The dirtiest I’ve ever had

I started chatting online with this really kinky crossdresser in another city as I was headed there for a few days. She told me that she had one fantasy - to be picked up off the street as if she was a prostitute but that if I did that she’d do anything I wanted.
I’d had some things I’d wanted to do for a while but this really seemed like someone that would be up for it so I told her the plan and she loved it.
So at 8pm I drove up to her on the arranged street and she hopped in the car. She was a bit older than me, not convincing but dressed like a massive slut, I thought that from behind she’d look amazing. I gave her the money and I drove away and she immediately reached over and started pressing her hand into my crotch. When we got to my hotel we got in the lift from the car park basement and thankfully nobody saw us. That fulfilled her fantasy so now it was the Me Show.
We sat down and had a few beers and I told her how amazing her outfit was and how I’d been waiting for this for weeks now. She said she got such a rush from dressing in public and getting picked up on the street. Eventually she asked if I was ready and I said fuck yes and led her into the bathroom where the supplies were waiting. I stood her in front of me and lifted her miniskirt and pulled her panties off. Out flopped a monster uncut cock below the skirt line and I couldn’t help myself but put it in my mouth for a few precious moments. She’d clearly been aroused for a long time and I could taste the sweet gooey precum. Mmmm I said before turning her around. I got the bulb enema, pre filled with milk and lubed the end up. I asked her to bend over slightly and then I just gently pushed it up into her ass hole. She gave out a girly shriek. I said this will be cold, hang on and then I squirted the milk all the way into her while she giggled. I pulled the enema out and a little bit of milk was around her hole so I delicately removed it with my tongue, making sure I’d left none behind.

Now it’s time to make a fucken milkshake, I told her and I slid straight into her. There was no resistance whatsoever, either because she was expert at taking cocks or because she’d just had the enema up her and was relaxed. I started going hard and kept telling her she was just a dirty street slut, a fucking skank, that I was going to put my seed in her asshole. As I fucked her hard I kept telling her to try and squirt the milk out but she couldn’t. I ended up finishing really quickly, I was so aroused, squirting a huge load up into her along with the milk. I pulled out, exhilarated and ready for what was next. We walked into the shower and I got down on my knees and she bent over in front of me a pulled her cheeks apart. Her ass hole was inches from my face and I just watched it move. It moved out like something was about to come out and then in again, then all of a sudden pffffffssshhhtt. The milk shot out all over my face and chest, covering me. It took two or three blasts to get it all out and then she turned around and started slobbering all over my cock, which gradually went limp over the next few minutes. She was limp too, having jerked herself off whilst I’d fucked her.
The I curled into a ball at the bottom of the shower, covered with milk and she stood over me and pointed her cock at me. It started as a slow dribble but eventually got going and she hosed all the milk off me with her piss.

I just lay there in raptures at the bottom of the shower whilst she showered herself and then left. It was a good 20 minutes before I got up and turned the water back on to shower myself. It was the first sexual experience that taught me that it is not just about simple penetration, but everything around it.