Weekend With an Older Woman

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Online acquaintances hook up in a tourist haven.
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Disclaimer:This is a work of fiction and any resemblance to any person or persons living or dead is purely coincidental.

I was having an argument yesterday with a friend over whether or not pot was legal in Portugal.

It reminded me of a woman with whom I shared a too few nights and many many fantasies. I remembered the way she tilted her face, the way she smiled her naughty smile and the words she breathed in my ear at our first encounter- "Anything is legal inside my car."


We had been chatting online for about a month after meeting and talking on a social website. Our chats weren't explicitly sexual, but there was always a lot of flirting which often left me with a hard on at the end of it.

She was a very curvy woman, 16 years older to me. Worked out a lot in the gym, did yoga and had a fabulous sun kissed body. Her best features were her long toned legs which any girl would die for. She had been divorced for a couple of years and lived alone. By profession she was a social worker.

After a few more chats over the net we exchanged phone numbers and our conversations became much steamier. they usually started with her describing what situations turned her on and continued with me telling her my fantasies about what I wanted to do with her.

Our talks, late at night, after the day was over used to make her moan and touch herself...her breath heavy through the phone and her fingers furiously rubbing her dripping pussy.

I soon got to know exactly what turned her on and what didn't and this went on for several more weeks till one day, unexpectedly, she called me in the morning.

It was about how she and some of her girlfriends were coming to a beach side tourist paradise close to my college. And she wanted to meet up. You can imagine readers that I will thrilled at the prospect. But other guys who have been in such a position will also realize that I was very nervous as well.

This gorgeous experienced woman wanted to meet me and I was afraid that I didn't know enough to measure up, having been with only a few women and none as old as her.

Needless to say it wasn't enough of a deterrent to stop me from getting on my motorcycle and setting out early morning to avoid the afternoon sun.

After a long and pretty enjoyable ride, I checked into a hotel and rested up because she wasn't arriving till evening.

Evening came and she called me up. She was on the north side of town, so she wanted me over there. I bathed, shaved, put on some cologne and made my way over there.

It was night time and the environment was very festive. Bright lights all around with lively beats from bars that lined either side of the road all the way to the beach.

Couples walked hand in hand, hippies openly smoked pot. All in all, it seemed like paradise. And the women? Even with a shirt open almost all the way and shorts, I felt overdressed for the occasion.

Soon I got another call from her number. She was waiting for me at a bar called Cape Town, having got away from her friends. It didn't take me too long to find her. She was sitting on a bar stool, a beer in front of her, wearing only a black bikini and harem pants, her black hair falling beautifully in a hime-cut down her shoulders. She had really taken in the atmosphere of the place very quickly.

She came over to me and gave me a smile and a hug when our eyes met across the bar and I was left smitten, almost drunk with the perfume of her hair.

It was a little awkward meeting face to face for the first time, but she was a great conversationalist and soon put me at ease. She talked about all the places she had been to since evening and about her journey and everything while I sat there listening closely but always getting distracted by either her expressive brown eyes or the depths of her cleavage.

After a while, as the alcohol kicked in, the conversation became more comfortable and physically we could feel a tension between our bodies. Soon she had linked her hand in mine and I was nuzzling her neck. She was laughing and giggling at almost everything I said. We were completely lost in each other.

After a while, she suggested we drive down to a club close to her hotel for a dance and a few more drinks. I left my bike in the parking there and we got into her rented car, a red sedan.

As we were driving, I got out a joint I had rolled before coming. Being a social worker, I knew she didnt approve of drugs so I asked her if it was okay to smoke it in the car.

Her answer was leaning over to my ear, a tilt of the head, that sensuous smile "Anything is legal inside my car."

No more words were spoken. She pulled into a dark alley and all inhibitions were lost as we pounced on each other like two feral beasts. We crushed our lips together in the first kiss of the night and fell clumsily into the backseat.

As I kissed her, I felt her hands groping inside my shorts and heard her moan as she grabbed my already hard cock. Untying her bikini, I cupped her breasts and took her nipple in my mouth sucking it as she worked to pull down her pants.

It was very cramped inside but we managed to get naked and as she spread her legs under me, I guided my cock to her pussy and eased inside her.

"Mmm..." she whimpered, as her beautiful eyes filled with need and desire looked into mine and I couldn't take any more.

I began working my pelvic muscles, thrusting deep inside her as her arms wrapped around to pull me closer. There was to be no lovemaking right now. There was a fire burning inside both of us that needed to be quenched. As our rhythm increased so did her moaning. Soon we were covered in sweat and our slick bodies slapped against each other with a wet sound as we fucked.

My hands grabbed her tight ass as I was getting close to cumming. Seeing her face, I knew anything would be enough to push her over the edge. As I thrust inside her with long, deep strokes, I pushed my middle finger inside her ass.

That opened the floodgates and her long nails dug into my back as her body trembled and shook and her walls squeezed my cock. That pushed me over too and I shot hot white semen deep inside her pussy.

As we separated, panting and breathless, I saw my cum oozing out of her shaven pussy. The sight was almost enough to make me hard again. But what she did next was even better. She reached down with one hand, rubbed it in the mix cum and pussy juices in her crotch and brought it to her mouth. Then as my eyes turned glassy and mouth went dry, she brought it to her lips and slowly licked it with her sweet pink tongue.

She turned her body and crawled over to take my semi-hard cock in her hands and licked all the cum off. If I could have cum again then I would have but I still got very hard.

Only 10 minutes had passed and it seemed like it seemed like an age. The whole night was still ahead of us. Things only got better after we reached her hotel room. But that is a story for another day.

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chytownchytownalmost 2 years ago

****Hot FLASH story. Thanks for sharing.

AnonymousAnonymousabout 12 years ago

Everything's better with an older woman...everything!

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