50 Men Talk About The Time They Dated Sugar Mamas And MILFs
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Cataloged in Romance

50 Men Talk About The Time They Dated Sugar Mamas And MILFs

These people from Ask Reddit will make you want to date an older woman.

1. Yoga studio owner/my yoga instructor had me quit my job, move in with her, and go to all her classes for almost two years. She spoiled me and paid for everything but my self-esteem suffered greatly. Was kinda fun being on two year vacation but hard to explain the gap on my resume…

2. I briefly dated a milf and quite frankly it was great, she would expect me once a week with a fridge full of beer, home made food and dessert and all the sex I could want. Dumped her to give my ex another chance, it failed. Well to be fair, there were other reasons (milf got too attached and I didn’t want to hurt her) but that was the main one.

3. I’ve had multiple “sugar mommas” and thought it was the best, for awhile at least. I would have died if it wasn’t for one of my sugar mommas. When I moved out to college, I had no money for food or anything else. Sugar momma bought me food, took me out to eat everyday, let me stay with her, took me to do fun stuff, and all I had to do was have sex with her. That girl probably spent thousands of dollars on me.

Unfortunately, I was not attracted to her AT ALL, and she wasn’t a bad person. I started to feel bad that I didn’t actually care about her and came to the conclusion that it’s a bad idea to use people for money/food, so I split up with her.

I’m not really proud of this story, but I was hungry and couldn’t afford food.

4. When I was 20 I had a stint where I was unemployed. To start getting benefits I had to attend a job agency. Saw my agency contact at the local night club one weekend. Hooked up, took her home to my house. Next meeting she used agency money to buy me a new suit, 2 shirts, 2 ties and about $600 in fuel cards.

Basically a one night stand turned pretty profitable.

5. Woman I lost my virginity to. She was 8 years older than me and managed one of the best salons in the city. She paid for everything. Little boy toy me was just along to ride.

6. I was in university full time, not working, living in a room that had no door just a curtain… she was a full time nurse, paid for everything. Insisted on buying me gifts all the time, paid for meals and movies, paid for my car to be fixed… was sweet until she left me for her ex. Don’t care now, though no one has treated me that well since.

7. My brother, 19, met a 30+ year old on tinder in his college town. She worked for ESPN and other companies that owned major music festivals across the country. They would hook up whenever and she would send him gift-cards for food or uber, one time he asked her for tickets to Buku Music Festival in New Orleans. She said of course! And put me, him and my friend on the will call list. They ended up being GA+ tickets so we had perks!

8. The mother of one of the kids I was a counselor for at a summer day camp. She would show up late then bring me gift cards to apologize. She would hang out and flirt with me while I closed everything up. Near the end of the summer she told me as a thank you I should come to the high end men’s clothing store she runs and get fitted for a nice suit. The first day after camp ended I stopped in. She picked me out a suit and a few shirts and ties and had me try it all on. Then we we ended up having sex in store and I left with a bunch of pretty clothes.

It turned into about a once a week thing where she would send a text about me having clothes to pick up at the store. I would come down and see her at the store we would have sex and I’d leave with some kind of clothes.

9. So this happened when I was 18. I met a woman at a club. She was a 43 y/o milf but very in shape. She owned a couple of local restaurants. Would always make me come over and cook dinner. Sometimes even give me the keys to her older BMW to get around in. She took me to Vegas a couple times. Sex was good. It was nice for a while but she was very controlling. I had to be at her place within a certain time after I got off work (which was basically the commute time plus five minutes). I certainly wasn’t allowed to date anyone else. I got tired of it and quit.

10. I was homeless when I was 18, and I hit up a dating site and found a deaf chick 10 years older than me, and she became very infatuated with me. I got a place to live, food, money, and Pokémon games from her. I cut her off physically when I got a girlfriend later in the year, but she still kept paying for my stuff. I feel genuinely awful about how much I took advantage of the situation.

11. I seem to have a problem with this. When I was 18 I dated this 40yo that was basically independently wealthy from her divorce. Her daughter who was a year or two older than me was into me, but her mom blew her out of the water in the looks dept. To make a long story short she basically took care of me for 2 years. We spent both winters at her ski-in/out condo having sex and snowboarding. I moved on to another woman that was in her mid 30’s, same thing. I’m now in my late 30’s seeing someone in her late 40’s. I’ll just say she takes great care of me.

