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Cataloged in Romance

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

These people from Ask Reddit make want to date an 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 yes. She spoiled me and pd for everything but my self-esteem suffered greatly. Was kinda fun being on two ye vacation but hd to expln 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. her to give my ex another chance, it ed. Well to be fr, t were other s (milf got too attached and I didn’t want to hurt her) but that was the mn one.

3. I’ve had multiple “sug mommas” and it was the best, for awhile at least. I would have died if it wasn’t for one of my sug mommas. When I moved out to , I had no for food or anything else. Sug 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 probably spent thonds of dolls on me.

Unfortunately, I was not attracted to her AT ALL, and she wasn’t a person. I stted to feel that I didn’t actually ce about her and came to the conclusion that it’s a idea to use people for /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 w I was unemployed. To stt getting benes 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. meeting she used agency to buy me a suit, 2 shirts, 2 ties and about $600 in fuel .

Basically a one night stand turned pretty proable.

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

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

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

8. The mother of one of the kids I was a or for at a summer day camp. She would show up late then bring me gift to apologize. She would hang out and flirt with me while I closed everything up. Ne the end of the summer she told me as a thank I should come to the high end men’s store she runs and get ted 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 w 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 . Would always make me come over and . Sometimes even give me the keys to her BMW to get ound 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 certn time after I got off work (which was basically the commute time plus five minutes). I certnly 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 yes than me, and she became very infatuated with me. I got a place to live, food, , and Pokémon s from her. I cut her off physically when I got a friend later in the ye, but she still kept paying for my stuff. I feel genuinely awful about how much I took 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 ye or two than me was into me, but her mom blew her out of the water in the s dept. To make a long story short she basically took ce of me for 2 yes. We spent both winters at her ski-in/out condo having sex and sboding. I moved on to another woman that was in her mid 30’s, same thing. I’m in my late 30’s seeing someone in her late 40’s. I’ll just say she takes great ce of me.

12. In my ely 20’s I met an woman ound mid 40’s in a b. 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 sd thanks and that she ed great too. She gave me her business cd (realtor) and told me to text her ound 2am. I did. She rolled up to my place in a super nice Benz. Woke up and she was gone. weekend she texted me an address and to be t at 8pm and to cle 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 k I was interested in. The weekend, same thing. I showed up and she had so much stuff for me. Really nice high end clothes and . 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 Eth. 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 ne 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 sug momma, a friend of the I was dating at the time. He was this average ing 20 ye old stoner kid who was living in a nice house in the . His sug momma was paying for him to go to community .

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

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

Anyone who ks Japanese has hed her name before. I didn’t k 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 neby . She tells me she needs preping for an at a very famous for a very role that they would essentially be creating just for her. I tell her I’d be happy to her with it – I didn’t have any ulterior motives, I genuinely liked her and wanted her to succeed. We met up agn to do the prep, and one more final practice after that.

She invited me to play dts with her after we’d finished since she appently enjoyed dts and I’d never played before. We went out to a dts b in the ely evening, and somehow we ended up playing a w the loser of the had to drink tequila shots. She mopped the floor with me but we both stted doing shots until well past the last trns home.

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

She turned out to be richer than . She would buy all kinds of stuff for me, would never let me pay for dates even though I was making very good for my age, wanted to take me on all kinds of trips ound 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 Mtin and some other just lying ound in her spaces in the middle of Tokyo.

Probably would have mried her if it weren’t for some complications with her mital – 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 mriage and had a ng . 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 stted 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 mriage and both of them were seeing other people, but due to their very high profile in the Japanese 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 ceer and that a divorce to mry a white guy would be the end for her professionally. That really sucked but it was the truth. She was the best friend I’ve ever had – if I’d met her 3 yes elier I’m sure my life would have been completely different . Not for the , could not ce 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 visiting from NY. Didn’t see the point as I was ing for a relationship. Had a good time, wasn’t doing well at the time, so she flew me out to York and pd for everything, rbnb, so forth. She flew back a few times, became cle she was emotionally unbalanced. Sweet and I wish her the best.

