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812 stories found
Decided to try my luckI've read stories on this website and others and being a failure at the dating game, decided to test my chances. Not sure if luck would follow me, I (33) started looking for woman who were down and out and living rough. First problem there were none, our community isn't big enough. Only a small city and authorities keep the street clear of the down and outs. So, I would look for women having a hard time financially, there were some not many and none suited me. Finally realizing I was being too s... reading time 3 mingenreStraightwritten on
2024-03-31of
Totally SatisfiedDecided to enjoy myselfDivorced in November 2023 and only 43, after alimony and child support payments I was okay financially. But decided to expand my income stream without my ex-wife and her lawyers finding out. I started an online business using my business address rear entrance as the business location and a post office box for all the mail. I already had another post office box for primary income source and also started online bank account for the online business. Once it was up and running, it fairly okay straig... reading time 3 mingenre
Straightwritten on
2026-03-10of
Horny no longerMade A DealI'm rich all inherited, but I don't show my wealth I live simply and indulge myself. So, when my neighbor died after a single vehicle accident leaving his wife (47) and daughter (22) struggling with his funeral and hospital bills. I (34) made them an offer to improve their lives. In a nutshell it was working for me as live-in housekeeper and maid. Of course, I paid off their debts in return for sexual favors from both. No more rent to pay or working several low paid jobs each. Worked well, but I... reading time 1 mingenre
Straightwritten on
2026-07-21of
DealmakerAunt's NeedMy Aunt, 34, was widowed 2 years earlier, and she had no children. Very well off financially, she wanted at least one child, maybe more, and did not want to find another husband, as she already had too many money-hungry men trying to marry her. I'm her only nephew and had just finished college, just passing at the bottom of my class. No real great future career on offer. But my aunt hired me as her chauffeur/bodyguard; I'm quite good at the martial arts. A lot better than my college score on oth... reading time 1 mingenre
Incestwritten on
2026-06-21of
Chauffeur NephewSome people think I'm a WizardI seem quiet, an unassuming, but I'm the complete opposite. I'm arrogant and smart enough to know not to show that side of me. I'm also rich all inherited and I don't work. So, I came up with perfect setup to serve my needs. In the early 2000's I like many others watched the Harry Potter Movies. That gave me my idea for my lifestyle setup, I would pretend to be a Wizard. I heard people talking about how great it would be to have powers like Harry Potter. I'd money and with that you can do things... reading time 3 mingenre
Straightwritten on
2024-01-15of
WizardThank God for the InternetNot the porn sites, but the idiot sites like X. Where people post the most stupid stuff and so many idiots believe it. Conspiracy theories abound, all you have to do is play to their fears and you can drain them of their money. I found a perfect way to live well and not work by exploiting their fears. My target is rich widows, ones that believe bad omens or magic. Most are regular church goers; some are into the occult. As I'm over 50, I keep to my age group and once I find a probable target I f... reading time 1 mingenre
Straightwritten on
2025-01-18of
Conspiracy UserI decided to give it a tryI (38 born in 1979) single in no relationships or likely to be in one anytime soon. I masturbate to get off or hire a hooker and it left me feeling a bit worthless. I read a story about a man picking up a woman living on the streets giving her a better life and gained a lover. I at first thought it a fantasy, but I hadn't notice women living on the streets. But I hadn't looked or took notice of anyone who was down and out as people say about them. I finally started looking a little harder and fo... reading time 4 mingenre
Straightwritten on
2024-01-20of
The ChancerCar accidentI (41) lived alone and had only one nearby house, I've a classic car 1963 Corvette Stingray. It's my pride and joy and I left it in my driveway after returning from a drive as I needed to use the toilet urgently. It was well off the road and as I was returning to park it in my garage, I heard a crashing noise. Getting outside I saw my neighbor 20 had hit my car, she had pressed the gas instead of the brake. Mostly likely due to the high heel shoes she was wearing, luckily for me it was glancing ... reading time 3 mingenre
Straightwritten on
2024-11-08of
