Anonymous Confessions

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Have done some pretty questionable things to make some extra cash? From stripping to escorting, Dirty Deeds for Dollars is the category for those who have done what it takes to make a quick buck. Share your stories of financial desperation and the lengths you went to get paid. This category is all about the intersection of money and desire.

Share your secrets and stories of hu$tling for a living..

- Dirty Deeds For Dollars -
Bi-Sexual Female / 29

I was sorry for myself.

I got in trouble in college for providing alcohol to some sixteen year olds who had a wreck and they came looking for me. My father paid a lot of money to a lawyer who negotiated a plea and I was given five years probation and 2000 hours of community work. I dropped out of college because I couldn't do both, the community service rap took all of my time. Working at the Food Bank on Saturdays I met a woman, she was 32 who hit on me and wanted to make out with me. I was lonely and desperate and feeling sorry for myself and I let her kiss me and grab my boobs and suck on my boobs. That is how I became her girlfriend and I ended up having sex with her and moving in with her.

Move forward four years, I was no longer doing community service and I was trying to re-enroll in college but all I could do was get into community college. I was in the dumps and my relationship was in the cellar. My mother's friend, an Architect was without help because of a divorce and my mother told me to talk to him, I could move in with him and in return for room and board I could look after his house. She had talked to him and he agreed on the condition that I stopped seeing 'that woman'.

Once in his house he asked me what I had to trade. I didn't understand and he said if I gave him my pussy he would give me food, if I gave him my pussy he would give me a place to sleep, if I gave him my pussy he would pay for school. I told him to fuck off and went to my grandmothers for the night. She sent me back to him and told me to give him my pussy because that is all I had to trade. Get myself pregnant and stick him with a kid, two can play at the game. With a kid he had to take care of the kid and the mother, that's how the game is played. While I was at it, stick him with two kids, little girls are best but one of each will do.

I went back and gave him pussy and he gave me food and a place to sleep and paid for my school and he got royally pissed when I told him he had made me pregnant. Try any test you want I told him, I have never fucked a guy before, only him and he was the daddy and I was happy for it. You wanted pussy well now you have pussy and as far as I was concerned I was going to make me some kids. He fell for it and I got the best doctor in town, who later confirmed to him that he was the papa and I had me two kids just like my grandmother told me to do, both girls.

I spent a lot of time getting through college, my past is expunged and I am the new Mrs. and he now has three girls with me. I wish I could say that I am in love with him. He is not a lovable man, plus I never know if I don't love him because I may not be made to love a man. But I don't live in a dump and I don't live with that controlling woman who I grew to hate. I turned the tables on him and got myself married to him and used having my girls for it. My grandmother told me to do it and I did it. Plus my girls keep me busy and I am into that. And I am no longer in a dump emotionally. My grandmother swears it is because of the hormones when I got pregnant, maybe she is right.

I guess I am not a nice girl.

1
# 45419 - by Anonymous
    • - Dirty Deeds For Dollars -
    Straight Male / 38

    I know that for any man this is something that would be very embarrassing to admit in public. I am aware that my wife has an ongoing affair with her boss at work. She has an account executive position and lets just say that her boss makes sure that she always gets the best accounts.

    This all started about a year ago, my wife came home telling me that her boss had tried to kiss her and said that he knew that she was married but he still wanted to have sex with her.

    Certainly my first reaction was to act all macho and defensive about what happened but little by little she started telling me how her boss would be able to drastically alter the way the accounts are handled and as a consequence the amount of money that she could make.

    I admit that explanation made me think twice about the situation, I remember I told her "why dont you just go out with him and make him believe something might happen in the future" at the beginning thats what she did but little by little her boss wanted more from her; after a few weeks we had to agree that she was going to let him kiss her in the mouth and grab her a little; eventually the inevitable just came to be, I had to agree that he was going to take her to a hotel room and for that one night, he was going to have his way with her and fuck my wife all over that hotel room.

    It happened that once and I had to be ok with it, but then the following week I had to be ok with a second time too, and then it happened a third time where I wasn't even asked; then one day my wife told me his boss closed the door of his office and fucked her on top of his desk during business hours. He just took her without even asking this time.

