Another Friday night alone at home, clicking through video after video, trying to find some new porn that might work for me.
It wasn't that I had some hyper specific fetish, I was just bored. I had done alright for myself in college, but the dating world had drifted away from me as I got a little older and focused on my career. I had become desensitized to a lot of porn out there, and jerking off was feeling more and more like a chore.
I closed my browser window with a sigh and thought about going to bed early. If my desire to jerk off had waned, my sex drive definitely hadn't, so I sat there in frustration, my brain arguing with itself.
*BING*
An imaginary lightbulb appeared above my head as I reopened the browser. I hadn't gone this route before, but desperate times called for desperate measures, and your brain has an easier time ignoring shame when your dick is hogging the blood.
It felt wrong even typing it, but I knew I wouldn't stop myself. As the certain website containing Craig's lists loaded, I told myself that I was just looking, and that I didn't have to follow through on anything.
Understanding the coded messages in the ads wasn't hard, but sifting through it all was a little tedious. For the most part the ads were either too vague or didn't include any pictures. Most of the ones that did have pictures were either really gross, or contained someone I wasn't attracted to at all.
I adjusted my search parameters to avoid any sex traffic/massage oriented ads. I might be a little gross, but even I have standards. After going through them all and coming up empty I refreshed the page just in case. Lo and behold, there was one new ad at the top of the list.
I clicked on it, and the description was promising but vague. Redhead, in shape, college age girl, looking for a regular arrangement, but no photos. At the bottom of the ad was a link to a Tumblr page.
I clicked it without hesitation, and soon enough my screen was filled with images of a woman hotter than the description had promised. Her face was either blurred or cropped in each photo, but she was definitely a fox.
Most of the photos appeared to be taken at home, with several lingerie and bikini outfit changes, but the last few pics were taken at the beach. I considered reverse image searching them, just to see if they might be stolen pics, when something made me pause.
I was struck with the feeling that I had seen the last few images before, I couldn't place it exactly, but I didn't have a great feeling about it. I searched for the images and found nothing, I don't know if cropping and blurring throws off google, but it seemed like it might.
As a last ditch effort, I opened Facebook and scrolled through my friends, looking for anyone or any friend of friends who might have been triggering my recognition. I didn't know too many redheads, so I was left pondering for a moment at the end of my friend list.
Right there, last in line, was my younger sister Sarah's smiling face.
"There's no way..." I said out loud to no one as I clicked through to her pictures.
I felt dirty specifically searching out my sister's bikini pics, but I had to know.
Almost instantly, I found what I was looking for. They were heavily cropped, and in some cases flipped, but there was no doubt about it, these were definitely my sisters pics linked in that ad.
My rational brain took over for just a moment, and I deliberated whether I thought she might be to kind of girl to start hooking. I knew that stolen pics were relatively common on the internet, and she was definitely hot enough that I could believe that she would be targeted.
Looking back, I think that was the turning point for me. I wasn't into incest before, but when confronted with how hot she looked in the pics combined with the idea of my own sister selling herself for sex, my dick definitely didn't get softer.
Tabbing back to the ad, I had to know for sure. I wasn't even thinking that anything might happen, I just knew that it felt like my duty to figure out exactly what the situation was.
I read her ad again, her coded instructions included an email address. Knowing that I couldn't just use my personal email, I quickly created a burner and fired off a short test message.
I kept it vague, describing myself as not much older than her, in good shape, and well off. I said I was also looking for something regular, and asked her what she was looking for in terms of a donation to start with.
Tabbing back to Facebook, I couldn't stop myself from scrolling through her pics again. I wasn't ready to admit it to myself, but I was as hard as a fucking diamond at the thought of getting to plow her. While paying for sex was dirtier in principle, it somehow lessened the blow of incest in my brain, and allowed me to become fully aware of how hot she was.