12. In my early 20’s I met an older woman around mid 40’s in a bar. She was drinking alone and I stood by her to order a drink. She leaned over and gave me all kinds of compliments about my body. I said thanks and that she looked great too. She gave me her business card (realtor) and told me to text her around 2am. I did. She rolled up to my place in a super nice Benz. Woke up and she was gone. Next weekend she texted me an address and to be there at 8pm and to clear my entire weekend for her. I did. She had a really nice 8 bed room house.

She was WILD, taught me a thing or two and let me explore all kinds of shit I didn’t even know I was interested in. The next weekend, same thing. I showed up and she had so much stuff for me. Really nice high end clothes and shoes. She also bought all kinds of kinky toys for me to use on her too. She made me into a half ass dom and I would tied her up and do just about anything I wanted to. We had a good time.

Then she fell off the face of the Earth. I don’t regret it one bit. She was really nice and spoiled the shit out of me. She made me food and would bring it to me while I was in bed. Massaged my body damn near every day. She would sleep in a different room and between the sexual times we would have long lengthy conversations about anything and everything.

13. I did once visit a guy who had a sugar momma, a friend of the girl I was dating at the time. He was this average looking 20 year old stoner kid who was living in a nice house in the city. His sugar momma was paying for him to go to community college.

14. A rebound girl I was seeing at the time offered to buy me a plane ticket to visit her in Hawaii on her vacation.

15. This happened in Tokyo around 5 or 6 years ago. Met a client at work when I was 26 or 27, she was 32 or 33. She was REALLY cute, VERY smart and educated, and we got on very well together. She was a bit of a train-geek, she liked riding trains. Fairly common in Japan but rare for a woman, she had a lot of cute quirks like that. She could tell you the make and model of every pantograph on every train in operation in Japan.

Anyone who knows Japanese politics has heard her name before. I didn’t know who she was when we first met but my boss later on told me to treat her like a VIP at all times.

Anyway our work project wrapped up and we decided to go out for a bite at a nearby restaurant. She tells me she needs help preparing for an interview at a very famous company for a very unique role that they would essentially be creating just for her. I tell her I’d be happy to help her with it – I didn’t have any ulterior motives, I genuinely liked her and wanted her to succeed. We met up again to do the interview prep, and one more final practice after that.

She invited me to play darts with her after we’d finished since she apparently enjoyed darts and I’d never played before. We went out to a darts bar in the early evening, and somehow we ended up playing a game where the loser of the game had to drink tequila shots. She mopped the floor with me but we both started doing shots until well past the last trains home.

Eventually we wound up going to an internet cafe to spend the rest of the night, but things progressed pretty quickly – she got touchy feely and we decided to get out of there and go to a hotel together. And so began our relationship.

She turned out to be richer than god. She would buy all kinds of stuff for me, would never let me pay for dates even though I was making very good money for my age, wanted to take me on all kinds of trips around Asia. She bought me some very nice watches and clothes which I still have and cherish to this day. She had a Benz and an Aston Martin and some other cars just lying around in her parking spaces in the middle of Tokyo.

Probably would have married her if it weren’t for some complications with her marital status – I found out about that after a few weeks of dating. It was a bit of a tragedy really. It turned out she was in a terrible, loveless marriage and had a young child. I found out about that way after we’d already been going out a while. At first it made me uncomfortable to be in that situation, but I started to understand that she was trapped in it and due to societal pressure she had no real way of divorcing. Neither of them wanted to continue their marriage and both of them were seeing other people, but due to their very high profile in the Japanese media a divorce was out of the question.

We ended up breaking up when we realized having a kid together would cause irreversible damage to her political career and that a divorce to marry a white guy would be the end for her professionally. That really sucked but it was the truth. She was the best girlfriend I’ve ever had – if I’d met her 3 years earlier I’m sure my life would have been completely different now. Not for the money, could not care less about that. I’ve never met someone I connected with so well. Really the one that got away..

16. Went on a date with a girl visiting from NY. Didn’t see the point as I was looking for a relationship. Had a good time, wasn’t doing well at the time, so she flew me out to New York and paid for everything, Airbnb, so forth. She flew back a few times, became clear she was emotionally unbalanced. Sweet girl and I wish her the best.

