Sex and the Windy City

This was new to me. I’m not an extrovert and tend to keep to myself. But I have needs, the same needs of most men in the prime of life. Most of those needs were not met since my wife unexpectedly died a year ago.

There are plenty of social media sites to meet women. Some are people wanting a mate for life, others short-term arrangements. I was not looking to remarry. I just wanted to meet some women and have fun. Cindy wanted to have fun too. The only thing was, she was married, although that didn’t turn out to be a deal-breaker.

It isn’t that Cindy is in a loveless marriage. She is thirty-four and sees life passing her by. She is bored and has little to look forward to. This brought her to browsing on a social media site where I was doing the same.

In a short time, we were exchanging everything from A to Z with ‘M’ for movies and ‘S’ for sex. Cindy was honest about her life at home and in bed. She gets off masturbating more often than getting satisfaction from her husband, Tom. Cindy told me how she sometimes fantasizes about having other men in her life. Once she asked Tom what he thought about having a threesome. He said he’d think about it, but the subject never came up again.

Well, to make a long story shorter than a Victor Hugo novel, we met. I told her to take the ‘L’ to Diversey and I’d meet her on the street below the station. We agreed to have lunch and talk. Cindy didn’t know what I looked like. I only knew she was a brunette with blue eyes. We both loved surprises and wanted it that way. To be sure we didn’t miss each other, she wore a chartreuse scarf. I wore my signature fedora.

“Oh my God,” were her first words. “You look just like Humphrey Bogart.”

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I scowled like Bogie and said, “You are pretty, but you don’t look at all like Lauren Bacall. You’re more Ingrid Bergman. Here’s lookin’ at you kid.”

She laughed and said, “We’ll always have Chicago.” I took her hand and gave her a peck on the cheek. We walked a few blocks before finding a quiet tavern that I remembered from college. Neither of us knew how to start the conversation so not much was said until we ordered a drink. She ordered a glass of Chablis and I asked for a Manhattan with a twist. She took off the scarf and I laid my hat on an adjacent chair. She wasn’t a raving beauty, but Cindy was cute-looking years younger than thirty-four. She had a captivating body that enticed me.

The drinks helped us relax and she said, “You have a gorgeous head of hair, Bogie. My husband is losing his.”

“Thanks, Ingrid. Let’s not talk about spouses.”

“So, you are married.”

“Was. She died a year ago in February.”

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“I’m sorry.”

Changing the subject, I said, “My God, you have beautiful eyes. They’re like the azure blue waters of the Caribbean.”

She smiled with a radiant smile and asked, “Do you go to the beach?”

“Nope, I’d rather be in my boat out on the lake.”

“I’m not much of beachcomber myself but I like to lounge on a beach chair with a book and get a tan. Do you have a yacht?”

“Well,  it isn’t exactly a yacht. It’s a small cabin cruiser.”

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“It sounds like fun. I’d like to see it. Like I told you, Bogie, I just want to get some fun out of life.” And that is when our affair began.

“How about this Saturday?”

“Cindy took a minute to think about it and said, “That would work. Tom golfs this Saturday. I’m going to need to do some shopping first.”

“Shopping?” I asked.

She giggled. “I haven’t bought a swimsuit in years. My old one is a dumpy one-piece. I need something more fashionable to cruise the lake with a handsome captain.”

We met again at Burnham Harbor Yacht Club near the Field Museum. She wore a summer dress and sandals but what was underneath was definitely not dumpy. It was an exotic neon-colored bikini with the briefest of fabric. I told her how fantastic she looked. Cindy said she had seen it in Cosmo, “You know Cosmopolitan, the magazine ladies read. It cost a bundle, but I had to have it! Do you think it’s too skimpy for Chicagoan’s sensibilities?”

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“Maybe, but not mine,” I said. “Less is more in my book.”

Getting a boat ready to go out on the lake is always time-consuming. There’s the fuel and checking the gear and loading the food and the water toys. It took over an hour with her help. I thought she was going to fall out of her top each time she bent over to pick up something. From the rear, she was practically nude with a small strip of cloth riding up her crack.

About a mile offshore, I asked, “Did you bring a companion book to sun yourself?”

Cindy smiled and said with a sparkle in her eyes, “No. I didn’t think that was what we came for.”

I had to think about that for a minute then she added, “Does this boat allow for skinny dipping? I like to get an all-over tan.”

“Well, when we get further from shore where we’ll be alone, then the maritime rules apply.”

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“Really? And what are the maritime rules?”

“In the case of nudity, there are none. It’s up to the captain.”

“And what does the captain say?”

“I’m all for it and so is the boat.”

So, I drove out onto the lake in the middle of nowhere, cut the engines and we got naked in the sun. Cindy had a healthy set of tits, nothing to be ashamed about, and a nicely shaved pussy. She looked great. I mixed a jug of Manhattans for myself and brought a bottle of chilled Chablis for Cindy.

Only one other boat sailed past us as we drifted aimlessly in nearly calm waters. I had to laugh when she stood up to wave. Either Cindy forgot she was nude, or she was an exhibitionist. The gawkers swung past us for a second look, gave us a thumbs up, then they were on their way leaving us to enjoy the afternoon without further interruptions.

