Get that grind on

Trent’s eyes snapped up as Deedee’s command filled the room. He took in the form of his father. The heaving breasts, tiny workout outfit, hard cock tenting out the miniscule shorts, and he knew that last night had not been a fluke. Anger, fear, sadness, and a hint of desire swirled in his mind. While he had just spent time rationalizing and trying to work through his thoughts and feelings, being confronted with them in such a graphic and sudden manner was a completely different thing.

Deedee on the other hand was amazed to see that Tiffany had been awake. With the almost catatonic state she had put him to bed in, she had believed he would have slept till much later in the day. Watching to see if Tiffany would move and follow instructions, Deedee looked at the beautiful blonde. Even without makeup on there weren’t really any hints of masculinity on Trent’s face and less on his body. The long hair, large fake breasts, and long nails helped keep the boy feminine, but there was something else to it as well. A sort of vulnerability, a sense of submissiveness almost, that Deedee had been taught by Chloe to look at as a form of weakness. She could feel anger at the memories of looking like that. A sneer crossed her lips as she wondered if she had ever been truly that pathetic.

Trent looked up and watched Deedee’s face take on that angry look. It was simple to assume that she was upset that he wasn’t moving. Fearing that if he didn’t act on her orders that she might punish him as she had the night before, Trent swung the covers off of his body and sat up in the bed. He could see that he had on the same outfit as the night before. The soft rose-colored nighty barely reached past the bottom of his cage, with his large nipples poking out against it in an obscene demonstration of horniness. If his breasts had been real of course.

Seeing Trent begin to follow her order, Deedee tossed the clothes on the bed. “Put those on, then come see me in the gym. You might want to put your hair up in a ponytail as well.” Turning around, Deedee left the room. She decided to see if he would follow orders while she wasn’t directly watching. Deedee grinned to herself as she stepped into the gym and switched the music over to the speakers from her earbuds. She almost wanted to see if Tiffany would rebel and **** her to punish him. The thought of making the hot disheveled blonde go through the same thing she had the night before filled Deedee with a sense of desire. She could hear the voice in the background that was telling her how terrible it was, but it was slowly becoming easier to push that voice farther and farther away.

Trent’s eyes locked onto the tiny pile of clothes on the bed. He was fairly certain that a single pair of workout shorts that Deedee had admitted to throwing out would have contained more cloth in them than every piece of feminine attire in that pile. His hand slipped out and he ran his fingers over the tiny thong panties, the soft red material less lacy than he was used to. Shaking his head at the thought of being used to panties in general, he began to try and get changed.

Stripping off the rose colored nighty and matching panties, he sighed before pulling on the thong. It felt strange to pull the thong up and not feel it press against the plug. He was thankful, although there was a feeling of something missing. The sports bra was another matter. At first, he would have sworn that it would never fit. Getting it over his shoulders and head had been difficult enough. Getting it over the large breasts he was still getting used to took him at least twice as long. Finally getting it settled, he looked down to realize that it didn’t quite so much support his breasts as push them up and together making even more of a spectacle of them.

Sliding on the shorts, he was surprised when they began to feel snug around his knees. He was completely blown away by the stretch and tightness of the high waisted shorts as they settled over his hips and plump ass. He could feel more than a small section of his cheeks peeking out of the back as he bent over to pull on a pair of tiny ankle socks and the red wedged trainers he had worn the first day. Spotting the scrunchie, Trent’s fingers wrap around it and he stares at the cloth covered hair tie. Somehow the act of putting his hair up feels more feminine than putting the bra on. Looking at himself in the mirror, his hands reach up behind his head and gather the long blonde tresses drawing them up off of his neck. Pulling the hair through the cloth covered elastic exposes his neck and the small earrings sparkling in his ear lobes.

Realizing that he has taken up as much time as possible if he wanted to keep Deedee happy, Trent began his walk from the bedroom to the gym that existed in one of the spare bedrooms. He could hear the beat of the music as he neared the closed door. Opening the door he watched as Deedee continued her workout. Her black hair hung down as she was bent over at the waist stretching. Her plump ass was just as exposed by the tight shorts as his was. The sight sent a flush through his body. He knew it was wrong to look at his feminized father and think of how sexy she looked, but it was getting more and more difficult for him to not associate Deedee with sexual feelings.

In Trent’s mind, the next hour of his life passed more like a montage than real memories of the workouts. Deedee became a ruthless drill instructor. Their time was split between cardio, core strengthening, and of course the glute defining exercises that he had seen celebrities and girls in the gym focus on. The odd part was that once he started working out, unless it was something where the heels in his shoes got in the way or if his breasts made the workout more difficult, he actually enjoyed the time. It was clear that Deedee had a dedicated routine that she had developed, and he could see just how much it kept her in shape as she routinely outperformed him.

