Me: 28 year old guy
Her: my 40 something deputy-boss, divorced, partner, kids, work focused but held back/frustrated, MILF
Background & stuff:
She has referred to me as a mommys boy in the past. Obviously not good. Though she also finds me smart, ambitious and extremely honest. Recently we talked about past clubbing, she also mentioned a place I'd been to thats now a strip club, I joked I'd have to go again and she laughed. Also recently we got into a conversation during a work meeting about her being a milf/cougar and when asked how young is too young she said at least over 18. Just giving this as background detail as we've been getting into some less than professional conversations lately.

Also, talked about ex's, here I fucked up (further probably) by appearing wounded by it to which she quickly bumped me into the 'I'm here as a friend if you need to talk' category (which is better than the 'work guy only' category I was in).

I've been reading a lot of stuff on this site, I should probably explain my aim here, I don't necessarily want a relationship with her, but would like to take her out places as friends but also make it known that I can be discreet and that I find her attractive and that I'm interested in some no strings attached fun if she is.

I've read stuff on here that as an escalation method think it was called the BOMB might be an option it involved saying something like, "I want to know what's fun for you, what makes you smile, what turns you on, WHAT MAKES YOU CRAZY AND SOAKING WET, I want to know what it takes to make you laugh, I want to know everything."

She's level headed but I don't want to lose my job if she freaks out over something like that. I guess what I'm asking here is if anyone has any opinions on what/where I should take this next.

I've also considered a dhv(?) employing a trick(for want of better word) from another site that involved making her feel strong positive then negative emotions over something, I considered a story about holding a friends baby for the first time but that it died later.

I'd like to get her out just the two of us in some social way, as so far it's been either at work or via text. For a drink so we could talk, to a casino so I can sarge(?), swimming so I can make my attraction obvious.

Althought I've used some of the pua terms in here I dont know this game as you can probably tell, I'm not trying to mess up her life or relationship either, I just think she's bored and would like her to have fun with me whether it leads to anything sexual or not.

The fact that shes 40 makes everything much simpler in general. These woman don't tend to play games much in my experience. You basic gameplan is fundamentally correct, isolate then BOMB her (or their equivalents)

Ok here is what I would do.

Ask her out for a drink to discuss "business, office politics, and whatnot"

if she agrees then you should assume she wants sex given your situation.

The best way ive found to do this with MILF is to immediately start telling sexual stories and go through a lascivious and salacious routine statck. She will likely get immediately responsive and excited, in which case ask her to come home for a drink. That should work assuming she will come out with you for a drink. Older woman don't tend to go out with guys they don't plan on fucking. If she wont agree to go out for a drink then freeze her out and re-engage later as appropriate.

A couple questions before I respond... how experienced are you with reading people? Have you hooked up with co-workers before? Have you dated a lot of women?

The only reason I bring this up is because, if I understood your email, you work with this girl. If that is accurate, I'd recommend having her make the moves. You just set up the play.

That said, it seems you have working your way into her mind, which is a comfortable spot to live. It's essential that you make yourself at home here, and make her comfortable with it too. How to do this:

Get her out of work mode. It sounds like she is a boss something of you? So you need to get her out of that mindset. Take that power away from her by introducing your own variables. We often use a grill-n-chill concept, or movie night idea for women like this. In a nutshell, be assumptive.

"I told you we're doing that grill out on Saturday right? Can't remember since I always forget to invite people. I was thinking you could get to my place around 6:30 and we'll head out from there. You can bring some hot dog buns, right?"

Of course she didn't know about this fake event yet, but if you are confident, and she doesn't have other plans, she should go with it. The best thing about this kind of planning is that you can create the event after you get her commitment. If she can't make it to this one, apologize that you forgot about her and offer to make it up. Tell her you'll take her out to do something fun really soon, and find out what her next night open is. Don't make plans, but say something like how "that should work" and thread to another topic.

As for when you hang out, make sure you have a great mind set (thus if you can incorporate other friends), tell great stories, have lots of jokes, and follow the usual M3 tactics. Make sure there is lots of kino. When you get back to her place, keep it moving until she goes for the kiss. Since she is your boss, she is now the one that gets in trouble should HR catch wind.

We have all sorts of stories like this in our book. If you get a chance, check them out. Hope this helps.

_________________
If you like to swim in treasure like Uncle Scrooge after a tough day in Duckburg, you will love my book The Journal!

We have all sorts of useful and essential advice about women. Pick up your copy at http://thejournalbook.com/download_e-book/

Thanks guys.

To the questions, I think I read people well, never hooked up with a coworker before, haven't dated a lot either, however, I've had a bit of a personality transplant this year (or rather a re-establishment of confidence) wont go into details but basically most of the stuff that held me back has gone and I feel comfortable in situations that I didn't used to...

So I'm quite confident in trying to set up some sort of date or going for the kill as it were. Also because of the conversations we've had so far I think it's going to be easy to escalate into sexual talk.

I'm just wondering with the other factors involved (her relationship and her being my boss) if there are things I haven't considered, such as does she know she can trust me not to tell everyone should something happen (obviously you guys dont know that I just mean is there a technique to make SURE she knows it before I go in bombing), also you made it sound like theres other methods than the BOMB?