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We had been on the lake long enough for both of us to show a little sunburn. Cindy said, “How about if you show me the inside. I need some shade.”

I showed her the stateroom and a few of the other amenities. “This is nice,” and she sat on the bed. “Do you sleep here?”

“I have but not often.”

“Do you bring your girlfriends here?”

“Only my wife before she got sick.”

“You must be lonely,” Cindy said provocatively.

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“I am sometimes.”

“I mean for a woman,” and she slightly opened her legs.

“Yes, but I guess you know that from my e-mails.”

“Do you think I’m pretty?”

“Of course. You have a beautiful body,” I said moving next to her on the bed.

“I get lonely too at times when Tom isn’t around or isn’t in the mood.”

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“Are you in the mood, Cindy?”

“That’s why I’m here, isn’t it?”

“I wasn’t sure,” and my cock began to rise up like a cobra from a snake charmer’s basket.

“You look like a man that can make a woman happy from what I see down below,” then she held my hard-on firmly with one hand and cupped my balls with the other.

Just as she lowered her head to go down on me, I said, “Just a minute, Cindy. Before we go further, I have something that my wife left behind. I think you will like it.” I opened a drawer in the cabinet near the bed and gave her my wife’s vibrating egg. “It’s a Bluetooth vibrator. Put it inside while I grab my cell phone.”

I demonstrated how the app worked. “If you are anywhere near the Internet, it can be controlled long-distance.”

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After changing the patterns, Cindy found her favorite vibration and kept asking to increase the volume. She added to her pleasure by gently touching her clit but as her urges became stronger, she rubbed harder and faster moaning with each impulse. “Ooh, ooh, aah. Oh yeah, turn it up, more more!”

All of a sudden, she started screaming. I was sure her yells could be heard on Lake Shore Drive. “Oh my God! Oh my God! Oh My God! I’m cumming, I’m cumming!” It scared me half to death.

Well, it wouldn’t be her last one that afternoon. When she had enough, Cindy said, “Wow, this is fantastic. I need to buy one.”

“You can have this one if you would like.”

“I would like that but right now I would rather have you come over here and bring that wonderful specimen of manhood with you. I need a fuck.”

“Flowery language will get you everywhere, madam.” I kissed her nipples. She kissed my cock.

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I never had a woman give a blowjob like Cindy. She started slowly. Her wet lips surrounded my cock head, and her tongue gently teased the underside. Only her lips fucked the bulbous tip until she licked up and down my shaft. Little by little she took me in her mouth, holding and stroking my balls. Her mouth began to consume my organ fucking and sucking it as if she worshiped it. She took me deep holding my entire dick down her throat almost indefinitely. My precum flowed like sap from maple trees in the spring. She knew I was on the edge and held my throbbing cock tight to keep me from exploding.

“I think I’ve primed you long enough. Fuck me, Bogie. Fuck me like we were back in Paris,” and she laid back with her legs wide apart. I helped myself to a pussy that was as juicy as an over-ripe watermelon.

What I remember was how the boat began to rock as if we were in a storm and that Cindy started talking dirty which, of course, I loved. Just as I was about to explode, she yelled, “Cum inside me! Don’t pull out. Shoot me full of your hot jizz.” I was happy to oblige.

Afterward, we sipped a drink and she said, “You did better than I expected. I didn’t think you would last as long.”

“Why is that?”

“You looked pretty intense. You know, like you were frantic with desire.”

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“You could tell?” I chuckled. “You weren’t so bad yourself.” We kissed and I quickly drifted off to sleep until dinner time. Dinner was served orally with a helping of sloppy seconds. At dusk, we were back at the harbor.

Cindy sent a text thanking me for a lovely afternoon. She said her new toy was vibrating inside her and asked if we could try the long-distance feature. We eventually got it to work as advertised.

Later that week, Cindy wrote that she discovered that the toy worked wonders in her ass. She suggested I control it while her husband fucked her. We had a good time without her husband knowing she was playing with another man in her ass.

“Hey,” she e-mailed. “Tom and I talked again about a threesome. I told him there was a guy on a social media site that was looking for an arrangement like that. He wanted to know what I was doing on a social media site. I just said that I was curious.

“I said that there were plenty of people looking for alternative sex lives and this man was a widower living in the city. I have to meet him first, I explained. He didn’t like the idea and it took some convincing. I told him to think of it as an overnight loan like at his bank. Finally, he understood. So, I want to hook up with you again if that’s alright.”

“How about Wednesday night at the Trump International. Tell your husband you will be gone all night.”

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“Okay,” she wrote back. “What time?”

“7:30 and we’ll have dinner at the rooftop restaurant.”

I registered at the desk, then went upstairs to the room setting a bouquet of flowers next to the bed. When I met her, Cindy was sitting at the bar with a glass of wine. She said, “I showed up almost a half-hour early. Does that tell you something about how stoked I am? By the way, the drinks are on me tonight. Everything else is your treat. Hey, where’s your hat?”

