MILF/GILF Colleague

[elune]

This is my first time posting in this section. Pardon my ignorance, just wanna see views from fellow samsters over here.

So I have a female colleague in her late 50s, she hot for someone her age, Im in my mid 30s.

We were seated in different office, so we didnt talk much during the first few years. The reshuffling of seating arrangement brought us closer. Shes sitting close to me and we started talking a lot. And she would occassionally join me for lunch.

I noticed that she dress rather sexier on days when shes joining me for lunch. I may be thinking too much but there are cases whereby i can see her down blouse. Not sure if shes doing it on purpose.

How do I know if shes interested in me?

Thanks in advance

[SchoolOfLife]

Originally Posted by elune

How do I know if shes interested in me?

Try to setup some after work activity with her and you only like a drink at a bar or movie with her only, if she goes, probably she is interested, if she gives excuses, probably she is not in my personal opinion

[Fbtak]

Depends on whether she's married. If she is not, I would be more aggressive. Ask her out for mid-day kopi or lunch. Basically, just treat it like you are chasing after any girl. Whether she is 40 50 or 60 does not matter. Slowly get to know her and take it from there.

If she's married, and together with the fact that you are colleagues, I say not worth. Just enjoy her downblouse can liao. If she's really interested, then let her come to you. But safer not to make the first move.

[bignehneh]

Usually those in their 50s or 60s and single need a lot of love one. So hehe! The 小鲜肉 will get eaten till no juice. But you need to be very careful hor. Don’t later get the wrong signal then kana complain or scolded. These char bo sibei influential in office one. Later complain to super high level then you tio pok. Or later if backfired, they got around tell people you 癞蛤蟆想吃天鹅肉. Then you probably lose your face

On the flip side, if they really like you, then sibei song… you got both wealth and sex

[GradiusLu]

IMOP, just go for it. I myself have done it a few times with the oldies in my office. Be it married or not, just enjoy the moment. Be it a fling or not, u got nothin to lose anyway. But of cos don’t overdo it till you kana complain la. 见好就收。If at any point u think she’s not into u, just stop. If she is, den go for it.

The best is to ask her out after office hour, not during. If she agrees to your date a few times means it’s pretty obvious she’s into u already. Cos frm wat I know, oldies won’t wanna waste their precious after office hours with someone not impt. If she’s willing to spend it with u, means got chance. The rest will have to leave it with your charm and charisma already. Most of them just wanna get the feel of getting wooed again like young girls. Trust me. Been there, down that. Just sweet talk moderately. Find out more abt their interest and target it frm there. Do your homework adequately and they will get hooked. Good luck!

[donut88]

Originally Posted by elune

This is my first time posting in this section. Pardon my ignorance, just wanna see views from fellow samsters over here.

So I have a female colleague in her late 50s, she hot for someone her age, Im in my mid 30s.

We were seated in different office, so we didnt talk much during the first few years. The reshuffling of seating arrangement brought us closer. Shes sitting close to me and we started talking a lot. And she would occassionally join me for lunch.

I noticed that she dress rather sexier on days when shes joining me for lunch. I may be thinking too much but there are cases whereby i can see her down blouse. Not sure if shes doing it on purpose.

How do I know if shes interested in me?

Thanks in advance

She's probably a cougar looking for young meat.

But since you all r colleagues, don't risk your career.

Best is to be cautious in your moves. U must able to read her and size her up first. Is she a potential trouble maker? Will she make a complaint about u?

Is she married?

I know of a case, the wife was having a fling with a colleague. Her hubby somehow found out. He wrote a complaint to her HR department. The male colleague got sacked immediately.

So such things might happen. So be cautious.

[loneyheart]

It always started with dinner instead of lunch ... follow thru the flow if any

[unwanted333]

Go for it… probably hinting and tempting you

Support cos I am a milf lover too

[kt88_2]

I also loves milf

[Bangster]

Originally Posted by elune

...So I have a female colleague in her late 50s, she hot for someone her age, Im in my mid 30s.