17. Had a huge crush on my friend’s hippy mom for yes when I was a teen. She k. Some 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 sug 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 semi frequently. on day nights. The always comes in viously very very well tlored interestingly patterned suits. He’s 23 and his sug mama likes seeming him dressed up certn ways and he likes the suits.

19. Hooked up with my roommate’s MILFy friend, ended up dating for a ye and a half. She lived in a big, brand house with her estranged husband and kid. They had sepate bedrooms, he k about me and wasn’t really happy about it but she controlled him and he wasn’t a problem. She came from and had a good job, and the husband made good , but couldn’t manage it, so she got all of his , on top of her own, and ptied pretty hd. 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 yes me, her son was 19. Well we stted to flirt and eventually stted to hook up. Well any time we went out she drove, bought the food or , 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 ely 20’s, I met someone . She was good ing and had a nice . She was in her late 30s We fell for each other, and I found out that she is rich AF, when she stted 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 pro, but she had 2 kids and she was certn that she lose custody if she mries 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 remry him!!!! I didn’t want to see her growing up alone! Back to the mn 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 American (27 yo, 3 kids, mried but sepated) who offered me (20 yo at the time, European, single, Uni student) a job in her ’s business in Miami, a lot of cash and benes 10 yes ago. She was super cute too, and the sex was good, but I just couldn’t say as I was focused on graduating from University which I did. She was super nice, we e still in touch. She remried and had 2 more kids after me.

23. I was an intern at HQ for a when I was ound 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 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 ts and funded my first album. It didn’t do well, but she loved that t was a song about us on t.

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

She kinda went crazy later, which lead to her being fired and I left the soon after. She ended up 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 going at it in the boyfriend’s place, I figured it was best that we ended it.

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

24. 19 yes between us. We met when her c broke down and I stopped to 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 yes 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 sug mama in that she didn’t have any herself – she was a teacher and a single mom – but she k tons of people and she got invited to some really nice pties and events.

That summer was a blast. She taught me a ton about ing, we had killer sex, she had fun slummin’ it with my , I got to be her m candy at all kinds of pties in really nice houses, some private rooms at clubs, t show after pties, like that.

We never really made it anything official. We always joked that I was her pool boy and she was my coug. As the ye stted we both settled into different routines and drifted apt 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 women. One was about twice my age. I don’t k how old the other one was.

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

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

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

Eventually they broke up because the guy was appently being a controlling asshole to her. I kinda saw it since his in our guild 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 . 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 for a week and asked me to show her ound to the best for us to spend our time together. I didn’t mind paying and suggested stuff within my price range ( student at the time), but she ended up convincing me to try some (more expensive) I never considered doing since she’d be covering everything while telling me not to worry, and thanking me for being t 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 way out of my price range, went clubbing with our own table, it was definitely an eventful week. We already agreed on nothing being – we were just enjoying being in the moment and it was totally fine.

She flew back, life went on, eventually we got up in our own lives and stopped playing as much, which meant our communication stted winding down as well. It’s actually been yes 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 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 stted 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 ”. If s could kill, I would of murdered him. She ed over at me and sd: “Oh really? What did say about me?”. I 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 gden come to find that out the morning. She told me to come into her house and we fucked. That’s the stt of how I ended up dating a milf for nely 5 yes.

31. Not as in depth or freaky as others but I had an woman buy me a gift cd for a ye of Netflix. When ’re in r mid 20s and don’t have a lot of 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. Afterds we went to her aptment and had the most awesome sex of my ng life. 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 took ce of that. And the c payments. And credit cd bills. Eventually I found out her owned thonds of acres of fmland, three radio stations, and a tele station. After a few weeks, the sex got less and less, and she began spending more time out with her . Guys would come by too; guys weing colors and riding Hleys. Slowly the truth stted coming out: she was gay, the women were her rich and drug clients, the bikers were her drug dealers. She needed a man to live with her to keep her rich extremely conservative from guessing that she liked women and cutting her off from her . 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 neby which I was funny considering we worked at a grocery store. She flirted an awful lot and strght up asked me to come by her place after work. We smoked weed and watched tv and had lots of sex. Always told my I was going to a . 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 if I wanted beer or weed, but would then leave the beer and weed king I would drink or smoke it all.

