Trent handles it better than Deedee does

Trent’s eyes were locked onto the bulge in the skirt of the person in front of him. The fact that he was dressed in a slutty latex maid outfit, six inch tall locking heels, and had just had a butt plug shoved inside of him should have been the weirdest parts of this. Instead, it was the feeling as he stared forward knowing that he was the cause of the erection sitting only inches away from his face. As he stood there bent over at the waist with his hands placed on top of a white wooden stool, he realized he was at the perfect height for either end to be taken advantage of.

“Like, pay you back?” Going slightly cross eyed as his eyes focused on the tip bobbing in front of him, he could see a small dark spot in the thin dark cloth that indicated a certain level of excitement. Tearing his eyes away from the bulge, he looked up towards Deedee’s face. “Like, how?”

Staring down into her son’s eyes Deedee is shocked at the sheer terror she sees. The wall she created around her actions and the feelings she has tried to rely on shatters as she realizes what she was about to do. She knew how much he didn’t want this. Standing there frozen, she can feel the tears that are streaming down her face as she stares down at the person below her. Even as she lusts after the beautiful image in front of her, her emotions tear at her with each passing second.

The tears streaming down Deedee’s face streak her makeup and pool on her jawline before falling to the carpeted floor. Confusion furrows his brow. “Like, Deedee?” The fear in his voice combined with the **** vocal training makes his voice sound small and even more feminine than before. The two words carry with them all of the feelings that Trent still holds for his father, the sacrifices Derek made weighing heavily on him.

The short sentence breaks Deedee in half. She can feel her soul wrench in two distinct directions. She cannot help but be turned on by the person in front of her, but try as she might, she also can’t do what Chloe did to her. She won’t **** it on him like this. Closing her eyes tightly and shaking her head she walks from the room. Stepping out of the room and removing him from her sight, she pauses and speaks softly. “Get changed into something appropriate. You are basically naked.” Her voice is thick with disgust at herself and lust for the feminine form she can no longer see.

Stepping into her bedroom, Deedee slams the door and lets her emotions run wild. Wracking sobs consume her as she throws herself onto the bed and cries into her pillow. The sounds of her anguish are muffled by the cushion she holds to her face, and she only hopes that by the time Trent is done finding something to wear, she will have herself back under control.

Stunned by the outcome of the last few seconds, Trent stands up as he hears the door slamming shut behind him. One moment he was sure that he was about to be convinced that he owed her a blowjob, and the next she ran away crying. Standing there frozen he stares ahead into the mirror and sees the slut in it looking back at him. Even now he is cocking a hip to the side and posing almost naturally. Disgust in himself, in how easy he let this happen to him fills Trent.

Heavy breathing allows him to calm his nerves down enough to realize that while he may have avoided the impending phallus, he is certainly not out of the woods yet. Sudden revulsion at the outfit he is in snares his mind and he reaches down to rip the top off of, the latex stretches to slip over his large breasts and off of his body. Shucking the skirt just as quickly, he throws the tiny pieces of fabric at the discard stool and stands there naked. When his eyes finally open he sees the naked beautiful blonde bimbo staring back at him and a part of him understands where the lust in Deedee came from. Shaking his head, he does everything he can to discard that thought.

Feeling the need to cover himself, and following the orders he was given. Trent moves out of the line of the mirror, walking to the dresser and slides the top drawer open. The jumble of brightly colored panties staring back at him forces him to take a breath before moving on. Reaching down he carefully sorts through the snarl of satin and lace, his long nails delicately picking through them till he finally finds a pair that isn’t a thong or g string. The black lace cheeky panties take him a minute to pull on over the red stilettos that are still locked onto his feet. As he pulls them up and they settle over his cage, he has the feeling of something more like the boxers he used to wear for the first time in days.

