Defining daily practice

Paul stands there staring at the training clothes before him. He and Molly had a great relaxing weekend alone, but their bouts of fun between mundane tasks seemed to make the weekend go all too quickly. Molly got out to work without any real issue, and now he had to figure out which outfit to wear before Trainer Bill’s next order of clothes came in. Something about the yellow kilt seemed to call to him, but it was less a clue to any interest than just seemed familiar.

Grabbing the matching tank top and thong, he put on his sneakers & vest, and went through his stretching routine. Feeling refreshed and ready for a day, he got to work.

Hours passed before Paul even realized how much coding he went through only to be broken from his focus by a ring from the front door. Looking out his front camera, he sees a delivery driver walking away.

As the time was about to trigger a reminder for his upcoming training session, he took that as a good time to go ahead & save his work and get ready. Setting up the audio & putting in the airbuds beds as he started the vocal loop before heading to get fully dressed. Putting on a shirt and swapping out boots for his sneakers, he grabbed the gadget & aid. Taking a deep breath after installing the aid and enjoying the pleasant rush, Paul returned to their setup and kneeled in his spot pleasantly waiting for Trainer Bill.

Paul wasn’t waiting very long before his idle thoughts were interrupted with “Hey, Paulie.”

“Hello, Trainer Bill.”

“I noticed you’re in the kilt and shirt still; was there a problem with your new clothes? I got the delivery notification earlier.”

Paul was visibly flummoxed by this; was he supposed to get that stuff first? Did Trainer Bill tell him to? “Uhm, no, Trainer Bill, I just saw the delivery driver walk away a bit ago but didn’t think to get anything before this.”

“Well, no time like the present; go get the delivery and we can go through it together.”

Paul cheered up the idea of doing the task with his training partner rather than alone, so he eagerly responded, “yes, Trainer Bill!” and stood up to go get the delivery.

As he approached the front door, he froze and stared at it for a second. He ran out to the salon in an outfit like this, but the idea of everything that went wrong ran through his head. However, he realized Trainer Bill was waiting for him and he needed to get comfortable.

Opening the door, Paul was expecting a box to bring in; however, he was greeted with almost a dozen packages including a few large boxes and several plastic envelopes. Looking at the packages just splayed around, he squatted down to organize them, but was quickly reminded of his aid pressing deeper into him by the thong’s pressure. Taking a few calming breaths, he reached over and gathered everything into a large stack. Pressing his chin into the top soft package, he gripped the bottom and lifted up his body with his legs lifting his body and all the packages in one go.

Pushing down the door handle, Paul struggled keeping the pile together and swinging his hips, so he took very cautionary steps, feeling the aid comfortably rubbing up against his insides. Nearly shuffling back into the room, Paul tries to gently set it all down only to have the stack fall all around the place. “Shit,” Paul exclaimed as he knelt down to gather all the packages back into at least a semi-neat pile.

While he was gathering this together, he had to reach out to grab one package that slid almost halfway across the room. Bill was ‘treated’ with a view up the yellow tartan kilt and was pleased to see the tone and strength the exercises & stretching seemed to be giving Paulie.

With everything now apparently in a pile before Paul, he sat with his knees spread appearing like an excited child ready for Christmas morning opening. “This is sooo much, Trainer Bill. Thank you so much for getting it for me, but it seems like a lot.”

“Oh, it really isn’t as bad as it looks. I’m sure a lot of it is just their packaging. But let’s go ahead and go through it.”

“Yes, Trainer Bill.” With that, Paul grabbed the package on top and ripped into the package envelope. Pulling out the contents was a couple shirts with capped sleeves; one red & one purple. Paul could see some similarities to some rather causal tops Molly though not too far from his t-shirts.

“Ah, some basic tops. Next.”

“yes, Trainer Bill. Thank you.” Paul said placing them to the side and grabbed the next package. It had 3 pleated skirts (black, white, and blue), but appeared to be clearly shorter than his kilts.

“Simple skirts. Good. Next"

“yes, Trainer Bill.” Placing them below the shirts to see some obvious outfits, Paul grabbed the next package and found a basic red wig with straight strands that would easily go down his back. Alongside the wig there was an array of headbands in various colors.

“Nothing fancy to worry about upkeep, but get you used to the feel & weight.”

“Oh. K.”

“Next”

“Yes, Trainer Bill,” Paul said as he placed the wig over the shirts. The next package produced a couple of flowery sundresses in a fit & flare style.