17. Had a huge crush on my friend’s hippy mom for years when I was a teen. She knew. Some things you can’t just hide all the time (boners!). Went to their house one day after work, but my friend wasn’t home. Ended up secretly hooking up with his mom for a few months. It wasn’t a financial sugar mama, but all the sex and pot a teenager could hope for.

18. I live in a frat house and the brothers come over and have dinner semi frequently. Formal things on Sunday nights. The president always comes in variously very very well tailored interestingly patterned suits. He’s 23 and his sugar mama likes seeming him dressed up certain ways and he likes the suits.

19. Hooked up with my roommate’s MILFy friend, ended up dating for a year and a half. She lived in a big, brand new house with her estranged husband and kid. They had separate bedrooms, he knew about me and wasn’t really happy about it but she controlled him and he wasn’t a problem. She came from money and had a good job, and the husband made good money, but couldn’t manage it, so she got all of his money, on top of her own, and partied pretty hard. I never had to pay for ANYTHING beyond my rent.

20. When I was 22 I had a friend who’s mom was into me and I liked her she was tatted and 16 years older me, her son was 19. Well we started to flirt and eventually started to hook up. Well any time we went out she drove, bought the food or drinks, and any thing I wanted. She was an amazing fuck like she changed my life but she told me she loved me after 6 months and I was out.

21. In my early 20’s, I met someone online. She was good looking and had a nice personality. She was in her late 30s We fell for each other, and I found out that she is rich AF, when she started gifting me whatever I spoke about. I tried to stop that since I felt like she was buying me out and because I truly loved her. I even tried to propose, but she had 2 kids and she was certain that she will lose custody if she marries someone. I checked that with my friend who is an attorney of law. When I saw that I had no future with her, I convinced her to forgive her Ex-husband “father of her kids” and remarry him!!!! I didn’t want to see her growing up alone! Back to the main point, when I calculated the estimated value of the items and cash she gifted me, it mounted over 60,000 Saudi Riyals ~16000 $

22. I was seeing an older American girl (27 yo, 3 kids, married but separated) who offered me (20 yo at the time, European, single, Uni student) a job in her family’s business in Miami, a lot of cash and benefits 10 years ago. She was super cute too, and the sex was good, but I just couldn’t say yes as I was focused on graduating from University which I did. She was super nice, we are still in touch. She remarried and had 2 more kids after me.

23. I was an intern at HQ for a company when I was around 19 and the lady I interned for was super hot. She was dating another guy, but he was kind of a dork and she didn’t like him much, not EXACTLY sure why she stayed with him but that’s beside the point.

The sex was incredible, she really liked doing it at the office which was hot. Lost my virginity to her, which was fantastic. She had a thing for doing things that were “so wrong.” She would take me out for fancy lunches, always $$$, and would cute them as a work expense to justify spending the time with me. She encouraged me to follow my passion for the arts and funded my first album. It didn’t do well, but she loved that there was a song about us on there.

Later she even got a wicked good boob job and let me fool around with those. She got the surgery to get back with her boyfriend, but told me she didn’t mind if I took advantage of it too.

She kinda went crazy later, which lead to her being fired and I left the company soon after. She ended up moving in to her boyfriend’s condo. She wanted to keep our “thing” going, but between her mental breakdown and the fact that I didn’t want us to get caught going at it in the boyfriend’s place, I figured it was best that we ended it.

I hear that she has a kid now and is managing a hospital or something. I truly wish her well and sometimes wonder if she still thinks of me.

24. 19 years between us. We met when her car broke down and I stopped to help her. She invited me along to her friend’s house. She took me home and seduced me. I moved in a few weeks later.

That was 10 years ago.

25. The summer I was 21 I danced at a club and then went home with a woman who was 31 at the time. She wasn’t exactly a sugar mama in that she didn’t have any money herself – she was a teacher and a single mom – but she knew tons of people and she got invited to some really nice parties and events.

That summer was a blast. She taught me a ton about cooking, we had killer sex, she had fun slummin’ it with my friends, I got to be her arm candy at all kinds of parties in really nice houses, some private rooms at clubs, art show after parties, things like that.

We never really made it anything official. We always joked that I was her pool boy and she was my caught cougar. As the school year started we both settled into different routines and drifted apart a bit.

To this day the most amicable split I’ve ever had in a relationship that lasted longer than a month.

26. I once did a BDSM scene with two older women. One was about twice my age. I don’t know how old the other one was.

27. I live in Japan and date a fair few women in their mid- to late-thirties. The last one bought me a Switch.

28. Was mechanic for ~60 employee company, dated the ceo for around 6 months. Don’t think I’ve been that financially stable my whole life; Barely spent a penny!

