I'd been single for about a year at this point, and I had fallen out of the habit of going out drinking to meet people frequently. Too many hangovers and strikeouts.
But tonight I was feeling moody and a little alone after two friends had moved towns in the last month. I was just hoping to have a fun night, meet some interesting people, and go home. Anything past that would just be icing on the cake. I decided to hit a neighborhood bar that was probably my favorite spot. The 15 minute walk was chilly but not uncomfortable. This bar is small, dark, quiet, and has no frills, just a single wooden bar and a handful of high top tables.
I sat at the bar and ordered my first drink, a gin and tonic. I sat for around 15 minutes, originally making small chat with the bartender but the bar quickly filled up so only a few seats were remaining. The seat to my left was empty when a beautiful woman approached and sat down. She was older than me, with thick, dark wavy hair and a tan complexion. She was wearing a simple outfit that suited her nicely: a leather jacket over a white tank with black jeans and short black heels. Her clothes hugged her body, and I could tell she had a nice waist and wide hips. I could just make out the crease of her upper thigh as she sat, which instantly turned me on.
She glanced at me with some interest, but she wasn't as infatuated as I, probably obviously, was with her. I was racking my brain trying to think of what to say to her.
"Hey"
"Hi," she returned, plainly.
"I'm James."
"Ana." Her voice was soft and kind.
I decided to be straightforward. "You seem like a nice person to have a chat with."
"Really? I'm probably twice your age," she said in a tone that I had a difficult time distinguishing between cold and playful.
"Yes really, and there's no way you're twice my age," I said earnestly. I knew she was older than me, but I wouldn't have guessed by that much.
"Do you want to bet?"
"Deal, loser has to get the next round."
She required I spill my age first, and I told her I was 27. She replied that she was 49: "I told you so!" she bragged.
"That's not twice my age!" I argued back.
"I said ~almost~ twice your age, so you owe me a drink!"
I decided to compromise, but told her only if she would get the round after that, which I was glad she agreed to. "But, you do know that that means you have to chat with me until we finish the first round?"
She smiled a gorgeous smile and teased me about how tall of an order that was. Any coldness I had previously perceived had faded away; our eyes agreed that we were now both playfully flirting.
We kept chatting well past the 2nd round of drinks. While we were far apart in age, we had a commonality of feeling a little alone in our city. She was divorced, though not recently, and her youngest kid had moved out in the last year. We talked for a long time about traveling, eating, music, and dancing. The conversation was lively; after an hour my cheeks hurt from how often I smiled at her. At this point we were both fairly tipsy, and I asked if she wanted to go somewhere to dance. She agreed and, after closing out, I took her hand and led her out the bar to walk to the new spot.
It was a quick walk, about 8 minutes, but it had gotten colder later into the night. This gave us an excuse to cuddle up as much as 2 people can while you are walking together.
Eventually we got to the new bar. It was also small and dark, with pink lighting throughout that set an intimate but playful mood. There was a single bar and a small dance floor in the back that could hold about 40 tightly packed bar goers, which we headed to after getting a round of drinks.
The bar played a combination of mostly Latin music and RnB, which we knew we both liked from our previous chats, and which gave a good excuse for some intimate dancing.
Neither of us were great dancers, but we weren't bad either. We both had a good sense of rhythm but no real experience outside of the club. We danced casually for a while, mixing in salsa, twirls, and whatever else felt right in the moment. She would put her arms around my neck while I grabbed her waist, looking into each others' dark brown eyes while we danced.
The feeling of intimacy grew, and I pulled Ana in close for a kiss. It was passionate, but not sloppy. Her lips were soft and plump. Our tongues glided against one another's for several seconds before we both pulled away and let out a big laugh. It was dark but her smile lit me up, and I pulled her in for another kiss. I ran my hands down her side, feeling the curves of her waist and hips before cupping her ass. She curled one hand around my neck and placed the other on my abs, which sent chills down my spine. At this point I was extremely aroused, and Ana could tell.
Ana turned around and, with one hand grabbing my hair, began dancing up against me, rubbing her ass against my jeans that were suddenly tight fitting in the crotch. From here, our dancing became sluttier. We continued to make out, laugh, and feel our bodies against each other.
After some time, our lustful gaze met; we silently agreed that we were both ready to go somewhere more private. I guided her to the bar, closed out, and asked if she'd like to come back to my place.
"Let's go to mine instead, it's just a couple blocks. I think you'll like it."
Sounded great to me.
We marched through the cold night, giggling and sneaking feels of each other, until we approached a newly-constructed high rise. We took the elevator up 30 floors where Ana brought me to her room.
Her apartment was beautiful, with huge glass windows all around. She dimmed the lights when entered, setting the mood right where it had left off at the bar.
The kitchen was to the right of the entry, and Ana asked if I wanted anything to drink. I declined by lifting Ana onto the kitchen island and meeting her lips. Our tongues danced passionately. I lost sense of time, when suddenly Ana pulled away, and, playing to our age dynamics, ordered me to the dining room where she pulled out a chair.
"Sit."
She began to tease me, moving her hips to a seductive rhythm, kissing my neck, and rubbing up against me. She straddled me and pushed her tongue into mine while she ran her hands down my chest and abs. She pulled off my shirt and ran her hands along my bare chest and abs before doing the same, revealing a sexy black lace bra that showed off her round tits. She grabbed me by my hair and pulled my face to her breasts, and I passionately kissed her cleavage. I started to grab at her bra, aiming to move to her nipples, but she pushed me back against the chair and stood up.
