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]

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]

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]

...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]

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]

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]

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]

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]

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?

[ilovepantyhose]

hi TS,

what is your position in the company?

if u hold high rank, do think thrice before "taking the plunge"

:p;)

[elune]

hi TS,

what is your position in the company?

if u hold high rank, do think thrice before "taking the plunge"

:p;)

Not really high but higher than her. I have more to lose as compared to her to be honest.

[cupid xpress]

Hi TS, thee next post from you, hopefully it's some sexual encounter with her hor....

TIA

[elune]

Hi TS, thee next post from you, hopefully it's some sexual encounter with her hor....

TIA

I will try but wont take it too fast. Will test water first.

[Tai_zi21]

Just do it…. The longer u drag the sparks will be gone

Just my 0.01 cent view

Cheers

[r.fowler]

no woman will say no to compliments. go for it. but dont overdo it. dont act like a simp.

[pacerman]

stay clam an relex

[kt88_2]

Mature woman the best,can be real good buddies

[vitroman]

All the best bro and hope to hear good news!

[xylphz]

All the best bro and hope to hear good news!

Upz u +13 pam pams !

[elune]

Im getting mix feeling these few days, she didnt sit next to me but maintained eye contact for a really long time during our conversation (signs of a female into you?) Or maybe im thinking too much.

Bros have any idea what kind of question i can ask to test water?

[donut88]

Im getting mix feeling these few days, she didnt sit next to me but maintained eye contact for a really long time during our conversation (signs of a female into you?) Or maybe im thinking too much.

Bros have any idea what kind of question i can ask to test water?

Eye contact means she's v interested in you. Body language tells everything

But be v careful since your career is involved. I won't jump in readily.

[elune]

Eye contact means she's v interested in you. Body language tells everything

But be v careful since your career is involved. I won't jump in readily.

We basically maintained eye contact for more than 10sec. To a point i felt shy and looked away. I get what you mean, which is why im hesistant at the moment.

[entering]

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

If your industry is a niche one or everyone knows everyone, if this goes south, you'll have a lot of problems with future work.

I've some colleagues who went and had sex with other colleagues and turned out now no one wants them back in the industry.

So, you'll need to ensure you can tackle this issue first if you want to poke anyone. For me, I have had students and colleagues as well. But the thing is, I move in between 3 industries, whenever I resign (also to ride out the non compete clause in my contracts. Some as long as 1 year). First industry , I quit, I apply to the second, then if I quit, the third.

By the time I'm back in the first industry, no one recognises me.

So, better plan ahead.

[donut88]

We basically maintained eye contact for more than 10sec. To a point i felt shy and looked away. I get what you mean, which is why im hesistant at the moment.

More than 10 secs, confirm she's into you. Lol

[sky_liner2]

Good thing is TS can do her raw since she may has way passed her menstruation.

[elune]

More than 10 secs, confirm she's into you. Lol

Or it could just be basic courtesy. Hahah
Its throughout our conversation that she looked right into my eyes for more than 10 sec while speaking. Cant rmb what topic we were on.

Im a lil bit hesistant at the moment to proceed further, worrying it might just be 1 sided

[sdol v2]

Im a lil bit hesistant at the moment to proceed further, worrying it might just be 1 sided

Since u noticed her dress differently when she has lunch with u, why not compliment her for it, or comment about it? It can sound like just an innocent comment.. if she has something up her sleeve u will know

[naan1974]

Bro, i have had my fair share of relationship with much older women.
just to let you know, regardless of their age, older women
bring you up fast and bring you down faster. No need to guess too
much. they usually dont hide if they are into you. just be assertive and
grab when presented to you. They usually wont hang around waiting for you,
once signal is there grab or she will be gone like a wind.

