First day dressed

Standing there staring at the pile of women’s clothing, Paul tried to contemplate how he got here. It has effectively doubled his wardrobe Trainer Bill had gotten him, yet all of this was definitely no pretending or skirting around the fact it is definitely feminine. While he was wearing the tight, half-tank & short booty shorts in bright green with his wedged sneakers that only gave a brief impression of exercise outfit even though he just finished several rotations of squats and various yoga poses. Examining the dresses, some of them even looked close to what he saw Molly off in this morning after saying their goodbyes. Yet here he stood with her voice playing in his ear and about to spend his own day working wearing similar clothes to get comfortable in it.

Shaking his head and reminding himself it's just clothes & he’s just wasting time. Grabbing a white gaff and black bra, he grabbed a black blouse & white skirt. Opting for a black belt and darker corset, he grabbed the wedges to get dressed. Realizing he was a little sweaty, he went to shower to get clean first; though he wondered if it wasn’t just a self-delusional delay too.

Getting out of the shower, he applied the berry oil and was rewarded with the familiar tingle and relaxed deeply. Putting his earbuds back in, he could hear the vocal practice track still running from this morning's work out and took some comfort in his wife’s familiar & excited voice. Walking over to the pile, the bra & inserts caught his attention first, so he started with those.

With the protrusions in place, he grabbed the gaff and pulled it into place. Blindly feeling his cock and trying to ensure it lined up right took several attempts and shifting to get something close to comfortable. However, he quickly realized that he hadn’t installed the gadget or aid, and he should probably do that before messing with the corset. As he turned to leave, his foot kicked one of the wedges sitting on the floor, so he figured he might as well put them on to practice.

Walking to the other room to get the gadget from its charger, he slid it under his tucked cock letting the gaff hold it all in place. As he turned to the aid, he was reminded about Trainer Bill’s instruction to move up to the next level, so he sighed and placed the last aid next to the others in the set, he grabbed the next largest one and went to get it installed.

Kneeling down on the floor, he tried to put his face on the ground like normally, but he found the inserts were making that too difficult, so he just rested the side of his head on the floor tiles. Reaching back to heavily lubricate his back entrance, he also slathered it over the cover protecting the new aid. He could feel a weighted difference in his hand as he lined up the aid. Taking several long breaths trying to relax and let the calming sensation wash over him, he slowly pressed it in. He was able to get it pretty far in as it felt similar to the previous one, but he encountered resistance as she got closer to the marge base.

Sliding it back out quickly but keeping the tip inside, he tried to breathe quickly and calmly to minimize the tension building in his body making this even more difficult. As he felt the calming energy flow over him again, he started pressing in further. As he met resistance, he pulled back and pressed in further again trying to breathe out and press back on the encountered pushback with the aid. Repeating this process again and again, he was finally rewarded with a near pop as the widest point made it past his sphincter and his body pulled it quickly in and yelp a bit as it hit home.

Walking carefully back to his outfit for the day, he was highly reminded of his intimate training aid and swished his hips wide trying to compensate for it. With each step he could feel it rub against his insides and it was feeling not entirely unpleasant even if persistent.

The corset was definitely adding to the strictness of his movements, but the contortions & pulling required to tighten it behind him was stretching his flexibility. As he tried to get back to the point Trainer Bill wanted, he felt like he was about to pop a shoulder out of joint, but tied it in place as he caught his breath. Grabbing the top and stepping into the skirt, he finished off the outfit with a belt before returning to his stash for the final pieces.

With the wig in place, he used the lipstick like chapstick and painted his nails like the old models he used to do. Getting polish on his cuticles more than once, he was surprised at how difficult it was to get his non-dominant hand right. Attempting to brush on some blush as he had seen Molly do time and time again, he got up to get to work. He knew he should probably have been using a mirror to get it right, but he just couldn’t face himself. He really didn’t want to see some old guy looking like a clown, so figured he’d just leave it as is.

Sitting down, he cautiously sat slowly while the aid pressed in further to his internal tunnel. Wiggling his hips side to side returned the not-unpleasant feeling within him and it took an unusual amount of focus to get going on work. Within 5 minutes of typing away, he was seeing flakes of red on his keyboard. Looking at his nails, the tips of his short nail plate were jagged and messed up. Feeling it with his other hand, it was a bit tacky to the touch.

Standing up, he walked back to his stash enjoying the airy feeling of his skirt as something continued to stimulate from inside himself. Putting polish back on the tips to cover up just the jagged edge. Taking time to blow on them like he had seen his wife do as he walked back to his desk, his mind wondered to watching Molly purse her soft, wet red lips blew on her nails.

