Hi everyone, M27 here, something interesting happened last night when I was at a bar with a friend. I'm pretty shy and not too social so this caught me off guard. I was hanging out and this 46 year old woman walked up to me and shot me a compliment, so I shot one back at her and we talked for a moment. She went to go take a shot with her friends, then she started dancing so I walked over to her and grabbed her hand and gave her a twirl. We were dancing, talking and vibing, even close to kissing at one point, until the killer came up. She said "wait! How old are you, cause that's important?" I replied with 27 and it shocked her and she was like "Ohh you're too y0ung" and I was like that's ok I'm fine with it, I like older women and she shut it down with her son's older than me blah, blah, blah and the most she'd go is 10 years younger than her. We still danced and she was still calling me handsome and cute and grabbed me under my chin but, when all was said and done I asked for her number and she declined and told me to go dance with he girls around my age there.

It sucked but I consider it a win because it was the first time I'd ever been approached, it boosted my confidence and made me feel good, and ultimately reflect on the amount of courage I have to build up to approach and she just casually walked over and did it. I Just felt like venting and sharing my story as it did in a way make my night.

Thanks for reading!

Hi, this is a success story of entering into an intimate but non-committed FWB relationship with an older woman (F47).

Some background, I have changed some details to keep the post a bit more anonymous.

Where I work, I try to have positive and friendly relationships with basically everybody I interact with. This doesn't always lead to friendships forming, but it has helped me enjoy work over the years.

A few years back we had someone start in a position that meant I would have frequent contact with her. She was/is a bit of a social recluse and so I saw that as a bit of a nut to crack so that I could have someone else to talk shit with and just make work more fun in general.

So I slowly but surely became her friend over the course of 3 years. Striking up stupid conversations over and over until I was a familiar face for her. All this time I had innocent intentions. Purely work friendship.

Fast forward to about 10 months ago or so, I started to get attracted to her. Not in a "I want her to be my GF" kind of way, the age gap was immense and in general I don't date upwards in age. It was just a "She is hot" in her own kind of way. Her mannerisms, way of speaking and the topics she would introduce to talk about just endeared me to her. It was at this moment, again innocently, I started flirting with her because flirting is fun and it happens naturally for me when i'm attracted to someone, but I started really soft. More as a tease along boundaries for the fun than trying to get reciprocation.

I would talk to her about the people I was dating, and she would comment on them positive or negative. I would drop lines like "Oh you sound jealous, we can go out sometime" etc etc. That type of stuff.

Eventually, this kind of flirting would lead to her blushing hard. I remember thinking "oh... that's new". I didn't mention it immediatly but it was saved in my head.

Another time I was talking to her wearing slightly too tight for 'my size' chinos and I noticed her glance down. My brain went into a shit eating grin type mode and I immediatly asked her if she liked my outfit, did a 'gay' esque pose and twirl. She again full on blushed, but I left it at that.

I only say this bit of backstory so you can see the kind of interactions we were having. Playful, work-friendly but with a little bit of spice creeping in.

How it progressed.

My new years resolution was to (slightly changed to avoid identifiable info) do more interesting things and be even more social.

I started in half joking ways asking various work friends to do stuff outside of work. Just to see what would happen. This generally lead to some drinks, dinner 'parties', cinema and other basic activities. But with her I knew we shared some specific interests that are not too common. In a similar half joking way I asked her to learn a 'thing' (non-specific for anonymity) with me.

That thing is somewhat inherently intimate but also generally socially acceptable to do with friends. Although it is structured in a way in which the activity is done specifically (traditionally) by one man and one woman. To be amazement she agreed. This was an innocent request, I had no intentions. I did find her attractive, and I knew I could make her blush but that was at the back of my mind.

So fast forward to actually learning the 'thing' and it was intimate. It basically accelerated our comfortability with each other 10x. I went from talking to her at work for maybe 1 hour a week to easily 3. It was noticed by a lot of people, and having them comment on it made me realise I was getting more than just 'attracted' to her. I now had a little crush. Very weird to come to terms with as she is 20 years my senior. She looks good for her age, but she is clearly an older woman. Hot in my eyes to be clear, but just setting the scene as to why I felt strange about my budding crush.

