Sex and the Windy City

Big Dicks

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.”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 güvenilir bahis 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.”“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.”“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 güvenilir bahis siteleri have it! Do you think it’s too skimpy for Chicagoan’s sensibilities?”“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.”“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.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 iddaa siteleri 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.“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.”“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.”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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