A new outfit, and guests to the house

(Author’s note - Hey babes, tried something new with the images again today. Let me know how you beautiful people like this approach!”

Also babes, thank you so much for the 100 likes! Love that people are enjoying this!)

Deedee’s body slowly came to life the next morning. Her schedule was to get up early enough to do her typical workout as well as get her makeup and hair in place before work each morning. This meant that around 5 am each day her body fairly naturally became aware, apparently she had been so emotionally exhausted the night before that she slept till almost 8. Also new to her was the head of blonde hair that sat directly in front of her and filled her vision. Typically, when she woke up with someone in a bed together it was not as the big spoon. The scent of femininity that drifted back to her brought a smile to her face as she leaned into it. The warmth of Tiffany’s body as it was snuggled up against her was comforting. Leaning forwards, she kissed the back of his head softly, then slowly and carefully disentangled herself from his body. Not wanting to wake him up yet, she began her preparations for the day quietly.

Picking up the heels that lay next to the bed on her side, she padded softly out of the bedroom and into her closet. Closing the door behind her, she caught sight of herself in the mirror. The person staring back at her was different from the carefree and happy woman who had gotten ready for work two days ago. There was a sadness about her that she did not enjoy. Being able to rely on Miss Jameson for all the decisions over the last year had made her life so simple. Now, she was deciding to complicate it, and she wasn’t sure it was the right decision.

If yesterday was any indicator, she was not good at this whole domination thing. Sure, Miss Jameson had shown her exactly how to trap him. The path had been laid out for her, now all she had to do was follow through with it. Yet she was worried. Was that what she truly wanted? Or was she just lashing out at her son in the place of her ex-wife? Deedee knew it wasn’t Tiffany, or Trent’s, fault. That didn’t stop her from feeling some resentment.

Deedee knew that there was no way for her child to know all the problems that her ex-wife Jasmin had put their family through. The ways that her ex-wife would sit there at night, in the very bed she had just gotten out of, and tell her that the only thing she was worth was the paycheck she brought home. It had all been for Trent that Deedee had stayed in the relationship. She had toughed it out, knowing that in only a few years Trent would go away to college. Then, before they could reach that milestone, Jasmin had left. Worst yet, she had divorced him and gone after alimony. Her shark of a lawyer left him with barely the house and a portion of his salary. It was a scant three years later that Miss Jameson had made her move on him.

Putting her mules back along her wall, Deedee reached for some comfort clothes. A black twin thigh slit maxi skirt replaced the sleep shorts. A baby blue halter top that crossed over in front made for a fantastic display of inner cleavage replaced the top to her pajamas. The shoes were really what brought her day back. A pair of new heels she had picked up just a week ago and not been able to wear yet. The pencil thin baby blue sandal was a classic. With only a tiny thin strap over her toes and a matching ankle strap, they were almost nonexistent. Only the color that matched her top and the height of the heel made them stand out. It was the perfect outfit for relaxing around the house as she had intended. Throwing her hair up in a messy bun, she sat down at a vanity and began the soft subtle makeup of the day. When the nude lip color was set, she stood up and felt ready to face the world.

Deedee’s outfit

Stepping over to her mirror, she looked back and was finally happy with who she saw. Derek was gone, only Deedee remained. Derek was the weak one. Deedee could do as Miss Jameson prescribed. It was easy to do what she was instructed, and this was how Miss Jameson had said she could get through this. That was the way to deal with this, follow the path and keep the course. The resolve in her eyes solidified as she thought through her plans for the day. Stepping over to one of her dressers, she opened it up and pushed some boxes to the side to reveal her safe. Quickly punching in the code she reached in and retrieved Trent’s phone. A number of messages and missed calls from Brittany, Trent’s girlfriend lit up the notifications. Swiping through those, she saw a pattern form and a plan came to her. The grin on her face would likely be called evil by many as her fingers began to fly across the keyboard of her son’s device. To her, and the one whose orders she was following, it was just what needed to be done.

Meanwhile, completely unaware of his father’s scheming, Trent lay in his father’s bed. His eyes had stared at the wall as Deedee had roused herself and kissed him on the back of the head gently. Very little sleep had come to him through the night, it was impossible to get comfortable in the tight pink cage and with his new breasts. And then, some time in the night he had woken up to Deedee’s member grinding against his sore ass. They had stayed interwoven like that for the rest of the night, with Trent dozing off out of complete exhaustion at times. Only to wake up again shortly as Deedee’s hand would unknowingly brush over one of his hypersensitive nipples, or for his cage to suddenly feel too tight as a dream or possibly even the feeling of Deedee embracing him brought about an attempted erection.

