First Run-In With an Older Woman

[someguyinachair]

Hey there, guys,

Before reading too far into this, I would like to let those of you who read this to know that I'm familiar with how forums generally work. I know that for the sake of preventing repetition and ensuring the smooth running of the site, that I should read all the sticky threads for each sub-forum and use the Search button. I'm aware that as a new poster, I have a higher likelihood of irritating veterans on this thread who have to dispense the same advice all the time.

So, just to let you know, I've been doing the above mentioned things, though admittedly not as thoroughly as you'd probably like newcomers to. The selfish side of me still would like to get specific feedback on my particular cougar/MILF case. Rather than infer from the potentially similar encounters of other posters on this board, I'd like to hear direct opinions concerning my own case. It just makes me feel... special.

For your convenience, you can simply refer to the very end of this post to read a summarized version of my predicament.

I'd like to say in advance that I will very much appreciate any feedback and advice as to a plan of action for closing the deal. I've only recently discovered this online subculture and previously had no idea just how calculated individuals could be in conducting themselves with women - and certainly didn't know that it went as deep as theory and embedded terminology that I've never heard of.

Anyway, on with the story... (again, a summarized, bullet point version of the story is at the end of this post)


The Story

Since June 17 of this year, I've been volunteering at a weekly internship at a sports facility every Wednesday (June 17 is also a Wednesday, of course). On my very first day, I met a woman who worked there as an assistant, and over the course of the subsequent weeks, I began getting to know her.

This coming Wednesday will be the 7th day that I have volunteered at the facility, but only the 5th day that I have actually seen her (she was off during two of the Wednesdays).

Since that time, I've learned that she is a 31-year-old single mom. She's told me a lot about her 8-year-old son. Also, she's recounted a lot about her college years, about how drunk she would get, to the point that she couldn't remember what she did or who she did.

As you can see, the sexual innuendo during our conversations was something she started, however subtle the hints were.

She's also told me that she tends to attract guys my age (22, 23, 24). I am 21.

Furthermore, she's found it comfortable to discuss her sex life with me. Until 4 months ago, she had been seeing a "friend with benefits." The fling lasted 4 years. Clearly, she doesn't want a relationship (and she's told me this).

However, he broke her one rule, which was to never show up at her house. Her private life is something she keeps from her young son. Apparently, her sex buddy became attached.

If you guys were to analyze this tidbit of information, would you possibly perceive this as a sign of a woman going out of her way to let me know that she is available?

Continuing with the story, I explicitly asked her if there was a chance that she'd ever be interested in having another friend with benefits. She told me yes, if she found someone else.

She's asked me how many kids I want to have later in life. Whether or not that is relevant, I don't know. But I'm trying to give out as much information as I can if it will help you to analyze the situation.

Over the course of the weeks, she's been tanning. When we first met, she was of normal white complexion.

Here is my personal take on this tanning business: in the 3 years she's worked at the facility, she hasn't tanned (at least I don't believe so; otherwise, she would have been apparently tanner during our first encounter). After my first day as a volunteer, she began tanning 2 weeks later.

I don't mean to sound egocentric, but maybe she did it to increase her appeal? It sounds egocentric, I know, but I'm trying to pick up on any green lights.

I've seen 3 of her 5 tattoos. For the hidden ones, she told me to "use your imagination."

As far as physical touching (kino), she initiated it. She's playfully poked me in the belly. Whether or not she is normally like this, I don't know.

This last Wednesday, I finally met her son for the first time; her aunt was looking after him while his mother was at work. I chatted with him in front of her while she tended to her aunt, who was in for injury rehab. Does this act of getting to know her son score points or eliminate me as a potential sex buddy?

Also last Wednesday, I asked her out for some food. She said she had to make dinner for her son. Logically, it was 5:45 PM, and to reiterate what she plainly told me a few weeks prior (when she was telling me about her previous sexual partner), she puts her son before everyone, including sexual partners.

However, she replied by saying, "Maybe next time." Not a full-blown rejection, and understandable given the circumstances. Is this a signal to keep pushing the envelope?

Lastly, this same past Wednesday, she came to work one day in a very revealing spaghetti strap that showed off a week's worth of tanning. Her cleavage was very noticeable (she sported a tattoo above her right breast), and the attire was obviously inappropriate for the facility, so she put on a sweater and zipped it up, but not before I was able to see her like this. She's also lifted up her shirt to reveal a navel piercing and a tattoo on her stomach.

The day is coming up, and basically, what I am asking for is a preferential plan of action that you feel may increase my likelihood of reeling her in. This includes conversation topics that will sort of hint at my interest in her, as well as actions you feel I should take.

