Another installment of the The Man I’ll Never Have. [m+f]

I never used to care what I wore to the office. I wasn’t the dress or skirt type of woman, no matter how many compliments or lingering looks I received when wearing one. Dressing up for work meant a sharp pair of black slacks and “Come fuck me” pumps that were at least half hidden beneath them and matching bra and panties. Sophisticated, yet sexy. I started wearing skirts and dresses as a matter of practicality. It gets hot down here and I needed to be up and walking around, impressing potential employees and business partners.

My former boss would openly compliment me on the more sexy numbers. I knew his wife and that his marriage was bliss, so I laughed and blushed and accepted the compliments. He was a wonderful man, and I felt safe around him, even if he was being a bit lecherous. Another boss within this branch of the company told me I needed to use my assets. She took me shopping and bought anything I showed an interest in. I could not believe my luck, as I was used to hunting through clearance racks and turning down a $10 pair of jeans as “too expensive.” Here she was, buying me hundreds of dollars in nice clothing. I felt powerful in these clothes. I knew that wearing them made men, and some women, turn their head.

My 51 year old wife

and I met Craig on a swingers site in Brisbane. He was doing a course in massage. J loves a good massage. I love watching her get touched. The price was her to suck him and she was so ok with that. (We both get off on her being shared. But only me penetrating her. I have never know a girl to love sucking cock as much as her. Btw. We are both in our early 50s.. sorry you young dudes! Older people have fun too!) We arrived at Craigs unit and after some very forgettable small talk, J got naked and lay face down on his massage table. Craig warmed his hands and applied oil and started to massage her upper back. He was wearing just track suit pants and a t shirt. I said that he looked a little overdressed. J turned her head and agreed. He then took the shirt and pants off. I sat back on the couch and did the same. He continued to massage her back and then started on her buttocks and legs. I could see his cock stiffening.
J automatically opened her legs a little wider. I asked if I could help. He showed me the best way to massage a naked girls buttocks! Lol. I noticed that one finger seemed to touch her from the front of her pussy. And J gasped everytime. I asked him to show me a few times. And then J said.." omg! You guys need towels here. Stop or .. omg. Please don't stop " (J squirts so hard) Craig went to the front of the table and started to massage her shoulders. I was massaging her legs. I could see her dripping. She lifted her head and saw Craigs cock . Rock hard. And just slid out her tongue and licked it. I swear. I almost came. She then opened her mouth and sucked that cock into her . Look. I cannot explain how hot it was to see my wife naked on a table with a hard cock in her mouth. I was still massaging her legs and watched her cum so hard. No touching. Just from sucking his cock. We had an awesome night. And no. He didn't fuck her. He just got head all evening. I came 3 times. Him twice. J was in a constant orgasm. Soaked 3 towels. Love my girl. … And yes guys! See our pics. There is life after 50! Lol

A young, 18 year-old (m)an and his 51 year old, pot-growing, hippy ex-girl(f)fiend

Central Coast, California, Sept. 2012

I had just graduated high school that May at 17 years-old. I was city boy based in Chicago, and was suffering a broken heart. I was in search of something, a cognitive shift, perhaps. So that June I bought a one way ticket to NorCal where I fell in love with the state. The traveling itself was an amazing experience; I saw my first weed farm, I was offered to do porn in San Francisco, I dropped LSD in Las Vegas, and enjoyed the fresh Colorado air. I came back to Chicago, had my 18th birthday and decided I would move back.

I did what any 18-year old would do – get a job. My friend offered me a job at a burger joint his old man owned, and gladly accepted. They were greeks, and I, being an American born to pure-bred Russians, we shared one and only one thing in common: fucking women, and talking about fucking women. Within the first few minutes of my first shift, my friends father, Cris, asked me:

"You ever fuck a chick in the ass?"

To which I responded,

35F/34M/34ish?F A set up story for tonight. I’m meeting a girl for a strange night of fun.

Haley and I have been a little more open with our more understanding friends about being poly and having fwbs recently. Most of them either had some idea already or after the shock mentioned it was very like us. They have immediately accepted Ian as Haleys boyfriend (after making sure I was totally good with it). We were talking to one friend Lisa when she reacted in a completely different way.

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Lisa: Lucky bitch you have two hotties in your bed and I can't even handle one. (I'm still smiling at being called a hottie).

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Haley: You'll get one soon babe just be brave and don't forget to flirt.

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Lisa: It's not that. My pelvis thing means sex is sorta off the table. When I get close to orgasm and everything tenses it gets really uncomfortable. I either have to rush to orgasm or stop. No guy is going to want that and it's not something I want to screen at the dating stage. Dating with a crutch is bad enough.

.

Friends With Benefits [MF][cheating]

“Hey Sarah,” a voice called warmly from behind her. Straightening up from saying good-bye to her child at the doorway to his class, Sarah turned and smiled at Tim. “Hey Tim; how’s it going?” “Not bad. Mostly just bored these days. Any chance I could convince you to come get coffee and help me procrastinate on work?” Tim was a work-from-home single dad, and made his own hours. “Sure; meet you at the place around the corner?”

