The ti[M]e I fucked someone I cat[F]ished.

Throwaway for obvious reasons. This took place last year, starting roughly a month prior to Craigslist shutting down Personals ads.

I was bored, in a relationship that didn’t quite meet my sexual needs, and so one day I went on Craigslist and was getting ready to post an ad. Usually, I used various sexual niches in the titles to make my ads stand out, but this time I decided to be an asshole instead. I went on Reddit, collected a few pics of a monster sized cock off some random subreddit, and posted an ad. I don’t remember exactly what I posted, but it was basically looking for a size queen, someone who wanted to be stretched out. Sure enough, I got a lot of replies. Obviously, many guys who say things like “I know you’re looking for a woman, but if you want a guy, just know I’m available.” The obvious fakes and bots, wanting me to sign up to various sites to see their pictures. But, I also got a lot of real replies. Women who were willing to post a verification pic. I would ask for a picture of their body along with a piece of paper with something random written on it along with the date.

I got a job offer from a car lot owner. Apparently, he was a cuckold and his wife wanted me as an employee for easy hookups. I got offered to be paid to have a cock mold made of my cock, for some sex toy company. I didn’t pursue either, so maybe or probably both fake. Then, I got a reply from this southern belle of a woman. She replied with a few pics, a older blonde, but it was her e-mail that caught my attention where she talked about herself. She was almost twenty years older than myself, but in remarkable shape. I’m pretty sure she was a trophy wife, and her husband had given her a “dead bedroom” for many years by the time we chatted.

Our replies went on for weeks. I learned that she has a submissive personality that her husband never explored. So, I started to give her tasks and become more domineering. She started sending pictures, even though I wasn’t asking for any. When I knew it was time to end the charade, usually I’d just ghost like I had done with all the others, but I felt even more guilty than usual. So I sent her an e-mail apologizing as I had just catfished her for the past few weeks. She was upset, as should be. However, she did write that the reason she was upset was because she just wanted that cock that I had posted pics of.

I was going to let it end there, but a few weeks later, Craigslist no longer allowed Personals ads. That’s when I got another e-mail from, we’ll call her “Pam.” She asked me what I was planning on using now that I couldn’t use Craigslist. We ended up chatting again, me telling her the truth about myself, my relationship, etc. I learned that she was only in my town for a few days out of the week for work, other days she worked back home in another state. So she always had comped hotel rooms.

One particular Sunday night, she messaged me that she had to work an extra few days in town, and her feet have been hurting after walking around all day. My own girlfriend was sitting five feet away from me, lost her in own little world, but I took my phone and replied. “Sounds like you need a massage.” I figured it would be mostly flirting, but then I got her reply. “When?” My heart start racing immediately and I knew I had to make a decision if I was going to cheat that night or not. It didn’t take long though before I pressed send on my phone. “Which hotel and room #?”

It was on at that point, we made plans as I started to get ready. I told my girlfriend that I was going to hang out with some friends, which wasn’t unusual and left. I stopped in at a grocery store and purchased some condoms and headed straight to the hotel. On the elevator up, my nerves were at an all time high. I was mostly worried about if this was some type of retaliation for catfishing her. I started to think about how fast I would need to see behind the door she opens, how quickly I would need to run if there’s some guy lying in wait. I was getting paranoid for sure.

After knocking on her door, she opened it up and invited me in. She let me look around as it was clear how nervous I was while she laid down on the sofa in the living room area of the hotel room. When everything was clear, I felt much more at ease and sat down on the sofa, taking her feet into my hands. I began massaging them, and it was clear she was enjoying the foot rub. We talked for roughly a half hour or longer. My hands continuously rubbing her feet, or rubbing up her legs that were covered by the jeans she was wearing. While continuing to chat normally, I leaned over and slid my hand over her jeans on top of her crotch and pressed down. I watched as her eyes fluttered and her mouth opened, nearly whimpering. The thick fabric of the jeans were too much, so I locked my eyes onto hers as I popped up the buttons and slid my hand down, going beneath her panty.

She was melting before me, as I started to rub her very damp clit back and forth. Within a minute, we were on our way to the bed. Both undressing quickly, as she turned on the radio. She placed a few towels on the bed and laid down. I thought the towels were a bit much, but she does stay at the same hotels often, so maybe she didn’t want the housekeepers to notice. I pulled her to me and immediately started to eat her pussy. Just a few years away from being 50, I was vastly surprised just how great her breasts were. They were still fairly perky, heavenly soft as I groped and squeezed them repeatedly. I ran my hand over her body, over her legs, gliding over her stomach. She was quite fit, her skin silky soft. While we both knew I was dominant, she wanted to take the lead. She wanted to have what she’s been desiring in her life.

I was on my back as she took my cock into her mouth and hungrily started to swallow it. She wanted to impress me with her skills, to show me how much she loves deepthroating. She had been practicing trying to swallow a monster cock during the catfishing days. Then she lifted up, popped my cock out of her mouth and moved forward. She positioned my cock at her pussy and lowered down, taking it all. I remembered the condoms I had, but the feeling of her pussy was too much to say anything. I would find out later on that she weighed the chances of getting an std from myself, but my raw cock was what she wanted.

She rode me hard and fast, as cowgirl is her favorite position. She rubbed her clit as she was grinding back and forth while riding. Apparently, it’s the only way she can get off while penetration is occurring. I took the lead, fucking her doggy, spooning, and missionary with her ankles on my shoulders. I kept whispering how good her pussy felt, how great her tits tasted, which she was clearly enjoying. She was amazingly flexible, likely a cheerleader three decades ago. I was having trouble lasting through everything, needing small breathing breaks here and there to calm myself down.

Eventually, she was back on top, riding away. Louder and louder she was getting, some low grunts coming out of her mouth. My breathing had quickened, and it was clear that my orgasm was nearing.
She started to grind and ride as fast as she could as I held onto her hips. Right as I’m about to cum, she starts to practically scream and all at once, my mind was blown away. As I came, so did she, her pussy convulsing, but what caught me off guard was her squirting. She flooded all over me, and onto the bed. After I came down from my high with her body relaxed on mine, I realized why she laid all those towels down before. We ended up cuddling for a bit, my fingers tracing lines over her body. In the end, I showered with just water to try and reduce any scents on my body. She walked me out, and said to message her if I wanted to give more massages.

Source: reddit.com/r/gonewildstories/comments/e379wp/the_time_i_fucked_someone_i_catfished