A Not-Quite Office Encounter Turns Into a Tryst [M] With a Much Younger Woman [F]

As I wrote in my last post, a few years before craigslist shut down its personals sections, I had within a short period of time three NSA hook-ups with younger women  … much younger. I was in my early 60s and all three of them were in their 20s. This first young lady, the one I wrote about most recently, answered an ad I placed on cragislist looking for an office blowjob, but the second one — the one I want to talk about now now — placed her own ad. And of course I answered.

I work in an office not far away from a major university in a major Texas city. My work affords me a very flexible schedule, as it involves in-person meetings at various times of the day and sometimes into the evening and weekends, or at least it did pre-COVID. So if I have someone(s) over for a meeting in my private office, or if I head out at any time for a meeting, no one questions it. I do work closely with my office colleagues, but my supervisors are all in other states, and I have enormous flexibility in structuring my work week — as long as I get done what needs to get done.

Sinnndy Meets an Older Man [FM]

**Hi, my name is Sinnndy. Some of you have read stories about my sexcapades, but I haven’t told you information about myself. At the time of this story, I was 18 years old, 5-3 just under 100 pounds, 34B-24-34, shoulder length brown hair, and I have been told I am very attractive and that I have a great ass.**

**Don’t let the fact that I was 18 let you think I was inexperienced, because that’s just not true. I have probably tried more different and kinky things than even my mother has. I was born and grew up in a northern suburb of Chicago. I love it here, and plan to never leave.**

**I have great parents, I love them both, and I have a great brother, 5 years older than me. He lives in Chicago. We were brought up in a nudist household, when no one else was around; we would walk around the house naked, that’s why I am not ashamed of my body. America is way too uptight about nudity. During the summertime, I lay out in my backyard nude. I know the neighborhood boys, and men, love me.**

Welcome to the Neighborhood

We are out walking the dogs on a warm summer evening in late June. It’s been an exhausting work week for us both but even though you fucked me passionately this very morning before breakfast, I am so hungry for you. Back to back meetings thwarted my plans for an afternoon quickie but now that it’s evening, I’m craving our connection. You were flirty with me before we left for the walk and I know that you are in a sexy frame of mind as well.

As we pass through the adjacent neighborhood, we notice that folks are outside socializing….from a distance, of course. A really cute and friendly lab runs up to play and we meet his owner. She’s an older woman who engages me in conversation. You are playing with the dogs and having a little fun. You look HOT in your white tee shirt and dark shorts. I am already anticipating jumping you as soon as we have some privacy later.

We should grab a drink tonight [MF]

In 2014 I was traveling quite a bit from the East Coast to California for business trips. My marriage was going through a rocky patch, and I was usually making some questionable decisions while traveling, meanwhile calling myself “separated” while I was in another timezone. Shady, yup, I know.

I’m a decent enough looking guy, pretty short though, 5’8 and very fit, a thick 8″ cock (post history if that’s your thing) and with my long hair it’s pretty obvious to most people that I’m a surfer. If you dropped me in a bar in Baltimore, I’d be a god, but in California I tend to blend in a little.

One particular trip, I was eating breakfast in the hotel patio when a gorgeous woman came floating through the breakfast buffet line. She was short and thin, about 5’2 with long dark hair, and a tan complexion. Truthfully I couldn’t take my eyes off of her, as she looked amazing in her yoga pants and flowing t shirt. If I had to compare her to a celeb, I’d say Evangeline Lily, with a smile more like Carly Simon.

Cumming on Mary’s BFF’s DDDs [MF]

Some of y’all followed along with the [stories of Mary](https://www.reddit.com/r/gonewildstories/comments/ipatp1/freak_show_marys_final_act_blowjob_carnival/) (18), a girl from ages ago in my (20) life who gave me an incredible birthday present. In the [Pie-in-the-Face story](https://www.reddit.com/r/gonewildstories/comments/ig6kip/marys_week_of_cumswallowing_2_blowjob_carnival/) from this, I alluded to Mary’s friend Jessica (19) who pointed out that I had left some cum on Mary’s neck and that she probably guessed it because, well, I had cum on Jess at one point, too. So I thought I’d share that story.

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Mary and Jess were BFFs and had been for years since they grew up together. While Mary was Miss Popular, Jess was the quiet, studious type. She was obsessed with Jane Austen and fancied her boyfriend a Mr. Darcy. She was a musician, playing some sort of string instrument. I was a kinda chubby, brainy nerd, eventual honors grad who yet somehow managed to be reasonably popular and well-liked. Frankly, Jess and I were fast friends, even having our own two-person book club at one point.

My Sexy Dirty Ex-Wife [MF] [Swing]

My ex-wife, Julianne (not her real name) and I had dated for nearly 2 years before we decided to move in together We live together for about a year before we got married and we were married for about 2 years at the time of this story.

