Dating mature ladies (My Encounters and suggestions)

[lobowolf]

Much have been written about encounters with older/matured woman (both facts and fantasies) in this forum, either MILF, with friend's mom, auntie etc. Most of the thread on mature ladies have been on sexual encounter. I have dated several mature ladies (widows, neglected housewives, aunties, divorcees, ladies who have never married) and I have come to respect them more and come to acknowledge that they are not just sex objects to be lusted but to be regarded and appreciated. I would say that my attraction for ladies older than me started when I was very young for one of my mom's close friend. I still remember milking myself fantasying about her in my teens and still do (old habits die hard... Haha) .

I would like to share my experiences dating several mature ladies and getting close with them on the bed too (but not all of them). I will also share some tips on how to get the first point of contact and how to proceed from there, though I would like to add a disclaimer that it is not a sure success formula and these are based on my experiences. I don't claim that my views to be the absolute method as there are many ways to get acquainted with mature ladies and and some senior bros can also share their views and even disagree with my view.

I would like to rephrase again that relationship with a mature need not always be of sexual one. You can have a good connection with her without letting the lust get in the way. Yes, I understand that they have their needs, but that has to be respected. I have been active in chatting apps and heard them saying that guys are rather quick to send pictures of their private parts to them or talk of intimate stuffs, without actually getting to know them properly. Take time to know them first, they will be the one sharing their pictures to you. It may take months before they do that, but you need to have patience, if you think she is worth the wait. Given a choice between dating a mature lady and a younger lady, my choice will always be a mature lady and I have my reasons for that, which are listed below.
Advantages of Dating older women:
1. Very caring: They really take good care of you. I like it when they bake cookies and bring them to me to try it out. When I am not well, they will brew some home delicacies and herbs and bring it to my doorstep.
2. Financially independent: Their financial independence can extent to driving around in cars and inviting them to their place overnight when the kids are not around the house :P.
3. Their taste of things: Music, arts and fine dining.
4. Their outlook: Well dressed. Even for a meal, expect them to be well dressed (but not all). Earlier, I showed up in shorts for dinner appointments, only to realize I was way off. Now I take time to be dressed decently.
5. Teasing/playfulness: Once they feel comfortable with you, they will get cheeky with you and that is a hint but, again, don't jump too early. Tease along the borders. I like their tease. I have one woman, who would sent me pictures of her new lingerie (asking my opinion) and it is such a treat.
6. They don't expect you to pay for their meals: In most cases, they will pay for your meals too.
7. Gifts: You can expect gifts from them. They certainly will buy gifts for you when they travel abroad. It can be from souvenirs to shirts to local edibles, gadgets, watches etc. One ought to be careful in accepting expensive gifts from them as some may see that as a way of controlling you with those. Try to make things clear. I dated one divorcee, filthy rich and you can tell that from her choice of branded shoes, hand bags, designer dresses etc and her choice of restaurants. Unfortunately, she had that motive of controlling me. Its good to be showered with gifts but not at the expense of being controlled.
8. Understanding: You don't expect them to throw a drama or fuss. Though, there are some who may, but that is very uncommon.
9. Residence: They have their own place and privacy. So, you get invited to their place for meals or a drink. You can easily get cosy with them during that time It is good to spend hours in front of the TV sipping wine and playing on the couch for hours before heading for the bedroom. I enjoy foreplay and it is a good way to build things up.
10. Sexually adventurous: They will oblige for any sexual positions that you would like to try.

Points to be noted for you:
1. Listener: You ought to be a good listener. They have lots of stuffs to tell you.
2. Honest: Guys, you cannot bluff your way with the mature ladies. They have been there and done that, so no point bluffing at them.
3. Have a taste for arts: Not all have a taste for that but I have noticed that most of them appreciate arts, in the form of ballet, musicals, orchestra etc.
4. Willing to treat them for meals: It is a courtesy to pay for their meals during the initial outings.
5. Gifts: When you travel buy some stuffs to them. It may not be the expensive ones. They will appreciate your gestures. Give them flowers on their birthdays, as they probably have not received one in a long time, if they are divorced.
6. Good sense of humour: They certainly love to have a good time in the company of a person with a good humour. Make them laugh while chatting with them over the phone and they will like to catch up with you in person too.
7. They love compliments: But be cautious, as not to compliment on their looks too often, unnecessarily. Compliment on their personality, they will appreciate that more and slowly compliment on their looks - they love that.
8. Take note of their birthdate: Wish them on their birthday and see if you can take them out for dinner some day. If she is ok to go out with you on her birthday then it means a lot, as she is avoiding celebrations with her friends/family members to spend the time with you.
9. Financially independent: You should also be financially independent, unless you are looking for a sugar mommy. Be a gentleman and pay the meal on the first meet up.
10. A place to host: Once you both are comfortable with each other, invite them to your flat and prepare some simple meal. They will appreciate that. Or you can ask her to join you for grocery shopping and it can be so much fun there and you can actually build the fantasy from the grocery store itself over certain vegetables and fruits.. haha. I enjoy the foretaste :P Once you start to build the momentum, I can assure you, you will have a good time for the rest of the evening.
11. An Observer: Be observant, not to criticize her, but to complement her on her choice of dress, perfumes..etc.

