[MF]. Hotel bar pick-up leads to a night of fun…

I travel a lot. There are bad things about it, but there are also great parts about it. Hotel bars usually play a large role in the great parts…

On this particular day I happened to be in Orlando Florida in the summer. Needless to say, the day had been hot. But if you know anything about Orlando at 6pm in the summer, there is a great chance it’s going to be raining. I’d left my room ready to go explore along Orange Ave and find somewhere for dinner, but when the elevator doors opened and I could see outside the hotel it looked like the heavens had opened up and rain was pouring down. Even for Orlando this was a lot of rain. Fuck.

Ok, so my choices were to wait out the rain or have dinner at the hotel bar. I looked to my left and noticed an attractive brunette woman around my age (I was 41 at the time) sitting at the bar. My choice was made.

I sat down a seat removed from her and asked the bartender for a menu. As I’d walked towards the woman I could see she was in good shape, and looked like she could have been Sandra Bullock’s sister. Very attractive to me, but she was staring at her phone and I took that as a “leave me alone” so I focussed my energy on what I was going to have to drink. Yes, the woman was appealing but the window wasn’t open enough for me to commit to dinner at the hotel yet. I mean, what if seconds after I order my crappy meal she picks up her drink and leaves, and the sun comes out, and I’m stuck alone in a hotel bar with a below average burger? No one wants that!

So my drink was ordered and we were both looking at our phones but she begins to chat with the bartender. I wasn’t really paying attention, but after sitting for about 10min there was something that was said between the two of them that I commented on, and all of a sudden I was a part of the conversation. This was 7 years ago, so forgive me for not remembering what the bar banter was about, but slowly the conversation started to become more me and her, and the bartender slowly started to come around less often. She was giving good signals by asking questions about me, leaning into me, and we ended up having a delightful conversation. She even admitted, “when I saw you sit down I worried I was going to annoy you.” I reassured her that was very much NOT the case.

At some point I asked her if she had plans tonight. She had said she was from Tampa, but decided to get a hotel downtown for the conference she was at, and enjoy the city, and so she had no plans as of yet. I made my suggestion…

“Lets meet in the hotel lobby at 11pm. We can walk up Orange Ave a little and we’ll have one drink at a few different spots. We’ll go where the wind takes us.” She smiled and replied “that sounds fun” and we began asking the bartender for advice on bars to visit. The ice was broken and the chemistry was light, but not yet overly flirty.

When 11pm came around, I walked down to the lobby and into the bar, and there she was standing with a group. This was my first time seeing her standing and lets just say it was very nice…

She was about 5’5, and in good shape but not obsessively so. She had dark brown hair and very dark eyes. But it was the dress that got my attention… She was wearing a dark green dress below her knee with a slit up the side. Her shoulders were bare except for the spaghetti straps, and there was tasteful b cup cleavage being shown. The material of the dress was very thin and it was clear she wasn’t wearing a bra, and a betting man would assume she was also without panties too. She looked great.

I approached her and she noticed and smiled. “You look sensational” I told her, and she replied “You as well” while looking me up and down.

“Shall we go?” I asked, eager to get her away from the group just in case there was someone else that had their eye on her. “Of course, lead the way”. I extended my hand and she naturally took it as we left the hotel and started to walk up the street.

Our first stop was uneventful. We sat, flirted some, laughed a lot, and generally had a nice time. Once our drinks were finished I told her I knew a cocktail bar a few door down and that would be stop number two. “Perfect” was her response and off we went.

We sat at the bar and made small talk with the bartender then turned to face each other in the bar stools. I started to touch her leg to punctuate a point and she would put her hand on my arm when laughing at a joke. But it was when she stood to go to the restroom that the ice was really broken. She jumped down from her stool so that she was standing between my legs and just leaned in to kiss me. Then pulled away quickly, smiled, and declared “be right back.”

When she returned the mood was different. It was now clear how the night was going to end but the question was how long we could resist the temptation. She sat and my hands were now fixed to her hips as we chatted. We’d fill pauses in the conversation with a soft, sensual kiss. It was really fun. We finished our drink and I told her I knew another bar across the street. We got up and left the bar but it took us several minutes to exit. We had a kiss at the top of the stairs, then only made it about halfway down before we were kissing with me standing one stair below her and my hands groping her ass. Then we finally exited but there was a brick wall that seemed to scream “pin her against me”, and so I did and we made out again.

Finally we made it across the street to a basement bar. It was crowded and loud, with a very fun atmosphere. She found a spot at the bar and we ordered with me standing close behind her. You know what happens in these situations… I lean forward to press as much of my body, and ESPECIALLY the fun parts against her body, as she sticks her ass back into me as if to either say “You are getting this later” or “let me see if I can feel what you were working with”. Regardless of the question, my answer was to grab her hips, and her response was to give a wiggle.

