Dating mature ladies (My Encounters and suggestions)

[lobowolf]

Originally Posted by hugs

And cuddle up on sofa mmm..and you read to me
btw, it was really nice to see u dropped by my thread earlier. I was surprised but touched
did i woke u earlier? did i do that again? sleep some ..pls?

Looks like we have been touching each other by words ....Hehe. Nah! Waiting for my laundry to be done, so pretty much awake...

[hugs]

I'll pretend your laundry is keeping you awake And.. i'm safe, out of the dark. Watching "when in Rome" on tv.

Originally Posted by lobowolf

Looks like we have been touching each other by words ....Hehe. Nah! Waiting for my laundry to be done, so pretty much awake...

[lobowolf]

Originally Posted by hugs

I'll pretend your laundry is keeping you awake And.. i'm safe, out of the dark. Watching "when in Rome" on tv.

Such an obedient girl (you should be rewarded ), daddy is very proud of you.

I'm listening to the song 'The Young One' by Cliff Richard, playing at the background

Let me hum the song to you
---------------------------------------
And young ones shouldn't be afraid.

To live, love
While the flame is strong,
For we won't be the young ones very long.

Tomorrow,
Why wait till tomorrow,
Tomorrow sometimes never comes.
Love, me,
There's a song to be sung
And the best time is to sing while we're young.......
---------------------------------------

[hugs]

I'm getting increasingly curious about how do u look like. (Woke by my phone light blinking)

Originally Posted by lobowolf

Such an obedient girl (you should be rewarded ), daddy is very proud of you.

I'm listening to the song 'The Young One' by Cliff Richard, playing at the background

Let me hum the song to you
---------------------------------------
And young ones shouldn't be afraid.

To live, love
While the flame is strong,
For we won't be the young ones very long.

Tomorrow,
Why wait till tomorrow,
Tomorrow sometimes never comes.
Love, me,
There's a song to be sung
And the best time is to sing while we're young.......
---------------------------------------

[hugs]

How do u look like? I hope you are not good looking haha. And i know you are not a Gemini

Originally Posted by lobowolf

Such an obedient girl (you should be rewarded ), daddy is very proud of you.

I'm listening to the song 'The Young One' by Cliff Richard, playing at the background

Let me hum the song to you
---------------------------------------
And young ones shouldn't be afraid.

To live, love
While the flame is strong,
For we won't be the young ones very long.

Tomorrow,
Why wait till tomorrow,
Tomorrow sometimes never comes.
Love, me,
There's a song to be sung
And the best time is to sing while we're young.......
---------------------------------------

[crak]

Originally Posted by 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.....

Like a JIE JIE (elder sister) take care of you.

Isnt that good/


"O"

[hugs]

Like the idea?

Originally Posted by crak

Like a JIE JIE (elder sister) take care of you.

Isnt that good/


"O"

[lobowolf]

Originally Posted by hugs

I'm getting increasingly curious about how do u look like. (Woke by my phone light blinking)

I don't know how to put it but I do have all the attributes that make up a regular face Just a regular Joe, whom you wouldn't bother giving a second look and I like that anonymity

[lobowolf]

Originally Posted by crak

Like a JIE JIE (elder sister) take care of you.

Isnt that good/


"O"

You should have a relationship with a mature lady to know what it is like. They are wonderful

[hugs]

Regular Joe with interesting experiences n good writing. I'm just anonymous as you or maybe more. Regular Joe, your laundry was on my mind

Originally Posted by lobowolf

I don't know how to put it but I do have all the attributes that make up a regular face Just a regular Joe, whom you wouldn't bother ving a second look and I like that anonymity

[fluffykite]

Originally Posted by hugs

Like the idea?

Yeah I like... I like to take care of matured ladies who takes care of me. Be there for them, listen to them, tease them sometimes, see them laugh... so cute.

[hugs]

Your.. .com says otherwise.

Originally Posted by fluffykite

Yeah I like... I like to take care of matured ladies who takes care of me. Be there for them, listen to them, tease them sometimes, see them laugh... so cute.

[lobowolf]

Originally Posted by hugs

Regular Joe with interesting experiences n good writing. I'm just anonymous as you or maybe more. Regular Joe, your laundry was on my mind

I noticed that you left behind your foot prints behind last night . I hope you felt at home, though I was not there to host you . How is your long weekend coming along?

[hugs]

Yup. Came. Nobody's home so i left.

Originally Posted by lobowolf

I noticed that you left behind your foot prints behind last night . I hope you felt at home, though I was not there to host you . How is your long weekend coming along?

[lobowolf]

Originally Posted by hugs

Yup. Came. Nobody's home so i left.

Aww... So sorry about that but I left the door open for you to come in. Hmm ... I'll be at home tonight to greet you and to serve you a drink and also show you my book collection. You can pick one and read through it. I'll keep the cushion ready too