I was volunteering through my sports team to help young children read. There was another player on my team helping out (to my right a few feet over) and then there was a milf helping out as well (to my left a few feet over.)

This milf hb 7 with a rocking ass, arrived in the volunteer area about 5 minutes after my teammate and I had settled in to our volunteering spots (made eye contact a few times.) My buddy spotted that the milf had a tramp stamp while she was getting her volunteer gear ready at the desk where you collect the material you need and my teammate gave me the heads up on her tattoo and nice ass. So she finally sits down and organizes her stuff on her own desk and immediately has her feet and chest pointed right at me as almost as if its awkward for her to sit that way. I took it as a major IOI, I would make quick eye contact with her while playing on my phone waiting for the children to come and start their reading program.

The first set of children come through and do their reading with us volunteers so all, my teammate, milf and I have to reorganize our stuff which includes getting more materials from the desk behind us. At this point in time the milf got up before I did, but I immediately got up and went to the same book shelf as her and got rather close to her, I had to reach right in front of her (she didn't move at all) IOI, while maintaining this really fierce eye contact. I got the materials and returned to my seat to get ready for next set of children, once I was organized I look over at her and she has her chest and feet pointing right at me while playing with her hair and we have some intense eye contact. At this point really no words have been exchanged.

So once again the second set of children come through and are done with their books, so we (teammate, milf and I) have to get organized again. She gets up really fast this time and pulls her pants up to show her ass even better with her skin tight jeans while getting her stuff organized at the table behind us, I then get my stuff off the table behind us and have this really sexual eye contact with her trying not to break it to show I am confident. She breaks the silence by asking

MILF: What are you up to after this? (She is smiling, eye contact, touching hair)

Me: Probably going home to sleep or something like that. What about you? (maintaining sexual eye contact throughout this)

MILF: Oh nice... I am going to do some errands and stuff like that, are you at this program quite often? (sexual tension is building with pauses in between talking and immense amount of sexual eye contact)

Me: I am scheduled to do this every week but I can't always commit, with some sort of lame joke I played off of that I don't remember. (She laughed, touched her hair) Do you have any children here or?

MILF: Nope, I just volunteer, my house feels empty as my last kid just moved out.

Me: Oh nice (then the children start coming back into the volunteer area)

During this whole little conversation of not much but small talk there were so many IOI's, the sexual eye contact was so crazy, I have never felt that before.

So the 3rd set of children come and go and this signals the end of our volunteering. My teammate directly heads out the door (but I am his ride back home) while I sit back and pretend I am doing something and wait for MILF. We say good bye along with this crazy sexual eye contact and then I can't resist my self, so I head out the door and start sipping on water from the fountain outside the door while she continues to pack up inside. As soon as she walks by I ask her, her name and then she asks mine. I tell her that I think she is cute. And then we go to the sign out sheet together and she has her phone out so I am like this is the perfect opportunity.

Me: "Would it be weird if I asked for your number?"

MILF: "Maybe a little but thanks for the compliment."

We then headed on our separate ways outside the volunteer place.

So I know the last bit I could have persisted and got her number but I didn't necessarily want to as I know I will see her again next week at the volunteer place as we have the same time slots.

So next week do I go about as if this didn't happen or just continue on what I was doing without asking for her number again until I build up more tension/rapport/comfort.

This is was pretty crazy for me to do this as I am guessing she is at least 20 years older than I am and I do not have much practice of approaching on girls my own age let alone a MILF.

After this, even though I was rejected, I had so much confidence in myself that I was willing to go approach any girl I wanted.

Build more rapport, then be far more bold with your moves. A mature woman has seen and heard almost all kind of lines and tricks. Just be bold and straightfoward.

you need to be more like a boss and close
take control of the situation tell her this is the way its going to be
remember cat string theory if ur easy she wont be interested if ur hard to get she will come chasing
so dont ask for her number tell her to give u her number
next time u see her dont run to her like a puppy get her to come over and be more cocky but still cool

I will definitively take those to mind, but I also found out she has a boyfriend (not actually married).

So continue like normal?

but she didnt mention it so like alot of girls do even when they dont actually have a boyfriend. i take that as an ioi
go for it she might just want the hook up

Sounds interesting. I am probably a lot older than you, 40, but in my younger days had a massive thing for older women. Older women love attention from younger men. But there can be a little bit of a stigma if the age gap is too great. She may be concerned about that.

If I were you, I would give the impression that you can be discreet. ie she might not want everyone at this place you work together to know you are together - well not until she really knows you anyway.

I would be really up front with her. I know a lot of people go with the make out you are not interested stuff. That's bollox in my mind. I would tell her quietly and firmly when out of earshot of anyone else that you really like her and unless she gives you her number you will literally stop breathing.

Give it a go. What have you got to lose.