Warning: There are some single mature ladies (never married) who are really looking to settle down, so you better be cautious with them if you are not ready to settle down with them for good.

Where do find or pick mature ladies?
Ahh... That is a bit tricky. You can be at a chat sites with lots of mature ladies and still not hook up with one or can just be pick a conversation at a departmental store (you will need guts for this) and see if it strikes. Chances at a store, most of the time, will back fire since they will be with their hubby or kids. But if you get one, it is still worth a shot. For this you need to be a good observer, to pick a good line. Like, for example, you can observe at what they are looking for in a store. Then try to pass them by and on the way try to make an eye contact and give a smile, as in a greeting of 'Hi' or 'Hello'. If they respond, then I would say, you have a good chance. If they don't, then better leave her on her own. Try to pass again and comment which dress would look good on her (if she is browsing for dress) and that will be a good ice breaker. You can even get friendly with the mature ladies when you meet them in the lift, especially those in your block, by greeting them or even at the supermarket. I once befriended a woman at the FairPrice and help her carry her stuffs but I didn't have the guts to ask her contact at that time and still regret that

Once you get to know them and they get comfortable with you, they will share their personal stuffs. Once they are comfortable with you, you can expect them to tease you with their hugs, kisses and flirty conversation - I love that. Slowly, things will start to take place. But you need patience for that.

Best is to date woman who are single (widow/divorcee), so as to avoid unnecessary hassle later on from her other half. Moreover, there is nothing illegal about it (if you get physically involved with a mature lady, unlike getting in trouble with a young teenager), as it is between two consenting adults. An affair with a married woman is not recommended, as it is a bit risky but the thrill is definitely there.

....continued below.....

[lobowolf]

...continued from above .....


An Experience with a Married woman
I once got close with a married woman in her early 40's. For guys who like mature ladies, she is one where you will definitely give a second look. She was having issues with her marriage and her hubby chasing after young ladies (I won't mention which national), so she was feeling neglected. I was interested in her physically but being married, I was avoiding that, other than meet up for dinner once in a while (but no hanky panky). Since she was married it was impossible for me to get invited to her place nor was she comfortable coming to my flat. But she did was something that I had not thought of. She flew over to a neighbouring country and purchased flight tickets for me too. What followed was a weekend of pure bliss. We did not move out of the hotel but stayed and ordered the food. I am not sure whether any of you have experienced this but it can be very exciting where she will leave message on which floor and room to find her and to be told that there is a surprise waiting for me. Sure enough, when I knocked on the hotel door, she opened the door, wearing a see-through lacy negligee (she knows I have a weakness for that). Ok, I am not going into the details... . But, again, I wouldn't suggest getting involved with a married woman. I know, for some, there is nothing like the taste of a forbidden fruit

How to go about (suggestions):
For chatting through online apps (Badoo, Skout, etc.), go through their profile and see if they have any interesting things written about themselves. Or you can always pick on a conversation based on their interests. If there is nothing listed in their profile, then you can ask about their interests and how they spend their free time. If travel is their interest, then talk about places they have visited and ask about interesting incidents on their travel. There are lots of topic you can pick on. Chat decently and respect them. If they don't respond, then there is no point pestering them. If they respond, that means they have some interests on you (maybe, based on your profile pictures or how you have made the first impression with your messages). Never ask for their contact number after a few chats. Give them time. One reason a lady is in chatting apps is because she is looking around, not necessarily for sex but to hang out with someone with common interests. The first task is to make them feel comfortable with you chatting. If she is good looking, chances are that there are many guys after her, so your patience counts. Like I said earlier, if she is worth it, wait for it. Try to update them on some of your activities, like pictures of movie tickets, places you eat out. She might respond positively on that, like 'I have not seen movie in a long time' or '...eaten out in a proper restaurant'. Those are few positive signs. If she agrees to go out for a movie, it still gives you no right to stretch out your arms in the darkness on the first day out for movie. If she rubs her arms against yours, then you may ask her if it is ok to hold her hands. If she agrees, then you are already half way there. Treat them with respect and they will reciprocate. Next time, she will be asking you out for movies. Try to ask her out for dinner for the first meet up and make sure you pay for that.

