Author: headstrongcocksure

An Interesting Switcheroo [M]

I hadn’t initially planned on telling this story here, but I read another one that sparked a recollection that I decided to share. Some friends in real like know this story, with a few details changed to protect my pride, but here’s the true story.

I work in Corporate America for a mid sized company. We rent space in an office building sharing it with other corporate tenants. Each floor of the building is pretty much laid out the same. The lobby and bathrooms are shared by all tenants of the building with only office space and break rooms being private to the tenants.

Well, I had been chatting with a woman I’d met online. She loved to tease me while I was at work. Telling me about all the dirty things she wanted to do with me. Telling me about the other guys she’s fucked sparing no details, and sending me dirty photos. Her goal was always the same, make me horny, get me hard, and get me to do something about it. Read more »

Reddit Success: The Size Queen [MF]

This happened about a year ago. I was poking around on Reddit looking for any F4M posts near me and ran across a post from a woman claiming to be a size queen searching for large cocks. On a whim I messaged her telling her I’m around 8-9 long and a 6 inch girth. We started talking and quickly realized we work in the same field, but different companies. Our chatting was full of sexual banter, picture trading, and work chatter.

She informed me about an upcoming conference related to what we do and asked if I was planning to go. I hadn’t been, but was quickly convinced that I should. I got registered and we planned to meet for the first time at the conference.

The conference was fine and over the course of the first day we got a few opportunities to chat. As the day was drawing to a close she and I got to chatting some more and decided we needed to sneak away for a bit so we left and headed to her car parked in a nearby parking garage. Once in her car we started making out and my hands were all over her body. Feeling up her breasts, and rubbing her pussy through her pants. She was rubbing my cock through my pants and eventually pulled it out to give me a blowjob. Read more »

Tinder Success: The 911 Operator [MF]

My wife and I are happily married, but polar opposites when it comes to sex drives. We’ve talked about it before, but nothing ever changes. We have sex maybe once every 1 to 2 weeks and that’s usually as result of either me finally outright asking her if we can have sex, or she picks up that I’m getting really crabby and it’s her attempt to fix that. I know it’s not right, but I’m tired of hoping for more, and being disappointed every time. So I’ve started looking elsewhere. I turned to Tinder and posted an add not too different from what I just wrote above. Indicated I was married, and looking for a fwb.

One of my matches was Carly, a 911 operator from a nearby town. We got to talking and she was in a bit of a different place in her life. She’d been married, was divorced and making up for lost time. She made it pretty clear up front that she loved sex, and she loved meeting up for that purpose. We started chatting, and soon pictures and videos were being shared both directions and lots of messages about what we’d do to each other were flowing. Read more »

Drug House Mia’s Panites [MF]

I’ve mentioned in other posts that I have a used panty fetish. I know there are tons of resources online where I could buy used panties, but since I’m married, having a woman ship her worn panties to me isn’t really an option, so I turned to Craigslist. I’d post an add stating what I was looking for, and encourage any women with interest to message me. I know that since I was offering cash, I’d get a wide array of women responding. I typically tried to sell to women who, while they wanted/needed the money, they weren’t in desperate situations. I didn’t like buying from women who saw this as their last option, but rather wanted someone who needed the cash, but was having fun in the process. Thi s story is probably one of my most questionable buys…

One response I got was from a woman named Mia. Her pictures looked pretty normal, think mid 30s single mom vibe. She wasn’t a bombshell, but didn’t look entirely like a slob either. We discussed what I was looking for and we agreed that she’d meet me while wearing the panties, and let me watch her play with herself while wearing them, and then take them off and give them to me. I don’t remember our agreed upon price, but I’m guessing we were in the neighborhood of $60. Read more »

Ally the Stripper [MF]

This story will probably be a bit on the tame side, but it’s one of my first sexual experiences post getting married. A little back story, prior to dating the woman who would eventually become my wife, I didn’t have much experience with women. I’d made out with a small handful of women, had fondled the breasts of a few, and had fingered one (funny side story, the girl I fingered was also my first kiss, which happened later – DM me for the story). Anyhow, prior to dating my future wife, I’d never had a woman touch my uncovered cock. I’d done plenty of chatting with women online, but that was pretty much it. We were also both raised religious, so pretty sheltered and naive.

So…I got married and had never been to a strip club, but absolutely loved the idea of watching a woman strip. I’d search out pictures and videos online of women stripping and dream of seeing this happen in person. Because of our religious backgrounds this would not have been acceptable, nor was the porn, or chatting, etc. Read more »

Craigslist Success: The College Girl’s Panties [MF]

I think this happened around 4 years ago, I was 36 or 37 at the time. I had (have) a used panty fetish and found myself using Craigslist to try and find local women who would be willing to sell me their panties. I often looked for local women to buy from because being married, having a pair of dirty panties mailed to the house wouldn’t really go over too well with the wife. I had posted an ad indicating a little bit about myself, my fetish, and that is anyone was interested in selling me their panties to reply. These ads usually got a small handful of replies from various women (and men) expressing an interest. The vast majority might email back and forth a few times and disappear, but occasionally one would land and I’d be able to arrange something. This is one of those stories.

I had posted the ad and got a reply from a woman named Daisy. She expressed an interest, indicating the was 18 years old and a student at the local college in town. We emailed back and forth a little bit and she shared a few photos with me. When I buy panties locally, my main goal is to get a “fresh” pair of used panties. However, I often describe what my dream scenario for the exchange is and let the woman know I’m open to whatever they’re comfortable with. So I described my dream scenario to Daisy as this: Read more »

Tinder Success: The Real Estate Agent [MF]

Earlier this year I decided to start playing around with Tinder. I didn’t really expect to have much luck with it since I’m a 40 year old married guy looking for women to fool around with, but I was pleasantly surprised with the results. Thought I’d share a few of my stories, mostly because I like to relive them, and figured this was a fun way to do so.

A little back story: at the time that this was going on, I somewhat had a FWB that I would see from time to time. Things were really spotty between the two of us, and it was really hard to work out our schedules to actually make something happen, and even when we could work out our schedules, it seems like there were always last minute things that would come up. She’d get sick or start her period, her kid would get sick, her boyfriend (yes…) would change his plans resulting in ours falling through, etc. This will be important later… Read more »