29. Back when I spent a ton of time on MMOs (Guild Wars 2 specifically) I joined a guild and became friendly w everyone. Met a married couple – a bit older and they both had I think 10+ years on me from what they told me.

Eventually they broke up because the guy was apparently being a controlling asshole to her. I kinda saw it since his humor in our guild chat was asshole-y… anyway, she was the only one that logged in at 3am one night and we just ended up talking more than usual and getting closer. I was actually just trying to comfort her, but since I was also recently single we were kind of just drawn to each other.

She visited my city for a week and asked me to show her around to the best places for us to spend our time together. I didn’t mind paying and suggested stuff within my price range (college student at the time), but she ended up convincing me to try some (more expensive) things I never considered doing since she’d be covering everything while telling me not to worry, and thanking me for being there for her to keep her from feeling a little less lonely. It felt really weird because I didn’t want to feel like a gold digger lol but she eventually convinced me that it was fine.

Of course we had a lot of sex throughout the week, in a really nice suite at a really nice hotel. Ate at restaurants way out of my price range, went clubbing with our own table, it was definitely an eventful week. We already agreed on nothing being serious – we were just enjoying being in the moment and it was totally fine.

She flew back, life went on, eventually we got caught up in our own lives and stopped playing online as much, which meant our communication started winding down as well. It’s actually been years since we’ve last spoken, but I hope she’s doing well.

30. Was 19 almost 20 at the time. Seen this milf that moved in to the house next door. My best friend came over and we were outside smoking some bud; We seen her walk into the house from work and I told him “man, I would bang her.” Hour later she came out of the house and started talking to us by the fence.

We’re all talking and having a good time, then all of a sudden my buddy says “coldshaadow told me something about you”. If looks could kill, I would of murdered him. She looked over at me and said: “Oh really? What did you say about me?”. I thought about it for a second and decided to just say fuck it and see what happens. I told her I wanted to bang her.

Later that night all three of us were drinking, my buddy got too drunk and passed out in our garden come to find that out the next morning. She told me to come into her house and we fucked. That’s the start of how I ended up dating a milf for nearly 5 years.

31. Not as in depth or freaky as others but I had an older woman buy me a gift card for a year of Netflix. When you’re in your mid 20s and don’t have a lot of money it was nice.

32. Met her when I was 22. She worked two shifts a week at work, and suggested going to a movie. I was flattered and jumped at the chance. Afterwards we went to her apartment and had the most awesome sex of my young life. Next day, more of the same. Within a week, she suggested I move some of my stuff in; no need to pay rent, her mom and dad took care of that. And the car payments. And credit card bills. Eventually I found out her family owned thousands of acres of farmland, three radio stations, and a television station. After a few weeks, the sex got less and less, and she began spending more time out with her girlfriends. Guys would come by too; guys wearing colors and riding Harleys. Slowly the truth started coming out: she was gay, the women were her rich girlfriends and drug clients, the bikers were her drug dealers. She needed a man to live with her to keep her rich extremely conservative family from guessing that she liked women and cutting her off from her money. Feeling like I’d been lied to and gaslighted, I moved out after a month and ghosted her.

33. When I was 18 my manager at work had a thing for me, she was 32. She kept buying me lunch from the mexican joint nearby which I thought was funny considering we worked at a grocery store. She flirted an awful lot and straight up asked me to come by her place after work. We smoked weed and watched tv and had lots of sex. Always told my parents I was going to a friends. My mom even met her at the store and asked me later if I liked her. Made me choke a little.

34. Ex constantly bought me food and would give me money if I wanted beer or weed, but would then leave the beer and weed knowing I would drink or smoke it all.

She only ever came to my apartment for sex and would then leave when I couldn’t get it up again.

Her mom would drop off 3-4 bags of groceries every week. She bought me my 2nd car ever and paid for my college classes and helped me get my life on track really.

It ended pretty quick when I told her I thought I was in love with her.

35. A while back I posted in a couple subreddits here for meet ups, and a woman actually messaged me. We connected pretty well, and found out her job took her around the US. She also was in a poly relationship, and just liked having guy friends everywhere, so I just became another one of her boyfriends.

