The Woman at the Hotel Bar [MF]

So I’m a 45 year old, recently divorced guy. Using my new singleness to be actively sexual again (on both sides of my bisexual interests), and it’s been a blast. This story is from just a few weeks ago.

I was on a business trip to Los Angeles for a week. I was able to stay at a somewhat “resort” kind of hotel near the beach, and I had a fair amount of free time that I spent chilling in my room, hanging by the pool, and walking the beach. For the most part I wasn’t really seeking out sex, I was just enjoying my alone time and big hotel room.

On maybe my third night there, I was eating dinner at the very empty hotel bar. I had had a martini and a glass of wine, feeling nice and buzzed, when a woman strolled in and took the seat right next to me, even though there were plenty of seats available. She glanced at me with a nice smile and said, “do you mind if I take this one?” I told her to go ahead. She was mid-30s, with a great pair of tits in a preppy, thigh-length summer dress that gave a nice view of a moderately plump ass. Overall she wasn’t a jaw-dropping stunner, but more than good looking enough. As for me, I’m tall and broad-shouldered, but a bit of a dad bod underneath that I’m constantly fighting. Sitting at the bar, though, I have to admit that my tanned and fairly hairy arms would have nicely filled out my polo shirt.

Like I said, I hadn’t really been looking for action, but I thought to myself, “well, I guess you gotta try to go for it now, bud!” What kind of man would I be if I didn’t give it a shot? So I decided I’d see if I could pull her, and wanted to try to make it happen that night.

At the bar, I didn’t feel like I had to try very hard to move things forward. Kate — as her name turned out to be — was a day early for a conference that started the next day. Also an out of towner, from another big city on the East coast, and as I guessed, about 10 years younger than me. We had a good, easy-flowing conversation, and before I knew it, our barstools had turned toward one another with our legs just starting to touch. We were both being flirty, and I had a good feeling about it.

So, I decided to be somewhat direct, and just asked her, “so what are your plans the rest of the night?” “No plans,” she said. So I said, “listen, my room’s big and has a nice couch, and I’ve got a bottle of bourbon that I won’t finish by the time I go home, do you want a nightcap up there?” She smirked and said, sort of passively, “okay, just a nightcap.”

There was sort of a weird vibe when we got to my room. Like she wasn’t being forward and flirty anymore. We sat on the couch and kept having a pleasant conversation, but I wasn’t any closer to being in her pants. I would have to work for it now. So I inched closer as we sipped our drinks, and deliberately turned the conversation toward fitness. I don’t know why, but sometimes I feel like talking about physical activity and our bodies helps move things along when you’re trying to get someone in bed. She told me about a half marathon, I told her about crossfit. I complimented her runners’ calves, and she touched my hand when I offered it to to show her my calluses from lifting and rowing.

At that moment, I leaned across and kissed her. Game on. She was into it, and we made out on the couch for a while, hands starting to explore each other’s backs and asses.

She was the one who suggested moving to the bed, so we plopped down there fully clothed and kept making out. My shirt came off, then hers. She told me to leave her bra on for now. We kept kissing, and my hands went up her legs. I tried to slip a hand inside her panties, but she grabbed it and said, “not yet.”

She then turned around so I was spooning her in the bed, and she pushed her ass into me hard, grinding my full-mast cock through my jeans as I kept kissing her neck. As my hands explored her tits, she let me unhook her bra, and I tried again to slip a hand into her panties. And again she said, “not yet.”

This was a little weird to me. She was clearly into it, we were both nearly naked, she was grinding all over my cock, but wouldn’t let me any further. She also didn’t make any moves to really touch my dick or give me a BJ, which most women in my experience would have done by that point.

I slipped my jeans off, now only in boxer briefs, and came at her again from a spoonign position. Now she could *really* feel my dick as I pulled her close, and she moaned, “oh that feels good, oh fuck” as she kept grinding. But every time my hands started to explore her upper thighs and get close to her mound, she waved me off. And she wasn’t being that verbal, either. Still, I was enjoying playing with her tits, kissing and grinding.

This went on for *hours.* I’d never experienced anything like this. She loved grinding, at one point turned over to straddle me and make out some more and let me suck her nipples, but she never went for my cock or let me get into her panties. I could even see that she was kind of wet at this point through her panties, but still nothing was happening.

Finally, at about 1:00 a.m., I summitted that mountain faster than I thought it would happen. Almost all of a sudden, she stripped off her panties, I followed suit, and for the first time she gently, almost primly or prudishly, grabbed my dick as I laid there and said, almost in an embarrassed whisper, “do you have a…condom?” I nodded, hopped off the bed and grabbed one out of my backpack a few feet away. She sprawled back on the bed with her legs wide as I put it on and added some lube. I kneeled forward between her legs, teased her pussy lips with my tip, and then she got aggressive, completely out of character given the last few hours, and pulled my ass so I pushed deep inside her all at once.

Almost immediately, she was moaning, and only really ever said one thing, “faster, faster.” She said it a lot — she liked it fast, I guess — as I pounded away. Her pussy felt fantastic. It was a shame she hadn’t let me explore it more. I love using my hands and really love eating women out, but this was feeling pretty great, too. Her bra was off by this point and I loved watching her tits bounce as I fucked her. Mainly because she kept saying, “faster,” I didn’t change positions or stop, and soon enough I was ready to cum. It was fine with me because I thought we would have the rest of the night for more. I grunted that I was going to come and she said, “yes, yes, oh my god” as I moaned out my orgasm, shooting into the condom while I was deep inside her.

She smiled and said that had felt great. She told me she had orgasmed too — she used that word, she didn’t say she “came,” which was a little odd to me — although I honestly hadn’t felt or noticed it. I was ready to cuddle and rest for a round 2, but she was up out of bed and getting dressed within a minute. She was super apologetic but said she had an early morning. We exchanged numbers with a vague promise to catch up the next day, but I didn’t see her around the hotel the next day.

I thought about texting her because I would have loved to take her in a few different positions and explore other stuff with her, but I didn’t bother because the experience had been so odd. It was a lot of fun, but just so weird that she made me wait for hours before suddenly insisting that I fuck her as fast as possible, and then jumping out of bed with the “early morning” excuse. Anyways, I still enjoyed myself and at least made enough of a mental image of her tits that it got me through a couple of jack sessions the next day. :-)

Source: reddit.com/r/gonewildstories/comments/d109n0/the_woman_at_the_hotel_bar_mf