Ride Sharing

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She had been flirting with me for five years. Though I was sorely tempted again and again, I had been trying to avoid an entanglement, while remaining friends and colleagues.

And now I found myself in the back of an UberBLACK car on the way to the airport with my right hand between her legs, my middle finger deep in her warm wet pussy, my thumb thrumming her clitoris, and my left hand fondling her generous D-cup breast through her silk shirt, while she moaned into my mouth.

“I need this so bad,” she said.

The driver turned up the electronic dance music on the radio.

Andi lifted her hips against my hand in rhythm to the music and pulled my head back into a deep, tongue twisting kiss.

“How did I get here?”

The question floated through my head as I let myself drown in the moment.

“And what comes next?”

Truth be told, I had been fantasizing about this moment for five years, ever since Andi first recruited me to join her nonprofit board. She was smart, ambitious, persuasive, and attractive. She was about my age, and more intriguingly, for me, about my height. I’m 6’4″ and I’d never been with a woman my height. My marriage was on the rocks. My wife had agreed to an amicable divorce, but we were taking our time, planning to finalize it when our youngest daughter finished high school.

Meanwhile, I had gotten a small place across town, and I was actively looking around.

And Andi looked good.

Plus, she was touchy, in a good, warm way, which added frisson to every encounter. We were sitting in an outdoor café outside my office when we first met and she pitched me on her board. She touched my forearm and elbow while talking me into the challenge of turning around an important cultural institution in the city, a diamond that had been through a long rough patch, a seriously undervalued asset.

I like turnarounds. I like the challenge. The conditions seemed right for a reasonable chance at success. And turnarounds are such a great story. My life was in turnaround, too. And I wanted to think I had a reasonable chance at scoring again.

I agreed to join her board. And when we parted, Andi gave me a hug. Was it just a friendly hug? Maybe. But it was borderline, I thought, as she walked away.

She definitely pressed her tits against me, and her body fit into mine in a way that startled me and gave me an instant woody. And then it was over. She smiled and said she’d see me at my first board meeting in a month.

As she sauntered away, I thought about her splendidly shaped pendulous, but firm breasts, bigger than my wife’s or any woman I had been with, which had been on display in a sleek silk blouse, unbuttoned to reveal tempting smooth cleavage. I watched her long stride and couldn’t help but imagine what it would feel like to run my hand up those long legs. And how would it feel to be fucking a woman who was built like me?

Now I had a real hard-on. And I had to sit for a while and read the newspaper until it went down and I could go back to my office.

Ever since, I had been pretty sure she wanted it. But I’ve always been unsure about reading women, and probably too cautious my whole life. Blame it on respect. Or maybe I’m just a pussy.

And she seemed to act the same way with a lot of men, which left me confused and hesitant. The close warm hugs. Her tits rubbing against my chest. Casually or meaningfully? The kisses uncomfortably close to the mouth.

I was sorely tempted a few times ataşehir escort bayan when we were alone in her office to push her back against her desk and take her right right there. Or in the parking lot on the way back from a fundraising meeting to reach across and fondle her ample tits. Or following her up the ladder to inspect the roof of the organization’s historic headquarters downtown to reach up between those long legs. I was sure she was tempting me. Maybe, I thought. I was paralyzed.

“Down boy, this is a professional relationship,” I reminded myself. I was, in a very real, fiduciary and legal sense, her boss, as a member of her board. We ran in the same professional circles. I was afraid of any whiff of impropriety, conflict of interest, let alone sexual harassment.

Plus, she was married. She rarely talked about her husband, though she talked about her sons all the time. I wondered what he was like. I was intrigued that his name was John, too. That irked me. Then I met him. He was instantly forgettable. I wondered how he landed her. And that irked me more.

