How Would You Handle This Situation

You have two choices.
Approach in person and ask for a date. Do not mention the site.
Contact online as you would any other woman. Tell her who you are.
I do not see the problem with her knowing you are on the site, if she is on the site.
More likely, she will not be interested because she is too close to your child.
A lot of people put their faces online and do not care. Couples have been selling porn movies of themselves since the internet started .

Live and let Live.

Let her get off on her thing. Why say anything.

Remember those who live in Glass houses shouldn't be throwing stones.

"Low and behold I see my son's teacher on the damn thing... " and "...she's my son's teacher when he was in 2nd grade."

Can you clarify that for me? Are you saying that she WAS your son's 2nd grade teacher but she is no longer his teacher? How long ago was she his teacher?

FWIW, it's highly unlikely that if she's on a swingers' site that she would "out" you for being on a swingers' site.

If you don't want anyone in your small town to know that you're on a swing site, you should show her the same courtesy. It sucks, I know (and not in a good way), but a single lady is going to probably have more community issues with being on a swing site than a single guy.

On the other hand, try to figure out if she's attending a party or meet/greet, and see if you can attend. That gives you a mostly non-creepy way to introduce yourself to her in the swing world while still avoiding most of the issues for her.

I would message her on the site. I would not say anything about knowing her. I would emphasize that you are VERY discreet and would expect the same of her and see if she responds. I would not reach out again. Let her think about it. When I saw her at school, I would smile and maybe wave, but let her approach you in public if she is so inclined. You offered her what she wants. How bad can it be?

"I think I might just approach her as a guy that's just attracted to her and not mention any swinging at all."

Since you don't want to mention anything about yourself being on these types of sites, that sounds like your only option if you are going to pursue it. It sounded like she was a teacher for your son in the past and not current, so if that is the case and you don't have younger children that may have her as they get older, then I would not consider her off limits.

Don't shit* where you eat.**
*have sex
**send your kid for an education

Consider her off limits.

Just answer her ad like you would any other lady you'd like to reply to. She already has something in common with you, as both of y'all are members of the site. She may have the same concerns about the small town thing you mentioned and appreciate a discreet friend....and hopefully FWB!
On another note, we used to go to some fun sex parties in Santee! Carolina Friends used to rent a whole hotel right off I-95, not too far north of I-26/I-95 interchange. The pool was very private and you could swim and sunbathe nekkid....lol. Good luck with teacher lady!

Yes send a nice well thought out message and ask to meet for a casual drink or coffee.. if it was meant to be its a done deal.

Lets just say I was in a high profile #2 in command position in south Florida.. we had well known Judges, Attorneys, teachers, nurses, school teachers, fireman etc etc .. we called it choir practice in the 70's but all met to swing and have some great sex and parties.

If you dont ask one will never know.. and on the other hand have some great hot sex! If you want to be successful swinging be kind, have some class, smile, always dress up on a first meet and the rest is history! Dont be the one who sits and watches from sidelines!

By the way big improvement on photos.. KUDOS always add and update as you go along... suggest to get rid of duplicate one have one dressed up and have someone else take it.. coworker, neighbor, friend.. but no more selfies... keep smiling!

HotTx couple we live in a small town in SC. I don't want her to know I'm on a swing site. Never know how people talk.

I think I might just approach her as a guy that's just attracted to her and not mention any swinging at all.

Just send her a message like you would with any other woman that you would like to meet on SLS. We have met teachers on SLS before, and they were just like everyone else. Just wanting to have fun discretely. But have not met any that we knew.

I would mind my business she's not doing anything illegal

So I log onto another swing site I'm a member of.

Low and behold I see my son's teacher on the damn thing. Face pictures and all. Divorced white female 42 looking for BBC never had it before and always thought about it. I was in a state of shock last night. I've talked with this woman occasionally, I see her all the time at Friday night football games and she's my son's teacher when he was in 2nd grade. Went through a bad divorce and all. Brings cookies and stuff to the school.

Blonde about 5'5 nice tits awesome bubbly ass with puppy dog eyes. She's always at the games with some older women or with her daughter. Never around any men. I mean she's a next door type MILF. I don't believe in putting faces on sites like this and I'm very discreet with my own privacy. But wow I want to screw this chic. You can tell she probably hasn't been fucked good in a long time.

How would you approach her? I don't want to say I saw her on a swing site.