The first several days - maybe a week after that first time were awkward and anxiety filled. The morning after, she was still a little hung over, and we talked very little about it, mostly me reassuring her it was OK, telling her how fucking hot it was, and trying to see how much of the details she actually recalled, or would admit to.
That encounter was bareback, and my wife worried and suffered regrets over it for quite a while afterward.
My wife has never been "happily monogamous," craves variety, and has a strong novelty seeking personality trait. After the first hot wife encounter, it led to her opening up about her needs and desires, craving for cock, and my obsession with all of it. We started finding strange men for her through a variety of paths.
During subsequent encounters after that initial experience, in almost every case, my wife demanded that her partner use a condom. She also had emotional issues about fucking other men, and even though she craved the experience, and variety of strange cock, she would not have penetrating sex, either vaginal, or anal for the first several months, even with her partner using a condom. She would instead have her lover put on the condom, and rub his cock against her pussy, or “ride” him, rubbing his cock with her pussy lips, but not allowing him to penetrate her. She also required the condom for oral sex, and even for a while, just to give a hand-job.
As she gained experience, and confidence, she dropped her demand for condom use for hand and blowjobs. My wife gives exquisite, eye-contact blowjobs, incredibly lascivious and sensual, and awesome hand-jobs, teasing, tormenting, and bringing a cock to the very edge of cumming, then backing off, and repeating until her partner is begging and whimpering to be allowed to cum. The relaxation of the condom requirement was definitely a win for me, as someone who thoroughly enjoyed watching those sessions.
I tried not to pressure her into taking a cock bareback, but I did occasionally bring it up during foreplay, or while I was fucking her, having her imagine it was a stranger’s bare cock cumming inside her instead of mine.
About a year into our experiences, we were enjoying a hotel encounter with a new partner, a fit, attractive male, who was very well-endowed. He provided a copy of a recent STD/STI screening to us as a courtesy - that was before our screening process was very well-refined. My wife still demanded that he use a condom.
A short while into the encounter, an experience she was thoroughly enjoying, after stroking, and sucking his big cock, she was ready to fuck. I was leaning back on the headboard of the bed, against a big pile of pillows, with my wife laid back against my chest. I was enjoying playing with her big tits, stroking the soft flesh, and teasing her nipples with my fingertips while our new friend was between her open legs, kissing and licking her pussy.
After he gave her an orgasm, her lover took a position between her open thighs, and his cock was fully erect, engorged. She said, “Fuck you have such a beautiful, hard cock!” I whispered into her ear, “Let him take you baby. Let him feel your hot wet pussy on that big hard cock…” She was overcome with lust, and that little encouragement was all it took - she rolled her hips up, off the bed a little, offering herself to him, and he slowly slid his bare, hard cock into my wife’s willing hole.
He fucked my wife long, and slow, and I fingered her clit while he stroked her pussy with that big cock. My wife had another orgasm, with the stranger’s cock deep inside her, which led to his orgasm, with his bare cock buried in her.
After he pulled out, I used his cum as lube, and fingered my wife’s pussy and clit until she had another orgasm, and then had her lick my fingers clean of his cum and her juices. He fucked my wife two more times that night, cumming in her both times.
After that encounter, we developed a thorough screening process, and every planned encounter, where we had confidence in the test results, my wife went bareback, and has been doing so ever since.
We've been doing this for about a decade now, averaging about three encounters in a calendar month. We don't count any longer, but my wife has been with hundreds of different men at this point, and we don't have any plans to stop.