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

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

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

35. A while back I posted in a couple subs for meet , and a woman actually messaged me. We connected pretty well, and found out her job took her ound the US. She also was in a poly relationship, and just liked having guy everyw, so I just became another one of her boy.

When we stted 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 ce package. It was 2 brand s, a hoodie, some comics, and a funko pop. It was a lot to spend on me even though we hadn’t kn each other that well.

36. My friend ens really good and works for a organization in a poor country, so she bely needs to spend anything. She’s 33 and just likes nger guys, maybe ound 21-25. She sd 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 woman (I’m 23, she’s 37) with some “sug momma” elements to it (mostly that she buys me nice s and and I give her a good time in bed playing a switch). We met on Bumble; she says she wasn’t originally ing at guys my age but her friend messed with the age thing without telling her and she ed with me.

She’s a /resecher and I’m a grad student (not her student, but in a simil field at the same university so we have a lot in common). She didn’t actually realize I was that much nger until we’d already been for awhile and had a date planned, but she went through with it anyway and the sexual tension was t from the stt. 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 en’t exclusive or anything; she goes out with other guys her age and I go out with other s my age. She actually encourages it; she even likes heing me talk about whenever I get ld with a nger .

It’s kind of a crazy whirlwind thing, especially since I was a virgin less than a ye 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 to death.

38. I went to a b one time and this coug 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 ford to later in the relationship) She told me that she wanted to get engaged before she left for her 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 pd 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 ye old widow on Xbox when I was 19. She sd she played Xbox to pass the day because she was ly set for life when her husband passed and wanted to make some Xbox . We stt playing more and more until I couldn’t keep up because my controller and set broke. She asked for my address and after a week, I got a brand controller and set. 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 few yes, she occasionally buys me s when they came out and even a few Collectors Editions if I wanted them. Eventually, we drifted apt because I couldn’t find time play with my and work schedule.

I still miss her and occasionally try and find her agn but can’t remember her rtag or . She always be one of my best buddies I’ve ever had

40. I met an MILF when I was 27 ( she was 43 ), and I think it was really more of a “boy toy” situation, though we were still . She would basically take me all ound the state on her trips as a 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 agn, and be on our way. It lasted for just over a ye, 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 Pks. We even had a thing w we’d impersonate The Count with “TWO National Pks! AH AH AH!”, and then laugh like idiots.

41. Former teacher 10 yes later.

42. This happened to me a couple yes ago. I was back home from on a break and ed with this 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 pked 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 the morning. She sd she had to go to the mall to return some stuff and asked if I wanted to tag along. I sd sure why not. He go to the mall and she’s returning some clothes or something so I’m just ing ound 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 sd hell yea but it’s like 250 bucks and she sd she’d buy it for me. I just laughed. She took it off the rack and went to the counter. I she was just really committed to the bit until she pulls out a f FUCKING FULL of $100 bills. My jaw dropped and probably made a weird sound. She just ed at me and winked. We left the mall and I had my dope ass jacket all bagged up. I asked her about the and she just sd “don’t worry about it.” We has been talking for a couple days and I k a lot about her at this point and k 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 c she says hold on and pulls out the f. I ask what she’s doing and she just throws $600 into my bag. I felt weird and tried to give it back. She sd don’t worry about it I have a bunch. She opened up her purse and pulled out like 6 or 7 of these fs. Eventually she convinced me to keep the and I was just like fuck it, I’m a hooker I guess.

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

I go back home agn on my break and decide we should meet up agn. This time we skipped the sushi and went strght to doing the ole bippity-boppity-boo. Agn, go great. She says the night and we watch a movie the morning. She eventually decides its time to leave and puts 10 $100 bills on my coffee table. At this point I k 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 Snap and it s like she deleted me or blocked me or something. Turns out she blocked me on every form of social . 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 agn. Still haven’t hed 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 and a little sced 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 hed from her agn. Still got the Patagonia though!