"I noticed that she dress rather sexier on days when shes joining me for lunch"

just pointblank tell her" is it me or you simply look so sexy today "


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

[elune]

The compliment would have been easier if its not a group lunch. Haha

[jonjonjo]

ask her out bro, it might be your craziest life adventure, who knows? yolo

[jien1]

Interested to know what's coming up! She sounds like a catch

[bensonbeh]

I will start with accidentally touch her hand when passing things like document, stapler, pen. gently say sorry but look her into her eyes. If she likes you, body touches should be fine. If her response is smiling and also look at you. High chance you can tackle her. How deep this should proceed, it depends on you. But since she is married, i guess you need to date her really low profile.

[seylen]

It's cool to read that.

[devamona]

Oh, I love stories like this. So curious to see what happens next. She definitely likes you or wants to play with you. Recently, my bestie and I were discussing a colleague of hers who hooks up with guys half her age. I'll be honest, bestie and I judge her because she's a teacher. And as you can understand, her boyfriends are high school boys. Fans of Mom Porn Love (https://mompornlove.com/), damn it! She's really old enough to be a mom to her lovers. But when everyone involved is an adult, then it's a nice exciting experience. So I think you and she have almost no stop signs. Except that she's married. Although who's ever stopped a marriage? So go ahead and have a wonderful time together!

[HonkyTonkyMan]

Oh, I love stories like this. So curious to see what happens next. She definitely likes you or wants to play with you. Recently, my bestie and I were discussing a colleague of hers who hooks up with guys half her age. I'll be honest, bestie and I judge her because she's a teacher. And as you can understand, her boyfriends are high school boys. Fans of Mom Porn Love (https://mompornlove.com/), damn it! She's really old enough to be a mom to her lovers. But when everyone involved is an adult, then it's a nice exciting experience. So I think you and she have almost no stop signs. Except that she's married. Although who's ever stopped a marriage? So go ahead and have a wonderful time together!

Oh, I love stories like this. So curious to see what happens next. She definitely likes you or wants to play with you. Recently, my bestie and I were discussing a colleague of hers who hooks up with guys half her age. I'll be honest, bestie and I judge her because she's a teacher. And as you can understand, her boyfriends are high school boys. Fans of Mom Porn Love, damn it! She's really old enough to be a mom to her lovers. But when everyone involved is an adult, then it's a nice exciting experience. So I think you and she have almost no stop signs. Except that she's married. Although who's ever stopped a marriage? So go ahead and have a wonderful time together!

wow must be identical twins:D

[sky_liner2]

wow must be identical twins:D

Yes, cloned accounts with exact same posting.

[klsgman]

Maybe lady at these age her husband have very less or no sex life already for them. But they also need it too, if there is a 小鲜肉 infront of her why waste it

[elune]

I will start with accidentally touch her hand when passing things like document, stapler, pen. gently say sorry but look her into her eyes. If she likes you, body touches should be fine. If her response is smiling and also look at you. High chance you can tackle her. How deep this should proceed, it depends on you. But since she is married, i guess you need to date her really low profile.

There has been a few accidental touches. Like really accidentally. We tried to take the same thing and our hands touched. I didnt say anything and didnt see her reaction.

The tricky part is its group lunch. Only time i can talk to her privately is through Whatsapp and sometimes her reply abit short and non continuing.

[shakethemtatas]

There has been a few accidental touches. Like really accidentally. We tried to take the same thing and our hands touched. I didnt say anything and didnt see her reaction.

The tricky part is its group lunch. Only time i can talk to her privately is through Whatsapp and sometimes her reply abit short and non continuing.

group lunch can be fun, touchy2 down there below the table eh:D

[Specialboy]

TS, if you drive, make up some story that you are going somewhere near her place, then offer to drive her home lah!
Create your own opportunity to take the conversation or relationship to the next level.

[tagokir89]

let it pass

[elune]

TS, if you drive, make up some story that you are going somewhere near her place, then offer to drive her home lah!
Create your own opportunity to take the conversation or relationship to the next level.

Problem is she drives and i dont. Haha

[jonjonjo]

Good thing is TS can do her raw since she may has way passed her menstruation.

LOL. chance of pregnancy is still there although low.