For Deedee the next hour was a cooling balm to her anger. She had been unable to lose herself in the workout before, but something about having to teach Trent how to do everything helped her focus. Perhaps it was the way he meekly followed her orders, or perhaps it was the sparks of life that showed when he put the effort in during some of the harder moments, but the anger and derision that had been building up inside Deedee in her private moments lessened and seeped out of her with each bead of sweat they produced. There was little conversation between them, almost none of it coming from Trent at all.

By the time they finished their cool downs, him on the stair climber and Deedee on the treadmill, both of them were flushed with sweat. As the timer went off, they both stepped off their respective machines and Deedee smiled at Trent softly. Pride shone through as she spoke up. “You did good honey. I’m excited to see if you do as well tomorrow morning when we do it again.”

Trent’s eyes opened widely as he gazed at her in shock. “Tomorrow? Like, tell me you don’t expect us to do this every day?” Slipping back into the valley girl accent seemed like the thing to do if he wanted to avoid upsetting Deedee.

Nodding, Deedee smiled and led him back into the bedroom. “Why don’t you take a shower hun? I’ll make us up some protein shakes for breakfast then we can figure out the rest of our day.” As she watched, Trent began to strip down and head towards the shower. Seeing that he was doing as instructed, Deedee moved into the kitchen. Quickly throwing together some frozen fruit shakes, she dropped all the usual supplements into them both without thinking. It was just natural for her to pour the vitamins and other powders she took every day into the shake she made for him as well.

Walking back into the bedroom, she saw Trent stepping from the shower. He hadn’t noticed her yet and was toweling off his body as she had taught him. Patting himself dry, he reached over and grabbed a bottle of lotion she left out for just this purpose. Deedee could feel herself stirring in her tiny tight shorts as she watched her feminized son rub lotion all over his body. He started at the ankles and slowly worked his way up the legs, it was comical to watch him forget that forms on his chest weren’t real as he ended up having to wipe the lotion off of them with a towel after attempting to lotion them up. Seeing that he was mostly done, she stepped into the bathroom and set his shake on the counter. “Here, let me get your back.”

Reaching out and taking a pump of the lotion in her hand, she used her other hand to slowly pull the towel off of his body. With Trent now completely naked except for the shower cap that she had **** him to put his long blonde locks in, she began to slowly and carefully massage the lotion into the skin on his back. Deedee knew she could simply have wiped it on and been done in seconds, but instead she focused on massaging out the points of tension in his body. Her hands deftly pressed into knots and worked them out slowly.

As Deedee worked her hands across his back, Trent **** himself to stifle a groan of pleasure. For the first time it wasn’t purely sexual. The release of tension that had been building over the last few days felt sublime. It even gave him a chance to close his eyes and forget about everything. He just focused on the feminine scents and the feel of the strong long nailed hands that massaged his back. He felt Deedee work her hands across him before her lips brushed against his neck then his ear. “See, it isn’t all bad.” Deedee’s voice was husky and soft in his ear as she stepped away and began to disrobe.

Trent’s eyes opened as he watched Deedee strip. He could feel his cage once again restricting him as the gorgeous milf that had once been his father peeled off the workout attire that barely contained her. Even the last bit where her panties came off and the half hard cock between her legs slipped out brought a sense of perverse lust to him. He swallowed loudly before picking up the shake and heading back to lay on the bed.

Deedee giggled as she jumped into the shower. She let the hot water wash across her as she closed her eyes and began the process of washing herself. While Trent hadn’t had to wash his hair due to it only having been done days before, the same was not true for Deedee and she began her typical everything shower that she did every Sunday morning. Realizing this would leave Trent with nothing to do, she shouted over the sound of the shower. “Honey, why don’t you watch some TV? This takes me a while.”

Trent shrugged and reached into the nightstand to search for the remote. Realizing it was likely on Deedee’s side, he slid over and opened the drawer. As the drawer came open, a loud ringing sound came through. The sound of Deedee’s phone going off was different than Trent expected. Instead of a soft ringtone, this was a harsh shrill noise that was impossible for him to miss. He was amazed when he heard the shower shut off. “Bring me my phone, quickly please!”

Snatching up the phone, Trent rolled off the bed and walked into the bathroom. Glancing down at the caller ID on the screen, he saw who was calling and winced. Seeing Deedee still standing inside the shower, just waiting for him, he handed her the phone quickly. Deedee reached out and swiped quickly, hitting the button to bring up the speakerphone so she didn’t press the expensive electronics to her wet hair. Her voice took on a tone that surprised Trent in its meekness as she spoke. “Yes Miss Jameson?”