[MMF] An Unexpected Threesome (some bi and pegging, so you are aware)

TL;DR A pushing 60 widower tells you about the time I was in the worst relationship ever and during its breakdown got sucked into this threesome which, by the way, I loved. Then we broke up shortly thereafter.

Lee and I worked at the same place while I was in my later years of college. I’d like to say that she was a nice girl, but no, she was the biggest bitch I’d ever met. I took to her because she was known to fuck and as a guy who’s always been hyper sexual and open to new experiences, that’s exactly what I was looking for. Being a computer science type of nerd, no matter my looks, has been stifling to dating sometimes, well, or at least it was when I was younger. Plus I wasn’t a frat guy, so the dating pool just wasn’t built in. And I didn’t seek it out in any case. I had finally gotten into a good college and didn’t want to fuck it up… until I almost entirely did.

[MFMF][MFF] Our first swap + the morning after

TL;DR A pushing 60 widower tells you about how a pool party and cookout leads to a discussion about swapping with friends. We later enjoyed a full swap and my late wife enjoyed some time with the female in the couple as well.

TL;DR 2 This is another abnormally long story. Hope you enjoy it though!

Anna and I had always been sexually compatible. I’m a non-religious guy, but the only way I can describe our sexual chemistry is with the word “blessing.” It was a blessing that I met someone who not only was on the same page with me relationship wise, but also definitely sexually. Long before we got together she’d tell me about her sexploits, totally openly, and I didn’t find it off putting whatsoever. In fact, if anything I was intrigued and it turned me on; it’s not like she was sleeping around and hated herself for it. No, rather she was sleeping around and enjoyed almost every experience immensely. I was always one who was open to new sexual experiences, so Anna being a sexual person attracted her to me even more. She’d asked me early on if I’d mind if she slept with other guys; the cuckold thing wasn’t for me (and still isn’t) so I offered an alternative. What if we swapped with another couple or an “exclusive” group of couples? Anna was into that idea very much, but after she got pregnant and we had our first kid — the idea fell by the wayside, well, at least in the short term it did.

[MF][MFF] Fucking Young

TL;DR A pushing 60 widower tells you about the time when he not only slept with a much younger woman but also enjoyed a spur of the moment threesome with her female roommate.

Disclaimer: This story, while completely true, is over the top and I can’t apologize for it. I’m just telling a story is all. Also this story is LONG. I hope you enjoy a wasted day at work as much as I’ve spent a vacation day from my end of things writing it. I’ll be retired soon and can write more of this trash over time. *bwahahaha*

This long-ass story all happened just over 20 years ago and was pretty much a summer romance, but who’s kidding who? Lots and lots of fucking was the order of business, and I wouldn’t call any of this romantic in the literal sense. It was my last fling, as history would play itself out, as a bachelor/divorcee. The interpersonal aspect of this all was maddening, but to this day the sex that we shared puts a smile on my face.

[MF] Because I Changed My Mind

TL;DR A pushing 60 year old widower tells you about a recent event where he slept with a long-time female friend of his.

Disclaimer: If bareback i.e. “raw” sexual tales bother you then stop reading now. If drunkenness bothers you then stop reading now. It MIT bothers you then stop reading now.

I’d had a series of very shitty relationships, and make no mistake: a huge part of the years of epic failures was on me. Heck I even slept with an ex while she’d been married to someone, the father of their multiple children. Until I met my late wife I was a man who was kind of in the middle of the ocean on a deflating life raft.

[MF] Hate Fucking an Ex

TL;DR A pushing 60 widower tells you about the time he hate fucked an ex who, at the time, was married with 4 children.

What happened here was the result of a conversation I’d had with some (male) friends over lunch one day, in 1997. One of my friends was talking about this woman he worked with, how he hated her, and how he would totally be into “hate fucking” her if given the chance. Me at the time, kind of affable but at the same time totally naive and a serial dater, asked what “hate fucking” was. My guy friends laughed at me.

And yet I got a full on graphic description of hate fucking that started my mind racing. “You mean, you despise someone so much that if given the chance you would totally rail them?” I asked myself. “Well, that sounds like my ex, Mia (not her real name).” I could totally picture myself nailing Mia one last time. I’d always enjoyed fucking her when we were teens, and since I really hated Mia for her petty bullshit ever since we broke up after my freshman year of college, in my head I developed this scheme to combine brute force fucking with the (probably) awkward yet multiple couplings we’d enjoyed when we were in high school. Like the Six Million Dollar Man I wanted to fuck her, but bigger and stronger and better than before, but obviously on a much smaller fuck budget.

[MF] Wood in the woods and then in the bedroom

TL;DR A pushing 60 widower tells you about a five year period where, between a bad breakup and meeting his future (now late) wife, had this sexual awakening. This time it came out of the blue and it turned out to be a pleasurable afternoon, evening, and night. Following this a “committed” FWB happened, and there are many stories to share.

I’d met Sally (not her real name) at a mutual friend’s holiday party in Boston. I liked her immediately, but not in a sexual way. The 5’6″ BBW redheaded firebrand told dirty jokes and had this Just A Good Person quality that I took to immediately. Plus we’d both been through breakups recently. For her, a mother of three children, she had just completed a pretty ugly divorce. For me, never married, I’d broken up with my college sweetheart, or I guess you should say that she called me a “loser” repeatedly before having divulged that she’d cheated and that our relationship was done.