[Specialboy]

Problem is she drives and i dont. Haha

Doesn't matter la! Make excuse you are going somewhere near her place to collect something, ask her if she can drop you off at the nearby mrt stn.

[elune]

Doesn't matter la! Make excuse you are going somewhere near her place to collect something, ask her if she can drop you off at the nearby mrt stn.

Actually now that i think back, i probably missed a golden opportunity. She wanted to pass me something but i rejected since i already have it. Should have accepted and took the chance to collect from her home.

[naan1974]

Actually now that i think back, i probably missed a golden opportunity. She wanted to pass me something but i rejected since i already have it. Should have accepted and took the chance to collect from her home.

delay no more ! once she flew past she's gone.
and she will tell you
"if you drop by that night, i will have fuck you":D

[realcow]

Lau kway bu tonic is still the best!! Esp the wolf age women.....pussy always wet.....rip off the panty and lick it dry....let her suck your hard rock cock...make her swallow the cum....then vibrate her pussy for half hour....she ll be your sex toy for years!!! Lau kway bu tonic still the best!!!

[lipe]

bro realcow


up you 20 points

my partner (ex colleague) from 22 years old to 55 years old, still going on strong.


Lau kway bu tonic is still the best!! Esp the wolf age women.....pussy always wet.....rip off the panty and lick it dry....let her suck your hard rock cock...make her swallow the cum....then vibrate her pussy for half hour....she ll be your sex toy for years!!! Lau kway bu tonic still the best!!!

[justin69]

Actually now that i think back, i probably missed a golden opportunity. She wanted to pass me something but i rejected since i already have it. Should have accepted and took the chance to collect from her home.

You can always ask her if the thing is still available and you would like to see it because you intend to replace your current one. 😊

[KimSiew769]

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

Look out for body language when u r with her.
Does she casually touch u or play with her hair, or does she share anything private with you?
its pretty easy to spot body language if they are interested in you

My 2 cents, its abit harder for MILF or GILF to show "signs" even if they are interested - u just have to pay attention to how she react when she is near u

[GradiusLu]

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

Yo bro, any updates abt ur colleague so far? Any progress?

[thor1981]

recently met a colleague's client who is a gilf (early 50s) and jap.

she's a divorced OL, i asked her out w/o telling colleague. live sg 15+ years.

nice dinner, fuck in her condo, CIP raw, damn shiok. gilf benefit, more open to CIP.

planning to meet her next week again after her biz trip :D

[CowardPotato]

recently met a colleague's client who is a gilf (early 50s) and jap.

she's a divorced OL, i asked her out w/o telling colleague. live sg 15+ years.

nice dinner, fuck in her condo, CIP raw, damn shiok. gilf benefit, more open to CIP.

planning to meet her next week again after her biz trip :D

TS hoseh:D dare dare go

[keith79]

Have been having sex with my colleague during the 4th month of her pregnancy till today after she recently give birth. Initially with condom on and then proceed to raw. Really enjoying the moment of fucking a pregnant colleague and now drinking her breast milk. Hopefully this will go on for a long time.

[sky_liner2]

recently met a colleague's client who is a gilf (early 50s) and jap.

she's a divorced OL, i asked her out w/o telling colleague. live sg 15+ years.

nice dinner, fuck in her condo, CIP raw, damn shiok. gilf benefit, more open to CIP.

planning to meet her next week again after her biz trip :D

Way to go bro, early 50 is good not too old de, consider as MILF to me.

[AdmiralR]

recently met a colleague's client who is a gilf (early 50s) and jap.

she's a divorced OL, i asked her out w/o telling colleague. live sg 15+ years.

nice dinner, fuck in her condo, CIP raw, damn shiok. gilf benefit, more open to CIP.

planning to meet her next week again after her biz trip :D

Very true, older ones are more open to CIP which is such a bonus

[Griff]

Well, she is definitely not a colleague, but a gilf I have the hots for.
At her age, still really foxy looking :D

654536


Christine Lagarde, 68 years old this year :o:o

[loneyheart]

https://www.youtube.com/watch?v=i-O5z0Q-KLk

[kt88_2]

Way to go bro, early 50 is good not too old de, consider as MILF to me.

