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 -
Straight Male / 19

She Found A Boy Toy

Came home for summer vacation from college. I landed a job at this high end golf resort doing building Maintenace. Last month I meant Kathleen. Late 40's early 50's mom. Husband all I can only say he must be rich. One day Kathleen stopped me in the hallway to their apartment and asked how busy I was. I replied Daily repairs are not always the same. Then telling me her husband Robert is out playing golf. And she's bored and wants to fuck. And willing to pay me a week's salary every Wednesday in cash. I replied want time does mommy want me there. She replied well my pussy needs serving today. Then I told my boss I would work Saturdays to have Wednesday afternoons off. He said no problem. Honestly our first fuck was a little strange. Her moaning oh yeah mommy likes this. And remember no pulling out. She has her kinks like having first dibs on sweeping her finger's though the fresh cream pie and licking them clean. Then giving me a taste. Receiving a blow job without asking. First female ever to rub their clit while fucking. Man, life is good.

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# 64800 - by Keith
    • - Dirty Deeds For Dollars -
    Straight Male / 20

    Making Money

    It is not dirty deeds for dollars . It is for UK pounds . Every Saturday morning we would meet up for coffee . Me and 3 pals , with 5 girls . When they had finished their coffee . The girls went shopping . We hung round the city centre until it was time to go to the football match . We always had a meal in the same cafe. Before going to the match .

    One Saturday there was a woman with the girls . She worked with one of the girls . This girl had befriended her at work . In the weeks before she was invited to join us . The girl told us about her . When she was not at work . She had spent all her time with her parents . Looking after them and their large house . She did not have any friends . She never went out . She was always smart . But her clothes were old fashioned . Her parents had both died she had inherited their money and the house . She sold the house and bought a flat in a new block . In the city centre . There was a new coffee shop in the basement . We started to use it . The girls took her out to buy more modern clothes and make up . Showing her how to use it . They did this in her new flat . The next time i saw her . I nearly didn't recognise her . She was so different with her make up . She had a nice face and a nice body . A solid body but not fat . She was attractive . We talked about her . The girls were fascinated by the thought that she was 35 and never had sex . They wanted to know what she was like . The first time she had sex . Planning how they could find out . The idea was put forward that one of us pals should be her first . It was treated as a joke . Then the following week they were talking about it . Saying which of us they thought should be the one . The idea was becoming more of a challenge . They each offered to pay £20 to the one of us who did it . There were no volunteers . They asked if we would let them make us draw straws . To see who it would be . Not wanting to look like wimps . We agreed to do it . Lucky me i got the short straw . No backing out . It was decided that when she was with us . I should talk to her like a friend . I did this by asking her about herself and things that she liked . What she was starting to enjoy . She enjoyed meeting up with us . She liked us being her friends . She seemed to warm to me . I was warming to her . I liked her . I liked talking to her . The girls were asking when it would be . I told them it would be the next week . I wanted my pals and the girls to make excuses to have to leave us . Leaving me with her . They did this . I talked to her about her flat . Asking what it was like . She asked if i would like to see it . We went up in the lift . Her flat was on the fifth floor . She showed me round it . I had expected old fashion furniture . The carpets and furniture were the latest designs . Nothing looked cheap . It had 2 large bedrooms and a large modern bathroom . With a bath and a walk in shower . It had a large kitchen diner . With the latest gadgets . A lounge with a large tv . She took me on to the balcony . It looked over the city centre . When she was showing me her bedroom . I pulled her on to the bed and kissed her . She put her arms round my neck and kissed me . Being honest she was a rubbish kisser . She did not know how to kiss . I had sort of expected this . She had never had any practice . She was wearing a loose fitting dress . I put my hand behind her back to pull the zip down . Then i pulled it off her shoulders and exposed her boobs . I was getting an erection . I was getting aroused . I lifted her bra up to look at her breasts . I kissed them and sucked her nipples . All the time i was thinking about her being a 35 year old virgin . I pulled her dress of . Leaving her in her knickers . I took her bra off . I wanted to see her pussy . I pulled her knickers of . And pushed her legs apart . Looking at her virgin pussy . I kissed it and licked it . She lay there not moving . Then when she had her orgasm . She was noisy and her arms were waving about . I didn't know if it was her first orgasm . When it had finished i asked her . She told me that it was her first . She had never felt like that . I wanted to fuck her . When i was pushing my cock in to her pussy . Something was stopping me . I gave a push . She gave a little squeal and i was in . I fucked her . She was making noises of enjoyment . I was soon cumming . Knowing that i was her first fuck and i had taken her 35 year old virginity . I knew that i did not want the money from the bet . I liked her . I wanted to keep seeing her . I realised that i could make her pregnant . I asked her to see her doctor . Getting him to prescribe the pill for her . She started taking the pill . Every weekend i was with her from Saturday morning to Sunday night . Sleeping with her Saturday night .

