wife's friend
 

She's been widowed for almost 2 years. I help her with lot of stuff around her house and her yard. She has the littlest tits that I'd love to see and lick and suck.
We communicate via fb messenger for the last several months I been using words and fraises with double meanings. I often kid her about hoping to not catch her naked!:) or in her robe. I've had chance to suggest that she cud pay me, she frets about all I do for her and she wants to pay me...by dressing more liberally, like tank top, or no bra. then I'll apologize. These jus says 'that's ok, I think you're a hoot'.
Sometimes she WILL wear a top with a scoop neckline, but always with a bra. He tits are so small that even downblouses will yield jus a glimpse of her bra encased tits. Even seen some glimpses in the arm holes of her bra.
But today she had on a t shirt. I cud not dectect a bra, either from the front or see the bra lines from the back!!! Her tits are so small, I cudn't tell if they were braless or not...so small there wud be hardly any jiggle, even.
But if she wore no bra today, that is a real breakthru.
Oh, befor I left I told her I like her shirt...it had some writing on it...as I stared at her tits.
We been friends for a long time and I was friends with her hubby.
I sometimes think I might jus ask her if she would be offended or angry if I made a pass at her.

Not sure if I should jus stay the course or try something more.

You are on shaky ground, be careful. My wife and I are early 70's, I was blessed with nice skin, no wrinkles, so I look a lot younger than my age. My wife has several friends who frequently visit, and two in particular are pretty flirty, my wife laughs it off, but these ladies are widows and lonely. They rub my shoulders, one pats my butt, but I am not interested in either one of them.

Now the 3 of them are going to the beach in August, have a AirBNB, my wife said she'll feel safer if I go along. Years ago this would have been a hot dream, not anymore.

Very hot to think about, but dangerous game to play. As hot as it would be to fuck her, and it would be, what happens if your wife finds out?

Any way to understand how your wife feels about her friend and how lonely she is? If you wife were to take sympathy for her friend and somehow encourage or at least not care then you could step up the comments.

Normally I’m a guy very into taboo and sharing. However, this is a risky game. A lot to lose.

I've messed her often usuing words with double meaning. Like I'll say 'I'm cumming' when I'm heading over. Or I'll ask if she is still n her jammies. Or I'll compliment her on her top when she wears a scoop neckline top,
She jus blow me off as me being funning. She says she thinks I'm a 'hoot'.
but she had never returned my lewd comments. and I openly stare at the bra n clothing covered little tits

Think there's ways you could have fun, a lot of fun, without crossing that very risky line. What's the weather like where you are? Perhaps you could engineer a spot of sunbathing with wife and wife's friend. Maybe you could suggest she's lonely to your wife and three of you could go away. Work on your wife beforehand and see if you can get her to do a spot of topless sunbathing. Or suggest it to your friend. Guaranteed if your wife looses her top, you'll see the friends tits too. Or even better suggest a trip to a nudist beach. Maybe you can start to talk about you having sex with your wife to the friend, jokingly suggest she might want to watch, see what tge response is, tell your wife what the friends response is.
Basically I think you have a massive opportunity to screw your marriage up here, but equally a massive opportunity to have some fun. I'd be inclined to bring your wife along for the ride and not keep any secrets from her.

Wife can NOT b involved at all. But tha ks

Well, turned a corner today, I think. I been kidding her about her tops and bras and today she had gone shopping and was home but had to change clothes. I suggested she leave the bra off. More chit chat. then I said ok i'll be over but leave the bra off. she said,'ok, mom!!'. I thot...is she really gonna?
so I want down and thot...I think she doesnot have a bra on!!!
we chit chatted til I finally asked, 'so, you doh't have a bra on?" and she giggled and acted embarrassed but said she was free as cud be. I said I like it, She said normally if home alone she never wore a bra
We chatted some more and as I was leaving I tol her I was glad to SEE her and tol her I hoped she'd never wear one if I was coming by.
When I got home I tol her I liked seeing her and was glad. I tol her that next time (tomorrow) I hoped she'd wear a tank top with no bra. she wore one before, but with a bra.
Can't wait to see

Well, she was braless today, but had a high neck long sleeve top. she had lots of insect bites from yeaterday and that kept her from itching them.
I tol her iwas glas she was braless but had hoped she had on a tank top. hopfully to morrow.
I did reach out as we were taking about her being braless n flicked on tit for jus a millisec fore she slapped my hand away as she giggled.
we'll she hw it goes tomorrow

yesterday she was between meeting and was gonna be public so had bra on. Hopefully today she will bebraless. fore I stop by i"ll tell her 'keep that bra off! you can go FREE for me"

​today I tol her to not wear a bra. that that was an order. she never commented on THAT, tho. But when I got there he had a t shirt on and NO BRA. Nice little tits. I complimented her on them she always giggles and calls me a dirty ol man, slapping my arm and laughing. Right after than I asked if she'd be mad if I made a pass at her as I put my arm around her back, pulled her to me and got one tit n the palm of my hand over her shirt before she pulled awy, laughing and calling me a dirty ol man. There was pause, tho, after I asked if I make a pass. I tol her as I left that I love that look of her tits and hope tomorrow she'd wear a tank top. Tol her I wanted to see that.
we'll see tomorroww. making progress.

oh she said earlier tht it was pretty chilly outside this morning I said YES, it prolly made your nipples stand up!!!
AS she and I stood and she chztted with a neighbor I cud see that then her nipples were standing up.