Even without a memory, Ashley can’t choose the super pink girly outfit…. Yet

Ashley pondered for a moment. The pink outfit was obviously the girliest and Paige said he should be a girly sissy. But even then, something inside him railed against the super feminine and frilly pink outfit. It sounded like it didn’t like either outfit, which was odd since Ashley was a girly sissy, or so Paige told him he was. But it was louder when looking at the pink monstrosity.

“I think the white outfit is cute.” Ashley said aloud.

Paige, a little disappointed he didn’t go with the pink one, was still happy he chose either outfit. Her plan was working better than she expected, even with out him choosing the girly girl pink. Paige clapped her hands excitedly and squealed.

“Oh goodie! It is a much more tame outfit. And with you just exploring girlhood it makes sense. I know you’re SO SO SO excited to wear it all, but let’s get you in your lingerie first and then we’ll do hair and make up. Then we can get you fully dressed.”

Ashley just nodded, still staring at the super feminine outfits. There was apprehension inside him and he wasn’t sure why. Paige said he wanted to be a sissy and she was helping him. And she was happy getting him more girly, and he loved making his best friend happy, so why was a small part of him upset?

Before he could think about it more, Paige gave him a light spank on the butt, making him yelp!

“Eeeep! What was that for??” Ashley cried out.

“You weren’t listening to me, Ash. You know when you don’t listen to me you get punished. I know you secretly like getting spanked, even if it is humiliating to you, but don’t make a habit out of it girly! So get your girly butt in gear and take off the towel honey! We gotta get you in your lingerie! You loooooveee wearing lingerie!”

Ashley’s rattled brain took in the new information like a sponge. Disobeying Paige meant getting punished. He liked being spanked but was embarrassed about it. And he also liked, no loved, wearing lingerie. Ashley blushed taking in the information as he grabbed the white lace and silk panties. They looked so small in his hands. So different than the boxer briefs he’d been wearing before. Would they feel different?

Ashley took off the towel, letting it pool at his feet as he stood naked in front of Paige. He lifted one leg then the other stepping into the white lace and ruffles of the panties, sliding them up his smooth legs. The sensual feeling of the silk sliding up his hairless thighs, combined with the implanted thought of loving lingerie, made his small dick twitch. As the panties settled into place over his hips, his dick made a small but noticeable bulge in the front. The lace cutouts showed off his hip bones, where the white peplum ruffle gave a cutesy feel to the slutty panties. The panties were small, not quite full cut in the back so that half his cheeks were showing. White ruffles on the backside looked especially girly on his butt.

Paige clapped and giggled as she took more pictures in his panties, making sure to capture that he was hard in them. She handed him the frilly lacy bra next. He struggled with the clasp behind his back until Paige showed up to snap it in front of him before rotating it around his body. She helped him scoop up the small amount of baby fat on his chest to get on top of the push up padding, giving him a noticeable B cup chest with cleavage. The pink bow nestled between the lacy white cups made it even more feminine than the bra already was. And the white ruffles on the bra straps added to the cuteness of the girly bra.

Ashley slid on the white thigh high socks with the little pink bows on the top dressed in all white lingerie, he stood and looked at Paige for something. Approval? Direction? He wasn’t sure. But he knew that he wanted her approval and that his body loved the feeling of his lingerie. He could see how his dick was bulging out of the panties, well as much as it could due to its size, and he felt that warm fuzzy feeling in his stomach.

Paige laughed and smiled at the sissy in front of her. She had him pose a few times, hand clasped above his hard dick encased in white silk, knees together with his toes pointing inward and pouting to the camera. His arms pressed inward deepening his faux cleavage. Paige was delighted with her obedient former bully. Even if he came out of it, she already had enough on him to get him back 10x for what he did to her. But she wanted more.

“Oh that’s just precious, sissy Ashley! You look so happy in your little white lingerie!! But I’m sure you’re embarrassed about your *ahem* little problem” glancing down at the small bulge in his panties.

Ashley looked and immediately felt ashamed at the bulge. Paige said he was embarrassed about his size and had warned him about getting hard earlier in the tub.

“I’m sorry, Paige! But I just love this lingerie so much I can’t help it!” He hid his face in his hand while trying to cover up the front of his panties with the other.

“Oh it’s ok sissy! I know you can’t help it. Here, I think we can take care of it temporarily until we can get you something more… permanent for your unsightly lady front.” Paige dug through some drawers until she found some medical tape.

Pulling down Ashley’s panties, Paige giggled again at the small but swollen member poking out, which only made Ashley blush harder while getting harder! Thankfully, Ashley grabbed the ice pack again and shrunk down his package to minuscule size once again.

“I learned this from drag race, you could learn a lot from those queens, Ashley! We’ll watch some later you’ll love it.”

Paige pushed Ashley’s balls up into their cavities before tucking Ashley’s dicklet between his legs. With some strategic taping, she was able to make a flat front. The panties were pulled back up and Ashley saw a fully flat front, no sign of bulge whatsoever!

“Wow, that’s wild, Paige!” Ashley exclaimed while examining his feminine form.

“Yeah I know it’s crazy. Even with how small you are, it would have been unsightly having that poking out *giggle*”

Hearing her making fun of him, especially kneeling between his legs with a look down her shirt at her C cups made Ashley’s dick try to get hard again. Ashley groaned from discomfort as it tried to get larger but the tape held strong.

