I'd never been to this bar before, of course. Ashley had picked it. Mostly because I live a couple of hours away, so this was her turf. She had picked well.
It was what I call an upper end dive bar. A dark wood, L-shaped bar with twenty or so stools. Shelves on the wall behind it filled with glassware that hadn't been used or cleaned in a while and bottles of lightly used or as yet unopened liquor. There were bottles of wine on the back counter along with various and sundry barware. There were a couple of well stocked beer coolers. They had 20-30 beer taps available, a few standard domestics, but mostly craft and some imports. The fixtures throughout were institutional and battered but mostly in good repair. Overall, the place was clean, diligently but not lovingly so. Some details were consistently overlooked or just plain ignored as unimportant.
Like any good dive bar, there was a jukebox, dart boards, some old video games and, of course, several pool tables. Like everything else, the tables were battered from years of hard use. But the felt was new and there were plenty of cues and chalk available. Like any good bar of the sort that had forty plus years of life, it had a distinct smell: old beer, stale cigarettes, happy times and not a little regret.
It was a weeknight, so the crowd was relatively sparse. I spotted her quickly, seated at the corner of the bar. It helped that we had exchanged pictures and she was wearing the outfit she had described; dark blue skinny jeans and a low-cut white t-shirt. Her long brown hair was swept alluringly over her shoulder, exposing a lovely neck.
You see, this was the first time we'd actually met in person. We had connected on a website during the early days of the Covid lockdown. It wasn't a mainstream dating website, so we already had a pretty good idea what the other was looking for. We fleshed that out even more over the weeks that followed. Compatibility didn't seem to be a likely issue, but there was still some mystery there.
As I approached, Ashley's head turned as if she sensed my presence. When she saw me, a little smile appeared briefly, then she bit her lower lip as she slid off the stool. She took one last step toward me and we were face to face. Ashley is tall, 5'9" to my 6'even, so she barely had to reach up to give me a short, but also somehow hungry, kiss on the lips as her arms went around my neck and mine around her trim waist. We both smiled as she whispered, "So nice to finally meet you, Raphael."
"You have no idea how happy I am to be here right now, Ashley. I've been thinking about this for months. I honestly didn't know if it would ever happen. How are you doing?"
"Honestly, only a little nervous. I'm so excited. My pussy has been wet since I woke up this morning. I could barely get anything done while I was working. You have me very distracted, sir..."
I grinned wickedly and said, "That's my good little slut. You just can't wait to get that pretty little pussy and gorgeous mouth full of strange cock and cum, can you?"
"What about my face?" Ashley said with a little pout. "You promised to give me a face full of cum, too."
"Damn, lady, you are going to hold me accountable, huh?" I grinned. "The woman wants what she wants, I guess. Sit down, babe, I think I need a drink." With that she turned away and I placed my hand on her firm ass to help guide her onto her seat. She took a quarter turn in her seat, crossed a knee and leaned into me a bit, giving me a view of a very pretty white lace bra, which was already pretty obvious through the thin material of her top. Ashley has ample, not huge, very firm breasts, which are pretty perfect and get a lot of attention. There was just a hint of pink areola peeking from behind the lace.
"What're you drinking, babe? Pinot?" I asked.
"Nope, merlot. What're you gonna have?"
"I think a double bourbon is in order to start the evening." I got the bartender's attention and placed my order. Then turned back to Ash. "Did you get checked into the room ok? How is it?"
"It's nice. Has a big bed and a shower. That's all we are really gonna need, I think," she said as she winked, then bit her bottom lip again. That made my cock jump a little. "Didn't you check in yet?"
"I did. Tipped the girl at the desk to send my bag to the room and grabbed an Uber. Guess that sounds a little eager..."
"Just a bit, Raph. I like it though," Ashley said behind sparkling eyes. My drink arrived and I took a big sip, then rested a hand on her knee as we talked. We already knew a lot about each other, but as in most online meetings, there was a lot unsaid. Some for safety, some to keep the excitement of anonymity and mystery intact.
So, we learned some things about each other. But there was a lot of laughter and heavy flirtation going on. Luckily, there was obvious chemistry, too, considering the way we wanted this evening to turn out. And, let's face it, no matter how good someone seems in text and pictures, you never really know how that will actually translate in real life. I really wasn't worried about Ashley. After an initial hiccup, I became very comfortable that she was exactly who and what she claimed to be.
Ashley had been playing on sites like the one we met on for a long time. Probably longer than she legally should have, according to her. She used them to explore some kinks that she felt like were better left as fantasy, for a lot of reasons. But, recently, she had gotten the idea that it was time to think about changing that situation. She said I had a lot to do with the decision.