“Very cute! Those should work well. Next”

“Yes, Trainer Bill,” Paul set the dresses next to the tops & bottoms. Trying to contain his nerves as this seemed to be growing, but directed on by Trainer Bill, he opened the next package. Several makeup products came out including lipstick, nail polish, blush, mascara, base, etc.

“These are just a basic set to let you practice. Katie will give you a professional setup the day of, but would do you good to know the basics so you can repair something if needed. Next”

“yes, Trainer Bill.” Paul could barely keep from freaking out at the idea of having to do make-up. The next package yielded what appeared to be padded thongs. 3 black, 2 tan, 2 pink, and 2 white.

“Ah, the gaffs. These will allow you to tuck things away and keep them flat.”

“Oh, okay. Um, thank you, Trainer Bill.” Paul was really feeling a bit overwhelmed.

“Go ahead and get that first box open.”

“yes, Trainer Bill,” Paul moved the trash out of the way, and focused on the boxes. Opening up the box revealed a bag of 4 wide-elastic belts, 7 bras, 2 corsets, 3 wide bands of cloth, and another box.

“Those are probably the main reason I got you the gaffs instead of normal panties.”

Paul noticed that the bras seemed to match the colors of the gaffs, “They didn’t have others that matched the bras, Trainer Bill?”

Bill shook his head for not catching it, “no, Paulie, the skirts.”

“What skirts, Trainer Bill?”

“Uh, those right there. The red one, black one, and white one.”

Paul’s attention turned back to the bands of cloth and picked them up. “These?”

“Yup”

Paul held them up and looked at them, “these are skirts?!? They look more like belts, Trainer Bill!!” Laying one down on his lap, it appeared to go from his waist to his upper thigh.

“Don’t worry, Paulie, they stretch.”

Paul just looked at him with fear in his eyes.

“Paulie, they’re just for training later. It's not like I’m expecting you to go out in them. Trust me.”

Paul picked up the skirts like they're radioactive and placed them with the other skirts. He had to do a double take when he saw they seemed to fall an inch or two shorter than the others. Shaking his head, he grabbed the belts, bras, and corsets out placing them with the other outfits.

“I was glad I was able to find those on sale. Take out the box and check them out.”

“yes, Trainer Bill.” Pulling out the box, Paul is surprised to find two orbs of tan looking rubber-like substance staring at him. His brain was still trying to process what he was seeing.

“Those forms should fit perfectly in the bra and let you get used to having extra weight up top.”

Remember back to what Katie had used on his chest before these seemed almost rigid and cheap, but still, he picked one up and held it up against his chest. Amazed at the size he looked back to Bill, “is this size really needed right now?”

“Paulie, those are only D-cup. They’ll look fine with your height and build.”

“uh-huh.” Paul felt a zap and jumped from the jolt. “Sorry. Thank you, Trainer Bill.” He corrected himself.

“Open the next big box.”

“Yes, Trainer Bill.” Paul again set the box of faux boobs to the side and moved the packaging out of the way to open the last box. Inside, he found two large shoe boxes. Taking out the first one, he found a cork wedged sandal in black. The height and angle of the shoe made the wedge look absolutely enormous to Paul.

“Ah! The wedges. Those should still work well on the treadmill but let you feel a bit more style.”

“Oh. Thanks, Trainer Bill.”

“Open the other shoes.”

“Yes, Trainer Bill.” Paul opened the remaining box and exposed a pair of shoes with blocky black heels that were easily as high as the wedge without a platform to help the balls of the feet elevate.

“Those will be more for times when you’re ready for them, but I don’t think they’ll be valid on the treadmill; guess you could think of them more as house slippers to walk around your home.”

“Thank you, Trainer Bill,” Paul replied totally flabbergasted by all this stuff.

“Remember, the idea here is to get comfortable at wearing these now, so when it comes time for the party, the clothing will at least seem more normal and not quite so foreign. Moreover, you’ll be able to move and adjust without it being totally awkward the day of.”

“Yes, Trainer Bill.”

“Grab the red top, black belt, black skirt, gaff, bra, corset, inserts, & wedges and put them on.”

Taking a deep breath, Paul looked at all the garments before him and just wondered what he was really setting up for.

“Paulie?” Bill was losing patience, “we don’t have a ton of time and still haven’t done anything.”

Paul could detect the irritation in his voice and grabbed the listed clothes as he quickly replied, “yes, Trainer Bill, sorry.” Paul then stood up and turned to head out of the room to go change.

“Wait, stop!” Bill called out into Paul’s earbuds.

“Yes, trainer Bill?” Paul stopped in his tracks.

