Trips were fun
 

My wife would send nude selfies to me when I was on trips. Sometimes just “tame” full frontal, others touching herself or using her vibrator. One time I was in a meeting and opened her text and attached was a video of her using the vibrator or her until orgasm, screaming. Luckily the sound was muted. Even so, I had to get to a stall in the bathroom, it didn’t take me 30 seconds.

Old friend
 

I was texting with an old girlfriend a couple years ago and just catching up.. she had just got divorced and I was bouncing around a little with a partner or two. She seemed a little lonely and down.
Trying to lighten the mood we reminisced a little about fun we had shared many moons ago.

During the conversation we were joking a little and we knew we were both laying in bed and I asked what she was wearing and half way through describing her nighty she said wait and sent a picture.

It was a pretty tame pic but showed some nipple through the thin material. So I joked a little about it and that she looked good and pretty sexy outfit for just a night in by herself - but too really kick it up, maybe a little more cleavage and so another set of pictures arrived and showed a little more. Sitting up a little you had some definable cleavage and some side boob.

Before long she had sent a few riskier pics.
She was always so straight laced it was nice she was so willing to give me what I asked for so easily and freely. It had been years since we were intimate in any way.

So she then asked what I was wearing and did I still sleep nude. So I sent her a pic or two…. As my pic was me naked and showing the effects she was starting to have on me during this game - she then ramped up the amount of skin in hers as well.
Before our phones died she pretty much masturbated to orgasm for me on video.
With the added surprise of a complete shave…, as she was always a full bush girl.
I was told I could thank her daughter for that as she told her she needed to get with the times, now that she was single again.

We ended up sexting a number of mornings and the next time I was in town we hooked up…. Had a couple nights in a hotel.

I Hadn’t seen her in maybe 20 years but before that we would sometimes connect and fuck just out of the blue if we were both able to sneak away from our current partners.

In the end the pics and the game was more erotic than the reconnection and we have since drifted apart other than a call or two a year to say hello but unexpected photos were fun.
Actually funner than the reconnect as it carried no baggage.
I should have kept them but we or “I” kept my word and deleted them after a day or two.

I once got an audio text from a FWB. I was in a car with a bunch of buddies, and was able to kill it before it got raunchy.

DR

Damn, these are insanely hot stories! My favorites are the ones where there's a friend of your wife in the picture or video that you weren't expecting to see naked or semi undressed. I'm still jealous of all these instances though!

I used to chat with a guy and send wife pictures. He sent me two unexpected pictures they sent him. She was his wife's best friend. He knew her and was hot for her for like 8 years. They were out drinking without him and sent him a tit flash video and a mooning video where the friend pulled her underwear down too (most moons I've received had a thong on) and she bent over a little too far and by pausing it you could see her pussy. He said he's used it every time he's jerked off since receiving it. Lol

Idk what it is, but no matter how hot or ugly, the wife's best friend naked is always the hottest mystery. I need to send mine out on girls trips more often and hope for the best, I guess? Lol

Friends Wife Golf Trip
 

Went on a golf trip with three other buddies this summer. Golf Saturday, golf Sunday and come home Monday. One of the guys is married and his wife is unofficially considered "one of the guys". We are all in a 5-way text chat - the four of us guys and her. She wanted pics of us and wanted to know we were having fun.

And I know that breaks the rules of a guys weekend trip, but she was joking that we should go to a strip club - so she's pretty entertaining and passes the vibe checks. One of the guys in the group replied, "we're too tired from golf to move, but you can send nudes if you want." She gives the crying laughing emoji to that comment. And my buddy who's married to her with a "C'mon!!"

The chat went dead for two hours and then we all got an ass selfie from her around midnight. Total surprise. Our buddy married to her was very annoyed and mad at the guy who asked. And then he got on the phone to scold his wife. The rest of us went and jerked off to it.

I was in a similar situation on a fishing trip, my wife responded with several very hot nudes with the face obscured. I let these guys, none of whom had met my wife, go crazy, until I told them the truth, "my wife is a brunette, not a blond, and if she had that body at her age, I would not be there fishing with them." My wife was at the time a very fit 55 y/o, the girl in the pics was no older than 25. But she does have a sense of humor.

About five years after we got married, her ex boyfriend slipped a bag full of her old Polaroid's into my pickup truck. They must have made Polaroid rich with so many pictures. Obviously, she was quite the nympho before we met. there were some taken not even I can compete with.

Not a pic story - but we were on a beach holiday with some friends of ours and his wifes sister. Her hubby Charlie was very obviously pointedly walking very close to any topless ladies on the beach to ogle them which pissed his wife off.
My wife is pretty prudish when it comes to showing herself to strangers / friends - so it was a total surprise when Charlie and I rounded the corner of our villa to be confronted by 3 ladies ( Charlies wife, my wife & Charlies wifes sister) all with their tops pulled up flashing their tits to Charlie (& me of course). They said - "saves you going to the beach Charlie!" Quite a sight - they all had nice tits

friend
 

I have sent some 30 year old pics & videos to a good friend of ours to cheer him up after a prostate op. - but he doesn't like to receive them saying he respects my wife too much & deletes them immediately asking me not to send them.

A friend of mine sent me a pic after she dyed her hair herself, but she was in a pj top. No bra. I didn't notice the hair because of her nipples poking at me, and her clingy top showing off her unusually perky natural C cups at 48yo.

I told her that I never expected to see what I could see, and she didn't understand how I was shocked to get a braless clingy pj pic from her.

Then I told her that her hair also looked nice.

I blew it, though, as she has never sent me a photo since of anything but her dog now and then. At least we are still really good friends. I should have only commented on her hair, but I was hoping my comments would get her to send more photos that were similar. Bummer.