Many years ago, I met this girl at some music event. Full disclosure, I am not a big music guy and was just going there because some mutual friends were playing that night. She was attractive and very energetic; messy blond hair that ran down the length of her shoulders, tight fitting black clothing against a slender frame, and multiple piercings on her ears, belly button, and one in her tongue along with tattoos that ran all the way down her back and along both wrists. She had a skinny build juxtaposed with her tall height.

We all have a type and she wasn't mine, but she was attractive and I was single at the time so I decided why not. We ended up dating for over a year and change. As much as I liked her, I knew she wasn't someone I wanted to be with long term as she was absolutely not the kind of girl you would introduce to your mother. By that I mean, she was constantly between jobs, smoked a ton of weed, and was just in general not someone who had her shit together. This was something she picked up on early and it was a major source of tension. We also fought constantly but the sex kept drawing us back until finally I met someone else and told her it was over.

About 6 months into my new relationship, I get a text from a number I don't recognize; its her. This time she is asking if I can provide her clean urine as she has an upcoming screening for a government job and I was basically the only person she knew who didn't use drugs or smoke weed. I was extremely reluctant to have her back in my orbit. I told her I would be busy and I just didn't feel comfortable with the whole scenario. Then came the following text, "If you help me with this, I will do anything and I do mean ANYTHING!! for you."

Just as the title says, this line is guaranteed to mess with your braincells and it absolutely did. Its not like I wasn't getting sex at the time, but the thought of a woman basically doing anything I wanted overrode all forms of common sense. Even the thought of what the various possibilities were on the menu began to tickle every part of me. And of course, it allowed me to indulge in the worst kinds of fantasies only porn could inspire. So I went for it and sent over a list of expectations. As soon as I sent it, I was feeling pangs of regret. She was an ex girlfriend, not my whore and I worried she would judge me harshly and worse, tell my current gf. But I simply received, "ok", as a reply.

So the next day, I delivered my end of the deal, we found a hotel close by and she delivered her end of it. It probably speaks negatively about me, but some of the highlights included: ATM, Gagging, Swallowing, Rimming, and for her to wear a butt plug the whole car ride to the hotel. All of which she did.

It was one of the best experiences of my life, but also one that filled with absolute terror afterwards if my new girlfriend ever found out.

Edit 1

As requested, the actual events of the sex were a bit of a blur. Despite it being a marathon session; I only remember some of the particulars. I remember being completely spent after it was done; meaning we had done it at least 3-4 times over what turned out to be a 3 hour session.

I do remember trying to gauge what kind of mood she was in; although I was simultaneously fighting back a dizzying haze of overwhelming anticipation. Despite her smelling of weed and cigarettes, I had basically been hard the whole time we drove to the hotel; but also being apprehensive about whether she'd actually go through with it. After all, the last time I saw her had ended rather badly with a lot of yelling and cursing. Her mood, if I had to guess, was a mixture of carnal desire combined with anger at me. Still, she was stoic in her attitude and so I really wasn't sure what would happen. She was even dressed differently. Unlike her usual attire, this time she wore a pink tank top and short jeans as it was a particular hot day. We entered the bedroom and I walked over to the bed and turned to her as she just stood in the entryway. She just looked at me as if to say, "you've requested this, now lead." So I told her to bend over and show me that she had done the plug as I had requested. I remember she unbuttoned her jeans, dropped them down and bent over and pulled down her under ware - showing me this purple butt plug stuck up her ass. I then told her to take off everything and she did so matter of factly.

From there, its a bit of a mishmash of memories. I definitely took it out of her and made her taste it. I then had her undress me, blow me, but especially rim me for a long time. My favorite was lying flat on my back as she kneeled over the bed, spread my cheeks open and she licked and tongued me for a long time. I remember leaving the hotel with sticky saliva still coating everything down there.

Afterwards, we had sex; definitely anal as she was always open with anal. We did everything without condoms as she had an IUD. I made sure to finish every time in her mouth as it always turned me on to have it swallowed (a byproduct of porn no doubt). Before leaving, I had her suck and rim me once more to completion; although I do remember it kind of hurting by that point as her teeth were starting to scrape against the head of my dick.

As soon as it was over and I was back in the car, I remember almost immediately feeling regret and fear about how this might come back to me. I quickly looked over my phone to see no missed calls or texts from my girlfriend; which gave me a sigh of relief. Even still, I was always worried this would come back to haunt me down the road.

Edit 2

I just realized that this post may give the impression that the joy came out of degrading her. In reality, as I mentioned above, she was an ex girlfriend and for all the tough moments we had as a couple, I still respected her as a person and wouldn't have gone through with it if I thought she was having a horrible time. She was also not a weak person by any means and if something was way out of her comfort zone she would have been happy to tell me to go fuck myself.

Edit 3

Even after all that, she either didn't get the job or it didn't last very long afterwards.