An Unexpected Night Out

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.

"Nuh uh. Take the rest off."

I would have done whatever she told me; I was so turned on that I thought I might cum right there. I quickly stripped, revealing my rock hard cock that pointed out and up. Ana pushed me back into the chair, placed a pillow to kneel on (When did she grab that? I thought) and began kissing my abs and thighs.

"Tell me what you want," she demanded

"I want you to suck my cock."

"I don't think you want it. I think you need it," she said seductively.

She slowly took my cock into her mouth, and I let out a loud moan, "Fuuck."

Ana continued slowly, swirling her tongue around my head, licking beneath it, and taking my cock as deep as she could. After several repetitions of this my cock was glistening, and Ana stood up and began to strip from her jeans. She turned and bent over while sliding them down. Matching black lace panties dressed her thick ass. She turned to face me, her eyes oozing pure sex. The sight of her wide hips, suckable thighs, and sexy stomach were driving me crazy.

Ana returned to pleasuring me, now in just her bra and panties. What a sight to behold. She bobbed her head up and down on my member while slowly stroking and twisting my slippery cock with one hand. She started going a little faster and a little faster, and the build-up was almost too much to handle. If I hadn't had a good amount to drink, I would have cum in minutes, yet still I could feel I was getting close.

She pleasured me for about 5 more minutes before I grabbed her gently, indicating I was ready to move on to the final act. She took my hand and led me to the bedroom. Her bed had a silver cover that matched the luxurious frame, which she threw off before laying down on her back and motioned for me to join her.

I laid between her slightly spread legs and met her mouth. We made out as I ran my hands along her body, feeling the chills on her skin as I teased her. I moved from her mouth to her ear, to her neck and to her cleavage. She arched her back as I unclipped her bra. My mouth found her nipple, while one of my hands glided down her abs and reached into her panties. Her pussy was soaking, and I began playing with her clit while I sucked on her nipples.

"Harder." She begged of my mouth. "Oh fuck, just like that."

I played with her for just a couple of minutes before I could feel her body tense and I knew she was close. I moved from her nipples to her neck, and whispered dirty nothings in her ear.

"Cum for me, Ana, I need it."

Ana let out a scream, her back arched towards the ceiling. With one hand she grasped my hand that was still rubbing her clit; the other clenched the bedsheet with white knuckles. I continued to play with her slowly; her body convulsed until eventually it was too much and I removed my hand.

"Holy fuck" she gasped, and pulled me in to French kiss.

I needed to taste her. I resumed teasing her clit and slowly made my way down her body. I peeled off her panties and kissed all around her voluptuous thighs before plunging my face between her legs. Her pussy tasted amazing. She soaked my face while I ate her. She moaned, and I felt her grip the sheets and tense with pleasure. After some time, she grabbed me tightly by my hair and pulled me to meet her slutty gaze.

"Oh my fucking god. I need your dick now," she said. "Lie on your back."

I did as she said, and she hopped on my dick without hesitation. She was so wet that I slid in with no resistance, and we both let out a large moan.

It was clear that the oral session brought Ana close to the edge again. She struggled not to squirm as she bounced up and down my erect cock. After what could only have been 10 deep strokes she collapsed onto my chest and quivered. "Fuuuuuuck." I felt her hot breath on my neck as she moaned. I continued to thrust upwards slowly during her orgasm, which felt like it lasted minutes. Once she regained composure, she squatted and began to ride me with pace. After a few minutes I could tell I was about to cum, but I wasn't ready yet.

I pulled her off of me. It was my term to be demanding. "Get on your knees for me." Ana dropped down on all fours, arching her plump ass in the air.

"Good girl." She let out a moan.

I placed myself behind her and entered her still soaking pussy. Between the sight of her slim waist and heart shaped ass and the feeling of her wetness, I knew I wouldn't last long. I thrusted slowly but forcefully, each movement met with a moan from Ana. After a couple of minutes, I was feeling close, and fortunately I could tell Ana was too. I grabbed her hair, pulled her head back towards mine, and placed my tongue in her mouth. "You're gonna make me cum" I whispered in her ear.

"Oh fuck, me too."

Our rhythm and volume increased as I continued to thrust.

"Oh fuck oh fuck," Ana moaned.

"Fuck" I gasped.

I reached around and clenched Ana's tit with one hand and her waist with the other.

"I'm gonna cum."

"Cum for me James!" she screamed

I erupted with the full length of me inside of her, and Ana yelped and shook with another orgasm. I pumped out load after load, overcome with sexual euphoria for 30 seconds. The sound of our breathing filled the room as our bodies stayed joined. Finally I slipped out from her, and we collapsed next to each other on the bed.

We met eyes and burst into smiles. "Holy fuck" I said. "That was amazing."

"Seems like we were both minute men tonight?" she giggled. We laid against each other for a while before cleaning up and cozying up to sleep.

I woke up with Ana laying against my chest. It was an amazing feeling to wake up to. I couldn't help but admire her gorgeous features while she slept. Just the sight of her hair, her eyes, and her mouth filled me with joy. She arose shortly after me. We stared into each others' eyes and smiled. We both knew this would not be the last time we would share such an amazing time.