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    # 64699 - by Georgio
    - Dirty Deeds For Dollars -
    Gay Male / 19

    I Made Some Homeless Man Cry From Riding Him So Good

    I’m 5’4 with a brown caramel skin tone, curly bangs, wide hips, big lips, thick thighs, and a plump ass. A lot of people say I look like chel from el doarado but as a femboy and I dont blame them. I’ve been built to get pounded genetically speaking. Well I did when some homeless guy asked to fuck me for 35$. I was about 16 and just came back from partying at one of my friends house walking to my car so I decided to take him up on this offer. I’ve never did this before so he pulled out his massive already erect cock and told me to suck it. His cock was absolutely massive, the biggest one I’ve ever seen to this day and about 10-12 inches. Who knew some hairy homeless man was packing so much, I almost thought he was a pornstar in disguise. I got on my knees into the alley way and started to suck his cock. I’ve sucked things before and I also have no fag reflex so I was able to deepthroat his entire cock down my throat. After 1 minute he started squirming as I was sucking the life out of him and told me to get on top of him so I can ride him. I said okay and angled myself into a good position, slid his cock in my ass, and instantly felt pleasure to my entire body. Some people say their first anal experience was terrible but mines was absolutely amazing. There was no pain and I was able to take his entire cock balls deep either my ass. And not inly that but the feeling of him being fully inside me was unbelievable and I started to bounce on his 10 inch cock right in that alley way. After 2 minutes if this he started squirming again and told me he was about to cum. I rode him harder and he cum inside of ne. Despite that, i continue to ride him even harder and he began to start crying because he had already came and was done. I wasn’t done though and I was so close to finishing. It felt like I was on edge for about 3 more minutes and during that time he started to cry. They were being muffled every time I bounced on him and when I finally came and took his dick out, he was asleep. I made a homeless man with a 10 inch squirm from head and faint from my ass. I now wonder if I should do porn as I definitely have the face and body. I could be dominating in the industry after what I did that day!

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    # 64643 - by Makeusquirm
    • - Dirty Deeds For Dollars -
    Bi-Sexual Male / 69

    My Whole Life As Far Back As I Can Remember I've Been Sexual.

    As a boy even before puberty I was jacking and sucking the older boys dicks to be in their club,tree house, fort in the woods etc.Making money or getting something I wanted was a natural progression..As long as I can remember sex was always around me.I've done fathers,grand fathers,mothers,grandmothers,little girls,little boys.I'm always horny to this day and I'm almost 70...I 'm the proverbial if it feels good do it often. I'll suck and fuck anything,everything.I've broken most of the Taboo's...You name it I bet I've tried it...I sniffed and made love my mothers panties for a long time.I'd cum in her chewed slobbered on panty crotch and place them on top of the laundry hamper so she would find them...I was always watching dad smack her butt,groping her.She'd be walking by,he'd grab her ,pull her on his lap and slide his hand up her shorts leg.You could see from her body language his finger was penetrating her.Right there in front of me and my little sister dad would finger fuck her.She was a petite blonde sex bomb 90-100 lbs,tiny little titties..

    Skip forward few years I'm a freshman in high school fucking everything that walks, sucking coaches dick and even fucking my algebra teacher..
    Dads out of town with work.I come home from a football game date a bit buzzed,moms on the couch in her robe passed out drunk. I'm horny having been heavy petting a cheer leader but no sex...Shaking mom,saying her name.No response so of course I open her robe to see she'd naked underneath...I can still see it in my mind as if it were yesterday...Her pussy shaved bare except a little patch above her clit. As I pushed her legs apart her clit stuck up erect like a little dick bugging to be touched,sucked. No shame,no fear or thought of consequences I fucked her. She was way wet,hot, willing,used to being fucked....After I came I scooped her up carrying her to bed.All the while she never woke up

    Next morning I woke her up fucking her from behind spooning her..Of course she panicked when she realized her son was fucking her and not dad... While she protested I emptied my balls in her...
    She often protested while responding to my firm forceful touch. She loved the way I touched her,having my way with her,giving her uncontrollable squirting orgasms... Even after dad was home I'd grope her, sneak quickies in her when dad was outside doing chores or out in the garage.You'd be surprised where you can get in a quick fuck. After awhile she got into it,she really had no choice....After dad died I bought her sexy outfits and would take her out in public showing her off as my girl..We had some wild sex..
    She died as parents do at 63. The booze had a lot to do with it...

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    # 64559 - by OB
    - Dirty Deeds For Dollars -
    Straight Female / 22

    Sugar Baby

    I have always considered being a sugar baby, but never know which sites is the best?? anyone have any tips or recs??

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    # 64513 - by Deadkayz
    • - Dirty Deeds For Dollars -
    Straight Male / 30

    Wife For Sex

    I want my wife to go out and have sex with people and let me watch or at least takes videos and show me.

    1
    # 64464 - by Chriskk1982
    100 of 40,940 Confessions Displayed.

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