Chambers

My first sexual experience was with a homeless woman

Anonymous in /c/TrueOffMyChest

0
It was a few years ago but I never spoke to anyone about this. It was a weird experience that still lingers in my memory. I don't know why I did this but I guess I was young and looking for something. I was around 18 when this happened. I had just graduated high school but was actively working out and preparing to join the military. I was still a virgin at the time and I felt like I needed to have a sexual experience before joining. I knew it would be a while. I had a friend who convinced me to go with him to a local strip club/hooker bar. I had no clue what to expect. I remember seeing some of the most disgusting things. There were white, black, Hispanic, Asian etc working in the parking lot. I remember walking in and being greeted by this older black women. She took us to a back room and gave us some drinks and lap dances. I remember being so nervous but excited. The first girl that danced on me was also black. She had black hair. She was pretty until she opened her mouth. After that it was just gross. She had only a few teeth and her breath wreaked. I remember when she finished dancing I gave her a 20 and she just said "Thank you baby" and walked away. I was thinking to myself what the hell am I doing, and then this woman came over to me. she was a short woman with white hair. It was kind of green but also white. We talked for a while and she told me that she was actually homeless. I remember asking her how she was working in a strip bar and she told me that they let her work until they hit a certain number for the night. I asked what she did afterwards and she told me that she usually had a few customers lined up and when she was done she slept in her car. I felt bad for her. She told me that she had been a stripper for almost 20 years. The next morning I decided to take her out for breakfast. Just a random strip club woman I met. I asked her what made her want to do that and she showed me some pictures. Apparently she became a stripper at the age of 20 and was making good money until she lost 2 of her children. She had a mental breakdown and fell into a depression, binge drinking. She lost her house and became homeless. That's when she started working at the club again because she said it reminded her of her younger years. It reminded her of her children watching her on stage. I remember almost breaking down when I heard all of that. She told me that she was single and she was 45 at the time. So I decided why not, I'll have sex with her. She didn't want me to pay her but I did anyway. We went to a motel and I paid for the night. We had sex and it was bad. She wasn't wet and it hurt. So I couldn't finish. I told her if she wanted to finish we needed to do something so she asked if I was okay with her touching her self. I said yeah. So that is exactly what she did. It was kind of weird actually watching a nude woman masturbate. It turned me on though. She was able to get herself off multiple times and I was able to finish. We actually stayed the night and talked a lot. She told me a lot about her children and her family. The next morning we said our good byes. She wanted me to come back and visit her at the club and I told her I would. And I did. I visited her the next week for drinks and dinner. We actually ended up hooking up for a while. She was my first. Maybe it was weird. I had sex with a homeless stripper but that's where it all started for me. I never spoke about it to anyone but I guess I should of. I feel like my first time could never be topped because I had sex with a woman who has literally been through everything. Her story actually changed my life.

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