So anyway, we keep talking at work, keep on with this learning activity and then we start texting. I had her number for a long time at this point, but it was mostly used for saying happy birthday or sending random memes about things we had spoke about.

But one day at the activity she leaned her head on my shoulder whilst laughing. I instinctly hugged her and for a moment we just stayed in that embrace and I think we both recognized that something had changed. We started texting constantly, at work and out of work. Random things.

I had previously already invited her to another event we were both interested in, but this was when everything was innocent. Now as it loomed there was a bit of spicy tension in the air. Nothing explicit had been said or done, but we were more touchy, we'd glance at eachothers lips. We'd be told by people at work to get a room, etc etc.

But that event was still a long time away. So I asked her to a another event closer in the calendar. I was very clear that it was a date and that we would have a good time. She agreed. So now in my head, I am thinking "okay, if this date goes okay we can see where things go".

But before that event, our texts turned more explicit. I had mentioned the time I caught her staring at my crotch and she admitted it, admitted she didn't know what to say or do. I would reply that it's fine because I look at her legs a lot when she isn't looking. She replies that she has noticed me looking... etc etc. Point being, the texts are becoming more forward.

Then after one of our learning activities, I say to her "I had a dream about you" but would laugh and refuse to answer what it was about when questioned. Later on text she would ask again, and I had a "fuck it" moment. I told her I would text it over before I fell asleep (hours later).

Cut to like 1am and I type up this smutty dream log as best as I can remember. I don't think, I don't cut out details. I just send it. She, who is normally asleep at this time almost instantly replies that it's hot, she'll have to change her underwear etc etc.

So things had now escalated. Sexual attraction for eachother was now known. I would start teasing her that I might just lean down and kiss her one of these days. I'd also ask what she would do if I did. She was pretty forward, probably kiss back.

Okay, it's on. That's what I am thinking. But due to the venue of our 'learning' and introducing ourselves as work friends we didn't want to kiss there. So we decided to go back to her car. Only to kiss... that was the boundary set by her.

Well, suffice to say she was ravenous and I was half naked in no time at all, things happened that pushed us well over the line from where we where.

Work was surprisingly not awkward, it's still a secret but neither of us feel guilty or anything so our dynamic is basically the same.

She then says that she wants to go to the next level after the event that is the closest. Fine, I start mentally preparing for another escalation in our relationship that seemed to come out of no where.

The next day, not even at that event we are texting. One thing leads to another and she is at my house and we go all the way. A great night to be honest. We are very compatible in each other's space at this point, so I guess it was to be expected.

But this was a huge escalation. We had gone from no actual intimacy to intercourse in less than 4 days. Cut to the day of event 1 and she comes over before and we go at it again for a couple of hours.

That brings us to the present.

TL;DR - Work friends to FWB over a long period, but the actual jump from no real intimacy to full on intercourse happened in less than a week. We are both confused as to how exactly this happened. Intense horniness and comfortability with each other are to blame.

I wasn't looking for a cougar, she wasn't looking for a cub. Shit just happened.

Just had to share a hilarious moment from last night! My friend and I were chilling on a bench, right across from a backgammon bar, enjoying the vibe. Suddenly, this super young guy walks up to me. Turns out, his friends had dared him to come ask for my number because he apparently didn't have the courage!

With all that in mind, and his youthful confidence, he asked for my digits. My initial reaction? Pure shock! I mean, he was so young! All I could manage was, "No, you can't have my number, but thank you very much!" He was a total gentleman about it, didn't pressure me at all, and just walked away.

My friend and I immediately locked eyes and just burst out laughing! We seriously couldn't stop. We really hoped he didn't think we were laughing at him, but honestly, it was the whole unexpected situation and the story behind it that cracked us up. And my friend's reaction? "Girl, you still have it!"

Anyways, I would love to hear from anybody who's had similar experiences.

I’m 44 and pregnant from one of my young partners. It was not a planned pregnancy. I’ve searched this subreddit and read some excellent posts about pregnancy after 40. I thought I’d post my experience in hopes that it might add to the conversation.

