My cock hurts

My cock hurts
AMA

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boxers or briefs

Should I attempt to ask my old English teacher from 8th grade for feet pics? It's been 14 years since then and she hasn't aged a fucking day, and we met at a catered event at my job last year, and we've been chatting back on forth on fb since then. She's in her 50s, married with kids. I'm 28, and I fapped to her so much back in the day, still do now occasionally, more so since we've reconnected.

Boxers

Is she into you?

Well she is married, so no. But I was always one of her best students back in the day. And I stared at her feet so much during class, it's a miracle I even passed. Especially when she had on heels with pantyhose or some snazzy knee highs

Personally I would talk to her and drop hints I'm into her and if she responds in turn then ask for feet pics. I'm not you but this is what I would do

Oh I want to tell her so badly how I felt about her back in the day but I'm fucking stuck on what kind of hints to drop. Closest thing I've got is this one time she kept stopping during lecture to pull her socks up to her knees. But I already know she'll be like "lol why do you remember that specifically?"

why pp hurt

Start with complimenting her current looks then

I think I got a uti

Ouch dude

I have. She was flattered, but probably didn't really get what I was getting at. If I wanted to play the long game, I could wait til x-mas day and send her this pic of my friend wearing some socks I got her last year at secret santa (which is true). Then maybe ask her if she has any cool socks of her own to show off

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Doctor gave me some meds so some of the pain subsided but it still hurts like a bitch

That might come off a little strong. Why dont you invite her to a place where shoes arent worn often

Possible. I've also considered inviting her out to get coffee sometime. We're adults now, it shouldn't be an issue, right?

No as long as your friends and hey maybe she'll open up to you more which could lead to you sleeping with her

Umm, did you skip the part where I said she's married, dude? I'm not tryna fuck her (though that would amazing), just trying to get feet pics from her lol. Bare, nylons, socks, whatever

Gift her a foot massage thing and tell her you wanna see if it fits her feet which would lead her to sending a feet pic

Yeah I don't see myself doing anything like that. I'd like to be up front with her about how I felt back then, if possible. But trying to anticipate what kind of reaction she'd have is the worst part of it

Btw, anyone else, feel free to jump in on this one

my cock hurt last night. don't know what the deal was. hurt before and after fappin'.

You know what? Do it,be honest with yourself and her. Also if it doesnt work out, at least you tried and that's more than what a lot of other people would do

My cock hurt because I drank a lot of water and before sleeping and didnt pee for 12 hours

I'm inclined to agree. She really is a wonderful person, maybe if I tell her how much this has been on my mind all these years, maybe she'll be understanding. BTW, this is her. She's in her 50s, I should add ;)

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She is quite pretty ngl

I agree. She hasn't changed at all in the last 14 years

Personally I'd wanna bj from her

I feel that. Tbh I'd rather tie her down and tickle torture her tight little body, she has a great laugh. Maybe buzz her with a wand while I do it, but let's stick to attainable goals

Confess bro

if only it was that easy bro