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For a couple of years I’ve been posting about my now-failed marriage. This is the full story of how it slowly transformed from a cuckolding dynamic, starting with her ex-boyfriend, and how it ultimately led to our separation, divorce, and her moving in with her new boyfriend. It’s part twisted arousal and maybe a cautionary tale.
Right after we (56M) and Kelly (42F) got married in early 2023, our sex life stalled hard. The spark that was there during dating just faded almost immediately. I was completely denied intimacy after our honeymoon.
Five months after the wedding, we were on a trip, when we finally had a long, raw dialogue about it. We talked about our sexual pasts — I admitted to a few bi encounters I’d had, and she opened up about wild threesomes and more she’d had during her jam-band hippie chick days. The conversation got us both turned on, and we agreed to open the marriage, hoping it would reignite her libido. Knowing she and Dan (45M), her last boyfriend, were still in contact, I suggested him as the ideal no-strings partner. Dan is a barrel-chested ski bum who shows up in a camo trucker hat, a hoodie, pajama pants, and fuzzy black boot. They’d been friends-with-benefits for 15 years. She didn’t hesitate.
The very next morning she sent me this excited message about Dan texting her out of the blue with a dream about her and how crazy it was that he reached out first thing in the morning.
Shortly after, I helped arrange for her to slip away from a family trip to meet him at a hotel. There she finally told him she was in an open marriage. He was totally good with it. She sent me the glowing “it was a great night!” text the next morning after they spent the night together. She wanted a “don’t ask, don’t tell” rule, so I stayed in the dark about almost all the details which only made the fantasy burn hotter in my head.
Right after that, she snuck out to see Dan again. I flew her first class, rented her a BMW, and booked her this beautiful lofted hideaway condo. One morning during that trip she sent me this selfie, right after Dan had left for work, flushed and glowing from the night before.
For the weeks that followed, she bounced between desperate to see him, pissed when he went silent, and giddy when he finally replied. We made a trip to Denver together, and one night she left me alone so she could go see him at his apartment. She ended up extending her stay one extra night. On the way to the airport, I dropped her off at the Four Seasons where I’d booked them a corner suite.
We planned another trip to see her family. Kelly wanted to sneak in early to see Dan, so I got us a luxury downtown condo so they could spend a couple of nights together. I flew in and killed time to arrive after she and Dan were done. She was absolutely wrecked after two nights with him. He was especially rough knowing I was going to be there. Kelly has always been incredibly skilled at oral — she takes her time and clearly enjoys it. The thought of her with him while I waited had me throbbing.
During this period I remained completely denied. Kelly loved teasing me about it. She’d joke that I got harder thinking about her with other men than I ever did with her, mock my style of dressing, and bring up some of my former male friends. At one point I introduced her to Jeremy, a young, muscular black guy who coached high school football. She’d had a few black boyfriends in the past, so I thought there might be chemistry, but nothing ever developed (that I’m aware of;).
Long after the Dan chapter was over, she started making regular solo trips to reconnect with her old jam band party friends. The group included Colin (44M) — tall, blonde, lean fitness type, a single dad for ten years and the ex-husband of one of her friends. After her very first trip, Kelly casually mentioned how tough it was for Colin to find a girlfriend in their small town.
A few months later, she planned a trip to a jam band concert, sharing a house with her friends like the old days, and Colin was picking up at the airport. I encouraged her: “If you want to fuck him, go for it.” She’s always been a DTF hippie chick, so I knew it was a possibility. Honestly, looking back, she probably would’ve done if they’d had more privacy. She denied fucking Colin or anyone else, but that denial only fueled me.
Soon after that concert trip, we decided on a trial separation. From that point on she ramped up the frequency of her trips — some were camping, some “girls trips,” others overnight concert runs with pretty unclear sleeping arrangements.
Before every trip, she’d do full glow-ups: hair stylist, nail salon, new outfits — all of it paid for by me. I was still covering all her bills and the mortgage on our house. Paying for her to look her best was its own special kind of turn-on.
After a couple of months of these regular hangouts with her friends, Kelly asked for a divorce. She said she was moving to be near her friends and planned to get her own place. I agreed and kept supporting her financially.
Next, I funded even more of her upgrades: Botox facials, a $17k new smile makeover, and a brand-new Lexus SUV so she could make the drives comfortably. Spoiling her so she could present herself perfectly for Colin made my own pulse race every single time.
Not long before the papers were signed, she confessed she had been dating Colin for several months. She said she wanted clean karma. Hearing it left me turned on.
Soon after, she asked if Colin could visit her at the house I was still letting her live in rent-free. He thought it was the right thing to meet me, but it never happened. I said yes anyway — wishing the cameras still worked so I could have listened.
A couple months ago she said she wasn’t getting her own place. She asked if I would pay for her to live with Colin. We agreed it was basically the same support as if we had stayed married. The idea of subsidizing their life together got to me.
Now she’s packing up. Colin and a friend are helping move everything to Western North Carolina, where she’ll live with him full-time as his girlfriend. Colin gets a live-in partner who pays half the bills… with my money.
As weird as it sounds, I’m still turned on by it. Kelly knows her power over me and still teases me with just enough details to keep me edged. The thought of her with him while I fund their lifestyle keeps me hard.
It’s been quite an evolution.