“We don’t have time for you to run around and it’s likely you’ll have issues with some of this if you haven’t worn them before. Get changed here so I can help you.”

Paul reluctantly turned on the heels of his boots and held the pile of clothes before him trying to use it as a barrier between him and Bill trying to figure out what he was after.

“Paulie. Put the clothes down on the table.”

Paul, dazed a bit by this, set them on the desk.

“Now remove the shirt.”

Paul pulled it off and set it to the side. <BUZZ>

“Now remove the top and vest.”

Paul obediently removed the tight half tank top and training vest and received a <BUZZ BUZZ> as he set them with the shirt. Standing in the kilt and boots, he stared at the screen wondering if he really wanted to keep doing this.

“Now take off your kilt.”

As he slid the kilt down his legs, he had to fight with it as the boots kept catching on the kilt but finally got it out before falling over.

Seeing the clunky items come into view, Bill had to shake his head that Paul didn’t actually bother to take them off. “Remove the boots and socks, too, Paulie.”

“yes, Trainer Bill,” Paul replied as he quickly removed them and set them to the side feeling several quick <BUZZ BUZZ BUZZ BUZZ>. Standing up, Paul tried to wrap his hand around him protecting himself standing there in only his yellow pouched thong.

“I’m glad to see your muscle tone is really coming through. I hadn’t had a chance to see it much since we moved to the kilt and shirt,” Bill noticed to try to ease his client some.

Paul could feel a bit of a flush run to his face as his training partner was praising his work & noticing improvement. “thank you, Trainer Bill. Your guidance has been invaluable.” <BUZZ BUZZ BUZZ>

As Bill noticed him relax from the buzz, “set the Gadget aside as well.” Bill noticed a shock look on Paul’s face and took it a disappointed. “Don’t worry; we’ll come back to it in a moment.”

“yes, Trainer Bill,” Paul nervously replied reaching into his underwear to retrieve the gadget and placing it with the other items.

“Now, remove the old thong.” Bill knew this was a little risky, but Paul really needed to get over his timidness with Bill and it's likely it would help him identify the new clothes as a preference. Seeing him stand there without doing it, “come on, Paul. Just like the showers after a good workout session. Nothing to it. Just us here.”

“Yes, Trainer Bill,” Paul replied timidly. He was always a little apprehensive during the shower sessions before. Bill always was a better physical specimen working out frequently and Paul being more desk bound. He rarely stayed naked long and tried to avoid being seen in the locker room, but he was about to be that way standing in front of his paramour remotely in his office. Taking a deep breath, he grabbed the waist band and quickly bent over to slide them down to his ankles. However, as he reached down there, he felt is one remaining addition begin to slide out as the thong was not there pressing on it. Quickly reaching behind himself, he pressed the aid back in as he stood upright before the camera.

Trying to catch his balance a bit, he felt his ankles tug against each other a bit as the underwear was still wrapped around his feet. Taking a quickstep out with one foot, he kicked it to the side before he fell over.

Gaining his balance, he had one hand stretched out trying to balance his weight while the other was still holding the aid behind him. Suddenly he realized he was standing at half-mast before Trainer Bill.

“Now, grab your new gaff and pull it up to your upper thighs, but stop before you go the rest of the way on.”

Grabbing the black gaff, he tried to minimize bending over as he stepped into and pulled it up before reaching his crotch.

“Okay, now this is pretty good at hiding things, but you should most of your mass between your legs.”

Paul looked at him like he was speaking a foreign language.

“Don’t become an idiot now, Paulie,” Bill admonished. “Reach down and fold your cock down between your thighs and hold it there.”

Paul was at least glad he was able to cover up with his hand as little as he could.

“Okay, now press your balls in some and the cup those with your dick with that same hand.”

Paul could feel his balls go back into his cavity some as he pressed them and then moved his hand to cover them and his cock.

“Now, with your free hand, pull the gaff up to cover your hand, then slide your hand out while the gaff holds things in place.”

Paul did as instructed and could feel things press behind him as well as the thong press into the aid as he finished tugging the underwear into place. Looking down to inspect things, he was amazed to see only a small mound where he would normally see a small appendage.

“Okay, grab the bra and put it on.”

Picking it up, he undid the clasp and put it around backwards like he had seen Molly do over the years. Spinning it around and putting the shoulder straps up, the cups hung very loosely below it.

“K, we’ll come back to adjust it in a bit. For now, grab the corset.”