This is my first time attempting to become involved with an older woman, so please understand that it is a bit nerve-racking, similar to having a first girlfriend. I don't know how the game goes with these women. Also, despite the fact that the work environment may be a riskier place to engage in such activity, she seems to be going for it. I don't want to wear her out, so I want to do something pretty soon.


Summary

1.) At the sports facility where I've been volunteering since last month, I've been talking with a 31-year old single mom.
2.) She's opened up to me about her wild college years and current sex life.
3.) Until 4 months ago, she had been getting it on with a friend with benefits for the past 4 years. He got attached and showed up to her place one day, which she told him never to do. She ended the fling.
4.) She told me that she tends to attract guys my age (22, 23, 24). I'm 21.
5.) She keeps her sexual life a secret from her son.
6.) She's poked me in the belly a few times. I don't know that this qualifies as "kino," but she seems playful.
6.) After asking her, she told me that she would still be interested in having a sex buddy if she found someone.
7.) Since we've met, she's begun tanning. I don't know if it was for me or just coincidental, but I'm trying to be optimistic as far as the signs go. She had never been as tan as she is now, and I don't know that you'd lose a tan quickly. So, I've concluded that before I began volunteering, she never tanned as consistently as she is right now.
8.) This past Wednesday, she dressed in a very revealing spaghetti strap that revealed more of her body than I've ever seen. Appropriate for seeing patients? No. Was it for me? I hope so and my fingers are crossed.
9.) I asked her if she wanted to grab a bite to eat this past Wednesday. However, because she had to make dinner for her son (it was 5:45 PM), she understandably couldn't join me. But she said, "Maybe next time."

I'm sorry for the long post, but this is a thrilling first time for me. I've thought about her every day of the week, and my heart races when I do.

So, I would be thankful for any advice any of you have, if you ever get to the end of this post.

-SomeGuyInAChair

[sudojudo]

Someguy,

You have over-thought this to nth degree. (but very nicely written)

You are getting the green light, but people can send out mixed signals, so ask her again if you can meet outside of the job, if she says no, drop it. You do seem obsessed, which is not attractive.

So here, you want to know what to say to ask her out again? "I admire your (your beautiful skin, OR the way you handle yourself at work, OR ??? pick just one or two) I would like to get to know you better, can we meet sometime outside of the job?...I know you are busy with your son and life, so we can make any arrangement that you would like"

Put it in your own words, and for-the-love-of-god, don't try so hard!

Good luck, Sudo

[lunamor]

Maybe she's just into teasing and provoking.
(As for the tanning, I don't know that it has anything to do with you at all. I mean, hey it's summer - maybe she realized that she's too white for the season).

[houstoncougar]

what else would you like her to do, sit in your lap and put her breasts in your face? I believe she wants it and wants it bad now if you are looking for anything more than the chance to lay a MILF as you call her then I think you're barking up the wrong tree but, then again she is playing around with you and she might get you hooked so watch out cuz you're the one being reeled in babe.

[someguyinachair]

Thank you very much for the feedback, tantricbliss4u. Now, I have to say that if you had made your post 2 weeks ago and I had read it, I would have been very discouraged, although I would take all of your advice in stride. But as it stands, things made a turn for the better 2 Wednesdays ago, when I asked her if she'd like to grab a drink sometime, to which she replied, "Sure!"

We're basically in agreement that what we want from each other is purely physical - a fling. She's not new to it and I don't see any reason why she'd change her mindset at this point. It's also probably because of this that I lucked out and she was willing to be a little more patient with me and my dense head. A kind "No" to my offer to an early dinner but an unhesitant "Yes" to my offers for a drink seems to me a driving indicator of where she wants to take this. A woman who qualifies to be my mom doesn't just have a drink with any guy 16 years her junior!


TWO CORRECTIONS: First, she is 36, NOT 31. Big misunderstanding on my part. That means she qualifies as a cougar, as cougars are >35, no?

Second, she has 4 total tattoos, not 5. Misunderstanding here as well. She wants a fifth and final one but doesn't have it yet. Just being honest.

This past Wednesday...

The physical touching escalated to an all-time high this time. And that is both good and bad.

It's good because after all this time (8 weeks now I believe), she's still showing interest given the lethargic pace that I'm friggin' moving. However, I see it as possibly bad because it could be an indication that she has to step up HER aggression because obviously I was too thick to pick up on her approaches several weeks ago. Very good, very good.

Let me recount the day. Usually, when I have no tasks to do at the facility, I'm allowed to exercise in the indoor gym. It's going to be a little awkward describing the exercise I was doing, but I'll try.

