headstrongcocksure, Author at NSFW story — Page 3 of 4

Craigslist Success: The Married Teacher [MF]

This happened about 7 years ago, and while not the first time crossing the lines physically outside of my marriage, it was the first time I had sex with a woman other than my wife. To make sure this point is clear, I lost my virginity to my wife while we were dating and then went on to marry her. So up until this story, she was the only woman I’d ever had sex with.

I had been toying with the idea of finding a friend with benefits for a while, and had met up with a few women here and there, but none of them seemed to be what I was really looking for, and aside from some make out sessions, fingering, and blow jobs I was still looking for someone. I ended up posting an ad on Craigslist and I was brutally honest with where I was. I indicated I was married, and tired of being alone. Read more »

Craigslist Success: The Panty Selling Couple [MMF]

I’ve shared in previous stories that I have a used panty fetish. I love getting a pair of used panties from a woman, but with being married, this isn’t something where I can just jump on the panty selling reddits and select from the menu and have them delivered to my door. So I attempt to find local women, willing to sell me their panties. This story took place roughly 5 years ago. I had posted my normal ad on Craigslist looking for local women willing to sell me their panties.

I got a reply that kind of intrigued me. It was from a guy named Tom offering to sell his wife Cindy’s panties to me. Now normally I wouldn’t go for this, because I want to interact and buy directly from the woman. I don’t have a problem with her being married, but I do want to make sure that she’s consenting to me having her panties, and of course I want the panties to be worn to our meet up and taken off during our time together. Read more »

Wendy Dripping Cum in the Parking Lot [MF]

I’ve been asked to post some of my other stories with Wendy, so here’s one that stands out in my mind. This happened around 7 years ago, during the first round of hooking up with Wendy. She and I frequently met up and just drove around, chatting, playing games on our phones, and finding places to have sex.

We had driven just out of town to a place where the city was building a new community center, park, and sports fields. The whole place was under construction, but the massive parking lots were completed. There wasn’t really anyone else out there, except for the occasion cop that rolled through on patrol. We had gotten out of the car walking around and checking out some of the new stuff that was being built. Wendy was wearing a dress, which was pretty common for when we would hang out. Read more »

Putting on the Brakes [MF]

This happened around 7 years ago. I was just venturing out and starting to look for a FWB to deal with a mostly dead bedroom. I’d placed an ad on Craigslist stating honestly my situation and what I was looking for. I suppose the ad was good, because I actually got a small handful of legitimate responses from the ad from various women in the area who were interested in chatting and seeing if maybe we could work something out. Kassy was one of the replies I got. She told me she was married, no kids, and her husband was a truck driver and gone during the week and only home on weekends. I don’t believe he knew she was seeing other men while he was out of town, but she was pretty open that she wasn’t really looking for just a one time thing, but rather she wanted a boyfriend while her husband was out of town. Read more »

My First Time Cheating [MF]

I don’t really remember exactly when this happened or how old either of us were at the time. I do remember the night, but not all of the details leading up to it.

I know I had posted an ad on Craigslist, probably just looking for local women to chat with. Heck, I may have even responded to an ad. During that time, I found a fair amount of success using the “Strictly Platonic” section just looking for chat friends. It seemed a lot of women would post and respond there because it wasn’t explicitly looking for sexual connections.

Anyhow…I had started chatting with a woman and Celia. She lived maybe 30 minutes from me and we hit it off pretty quick. It all started out fairly normal, but after a while the topic of sex came up and we began discussing likes and dislikes and starting to talk explicitly about what we could do together. Read more »

Her Kid is Watching TV, Her Boyfriend on His Way Home, and She’s Bouncing On My Cock in the Alley Behind Her House [MF]

This isn’t the first story involving Wendy, but I wanted to share it as well. If you’d like to read some of my other stories about her you can follow the link below. These aren’t in chronological order, nor do they build off of each other.

[https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/](https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/)

Wendy and I weren’t really what I’d call “regular” friends with benefits. It seems like it would be a few months between hooking up, and trying to get the scheduled always seemed to be a chore. She was busy, I was busy, her boyfriend would change plans, her kid was sick, etc. We had been chatting and talking about when we could hook up sometime, and we hatched a plan. Her house was a few miles off the route I took to work, and so our plan was I would swing by her place on my way to work, after her boyfriend had left and we’d fool around in the car before she took her kid to daycare.

Well, as luck would have it, I’m on my way in to work, and she texts me that her boyfriend decided to work from home for the morning, and we had to scratch our plans. I was disappointed, but it was pretty par for the course. Read more »

Clone-A-Willy for a Former FWB [MF]

Several years back I had a FWB, we’ll call her Wendy. We spent about 2-3 month hooking up somewhat regularly, as regularly as a married guy could find excuses to get out of the house. Our hook ups ended suddenly when my wife questioned if there was another woman, and I told her yes. Long story for another day.

Fast forward 5 years and I hadn’t spoke to Wendy since I ended things. We didn’t live in the same town but a few towns apart, one day, on my way to work I believe I spotted Wendy on the highway. That got my mind rolling again and I decided to break the 5 years of silence and reach out to see how she’d been. I’ll admit, during those 5 years I had tried to be a faithful husband, but there were times I failed and I was actively thinking about trying to find a new FWB, and thought that maybe she and I could pick up where we left off. Read more »

Craigslist Success: The Panty Upseller [MF]

I’ve shared this story a few years back on a different account, but it’s since been deleted, both the story and the account so thought I’d share it again.

I have a used panty fetish and love getting my hands on a pair of panties from someone local from time to time. I know I can buy online ( r/usedpanties ) but with being married, I can’t have them shipped to my house, and I don’t want to spend money I could be spending on panties, on a PO Box. So, I would attempt to find women in my local area who would be willing to sell in person.

I’d usually do this by posting an ad on Craigslist in the Casual Encounters section indicating that I was interested in buying panties, and to contact me if you wanted more details. Most of my ads were place in the Kansas City area (if you’re near KC and interested shoot me a DM) and I’d get a small handful of replies. Some would materialize, others wouldn’t. When I find a woman I like buying from, normally it’s not just a one time thing, but I’ll buy from them multiple times if they’re willing. Read more »

Reddit Success: A Cum Slut in the Real World [MF]

This story is a follow up to a previous story I posted 5 days ago. I wrote this story specifically after chatting with a new follower and briefly having told her about this previous encounter.

Craigslist Success: Watching Me Stroke [MF] from gonewildstories

When I wrote the story she and I were discussing a meet up with her and indicated I was hoping I’d have a new story to share in the coming weeks. Well today is that day.

As I’m thinking through the details I find myself in disbelief that this actually happened as many of the details of this story are things that would make me suspect the validity of a story, but I assure you it’s true.

5 days ago I got a notice from Reddit that I had a new follower. I clicked on their profile and sent them a message thanking them for following me. I also noticed that their profile had a number of photos of her as well as some various stories that she’d shared. A few moments later she responded telling me she enjoyed my stories and was glad to find another kinky person in Kansas. Read more »