Just as I was about to rub one out, I heard an email ping and excitedly tabbed back over. She had sent an equally short reply back, saying that she really just needed a few hundred per week to help cover rent due to her hours being cut at work. She explained that she was new to the sex work world, and she was hoping to meet just one person who could help her out, and that she didn't plan on doing it full time or even for a long time.
My fingers were working before my brain caught up, and I read my email back to myself before replying. This time I was even more brief, I instructed her that I was definitely a good match, and that if she deleted her ad and met me tonight in a public place, I would more than cover her rent for the month.
I was still in semi denial about what I wanted to happen, and I justified it with the public meeting, telling myself that I could definitely just use it to figure out how to proceed if it really was her.
I was kicking myself for not pressing her for more photos, but as I went back to her ad I found the page had since been deleted.
My email pinged again, and I opened it to read her message, starting with a smiley face, explaining that she had just deleted her ad, and that she hoped I was for real. She told my what part of town she was comfortable meeting in, and after googling I confirmed it was only blocks away from Sarah's apartment.
I replied with instructions to meet me in a strip mall parking lot, figuring she would feel safe enough there. It was quiet at night, but there was a gas station and fast food in the parking lot, so there would at least be a few people around. I vaguely described my car, and told her to just come open the passenger door without knocking.
I received no reply, but decided to leave early and drive around for a bit anyway. I was a ball of nervous energy, I couldn't wait to see if she showed up, or if it was even her at all.
I got there early enough to feel like I wasn't being watched, and glued my eyes to the rear view mirror after parking in a dark corner. I regretted not asking her to describe her outfit to me, but soon enough I was distracted by the shape of a woman slowly walking across the parking lot.
She had walked in, maybe too nervous to drive her own car just in case I was a cop, and the thought made me say a quick prayer that I wasn't about to get busted either. I laughed out loud at the thought of praying to god that the woman I had told to meet me for sex was my sister instead of a cop, but quieted as she neared my car.
It was still too dark to tell if it was her for sure, but the pit in my stomach was communicating to my brain that I was about to have the most awkward conversation of my life.
The door opened. She sat down. We both stared at each other.
"Uhhhhhh..." I said stupidly, instantly feeling stupid that I didn't have a game plan.
"What the FUCK," she whispered as loud as she could, her face contorted from anger to horror as the situation dawned on her.
"What the fuck is right," I followed, realizing that I needed to steer the conversation. There was no fucking way I was going to let her know that I recognized her in the ad.
Her mouth hung open, her breathing was heavy. I was able to take in her appearance, she looked hot for sure, but she wasn't dressed like a hooker. Her hair was tied back in a pony tail, she was wearing a crop top and a skirt.
"So, uh, I guess we have a situation here..." I prodded. I wanted to get her talking, hopefully if she engaged with me she'd be less likely to bolt.
She turned to face forward and tucked a strand of red hair behind her ear. She was beautiful.
"I can't believe this," I lied, "what made you want to do something like this?"
"Go fuck yourself," she said quietly without turning, "pervert."
"Hey, chill out," I said softly. I took a chance and reached out to grab her hand.
"Are you ok?" I leaned forward to try and look into her eyes as I spoke, "If you needed help why didn't you just ask?"
She looked at me out of the corner of her eye, but didn't say anything.
"Hey, it's ok," I squeezed her hand while talking, "you can talk to me."
"I need money for rent," her eyes shot back forward, "you read the ad."
"Why didn't you come to me?" I asked. I was legitimately concerned for her, but that didn't make my dick any less hard.
"I don't have to tell you shit, pervert," she continued, "what the fuck are you doing out here?"
I decided to play it relatively straight. The less I lied, I figured, the more convincing I would be.
"Look, I do ok, but I'm in a dry spell. Jerking off just doesn't cut it all the time, and if two people want to help each other out I don't see any problem with it," I explained.
"I'm not judging you," I continued, "clearly I'm in no position to judge anyone." I motioned to my dick, still obviously rock hard.
