Planet Craigslist: For Fifty Bucks

Planet Craigslist recounts my years of trolling men with a series of depraved sex ads. The entry outlining the project can be found here: Planet Craigslist: Bang My Mom

A man offered me fifty bucks to suck my cock. He came from the depths of Craigslist, a pit of pleasure whose citizens employ the shotgun method: Send scattershot emails and hope to hit a willing target. When the intended says no load your words and shoot again. I myself was entrenched in this world, writing my own ads for sex while trolling others. On the same night I’d fly a shingle both as myself and some woman. The female I pretended to be got dozens if not hundreds of offers. They ranged from plain vanilla to those bubbled from the devil’s id. Pedophiles and animal fuckers slimed their way into my inbox. I’d fuck with their brains then block them.

With my own ads I received few offers. I was another white straight dude in a city that hoarded them. Humor helped but most times my cast words slipped to the internet sea and sank to the bottom. No responses. Never read. The few emails I got were almost always men. Their replies fell within the same short range:

Hey if no one gets at you I’d suck you off tonight.

Want a massage? I’m trained. We wouldn’t have to do anything if you didn’t want to.

Want to meet me on the bike trail? You pull up, I suck you off, and then you go.

I’m a straight guy but feeling alone tonight. Want to come over and blaze it? I got party favors. We can watch DVDs and I’ll blow you if you want.

The replies were almost never aggressive and rarely individualized. Men blasting off a million emails, too busy with their own thing to bother beyond that. Still their behavior confounded me. I posted in Male for Female but they scaled the walls to find my ads. To assault my inbox with dick pics.

I wondered if there was a thrill for them to hook up with a straight dude. The same line of thinking employed when one thinks their dick will turn a lesbian, if only for a night. I didn’t know their inner world so only poked blind for any truth. Sometimes I replied with a polite no thanks but soon learned not to. To say no was an invitation for them to beg and try change my mind. To send emails ’til I blocked them.

Certain men responded over and over. An older man was infatuated with me and sent many missives. They asked how my night was going, if I’d had success. He’d attach pics of himself unsolicited. They seemed neither dirty nor normal. Shirt undone, him lounging in undies. Bait I’d never take. He’d change his name and only reveal it was him after a few replies. If I told him I’d had no luck he’d bemoan the foolish women, saying he’d be happy to have me. That he could even just offer a massage. I always said no or ignored these parts.

I don’t know why I answered him, only that he was odd and didn’t mind the attention. It’s a natural part of me to be a pragmatic appeaser. To avoid confrontation. To not outright reject someone with a sexual advance for fear it might hurt their heart. I thought kindness then curtness would send the message. But after many months I stopped responding. He still emailed from time to time but I’d just read and delete.

Beyond the talkers there was another type of Craigslist citizen. Those that proffered drugs or cash. Gifts for my time or to entice me. They’d disguise it by calling it gas money. The offers ranged from twenty to a few hundred, often with coke or weed on top of that. Almost all wanted to suck me off, rarely the other way around. As best as I can recall few wanted to be topped or top me. Strictly oral. Their mouth to my cock.

Many described themselves as straight. That they were chill, just wanted to suck a dick. That what lived in my pants was utilitarian. A scratch for an itch they had. No time for a woman, just needed some fun. I don’t know if they were gay but pretending to be straight, straight but experimenting, or somewhere on the spectrum of bi, queer, or questioning.

It didn’t matter to me but there seemed an overt need to let me know they weren’t gay. To protect their masculinity. That they were straight but wanted to suck my cock. That they’d gift me $150 and a few lines as gratitude. I wondered if the straight angle was merely a way to further entice me. A chance to say I’m the same. Suck my cock but no homo.

I deleted these offers as they came. They arrived as regular as those offering a massage or to blow me on the bike trail. All part of Craigslist life. After the swat I gave them no second thought. But one man kept at it in a persistent though non-pushy way. I started an exchange with him, saying no thanks but wishing him luck. Instead of the usual begging he respected my decline. Told me to let him know if I changed my mind.

A seed sprouted in my brain. After all, I’d scoured Craigslist for not just connections but strange experiences. This place was a playground of unspoken desires, the carnal stripped down to its raw and primal form. People with no shame in what they wanted. I hoped to chat with cool women and sleep with a few of them. But I also possessed a desire to put feelers for what was out there. Strange experiences. Not for pleasure but curiosity. Access to the inaccessible. This plane was a portal for just that.

I felt plagued by an image my mind engendered: me shitting on a man’s face. Blasting yuck as he jacked it. Him slurping and gurgling my shit. Me walking out his apartment as he lay covered in cum and feces. I thought it’d be weird and funny. Something to write about. But as I dug down I found I didn’t possess the grit to go through with it. There had to be something else.

