Not Embarrass Of My Past
This happened years back when I was still a teen. I was going into my last year of high school and got into a fight with my parents. My step dad kicks me out. So here I was homeless, no job, very little options to turn to. I had a boyfriend, but he was starting his first year of college, still living at home. His parents tried to help me best they could, but I didn’t want to burden them with my problem. I managed to get onto social assistance and got a place in a rooming house. A small little room, shared bathrooms with the other 12-14 rooms in the place. At least I had my own fridge and stove to make food with. But I was scared out of my mind. I was the only female living there at the time. There was a guy that lived there that was kind of like the maintenance person. He was across the hall from me. He was almost three times my age (47 yr old), but he was nice to me and did everything he could to make me feel welcome. And the rooming house owner lived across the street in a B&B he owned. Not like I ever saw anyone stay there. This was a pretty shitty area of town. The bar district was nearby, lots of places with junkies and prostitutes in the area. So for a short 5’1” tall, chubby girl like me, I was scared to death to live there. I was constantly getting propositioned for sex. It always pissed me off.
So after a little bit, money was getting tight. I was stressed out because social assistance and the hours at the job I got at a store weren’t helping me make ends meet. One evening I’m coming home and I had one guy offer to pay me for a blowjob. And another guy ask me how much to fuck me up the ass. When I got home, I ran into my buddy from across the hall. And we started talking and I was complaining about these two guys. But I said that the money sure did sound good at times that it can make it tempting. What he said shocked me. “If you’re ever looking to spread your legs to make a few bucks, I want to be the first. I wanna know what those tits are like.” I laughed at it, not to sure if he was serious. And let it go at that.
Another few more weeks went by, bills needed to be paid, I was super stressed. I was coming home on evening, I remember it was raining pretty heavily that night. I got in and it was pretty late. I decided to have a shower. As I was going to the bathroom, I noticed the light and tv were on in his room. By the time I took my bathrobe and slippers off and jumped into the shower I was kind of wrestling with the idea of taking him up on his offer. I was in the shower way longer than normal. So I said to myself if he’s still awake, do it. I got back and noticed he was still up. I was kind of frozen. I stood there forever trying to get up the courage to knock. I kept thinking, this is cheating on your bf, you’re not a slut, this guy is way older than you. But the whole idea of picking up some cash was to great. I lightly knocked on his door and it opens. He was like hi, what’s up? I asked if I could come in for a minute. And he lets me in and closes the door behind me. He said to me “what can I do for you?” I then asked if he was serious about the offer. Which of course he said what offer. For a sec I was like “fuck”. Then he said the only offer I remember making was if you were looking to make a few bucks. I said yeah, that one. He pulls out some cash out of his wallet, I can’t remember how much but it was well over $100, puts it on the table. I take one look at the cash and open up my bathroom. I was super shy about my body. I was a smaller bbw at the time, and he was only the second guy to see me naked. But the shyness was gone fast, when he went, “oh fuck baby, those tits are nice, and a hairy pussy, this is well worth it.” He walked over, grabbed a hold of my boobs, was kissing my body and rubbing my clit. He only had on boxers and somewhere in there they dropped to the floor. He threw me down on his bed. We opened my legs and started eating me out. I’m looking at him thinking to myself, “this is so wrong. I’m weeks away from turning 17 and he’s 47.” But damn I was enjoying it way to much. He went and got a condom. Came back and flipped me onto my stomach. He put the condom on, raised my ass up in the air. I feel him rubbing my pussy a little, then shoved his cock right into it. I swear I screamed. Lol. He was flipping me around in different positions, pounding me soft, than hard. Eventually he cummed, I thought it was going to come out of my mouth, it was that intense. I grabbed the money, kissed him on the cheek and thanked him and ran across the hall totally nude. I fell on my bed thinking what did I just do. But also thinking that was fun. A funny part of it was the next day, another guy that lived next to him asked me if I had heard the noise across the hall. I said no. The guy said he was getting it on with some girl pretty hard. lol
A few nights later there was a knock at my door, this time it was him asking if I’d give him a bj. So I invited him in and did the job. The next day I ran into the owner of the rooming house outside his B&B. He stopped me and said, “do me a favor. I don’t care if you whore yourself out in my building. Just keep it under the radar so we don’t have any problems.” I was like, what do you mean? I’m not doing anything. He then said, trust me, you wouldn’t be the first girl here to do that. And I understand it’s sometimes the only way to make money. So I said, okay, I’ll do my best. But I hadn’t planned to make this a regular thing. But when I started to walk away, he said “come and see me one evening if you want to work off any of your rent.” So I was like that sounds like a good idea. So I went that evening to talk. He was even older, mid 50s I would guess. So we worked something out. He wasn’t as good in bed. But I figured if all it took was me fucking him a few times a month to live rent free, it was worth it.
After a few weeks I couldn’t look my bf in the eyes. I felt guilty. So I broke it off with him. I actually do regret that now. But the money was good. I didn’t plan to add anymore people to the mix. But I started doing other guys in the rooming house if I felt comfortable with them. When I started branching out of the house, I started to question my choice. Especially when I started meeting people on craigslist. I had enough money saved. I moved out and went back to school. And stopped doing this for good. I don’t regret what I did too much. I got confident in my body and great in the sack. I estimate I was with over 25 guys in that time and tons of stories to share from my slut days. :)