Julianne had the girl next door look. She was taller about 5’8″ to 5’9″, long ass legs, dark almost dusky skin, dark brown hair, big brown eyes. Her tits were large and her ass was tremendous. She was very gregarious especially when she was drinking. Our sex life was very good at the beginning however after a time things were getting a little mundane.
To break the monotony during sex we started discussing our fantasies. I told her that I had a voyeuristic side and I’ve had it for a long time, she was very intrigued, because she was a bit of a exhibitionist. We shared quite a few secret fantasies over the coming months, to put it bluntly, her kinky matched my kinky!

One of my favorite things was watching her troll on our
social media account to attract single or married men, to message, flirt, and share nude pics. We broached the idea of swinging, however our professions were very public, and we didn’t want to risk our jobs.

Role-play Gonewild. Girl[f]riend gets [m]ore than she could wish for!

My first [STORY](https://www.reddit.com/r/gonewildstories/comments/bkl0tg/wellness_centre_gonewild_girlfriend_gets_more/) which was well received, thanks for that!

Firstly, just some background information about who we are. We fell in love with each other as very young and inexperienced teenagers. Now in our early twenties, we are physically at our peak, she’s a pretty blonde with average sized breasts but extremely firm and perky with puffy nipples of the perfect shade of pink. Slim body but with the right curves and amazing round ass! Always completely shaven, with curious labia slightly sticking out.
He has a handsome face, with a toned, athletic body type and an average sized penis which is always ready to go!

Because we met when we were very young and, as said above, inexperienced, we had to find our way ourselves but together. Both openminded and with a willingness to try new stuff, we gained a lot of experience like e.g. FMF-threesomes. Different kinds of roleplay were also something she liked, in particular her being the client and I had to be the naughty massage therapist. But also, the harder stuff would get her going, for instance rape-play was something she was craving every now and then. The idea of being forced, feeling powerless and dominated for a stranger’s pleasure.

East Flying West Chapter 2 [AMWF / AMXF]

Chapter 1 can be found [here](https://www.reddit.com/user/AzianKing/comments/ilfs01/east_flying_west_ch1_long_story/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

**East Flying West Chapter 2**

Zoe asked Ryan just about his opinion on white girls. Ryan didn’t want to say anything weird so he responded by saying that he thinks they are fine. She didn’t ask any follow-up questions about it, which Ryan appreciated.

It was going to be a long flight, about 13 hours to get from Hong Kong to London. Ryan and Zoe both prepared well for the flight. He listened to music, read some books about the UK and talked more with Zoe. Zoe suggested to watch a movie together, so they did before taking a nap on the flight. As Ryan woke up he was just 2 hours away from London. He went to the toilet and looked around as he walked, he would say that most of the flight was Chinese with quite a few young people possibly going abroad for studies. After he sat back down a flight attendant came by with food.

Normal Date Night Ends Up With Getting Laid at Church [MF]

For the most part, my wife and I have a fairly vanilla sex life, but every once in a while she throws me a curve ball, and this story is definitely one of those times. A little back story, my wife and I have been married nearly 2 decades and have multiple kids together. Part of the lack of sex in our marriage has to do with the kids, it’s sometimes hard to find that private time with the kids at home. When they were a little younger, we used to be able to go on date nights and leave the kids home and they’d go to bed by the time we returned and we could have some post date fun. However, as they’ve gotten older and are staying up later, now we return from a date night to find a house still awake, which isn’t great for ending a date with a bang. Also worth noting for the context of this story, my wife and I are both active in our church, and as a result some of the teams that we serve on, we have access to get into the building. Enough build up, let’s move on to the story…

My First Visit to a Glory Hole [MF]

More than a few years ago, I answered a craigslist ad from an escort that was offering a gloryhole service at a good price. I’m naturally on the cheap side, although I prefer the term “frugal”, and this extended to paying for sex. The ad said that she would have a glory hole curtain set up, with a willing participant behind the curtain. The host (who placed the ad) would be on the outside with the customer to manage the experience. 

For those unfamiliar with the term “glory hole”, it refers to a man sticking his dick through a hole so that an unknown and unseen person can service him. Usually this refers to oral sex, but it can also mean intercourse. 

Back to the story.. I arrived at the address I was given, it was surprisingly in a quiet suburban neighborhood in NE Austin. If the neighbors only knew what was going on in that house! Lori answered the door wearing a robe. I’d describe her as more than cute, maybe pretty when she was dressed up. Probably 5’5”, long brunette hair (I have a thing for brunettes), moderately sized boobs (I’d guess a b cup but I’m a guy… we really don’t know these things!), thick thighs like she used to be a gymnast, nice firm ass, and a sexy smile that instantly made you feel welcome.