When we started talking it was about 2-3 weeks away from my birthday and I had told her it was coming up soon. She wanted to get me something for it, but I had felt uncomfortable telling her my address. Finally she convinced me, and about a week later, she sent me an incredible care package. It was 2 brand new games, a new hoodie, some comics, and a funko pop. It was a lot to spend on me even though we hadn’t known each other that well.

36. My friend earns really good money and works for a government organization in a poor country, so she barely needs to spend anything. She’s 33 and just likes younger guys, maybe around 21-25. She said it’s because she enjoys the power aspect of it and she doesn’t mind paying them or spoiling them because for her, it’s a power play. Works for her.

37. I’m currently in an FWB-type thing with an older woman (I’m 23, she’s 37) with some “sugar momma” elements to it (mostly that she buys me nice dinners and drinks and I give her a good time in bed playing a switch). We met on Bumble; she says she wasn’t originally looking at guys my age but her friend messed with the age thing without telling her and she matched with me.

She’s a professor/researcher and I’m a grad student (not her student, but in a similar field at the same university so we have a lot in common). She didn’t actually realize I was that much younger until we’d already been texting for awhile and had a date planned, but she went through with it anyway and the sexual tension was there from the start. I was pretty nervous the first time, but she has some dominant tendencies (especially in bed) so I think she found it cute. We fucked 4 times that night and haven’t slowed down much since. We aren’t exclusive or anything; she goes out with other guys her age and I go out with other girls my age. She actually encourages it; she even likes hearing me talk about whenever I get laid with a younger girl.

It’s kind of a crazy whirlwind thing, especially since I was a virgin less than a year ago, but it’s fun. Would highly recommend. Although I feel like if I ever get famous or run for office or anything it’s going to get found out somehow and scandalize my entire extended family to death.

38. I went to a bar one time and this cougar kept ordering pitchers of beer for me. One thing led to another and I went home to her place. Woke up the following morning to find out she was an E-7 and I was a E-4. (Fast forward to later in the relationship) She told me that she wanted to get engaged before she left for her next duty station. I agreed so we went to a jewelry store. She picked out a ring and asked me if I wanted an engagement present too. I picked out a fancy watch and she paid for everything. Two days later she changed her mind about the engagement and decided she wanted to be single.

At least I got to keep the watch.

39. Met a 30 year old widow on Xbox when I was 19. She said she played Xbox to pass the day because she was financially set for life when her husband passed and wanted to make some Xbox friends. We start playing more and more until I couldn’t keep up because my controller and headset broke. She asked for my address and after a week, I got a brand new controller and headset. I couldn’t thank her enough and asked what I could do in return, to which she replied to just keep playing with her.

Over the next few years, she occasionally buys me new games when they came out and even a few Collectors Editions if I wanted them. Eventually, we drifted apart because I couldn’t find time play with my school and work schedule.

I still miss her and occasionally try and find her online again but can’t remember her gamertag or Facebook. She will always be one of my best gaming buddies I’ve ever had

40. I met an older MILF when I was 27 ( she was 43 ), and I think it was really more of a “boy toy” situation, though we were still friends. She would basically take me all around the state on her trips as a sales rep. when I had the days off from my own job, and we’d stay at hotels and just fuck half the night. Then we’d wake up, fuck again, and be on our way. It lasted for just over a year, and honestly, I was just so spoiled by her in terms of sex. She loved to fuck out in nature, and before it ended, we had fucked in three National Parks. We even had a thing where we’d impersonate The Count with “TWO National Parks! AH AH AH!”, and then laugh like idiots.

41. Former teacher 10 years later.

42. This happened to me a couple years ago. I was back home from college on a break and matched with this girl on Tinder. She seemed pretty cool and we texted for about 3 days then decided to meet up and get some sushi. She came over to my house first and parked in front of my house (my moms house) for like 15 minutes and texted me she was too shy to come in. Eventually she walked up. We got sushi then went back to my place. One thing led to another and pretty soon we were doing the horizontal hokey pokey in my bedroom. She stayed the night and we hung out and got breakfast the next morning. She said she had to go to the mall to return some stuff and asked if I wanted to tag along. I said sure why not. He go to the mall and she’s returning some clothes or something so I’m just looking around the store. I find this sick ass Patagonia jacket and I was checking it out. When she was done she saw me checking it out and asked if I wanted it. I said hell yea but it’s like 250 bucks and she said she’d buy it for me. I just laughed. She took it off the rack and went to the counter. I thought she was just really committed to the bit until she pulls out a Manila folder FUCKING FULL of $100 bills. My jaw dropped and probably made a weird sound. She just looked at me and winked. We left the mall and I had my dope ass jacket all bagged up. I asked her about the money and she just said “don’t worry about it.” We has been talking for a couple days and I knew a lot about her at this point and knew she worked a close-to minimum wage job. I just let it go.

