He Went Home with the Wrong Woman on Halloween 4: The Older Woman and Her Husband

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Our final letter came in after we put out a call for more crazy Halloween experiences, and this reader certainly didn’t disappoint. His story is extreme, so consider yourself warned.

He tells of how he was taken home by an older woman after a Halloween party, where her husband watched the entire time. He was drugged, bound, gagged, and whipped into a mess, with both of them enjoying his torment. This one isn’t for the faint of heart, but if you dare, we’ll be publishing it soon.

Now, here in it’s entirety, published for the first time, Barry’s letter:

Dear FemdomU Magazine,

I’ve had my share of weird experiences, but nothing compares to what happened one Halloween a few years ago. It’s the kind of story that sticks with you, partly because it was one of the wildest nights of my life, and partly because I can’t believe how it all went down.

It started at an adult Halloween party, the kind where the drinks are heavy, and the costumes are lighter. I was dressed as a gladiator—shirtless, in leather straps, feeling pretty confident. I hit it off with this woman, who was dressed in a sleek, black catsuit, her eyes sharp and her demeanor even sharper. We got to talking, and after a few drinks, she confessed something wild: she loved pegging men. But her husband wouldn’t let her.

Now, I was feeling pretty bold at this point. The drinks were talking, and I told her I’d let her. She grinned, told me to come with her, and before I knew it, we were in an Uber heading to her house.

At her place, things moved quickly. She led me into her garage, which had been converted into a BDSM room. It was intimidating, full of whips, chains, and various implements of pain. I got nervous, but she assured me, “Don’t worry, I’ll be gentle. C’mon, my husband won’t let me, but you said you would.”

Drunkenly, I agreed. I was already half undressed, so she led me to a spanking bench and bound my wrists and ankles. That’s when her tone shifted. She wasn’t tipsy anymore—she was completely sober and in full control. And what followed wasn’t anything gentle.

The first crack of the whip across my back took my breath away. Then another. And another. The pain was sharp, far beyond anything I had experienced before. I’ve been whipped in some kinky sessions, but nothing like this. She whipped my back, my ass, leaving welts that stung like fire. And through it all, she was laughing, feeding off my cries of pain.

Just when I thought it couldn’t get any worse, the door opened, and in walked her husband. He was smiling. Not an angry smile, just a cold, satisfied one. He sat down in a chair, crossed his arms, and watched as his wife continued to lash me.

The whipping went on for what felt like hours. By the end, I was a mess, whimpering, my back and ass burning from the relentless assault. She finally stopped, and then—get this—she took a picture of me. She showed me the photo, and I was covered in welts and blood. And the crazy part? It turned me on. Seeing my body like that, as messed up as it was, I couldn’t help but feel aroused. It confused the hell out of me.

Her husband just kept sitting there, still smiling. But I didn’t have time to process what was happening, because she moved on to the next part—pegging.

Now, I’d been curious about pegging, and that was the whole reason I’d agreed to go home with her. But what I wasn’t prepared for was the sheer size of the dildo she chose. It was far too big for a first-timer, and she knew it. I think she actually enjoyed my screams. The mix of pleasure and pain was overwhelming, and she yanked my head back, forcing me to make eye contact with her husband as she fucked me. The whole experience was humiliating, but I was too far gone to stop it.

After a while, she finally stopped and said she wanted to untie me, but only so I could pleasure her. She told me I could either obey or fight back, but if I tried to resist, her husband—who was twice my size—would fuck me up.

I wasn’t about to test him. I agreed to obey.

She untied me, led me to a couch, and told me to kneel in front of her. First, she made me lick her feet, then she ordered me to go down on her. I did as I was told, with her husband sitting right there, watching the whole thing. Eventually, she ordered me to fuck her.

I hesitated, but again, I obeyed. I climbed on top of her, and she ordered me to fuck her rough. So, I did. I was pounding into her, making her scream, and I made the mistake of looking at her husband. His smile was gone. Now, he looked furious.

Before I knew what was happening, he leaped up from the couch and punched me square in the face. I hit the floor, dazed and confused, my vision swimming. When I came to, the husband and wife were fucking right there on the couch. I didn’t stick around to see what happened next—I grabbed my clothes and bolted out of there as fast as I could, still half-naked.

And here’s the craziest part: I’ve spent the last two Halloweens at the same bar, hoping to run into that couple again.

Weirdest night of my life? Absolutely. Would I do it again? Maybe.

Sincerely,
Barry