He felt like he had been able to get three or four hours of sleep in a row, but nowhere close to the 10 or 12 he was used to. Rolling onto his back as soon as the door closed, Trent laid there staring up at the ceiling trying to think of a way out of this mess. He wanted to believe that Deedee would let him go today, that yesterday had all been one very bad practical joke. Sadly, no matter how hard he tried to rationalize it, he knew better.

This was how Deedee found him when she came strolling back into the bedroom, a soft smile brightening up her face. “Oh hey baby, you are up already! Shame, I wanted to wake my sweet princess with a kiss.” Trent sat up slowly and took in his father’s outfit. The slits in her skirt went all the way up, so each step revealed an astonishing amount of leg. His eyes drifted up to where her breasts were on full display, and the errant thought that he could fill it out just as well made him wince in humiliation. “Well, even so, let’s get you up. I need to get your hair and makeup done before Jessica gets here, plus we should probably grab some breakfast. Unless you were craving sausage?” Giggling at her own terrible sexual pun, she stepped over to his side of the bed and tossed the covers off of him.

Reluctantly he moved his exhausted legs to the side and began to stand up. Before he could even get to a full standing position, Deedee’s hand connected with the center of his chest lightly. The shove was more than enough to knock him back onto the bed, his new center of gravity making him feel top heavy. Looking up at her, he raised one sculpted eyebrow in confusion. “Why…” His voice was hoarse with disuse from the long night, but the deep sound that came out reminded him of one of her rules that he needed to follow. Switching to the lighter tone, he tried again. “Like, why did you knock me down?”

“Heels babygirl. You know the rules. I’d hate to have to punish you.” Pointing down at his bare feet on the carpet of the bedroom, she stepped away into the bathroom. “Get those cute little tootsies in your cute little heels and we will get you started. I picked out the hottest little outfit for you today. I think you are gonna love it.” Trent did not hold the same optimism.

Standing up into the heels brought back the rush of memories from the day before and even with his nightie just barely covering his ass, he reached back to smooth it out as he stood up. As he regained his feet, he looked up to catch Deedee moving back through the bedroom towards his old bedroom. The light of the sunbeams from the morning sun glinted off a piece of metal in her hands as she moved through the room swiftly. Only one thing he knew of would shine like that, he simply sighed and trudged along behind her. Although most would call the walk he had anything but a trudge.

As Trent moved into the room that had been repurposed as a closet, he looked around. His eyes lit onto the outfit she had laid out for him to wear. It took all of his effort not to sigh at the black lace covered corset and panty set that he knew would come first. Next to it laid a beautiful black sundress with pastel flowers all over it. He could see that it wouldn’t cover much of his legs, likely even less than the dress yesterday had. And of course, on the floor in front of them was a pair of nude six inch peep toe platform slingback heels.

Tiffany’s outfit for the day

As Deedee helped Trent out of his night clothes and into the new outfit for the day, she kept up a running commentary on what he needed to know should he find himself needing to get dressed without her. His mind let the information go in one ear and out the other, unable to retain anything due to exhaustion from lack of sleep. Once dressed, she sat him down in front of her vanity and began to do his makeup in a similar way to hers for the day. Again, her explanation of process and procedures fell on deaf ears as she attempted to educate him on the proper use of makeup to help feminize his face even more. Following his makeup, a pair of large hoop earrings were clipped onto his unpierced ears and an accompanying necklace was added to his look. The necklace sat directly in the very visible valley of his cleavage and managed to draw even more attention to the displayed skin.

Just as she was finished styling his hair, the doorbell rang softly through the house. “Ahhh! That bitch always has perfect timing, I swear.” Giggling, Deedee stepped away and busied herself throwing small items into a small nude colored purse. “Go answer that Tiffy baby, it’s Jessica.” Shooing him away, she left him with little choice but to step out into the living room and answer the door.

Clicking his heels across the floor, Trent was thankful that he was no longer in the mules that he had worn around the house the night previously. While they had not been uncomfortable, the lack of support gave them a precarious feeling that compounded with how heels in general still felt to him. In truth, the pair of platforms he had on might have been the most comfortable heels he had worn yet.

