About a year or so into the Craigslist encounter thing, I had my first truly negative experience.
The scenario was a husband setting his wife up for a surprise encounter. I failed to press for engagement with the wife, on the basis of said "surprise." The husband was convincing, that she was on board with fucking another guy. I had no reason to believe otherwise.
The scene we agreed to was kind of weird. I'd book a hotel room at a specific location he'd chosen, with early check-in. I was to ask for two keys, leaving one at the desk for "Carl & Kim," in an envelope, informing the desk clerk that they'd be around in the noon time frame. Then I was to wait in the bathroom, concealed in the tub/shower stall with the curtain pulled, lights out, bathroom door open. He would signal me from the bedroom once the two of them were ready - his job was to warm her up, then I'd appear for the fucking.
He had lots of rules and constraints; condom required, no kissing, no oral sex, just straight fucking. Specifically he wanted to watch me fuck her, then have her clean my condom-covered cock off with her mouth while he stroked to the whole thing. Then they'd leave after it was all done. His description of his wife was somewhat intriguing - he verbalized that she resembled strongly a local newscaster, a busty, leggy, tall blond. We went around via phone and email for a few days, bandying about details, etc. before I agreed.
The day of the planned encounter came. I executed accordingly, checking into the specified local resort hotel on an early reservation, 11:00am sharp. I got two room keys, left the desk, returning after I checked out the room, the key already placed in the hand-written envelope. I handed the envelope to the desk clerk, told her, "Carl and Kim" would be stopping by around noon, asking for it. The clerk had a sort of quizzical look on her face, my response was "concert tickets" - we're meeting later tonight for a show. It seemed to satisfy her, she took the envelope, said, "No problem, sir. Enjoy the show!"
I went back to the room, stripped out of my clothes, opened the computer bag I was carrying, found the strip of condoms I'd brought along, opened one, removing it from the foil, then stashed everything in the closet, atop the shelf, tossing the extra pillows on the back to better conceal it.
Next, I went to the bathroom, carrying the unwrapped condom in the fingers of one hand. I took a look around, turned off the light, got into the tub/shower, pulled the curtain, letting its hem hang outside the tub wall. I was partially erect at that point, it was approaching the noon hour. The next several minutes passed like they were hours. With each passing minute, I was getting more anxious, harder, more erect with anticipation. Straight-up noon, I rolled the condom carefully on, slowly, making sure it was not too tightly stretched, and conformal with my cock head, shaft, down to the root.
As I waited, my breathing intensified with the anticipation, I slowly, gently played with my balls, thinking about what was next. I heard them come into the room - their entrance was noisy, laughter, comments from a female voice, "What are we doing? What have you cooked up?"
Probably five minutes passed - I could hear creaking noises from the bed, more laughter. My cock was rock-hard. Then the husband said his key phrase, "I've got a big surprise for you Boo."
I quietly moved the shower curtain aside, stepped out of the tub, making my way to the bedroom. I was completely nude, very hard, my condom-covered cock throbbing with anticipation. I found them in bed together, her husband laying beside her. They were both nude. Kim was by initial appearance pretty much as her husband described, similar to the local newscaster, blond, leggy, maybe a little thicker/chunkier, but quite attractive. Carl on the other hand was fat, hairy, pasty white, a complete, total mismatch to his attractive wife. When Kim saw me, she gasped. That was followed by "Oh my fucking God!"
Carl rolled his fat ass off the bed, pulled the desk chair over beside it, plopping his corpulent self, bare naked, into the chair. His sweaty skin made disturbing sounds against the vinyl as he squirmed around, getting comfortable. He said, "I want to watch you with him Boo. I want to see him do you."
By that point, Kim, or "Boo" as Carl referred to her, had pulled her knees up toward her chest, covering up with the bed sheet. She looked terrified, reluctant.
Carl urged, "Do it Boo. Do it for me, just once...?"
My reaction was mixed. I was still hard, but finding it difficult to maintain my erection. Her reluctance was pretty obvious, I was concerned about consent. After pausing, I said, "Are ya'll sure you want to do this?"
Kim seemed to relax a bit, possibly the notion that she had some say in the matter influenced her into a less defensive posture. Kim tugged the sheet down below her boobs, exposing them. She wiggled in the bed a little, and said, "Well, I guess. Let's try it. Join me..."
I was relieved, joining her in the bed. Carl looked like he was quite anxious, leaning forward in the chair, his eyes big, wide open, breathing through his mouth loudly, clearly sweating, despite the cool air in the room.
Trying to follow the rules, I reached out, guiding Kim to remove the sheet she was covering herself with. She was receptive, in a couple of seconds, Kim was on display, fully nude, from head to toe. Her thighs were still together however. I moved closer to her, straddling her at the hips, my erection throbbing. Kim was staring at my cock, licking her lips. I waited there, displaying myself to her, then turned toward Carl. He was reclined in the desk chair, stroking his tiny cock with the tips of two fingers, fixated on us.
Kim pushed herself around in the bed a bit, laid back, and said, "Ok. Do me."
Still on my knees, I maneuvered back, spreading Kim's thighs in the process, positioning myself between her legs. After a little more positioning, I had Kim in a comfortable starting posture. I grabbed my condom-covered cock, using it like a finger to stimulate her labia. When she started to open up and lubricate, I pressed a little harder and deeper, working my latex covered cock-head into her a bit at a time. It took maybe a minute for her to open up fully.