Thanks again guys, I'm doing a night shift with her Tuesday so I'm thinking I'll try and get a date then after some conversation. If I've read right I should either be kinda nonplussed about it, or not directly invite her just say I'm doing x so she wonders why I didn't invite her.

Sorry, another question based on a couple of things I've read on here, at the moment things stand as work colleauges, text friends and some kino (hugging). After a lot of back and forth texting all day Christmas day when she was at work then home with her guy and parents.

I thought maybe I should not text her boxing day to see if she 'misses' my texts. or... do you think I should text her a lot to keep in her head?

I don't even know what BOMB is but ya escalation, if done right, is gold on olde woman. I actually am against most public Kino escalation, but that's an advanced topic. I'm just like to say "BOMB" her as a analogue for sexual escalation, verbal or physical, its a funny term. Dropping bombs on your moms.


Also I suggest you text her not put her on the spot verbally for a date, as your boss this is better logistically. Also bravo on using "nonplussed " I thought I was the only one in here who bandys that word about.

As far as your text question, vary the length, pauses, and durations of your texts. So disappearing for a couple days on texting normally raises attraction, don't be predictable or dependable, its boring, girls hate boring.

Sounds good, thanks.

Bombing was from something I read on here, dunno if it was an offical phrase but yeah ya took the meaning.

I'm planing on saying something like "I want to know what you think, I want to know what you feel, I want to know how you feel, I want to know what makes your skin tingle and your fanny throb (I'm English it can also mean same as pussy here), I want to know what makes you wet, but most of all... most of all [name], I want to eat your pussy like it's a juicy steak/like it's the antidote/like I'm looking for Chillean miners etc.

Appreciate the help.

if you can pull that fanny stuff off it would be funny and may even be effective.

I always hide combine my DHV stories with sexcapade type stuff, I calibrate how graphic I become based on how they react. If they seem intrigued in a turned on, or even in an appalled way, I get more and more sexual. If they get more standoffish and reserved I back off.

You are suggesting saying this through a text message? A text message that she could use to get you fired? Potentially thrown in jail with? Remember that humor can be hard to construct through a text message. Those smiley faces just don't do a PUA justice.

Since she is your boss, I would suggest maintaining plausible deniability.

Now that I think about it, this all happened last night, right? So I'm late to the party. Not even fashionably. Before I go further, I'm curious if there were any developments.

_________________
If you like to swim in treasure like Uncle Scrooge after a tough day in Duckburg, you will love my book The Journal!

We have all sorts of useful and essential advice about women. Pick up your copy at http://thejournalbook.com/download_e-book/

There were some developments.

We were at work, out of the blue I get asked if I've heard a rumour about her having an affair with another member of staff (by her and some day staff who haven't left yet), I'll get back to that later. Later... We start bantering via text... it eventually stops, she goes up to do a sleep-in shift while I'm on waking duties, but I know she's going to be up for a while anyway, this follows:

Me: About this rumour stuff, I hadn't heard anything, but I want you to know I wouldn't pass it on if I had. True or not it'd be no one else's business. If I find out who's been saying it I'll let ya know... Have to say if you are having all these sordid affairs don't feel you have to leave me out! lol, I can keep a secret.

Her: I'm not sure if it was started by one particular spiteful person cause everyone I have asked has laughed and knows its stupid and thanks for the offer but not sure if I have the time or energy for an affair xxx

Me: Oh, I meant leave me out of knowing about it.

Her: x (her bf) knows his only competition has ever been my horses and no not in a kinky way but they have always been there xxx

Me: I can't say I'm not dissapointed, since you just put the idea in my head my mind was going a mile a minute! I imagine the rumours start because you're really really sexy. So really it's all your fault! (if I'm making you uncomfortable I'll stop?)

Her: Its flattering thank you i dont see myself as sexy just normal old me xxx

Me: I wish you could see you how I do. I'd try to explain if you wanted me to.

Her: Ok how do you see me xxx

Me: As a highly intelligent, vivacious, ambitious & classy lady. I want to be explicit if it's ok?

Her: I'm blushing now xxx

Me: Your figure is so womanly & feminine it's taking all my willpower not to come up there and devour you right now, like a juicy steak, ripe fruit or cream cake.

Me: I want to know what you think, how you feel, what makes your skin tingle and your fanny throb, I want to know what you fantasize about, what makes you wet, but most of all... most of all, I want you to use me to tongue fuck your pussy until you climax in my mouth.

I think at this point she fell asleep, and I had a sudden realisation that it could all backfire...

Me: I'm sorry, I shouldn't have said all this. Please forget it, I'll not speak to you like this again.

Off shift, got home just going to bed and...

Her: Some of what you said was beautiful but yeah some was offensive it's deleted now so water under the bridge have a good sleep xxx

Me: Sorry I got carried away, didn't mean to make it sound like thats what you are (sex object), just that I find you highly attractive, it's hard to stop thinking about you.