Without thinking it through, he reached up and pulled the door to the house open to reveal Jessica. His eyes looked over her slowly and took in every detail. Her apple cheeks gave her smile a mischievous look, her pink hued makeup designed to bring attention to her plump lips and bright eyes. Her hair was much like Deedee’s that day, up in a messy bun that she had likely spent quite a bit of time on. Each free strand seemed to dangle at just the right length to highlight her longer elegant neck or her earrings. The large silver and diamond studded hoop earrings swung from her ears as she seemed to be taking in his own fashionable look as well. Her heels must have been an inch taller than his. As he knew from their previous encounters that when she was barefoot, she stood just under his 5’5” height. His gaze slid down her long and recently lotioned bare legs to take in the sparkling white platform heels on her feet.

Jessica's white as snow outfit.

Without waiting for his acknowledgement, she stepped past him into the room. The scents of leather and roses filled his senses as she moved by. The roses must have been her perfume, but the leather scent came from the incredibly tight and small strapless leather mini dress she had on. It was one of those outfits that made you look at a woman and wish she was yours, all while knowing she was too good for you. Her voice broke his concentration as she spoke softly. “A girl could get used to being looked at like that. But best not to make your girlfriend jealous, right Tiffany?” Giggling to herself, she stepped farther into the house.

“I wouldn’t worry about that. Tiffany there is the perfect little wifey, aren’t you baby?” Deedee stepped out into the living room and walked up to give Jessica a hug, their air kiss kept their makeup from smudging. “Wow Jess, that is a hell of an outfit for shopping.” Closing the door slowly, Trent turned back to watch the two feminine creatures interact.

Brushing a blonde strand behind her ears, the silver bangles on both of her wrists jangled against each other announcing every movement. “Well, I do have some other things to do after, plus, it is easy to get in and out of.” Treant could see what she meant as the entire back of the dress had one long zipper from top to bottom. “Speaking of which, that doesn’t look like a going out outfit for you Dee.”

Glancing at his father, Trent was unsure why the outfit she wore now was any different than the one he had one or the one she had worn the day before. “It isn’t babes. I’m gonna let you and Tiffany spend some time together. I have a friend coming by the house and I need to show her some things,” Suddenly, even the prospect of going out in public seemed good to Trent. Sure, he wasn’t happy about it, but being able to be away from Deedee would give him a chance to find a way out of this situation. Plus, if he had to do it with someone, doing it with Jessica was the best he could hope for.

“Oh! Well in that case, let’s go bitch!” Jessica turned to Tiffany and reached out to take her hand before Deedee spoke up again.

“Not yet hun. Tiffany needs to grab her accessories. Make sure you put all of them on alright babes? I left them in the closet.” Starting to recognize the differences in the playful tones that Deedee used, Trent could tell that he was not going to enjoy the items she had laid out. Without acknowledging either woman, he stepped past both and slipped into the hallway headed towards the closet. Both women’s eyes were glued onto his hips as his walk **** the short and flowing skirt to bounce around on his round heart shaped ass.

Entering into his old bedroom, Trent’s eyes were drawn to four different items sitting on one of the vanities in the room. A pair of dark oversized cats eye sunglasses sat next to a tan leather purse with a gold chain to hang from his shoulder. It was the other two items that gave him pause. A bottle of lube and the plug seemed to stare back at him. Picking up the purse and the sunglasses, he stood glaring at the other two offensive objects. Why was she making him do this? Was it because he would be out with Jessica? That didn’t make sense because Deedee had clearly engineered the day. Was it a punishment for something? That was likely the answer, he just couldn’t think of what he had done wrong so far. Other than perhaps not being as active a participant in the farce of a relationship as she would have liked.

Stalling, he opened up the purse and looked through it. Inside was a tube of lipstick, a compact, a pair of condoms, and a single tampon. No money, keys, or even his cell phone. Stamping his foot in frustration, the feminine gesture completely lost on him, he closed the purse back up. Silently shaking his head, the large hoop earrings bouncing off his neck, he gritted his teeth and reached for the plug slowly. Just as his long nails were about to brush it, he stopped. No, he wasn’t going to do this. The resolve hardened in him as his masculinity pushed back against Deedee’s obvious orders.

