Helen in High Heels Part II [MF] [Long]

Helen and I met every Monday that semester. We studied some. But it was mostly just talking. She shared her notes with me and I did well in the class overall but we had grown much closer by the end. We talked about everything: politics, religion, friends. She told me about herself. She was the oldest of 4 children. Her mother died when she was young and she raised her younger siblings. Her job, social work, wasn’t really her passion but it was an easy career that she could pursue while commuting to school and caring for her siblings. She missed out on fully enjoying her college years and her 20s. She had to be an adult and a mother too early. Soon after, she met Jack. She was 29 to be exact, and married him soon after. He was older so they had 2 kids right away, now 4 and 2. Once Jack moved up in his job she had realized that she didn’t like her job so she cut back to part time and decided to go back to school and take some classes. She had money so she was able to slowly take one class at a time. Her ultimate goal was to apply to medical school, dental school or even nursing. But she was slowly realizing that she might not have time. She was 35 now and she would need 21 more credits before she can apply. I asked her how she plans on going through medical school with 2 young kids. She didn’t really have an answer to that. She said she was taking it one class at a time.

The Panty Dare [F]

Rose is a great kid, and by kid of course I mean someone who also remembers the Nixon administration. She is divorced, raising a son, and works as a financial assistant for a Bay Area firm.

I met Rose on Tinder a month or so back, and we quickly hit it off. I always know I’m going to like a woman when I tell her I’m married and playing with permission, and I don’t get the door slammed in my face. If memory serves, the conversation went like this:

Me: “Let me give you a key piece of information. I’m in an open marriage, with permission to play, and I am here looking for FWBs. Let me know if that’s something you would be at all interested in.”

Rose: “It intrigues me – would your wife or other FWBs be involved?”

That’s my kind of response. (And that actually was her verbatim reply; I just now scrolled through my Tinder feed to check.)

Needless to say the conversation went interesting places from there. Likes, dislikes, fantasies, desires, and of course the inevitable arranging to get a drink. We picked a time and place for the following week, and she did some dress shopping in the meantime. She found something perfect – short and slinky, showing plenty of cleavage. I was well impressed.

(MFF) finding out just how close wife and sister in law are Part [3] [long]

Part [3]

All was clear, and I couldn’t hold back any longer. My dick was being wrapped around by her warm wet lips. I felt like giving her the full load of cum that I had built up throughout the day. She was pushing her ass hard into my lap, and my dick was sliding back and forth between her lips as she let out a little moan. She led forward and grabbed the side of the pool as she stood up and pushed her ass hard into my throbbing dick as the small of her back crested the water.

As I grab her hip and hold her back from pushing into me again as the head of my dick was at the opening of her dripping pussy. I wanted to tease her with the tip and went slow, so I did hurt her. As she looks over her shoulder to see why I am holding her back, she says, “don’t worry, I’m not a virgin” and gives me an evil little smile. This comment takes me entirely of the guard, and she begins to wiggle her ass at me with my oozing tip resting just inside her tight lips. I gently pushed forward until my pulsating cock squeezed her opening, and I felt her pussy wrap tightly around my dick as she let out a little gasp. I had to pause as not to explode that very second. She was by far the tightest that I ever had and if it was real and she was not a virgin she had not been with many people. She whispers “more, please more” as her body becomes tense and her head rears back.

Sister-In-Law [MFF]

For as long as my wife Stephanie and I have been married (12 years now), her sister Janice and I have been flirting. Don’t get me wrong, it’s all very innocent; a longer-than-normal touch as we pass something across the table, a slight foot brush underneath said table. I like to give her a hard time (no pun intended) and she likes to pretend that she disapproves of me. When in reality, the whole family, including her, knows that I’m ten times better than the doucebag John that she married. While I get the feeling that she would let the flirting progress, I would never actually cheat on my wife.

Well we planned a trip, just the four of us, to the mountains for a week. It was supposed to be a chance for each couple to spend some time together, unwind a little, and maybe for the sisters to do a little shopping. I was looking forward to spending a lot of time alone with my wife, and saw the tagging along of the sister-in-law and her husband as an unavoidable annoyance. At least they would be in their own room. Or so I thought…

OC True [MF] what happened after a neighborhood summer night party.

Reposted from several months ago, I cleared my history after thinking that someone close to this story had figured it out…

So to set this up, my wife and I were pretty good friends with some neighbors, several times over the summer we had some late night parties at our place that often involved a little too much alcohol and sometimes the flirty fun had pretty suggestive content.

One of these nights, quite unexpectedly, it just happened to go a lot further. We had been drinking more than usual and the other guy had already gone home so it was just the three of us. It was getting really late so I decided to go to bed leaving the girls to chat.

Not too much later I felt someone slip into bed and didn’t really think much of it, until I felt a hand on my penis and heard a light giggle that wasn’t my wife. My wife was asleep in the living room and my neighbor came to bed!