At the time I was desperately poor. I started eating from dumpsters along with leftovers my roomies left to rot. I started donating plasma for $300 a month. I also had some savings but they dwindled fast. Life expensive even on the cheap. In light of all this the offers of cash for cock now felt enticing. My wallet approached broke. Rent neared due. Would it really be weird to get sucked off and make money in the process?

I pondered this for weeks, each time dismissing the kernel of thought before it popped. At the same time my money fortunes didn’t improve. I performed odd jobs and plasma helped but still my account circled the drain. But every time I thought of meeting a man to get blown it scared me.

It wasn’t a moral question. I’d never understood the shame or stigma around sex work. It’s a job and people should have complete autonomy over their bodies. We all want to explore sex but ostracize those who provide it. What I feared was entrapment. Disease. Someone finding out. But most of all getting hurt. So many of these men felt off. Sketchy. Not answering to no. Something in my gut didn’t sit right. Rational or not I didn’t want to meet a strange man for fear they might rape me.

My mind turned back to the one whose offers came gentle. He said it’d be an honor to suck my cock and how much he wished he could. He told me a bit about himself. He was in his late 30s and managed the deli section of a grocery store. He lived in a house with roomies and identified as gay though sometimes had sex with a female coworker. Everything in his tone and approach put me at ease in ways the others hadn’t.

I picked through the coins in my car and room, looking under seats and in drawers. Even with that I was still short on rent. I didn’t think I’d make enough in time for the end of the month. I’d never missed a rent payment in my life and didn’t care to start now. Had never taken on a penny of debt so wouldn’t do that either. To pawn things felt pathetic. Some new life low. Plus I owned nothing of value. I slept on a floor mattress, used a $50 phone, and drove a car with 200,000 miles. My net worth registered as no more than a few hundred dollars.

One night as I ran my ad the deli manager contacted me. I’d told him no a few times but when he offered money I said I’d think about it. He proffered his name as M and asked me to name my price. I had to assess my value. Prop my sexual worth to the auction block. I knew I was good in bed with women but didn’t know how I’d perform or appear to a man. So I looked in the mirror. Past prime steak. I’d have to dust off the maggots and hope for a bidder.

I’m straight average from top down and didn’t want to overshoot. I thought of asking for $100 as I’d been offered this many times before. It needed to be worth my while but if I went too high I’d lose him. I came in at $75 and he countered with fifty. I think we settled on sixty. I felt relief and nervous excitement. I needed the money for rent but also was interested in the experience.

From adolescence to now I’d never felt attracted to a male. I recognized beautiful men but never never had a tingle when they touched me. I lamented not being bi as I’d seen how sex came to men attracted to their own. They had access to hookups with little trouble. It was so different from my own experience. But that’s not who I was. I couldn’t trick myself to like men any more than I could trick myself to like women. Still, I wondered how it’d feel to have my cock in a man’s mouth. How the experience would register in both brain and body.

We agreed to meet at his place in the afternoon. M lived across town and it took twenty minutes to get there. My roomies didn’t know what I was up to. I felt no shame but didn’t care to be questioned. I parked four blocks from his home so he couldn’t see my car. Took a shot or two to ease the nerves. I wasn’t sick or anxious, more curious but unknowing.

Even though I felt safe I left my shoes and ID in the car. I knew that if I had to flee there’d be no time to collect them. I memorized the route and carried my cell in case I needed 911. All this prep just to get sucked off. It made me contemplate what women go through for every first date. Of those I’d never met but still invited me over to fuck them.

It was April, the earth wet. Fall leaves rotted, spring buds bloomed. A months long gray sky spitting rain had cast across the city all winter. Now the tendrils of spring rooted in, commingling with the cold of winter. I stepped down the dark grey sidewalk barefoot, scanning houses to see which was his. The neighborhood was nice which made it feel less sketchy. When I found his home I confirmed that I wanted to go through with this then walked up. Looked over the steps once more in case I needed to run. Then I knocked at the door and M answered.

He greeted me in the entry wearing a white shirt and jeans. M looked nice for his age, handsome enough. He sported a mustache and close cropped hair. I’m over six feet tall and took note of how small he seemed next to me. His head to my chest. M’s dog barked from behind then ceased. I thought of shaking his hand but instead we hugged. I leaned down to do it. Wrapped my arms around his back. It seemed he liked what he saw. How I felt.