Lucky for meHelping MyselfAt 34 my career was doing very well, my personal relationships not well at all. I became aware of a work colleague 47 who had lost her husband early 2024 (cancer) not doing great financially. Hospital and funeral debt, she has a handicapped daughter who requires a walking frame to walk slowly if not a wheelchair. I happened to overhear her talking to her daughter who worked whatever job she could get. I was on the other side of a room divider coping at the printer. I heard her tell her daughter ... reading time 4 mingenre
Straightwritten on
2025-05-13of
Happy to HelpPerfect I'm no ladies man, but I do okay as I have the will and means to succeed. I don't pick out the best women available, I go after the ones that are weak. By weak I mean they are just getting by and anything go wrong they are in big trouble. I'm the manager of a business that employs these women and so I exploit those who interest me. I prefer mature women to the younger ones, as they can't get pregnant. Which would cause me trouble, I see a woman who interests me and start to find everything I can... reading time 4 mingenre
Dominationwritten on
2022-06-21of
Alfred no settled downSister wanted it so badI (23) live at home with my parents and the younger of my two sisters, my other sister is the oldest and is married and has 2 children. I'm not a lady's man and rarely even get a date and have paid for every fuck I've had. Till Last April that was, but my younger sister 20 wanted so much to buy new shoes and go see her favorite artist in concert. Not able to afford either, she decided to ask me for a loan. Our parents wouldn't loan her that amount for such things, so she didn't ask them. She did... reading time 5 mingenre
Incestwritten on
2024-09-29of
Horny Sister fucking mechanicBack in 2015I was living quietly alone in my home and got new neighbors, a recently married couple. I was 34 at the time and worked from home and quite well off due to inheritance from my late parents. I wasn't dating or in any relationship, used a local lady 47 to get my rocks off. She cleaned my house and needed extra money and we came to a mutual beneficial arrangement. The newlywed couple were loud neighbors, well he was always shouting. He 35 had a high stress job and the slightest thing set him off, s... reading time 3 mingenre
Straightwritten on
2024-07-19of
Accidental HusbandThree SistersI'm Randall 34 married with children to be born in the next couple of weeks. I was single until last December when I married Lydia 29 oldest of 3 sisters and got her 2 sisters Nancy 25 and Maria 22 as dowry (wives also). Their mother Ana 45 widow and with no male relatives to provide dowry for any of the sisters, thought they wouldn't ever be able marry. I met Lydia in June 2019 while working in there country and we got on very well. But unable to proceed with relationship due to lack of dowry. ... reading time 3 mingenre
Straightwritten on
2021-09-09of
RandallDeal of DealsI'm a pretty boring person, not risk taker and the quiet loner type. I 31 have one advantage I'm rather well off. Make my money investing and with no great risk to it. So, when I was asked to back a way-out idea, I said No. But a man was so desperate enough to make an unusual offer putting his wife 46 up as his collateral for the duration of the loan. Meaning she would cook, clean and let fuck her until he paid me back. Which he did on time, and I made some money and got sex. She wasn't a center... reading time 3 mingenre
Straightwritten on
2023-07-03of
Deal MakerChange of LifeDivorced and free and clear as they say, no alimony or child support to pay. My ex-wife got half of everything and as she also has a good career that was it. Our children look after themselves have their own jobs. So, I bought an apartment 2bedroom all I need, as a partner in my chosen career workplace I'm well off financially. Not wanting to remarry or even have relationships at the time this all started. But being single again and okay looking for a 53-year-old, I attracted the attention of si... reading time 3 mingenre
Straightwritten on
2026-02-26of
I got HornySeeing the CountryI'm 29 and single with itchy feet, I travel the country working here and there to get by. I'm no great looker, but am well built, fit and tall 6'3" and attach the attention of people as I travel. I can turn my hand to most jobs using my skills I learnt growing up. I can do fencing, plumbing, carpentry and electrical and can fix a car or tractor if no computer work is involved and manual labor (pick and shovel) is another thing I do it keeps me fit. So, I do attach interest of women, singles, mar... reading time 1 mingenre
Straightwritten on
2024-06-17of
Willing TravellerMy MotherMy mother a widow wanted grandchildren and I being her only child had to provide those grandchildren. Problem I wasn't a lady's man in any sense of the description and not that much to look at either. Skinny or weedy is a good description of me, I was into sports and had a long bout of illness growing up that left me skinny. But I was strong and just didn't look like it, I also done well at sports. But wouldn't ever make the big time, but I had fun and that's the most important part having fun. ... reading time 3 mingenre