But by then I was well into a good, steady relationship, too, with a great woman I could see spending the rest of my life with. I was in love with Catrina. And I didn’t want to fuck that up. She was smart, fun, cool, we shared a lot of interests, and the sex was great, the best ever, in fact, over and over again. And, unbelievably, it kept getting better. She kept in shape. She had a great body. I loved everything about it. But she was shorter than me, as all of my girlfriends had been throughout my life.

And so I fantasized. There was no harm in that, I told myself. Especially when Andi casually rubbed her tits against my upper arms at a reception as she introduced me to city officials or donors, or against my chest when she kissed me goodbye on the cheek after a meeting, and the kiss slipped to the edge of our lips and then was gone.

I left the board after a three-year stint. We had turned the organization around and that was what had interested me. It was on a good, steady growth track. And Andi could take it from there. We still met from time-to-time when she was in town or I visited the city. We gossiped and I offered free advice, which may or may not have been worth any more than she paid for it. I always bought the drinks. She was still always touchy in the same friendly way. But tonight it had gone further.

We had toured a historic building her organization was thinking about buying. We talked about the structure of the building and the deal, and her strategy for expanding from the city into a new town. She seemed subdued, which was not a word anyone would usually ever associate with Andi.

“How are you doing otherwise?” I asked, as she sipped her red wine.

She looked at me with sad eyes. Her lips trembled. She dabbed at the corner of her eye.

“It’s been a really rough few months,” she said. “The boys are doing great.” She perked up and seemed ready to launch into her usual, overly enthusiastic litany of their accomplishments in high school, good grades, success in sports. She stopped. “But John and I…”

I let the silence linger. Andi new about my divorce and my new relationship.

“I don’t think I can go on,” she said.

“What’s going on?” I asked.

“I caught John having an affair. It was obvious. In our own house!” she cried. “He didn’t deny it. He’s begging for forgiveness. But I don’t think I can. It’s over.”

“It escort kadıköy may take a while,” she said. “We haven’t figured out what to do. The boys…”

“They don’t know,” she continued, shaking her head. “I haven’t asked John to move out, yet. I guess we’ll keep the house together until the young one has left for college in two years. I just don’t know what to do.”

I took her hands. “I’m so sorry. I know how painful this can be,” I said, looking in her eyes. “If you need a good lawyer, I’ve got one. She was great for the amicable separation we wanted. And we took a couple of years, too.”

She looked at me with tears in her eyes, and pulled me close for a hug that lingered. Then she leaned back.

“Thank you,” she said. “For everything.”

She lifted her glass to me and then drained it.

“I guess I better catch that flight.”

“I’ll give you a ride.”

“You sure?”

“Yeah, it’s on the way home. We can share an Uber.”

And that’s how I found myself here, with my finger deep in her pussy, probing her G-spot, her luscious tit in my hand, her tongue in my mouth, as she squeezed my hand between her legs and rocked gently in the back of the car with the dance music playing.

We had just gotten into the back of the car. It was dark. We were underway with the city lights passing by in time to the music.

She leaned over. “Thank you,” she said. She gave me another hug. And then a kiss on the side of the mouth. But this time she moved to a full kiss on the lips and opened her mouth softly. Her lips enveloped mine, as her hand ran up the back of my head and pulled me close. I felt her tongue tentatively probe my lips. I opened my lips and let her in.

The next thing I knew we were deep into French kissing. She was a good kisser. It was the one other thing I missed with Catrina. She was OK at kissing, but not really into it as often as I would like. But Andi was into it, deeply. She wouldn’t let go.

“Andi,” I said, as my cock twitched.

“Shhhh,” she said, and pulled me back into the kiss.

It was then I let myself go and found her breast. It was unbelievable. Like something from a dream, full and heavy, soft and firm. It was bigger than I could hold in one hand. It had weight. Yet such grace. I felt her nipple harden under the layer of silk and lace. I squeezed it gently but firmly. She moaned into my mouth. My cock hardened.

The driver turned up the music.