Contemplating the next step in getting dressed like he knows Deedee wants him to, Trent opens the drawer below the panties and sees the bras all stacked carefully. Another deep breath allows him to gather the courage he needs to select his own bra for the first time. Reaching down and he finds a black lace halter top bralette, a part of him is glad that it matches the panties he already has on. Slipping it on over his head and settling the large breasts into it takes longer than he expected it to. Oddly, he also feels better than he expected it to.

Finally covered for the first time since being in Ana’s that morning, Trent eyes glaze over as he looks across the multiple racks of clothing. “Like, how am I supposed to pick something?” The valley girl accent slips out without notice as he strides along in his heels to search for something. The all black lingerie leads him to look through the collection of black outfits Deedee owns. Thinking about how difficult it had been to avoid snagging the delicate material of his panties, he decides a dress he can pull over his head would be best. Noticing a break in the dresses where it looks like someone had been searching through, he sees a black halter neck dress that looks like it would fit his search criteria. Seeing that it will actually cover more than either skirt he had on today, he immediately picks it off the hanger and shimmies it down onto his body.

Stepping back and looking into the mirror he sees a hot but much less slutty version of himself staring back. A frown crosses his face as he realizes the red heels he has on don’t match the look. Thinking to remove the heels, he looks down at the locks. Hoping that the keys were placed into his purse, he goes to check. Picking up the nude bag, he wonders when caring if his heels match or calling it his purse started. Telling himself that he is only doing this to get the locks off his heels, he searches through the bag to try and find the keys he hoped had been put in there by Ana or Jessica. The small bag and the items inside make searching difficult.

Deciding to dump the purse out onto a counter he sorts through the condom, makeup, and of course the tampon, but not a single key appears. Sweeping the contents on the counter back into the purse he tosses it onto the couch in frustration. Wishing he could just leave her alone and get through another chunk of the day without her, Trent knows that if he doesn’t rouse Deedee soon and head back to the mall it could be the next day, or longer, before he gets the cursed locks off the heels..

The sounds of the spiked shoes clicking off the hardwood floors in perfect rhythm is a calming metronome as he makes his way to Deedee’s room. There was something about the sound that brought a smile to his face. He had always despised when girls wore heels around him, even kitten heels would regularly take a woman to greater heights than nature had seen fit to bring him. Now he could feel the power and confidence that they brought. Shaking his head, Trent theorized that the feelings of power and confidence were simply his mind’s way of interpreting the amount of care that it actually took to sway his hips and walk the way he had been taught. He knew it was his way of lying to himself about the feelings that the plug inside of him and the swishing of his skirt were awakening deep within him.

His thoughts were silenced as he stepped into the room and saw Deedee curled up on the bed, her face shoved into a pillow. Turning to look up as she heard the door open Deedee’s tear streaked face met Tiffany’s new look and a look of confusion washed over her before she realized he had simply followed her parting orders. Feeling the strings in her heart fray, she laid her head back onto the pillow. “Leave me alone for a bit Tiffany. Just go practice walking or something. I’ll be out in a bit to get us some food or something.” The muffled sound was choked with emotion and just barely understandable.

Not wanting to bother her, but knowing he had to, Trent nervously played with his long nails as he stood there. He was unsure exactly what was going on with Deedee. There was still a part of him that cared for this woman in front of him. No one deserved to feel the sort of pain in the way that she appeared to be experiencing. Stepping closer he prayed that not following that order was the right choice. A hope that addressing it from a fashion perspective would soften any repercussions, he interrupted her misery. “Um, like, Deedee? These shoes like, totally don’t match and like, I can’t take them off.”

Confused at why he wasn’t able to remove the shoes, as well as the fact that Tiffany’s first worry was for the outfit not matching, Deedee sat up and swung her legs off the bed. Looking down at the heels he had on, she noticed the small gold padlocks securing the golden chain around Tiffany’s ankles. Trying to think of where the keys could be, she quickly came to the conclusion that they must still be at the mall. Standing up, she headed into the bathroom that was attached to her bedroom, pulling out cleansing wipes she got started cleaning up her ruined makeup. Her voice was strained and somewhat monotone as she told him the plan. “We can go run by Ana’s and see about getting you the key.”

