I [F] 19 got paid by my sugardaddy to let a stranger finger my asshole

hey there,

as I described in my sluttyconfessions post, I had a sugardaddy. Td;dr: he loved dirty talk, anal, me loving big dicks (and his cock was HUGE) and turning me into a dirty little slut.

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After meeting a few times in a hotel, where he basically just used me like a fucktoy, he started to give me special requests. I got paid a lot for seeing him but I could earn even more money for doing especially naughty things. This was one of those.

We met at an Café. We first talked a bit and I was really nervous. He then described in detail, what his extra request was. He made very clear goals and steps to get there.

This time, he wanted me to go to a stranger, flirt with him and then take him to the bathroom to get my asshole fingered. This was one of my first extreme requests and I was soooo scared. But at the same time, he would pay me. A lot. And I kind of already started to like being a whore and embracing it. I was still sooo scared but I kind of also liked the idea.

He told me to sit somewhere else alone, drink something and after a while, to ask whoever I wanted to to do it. I ordered a drink and sat down at a table nearby.

Again. I was soooo scared and I couldn’t believe that I was willing to do that. I suspected it already but I put my hands under my skirt and felt that my panties were wet. I took a little bit of time but I nearly finished my drink and found a cute guy. He was probably 27 and looked nice.

After taking my final courage, I went to him. I introduced myself and I felt so shy and stupid. We talked a bit awrkwardly but eventually I told him that I know that it sounds weird, but I want him to finger my asshole in the bathroom. He asked if I’m serious and started to laugh, which I had to do, too. It was extremely awkrward but I assured him that I’m serious. He said yes.

We went to the womens bathroom. We started to make out and he immediately grabbed my ass. First over my skirt, then he pulled it up and grab me even harder. He eventually put my hands against the wall, pulled my skirt even higher and he admired my ass. He whispered how hot I look and that he can’t believe what is happening right now.

He grabbed my asschecks and spread them apart. He admired the view a little more, making sure my ass is spread, until he pulled my thong aside over my buttcheeks. He complimented me, saying that I have a beautiful pussy and that he loves my ass.

One final time, he asked if I’m really sure about this. A final time, I nodded. He slid his fingers across my pussy, making his fingers wet and teasing me a little, until he just rubbed my pussy juice all over my asshole. He did it again, this time pushing his finger in my asshole. It still needed more, so he just licked his fingers and tried again. This time he pushed it in deeper than before.

I still kind of couldn’t believe that I would ever do something like this. I felt so slutty and I loved it. I’ve never done something like this before and here I am now, letting a guy I’ve just met finger my asshole.

I really felt so slutty and I loved it. I pushed my ass against him, taking his now two fingers deeper into my asshole. I started to move, so I kind of rode his fingers while he continued to finger my ass. It hurt but I was imagining being one of those sluts I’ve seen in porn.

We started to go faster and I tried to cum. I’ve never cum from my ass and I don’t know why but I thought I could do it this time. Sadly, I couldn’t. We continued for a little bit but it started to hurt more and more so I asked him to stop. I don’t know why, but in this moment I kind of regretted doing it. He asked for a blowjob in return but I just wanted to leave.

Back in the bar area, I went back to my Sugardaddy. He was sitting there, smiling.

We left afterwards and went to a hotel. I’ve spend the rest of the evenining taking his massive cock into my pussy and ass. I’ve earned a second extra for doing dirty talk, in which I had to repeat that I love being a slut and an anal whore.

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I hope you enjoyed my first extremer requests.

I’ll try to post more confessions in the future.

Source: reddit.com/r/gonewildstories/comments/qsazcd/i_f_19_got_paid_by_my_sugardaddy_to_let_a