I noticed that she dress rather sexier on days when shes joining me for lunch. I may be thinking too much but there are cases whereby i can see her down blouse. Not sure if shes doing it on purpose.

Got pic?

Get ready lube. Have it dropped out of your desk, or bag, on purpose to make sure she sees it. Conversation topic starter. Take it from there Tiger

[elune]

Originally Posted by Fbtak

Depends on whether she's married. If she is not, I would be more aggressive. Ask her out for mid-day kopi or lunch. Basically, just treat it like you are chasing after any girl. Whether she is 40 50 or 60 does not matter. Slowly get to know her and take it from there.

If she's married, and together with the fact that you are colleagues, I say not worth. Just enjoy her downblouse can liao. If she's really interested, then let her come to you. But safer not to make the first move.

Yap.Shes married sadly.

[elune]

Originally Posted by bignehneh

Usually those in their 50s or 60s and single need a lot of love one. So hehe! The 小鲜肉 will get eaten till no juice. But you need to be very careful hor. Don’t later get the wrong signal then kana complain or scolded. These char bo sibei influential in office one. Later complain to super high level then you tio pok. Or later if backfired, they got around tell people you 癞蛤蟆想吃天鹅肉. Then you probably lose your face

On the flip side, if they really like you, then sibei song… you got both wealth and sex

Shes married but i think shes enjoying the attention im giving her. Like when we are out for lunch with other colleagues, she would almost 100% sit next to me or share my food.

Im only afraid that im overthinking. Hahah

[elune]

Originally Posted by GradiusLu

IMOP, just go for it. I myself have done it a few times with the oldies in my office. Be it married or not, just enjoy the moment. Be it a fling or not, u got nothin to lose anyway. But of cos don’t overdo it till you kana complain la. 见好就收。If at any point u think she’s not into u, just stop. If she is, den go for it.

The best is to ask her out after office hour, not during. If she agrees to your date a few times means it’s pretty obvious she’s into u already. Cos frm wat I know, oldies won’t wanna waste their precious after office hours with someone not impt. If she’s willing to spend it with u, means got chance. The rest will have to leave it with your charm and charisma already. Most of them just wanna get the feel of getting wooed again like young girls. Trust me. Been there, down that. Just sweet talk moderately. Find out more abt their interest and target it frm there. Do your homework adequately and they will get hooked. Good luck!

What you say is true. I did comment that shes pretty and dont look her age. She seems to like it a lot. I will try to compliment her more and see how it goes

[HonkyTonkyMan]

Originally Posted by elune

This is my first time posting in this section. Pardon my ignorance, just wanna see views from fellow samsters over here.

So I have a female colleague in her late 50s, she hot for someone her age, Im in my mid 30s.

We were seated in different office, so we didnt talk much during the first few years. The reshuffling of seating arrangement brought us closer. Shes sitting close to me and we started talking a lot. And she would occassionally join me for lunch.

I noticed that she dress rather sexier on days when shes joining me for lunch. I may be thinking too much but there are cases whereby i can see her down blouse. Not sure if shes doing it on purpose.

How do I know if shes interested in me?

Thanks in advance

Depends on how comfortable you think she is with you, you might drop subtle hints on her dressing ie....

[elune]

Originally Posted by HonkyTonkyMan

Depends on how comfortable you think she is with you, you might drop subtle hints on her dressing ie....

Thats what i feel too. On days we have preplanned lunch, she will be dressed in deep V shirt. Not sure whether is it a coincidence or she did it on purpose.

Theres once she was dressed in normal looking blouse but the top part of the blouse kind of opens up a lot when she bend over. I stole a glance, not sure whether she noticed it but later in the afternoon, she passed a document across our table by stretching and bending over, she looked down at her table while doing that, presumably to allow me to have a better look at her downblouse?