[MF] Meeting an older woman in the hotel bar on a work trip

Lately, I’ve been trying to rank my sexual experiences in my head, and think this is probably the hottest one on my list – probably because it was something I had kind of always fantasized about.

I travel a lot for work (events, conferences, training sessions, etc.) and went to a conference one fall in Pittsburgh. It was at a nice, full-service hotel downtown. One of my favorite things to do while traveling is enjoy some cocktails at the hotel bar and/or wander around the neighborhood looking for a great local place to relax. On this particular night, I chose to do the hotel bar, and I’m glad I did.

It was relatively quiet and Monday Night Football was on at the bar, so I sat down and had my usual – an Old Fashioned. I was just chilling out, nursing my drink and alternating between watching the game and scrolling through my phone. That’s when a nice looking, older woman came in and sat next to me. I kind of just glanced in her general direction and smiled, not wanting to seem rude and ignore her, but also not wanting to make her uncomfortable with too much attention.

She ordered a glass of red wine and started scrolling through her phone as well. I thought she was really attractive and I have always had a thing for older, business-type women. She was in a skirt, boots and a white button down top. I also noticed a ring on her finger.

We were kind of just sitting there, minding our own business until I made a comment about the game to the bartender, who was sort of lingering and watching. Something about the Cowboys history of underachieving, I think. Well, that got a reaction from the woman next to me, who was clearly well-versed in football because she had some opinions of her own. That was the spark that ignited our conversation. We talked quite a bit about football to start. She was in town for an insurance seminar, away from home for three days. Her name was Caroline. And I tell you, the conversation was awesome – natural, easy, interesting, funny. There was definitely some chemistry going on and we were becoming very flirtatious after a while.

We continued to drink at the bar until the game was over, then we ordered another drink and moved to a couch in the corner area of the bar. We continued to flirt and there was some touching, like her hand on my thigh, or mine on her knee, etc… nothing too crazy. It was clear to both of us where this was headed, and I was becoming horny as fuck.

As we finished our drinks, I told her I was having a really good time and asked her if she wanted another drink. I’ll never forget her response as it is permanently embossed on my brain. “No”, she said. “Let’s go upstairs and have sex”.

Caroline was 52, married, and had a cute, tight little body. She was in really great shape. Once we got in the elevator, we started making out and feeling each other up. We went to her room and once we were inside, we continued to make out until she unzipped my pants, pulled out my cock and eagerly began giving me a spectacular blowjob. It was amazing. Wet, kind of sloppy and lots of eye contact. After bit, I could feel myself getting close, so I stood her up, kissed her some more and started to undress her. First her top, revealing a cute, white lacy bra, then her skirt to find a sexy black thong. Then I took off her bra to expose a sexy pair of tiny tits with beautiful brown eraser-like nipples. I kissed her some more and passionately fondled, kissed, licked and sucked on her breasts before sliding her panties to the side to find a soaking wet pussy. I laid her on the bed, pulled off her panties, spread her legs apart and began eating her out. She made the sexiest sounds while enjoying my lips and tongue on her nicely trimmed pussy.

Eating a woman out is one of my favorite things to do. I flipped her over and ate her out some more from behind until she asked me to fuck her. I asked her if I should wear a condom and she said no, there is nothing to worry about. So, OK then. I slid into her for the first time missionary and we ended up fucking so good that night. Several positions – missionary, doggystyle, her on top riding me, from behind standing up against the window, her sitting on the desk with me standing and then doggystyle again, which is how I came inside of her. Afterwards, we showered together and made out some more.

I ended up spending the night and we fucked again in the morning, rather quickly, before she had to go to her conference and me mine. We made plans for dinner that night, which led to even more sex. Overall, we fucked four times in two days before going our separate ways home.

Source: reddit.com/r/gonewildstories/comments/1149d2o/mf_meeting_an_older_woman_in_the_hotel_bar_on_a