back on travel expenses so wasn't going to the office. Things kind of drifted from there, she met a guy (who she ended up marrying) but we still flirted on work chat. Last thing I can remember was chatting to each other online, in the office, and her telling me she had had a fling with another woman, teasing me with a few details which obviously got me aroused. I typed to her that I was going to the loo for a wank then walked past her desk, smiling at her before doing exactly that. She told me later, she was so aroused by that but was stuck on a call. Eventually she left the company, got married then divorced and married again. We are still friends on Instagram but no chat, seeing her pics I still would and do regret not getting a night in bed with her to really enjoy some fun.