Slipping the glasses onto his face, he stepped back away from the rest. Turning on his heels elegantly he stalked out of the closet and back into the living room. As he moved into the living room with purpose, both sets of eyes from the women there tracked his every move. “Look, there she is now. Coming out of the closet.” Deedee giggled and moved up to him, her hands coming to rest on his hips as she moved close. “Ok baby girl, I’m going to need you to be a good girl for Jessica today. None of that nonsense from yesterday right? You promised me last night that you would be a good girl for me, didn’t you?”

Nodding, Trent continued the trend of speaking as little as possible. If he could figure out how to avoid saying anything he wouldn’t have to speak in that absurd style of speech. Deedee’s eyes flashed as he didn’t say a word, her head tilting to the side with an inquisitive tilt. “Ok, then babes. Give me a kiss and then you two can go shopping. I know it is your favorite thing.” Standing there, she waited to see how he would proceed.

Closing his long lashed eyes in frustration, Trent leaned forward to peck his father on her lips gently. The type of kiss that you would expect two people in a relationship to share when standing in front of another person. A chaste brushing of lips was his intention. Of course, that was not the plan that Deedee had in mind. Pulling his body tighter against hers, she pushed into the kiss. Her hands slipped down from his hips to fully wrap around the globes of his ass as she leaned in to push her tongue forward.

Knowing that if he rebuked her it would only lead to more issues, Trent opened his lips and allowed her tongue into his mouth. The heat of the kiss began to get to him as her tongue played against his. It was so easy for him to respond to the kiss, so natural to kiss her back that he couldn’t stop himself. His own hands slipped up around her neck to toy with the strands of hair that had slipped from her messy bun. What had been a single kiss had become a full on lust fueled makeout session in no time at all.

“Girls, I know you are newly weds and all or whatever, but you are holding up my shopping.” Jessica joked after a long moment. “Plus, it is all lame that I don’t have anyone to makeout with.” Her eyes sparkled as she spoke the second part, clearly teasing the couple in front of her.

“Alright then.” Deedee pecked Tiffany on the lips one more time before stepping back from him. Her hands slipped from his body reluctantly. “You two go have fun. I’ll just be here, lonely and bored.” Her tone said otherwise as she moved to the couch and reclined onto it sensuously.

Taking the dismissal, and wanting to be out of her presence for the first time in twenty four hours, Trent moved out the front door swiftly. The sound of heels clicking along behind him let him know that Jessica was following along. As the door closed, a sigh escaped his lips, the stress of the morning fading somewhat as he felt a bit more free. “Young love is so cute.” Jessica’s voice cut through his thoughts as she moved up alongside him. The pair of beautifully clad feminine forms moved over to Jessica’s driveway, her convertible pink Ford Mustang sitting there waiting for them, the top up so as not to mess up their hair. “So, what kind of stuff are you thinking about picking up today hun?”

Already, the strain of walking in the heels was getting to Trent as he sat down into the car the way he had been shown the day before. “Like, maybe some different shoes?” Attempting to limit his responses, he decided not to elaborate on the fact that he wanted something without a heel.

The squeal of glee that escaped Jessica shocked him for a moment. “Oh my god girl, shoe shopping!” Looking over to smile at the pure glee that came out of the woman next to him, Trent’s eyes widened in shock. Just past Jessica, he could see another car pulling up to his father’s driveway. The little white Miata could only belong to one person. As the car he sat in roared to life, he reached for the door handle to get out before he heard Jessica speak up again. “Babes, I have to say, you really look amazing today. But you might want to fix that lipstick before anyone sees you. Kinda looks like you had sausage for brekkie, if you know what I mean.” She giggled and pantomimed like a dick was entering her perfectly made up lips.

Horror in the thought of someone seeing him, not just dressed like this, but with smudged lipstick that made it clear he had been busy with his lip kept him from getting out of the car. Looking up to the windshield, he noticed that the convertible lacked any sunvisors, and thus a mirror to see himself. Remembering the compact in the purse he was **** to carry, he reached in and pulled it out. Sure enough, the makeout session with his father had smudged the lipstick on his plump lips pretty significantly. “See babes, you can fix yourself up while I drive. Super easy.” Without giving him a chance to stop her, Jessica pulled the muscle car out of the driveway and onto the road, speeding past his father’s house.

Looking past the driver, Trent had just enough time to see Deedee open the door and greet his girlfriend Brittany as Jessica drove past, heading for the mall.