43. I got a free personal trning session at Equinox gym. This woman working out t 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 ting her up the end of the session. Super pretty and 41 ye old, incredibly intelligent, with her own private practice doing sex therapy. We seemed to click. I’m 26.

After my session, the trner/people allowed me to stay and keep working out on my own. Then this lady makes her way back to me prob since the trner 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 strght up tells me I’m cute and she’s always busy, so she’s ing 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 tot (?), and she likes to analyze me and eventually wants to “read my .” Idk whatever, small price to pay and tbh it actually is pretty interesting and sorta sexy when she talks about it.

this wasn’t a sug mama type relationship at first, but we stted going out to just for fun, and even though it’s not date-y really, she’s pd for everything since. Then it evolved into buying me some nice —nothing too personal like clothes, but she’s gotten me some nice bottles of wine, scotch, a candle she liked, ya k nice gift type . Well this week these just went a step further, she’s going to Bos in Februy 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 pts of the island. I’m dropping $0.

She’s adamant about not having a relationship outside of a casual one though, for numerous s 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 on me but not in frivolous ways like more cle-cut sug mamas. Still, I think the situation s well enough to comment about. Who ks, maybe she’ll stt funding my business?

44. My mom, who works as a massage , told me her boss (42) at her spa I (19) at the time) was hot when my mom showed her pictures of me. Ended up getting an add on from her, and she told me to come down to the downtown spa w 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 give me an iMac because she liked me and we played s 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 Sug Mama.

46. Fucked a milf, morning she made me and cut my hr.

47. I was at a dive b and this lady comes in, weing yoga pants, and a tank/sports bra. It was a Tuesday night. She was beautiful. ed like a hot suburban mom ely-mid 40’s. Had no idea what she was doing t. We got to ting and it turns out she was in the middle of a divorce and had been 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 day, she keeps making comments about how she can’t believe she’s with such a nger guy. I ng for my age so I assume that she miderstands and I say,” keep saying that… I don’t think I’m as ng as think” and she asked how old I was… I told her 33 and she sd that’s what she … she was 55. I was totally shocked but also it was pretty cool.

Over the ye, we had an ongoing relationship. She never ced 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 and she would always pay. She pd 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 man set her up in business , when she was ng, and how she’d like to do the same for me. And we would talk about plans for what that would like.

She even suggested I move into her spe bedroom and be roommates. Saying she wouldn’t be jealous if I brought a home. I 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 ye old lady. She was not super rich herself but her was and she was very much a dy’s .

Anyway her was a realtor who made a ton of by proeering.

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 he would turn ound and sell them with huge mgins 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 to waste.

He then pd his daughter (my friend) 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 dub/london and never came to their vacation home in the states a single time in 20+ yes despite spending all of the to get them furnished and everything.

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

I’ve kn 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 sepate room w the entire ceiling would water. Fifty people could all at the same time in t. I got to in t by myself on several occasions.

49. My , he broke up with my mom and lives with an 80 yr old… he’s 50. She’s rich and he’s basically homeless, but he’s handsome and s good with her. She supplied his cocne addiction for yes, and then she also supplied him 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 b he’d hooked up with before. It’s closing time and he me over to her place to keep the pty going (I was supd to stay at his place, so I didn’t really have anyw else to go.) At the end of the night, she made me a bed in her guest room. I woke up the morning with a terrible hangover and people e rushing ound 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--aged kids. Mind , 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.

Image Credit: Hanna Postova

is cataloged in , ,

Time To Change Your Life

Over the past few yes, Brianna Wiest has gned ren for her deeply , philosophical writing. This compilation of her published work features pieces on why should pursue pur over passion, emb negative thinking, see the in dly routine, and become ae of the cognitive biases that e creating the way see r life. Some of these pieces have never been seen; others have been read by millions of people ound the world. Regdless, each leave thinking: this idea changed my life.

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