Author: UpbeatOpportunity

Accomplishing a feat I never set out to tackle: Sleeping with three sisters and their mother over the course of nine years [MF] [NOTE: Long story]

Sometimes, sexual feats fall right into your lap without much of an effort. Such was the case when I slept with my high school ex-girlfriends’ mom last week, months after her divorce was finalized.

First, a timeline.

Shortly after my 18th birthday, I began having sex with my then girlfriend, Katie. Katie was a bit on the larger side compared to me, a thin cross country and track athlete at the time. We were sexually active through most of our senior years, and went our separate ways in college.

My sophomore year, I hooked up with Katie’s younger sister, Abby, an incoming freshman. We dated on and off for a year or so, breaking up only to get back together on the weekends here and there.

It wasn’t until 8 years later I hooked up with their youngest sister, Cassie. Now a sophomore in college and nearly 7 years younger than I, Cassie caught my attention on Tinder when she was home for winter break. We messaged back and forth and talked about my time with her sisters before leading me on to a couple of one night stands when she was home. She ended up virtually ghosting me when she went back to college. Read more »

Wife sets up couples swinger party for anniversary [MF][MF][MF][Warning: Long story]

So, first, some background. My wife and I have known each other for 7 years. We’ve been dating for 5, married for 3 and have been in an open marriage/polygamous/swinging for about a year and a half now. We still have sex with each other and love each other very much. But sometimes, we desire different things from different people. If you want to learn more about that, message me. I’m always happy to share.

Last weekend was our three year anniversary. In the past, we’ve taken trips and just spent time together hanging out. With COVID-19 around, trips were out of the question. But, we had some friends coming into town, and figured that would be a fun weekend.

About a week before, my wife said she wanted to surprise me early with an anniversary gift. She hands me a folder and it’s a series of texts from her friends: Cassie and Sara and their significant others, Matt and Tom. It’s a group text about three pages long detailing my wife’s request for a couples swinging party while they’re in town. It details our relationship, where we’re coming from, our boundaries we’ve set with each other, etc. And it goes on as she convinces and educates them on what she envisions it to look like. Read more »

Breaking ethical norms for fun with an interviewee [MF]

For the last few years, I’ve been working with my local newspaper, covering random stories and events to grab a little side cash for entertainment and fun. It’s been a great time, easy, and I get to cover local sports a lot of the time. It’s a daily newspaper that publishes five times a week, so it’s pretty easy going. I’ve been doing it long enough that I usually get to pick where I go and what I cover, barring some breaking news that happens and they need all hands on deck.

Part of this has been consistent coverage of our D-III volleyball team that is in our area. Lucky for me, the sports reporter is more concerned about football, leaving this open for me to spend time getting to know players and coaches, covering games and, as the case was this weekend, travelling to a tournament.

I went down on Friday, covered their evening games that night and all day Saturday. I’ve known some players for several years, as they came up through local high schools, and on to this college. I’ve know the coach for a handful of years, and it’s seemed less and less like a job, and more of a conversation. Some athletes are friendlier than others, and I understand that. But that line was crossed and I found myself in ethical and moral trouble this weekend. Read more »

Indulging in late night lust at work, with my coworker [MF]

I’m a 26 year old single guy who works in a smaller office with 96 percent women. For those who thinks that’s awesome, it’s not. For those who think it sucks, it doesn’t. It’s great most days, and honestly, it’s rarely that noticeable. I get along great with the 15-20 people I work with, and I assume they get along with me, too.

One thing I have noticed recently, or at least now that the summer is coming around and office dress code is pretty lax, is how attractive I find some of these women who I never thought much of before. I’ve never been with anyone that much older than me, but I am one of the youngest in the office. Most of the women are between 30 or 35 and 50 or 55. I’ve usually been attracted to women more around my age, and about the same size or bigger than me.

I’m a 6-foot zip white male, blonde hair blue eyes. I’m a runner and skier, so I like to believe I’m in decent shape with a lean build. At 170 pounds, I’m certainly no walking hunk by any stretch of the imagination. When I first met Christine though, my jaw dropped. Read more »