It started slow with some kissing and some touching, omg did she feel good. The touches became more intimate and the next thing I knew was that she was giving me a blowjob while my fingers circled her soaking wet clit.

Another story from my clinic [MF]

I’ve posted a few stories here before, here are links.

[https://www.reddit.com/r/gonewildstories/comments/aam4yk/what_an_amazing_day_at_the_office_mf/](https://www.reddit.com/r/gonewildstories/comments/aam4yk/what_an_amazing_day_at_the_office_mf/)

[https://www.reddit.com/r/gonewildstories/comments/bqk4y9/another_great_day_at_the_office_mf/](https://www.reddit.com/r/gonewildstories/comments/bqk4y9/another_great_day_at_the_office_mf/)

This one describes another encounter in my clinic.

My clinic is in a 3 story office building. I’ve described that I’m happily married but my wife has health issues that preclude a regular, vigorous sex life. But when we do have sex, it’s good. There’s something special about making love with someone you genuinely love. But, there’s also something special about fucking a dirty little slut who wants to be your fucktoy. Just different pleasures and I greatly enjoy both.

There is a hispanic woman who is on the janitorial service. I think her shift is something like noon to 8. Her name is Margarite. I’m guessing she’s late 30s, early 40s. I’ve spoken with her a few times, she’s a nice lady, never remotely had a sexual thought about her, though my sense is she’s interested. Could be reality, or just my delusional male ego talking. She’s reasonably attractive but could stand to lose about 10-20 pounds. Not particularly athletic looking, which is really my type. But medium breasts, reasonably firm, and a decent ass. Trust me, there’s a reason I’m sharing this. I’ll be circling back to her in this story.

After almost a year of experimenting with hotwife/sharing, the story of the first time my Japanese ex-wife and I had a full-on threesome [MF][MFM]

So, I previously shared the story of the first time my ex-wife and I experimented with sharing:
https://old.reddit.com/r/gonewildstories/comments/badf0f/the_first_time_my_japanese_exwife_and_i_branched/

As you can gather from how much we enjoyed it, we did not stop there. Still, for almost a year, it was always her having sex with another man privately, and me just hearing about it and seeing pics afterward. Finally, on a trip back to the US, I ended up sharing her with another old friend of mine who was completely up for doing stuff with all of us there in the room together.

For me, it was brain-meltingly hot, and like the last story, it was another major line crossed in exploring that side of sex.

Obviously it wasn’t a spontaneous thing. He had heard the stories from my other friend, and we’d talked about the idea of passing her around the group in the leadup to that visit home.

By that point we’d been there for probably a little over a week, and she’d already been with with my other friend (the one who had visited Japan and fucked her) and two other friends of mine who’d been asking for a turn with her for months, continually checking when we were going to visit.

Be[F]ore I [M]arried my Catholic School girl, we had an epic First time Overnight weekend.

Last night’s hot experience with my wife inspired me to write about another gonewild moment between us. I’ve wrote about our encounters on several occasions but I’ll quickly recap. Chelsea is the living embodiment of the Catholic School girl stereotype. Grew up in a repressed home, spanked constantly as a child all the way to HS (and grew to love it as a fetish). Remained a “virgin” all through her teenage years by giving regular blowjobs and having anal sex with her b/f. You name the repressed fetish, she pretty much had it. Because of her ultra-religious family and strict adherence to proper etiquette in society, Chelsea wore a “good girl” mask nearly 24/7. It was when she was alone and with me, did she finally get to show her true self.

A family vacation thank you [MF]

First off, let me start of by saying that the when you walked into the restaurant I fell in love with those tits. The heat in Rome was obscene. Everyone was dressed down to survive and your low cut top that must have skirted your areola left little to the imagination and despite your best attempts to cover them, your rock hard nipples when you sat under the aircon vent could have been used to dial a phone.

I think I got away with staring; your husband was arguing with your kids too much to notice me and my wife had her head in the wine list. Luckily our accents gave us away as fellow countrymen and even luckier that your spouses worked in the same industry, otherwise we’d never have started talking and they’d never have been so engrossed in shop talk to see us flirt. Of course I say flirt but we’d both been so long in our relationships that longer than average eye contact constituted a hot connection for both of us.

I Can Tell

The history behind his eyes, tells me a lot. Long nights waiting for her left him lifeless till the morning. Each day she would charge him up, by sucking his cock like nothing is new. He laid into her desire knowing something is different. Her nude body would lay bare next to his after a lustful night, usually. However those nights are gone as she never comes home anymore. Sweet milk chocolates on the kitchen counter brought wide smiles to innocent lips, usually. However cold dinners persevere themselves as full bellies are hidden from wondering eyes. No dinner yet juicy pussy would take the place but not today. A realization came quick when something new paid attention. So he took refuge in the pussy of Erica. As Lola gave comfort, she bent over letting him unleash his pain. Debbie welcomed his emotion as sticky cum smothered her lips. After all was done, he woke up to a wife he knew but didn’t want anymore.-liviaflair