Seeing that Deedee was obviously going through something but was willing to do this for him, he nodded and smiled his biggest smile. “Like thanks hun.” Turning around he wiggled off to give Deedee her space to get ready. In the mirror Deedee’s eyes widened at the term of endearment, shaking her head to stop herself from looking too far into it she got back to repairing the damage done to her makeup. Finishing with the process, she moved to the closet to put on something clean and more appropriate for the mall..

While she had been cleaning her face and redoing her makeup, Trent had thought about how to proceed. Moving into the closet he looked at himself in the mirror, it bothered him more than he would have liked that the shiny red heels didn’t match the outfit he had on. Thinking back to what he had just seen of Deedee’s mood, he tried to think about the best way to proceed. There was something about seeing her **** and in pain that had resonated badly within Trent. He wanted to see what he could do to make her happy. In his mind a happy Deedee was much less likely to do something awful to him. Looking over at the wall of shoes, he thought that if he picked out a pair to change into at the mall, it might make her happy that he was finally showing interest. Telling himself that it was only to please his captor, and not because of any sense of fashion, he turned to look at the choices.

Staring at the choices in front of him he felt overwhelmed with options. Was it better to go with the same color? He remembered something Brittany had said once about a statement shoe and it being a different color than the outfit. Another memory of her saying something about shoes bringing a pop of color filtered back into his mind as well. Playing with the hem of his skirt, he stood there rubbing the toe of one heel into the floor as he looked over all possible choices. Hearing Deedee’s heels on the floor, he looked up as she came in and sighed in disappointment at not having succeeded before she got there. “I like, wanted to surprise you.”

Deedee quirked a brow as she walked over to her closet and began looking for an outfit more appropriate for an evening out. Trying to keep her emotions calm, she focused on finding an outfit. Seeing Tiffany in all black, she began to sort through some of her lighter looks. “Surprise me with what baby?” Her response was somewhat automatic as she sifted through the clothes racks in front of her. Pulling out a dress she held it up and then discarded it again almost immediately.

“Like, picking out shoes for when I can get these totally locked ones off. They don’t match my dress.” Trent walked up to the wall and picked up a pair of black Casadei Blade Twenties. “Would these work?”

Turning to look she expected him to have chosen something she would not approve of. Instead when she saw the shoe he picked she nodded slowly in surprise at his choice. “Yes hun, those Blades are a great pick actually. They will class up the look, and the satin color goes with your dress and soft bare legs well.” Pulling out a dress, she shook her head again and set it back. Turning, she watched as Trent pulled the heels down. She could see an excited look on his face that he had made the correct choice. Inspiration struck and she stepped away from her clothes. “Tiffany, you are doing so well with your outfit, what would you say to picking out mine?”

Trent turned to look Deedee over, frowning as he didn’t understand what was wrong with her current look. “But you look fine, like aren’t we just going to pick up the keys?”

“Well yes, and perhaps some dinner. But you look so nice and I’m just in this messy wrinkled outfit that I’ve been in all day. Shouldn’t I look good for you hun? Since we are telling everyone you are my girlfriend. Imagine getting to pick out what your girlfriend wears for you. Doesn’t that sound nice?” Deedee stepped towards Trent and reached out to rest her hand on his shoulder softly, her large green eyes boring into his. “I want you to tell me what you want to see me in.”

Deedee’s touch on his shoulder sent another ripple of desire through his body as he tried to think about what he should do here. He knew that denying the choice would upset her and was a bad idea, but he had no clue on what to select for an outfit. Chewing on his still darkly painted lip, he stepped up to the racks. “So like, anything?”

“Well, anything except that costume you wore home for me. That’s yours, not mine.” Deedee giggled at the thought of that tiny skirt trying to contain her. “Go for it though hun, I will reserve veto rights, but I like to think I can rock anything in here. Even if I am not a hot little 18 year old anymore.” She was interested in how he would deal with her pushing him like this.