Straightwritten on
2023-10-18of
Mommies BoySore Balls UpdateI got hit in the balls by a hoe left lying in the grass by my brother John. My mother Judy saw the incident and came to see if I was okay and one thing led to another and we started fucking. Judy marriage ended with the sudden death of Kevin in a car accident, I wasn't very close to him. Neither I or John were all that close, John took a job offer from his girlfriends father and move to the next town. I finished my hitch and then returned home to Judy and straight into bed with her again. She wa... reading time 1 mingenre
Incestwritten on
2022-06-16of
Lionel GHousekeeperHaving recently moved to a new city I (40) was alone no close friends as yet. My job came with an apartment, and it was too big for me to keep as I was alone and usually very busy. So, I decided to hire a housekeeper, easier said than done it turned out. Housekeepers were in very short supply; most being deported by the government. But there was a silver lining. The DOGE was sacking Federal workers, and I had an enquiry from a recently sacked mature woman (54). She was really desperate as she wa... reading time 1 mingenre
Straightwritten on
2025-10-14of
ChancerHelping a colleagueThis all started in 2009. I (27) got a promotion and transfer that came with it, well offer due to inheritance and trust fund. It was my first time living away from family, in another state. I duly bought a house 3lge bedrooms 1bathroom with separate garage. Like in my former hometown I used hookers for sex, I'd no interest the dating ritual, I just wanted a fuck. Then one day at working a colleague (51) was upset her rent was doubled almost, it was a way of getting the tenants to vacate quickly... reading time 5 mingenre
Straightwritten on
2025-01-21of
Horny smartassLoner no moreThere's always one as the saying goes and, in my small town, I'm that one. I lived alone and at the end of the street and had only two neighbors. No houses behind my home or across the street. My neighbors were a mother and daughter living together and working low paid jobs to get by. I worked mostly from home via the internet, there isn't that much to do locally anyway. I have to go to the city at least once a month sometimes twice, but once I usually get away with. Anyway, I was 34 single no r... reading time 3 mingenre
Straightwritten on
2023-06-03of
Loner to BreederInherited a businessI inherited a business from my only uncle brother of my late mother, as his only living relative I got everything. I'd done business related courses at college including advanced computing, so I knew what I was required to do. I wasn't set for life as they say but would be comfortable financially. I only had 7 employees all in their fifties, 5 men and 2 women. The women ran the office and the men the warehouse and deliveries. My first action on taking over was to install a computer system myself... reading time 3 mingenre
Straightwritten on
2026-03-01of
Benefitting BossFailure to SuccessMy love life was hookers and lucky for me I'm loaded, an only child born just before my mother turned 40. She had lot of trouble with my birth, so I was her first and last. My father was 12 years older than her and had stroke 2 years later and died, a lifetime of smoking, drinking and drugs was the cause. So, when my mother died at 62 (car accident) I was all that was left of my family no grandparents, aunts, uncles or cousins. None listed anyway, quite well off and felt awkward in personal rela... reading time 3 mingenre
Straightwritten on
2024-05-11of
Former FailureThe Woman across the StreetI was between relationships and noticed the new neighbor across the street was a good-looking woman. Around same age as me, I noticed no husband/boyfriend over the next few days. Of course, I decided to meet her. So, using the welcome to the neighborhood as a cover I duly met her. I offered to help if she needed any help and left shortly after arriving not wanting to overstay my welcome. As she had bought the house and it had some minor problems, she took me up on my offer to help. That allowed ... reading time 1 mingenre
Straightwritten on
2023-07-19of
Hopeful NeighborI like to fuck Mature womenI'm Peter 23 single university student, I come from a well off family. But my sex life isn't great, I do date regularly. But I'm more attracted to mature women than ones my own age. I've always had a thing for older women and spied on my grandmother undressing to get myself off. Never would be game enough to approach her myself, as she is a very strong willed person. But away from home and not short on cash, I found mature women doing it hard and I pick the ones that interest me and make them an... reading time 1 mingenre
Fetishwritten on
2022-07-28of
Peter A D