Virtual cheating with kink under the direction of a woman

NSFW

Ive had irl cheating experiences before, but the dirty nasty depraved ones seem to be even hotter to me than just finding a homewrecker to fuck.

Anyway, back in the yahoo chat room days I came across Karen. We chatted and it became ongoing. Eventually I'd jerk for her regularly. And she always pushed the envelope. Always late at night after the wife went to bed.

First it was just me jerking and I told her through chat. Then I was jerking on cam for her. The shed convince me to show her the wife's panty drawer and grab a pair. I'd jerk into those while she watched. Eventually she pushed me to wear them and stain her panties. It progressed to adding a bra, then snooping through all her lingerie she never wore. She had me dressing like a slut and always cumming for her in the wife's most private things. Or even at times dressed and random objects, anything she could find I could taint. Eventually she also added me filling my ass and jerking for her. It just went on and on.

However the cherry on top was one night the wife was out cold on back pain meds. She got me dressed up, and had me jerk over her head while she watched. I ended up cumming in her hair. Next morning she woke up and realized that something dried and crusty was in her hair. I was grinning ear to ear on the inside.

Miss that girl, and addicted to finding someone like that again, just willing to always push the envelope of depravity.

Posted Aug 13, 2026, 4:48 PM UTC

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