    The situation started getting completely out of my control and I would get angry about it, but at the same time my wife started getting those commission checks from her clients and they were four or even five times larger than the checks she was getting before. Every time I thought we had had enough of that situation she would get a check in the mail, we both would look at it, just stayed quiet and just let the situation keep on going.

    Presently I really dont know how often it happens and I really don't want to ask. I just know that when my wife gets home after 7 or 8pm is probably because her boss was horny after work, took her to a hotel around their building and fucked her brains out before letting her come home. My wife has the basic decency when that happens to put her clothes on a separate hamper because Im sure she doesnt want me to see her panties and her clothes full of cum stains from her boss

    Basically it was him the one who put my wife on the pill because she told me that he doesnt like to use condoms and he likes to unload inside of her. He paid for the doctor and he pays for her pills.

    Sometimes I have seen Victoria Secret gift bags in my wife's car. They are probably presents from him with sexy nighties and panties that my wife wears for him when he wants to fuck her. Im sure he wants my wife to look all sexy and provocative before he uses her for his sexual satisfaction.


    The bastard even had the nerve to give my wife a gift certificate for a restaurant so she and I could go and have dinner with his money, I guess as a thank you to me for not causing a big problem when my wife doesnt come home from work because he wants to fuck her

    I feel completely emasculated by all this situation, I dont feel like a man anymore and I have images of my wife and her boss in my mind all the time. I imagine her sucking his cock while he grabs her head and face fucks her or I imagine her spreading her legs for him completely submissive being a whore to him. Its extremely hard to imagine these things but I also completely take my responsibility of everything that has happened, I let it happened and I let it continue until it got completely out of my control.


    We've also gotten used to the lifestyle my wife's salary pays for us. She came home with a new car a few weeks ago and I don't even think she used our money to pay for it. I dont think she wants to give up on that. At this point I even have doubts if shes doing it for the money or because of him. I dont know whats going to happen between us.

    4
    # 45354 - by Anonymous
    - Dirty Deeds For Dollars -
    Straight Male / 23

    My sister who is a couple years older than me was one of the most popular girls at our school.

    I used to charge my classmates money to come over to our house to sniff her underwear whenever she isn't around. They would even pay a bit extra to jerk off and shoot their load on her clothes. I would just throwing them in the washer afterwards and she has never found out.

    0
    # 45300 - by Anonymous
    • - Dirty Deeds For Dollars -
    Bi-Sexual Male / 49

    I was a young lad of 14 and I was always doing odd jobs for money as often as I could to save up for things I wanted like a new bike and things my parents couldn't afford, It wasn't easy but I managed it and had a few regular people that I'd do odd jobs for, One guy in particular would often throw jobs my way, He'd chat to me and always paid a little extra if I did a good job, One day he asked if I wanted to earn more money than usual, I was keen to earn more money so I asked him what I'd have to do he surprised me by saying that he wanted me to model for him in his photography studio that he had in town which I knew about, He said it would be for some catalogue style pictures so he could show potential clients what he could do I'd have to wear a few outfits for the shoot and that's all, I agreed thinking it might be fun and anyway I felt flattered to be thought of model material we arranged a time and day that I would call at his studio the next weekend as I was off school and he usually shut his shop and did the odd wedding photo booking if he had one, I arrived on time that Saturday and he showed me into his large studio he showed me around and showed me the clothes I was to wear mostly jackets T-shirts and jeans there was a changing room that I used and the shoot went really good and he paid me and asked if I'd like to do more work the next Saturday I agreed as it was so easy, The next week he said I'd be modelling swimming trunks mostly speedos I was a bit nervous being almost naked in front of him and his camera but I soon relaxed and posed how he told me to with him positioning me occasionally his hands on my back hips or even a leg so I'd be just right each time his hand stayed a little bit longer, After a while he asked if I would like to earn a lot more but I didn't have to do it if I didn't want to but the money would be good, He said I'd have to pose nude for him so he could sell the pictures to a client who lived abroad and he assured me the photos would not be seen in this country, I thought about it after he told me how much I'd be paid it was more than I earned in a month so I said I would, He told me to get rid of the speedos and he'd shoot there and then, Shyly I dropped them on the floor and stood naked in front of the camera as he told me how to stand and move, He kept touching me moving me this way and that his hands lingering and brushing against my backside and crotch, I started to get hard he smiled as he noticed it and told me it was ok his client liked to see a boy like me excited and he told me to stroke my dick a little while posing my dick got harder as I did it feeling both good and wrong at the same time his touches getting much more bolder eventually stroking my dick himself and touching and squeezing my bum which he photographed a lot both in close up and on all fours my dick and balls too were photographed in close up, He stopped taking photos and started to really play with me using his hands and mouth I was too far gone and horny to stop him I just relaxed and let him do whatever he wanted to, He undressed too and taught me how to suck him his cock wasn't huge or anything special just average and didn't taste bad as. Knelt in front of him sucking away on him he held my head tightly and came quite quickly as I swallowed it as much as I could only a little escaped down my chin, Then he sucked me to my first orgasm with a man, I was payed very well as I was at every session after that I ended up doing full porn shoots with other men and boys my own age and younger some a lot younger but it paid well, I had a steady relationship with him too often sharing his bed after telling my parents I was staying over at friends houses, I even did a couple of porn movies for him including some kinky stuff with me being tied up and spanked that paid a lot of money, I earned my money this way until I turned 16 and he became too ill with cancer to do it anymore, After he died he left me some money.