Sarah arrived before Tim, and placed her order at the counter. She paid and turned around to see Tim walking in. Tim was one of the new trend of “cool dads.” His hair was cropped short all around, except the top where it was a little longer, and fell to the side. He wore board shorts and converse sneakers everywhere, and always seemed to be sporting a graphics tee with some geeky reference. He had deep brown eyes under his light brown hair, and just enough facial hair to look like a Hot Dad and not a grizzly bear. He smiled when he spotted Sarah, and she was surprised by the warmth she felt in her stomach.

Not over yet (affair, M/F, long)

The Woman was tall, muscular, willowy, and beautiful. From the first time we talked there was something between us. She looked at me intently and asked me questions, and I asked her questions back. (We always seem more interested in asking each other questions than answering them ourselves.) Husband and Wife were in the room, too, and oblivious to any sparks.

We live in two nearby cities, and met through old friends. I travel for business, and on a whim one day asked her to meet me for coffee when I was between meetings in her town. She picked me up and we walked in the park. I hadn't really thought about sex with her before that day, but suddenly I felt there was a magnetic field that was between and around us. The pull was stronger than I had ever felt with another comparatively strange woman before. To my astonishment, when I put my arm around her, she didn’t object. I then held her hand in the car, and stole a kiss from her lips when we parted. I was in a haze of desire. The next time I fucked Wife I was frenzied and furious. Wife loved it.

Met a woman at her hotel. Her husband called during sex, and she answered it… [M/F] [Photos]

Hi GoneWildStories! I once had the top post on this sub. I've also had some popular posts on gonewild. Here's one picture album. Anyway, I figured I'd write this story while it's still fresh in my mind!

So, I'm on some adult sites. A couple days ago, I checked my email, and had a new message:

I'm looking for some fun! In [town] tonight and Wednesday night and looking for a good fuck ;) let me know if you want to go swimming?

I've never done that before. I've met people, sure, but never just a one-nighter from someone visiting out of town. Sounds risky. I replied, but was unsure if I would go through with it. I got back:

I'm looking for a NSA good hard fuck to be honest! I'm [description]! I'm clean and DDF! Staying at a locate hotel in [town]! Here are a few pics if you want to play:

She also offered to go down on my cock, lick my balls, let me cum in her pussy, and fuck her ass, and just about any other "kinky" thing. Oh, and apparently she was a squirter. "If you hit the right spot I will cum all over you!" And she told me that just thinking about my dick was making her wet.

Fantasy Fulfilled [group of M w/F]

From almost exactly two years ago. Husband wrote his side of the story (below), I still haven't gotten around to writing my side!

Not the best writing, but writing reality is hard!

Fantasy Fulfilled

It was a cooler Saturday in September, as the desert summer was finally giving way to fall in Las Vegas. We went to a lifestyle-friendly afternoon pool party that included many other middle-aged people like us, some of which we had met before — I suppose you could call them friends really.

It was BYOB, the pool and hot tubs were warm, as were the people. The booze was flowing, bunches of naked and semi-naked people having a good time, and occasionally having an even better time in and around the pool.

We had a great time for the day, but over time all of our booze mysteriously disappeared. (Mysteriously disappeared into our mouths, that is!) Needless to say, I was pretty loose and happy the whole day; the wife even more so! I’m pretty sure she made a few new friends in the pool. After several hours at the party, we made our way at home.

Watching my wife part 1

He never thought this day would come, but here he was sitting in a chair in his bedroom watching his wife fuck a stranger, two strangers to be exact. This had all started a couple of months ago when they had discussed sex fantasies. He had told her that he had always wanted to see her have sex with someone else, this had shocked her. She couldn't understand why anyone would want to watch their spouse have sex with someone else.

They had each promised that night to be 100% open and not to get upset about anything the other said, so she admitted that she had always wanted to have sex with two guys at once. This surprised him because while she was always very good in bed she was fairly conservative in her attitudes toward sex.

"So is it something you would ever actually do"? He asked.

"I don't know, not if it would hurt our relationship".

"Well it's always been my fantasy to watch you with one guy, two would be even hotter. Let's leave it open and if you come across two guys you like then let's go for it."

[MF][oral][cuck]

Sarah chewed her bottom lip nervously, as she checked her reflection in her visor mirror one last time. She couldn’t settle the butterflies in her stomach. They had only met the one time, to discuss likes and dislikes, wants and limits, but agreed there was an interest they both wanted to pursue. Hank was married and had a family, like Sarah, but his work schedule was so erratic, it hadn’t been an issue at all to just tell his wife he had to stay late for work. Sarah had claimed she was going out for drinks with an old girlfriend from college. She had never been so glad to have him uninterested in her social circle, as he took her word and asked no further questions.

It was exactly the arranged meeting time, so Sarah took a deep breath, and stepped out of her car. As she was closing the door, she saw Hank opening the door to the building where he worked. “Sarah, I’m so glad you didn’t get cold feet.” There wasn’t a part of her cold. She pulled her corset straight under her dress, and tried to not notice how her freshly wax pussy felt practically dripping arousal. She was glad she skipped panties; they would have been ruined.