Our First Truly Successful Craig's List Encounter


Gold member
Aug 26, 2017
Several months ago, while KK was building up toward her another encounter, we recalled and discussed a memory of what we consider our first truly successful Craig’s List encounter.

That night during a long, passionate lovemaking session, while she was laying in my arms in between fucking, I was caressing her breasts and pussy, and kissing her neck and ear lobes.

She whispered a question, “Do you remember our first Craig’s List guy, that first time when it was so good, and it went just perfect?”

I was able to recall that encounter is pretty good, clear detail, and decided to try and give her a blow-by-blow retelling of the event while I stimulated her nipples, clit, and see what the reaction was.

That encounter took place about a year to year and a half after KK’s first “real” hot wife experience during a business/pleasure trip. The time between that first encounter and the Craig’s List guy she was trying to remember was a pretty rock, roller-coaster ride. Lots of hit-and-miss stuff, guys flaking out, guys that weren’t what she (or I) expected them to be, risky encounters, and not without its tension, ups and downs, and frustrations for both of us.

So, about a year and a half in, the two of us were talking one weekend, and over the course of that Saturday and Sunday discussed various versions and themes, plans and plots to try and make finding partners for my wife more reliable, less risky, and less stressful. That was the beginning of what she now calls “shopping for cock.”

The general initial idea we came up with was to try and take it slower, be more patient and thorough, and although there is a lot to say for spontaneity, we figured that we could set aside the excitement of the moment for a better overall experience. So we decided on some things like a pre-encounter face-to-face meet, that would give everyone a no-harm, no-foul “out” if there was no attraction or chemistry, or if the guy seemed like a problem. We decided on a strategy for health screening, which admittedly took more time to refine and evolve, and a strategy for where and how to do the encounters, usually in a near-by city, to combine the sex with a nice weekend or overnight getaway.

That first time, KK and I did our ad, put it up, and over three or so days we got about 600 responses. We learned a lot from just putting up the ad, and despite the overwhelming turn-out, she narrowed the candidate list down to three guys. She did a couple of phone calls with each of the three, one a short intro call, the other a phone-sex session - she decided if they couldn’t turn her on in her head, it would not likely work out in bed.

Out of that initial three, two made the final cut toward a face-to-face, and we got it all planned out, and made the short trip to that nearby city. I had been doing homework, and found the ideal hotel - a suite-style long-term stay place relatively near the airport. It was slightly upscale, clean, and the rooms had all the necessary qualities, and it did not require that our guest enter through a lobby, allowing more discrete entry/exit.

The day before we planned the main event, we met both candidates, one in the after-lunch time-frame, the other in the early evening. The first guy just didn’t click with my wife, and we called it quits in fairly short order. The second guy was a hit, and we left the wine bar that we chose to meet at, and went for a long car ride, so that KK could try making out with him in the backseat, and check out the goods. That was so fucking hot, but I found it to be almost too distracting to be safe - I had several close calls, trying watch them in the rearview mirror or some such to concentrate on driving. We drove around for about an hour and a half, with them kissing, touching, and making out in the back seat. Things might have gone further, but I was running out of places to drive that I was familiar with, and my distraction level was too high to keep going, so we drove back to the wine bar, and she gave him a little card with a telephone number and time on it for the main event the following day.

We got back to our hotel suite, and fucked each other’s brains out…

The next day, my wife spent about 2/3 of the afternoon hours preparing herself - the whole nine yards, including a massage, bath, having me shave her, doing her hair, make-up, and trying to figure out what she was going to wear. In the end, she decided on what looked like simple, classy office attire - a blouse, skirt, mid-heel pumps, and her anniversary pearls, a necklace and earrings. Outside of the norm was a garter and stockings, otherwise she had that hot female exec appearance.

The guy showed up on time, and my wife greeted him at the door. My only responsibility was to make sure that things stayed safe.

I watched for the first few minutes after the simple greeting hug and kiss, made sure everyone had a beverage, and then went to the upstairs suite, to give them some privacy. I hung out in the upstairs bedroom for a while, with the door open, so that I could hear what was going on, and take an occasional peek on the action. Over several checks, I watched the progression from the two of them sitting on the love-seat chatting, to casual touching, then kissing and making out, until the clothes started coming off. Once the action was in full swing, I stripped myself naked, and went downstairs to watch and jack off from the bar/kitchen.

The guy himself was nicely hung, not much difference in size from me, shaved smooth, and fit. I watched the two of them suck, fuck, and pleasure each other on the love-seat, until it was clear that they needed more space and comfort, then I went and took my wife by the hand, and led her to the downstairs master suite, and put her on the bed, legs wide apart, and took a seat in the corner of the room to watch her lover take her.

They fucked missionary style, doggie style, her in cowgirl, and reverse cowgirl, 69, him eating her, her sucking him, jacking him, and in other positions, over about a four hour span of time. He came at least three times, and I lost track of the number of orgasms my wife had. I jacked off until I could no longer ejaculate, cumming six times while watching them fuck each other.

One of the most memorable aspects was seeing the guy cum in her - I could tell it was happening, and he just kept pumping my wife, even after he shot his load deep into her. Her legs eventually were wrapped around him, and she was cumming hard, trying to muffle her cries with her own hand.

Another hot memory was watching my wife tease the guy’s cock back to hardness, using her stocking-covered foot to stimulate his cock.

She also let him mouth and throat fuck her at one point - lying on her back, her head over the edge of the mattress, with him standing on the floor, his cock sliding down her throat, and his balls dangling over her face. He used her big tits like handles, and she let him cum with his cock shoved down her throat, and swallowed every drop. While I was whispering this aspect of the event in her ear and fingering her, recalling it in detail, KK had an explosive orgasm hearing about my recollection of it.

The best part of that night was seeing my wife ride his cock, reverse cow-girl style, while she stared intently at me, and watched me jacking off, watching the two of them. Seeing his big cock pumping in and out of her made me shoot my load so hard it squirted from where I was sitting in the chair, onto the bed