Jack Struggles...

Saturday rolled around faster than Jack could mentally prepare. He hadn't slept apart from Diana in years, so having her gone for an evening was already rough. Adding to it that she would be spending all night and most of the next day in Tony's arms... And Jack wouldn't be there to see it. On top of all that, other issues were weighing on Jack's mind. Every day, Reginald was pushing for more and more information about Diana and Tony. Jack had to wonder if Reginald had some twisted sixth sense for depravity.

As for the current state of affairs, Jack and Diana had made love the night before, holding each other tenderly and whispering promises to always be together. Jack had to marvel at the duality of Diana's needs. A loving, gentle, and loyal husband on one hand. On the other, a rough and dominate Bull that had helped her break free and find herself in her youth. Even with Diana's reassurance, Jack still couldn't help but worry that she would slip away from him.

That morning, Diana had showered and kissed him goodbye after breakfast, and Jack had gone to work as usual. The day seemed to drag by, but he got his normal messages from Diana about her day. At lunch, she text that Mary was teasing her and asking for details about her time with Tony. Jack had a similar, but less fun time with Reginald. As always the man pushed for more information. The day drug on from there, until finally he made it home from work. He hadn't checked his phone as he was leaving, but he felt it buzz in his pocket as he drove. He was almost scared to read it, but finally did so after getting inside.

*Following Tony to his place now. I'll message once I get there. Do you want any pictures or videos? I can't promise, but I can try to get some.*

Jack text back *Surprise me.* Truthfully, he wasn't sure he could handle this. Having Tony come to the house and watch them have sex was one thing, but being apart while it happened felt different. Tougher. Being the only one left out cut into his soul in a way.

Jack settled in, warming some leftovers in the microwave and sitting on the couch to try and relax. He was just finishing his meal with the next text came through, this time from Tony.

*Don't worry man, I'll take care of her. We just got out of the shower.*

It was followed by a picture of Diana. Tony must have taken the picture from behind her. Diana wasn't looking at the camera. Instead, she was was facing towards a bed, a towel wrapped around her head. Her back and shapely ass were on display and Jack could still see water beads glistening on her back.

Then a second picture came through, this one much closer. The towel was now discarded on the bed with Diana bent and holding herself up with her hands. Tony's dick rested with the head probing her pussy. Jack could see now what he couldn't in the other picture. Her pussy was already slick with cum. They had been fucking in the shower...

Jack pulled his attention away from the pictures. His dick was hard and he felt both horny and confused. He was still feeling hurt, but lust was wrestling with those feelings in his gut. Maybe some tv would help? He could put on a baking show and.... The USB that Tony had given him was sitting on the tv stand, just under the tv. Diana must have put it there a few days ago when he first brought it home. She had told him to wait for her but...

Jack knew this was a bad idea. She had explained her past and told him that it would hurt him to watch alone. That didn't stop him from plugging the USB into the tv and using the remote to bring up to folders it contained. The first was labeled "Pictures" and the second as "Videos." Nothing crazy so far. Jack selected pictures first and found over a thousand items to select. The thumbnails for each gave a minimized version of the picture, and some had an actual title. The first was "New Girl" that showed a young Diana, wearing a modest blouse and vest, and a long skirt. She was chatting happily to a friend and had a red solo cup in her hand. Based on the people around them and that most of them had a similar cup, Jack reasoned that this was a college party of some kind. Tony had noticed Diana before she noticed him. He scrolled down to the next image labeled "Sleeping Beauty." Diana was naked and sleeping soundly. There were bite marks all over her, and he could see cum leaking out of her pussy. That was becoming a familiar scene to him. Based on the time stamp, this picture had been taken the same night as the first picture.

Jack gulped, feeling nervous as he pressed the down button and let the pictures scroll by quickly. When he finally stopped at random and clicked, the next image took his breath away. Diana was on her knees, looking up at the camera. A dick, likely Tony's, was in her mouth, but she also had one in each hand. He scrolled more... Diana against a wall, one leg raised all the way up to her head, her panties pulled to the side and her skirt riding up as a big black man fucked her. Scrolled again... Diana getting fucked from behind while Tony pulled her hair with one hand and took a picture with the other. Every picture told a story of her past. Diana had told him that she had been really active, and Tony kept calling her a slut. Jack had stopped questioning the slut comments, but as he saw more and more of her with men other than Tony, it really began to dawn on him why Tony said it so often. Why she seemed to blush and get horny when he said it. Diana loved sex. Loved to be used and passed around. Jack didn't think one, or even two men, could ever be enough for her. She would need more.

After going through more than a hundred picture, Jack swapped to the videos. There was less than five hundred of them. That number felt staggering to him. He watched his beloved ride Tony's cock and scream his name. He saw her getting spit roasted by two men, one being the black man from earlier. Heard her scream for more as another man fucked her ass. Jack didn't know when he took his pants off. By the time he had stopped watching the videos, he had came twice and was a panting mess on the couch. on the coffee table, his phone buzzed. Jack opened it up and saw a short video from Tony's point of view. Diana was riding his dick and moaning loudly. It had been almost two hours since the previous pictures... Tony cleaned up his mess and went to bed early.