Andi took my hand from her breast, while holding me in a deep ongoing kiss as she explored my mouth with her tongue and lips. She moved my hand down her torso between her long legs and up her skirt. I felt her firm thighs through her nylons, and then where the stockings ended, the cool flesh of her upper thighs. My cock jumped. She guided my hand up further to the moist heat between her legs. Her panties were wet. She held my hand there and rubbed it against her pussy.

My fingers trailed against the edge of her panties. I felt her swollen labia underneath the silken surface. She moaned into my mouth again.

I slipped my fingers under the edge of her panties and between her wet lips. She was so wet and slippery. My fingers glided between her labia. She felt delicious. I felt her clitoris hardening instantly as I reached the top and glided back down. It was then that my middle finger slipped easily deep into her. And she bucked and then pushed against my hand and the seat. And I gently thrummed her clitoris with my thumb. bostancı escort She squeezed my hand between her legs. I squeezed her nipple and fondled her breast in my other hand.

She moaned. The driver turned up the music.

And then she came suddenly, spasmodically, squeezing my hand between her legs, rocking violently against it, sucking my tongue into her mouth, silencing a scream.

“Oh my god,” she said, as she leaned back against the seat. “I’ve needed that for so long.”

We were approaching the terminal.

“Thank you,” she said, as she leaned over to hug me again.

It already felt a little more like all the other times: ambivalent. Professional? Friendly? Forward? Sexual? With Andi it had always been hard to tell, until just now.

And then she was back in business mode again. Except for one thing.

She reached down and squeezed my hard-on, which was stretching my pants uncomfortably.

“Next time?” she said with a sly smile.

The driver and I watched as her long legs carried her into the terminal. She turned to wave and was gone.

“Home now?” the driver asked.

“Yep,” I sighed and slumped in the backseat.

The rest of the trip was quick. We were there in fifteen minutes. I had time to smell her on my fingers and drink her in, imagine her body under mine, her long legs wrapped around my back. I rubbed the tip of my cock and felt the sticky wet spot of precum on my pants. And then we were home.

“Thank you,” I said, as the driver jumped out an opened the back door. I fumbled for my messenger bag and looked around to make sure I wasn’t leaving anything.

When I got out and stood up, the driver had a big grin on her face.

“If you ever need a private chauffeur, give me a call,” she said, handing me her card.

“Sorry about that,” I said. “I wasn’t expecting that.”

I looked at her and then away embarrassed as I realized she was exactly another type that I had never had the good fortune to fuck, tall, too, but thin, in skinny jeans and boots, but boyish, nearly flat chested in a tight fitting button down shirt. And I wanted her, too, instantly, right there. I felt out of control.

“No worries,” she said. “I see a lot of stuff happen in the back seats of my rides. And, actually, that was just about the nicest ever. Women appreciate a man with a nice touch. Especially when she comes first.”

She glanced down quickly at where my pants stretched out in front of me, and the dark wet spot shined in the streetlight.

“Good night,” she said. “Just let me know if you ever need a ride.”

She hopped back behind the wheel and pulled away as I turned to the front door.

I let myself in as quietly as possible. I went to the bathroom and stripped.

My cock was still hard as a rock and slippery and sticky around the head. I rubbed it and thought of Andi, and my balls tightened and I got even harder. I could cum in an instant, I knew, but I worried about waking Catrina. And I didn’t really want to settle for masturbating right then. So I washed up, brushed my teeth, and tiptoed to bed.

I snuggled up to my girlfriend’s warm back and spooned her, reaching around to cup a breast.

“Mmmm,” she said. “Welcome home, baby.”

We were different sizes but we fit together perfectly, her body coiled inside of mine.

“What’s this?” she said sleepily, reaching back to grab my boner.

“Did you bring me a present?”

“Uhuh,” I grunted. “Just for you.”

“What have you thinking about?” she asked as she held it against her pussy and rubbed herself against it.

“You, baby,” I said. “I missed you. All day long.”

“You’re lying, pooky,” she teased, as she pushed back against me and my cock slipped inside her.

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