Trent stood there thinking about what to select. The amount of choices was overwhelming. Thinking over all the outfits he had seen in the last few days, he was reminded of Jessica’s all white outfit. He remembered Deedee saying something about it being nice that morning. Seeing a number of white dresses, he reached his hand out and drew it across the hangers until something stuck out at him. Pulling the white off the shoulder sweater dress he thought about what she would look like in it. With her large gravity defying breasts and the short hem, Trent knew Deedee would look amazing in it. The dress was also different from the look he was currently in. Off the shoulder versus the halter neck, tight skirt vs pleated and flowing. Nodding in satisfaction at his selection, he turned and held out the hanger to her.

“Interesting, you want me in something tight huh?” Giggling, Deedee reached down and pulled her top off. Trent’s eyes almost popped out of his head as her large breasts bounced free, the pink areolas stiffening in response to the open air as she stood tossed the top to the side. Pushing her split skirt down just as startlingly, she stood in just her heels in front of him. “Is this all? What else will it be, a dress does not make an outfit hun. I’m not going barefoot.”

Trent’s mind was spinning out of control as he stared at the woman he had made out with earlier. The memory of their lust filled makeout session fogged up his mind as he looked her over. Her older body was taut from hours spent working out, the breast implants she had sat high and proud on her frame. It was easy to see where he had inherited his tiny waist and voluptuous ass from as well. None of those were what caught his eye though. The thing his eyes locked onto was the part of Deedee that quite literally stood out. His lips parted as he sucked a breath in, watching her cock solidify in the air between them. “It looks like you think commando might be best. Bring me the dress baby.”

Swallowing, he stepped forward handing her the clothes. The plug inside of him bumped into him just right as he stepped over to her and he could feel his own penis trying to swell in its cage. Handing her the dress, he looked behind her at the wall of shoes in an effort to distract himself from her naked body. Seeing a pair that caught his eye, he reached out and selected the pair of heels he thought he had worn the first day, thinking the pink and white would work well together. Deedee, now done shimmying into the tight dress, turned to look at the shoes Trent had selected.

A sharp intake of breath was the only indication Trent had that he may have chosen something special. Stepping over to her chair, she sat down and removed the heels strapped to her feet quickly. Trent looked and watched her as she walked over and set the previous pair into their spot on the wall, then she pulled down the hot pink 130mm Hot Chick hees. Holding the bright pink heels, in her hands, memories came back to her. These had been her “graduation” present from Miss Jameson, the acknowledgment that she was no longer and never would be a man again. While certainly not her highest heels, they were the highest heels she had without a platform, and some of her most difficult to walk in.

“These are what you want me to wear? Are you sure?” Something about this choice seemed right to her, but she wanted to be sure it was something he wanted from her. Turning to him, she stood holding the bright pink heel out. Trent’s eyes were locked on Deedee as she stood before him. The fact that he stood taller than her in his platforms, now that she was barefoot, felt slightly off to him.

“Like, aren’t they the ones I wore yesterday? I thought it would be cute to like, share.” The idea had come to him while he had been selecting her dress, before she had short circuited his brain with her nudity.

Shaking her head at his question, she slipped the exquisite heels on and stood up straight. “No baby, these are my favorite heels. They are a bit hard to walk in, but they are very special to me. These are actually even higher than the pair you wore yesterday.” Pulling out a box for the Casadei Blades, Deedee slipped the pair of heels into it then placed the box in a bag. Now that they were fully dressed, it was time for them to head to the mall. Motioning for Tiffany to follow her. “Let’s go get your keys hun.”

Sorry about the long time between post lovelies. I had some stuff come up in my head that made getting through this part harder. Plus the story took a turn I had not anticipated so it took me longer to move through it. Hope you all still enjoy it even if the sexy stuff is still to come. Bare with me, it will cum. I promise!