Erotic Stories

I let a homeless guy fuck me

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I know it wasn’t the best idea but I wasn’t really thinking at the time. I was with my boyfriend for about a month and I wouldn’t say we were in love but I really did like him and thought we could be together for a while. We had sex once before so when he texted me to come over with a few condoms I didn’t think much of it and made my way there stopping to buy a pack of condoms on the way there. But when I got there my boyfriend has one of his friends there and surprised me with a threesome. I wasn’t comfortable with it and pulled him into the other room to tell him how I felt. He then told me that if I didn’t have the threesome it would really impact our relationship and I ended things right there I wasn’t gonna let him basically force me to do something I didn’t want to. We live in a small town everything is within walking distance so instead of driving to his house I walked which was stupid. It was a shameful walk I felt a lot of regret and sadness. In-between our houses was a park so I decided to sit in the park for a little while to hopefully feel better. It was pretty late around 8:30 pm so the park was empty. There are two benches that sit in the back near some trees that overshadow the whole park. The park is pretty lit up but there wasn’t a light post near the benches so it was sorta dark over there. Still I could see another man sitting, and older, taller black guy and I figured he was homeless, he had bag with a lot of little grocery bags and a bunch of random items surrounded him. As I got closer I also noticed he had a cup in front of him from a close by pizza place, so I took my wallet out and got out a 10 which was the biggest bill I had and gave it to him as I sat on the other bench. He said “Thank you young lady i might be able to eat tonight now.” He laughed and we started talking. He asked a few questions and he was very nice, he asked about my job and told me he use to be a teacher before he got into drugs and his life fell apart and he hasn’t been able to get his life together. He promised me he was clean though which I believed since he didn’t seem strung out or high or anything like that. He seemed like he was just a normal guy, so I decided to tell him about my boyfriend and why I was upset. He listened the whole time and told me not to worry about guys like that, since there’s always better guys out there and eventually I’ll find the one. It made me feel a lot better and I jokingly said “The sex wasn’t even that good so it’s better this way” and we both laughed. He laughed and said my ex had to be white because I wouldn’t be say that if it was a BBC. I laughed but I got a little turned on when he said that tbh, I wasn’t really thinking at that point and I remembered I still had the condoms. I figured I needed to test his theory to make myself feel better and he probably wouldn’t mind fucking a nice petite girl. I asked him “when was the last time you were with a girl?” And he said it had been years, so I pulled the condoms out of my pocket and asked if he wanted to go behind the trees. He chuckled and started packing his things together, once he got it all packed and together he hid it under the benches and I grabbed his hand and lead him to the dark trees. I handed him the condom and as we got behind the trees he quickly pulled his pants down and put it on. I didn’t know what to expect because all the guys I’d been with were very gentle, young guys with not a lot of experience. So I didn’t think it be much, when he slowly slid his dick into my ass I yelped because I didn’t expect him to be that big. It hurt a little at first because my tight asshole had never had something that big in it. After go in and out slowly a few times I figured it wouldn’t be much and it started feeling better and better. Suddenly he grabbed a clump of my hair and pulled my head back suddenly, he then started roughly fucking my ass. I yelled out in delight it felt so good and he was so into it. I didn’t expect him to be so strong, I’m 5’4 115 I know that’s light but he was still able to practically pick me up and use me like I was a sex toy. After only like a minute or two he came pulled out slowly. He thanked me and said he hadn’t felt that good in a while. I was still so horny seeing him take the condom off and his huge cock still so hard. He had to be 8in just by looking at it and I turned around and reached down into my pants pocket and pulled out the second condom. I rubbed my pussy a bit and asked if he wanted some more. Again he quickly took the condom and put it on, it felt like he was even more excited this time than last time because he easily lifted me up by my legs and rested me against the tree and started fucking me. This time it lasted longer than the anal. He never put me down for about 5 minutes he fucked me and I loved every second of it. He kept fucking me for a few second after he came too which felt amazing. After finally putting me down he thanked me once again and I told him I should probably be getting home now. He laughed and agreed and we went our separate ways. I lowkey hope I see him again but i havent seen him in that park in a while.

I’ve done a lot of daring stuff since then that basically sparked my love for fucking strangers in random places at random times. I’ve got a lot of funny and sexy stories I’ll share in the future when I get time

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