Ashley was comfortable with me online like she hadn't been with anyone in the past. She said I made her feel wanted and safe. I didn't judge her desires, accepted them as healthy and shared them almost exactly. And, she said, I suggested that I would like to meet, but she never felt pressured that if she didn't meet me, I was going to get bored and disappear. I enjoyed our interactions and they worked well with my busy work travel, quite honestly.
The reason I thought Ashley still might be concerned is that she has a thing for older men. Significantly older. At least ten years. And more. And I was comfortably over that benchmark. So, yeah, you never know how that is going to turn out. But I am naturally lean, decent looking overall and present pretty well. So far, the perpetual smile and sparkle in her eyes made me think she wasn't disappointed.
So, we sat there and talked and laughed (ok, giggled a lot) and flirted outrageously and noticed the effects we were having on each other. Eventually, I ordered another round of drinks. Then Ashley asked, "So, how is this going to go, Raphael? It's still pretty early for the cinema. We don't need to rush over..."
"Well, I'm thinking that I don't want to share you with anyone tonight until I've had some quality time with you by myself. Call me selfish. I was thinking we could finish these drinks and head back to the hotel for a bit. And still get there plenty early for the show," I said with a cool smile as I looked into her bright eyes evenly.
"Hmmmm. I don't think that would do at all. You know better, mister," she teased with a glowing smile. Then she turned to the bartender and asked, "Would you watch our drinks and my bag for a bit?"
He said of course. Ash slid down off her stool, took my hand and said, "Follow me, lover..." and started toward the back of the bar.
I followed Ashley as she walked into the men's room like she owned it. She said to the two guys, one at a urinal with his dick in his hand and one at the sink, looking at her dumbfounded, "Anybody need this stall? We're gonna be in there for a bit. No? Good. Come on, honey..." And I followed her in...
Ashley squeezed into the back corner, between the toilet and the wall, to give me room to push the stall door closed. Then she stepped back to me and we were kissing, desperately. We'd both thought about this. Through the weeks and months of lockdown. The hours of describing to each other what we liked and wanted to do together. And with others. Many others. And all that came out in that kiss.
My hands went to the waist of her jeans, fumbling briefly at the button, then they were open, the zipper slid down smoothly and my hand was sliding over her waxed mound. As my finger found her clit, circling it briefly, her hands were undoing my belt and working on the button. But I spun her before she could finish.
As my fingers dipped into her sex for the first time, my lips went to her neck and I whispered, "Raise your shirt..." I kissed her neck and ears as she used both hands to lift her shirt over her tits. As I fingered her tight, slippery pussy, she reached around to undo her bra, then dropped one to my crotch, grabbing my hard cock through my jeans. As she did her best to jack me in the awkward position, my fingers found her hard nipple while my other hand thrust two fingers in and out of her cunt roughly.
We were both breathing heavily already, hearts pounding. Ashley started to moan loudly as I mauled her cunt and tit. She started to grind her ass back onto her hand that still grasped my manhood. As I nibbled on her neck, there was a sound behind us. I felt her head come around, then she giggled and said, "Hi, fellas. Liking the show?"
Of course, I had to look. The two guys had levered themselves up and were watching over the top of the stall. Naturally. What else were they gonna do? It's what Ash had counted on, I'm sure. Being watched by strangers was a big kink for her. And me. But not the only one.
That turned things up to a different level. Ashley pulled my hand out of her jeans, turned and shoved me against the other side of the stall. She kissed me again. Hard and deep. While her fingers finished undoing my jeans. Then she slid smoothly to the floor, taking my jeans with her. As she did, my cock flopped forward onto her cheek. Ashley squealed in delight as I painted a wet pattern of precum across it.
She looked up into my eyes as she took my cock into her hands for the first time. She wrapped both hands around it and let her eyes slowly drop to look at it closely. Then her eyes moved back to mine and she said, "He's so thick, babe. He'll feel so good inside me..."
Then, she reached out with her tongue and took a tentative lick. Not out of nervousness. Because it was her first taste of me and she obviously wanted to savor it. She collected the wetness on her tongue and pulled it back to her lips, stopping there to smear it on them. Then she leaned forward and planted a soft kiss right on the little slit on the top.
She took the whole head in her mouth, sucking on it lightly as she swirled her tongue around it. One hand dropped as the other started to stroke me slowly. Her head started to bob on me. Slowly at first, but the pace quickly increased. She knew what she was doing. I didn't have to say a word.
The rhythm was perfect. Just enough hand, but not enough to be distracting. And deep enough to cause her to drool without being so sloppy it wasn't sexy. Then something happened...
Ashley stopped abruptly and gasped. She looked up at me with a wicked grin on her lips and said, "Well, I don't have any fingers in my pussy. And I assume you can't reach it from there?"
I smiled back and said, "Ummm, no. My arms aren't quite that long..."
"Oh," she moaned, "this is working out nicely..."
