I used to work with one of my moms best friends, shes a single milf in her upper 40s. Somehow when we worked together we started texting and text off and on even though we dont work with eachother anymore. Shes been sending me pictures of herself, theyre cute but shes not sending nudes or anything like that, just tasteful shots of her. We've made plans to go on a trail hike a few times but something usually comes up (last time I got a bad cold and cancelled, then she had to cancel because she was on a trip). Should I just text her saying Im interested in her sexually (obviously Id word it better than that) or should I wait till we're hanging out irl. My main fear is obviously if it doesnt go right and she tells my mom I hit on her, that would be brutal. Shes got a similar vibe to picrel. Ive almost told her the truth a few times but then I jerk off and realize how not fun it would be if my mom knew I was hitting on her friend. They dont talk very much anymore though if that matters. What would you do?
>>34563491Wouldn't do it with a friend of your momIn general yeah but don't expect them to last for long
>>34563573True, if the tables were flipped and she were flirting with one of my friends Id go nuclear. And yeah theres no long term potential obviously, maybe the lust just got ahold of me, its slim pickins out where I live.
I only messed with milfs younger or a little older not ancient. >>34563578You said it partner. It's like being prison gay. You need to find love, or lust will just consume your thoughts. Where can you find a long term gf
>>34563588The only people my age I match with on apps live like 4 hours away, everyone in my town or workplace are geriatrics or married. Basically my only option is move closer to the city but shieeeit I also hate it there.
>>34563491Dude, don't stress yourself! She is an adult, she ain't telling your mom. You are likely to ruin it if you start texting about sex / hinting anything. Take her out, get a few drinks into her, make a move, go for a kiss and see it through, please, for all of us The alternative is to miss out on this potentially cool story and be regretful till end of days, your pick. Yeah, it's unlikely you'll have a family together, no it doesn't mean you can't make some fun memories or learn something about yourself with her
>>34563491It only works with a MILF if she sees you as an adult. Your mother's friend will always see you as "Mary's baby boy"
>>34563491Tell her you got an Olive Garden gift card but have no one to go with. Ask her out, keep the vibe light, order drinks, and when the moment feels right, make your move. If it doesn’t land, you can blame it on the alcohol and keep things chill.
>>34563578Only losers and gaslighters care about "how would feel in other's shoes!" It's not your mom's business and she should be supportive of her son getting pussy anyway.
>>34563491I like older BBWs, especially the post-menopausal ones. They are older and don't get a lot of attention from men, so they get super horny and interested if you show them any attention. Also, they'll usually be down for some more kinky shit. I've regularly gotten to do anal, light bondage, and most of them will let you cum inside.
>>34563491Go for it now while you can. If you wait too long in life to get with older women you will be cruising the nursing home.
