I was probably around 24 or 25 when I met Anna(not her real name). She was home visiting her family and wanted to go out with her brother and some of our friends. I had zero expectations of hooking up with her since she was my good friends sister. It was a group of about five of us. We were out at a bar in Chicago. She was about 5 feet five, and had an incredible body. She was very pale with jet black hair. She lived in Birmingham, England. She had moved there when she finished college and ended up staying. She was married, but had gotten separated from her husband so she was visiting her family.

I had never hooked up with anybody that looked like her.

We started having drinks at the bar and she started talking to me a bit. Normal conversation, asking questions about me since she had heard about me from her brother. We were just talking normally for a while but she kept getting closer and would stare right into my eyes. She had an amazingly hot look. I thought it was a bit odd because I still wasn’t thinking that we were going to leave together. At a certain point I was sitting down and she was right next to me when she said “Want know something? I’ve been thinking about fucking you for the last 45 minutes.” She actually put her hand on my cock under the table. I was immediately rockhard. She looked down and said “oh, that feels nice.” And she smiled. I still wasn’t sure if I should do it because it was my friends sister, but just then he noticed we were talking and said “I think my sister likes you”

I took that as him telling me he was fine if we left together, so I whispered in her ear that we should leave. She grabbed her coat and walked out the door and said follow me.

I snuck out without telling anybody. We got a cab and as soon as we got in the cab, she pulled my dick out and started sucking it. Right in the backseat with the cab driver in front of us. I saw him slightly adjust his mirror, but he didn’t say a word. I just let her do it. I told him to take us to a hotel and he drove about 10 minutes. She had on a black skirt and I started fingering her from behind while she sucked my dick.

I haven’t thought about that in a while, but man, that was really really hot in the cab.

When we got in the hotel room, it was insane. She ripped my clothes off and just started sucking my dick again on the bed. I have never been with such a dirty talker. She said some dirty shit that night.

She let me do basically whatever I wanted. We had sex in the bed, we had sex in the shower, in every position imaginable. She even let me fuck her in the ass. The first time I came after she was riding me on the bed, but after about 10 minutes I was ready to go again. We went in the shower and cleaned up, and I fucked her in the shower too. I remember standing in the tub with the shower hitting me on the head while I drilled her pussy from behind. When we got back in the bed, that’s when she let me fuck her ass. She was unbelievable. The things that came out of her mouth were just filthy. “I want to suck your cock after you pull out of my asshole!” So loud too.

I remember she asked me to pull out right before I came and I took the condom off and just came all over her face. She licked my dick clean after that. After that it was like 4 am and I had to get home. Before we got dressed we got horny again but my dick was done. She asked me to tongue her asshole before we got dressed. I stuck my tongue in her while while she rubbed her clit. As she had her orgasm she groaned and literally said “fuck I love your tongue up my ass!” I’m shuttering here thinking about her. After that she kissed me with her tongue all over my mouth and we said goodbye.

I saw her one other time after that at his wedding, we didn’t fuck but she did take me in the corner and jerk me off for a bit. We had planned on me going up to her room later that night but I don’t remember what happened. We couldn’t hook up that night. That was the last time I saw her.

The weird thing was my buddy didn’t really care. We are still close friends and occasionally he will laugh about how I banged his sister. I’ve never told him the details though. I’ve actually never told anyone.

I totally forgot one part. This was really hot. When she was riding me, she started to choke me. Like to the point of me getting a little bit worried. Lol. She actually slapped me in the face a couple of times too. Hard. It was fucking hot. When she was slapping me she was riding me hard and she kept saying “you like this don’t you? “ Never had that happened before or since actually. She was calling herself a whore and she just kept telling me to fuck her harder. My dick was sore for two days after that night.

100% true story. Feel free to message me with any questions or more details. I will respond. I hope you enjoyed reading.