    0
    # 45274 - by Anonymous
    - Dirty Deeds For Dollars -
    Straight Male / 35

    I was out of work and wasn't having any luck getting a job.

    I went to this one interview at a smaller company and the woman interviewing me, who was also the owner, starts asking me why I wanted the job. The job was a lot below my skill set and experience and she basically wanted to know why I wanted it. I was truthful and told her I wasn't having any luck finding anything. She tells me she thinks I would only work there until I found something else and didn't want to invest any time in training me. She was right but I tried to convince her I would work hard and would be a great employee and really needed the job. She asked how bad I really needed the job and told her really bad. She then asked how badly I really wanted the job. I told her I really wanted it but I didn't know how to prove it to her and if there was a way I would. The next words out of her mouth were for me to get out off all my clothes. I asked if she was serious and she told me if I wanted the job I would.

    I didn't want to do as she asked but given my financial situation I began to undress. There I stood naked in front of her and she looked me over. I was soft and she told be to get it hard. When it was I stopped. She told me to spin around a few times and didn't say much. She looked at me and said I had the job as soon as she watched me please myself. I asked how far she was expecting me to go. She told me as far as I thought I needed to to get the job and added not to worry about any mess I created. I did as she asked and there I was cumming on her floor in her office. Right after she offered me the job and I started work the next day.

    After I started, she called me into her office a few times a week telling me it was to make sure I still wanted and needed the job. I had to fully undress each time and sometimes it was me stroking myself and it had also escalated when other times it was her touching me and stroking me. I was slowly getting used to doing this and one advantage this created was that she mostly called me into her office during working hours which meant I got paid to do this.

    0
    # 45256 - by Anonymous
    • - Dirty Deeds For Dollars -
    Bi-Sexual Male / 20

    In 2018 desperately needing money for travel costs to see my girlfriend, I eventually said yes to a neighbor called Sam. He's a big man (Tall, muscular with a much much larger dick than mine) in more ways than one. And somebody who said I could have more than enough money and more, if I sucked his dick and allowed him to fuck me.

    You can imagine my initial answer. But the closer it got to not going, the more Sam's offer began to seem reasonable. Asking him how much more, he told me if I made it a regular thing, he'd pay me five hundred bucks a month, and offer me a job in his company.

    I did visit my girlfriend that week and we had a good time. However all I could think about the whole time I was with her, was just good it had felt, after our initial fuck, to have Sam's huge cock deep up my asshole. Indeed during the two days before I visited my girlfriend I actually spent most of my time with his cock in my mouth, or up my ass.
    Sam true to his word paid me five hundred bucks. An extra two hundred for going back the next day and on my return offered me the job he said he would.

    I've now worked for Sam for nearly nine months. And each of those months I've continued to be paid for extra hours sexual activities. There isn't a day that goes by I'm not sucking his dick, or having the sixty two year old fuck my ass. The money to him is a drop in the ocean, but his cock to me now, is everything I love and adore sexually.

    When my girlfreind asked me why we were finishing, I told her it was because of the distance. But in reality, it's because I now can't do without a hard thick cock up my young ass.

    2
    # 45255 - by Anonymous
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