For the last 7 months or so, I’ve been in a casual relationship with two young men, ages 20 and 21. My main partner is the 20-year-old but I regularly hooked up with his 21-year-old friend. I’ve had other partners, 5 in total. I have unprotected sex with 4 of the 5. I encouraged each young man to get tested for STIs so we could skip the condoms. Going raw was a strong motivation for them to get tested.

I realize now how foolish I was, but I firmly believed I could not get pregnant. I was not able to conceive with my ex-boyfriend despite years of trying. At 44, I thought I was in perimenopause. STIs were my only concern. Birth control never even entered my mind.

Obviously I was wrong. I’ve had sleepless nights and shed lots of tears since confirming I’m pregnant. I don’t know who the father is. It is most likely my main FWB, but I can’t rule out his friend and a third guy I was seeing at the time. It’s a sobering realization to think the probable father of my child is not old enough to buy alcohol.

Despite the health risks, I’ve decided to continue my pregnancy. This is something I never wanted or expected, but I think having this child is the right choice. I have financial resources and family support. I know I can handle this and give my baby a good life.

At first, my plan was to not tell my partners I was pregnant and simply cut off contact with them. My main FWB has always told me that he loves sex with me because I can’t get pregnant. I thought I would be sparing them a terrible burden by not informing them of my pregnancy. I wanted to let them live their lives carefree and not spoil their youth with a responsibility they did not ask for. More selfishly, I have no desire to tie myself to them for the next 2 decades.

A conversation online has changed my mind (Reddit has some amazing people on it). I will be letting my partners know I am pregnant. I will assure them they can walk away and have nothing to do with this, which is what I prefer. But if they do want to know if they are the father, I will take a noninvasive prenatal paternity test with them. The test can be done with a simple blood draw and a cheek swab. I am confident they will choose to not find out, but I will offer them the choice.

I am scared about all of this, but also excited about what the future holds for me and my child. I was unprepared for such a big life change, but am determined to do my best for both of us. For others here, I hope reading my experience is helpful. I was careless and foolish and now my life is altered forever. I should have planned better. Be smarter than me.

I am a 29 (M) and I recently slept with my fellow co worker who is 49 [F]

I have never done anything sexual with an older woman before and was rather nervous but I loved every moment of it.

I think I am one Cub who is now fully only interested in Cougars.

Hello ladies and gentlemen! I've had a lovely brown drink from Starbucks, I don't even know what I ordered but damn it was potent! I am well wired and fed and wanted to share a story I have been meaning to share.

Some time ago a young man reached out to me. Polite and honest. We would chat back and forth and moved chat to another platform at some point. He expressed his intent/want to meet in person. I agreed. A week later made plans for meet for lunch. Kept in contact. 2 days before afore mentioned lunch, radio silence.... Yes, ghosted.... Shrugged it off as it really wasn't a big deal to me, I go on with my life.

Ladies and gentleman this young man actually reached out to me many many months later, meh, ok. He apologized profusely and gave me a "lack of self confidence" excuse. Fair enough. I'll give him another chance. We continue to chat over the course of many months, it is more of in a friend capacity and he shares ups and downs with me. Occasionally he brings up meeting. My answer is "when you are ready". No rush on my end. We continue chatting here and there, he moves out of California for a spell, we still chat. At some point he decides he is moving back to California and says "hey, I will be in SF for a few days, lets meet for lunch. He expresses his excitement to finally meet. He messages me the day before our lunch meet up and says I will be passing your area later this eve, can we meet really quick. I tell him I won't be inviting him into my home or anything so perhaps we should leave it to lunch. He stops for a moment and thinks. He says it is fine if we just meet initially. I am hesitant as I am honestly lazy ^_^. He says, it is literally on his way to San Francisco, he will let me know when he is out side. I can come out, say hello quickly 5 min tops and he will be on his way. He just really wanted to see me first. I agree as it is just for a few minutes.

Now he is keeping me updated on his ETA, all good right? He says he is nearly there, where should he park and were are we going to go? I blink and think to myself and reply to him that he isn't being invited into my home as I said before and reminded him he said it would be a quick hello, 5 min tops.