A particularly vivid memory washed over his mind as he absentminded continued walking through their home. Remembering himself walking in on her as she finished and seeing her blow on her nails, dressed in a hot little clubbing number they were about to go out in. He stopped in his tracks as he suddenly found himself panting in the kitchen. Closing his eyes, he could remember Molly reaching out with her freshly painted nails to grasp his cock. Standing in the kitchen, his breathing increased in intensity as he began twisting his hips and rubbing his legs together trying to get the gadget to make room for his flexing cock, but the gaff held in place as he could feel a stimulation inside himself increasing the building pressure. Remembering the familiar feeling of her velvet, painted lips wrapping around his cock.

Momentarily losing his balance, his eyes flew open as he reached for something to steady himself. Grasping out he catches the broom handle left out from this morning’s clean up and steadies himself. Seeing the bright red nails wrapped around the hard, tan wooden shaft, his mental replay of Molly attending to his wood flashed in his mind. Jerking his hand back as if he were touching a snake, Paul shook his head tried to get his head back in the game, feeling the crimson locks hit his face and catch on his lips. Trying to take a calming breath only to feel the plastic strands enter his mouth, he pulls them aside getting himself collected.

Taking a final moment to compose himself, he slowly returns to his desk trying to ignore the invader while keeping his steps appropriate. Sitting down cautiously at his desk, he inspects his nails carefully before returning to typing. Stopping after a few minutes, he was pleased to see the nails still seemed to be holding up and focused on work.

He continued diligently until his alarm went off at the usual time. Realizing he doesn’t need to do much to prepare today, he looked back at his nails and saw they were chipped and flaked again. Not wanting to look grotesquely off, he retrieved the polish to repair them as he blew on his nails dry.

Slowly getting into a kneel in his usual spot, he waited for Trainer Bill to connect. Afraid of what he’d say about the clown makeup, he hung his head and tried to direct strands of faux hair to hide his face.

“Ahh, hello, Paulie!” Bill called to the kneeling form with bright red nails & long red head bowed before him.

“Hello, Trainer Bill,” Paul replied timidly as he continued to stare at his knees.

“Everything okay, Paulie?” Bill asked sensing the ****.

“It’s alright, Trainer Bill. Just ready to get going.” Paul tried to keep his face hidden.

“Paul,” Bill moved to a harsher tone, “look at me.”

Paul fiddled with the hem of his skirt biting his lip. His face probably looked a joke, but he wasn’t sure if it was really the embarrassment of looking at a joke or shame of disappointing his training partner. A penetrating ZAAP went through him as a gasp escaped his mouth.

“Paul, when I tell you do something, you need to do it. Look at ME,” Bill forcefully commanded.

Slowly Paul raised his head to literally face the music but couldn’t bring himself to open his eyes.

“Much better, Paulie.” <BUZZ>

A gasp escaped Paul’s tinted lips as the vibration from the Gadget traveled through his tucked cock reverberated through his pelvic floor and sent waves against his training aid. This sent shivers up his spine releasing a new euphoric feeling.

“Now open your eyes and look at me, Paulie.”

Slowly, Paul’s eyes opened with a flutter. As his eyes focused on Trainer Bill’s, the gadget vibrated.

“Very good,” Bill encouraged. “Now what is the issue.”

Realizing Trainer Bill had seen it but hadn’t broken up, he had no more reason to hold back. “Trainer Bill, I was worried about this makeup,” he replied quietly.

Bill chuckled a bit, “Is that all you were worried about?”

Paul nodded silently in response.

“Okay, ya, you’re going to win any pageants, but I’m not expecting the freshman to score the winning touchdown in the first game. I didn’t expect it to be perfect.”

“yes, trainer bill,” Paul meekly responded, almost more ashamed of being afraid than the lackluster job.

“Your lipstick is a little messy, the nails are kinda rough, and the blush is kind of blotchy, but you can get that with practice. Watch a few YouTube videos for suggestions. Just basic, daily type stuff. Nothing fancy.”

“Yes, Trainer Bill.”

“Alright, enough of this concern. You’re looking comfortable and the outfit looks good. Let’s start some stretching and practice that walk.”

Encouraged by the praise, Paul eagerly stood up and got to work, “yes, Trainer Bill.”

Working with the praise and the newer aid was causing Paul to have an extra spring and sway in his step. At the end of it all, Bill had Paul return back to the close out.

“K, it was good work today, Paulie. Don’t let your new tasks get you discourage, but still give it your best ability.”

“Yes, Trainer Bill. I will.” <BUZZ>

“Good girl, Paulie,” Bill responded almost habitually. “So, keep up your morning routine and daily outfit training.”

“Yes, Trainer Bill.”

“Talk to you tomorrow, Paulie.”

“Bye, Trainer Bill.” Paul felt better about the day and hopped through taking care of clean up, laundry, and dinner before changing out of the girly clothes. Molly enjoyed the dinner and evening with her husband, having a quick romp in bed before cuddling to sleep.