Accidentally fucking an ex prostitute [MF], anal, rough

This is a one off story. The time period doesn’t matter.

I’m six feet or so, normal build, not super athletic but in shape. Your average white guy in my 30s (when this occurred).

I met Jill through an online site. It was geared towards kink and sex. Not so much dating. I had zero success before talking to Jill and after. It was a massive sausage fest of a site with more bots probably than women.

Jill was a good 10 years older than me. She was maybe 5’5” and 130 lbs if I was guessing. She didn’t have much of a chest but nice legs and ass. Her profile was pure sex showing off just about everything. She had massive nipples that I assume needed a padded bra to hide.

She was still cute for her age but it was her wild side that seemed interesting.

I contacted her, expecting nothing in return. I was shocked that not only get a response but one without a link to go to or broken English.

We chatted for a couple weeks off and on. She was almost too good to be true. She was super sexual and into anything.

Some of the stuff she said she would do was even a bit much for me.

She lived close to my work and one day she finally came out with, “want to come over for lunch?”

I was trying to play the slow game because honestly she seemed over the top and too much a porn parody. She seemed for real (pictures and other proof). But still unreal.

I decided to go for broke.

“I assume I’m coming over to fuck you good” I responded.

“You better be, want me naked and ready to go?” She replied back.

I was worked up and threw caution to the wind.

Either this was going to be insane mind blowing fun time. Or I’m going to be murdered.

So I drove over around lunch time to see if I was going to be murdered.

She answered the door wearing just a t shirt.

“I thought I’d wear something,” she said.

I walked in to a smoke filled apartment that looked a bit too dirty.

“Nice to meet you,” she said as she grabbed my hand and led me to her bedroom that was surprisingly girly and well kept. It didn’t fit in to the rest of the place.

She pulled her shirt off and fell on the bed.

“Let me see that cock,” she said in what I think was to be a sexy tone.

This felt a bit of an odd interaction.

I stripped and was rock hard. She smiled at my dick and crawled over to me.

She took my cock into her mouth. One. Two little sucks up and down. Then all the way down to my balls. She deep throated me with ease I hadn’t seen since I was a teenager. Holy fuck was it good.

She grabbed my ass and pulled off to the head and back down. Repeating over and over.

I looked at her body and was happy it looked good in person. Not great. I’m not going to pretend a super model was sucking down my dick with ease. Think that chain smoking neighbor you have that has stayed semi fit but looks every bit her age. That was Jill.

She also seemed like she used to be much bigger (turned out she was well over 250 at one point in her life).

I just let her keep sucking me until I felt myself explode. Shit.

She swallowed and moved away and got on her back.

She had a super hairy pussy but a massive clit that stuck out. I rubbed it a bit and went down on her. She moaned and went nuts. Saying how great that felt on her clit. How she was going to cum. Super vocal and I was a bit shocked. It was like shit you hear from a porn.

We weren’t being filmed right?

I backed off after she came hard.

“Fuck me with that cock,” she demanded.

I climbed on top of her and entered what was an amazing pussy. That thing nearly squeezed the life out of me as I closed my eyes shut and went to town.

She smelled of cigarettes and desperation. But I was the one fucking her so what did that make me.

I held off a little and moved her into doggy. She stopped me for a second and pulled out a massive dildo and lube.

Was that for me? I was confused.

“Fuck my ass with this while you fuck me,” she said handing me the toy.

This is new.

So I pushed into her pussy and lubed up the fake cock pushing it into her.

It went in with ease. I moved it in and out as I fucked her pussy. I could feel the dick against my own cock. It was amazing.

I finally plopped the plastic dick out and threw it to the side. I took my cock and aimed for her asshole and pushed in.

She was still tight and went nuts at this point.

“Fuck me! Fuck my ass as hard as you can!” She screamed. I assume her neighbors were used to her.

I never fucked an a woman’s ass harder. I went all out. She reached under herself and rubbed her clit. I held on to her waist and just pounded her for everything I had.

“That’s it. Fuck me. Fuck that shit right out of me,” she yelled.

Wait what.

I kept fucking in almost a trance.

I came hard after several minutes pushing all the way into her ass and unloading my cum.

“Fuck that was amazing,” she said.

I cleaned up and got dressed.

“Don’t be a stranger,” she said as she let me out to go back to work.

We talked a little more online. I needed details on her. It was so surreal.

Turned out she was a sex worker, a bbw prostitute that did just about anything for clients about ten years earlier. She was highly successful at it and I believed her.

She told me stories of what she did and what life was like. It was fascinating shit.

But I also was freaked the hell out by what I did. Met someone who seems to have no issue fucking anyone and fucking them bareback after a quick 5 second introduction.

I got tested (all clean) but I realized that there were limits to what paths I wanted to go down.

Source: reddit.com/r/gonewildstories/comments/c226rg/accidentally_fucking_an_ex_prostitute_mf_anal