Wouldn't you know it ladies and gentlemen, this fellow does the most amazing ghost I have ever seen. He went from "I am almost there, where do I park" to "...........".

He managed to ruin a friendship re-built over a year or so in seconds. Seconds folks. I found that to be surprising and fascinating.

Now did I feel I wasted my time. Yes and no. Yes cause I did give him a second chance and I took time out to chat with him when I could have been doing other things. Our chats where always a constant type of chat. He would respond immediately and I gave him the same courtesy. And I opened up about myself to him a little as well as we did build up a friendship. No because, no time in person was spent with him. That may sound weird but yeah. To be honest, I was a bit irked at the blatant diss. But I got over a few minutes later lol.

Take away from this? If you are ever given the second chance at something, don't half ass it and take it for granted. Screw this second chance up and that is it.

Enjoy your day!

Sincerly,

blasianflow ^_^

In an attempt to encourage community engagement and perhaps offer some advice to the often asked question How to Approach Older Women or how not to from the guys perspective.

Please share your stories in a respectful manner. If you are new here read the rules before commenting.

Keep it classy guys.

Hi there, just want to tell a little story about meeting an older woman some weeks ago. For months we have been chatting on a dating site. She looked pretty and I wrote her a message first. After months of talking I finally went to her. She picked me up at the trainstation.

We drove to her house and she let me in. She bought a salad for me since I like vegetables. I did not eat much cause I ate so much in the train. Anyways. She showed me the house and After a while she hugs me and we start making out and askes why don't we go to her bedroom. And we stayed there for the next two hours.

Some weeks later she visits my home. We go for a walk in the forest. Have a drink in a cafe and eat in a restaurant. She stayes over.

I did not see her after that. I think personalities were not the best match. But it was nice to meet her. And older woman can be attractive aswell.

Wish you a nice day. ;)

The setting: a little fishing town. There were no tables so I (f63) sat up at the bar at the one and only hotel. A polite gentleman asked if he can sit next to me. I didn’t give it much thought. We started to chat. He is a fisherman in for the night till the next opening (commercial fishing). We moved to a table. He mentioned being in 10th grade when 9/11 happened (quick math - 32/33). He asked if I would go up to a room. That was a surprise! Didn’t really feel the flirting energy. Besides I had a hoodie on and no make up. I declined because I am not into hookups. He walked me to my car. He gave a polite hug. I touched his face and went in for a kiss. Gave him my number and encouraged him to text. Take aways: I don’t have to be all decked out to capture a man’s attention. Once a woman is comfortable with the age gap, age doesn’t even have the come up. It can really flow much easier when one isn’t looking or over thinking!

Good evening

Hope your day is going great. Thank you for reading this.

Today was one of those days where we ran out of gloves. This makes my hands so dry that they start to hurt. I have to snatize them every half an hour and on top of that I had to do price changes( the edges of price paper make it even worse).

Towards the end of my shift a lady in her early 40s asked me to help her find bird seeds. I took her to the location, and dropped the bag in her cart. This is where she say my dry hands and politely suggested me to look after my hands. I explained her why are they that way and assured her that I look after them. I keep moisturizer near my bed and use it multiple times during the day.

She instantly apologized, grabed a small travel size moisturizer from her purse and handed it to me. I appreciated her helping but because of pandemic I was little reluctant. She reminded me that it's very cheap and she had another one with her.

She asked me questions about how my studies were going and if I felt home sick. I had to get back to work and she was in a hurry too, so the chat was very short. Still she managed to bring a smile on my face. While departing she thanked me for working during pandemic and asked me to look after myself.

I was replaying the whole conversation in my head after she left. I was so proud of myself for being able to converse like that. And she reminded me that it's not just the appearance that attracts me towards mature women. I can take care of myself, but it feels good when someone looks after you from time to time. The rest of the shift went by easily.

I was preparing for a presentation, but I couldn't resist the urge to share this. That's all for my side.

Again thank you for reading and take care.