As soon as he opened the door any worries over my safety sifted away. His disposition was the same as online. Chill, not pushy, happy to have me. I made the usual chit chat for a minute, saying the house was nice, asking if the roomies were around but they weren’t. In these situations, meeting a stranger for sex, I never know the proper decorum. Bullshit a bit or just get to it? I told him let’s see his room.

He led me up the wooden stairs and opened a door. The room was plain but painted yellow. Little more than a bed and dresser. He closed the door and locked the dog out. I stood and he approached. M put his arms around me and kissed. Babbled a moan of pleasure. His whiskers scratched at my nose and lips as I stood there.

I’d never kissed a man before. It felt like putting my lips to a piece of rubber. Sterile and lifeless. I likened it to making out with my pillow in seventh grade. No passion but no distaste. In the days leading up to this I feared I’d feel repulsed. Wouldn’t be able to go through with it. Would walk out with neither money nor experience. Plus leave him dejected. But now I felt nothing. Just kissing rubber.

M pulled my shirt to kiss and suck my nipples. He thrust a tongue to my mouth, his sentry bouncing off teeth and cheeks. After a minute he laid me on the bed. He then crawled over and kissed once more. We hadn’t discussed kissing. It hadn’t even occurred to me. But it set the mood for him and I didn’t mind. So he kissed my lips and bit my nipples. As he did this I felt like an anthropologist outside my body. Not in a traumatic sense but one of curiosity. This is something I was both a part of but outwardly observing. The absurdity made me laugh on the inside.

M removed my pants and boxers. Took delight in what I had to offer. He unzipped but left his pants on, pulling his cock out. It appeared big, purple, and swollen. It sported a bulbous head and sharp curve along the shaft. He wanted to sword fight so rubbed his against mine. I made mine hard then held it up as a practice dummy, no parry on my part. Just taking blows from an over engorged opponent. He removed his jeans but kept his boxers, cock still flopped out. Then M crawled to the back of the bed and put me in his mouth.

I looked ’round the yellow room as he did his thing. He moaned in delight as he sucked me. I had no trouble staying hard but it felt like a wet cloth across my cock. I thought of how much of sex is mental. Is chemical. Is elemental and innate. His oral skills were as good as any woman but there were no sensations of pleasure. He asked to eat my ass and I consented. Told me I’d love it. As he lapped his tongue all I could picture was a St. Bernard slathered in drool, gorging its food with flapping jowls.

He played with himself as he blew me but never fully masturbated. His cock stayed purple and swollen. I knew I’d never finish from his mouth so after fifteen minutes started jacking. As I did he hovered his lips over the head of my cock. I thought of the woman I’d last slept with. Her beautiful body and how it felt against mine. In fact I’d told M I was seeing her even though I wasn’t. It seemed a convenient fib but not one far off. She was here in my head as my hand brought me to completion.

I signaled I was to cum and M sealed his mouth back over. I sent a hot shot to his throat which he sucked and swallowed, all the while moaning and playing with himself. In emails he’d emphasized how important it was to eat my cum. I gave him a moment to ingest the load. To enjoy the taste. His meal complete. He straddled once more and kissed. Though he’d just had my cum in his mouth and tongue in my ass I didn’t mind. Then he crawled off and I went to redress.

As I donned clothes he took out his wallet. I hadn’t mentioned money the whole time, feeling it awkward to ask him. He spared me the need by counting bills with no playact or embellishment. It was silent as he did this. I didn’t know what to say but felt a bit weird so mused my thoughts aloud.

“Ah yes, the awkward part.” He smirked and forked over my cash.

M put on his pants and I stuffed the bills in a pocket. I’d got what I came for. The money for rent and a weird experience. Came out safe on the other side. Now knew more about my sexuality. A confirmation of no attraction to men. No desire for their bodies but no repulsion either. Like eating a bland meal. No want to try it again but no biggie that I had. M walked me down the stairs and to the door. He said he couldn’t afford to do this often but would like to again. I doubted I’d hear from him and didn’t. That was fine. I didn’t see myself making this routine.

I left his house to meet with friends. Walked barefoot to my car in the rain. I didn’t have much time so cleaned drool off my cock then made way. My friends and I were having dinner together. They didn’t know what I’d just done. By the time I arrived I myself forgot it. This whole encounter ephemeral. I gorged my meal but didn’t reflect. It was just something that happened. No strangeness nor significance. Another Craigslist encounter in the books. I’d live through many more but for now I was just happy to have my fifty bucks.


If you’re a billionaire who likes my writing but can’t cum unless you help me afford more than dumpster food then you’re in luck. Ways to support my work can be found here: https://gabfrab.com/make-a-wish-gross-hobo-edition/