Our drinks arrived, we took a “cheers” and looked at each other as we took our first sip.

“Wanna just go back to your room?” I asked.

“Let’s go”, she replied.

We put our full drinks down on the bar and left.

The basement bar required us to make out on the way up the stairs. Somehow that brick wall that screamed to be made out again seemed to have multiplied, and there were now several walls in which I HAD to pin her against and we started to explore each others bodies more. I would cup her breasts, or run my hand up her legs, then we’d break the kiss and hurriedly walk towards the hotel before there would be another damn wall and now her hand would be rubbing my cock over my pants as we made out.

Now, by no means am I porn star in that department but I’m also very confident in what I have and that ladies are excited when they get their first sense of it. So when she ran her hand over my cock and muttered “oh fuck yeah”, all I could do was break the kiss and get her to the hotel ASAP.

We made out like high schoolers in the elevator and thankfully her room was close by. We were making out as she opened the door, and once open I was backing her towards the bed. I believe I had my shirt off and her dress up over her head and on the floor before or just as the door clicked closed. She was completely naked.

The teasing had gone on long enough. There was urgency between us now. When the back of her legs hit the bed, she lay back on the bed and I quickly moved into position kneeling between her legs. Normally I love to tease a woman by letting her feel my breath on her wet pussy, or kissing the insides of her thighs and building the anticipation. Not this time though. I made my tongue flat and licked her pussy from top to bottom as she moaned her approval. Then took my fingers and spread her lips, and began to explore. She appeared to be in heaven right from the start. She was certainly wet, and vocally appreciative of the attention she was getting. And she tasted incredible. I needed to make her cum.

After exploring her pussy with my tongue I sensed she needed more and quickly licked a finger before sliding it into her as my tongue and lips worked her clit. I quickly added the second finger and massaged her g-spot as I licked her clit. It didn’t take long for this to put her over the top and she grabbed her breasts as she looked down in to my eyes as her orgasm crested, then threw her head back and arched her back as it took her over. She filled the room with a grunting “Fuuuuuuuuuuck” and I felt the squeeze of her thighs around my head. I gently licked her until she squirmed from the sensitivity.

I’d been hard for the better part of an hour now, and most of the “nice guy” inside of me was gone and was replaced by the man that needed to be inside his woman. I stood, and we locked eyes with a smile as I unbuckled my pants, and lowered them to the floor, confirming her suspicions that I was not wearing underwear either.

Now, I know… this part was not smart. It shouldn’t happen this way. But goddamn was it hot too. We’d not discussed anything surrounding condoms. We were complete strangers. I should have reached for a condom and put it on, or started the conversation about testing (I was recently tested and have had a vasectomy, but I had no idea about her, and she had no idea about me). I should have paused.

But what I did instead was take my thick cock in hand, and swiftly thrust as deep up inside her wet pussy as I could. Curse words filled the room. “Fuck yea”, “oh shit”, “oh fuck”. We were both lost in the moment and couldn’t get enough of each other.

“Your pussy feels incredible” I told her. “Your cock is so hard inside me” she’d reply.

I pulled out, still standing on the floor, and she got on her knees and turned her back towards me. I ran a hand up her thigh, found her pussy, and pushed back inside her forcefully. I grabbed her shoulders and pulled her back into my thrust. This is where my downward curve apparently becomes magical, and she was no different. She dropped her elbows down to the bed and told me not to stop. I continued doing exactly what I was doing and within seconds she came on my cock.

I knew I was now close, but I flipped her back over and crawled onto the bed on top of her. She reached down and guided my cock into her pussy as I hooked my arms under her legs. I wanted to be as deep inside her. As I pushed inside her she whispered in my ear “are you going to come visit me next time you are in town?” I was unable to form words. I locked eyes with her as her legs were up around my shoulders and started to pound her. I fucked her as hard as I could and she reacted with pure lust.

Now, there are several hot things woman can say. But it would be hard to beat anything along the lines of what she said next. Simple, to the point, and hot as fuck. With our eyes locked she said “give me your cum”.

I was already close, but that put me over the top. And given how much wondering, and flirting, and teasing had occurred over the last 7 hours, she got a very large treat. I came in several jets deep inside her pussy. I have no idea what I did or said, but I would guess I was a grunting, thrusting mess of animalistic energy as I came inside her.

I stayed inside her until my cock started to soften and naturally slipped out, along with some of my cum. I rolled off her and she nestled into my arms. Our breathing started to slow and our hands gently caressed each others bodies.

“How long are you in town?” she asked with a smile…

Source: reddit.com/r/gonewildstories/comments/w3y702/mf_hotel_bar_pickup_leads_to_a_night_of_fun