Lol can enjoy n cip with worries

[thor1981]

Very true, older ones are more open to CIP which is such a bonus

yes. discovered 50+ ok to CIP once they know you are healty.

[kt88_2]

For me Iike 50s, great with them or even 40s

[Thehardone]

Had a ex colleague 3 years my senior. Still well kept, nvr did I knew once the sexual button is activated, she is really wild. Her bj is really out of the world and I always cums in her mouth and she swallows.

Sex with her is not that bad but pales to the younger MILF FB. But well, get to cum in pussy with a MILF, nothing to complain.

[fuckjedi]

Many years ago I was working in retail and for a prominent video rental company and there were 2 Chinese Malaysian girls who were working the same outlet as me. One of them was a senior staff.

They were both of average looks but they love to dress up to tease and one day we were at a team gathering at a chalet in Pasir Ris and the 3 of us ended up sharing a cab home (Uber and Grab didn’t exist yet).

I stayed in Bedok and these 2 girls stayed in a shared room further down at Upper East Coast Road and in the cab all 3 of us sat at the back, me in the middle flanked by the other 2 on either side. As usual they were wearing very skimpy outfits and because we were all drinking, we were very tipsy by the time we got into the cab.

So we started laughing and giggling and then we started getting touchy with one another. Because I was supposed to drop off first, the cab stopped at my Blk. I whispered to one of the girls (the sluttier one between the 2) in the ear and I said “let’s go up and fuck. NOW”

Long story short, I managed to drag them up to my place (I was staying in a rented flat on my own) and the moment we got inside we started taking our clothes off. It was their first time doing a threesome but they attacked me like as if they were very experienced already.

Fucked both of their brains out and I made sure I came in both their mouths. Then when I had finished shooting my cum they both looked at me and I said to them “you both have been cock teasing me for so long now I’ve fucked both your brains out.” They ended up staying the night and all 3 of us slept together and showered together the next day before going to work together :)

[178noobnoob]

Many years ago I was working in retail and for a prominent video rental company and there were 2 Chinese Malaysian girls who were working the same outlet as me. One of them was a senior staff.

They were both of average looks but they love to dress up to tease and one day we were at a team gathering at a chalet in Pasir Ris and the 3 of us ended up sharing a cab home (Uber and Grab didn’t exist yet).

I stayed in Bedok and these 2 girls stayed in a shared room further down at Upper East Coast Road and in the cab all 3 of us sat at the back, me in the middle flanked by the other 2 on either side. As usual they were wearing very skimpy outfits and because we were all drinking, we were very tipsy by the time we got into the cab.

So we started laughing and giggling and then we started getting touchy with one another. Because I was supposed to drop off first, the cab stopped at my Blk. I whispered to one of the girls (the sluttier one between the 2) in the ear and I said “let’s go up and fuck. NOW”

Long story short, I managed to drag them up to my place (I was staying in a rented flat on my own) and the moment we got inside we started taking our clothes off. It was their first time doing a threesome but they attacked me like as if they were very experienced already.

Fucked both of their brains out and I made sure I came in both their mouths. Then when I had finished shooting my cum they both looked at me and I said to them “you both have been cock teasing me for so long now I’ve fucked both your brains out.” They ended up staying the night and all 3 of us slept together and showered together the next day before going to work together :)

I had a malaysian chinese before as well. Damn horny. But not in contact anymore. Now want to hunt back. :(

[fuckjedi]

I had a malaysian chinese before as well. Damn horny. But not in contact anymore. Now want to hunt back. :(

These 2 girls are already married. They’re still in my fb contacts :)

[178noobnoob]

These 2 girls are already married. They’re still in my fb contacts :)

That’s nice to have. I didnt add her on fb. Cause after awhile, realise she just need to be ‘filled’

Sometimes will still get news on her. But more on a negative side

[gunzcarbine]

Thanks for sharing.