A sticky quickie with Cassandra AKA The time I found out my best friend’s wife was an escort. [MF]

Cassandra. Cassie. One of the hottest people I’d ever met in real life, the fuel of a thousand wanks and many more still to come. Statuesque, curves that mesmerized and a confidence that flaunted it constantly. Short, dark, straight hair that made her look like something out of the fifties, always dressed to kill and tonight was no exception. A tight blouse and a tight skirt and boots that screamed “fuck me”. A hat that made her look like a hipster. Makeup that made her look like a movie star.

She was married to one of my best friends, who we’ll call Frank. I went to their wedding. I’d been to their place a couple days back, where she strutted about the pool in a bikini that had me jerking one out in their bathroom. She was close with my better half.

I was at a bar I never go to, with some friends I barely see, drinking myself into sociability when I saw her. It had to be her. She was supposed to be out of town on business. I know because I’d had a couple drinks with Frank beforehand.
She was smiling and flirting with an older guy who I would’ve believed was her uncle had be not had a hand on her thigh. I thought about calling Frank but I had to be sure, so I excused myself and walked over to the bar where they were sat, ordering a drink, catching her eye, making her expression turn.

“Cassie!” I said like I was surprised to see her.

“I think you have me confused with someone else” she replied without missing a beat.

It was her and I was confused, and more than that, intrigued. I got my drink and went back to pretend to give a fuck as my mind whirled. It couldn’t be an affair, because she could’ve had literally anyone she wanted. Why was she pretending her name wasn’t Cassie? I stared and she knew I was staring, and as soon as the guy with her walked away she waved me over.

“Hey babe… sorry about that…”

“It’s cool. You okay?”

“Yeah, great… have you… talked to Frank?”

“I saw him earlier… this place isn’t his scene, as you well know. I thought you were out of town…”

“Long story. Listen, could you do me a favour? Don’t tell Frank you saw me here. I’ll explain later. Can you do that for me?”

I nodded.

“I’ll be back in an hour. Wait for me. We’ll have a shot or two.”

An hour later she was back at the bar, so I excused myself and joined her. I ordered drinks, she ordered shots. She seemed flustered.

“You haven’t talked to Frank, have you?”

“Nope. What’s going on? Is everything okay?”

She downed her shot and spilled the beans, telling me that she’d lost her job a few weeks back, that Frank didn’t know, that her income mattered because Frank was elbow deep in a startup. Mortgage payments. Bills. Yada yada..
I ordered more shots.

She called it companionship. Another way of saying escorting. A polite way of describing prostitution. Essentially, she was telling me she was a whore. I felt sorry for her and sorry for Frank and sorry for my sordid imagination, suddenly picturing her getting fucked by the old dude at the bar, looking her over for signs. Her blouse was slightly ruffled. Her eyeliner was uncharacteristically imperfect. I felt dirty and ashamedly, aroused.

She said it would kill Frank if he found out. She made me promise not to tell him. She suggested we go upstairs to her room for a line, explaining that not only was she escorting, she was dealing. Easy money, she called it. We’d done lines together before. I never say no to free drugs.

Yes, my imagination was wandering. But my intentions were pure enough. Drugs and conversation and an opportunity to gaze and imagine, to fuel the wank I’d scheduled for the next moment I was alone. I was with Heather at the time, and we were happy. They were friends. I wouldn’t, I’d told myself, but in reality I probably would.

Her room was plain, small and tidy. No stray underwear, no sign of a cheeky vibrator, no half empty wine glasses. She pulled a generous baggy of coke out and proceeded to cut some lines on the dresser, telling me that beers in the minibar were off limits but inviting me to help myself to the vodka, which I did.

“Promise me you won’t tell” she repeated.

There was a desperation in her eyes, her tone. I promised. Watching her bend over to take the first line was delightful, her skirt riding up a bit, her ass doing a little wriggle as she snorted. She smiled and handed me the rolled up note. It was good coke.

She took off her hat and told me she had some time to kill before her next appointment. She said I was the only soul who knew her secret, that it was nice to have someone to talk to about it. She called me her confidant.

We did another line, and this time I watched her in the mirror, gazing at her cleavage somewhat unapologetically before taking my turn.
As I snorted the generous rail I felt her behind me, pressing up against me. Her hands on my belt.

“What are you doing?” I stammered, jacked up and nervous as all fuck.

“Making sure you don’t tell” she replied with a throaty whisper.

“We shouldn’t… you don’t have to… I won’t…” I replied like a pussy, or a gentleman, frozen, not stopping her as she unzipped me.

“I need to be sure.”

She reached into my boxers and grabbed my semi, pulling it free, squeezing it with her cold fingers. Making it grow.

“Do you think about me when you jerk off?”

I nodded. She started to stroke it, peeling back my foreskin, peering over my shoulder at the reflection of my oozing tip.

She let go and stepped back. I could’ve put it away, but instead I turned around and watched as she unbuttoned her blouse, as it came off, as she carefully hung it over a chair, getting harder. As she unzipped her skirt and peeled it off, pantyless, a little landing strip, not the bush I’d imagined countless times. Fully hard.

“He paid extra to keep them.” She said with a little shrug, answering a question I didn’t ask.

I tried one last time to half heartedly object and she brushed it aside, stepping toward me, wearing her boots, her bra and nothing else, unbuttoning my shirt as she explained how we had to, that it would be our secret, that she knew it was the only way I’d never, ever tell. Mutually assured destruction. I didn’t move. It was happening, but my last sliver of conscience was delaying my active participation.

My shirt fell open and she stepped back, looking me up and down, smiling at my not quite toned physique, at my bulging erection, at the trousers dangling around my knees.

“When you’re with Heather, have you ever imagined it was me?”

I nodded as she unclasped her bra and shrugged it off, finally revealing what I’d spent years imagining. They were lovely. Firm and perky, bigger than Heather’s but smaller than they were in my imagination, adorned with little, poky, perfectly proportioned nipples.

She pressed her naked body against mine, pushing me against the dresser, hoisting a boot up beside me, grabbing my cock and looking me in the eyes. They don’t have a word for how excited I was. There’s no suitable analogy. I don’t think I was breathing.

“You won’t tell”

Before I could do or say anything I was inside her, unsheathed, engulfed by her moist warm folds. I was inside Cassandra. I’d dreamt of it, but I never thought it would happen in anything but my imagination.

Fantasy is fun, but reality is a motherfucker. I exploded. Immediately. I tried to hold back. I thought maybe if I just pretended it was happening she wouldn’t notice, that I could keep it up through sheer willpower. That I’d just keep on going like nothing had happened and do all the things I’d dreamt of doing to her.

“You didn’t?” she said, bewildered.

I didn’t have to say anything. I was already limp. As I slipped out she shook her head.

She lowered her foot and stumbled back, telling me I’d set a new record, grinning as she looked at me and my limp, defeated cock. Yes, I was fucking humiliated. But the sight of Cassandra standing there naked with my cum hanging from between her dangling lips made everything better.

It was cool how casual she was about it, grabbing some tissues and sitting on the bed, facing me, thighs parted, carefully blotting up the mess as I stared. She called it our sticky little secret, that it was cute and flattering, that she knew I’d always wanted her but never realized how much.

She teased the possibility of a do-over, then looked at her watch and decided against it. I pulled my jeans back up and watched her get dressed, a process that was infinitely longer than our sticky secret. We did another line.

“I won’t tell” I said by way of goodbye.

“No shit speedy” she giggled.

Source: reddit.com/r/gonewildstories/comments/gdlfla/a_sticky_quickie_with_cassandra_aka_the_time_i