This is an account of a true event.... I met with an escort one time. Her advert looked good. She talked about her love of toys and anal. Her photos looked pretty too. So, we met. After normal sex; oral, normal fucking, we had a break and got chatting. She had a cute foreign accent from Romania. We got talking about fantasies and I raised the subject of fisting. It was one of the things she said she enjoyed on her advert. I told her that I enjoyed it too and loved the feelings it gave me. She looked confused. She asked me if I liked to be fisted, and I told her yes. She'd never met a man who liked to be fisted, only women. I asked her if she wanted to do it because I really wanted her to fist me She nodded her head in agreement. I needed to clean up, so I spent 10 minutes in her bathroom, giving myself an enema with the shower head. I went back to her room and sat on the bed. I took the tube of lube from the nightstand and asked her to give me her hand. I held her hand in mine and squirted lube onto the back of her hand. I rubbed it across her hand and between her fingers making sure they were all coated and slick. I could see she was actually quite nervous, so I reassured her, that she was going to make me feel really good. I lay on the bed on my back and spread my legs. I told her to start with one finger, so she slowly pushed one finger into me. It felt divine, feeling her finger worm around inside me. I told her to put another one in me. And she did, stretching my hole. One was nice but two was better. My cock started to stir and twitch. She was getting into it, and she asked me if I wanted her third finger. I just nodded and felt her withdraw her two fingers then press three against my arse until it gave way and accepted all three. It made me audibly gasp in delight and made her smile. I was so turned on and so hard. Looking at this naked, black haired girl, thrusting her fingers into my arse. I couldn't wait any longer. I instructed her to push her whole hand in me! I wanted her fist. She looked apprehensive again, like she was afraid she might hurt me, so I reached forward and pulled her fingers out of me and sat up. All clean. Good. She might have been worried about that too. I showed her how to make a cone with her fingers and tuck her thumb into her palm and told her to push and I reassured her it was going to make me feel so good. I lay back down and she started to push her fingers into me. All four fingers and thumb slid into me. The feeling of her stretching my hole was amazing. When she reached the widest point of her hand she stopped, fearing it wouldn't go any further. I told her to keep pushing. But she was reticent. So, I leaned forward and grabbed her wrist. I asked her if she was ready, as I gripped her wrist tightly and pulled her hand into me. My asshole stretched wide as her knuckles went in. A look of shock on her face and a big groan escaped from my lips, as her fist went deeper, my asshole relaxed around her wrist. Oh my god, it was heaven. I asked her to fuck me with her fist and she complied. Pushing her hand in then pulling it back to the widest point of her hand, but without pulling out any further, then pushing back in again. Over and over she fist-fucked me. My cock was so hard and I wanted to cum so badly. I was about to ask her to suck my cock and stroke it while she fisted me with her other hand, but her free hand was really busy between her own legs, fingering her pussy and rubbing her clit, getting herself off. Fisting me was really turning her on. So, I grabbed my own cock and started stroking it hard and fast. She got excited and said she wanted to see me cum, continuing to thrust her hand in and out of my arse. Once, she pulled her hand back a little too far and it came out past the widest part of her hand. She didn't realise and just thrust her hand forward into me again, stretching my hole. The sensation was out of this world and it sent me over the edge. I started cumming. Spurt after spurt, into the air and landing on my belly. When I stopped cumming, I let go of my cock, breathing hard. My orgasm coursing through me. She leaned forward and started licking my cum off my skin. Within seconds she was panting and moaning as she made herself cum. She still had her hand inside me, but it felt so good. Eventually, she pulled her hand out and collapsed on the bed next to me, breathing as hard as I was. Beads of sweat on her naked breasts, rising and falling fast, as she tried to get her breath back. It was at that point that I felt quite proud that I not only shocked an escort but taught her new tricks. I think she was quite new and wasn't expecting someone like me.