Disclaimer:
I am not a dating expert (nor do I claim to be one of them) but the above mentioned points are solely based on my experiences and my observations. It may work for some and it may not work for some, so kindly refrain from blaming me if things don't work out for you. I am sure some senior samsters can add on to what I have mentioned above.

At the end, enjoy your one life that you have BUT without regrets

[sockspender]

I've not dated mature ladies before but this thread is good for reference. Thanks TS.

[naan1974]

What you consider mature lady?
40 to 50 or >50
Is it true they all desperate to get marry or get laid, or both

[lobowolf]

Originally Posted by naan1974

What you consider mature lady?
40 to 50 or >50

There is no distinct age to define a mature lady but to me it is 35+.

Originally Posted by naan1974

Is it true they all desperate to get marry or get laid, or both

Based on my experience, not all mature ladies are desperate to get married or get laid.

[porscheclub]

Sounds like a gigolo in the making but must say this is a bloody good thread to get romantic with women rather than girls

Thanks for sharing TS

[newlywedbride]

Actually lady only wants companionship on the emotion side. She only gives in to sex when:
1) Sick
2) Depress or sad
3) Too happy

[spoonge]

In Japan, there’s an occupation relating to this. It’s known as ‘Host’ profession. They are providing ‘emotional needs’ rather than ‘physical need’.

A documentary on ‘Host’ profession by USA Vice Channel. Video runtime 12.58:

Every year, all Japanese Host Club will hold a ‘Host of The Year Award’ just like ‘Golden Horse Award’.

Another documentary on ‘King of Host’ by Japan Vice Channel. Video runtime 18.05 (Click ‘CC’ icon bottom right 4th for English subtitle):

[naan1974]

Originally Posted by newlywedbride

Actually lady only wants companionship on the emotion side. She only gives in to sex when:
1) Sick
2) Depress or sad
3) Too happy

Serious? you would give in to sex when you are sick, sad or very happy?
I know women will give in to sex even tho they are not horny when they are
feeling happy. Sad or sick? why?
Next time I will try on a sick or sad women, but something tell me I may get slap.

[newlywedbride]

Originally Posted by naan1974

Serious? you would give in to sex when you are sick, sad or very happy?
I know women will give in to sex even tho they are not horny when they are
feeling happy. Sad or sick? why?
Next time I will try on a sick or sad women, but something tell me I may get slap.

To make a lady submit to you, you have to fulfill her emotion first. Only lady with high testosterone level don’t require the emotion side. Make sure your immune system is strong enough for a sick lady.

[hamsapkwai]

Originally Posted by newlywedbride

To make a lady submit to you, you have to fulfill her emotion first. Only lady with high testosterone level don’t require the emotion side. Make sure your immune system is strong enough for a sick lady.

to make your hunt easier lady with high testosterone level can be easily identified with bulging muscles and hair on her chest

and oh yes a heavy manly voice too

[newlywedbride]

When a gentlemen cross-dresser; it turns on a lady. It’s kind of like having a sister partner. But this step can only be reveal at the later stage.

[jj_jj]

Originally Posted by hamsapkwai

to make your hunt easier lady with high testosterone level can be easily identified with bulging muscles and hair on her chest

and oh yes a heavy manly voice too

from bro ROCKERS' pix thread on indian ladies, may even have "giant" clit/mini "penis", hehe

[kraam]

good advice

[fluffykite]

Yep, Mature ladies are nice. V loving.

I had a FB 40+ yrs old when i was in my late 20s whom I met on tagged, was an expat but she went home already.
Sad thing is she cut off all contact after she went back. She's married and with kids as home so ya... sad.

The companionship was really great. Very intellectual also.