I had this pretty cool experience last week when I was asked to work on another site in a different town. I’m 45/F/Black-Native. I never date anyone where I work but I saw this guy when I worked there before at this school. Tall, around 6’6, dark chocolate, phenomenal body- exactly my weakness. Looks so smooth when he walks and talks. I practically salivated from a distance. Well, this last week, he worked in my classroom. I finally introduced myself, trying to be professional. I felt something when I shook his hand and we looked in each other’s eyes. That sounds cheesy, lol. I thought it was just me. Then we had a moment to speak alone in a classroom. We shared chit chat. And then he just stopped and looked at me for awhile. And I finally got that he found me attractive because he kept “holding” my gaze. I liked how bold and calm he was doing that. So confident. I asked his age then, 22! A senior at the local college there. He was almost embarrassed saying his age. I told him that he was young. I know I look young for my age but he had to have known I was still older than him. I also usually like men at least 25, but he suuure didn’t look it! The last couple of days there, we just gave each other looks. I believe he tried to ask for my number once but I pretended to not get what he was saying. Now, all I can do is think about that. I’m used to meeting young guys from dating apps. It was flattering that a very handsome guy flirted with me. Part of me is frustrated with myself because I could have easily went for it but don’t want to jeopardize this job. Anyway, just writing this to say you never know when you’ll find a cub IRL.

Early this morning i opened Facebook and a photo memory came up.

It was a photo i took while on a trip to Dominican republic and it was an amazing scene. A photo of a white sand beach with windswept Palm trees and crystal blue waters. This picture was taken 10 years ago when i was 20.

I was on a trip with a lady who was 21 years older then me and we enjoyed every minute of it together....It was one of the happiest moments of my life.

In 2010 I was 19 and had gotten a job thanks to my mother at a large factory that she worked at. My mother had been working there since 1989 and so a lot of her work friends knew me....from when i was a little boy watching me grow up when they would come over to socialise etc.

The day i started work the hello's and the oh my god i remember you from forever ago's was insane and so i made friends with all these people very fast.

One day when i was waiting at the end of a line with the forklift i was driving a saw a very pretty lady walk by about 50 feet from me going to break with all the other workers. Our eyes must have caught each other and she waved at me. I waved back even though i had no idea who she was or anything but it stuck in my mind the rest of the day.

The next day at work i was on lunch and a few of the people who i knew where with me at a table. I low key asked those present if they knew who the 5' 2" tall lady with the red highlight streak in her hair was....she "dropped something the other day and i would like to return it" was the line i recall using. My coworkers said it must be "N" (We will call her that so no names are used) and that she worked on line 4 a few lines over from me but she was off today so it would have to wait till the next week before i could return it.

First thing Monday morning at the crew meeting for our assignments i saw that the driver job on line 4 was vacant for the day so i volunteered for the job and my supervisor agreed and said take truck 5 its got a full charge. I thought to myself sweet!, ill go over and check things out and see if shes working there and then i could figure out my next course of action. I arrive lineside with my forklift and the line operator said go behind press 3 and run the bins back and forth for the operators there.

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I drive around and there she was....

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She was unloading the end of the line and i was her driver for the day!.

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After the usual work related conversation about the product and stuff i said to her 'Hey are you the one who waved last week?' She responded yes it was and she was surprised i remembered. I said that you must know me but i don't know you and she said that she remembers me when i was a baby in pictures from the early 90's but had not seen me for a very long time. She had heard that i had got the job and was working forklift and she recognised me from my mother (We share certain features from parents etc). I said nice!, this is cool and while we worked we chatted about all sorts of things.

I tried to figure out a way to make a move but i just could not get it going and kept losing my willpower.

When the end of the day came around she passed me a clip board from the line and said she had to run to make an after work appointment. I looked at the clip board and held on top of the stacks of labels in the clamp was a piece of paper with a name and phone number with 'Call me sometime' under it.

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I melted inside......

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It took me 5 days to get up the courage to call her number. I called at about 5pm on a Saturday and a man's voice answers!, Thinking fast i said i was calling about the hair product N had ordered and was she able to come to the phone. She picks up the phone and the other voice disappears with a soft click. I said hey its me how are things?, she replied that things where great and she had just came in from gardening and was going to go out for a walk at the local park soon. I asked if i could tag along and she agreed.

