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I was at a bar in Chicago. Public bar, pretty busy, but quiet enough to be able to talk to people. I had a few drinks in me and saw a girl sitting at the bar. She was talking to the bartender and didn’t seem like she was with anyone. I sat down and asked for her name. Maria. I asked if I could buy her a drink. She said, “how about I buy you a drink instead?”

By all means. She called the bartender over and said “two shots of tequila, one Long Island, and one rum and coke for him.” We started talking and we got along well. She lives in the city, just got a new job here. Pays well, doesn’t have very many friends here yet. At the end of the night after we finished some more drinks, she asked what I’m doing for the night. She asked if I wanted to come back to her place. We split an Uber

In the back of the Uber, she started kissing on my neck and touching on me. I knew I was gonna get lucky. I had a condom in my wallet. She whispered in my ear, “will you let me take control tonight?” I kissed her and said yeah. I wondered she meant if she could be on top or set the pace. Something like that. She asked me if I had any kinks or something I really want to try. I told her I like to pull hair, be rough, and I’ve wanted to try anal. She told me, “perfect.”

When we got into her apartment, she told me to wait for her to freshen up a little bit. She closed the door to her room. I waited maybe 15 minutes before the door opened up again. Her room was more like a dungeon now. Handcuffs on the bed. Toys laid out. Lube on all the shelves and nightstand. She asked if she could tie me to the bed. I’d never done that before, but I said okay. I laid down on my back. She handcuffed my hands first. She got on top of me and started kissing me. I liked it. I liked not being in control. She went down towards my neck and chest now. She handcuffed my ankles to the bed now. She got off of me now completely. She took off her shirt. She had small boobs. Not my favorite but okay. She then turned around and bent over. She slowly pulled down her pants, showing me her ass. It was big. She was built with a big jiggly ass and wide hips. She told me, “I have a surprise for you and laughed.”

She turned around and had a penis. I gasped. I didn’t know what to say. “You’re a man?” She turned around again, showing me her ass. Her voice was so feminine and sweet. “You’ve never been with a girl like me before?” No. I hadn’t and don’t think I want to. She spanked her own ass and jumped up and down a little bit to move her body around. “I’ll tell you what. If you let me ride you, I’ll face the other way. You won’t have to look at my dick or my face.” I stuttered. “I won’t tell anybody either. I don’t even know your last name. And I’ll probably never even see you again after tonight.” Okay. I wondered I’d try it out once.

She backed up against the bed and got up. She rubbed her ass against me. It made me hard quickly. She grabbed the lube and put it on her asshole. She spread it aside as much as feasible and put my dick against her. I couldn’t move my hands to help her. She slid it in her slowly. This was my first time doing anal. And it was with a sissy. It felt so good. I closed my eyes and imagine it was with a woman. But she felt just as good as I could imagine. I liked it a lot. I asked her if she could face me. She got up and turned towards me. Riding me cowgirl, I could feel her dick on my chest. She leaned towards me and started going faster. I was gonna cum.

She started grinding against me quickly. I was deep in her ass now. “Cum in me.” I came hard. The best orgasm I’ve ever had, and she knew it. She untied me and told me I could stay if I wanted to, but figure out if I want to leave. I decided to stay.

When I woke up the next morning, I didn’t regret it. She still looked pretty, and her body was amazing. She told me, “I put my number in your phone. You have my number but I don’t have yours. Text me if you’re ever curious for some more.” I left. I’m gonna text her again.

NSFW: yes

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