Having helped Molly with several over the years, Paul quickly loosened the laces before undoing the hasps and wrapping it around him. Locking it up the front, he held it with one hand while grabbing the loose laces behind him. Chuckling a bit at himself as he was tightening it, “this is a lot easier when doing it on someone else.”

“Heh, I bet it is. But I’m sure you’ll get it with practice”

Finally tightening it on himself, he tied it off and left it.

“K, almost forgot, grab the gadget and install it down your gaff.”

“Yes, Trainer Bill.” Paul grabbed the tool and slid it down the underwear careful not to lose pressure on his appendage. Pulling his hands out he felt a <BUZZZZZZZZ> and felt his knees buckle a bit.

“Very good, Paulie. Now grab the inserts and put them in the bra.”

Picking up the flesh-colored blobs he put them in the bra and tried to adjust them to fit right.

“Adjust the shoulder straps until they’re tight.”

Realizing that tension needed there too, “oh, thank you, Trainer Bill.” Paul finished adjusted the top and shifted his top a little.

Bill noticed the skirt was shifting a lot around his side. “Paulie, turn around, I need to check something.” Turning around Paul exposed at least a couple inch gap between the back sides of the corset. “That’s going to cause a problem; Paul you really need to tighten that corset more. Untie it and pull it tighter.”

“Yes, Trainer Bill,” he replies. Several iterations later and feeling like he was either about to pop his shoulder out or break the laces, Bill finally relented and let him tie it off.

“K, you pulled in an inch or so, but note that it should be tight like that if not even tighter. We might need to do more crunches to make it fit better. Grab the top and then the skirt”

“Yes, Trainer Bill,” Paul replied still trying to catch his breath. He wasn’t sure he could get it much tighter than this but was worried at how disappointed trainer Bill sounded. Popping the top over the faux chest, the wide neckline was obviously more feminine than his shirts but clearly hid any cleavage to keep up the disguise. Stepping into the skirt, he slid it up to his hips. Looking down it seemed to almost reach his knees, but there was still a gap between the top and skirt that not even the belt would cover.

“Paulie, that needs to rest at your waist. Pull it the rest of the way up.”

Paul looked down and was surprised but pulled it up another couple of inches just grabbing the hem of the top. Shifting his weight left and right, his eyes bugged out as could feel the loose skirt hitting well above where any kilt he wore did and was at most mid-thigh.

“Wrap the belt around to tie them together,” Bill interjected to distract him and keep him going. As Paul finished struggling with the belt trying to look over his new chest, Bill kept it going, “now slide on those wedges.”

Picking up each wedge off the table, he brought up each foot to slid them in. Feeling his perspective shift as soon as he stepped into the shoe, he was surprised at how much lighter they were than the boots and felt almost springy in comparison.

Bill watched his chest and skirt bounce a bit as he tested his shoes. He didn’t have time for Paul to go through everything, but he had a sense about something. “Grab the wig and a black headband.”

Taking his first few steps in the new shoes the short distance to the wig careful to avoid his new clothes and packaging. Starting to bend over, the stiff boning of the corset suggested otherwise, and he squatted down feeling the gaff push the training aid again as the gadget pressed his cock further into his taint. Standing back up, he looked at the wig for the front and tossed it over his head like a hat. Putting his headband on like he’d seen Molly do, he slid the soft fabric behind his ears before turning back to Bill.

Seeing the red mane fly Bill was impressed by the change even though he saw it. He wouldn’t be winning any pageants, and anyone could clearly see it was a male face above what looked like a woman’s body with long, toned legs. The hair helped the illusion, but with the face he could almost be accepted. However, that was quickly lost as Paul started messing and pulling on strands of the cheap wig that had flown into his mouth. Almost looking like a crazy guy fighting an illusionary wasp, the façade was quickly broken.

“Alright, we’ve lost a lot of time, but let's at least spend some time on the treadmill.”

“Yes, Trainer Bill,” Paul replied quickly stepping around the carnage on the floor before getting up on the treadmill.

As he punched in the speed and started the machine, he looked up at the mirror installed in front of it and was amazed by what he saw. Gone were the large legs in big boots under a kilt. Instead, he could see a cute mini skirt shifting side to side with each step as elegant legs took comfortable strides in sensible wedges. He could even make out the bottom of crimson covered boobs and red strands of hair moving in the background. As he watched this, the continuous vocal track was playing still: “I am beautiful. I am wonderful. I am sexy...”

“Good to see the training wasn’t for naut,” Bill praised as he was surprised at just how feminine he was already looking from back here. “Keep up the strides and swing your arms a little.”