Normally, I enjoy foreplay. In part, I'm average to larger than average, thick, and I enjoy it when my partner is wet, receptive, and I don't have to worry about inflicting pain during penetration. The "rules" as handed to me precluded most of the normal foreplay elements, so this was not my usual experience. I penetrated Kim, slowly, deliberately, carefully, until I was deep inside her, our pubic mounds pressed together, balls deep inside her.
At that point, fat Carl was mostly out of the chair, furiously stroking his tiny little ********-********, trying to get a better look. Kim had become lubricated sufficiently that between her juices and the lube on the condom, I was ready to start the fucking in earnest. It was somehow satisfying to know her micro-penis husband was seeing a "real man" plow his attractive wife.
After several minutes of thrusting, a marginally enthusiastic Kim said, "I want you to kiss me..."
Carl objected strenuously, "No Boo-baby, No! No kissing."
Kim's response was pretty blunt, "Fuck you Carl. This was your idea. I'll kiss him if I want."
Taking Kims lead as authoritative in the matter, I did as requested - I started kissing her. That intensified things significantly. Kim was getting much wetter, the feedback cycle was unleashed. The condom, which I was not terribly fond of, was actually a help, desensitizing me sufficiently to delay ejaculation, allowing me to thrust frequently, deep into Kim's ever wetter cunt.
Then the big surprise happened. Only I'm not sure who was more surprised, me, or Carl. Kim stopped me from thrusting, pushed me away, and off her, rolling me onto the bed on my back. Kim grabbed my cock, ripping off the condom, then mounted me. It was an awesome cock ride.
Carl in contrast was pleading with her, "No Boo! No! You can't fuck him like that. No! Don't you cum in my wife! Please don't cum in her!"
That seemed to goad Kim into more deliberate action, "Fuck you Carl. Do you like it? Do you like seeing his big, hard cock inside me? Bare naked? I'm going to make him cum. He's going to cum inside me. There's nothing you can do about it!"
Kim shifted a bit, gaining a squatting position atop me, on the balls of her feet. She was bouncing on my cock, up and down. The sounds were terribly erotic, the squeaking bed, the squishy, wet sounds of my cock inside her wet, gaping hole.
Carl was sobbing, weeping, "No Boo, No! Don't make him cum... not inside you, please Boo, No. Please don't cum in her! Please don't cum in my wife!"
That was all it took. I unloaded in her, blasting every drop into that devious bitch. She was vocalizing, "Carl dear, he's cumming. He's filling me up with his cum. Oh God it feels good. I can feel him cumming in me..."
At that point, Carl had fallen to the floor, curled almost in a fetal position, sobbing intensely, muttering unintelligibly under his breath. About all I could make out was stuff like, "Oh God, oh no!"
Kim and I were in afterglow embrace, enjoying the post-orgasmic mix of endorphin release, sex sweat, the the rivulets of cum flowing from Kim's used cunt, all those wet, nasty, naughty sensations.
Neither of us were too concerned about Carl. After about ten minutes of post-fuck cuddling, Kim said, "Gotta get back to the office. I'm past due. Carl, you stupid bastard, get up. We gotta go."
I fetched Kim a towel, returned with it, watching as she wiped herself down. Carl had still failed to respond, lying curled on the floor beside the bed. Kim said, "Carl you pussy! There's cum on the chair seat. Clean it the fuck up and get dressed! I have to go. Get your fat ass up or I'm leaving without you!"
The situation felt awkward. I was reclined on the hotel bed, still naked, for some reason getting hard again. I watched and listened to Kim's brutal monolog as she dressed:
"I knew this would fucking happen. Carl you micro-penis baby-man, get the fuck up, clean up your cum you disgusting pig!
I'm so sorry - teenie-weenie Carl has been begging for this for fucking ever, but I knew he couldn't actually take it, you know, watch me fuck. I should divorce his sorry ass. Maybe better is I'll just fuck real men, on my own, from now on.
God I don't fucking know why I listened to my damn mother, save yourself for marriage, what bullshit. What a disappointment! If only I'd known better, listened to my instinct...
You have such a nice package! (Kim looking directly at me, and my swelling hard-on).
(Looking down at the floor) Carl, I told your sorry fat ass to get the fuck up! You're making me late!"
Apparently Kim was OK going back to the office with a load of my cum in her pussy - I watched her pull on her panties without any further clean-up, then she finished dressing. Kim walked over to the chest of drawers, fumbled around with the stuff strewn on top, grabbing what appeared to be a set of keys...
Her parting shot; "Carl you fat fuck! I'm leaving you here. You're on your own. I'm going to work."
With that, Kim turned, opened the door, stepped through and let it close behind her. Fat Carl was still wallowing on the floor, crying. He looked like a grotesque, beached whale. My hard-on was completely gone - dead. I pondered next steps, electing to shower, dress, ignoring Carl. The hotel room was paid for, I figured at worst he'd continue wallowing in the floor until housekeeping or staff found him the next day - he'd become their problem, not mine.
I ended up leaving Fat Carl rolling around naked, weeping, on the hotel room floor, and went on about my day. That encounter was a blend of negative and positive, definitely weird. It wasn't to be the first.