She drives me back to my house and before I get out of the car she says hold on and pulls out the folder. I ask what she’s doing and she just throws $600 into my bag. I felt weird and tried to give it back. She said don’t worry about it I have a bunch. She opened up her purse and pulled out like 6 or 7 of these Manila folders. Eventually she convinced me to keep the money and I was just like fuck it, I’m a hooker now I guess.

I go back to school and she goes back to hers. Over the next few months she would randomly drop any where from $100-$500 in my Venmo every week or so. We continued texting and she just kept buying me shit. If I mentioned being hungry she’d order a pizza or something for me and my roommates. If I mentioned I needed/wanted ANYTHING I could expect to see it in an Amazon box on my porch a couple days later. Shit was tight.

I go back home again on my next break and decide we should meet up again. This time we skipped the sushi and went straight to doing the ole bippity-boppity-boo. Again, things go great. She says the night and we watch a movie the next morning. She eventually decides its time to leave and puts 10 $100 bills on my coffee table. At this point I know she won’t take no for an answer so I just take the loot and say thanks. She drives off and waves bye to me. Everything seemed normal. A few hours pass and I go to text her but it doesn’t go through. Weird but what ever. More time passes but my texts still won’t go through. I tried to message her on Snapchat and it looks like she deleted me or blocked me or something. Turns out she blocked me on every form of social media. I was pretty confused. I just played it cool and tried not be a weirdo and like call her a bunch or anything.

Break ends and I go back to school again. Still haven’t heard a word from this chick. Then at like 2am on night I get a call from a blocked number. Shocker: It’s her. I asked her what was going on and she just shushed me. She was whispering but not like sexy whispering. She sounded super serious and a little scared even. She just told me that I can’t tell anyone about our interaction together, her name, or anything. She even asked me to delete pictures she sent me of her. I ask what the hell is going on and she just tells me she has to go. I hung up the phone and never heard from her again. Still got the Patagonia though!

43. I got a free personal training session at Equinox gym. This woman working out there must have been working the same routine I was doing because during the session, we ran into each other nonstop at the same benches/machines, joking about it a ton eventually then chatting her up the end of the session. Super pretty and fit 41 year old, incredibly intelligent, with her own private practice doing sex therapy. We seemed to click. I’m 26.

After my session, the trainer/salespeople allowed me to stay and keep working out on my own. Then this therapist lady makes her way back to me prob since the trainer was gone and we continue talking and exchange numbers to get together sometime, I figure what the hell may as well try for this one.

No more than 5 replies into our first text conversation she straight up tells me I’m cute and she’s always busy, so she’s looking for a casual hookup relationship with me. I tell her oh how convenient I’m in the same boat. Luckily she lives pretty close by too. So I’ve been going to hers about once a week for the last two months or so just to have sex and hang out. Oh, and she’s also really into the zodiac and tarot cards(?), and she likes to analyze me and eventually wants to “read my cards.” Idk whatever, small price to pay and tbh it actually is pretty interesting and sorta sexy when she talks about it.

Now this wasn’t a sugar mama type relationship at first, but we started going out to dinner just for fun, and even though it’s not date-y really, she’s paid for everything since. Then it evolved into buying me some nice things—nothing too personal like clothes, but she’s gotten me some nice bottles of wine, scotch, a candle she liked, ya know nice gift type things. Well this week these gifts just went a step further, she’s going to Barbados in February and after jokingly saying I’d love to go, she booked me a ticket because, well, she says she felt like it. I’m also an avid surfer so she wants me to surf all morning while she sleeps in then basically bang her on different parts of the island. I’m dropping $0.

She’s adamant about not having a relationship outside of a casual one though, for numerous reasons it isn’t for her, and having spent enough time with her I think she’s genuine and I believe her. She definitely likes to spend money on me but not in frivolous ways like more clear-cut sugar mamas. Still, I think the situation fits well enough to comment about. Who knows, maybe she’ll start funding my business?