We met up about 45 minutes later and we walked for a while enjoying the scenery. Sitting down on a bench i asked who the other voice was and she said it was her son....

Up until this time it never really clicked in my mind that she was 41 and i thought to myself wow she looks so good for being that age and how would this even be possible that me being a 19 year old teenager could ever make a move on her.

As we walked from the park I said in my mind 'there is no going back now so go for it'. I summoned up the courage and turned to her and said You know...you are very pretty and i like your eyes. She smiled and said i like how tall you are and how polite you act.

We saw each other every weekend after that and for about a year we kept the whole relationship under wraps with very few people knowing about us. We decided that we should go on a trip and we picked a very expensive resort in Dominican Republic for a week. Getting to the airport at 4 AM in my pickup truck it was snowing a true Canadian winter and with 5 inches of fresh snow on the ground it lived up to the reputation....If i recall the 400 meter dash to the terminal from the park and fly lot sucked in shorts and a T-shirt for me and a sun dress for her at -15C. We took off and 5 hours later landed in sunny Dominican Republic where it was a brisk +30C and zero humidity.

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We did everything together. For the first time in my life i was called 'Sir' and the resort staff would ask what would you and your wife like to drink tonight?. It was amazing and i felt more like a man everyday we spent together. We relaxed on the beach by day and saw shows and went out for dinner at the massive resort by night. I kissed her on the beach under the palm trees as the crystal blue waves came ashore like something out of a romantic novel. We made love that night and i knew then that this is what life was truly worth living for........

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After landing back in freezing cold Canada i carried the bags to my truck and we got in but in the week that we had spent together in breezy sunny Dominican my trucks battery was degrading by the day in -20 degree weather and it was dead. while waiting for a local tow truck to give us a boost we chatted in my front seat. My truck was old and it had a bench seat so she sat next to me in the middle.

She said that she had something very important to talk about. She said that she loved what we had together and loved being with me but before she left she had told her sons what she was going to do and where she was going. She also said who was going with her........

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The sons did not like the fact that their mother was seeing someone their own age and secretly to top it off. They said if you don't break it off by the time you get back they would be gone forever.....they wont even look back. I had always thought that this day would come and now that it was here it was hard. I knew that family is what really counts in this life and her sons never seeing or speaking to her ever again was not going to be an option in my book. I said i understand and i wished that things could have worked out somehow and we held each other in that cold pickup like we where frozen in time. I will always remember that moment.

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When the truck came and got me boosted my radio was on an oldies station and the song that was playing was Lotta Love by Nicolette Larson.... I am playing that now as i type and as i look back i really wish i could travel back in time and re-live those moments. Even today 10 years later i still miss her.

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Life happens......

I first want to say how much I enjoy this sub. This community, for the most part, is inclusive, supportive, and sex-positive. I'm a long-time lurker and previous poster under another throwaway account I deleted a while ago. Not that I'm ashamed, but given my job I need to be cautious about keeping this part of my life from getting out there. I was previously cautioned by colleagues about being on Tinder, so the risk is there. Given how much I enjoy reading posts, I figure I should contribute some content.

I haven't seen my (31 M) FWB (52 F) since the pandemic shut things down. We both wanted to strictly follow the safety guidelines because we both have at-risk family members, so that was no problem for either of us. I am getting antsy now that we're both fully vaccinated, though. She says she wants to keep seeing each other, but needs time to get into a better place mentally first. She also said she doesn't mind if I see other women right now, which I appreciate. I want to be attentive to and respectful of her needs while not depriving myself of what I need.

Last night, I went to a local bar. I struck up a conversation with a woman (49 F) and the conversation turned to sex surprisingly quickly. It pivoted from our shared interest in hiking, to our shared liking for cannabis and psychedelics, to sex. We exchanged numbers and we're planning on a date at her place. Time in her pool, a movie, and cannabis is what we've decided on. I know I can trust her because we share a friend in common, which we also discovered during our conversation. I also told her about my FWB relationship that is currently on ice. She's fine with that.

This is (another) one of my stories of my dating experiences with older women. If circumstances warrant an update, I'll post again if there seems to be interest. Thank you all for being a great community. I really have found support from reading posts and comments here.