Me: Curious - what was beautiful & what was offensive?

Me: I feel like shit, I wanted to convey how desirable you are but think all I acheived was making your opinion of me drop to zero.

Me: I wasn't asking you to act on anything, I just like giving compliments.

Me: I don't think I can sleep with this on my mind. I had hoped my willingness to risk being done for sexual harassment would make it flatteringly apparent how pretty I find you.

Her: And some were lovely being compared to fruit and cream cakes was nice and how intelligent and womanly I am but knowing if you were making me wet wasn't, think we need to find you a gf so you can express all the nice things about you xxx

Her: Don't worry I am taking as a compliment xxx

Me: I meant to say I'd like to know what makes you wet, you excite me, and it makes me curious about what excites you.

Her: There are lots of things that excite me but I'm keeping that to myself thats the mystery of women xxx

Her: *sends me a random video of her horse*

Me: Lucky the horse?

Me: If I guess some, can I win some? *over eager expression!* (trying to make her laugh)

Her: No xxx

Me: Ok, heh, sorry. Worth a try. (thinking about it, the "no" could have been about the horses name - I was just going to use it to lead into... well you can guess)

Me: I want to take you for a drink to clear the air. You did say I had to take you for a drink when I got my car.

Her: Ok we can go for a drink xxx

Me: x time tonight, x place, where should I pick you up. Or now if you've not eaten their bacon sandwiches are goood! (it was past lunchtime by now)

No reply for while...

Her: Can't do tonight sorry xxx

Me: Ok, no worries. x just asked me to do a late shift, I had to turn it down I still haven't slept yet, heh.

Ya don't need to tell me I fucked up in several places lol, but surprisingly am still in going for a drink territory, which at least means I didn't end up in creepy territory. I decided to leave it there and not press her for a time because I was falling asleep.

I'm guessing I need to reopen, build, escalate again?

I probably went over board because, I kept offering her ways to stop what I was saying and she didn't take them in fact she seemed to be encouraging it. If she fell asleep when I guess she did she probably woke up and read it out of the blue and thought wtf.

Any advice on where to go from here (aside from afc hall of fame) would be greatly appreciated.

Bump.

Anything more guys plz?

Update.

We had another text conversation after the last one and before this, I asked her if she was in love (in the open ended sense of asking), she referred to her bf as a comfy old chair and that they argue a lot and she doesn't really know if she's been in love or not then asked my take on what love is, after explaining my views on it she asked if I'd ever just say it because I thought the other person wanted to hear it and also said that she has done before, I said nah that'd be cruel.

Few days later...

Me: Can I see you out of work some time?
Her: Sounds important I'm free this morning after doing xyz. xxx
Me: I just mean, sorry, never mind.
Her: You have something on your mind spill. xxx
Me: I can't stop thinking about you. I get the impression you think I'm a stupid kid or just trying it on with you.
Her: Your not stupid or a kid, sorry if ive given you the impression anything can happen between us, sadly im a flirt and your flattering remarks make me feel good about myself, i can be a friend but nothing more. xxx
Me: You haven't given me that impression. I want to flirt with you but didn't know how you felt about it after last time. I want to be close friends, take you to things YOU like to do that are exciting and fun for you, push your comfort zone a little, swimming, massages, casinos, buy you something sexy - not for me to see you in just to make you feel good, I want to give you you time to enjoy life instead of running around after everyone else. I don't know if giving you foot rubs and presents is out of the friend zone to you.
Her: I think that would be crossing the line.
Me: I like making you feel good because you deserve to.
Me: Your hair is ridiculously perfect.
Me: I tend to read blushing (from before) as go further.
Me: Though I like making you blush even if we can't.
Me: Is sending you explicit texts crossing the line, even if you only read and delete?
Me: I want to make you feel naughty and irresistable. I can be discreet about it.
Me: Anytime you wanted me to stop you'd only have to say, I want it to be fun for you and worry free.
Me: Would laying clothed on a bed in a hotel room while I tell you how pretty you are to me be?
Her: Yeah that would not be good either.
(in case it's not clear why I'm laying it on kinda thick when she's backing off and saying friends, I'm trying to put as many ideas as possible in her head. No idea if thats a good tactic or not.)
Me: I do understand how things are for you.
Me: Is it bad that I already have a "favourite" fantasy?

The next morning new years day she comes in and gives me a hug. I purposely make no comment about it (unlike first time) and go home. She texts me with an excuse to talk. (fishing for compliment?)

It still feels in a good place to me, maybe I'm seeing it wrong though, still haven't seen each other outside of work which is begining to bother me.

seems like your persistence could pay off, or it may get you fired. Perhaps both. You seem to have a lot of energy you may be able to wear her down.

Tell me how she responds to those texts about you putting imagery into it and explaining your fantasy, I have done something similar and it worked but not that extreme, and I would like to very badly so yea. Love to hear more about that.

_________________
Best of Luck
-Raphael

Aspiring Artist

Read the adventures I take as I discover my way towards becoming a mPUA or a dPUA (decent PUA) including completing the StyleChallenge ---> raphaels-journel-vt119594.html