“I left it up in the room.”

“I love that hat. You look so sexy in it. I’ll tell you a little secret. I’m not wearing something too, my panties,” she whispered.

I looked around the bar to see who was looking. No one noticed when I put my hand up her skirt and felt the tail of her Lush toy sticking out of her cunt. “Is it on?” I asked.

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“No, I thought you should have the honors.”

During dinner, there was a soft hum from her side of the table while I occasionally changed the vibes.

The first time I fucked her that night I wore my fedora. She kept yelling, “Fuck me, Bogie like you were fucking Ilsa Lund. Make me climax until I lose control.”

She quickly lost control. “I’m cumming, I’m cumming. Harder, faster, don’t stop, don’t stop,” she pleaded. I kept at it until I wasn’t able to control myself firing blasts of cum deep into her cervix.

I recovered quickly with the help of her succulent mouth. She wanted to be on top. That lasted for a long time before I turned her on all fours and plowed in from behind. After coming twice, I fell asleep before doing a hat trick.

The next morning, we ordered breakfast from room service. Cindy said, “I want to do anal before we leave. Tom won’t do it and when the three of us are together, it might be fun to do DP.”

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“Fine. Did you bring some lube?” She didn’t answer but gave me a tube to grease her butt hole. I smeared a gob on my dick and went in inch by inch. I heard her squeal, and she squirmed until I was in all the way. I often have a lot of staying power in the morning and that day was no different. I banged her for fifteen or twenty minutes before we both had powerful orgasms.

“That was fun!” Cindy said as we showered together. “I’ll text you when Tom and I are ready for your visit.”

She wrote a long e-mail telling how Tom handled our one-night stand. Apparently, Cindy told him everything including my hat and our early morning “mischief” as she called it.

“Tom got really excited,” she wrote, “and he fucked me for the rest of the night, just like when we were on our honeymoon. This arrangement is working out beyond my dreams!”

A few days later she wrote again. “How is Saturday night at the Renaissance Hotel at seven. Tom is buying us dinner.”

“Fine,” I answered back. “C’ya @ 7.”

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Tom is a pleasant guy and a little nerdy. The first few minutes with him were awkward. At dinner, he talked about his job in IT at the bank. I did most of the listening even though I had a chance to talk about my consulting business.

It got even more awkward in the room. Cindy was the one who kept us calm. Tom and I took a bottle of whiskey to the room and had a couple of shots when Cindy undressed and said, “Fellas, we are not here to drink ourselves silly. We are here to fuck. I’m putting in my pink toy. Who wants the controls?”

Tom took her cell phone and started the song “Good Vibrations.” It was Cindy’s favorite pattern. While Tom was playing with the app and Cindy was wiggling her hips, I got undressed rolling next to her sucking her nipples and stroking her clit.

“I’m ready. I’m ready,” she gasped. “Who’s first?”

I already had a throbbing hard erection, so I didn’t wait for Tom to answer. Out came her toy and in went my dick. Going slow was not o the agenda since my balls hurt with anticipation. Tom poured himself another drink and took a few pictures with his cell while I pounded into his wife. Cindy yelled and screamed like before, “Faster, faster. Get it in. Deeper, deeper, cum inside me.” When I let loose, it came out in shots like from a machine gun.

Tom looked dazed. He mumbled, “God, that was hot. I didn’t know Cindy liked to fuck like that.”

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Cindy turned to her husband and said, “Okay, dear, it’s your turn.”

Tom went in for sloppy seconds. He lasted only long enough for me to go to the john and take a piss. When I came out, Cindy was kissing him saying how much tonight meant to her.

We watched a ninety-minute porn movie the hotel offered for free. After that, Cindy said, “Boys, are you ready for more?”

“Sure,” we said in unison.

“Do you want to try DP?” she asked Tom.

“Now?” Tom asked nervously.

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“Why not?” Cindy replied. “Look, I’ve been incubating your sperm for over an hour, and I think it’s time to refresh your seed.”

“Tom,” I said, “Stick your cock in that lovely cunt of hers. I’ll be right behind reaming Cindy’s ass.”

He finished first but that didn’t mean soon. I liked the sensation of Tom’s pulsing cock through the thin membrane pouring torrents of his love juices into his wife’s cunt. I filled her bowels a short time later. That was all of our exploits until morning when Cindy and I woke up first. We screwed on the floor while her husband slept.

Eventually, her moans and loud gasps woke Tom up. He watched indifferently at his wife’s legs high over my head and me pounding into her pussy. His expression was as if he saw nothing more than watching her get ready for church. Then he left to take a shower.

While leaving the hotel, Tom said he had never slept so well. “I haven’t had a night’s sleep like this in ages. We have to do this more often.”

That’s the way it went until I met a woman by the name of Kathy several months later. She was a liberal-minded lady who was excited about joining Tom and Cindy in a foursome. One thing led to another, and we all joined a swingers’ club on the near north side of the city. I was never lonely again.

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Updated: July 31, 2021 — 3:14 pm
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