I don't dislike her at all. And I trust him 100% so I know he would never share them or repost them anywhere.

Sure, why not? He's already seen everything, right?

Well everything on her. Obviously the hardcore shots would show everything on me :eek: as well.

Update
 

Well the verdict is in....I did it; I showed my friend the hardcore photos of my ex. First he got to see her using a vibrator. With him want to see more, I moved on to showing him photos of her giving me a blowjob. Needless to say it was a bit nerve-wracking knowing that my friend just got to see my dick rock hard and being swallowed by my ex. He asked for more, so I showed him me fucking her doggie style. You guessed it, he wanted to see more so he now knows what it looked like when my cock penetrated her pussy. And without even waiting for him to ask I ended the photo sharing with a couple of shots of her pussy covered in my cum.

Does this make me a bad person? lol.

Just made some animated gifs from some of the photos I showed him (blowjob and fucking); think he would like to see her in 'action'? Should I mention it and share?

Just before we met, my wife went on holiday with her friends, 4 girls and 2 guys.
After ten years we regulkarly meet these friends, including the husbands and boyfriends of the girls.

During the holiday there are two tremendous upskirt pictures of my wife and on another girl. The picture has been taken by one of the guys with a "smart angle". The four girls are sitting on a sofa and my wife and another girl are with a mini skirt, parallel legs not crossed and a bit open with white panties perfectly visible under the flash, it was late nght, maybe a bit drunk.

All the participants have electronic and printed copies of the pictures, also available to husbands and boyfriends. The pictures have een shown and circulated among all the rest of the friends of my wife.

For clarity sake the "dressing code and rules" among our group of friends are quite rigid and modest. An upskirt is an embarassing event.

Have you tried the google reverse image search on the pics?

Dangerous game...
 

I've been playing a dangerous game for about a year now. My cum candy used to pose scantily dressed for camera clubs when younger but steered clear of exposing herself beyond tasteful nude. Lately we have been really getting off on taking soft core photos which I started posting on web sites without her knowing. With me egging her on the shots have now reached pretty hot soft core or pretty cool hard core depending on your view. There are shots of her sucking like a porn star and ramming a bottle into her pussy as well as getting fucked by me. I am quite careful where I show them, usually censored., but lately I've started showing her face. The thrill is so intense. One even got reposted here.

Update
 

Starting to get request from other people to be allowed to re-post her and even from a webmaster to put a set of her on their porn site....

re-posting
 

I know they usually just get reposted, but just getting asked for a set for a website is a heck of a turn on....and just a hint dangerous. I know she gets a kick from the danger element of taking her panties off in a bar and being seen having sex in a car with me....just not sure she realises she could have a career as an amateur porn star.