44. My mom, who works as a massage therapist, told me her boss (42) at her spa thought I (19) at the time) was hot when my mom showed her pictures of me. Ended up getting an add on Facebook from her, and she told me to come down to the downtown spa where she worked at during her lunch break. Got an hour massage, crazy sex on the table, $50 and a Chipotle burrito.

45. I had a girl give me an iMac because she liked me and we played video games together. We had never really met up until that point. She was sad my laptop was dying so she gave me her old iMac. Most expensive and nicest gift I was ever given. Felt like a Sugar Mama.

46. Fucked a milf, next morning she made me breakfast and cut my hair.

47. I was at a dive bar and this lady comes in, wearing yoga pants, and a tank/sports bra. It was a Tuesday night. She was beautiful. Looked like a hot suburban mom early-mid 40’s. Had no idea what she was doing there. We got to chatting and it turns out she was in the middle of a divorce and had been moving out of their house all day.

We exchange numbers and I go to her house later that night. Door opens and it’s on without introduction. Through the night and later the next day, she keeps making comments about how she can’t believe she’s with such a younger guy. I look young for my age so I assume that she misunderstands and I say,”you keep saying that… I don’t think I’m as young as you think” and she asked how old I was… I told her 33 and she said that’s what she thought… she was 55. I was totally shocked but also thought it was pretty cool.

Over the next year, we had an ongoing relationship. She never cared or got jealous about who I was dating or seeing. We would even talk about sex with other people while we made love. Which was pretty hot… because neither of us were possessive and it was about mutual enjoyment. She was very adventurous sexually and I felt I could open up about anything and be truly open with her, without judgement.

We would go out to restaurants and she would always pay. She paid for us to take one small trip for a week together out of town which was awesome.

She always talked about how she had an older man set her up in business , when she was young, and how she’d like to do the same for me. And we would talk about plans for what that would look like.

She even suggested I move into her spare bedroom and be roommates. Saying she wouldn’t be jealous if I brought a girl home. I thought that was a bit too complicated and would work only in theory so I respectfully declined.

I moved off and she found someone her own age and we talk less and less all the time, but I keep her updated on my life, I think of her fondly and often, and tell her I love her. I consider her a very special woman to me, and she still inspires me.

48. When I was 19 I dated a 35 year old lady. She was not super rich herself but her dad was and she was very much a daddy’s girl.

Anyway her dad was a realtor who made a ton of money by war profiteering.

Essentially, rich people sell huge houses at a massive loss in unstable countries when they think conflict is getting too local. Her father would buy the home cheap, and if it survived the war he would turn around and sell them with huge margins after the conflict settled. That was his business.

Anyway, he kept up with his rich clients and sold them vacation mansions in the states later on. Rich folk have such money to waste.

He then paid his daughter (my girlfriend) 800 bucks a month to “check in” on the client’s mansions once a month or so to make sure the mansion hadnt burned down or something.

Keep in mind his clients lived in dubai/london and never came to their vacation home in the states a single time in 20+ years despite spending all of the money to get them furnished and everything.

So me and my girlfriend would go to the mansion and just sleep in the mansion for a while sometimes.

I’ve known other well off people but to this day I have not set foot in another home as huge as that fucking mansion.

Their master bathroom had a separate room where the entire ceiling would shower water. Fifty people could all shower at the same time in there. I got to shower in there by myself on several occasions.

49. My dad, he broke up with my mom and now lives with an 80 yr old… he’s 50. She’s rich and he’s basically homeless, but he’s handsome and looks good with her. She supplied his cocaine addiction for years, and then she also supplied him money to chase me and my mom through the courts over custody.

50. Went out drinking with my cousin on a Thursday night and we ended up meeting a MILF at the bar he’d hooked up with before. It’s closing time and he invites me over to her place to keep the party going (I was supposed to stay at his place, so I didn’t really have anywhere else to go.) At the end of the night, she made me a bed in her guest room. I woke up the next morning with a terrible hangover and people are rushing around and I’m like WTF is all this noise? I emerge from the bedroom and sitting at the kitchen table is my cousin, the MILF and her two high-school-aged kids. Mind you, I’m 22 at the time and my cousin is 23. MILF packed us lunches while she made her kid’s lunches and sent us off with brown paper bags and gatorades. The kids were less shocked than I was. I think they were used to it. TC mark

Image Credit: Hanna Postova

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