I sat toward the middle of a long bench in a straddled position - one foot on either side of the bench. Maintaining an upright seated posture, I grabbed two pulley handles attached to a cable-plate machine and began doing seated rows. At the time, she was tending to a client, but she obviously must have seen me from across the room because she came over.

Under the pretense of correcting my "bad" form, she placed a hand on my chest and monitored the next few reps I performed.

After I finished those reps, she sat down at the end of the bench so that she was now facing me, and slid forward and pressed her chest against mine, which can only be accomplished by leaning far forward as my legs were in the way. Now, if this didn't tell me that she was interested, I'd be a lost cause. Luckily, it gave me the confidence to do a little more without fear of rejection. By the way, I guess that's why I was so timid with her. It was the fear of rejection. Yes, that was it.

She then left, probably knowing she successfully mind****'ed the living daylights out of me and that I wanted more.

The same childish kinesthetics occurred throughout the day. You know, the belly poking, the armpit tickling. Very ridiculous, I know. Also, I finally discovered the location of her fourth tattoo. Actually, I'd seen it before, but because it was for a split second, I thought it was near her belly button. Actually, it was a long tattoo that extended down into her you know what.

When our shifts ended, we walked out to the parking lot and I walked her to her car.

I told her, "You still owe me a drink. Can you give me a day when you're free next week?"
She replied, "Probably next Saturday. I'll show you a bar in town."

In short, it is on.

This weekend was blocked out because she was out of town, just to let you know.

Now comes learning bar etiquette. I'm a recent legal drinker, if you know what I mean, and I don't know anything about top-shelf drinks and the like. Time to migrate to another forum...

Anyway, it would be appropriate to pay for the first night of drinks, right? That way, I can plant the seed for her to owe me for the next round.

[someguyinachair]

Hey, who rated my thread 5 stars???

[someguyinachair]

Originally Posted by houstoncougar

what else would you like her to do, sit in your lap and put her breasts in your face? I believe she wants it and wants it bad now if you are looking for anything more than the chance to lay a MILF as you call her then I think you're barking up the wrong tree but, then again she is playing around with you and she might get you hooked so watch out cuz you're the one being reeled in babe.

HAHAHA, good one, houstoncougar. But you're right on the money here; she's messed with my head and I want more. I feel she knows it and she's using it against me.

Also, it turns out we have to reschedule our Saturday date. Due to birthday plans, we agreed on next Friday. Over a week of waiting. ****, and she seems to not have lost her composure.

Originally Posted by tantricblissforu

Nice dude. Well, there's always the case that she is teasing you so she can blow your mind later. Keep it up! But be careful not to invest your emotions so far that you will get hurt later..
Hrm, as far as bar etiquette..I'd say just find out what she likes and don't order something girly. You don't need to know anything but that. Yes, you should pay for the first night of drinks...always pay unless you have agreed to let her take you out.

p.s. personal experience tells me you should stay a drink behind her, and mix in a few waters. It's okay for her to get wasted, but you don't want to crash and burn

You know, she supposedly hasn't drunk in a while, and I've been drinking red wine regularly every evening. Not that red wine is that high in alcohol content, but at least I'm a step ahead. That and my being heavier than her has to count for something, right?

Thank you very much about the cautious tip regarding not investing my emotions too far. She probably feels she has the control here, so I plan on not biting as much next time. What is with this sadistic mind****ing?! Why, women, why...

[lunamor]

Because it obviously works.

[houstoncougar]

you sound like the most bitter and jaded player I have never met. You have no earthly idea what a real woman wants if what you wrote in your long ass comment is really what you believe about women in general. Believe me at my age I would enjoy a guy who was just f'in REAL and didn't over think everything like you do. Me, I am just me my tastes, moods and expectations change with each person because they are all unique but guys like you described turn my stomach.

oh and p.s. I was pretty much right wasn't I? Of course she is only 35 so I would say she's still trying to figure out who she is and how to be a mom and a single woman at the same time. I am not the same person I was at 35... thank someone for that!!!

[lunamor]

Well!
When I first read Tantric's extremely detailed analysis and strategy tips, I initially shared Houstoncougar's distaste (although to a much lesser degree - I mean, I just wrinkled my nose a bit ) - much of it DID seem incredibly calculating. Then I re-considered, because he had to know that he was really putting himself on the line in our eyes by talking so candidly and concretely trying to help the guy who wrote that initial post. Tantric's right about inner confidence (not the same thing as swagger) being attractive, and he's made a good defense of himself.
I'm the first to be a real hardass, but I have to say in this case I can't be.