Paul, shaken out of his daydream, suddenly realized his hands were still on the console even after several strides, but quickly brought them down as instructed. Unfortunately, the ‘man hands’ really clashed with the rest of the vision. Remembering how the girls had him walk from the salon with the bags, he lifted his arms up at the elbows and started swishing even more. With his hands up and out of the reflection, the illusion of the lady in the red top & miniskirt was re-established.

“Good, Paulie, but what is with the hands.”

“It was just something the girls at the salon suggested, Trainer Bill..... I just didn’t like the way the hands looked with the rest of it.”

“Well, you can practice nails and makeup tomorrow, and that should help with it.”

“Yes, Trainer Bill,” Paul tentatively responds.

Bill let him continue for about 15 minutes before calling him back over to close out. Paul gently moved the trash out of the way and made sure the new clothes weren’t stepped on. Gently kneeling down he could feel the aid pressing further into him. Settling with his cheeks on the wedges, he spread his knees to extend past the marks. As he stared at his knees, strands of red hair fell into his view. Brushing the hair out of his way, he tried to pull the hem of the skirt down as it rested above midthigh as he heard Bill speaking in his earbud.

“Well, it was pretty good today, but got plenty of work to do & not a ton of time to do it in. Remember how you were concerned about being comfortable in the proper attire. If you’re going to be in a room full of people, you need practice getting comfortable in the style. Therefore, I need you to spend the extra time we talked about to get more comfortable.”

“Yes, Trainer Bill.”

“Here is what your daily schedule needs to be. Get up and do morning with Molly like you normally do. When she leaves, do your morning exercises and stretches in your workout gear, then pick out an outfit for the day. Include the gaff, corset, bra, inserts, shoes, wig, and belt if needed. Also, work with the polish, lipstick, and mascara at least; watch some vids if you need instructions. Spend your day and do what you need in the clothes; get used to them. If you can, get dinner & things ready before Molly gets home, but, above ALL else, make sure you are completely changed out & cleaned up before she gets home. We can NOT have her see you before we’re ready.”

“Yes, Trainer Bill.”

“Also, I noticed the aid is getting a little loose, so start the next size; it's been about long enough.”

Paul got nervous again and swallowed hard as he wiggled his hip feeling his current aid, “next size, Trainer Bill? Up?”

“Yes, Paulie, next size up. As I mentioned before, if you don’t adjust it up, you’re going to get too comfortable with it and it will become ineffective.”

“Ye... yes, Trainer Bill.”

“Alright, we’ve taken enough time today. Plenty of work to do but we can get it done just keep up the homework & sessions, and you’ll amaze your guests & Molly.”

“Yes, Trainer Bill.”

“See you tomorrow, Paulie. Good-bye.”

“Bye, Trainer Bill.”

Standing up, Paul looked at all the package & clothes and figured he better clean things up. Trying to bend over proved harder than expected with the corset and ended having to squat down again. As he was in the squat, he could feel the gaff getting tight against the gadget and aid.

Getting all the trash in the big boxes, he took it out to the trash dumpsters in the garage. Returning back, he saw all the new things Trainer Bill got him and just sighed.

Gathering up all the clothes and putting them with his other gear. Looking at all his gear, he was reminded of the warning from Katie to get a lock so as not to be discovered. The idea of Molly walking in and finding all that seemed like a nightmare. He thought about getting a lock for a closet, but that just seemed like a bad use of limited storage.

Returning to the office, he sat at his computer and looked up lockable cabinets. Browsing around, he found some gun cabinets with keyed locks that looked good without outrages prices. Setting one up for delivery, he panicked as he saw the time and quickly got up. Swishing swiftly to the kitchen, he could feel the breeze blowing up his skirt, and tried to hold it down.

Getting together a basic chicken and rice dish, he found himself extremely hot and very tired by the end of the cleaning. With the wig matted to his neck and chest, he found the heat from the stove constantly building up under his hair and the corset & inserts were hardly letting his body ventilate the heat.

Seeing the time, he quickly rushed out and got his clothes removed. Getting all the training and aids cleaned, he quickly ran them across the apartment to hide it, before running back. He just got enough time to run back and grab his usual shirt and shorts in time for Molly to get home. Finishing dressing in the restroom, he finally came out to find Molly snitching dinner; “it good?” he questioned.

“MMmmmm, obviously Master level chef,” she replied as she wrapped her hands around my neck and began kissing me deeply. They quickly proceeded to dinner before retreating to a dual shower before a lively bedtime.