“Oh did the little princess try to get hard again?? Well, beauty is pain sometimes honey! You’ll get used to it. Let’s get your hair and make up done first before we finish with your dress. Ooooo but you need to get used to your new shoes first!” Paige bounced over to the heels. The 4 inch tall Mary Jane patent leather pumps gleamed on their shiny surface. There was a small platform under the rounded toe so it wouldn’t be so hard to wear them, but the pointed stiletto heel would make things difficult. The black ankle strap would help to provide some support as well.

Ashley stepped carefully into the shoes, holding onto Paige for balance. She buckled him in tightly to the heel before stepping over to the vanity.

“Alright Ashley, let’s see your best sissy walk!”

Ashley nodded his head, trying to quell the small voice inside him screaming indecipherably something at him as he took his first steps. He wobbled quite a bit, arms held straight out as he tried to maneuver in the stilt like shoes. He took about 5 steps before landing flat on his pantied butt.

“*giggle* aww nice try Ashley, seems like you’ll need some work. Now stand up and try again. Remember, shoulders back and chest forward, butt arched out. The heels should help with your butt. Keep your elbows tight to your side with your hands out and wrists turned. Small steps for now, one foot in front of the other and make sure your hips roll side to side to show off that butt.”

Ashley nodded and stood back up carefully. Pushing his chest and butt out, wrists turned and elbows at his side, he took small mincing steps. The smaller steps were much easier this time but he still faltered right before reaching Paige, who was filming the whole scene “so we can watch it back afterwards for tips!” She said.

“Hmm wobbled again. And not enough wiggle in that butt. I know you’re a glutton for punishment from me but I feel like you’re asking for it.” She said before spanking his butt, harder this time than the first punishment. A wave of warm pleasure filled him the same amount as the pain from the spanking as he moaned slightly from the punishment.

Ashley walked up and down the room several times, getting girlier and sissier with each attempt. Paige was loving it, seeing the machismo bully prancing around her room in 4 inch heels and frilly white lingerie. She was especially loving every time she got to spank his pantied butt for a mistake, making him blush and moan with each swift stroke.

“You’re getting better, sweetie, but there’s still not enough wiggle in that butt. Hmmmm, here I think I know just the trick! A…. Training aid. Yeah we can call it that.” Paige was about to test the limits of Ashley’s addled brain, but it was worth the risk. Plus, if he came to, there was more than enough **** to ruin him.

Ashley reached into her nightstand, hiding underneath some magazines she found a “gift” from an old boyfriend. Something she told him she’d never wear that hung around with her other toys. A small metal butt plug, a couple inches long and only about an inch in diameter. The pink jeweled base was the added touch to the slutty toy.

Ashley looked uneasily at the shiny plug. “Wh-what is that Paige?” He asked nervously.

“It’s just a training aid, princess. It will add some wiggle to that walk. Now just grab the back of the chair and bend over for Miss Paige ok?”

Ashley nodded and minced carefully over to the chair, bending over at the waist so his pantied covered butt was pushed out. His conscious mind wasn’t sure what was happening, but that little voice was louder than ever making him nervous. But the calming touch of his best friend on his back and the shushing sounds calmed him down.

“Paige knows what’s best for me, she told me to listen to her. And I want to make her happy. Be a good sissy princess for Miss Paige” Ashley told himself.

He sucked in his breath as he felt the cold lubricated tip of the plug at his entrance. He got worried again feeling it as his little voice railed and screamed inside of him.

“M-Miss Paige I’m not so surrrrrrreeee-UUUUNNNGHHHHH!!” Ashley started to protest before Paige pushed in, spreading his sphincter with the metal plug. The plug slipped in past the roundest point and settled in around the narrow base. The immediate pain was gone almost as quickly as it arrived. All that was left was a fullness inside of him, and a dull pleasure as well. He could feel his dick trying to swell in the tape but still remained imprisoned.

“That’s a good girl, princess! See, that wasn’t so bad! Now, let’s see you walk now” and with another slap on his butt, pressing the plug even deeper inside him eliciting a girly groan Ashley slowly stood up from his bent over position. He could feel the plug move with him, rubbing up against something inside of him that sent small jolts of pleasure into his groin.

Blushing from pleasure and humiliation, Ashley rolled his shoulders back and walked. His hips undulated side to side seemingly on their own from the fullness inside of him. His steps got a bit longer as he no longer had to think about what to do and could concentrate on walking. He minced from one side of the room to the other, like a sissy princess with her arms and hands out to her sides. His heels stepping one foot in front of the other, their spiked heel making a staccato on the wood floor.

“Good job Ash!!! Best one yet! I think you’re getting the hang of it! Oh yay that makes me so happy”

Ashley beamed with pride that his actions had made his friend happy! A happy warmth went over his body hearing her elation. He was determined now to get that same reaction as much as possible going forward.

Paige had Ashley sit down on the cushioned lilac and white stool in front of her vanity. He sat gingerly, but still felt every inch of the plug pushing deeper inside him. But he was determined to do well as a sissy so he sat on the edge of the seat, pushing the plug further inside him, back straight with shoulders back and his legs crossed over the other, squishing his tucked dick even more. “Beauty is pain” Ashley recited to himself.

Ashley looked at himself in the mirror, his head and torso on display. His hair was still in the towel turban on top of his head. His face, freshly shaved and moisturized, was gleaming and healthy showing off his pretty boy face that still had some puppy fat on his cheeks. His chest was covered in his frilly white lacy bra. His torso was gleaming from the moisturizer, giving his cleavage even more definition and emphasis. Even though his faux breasts were small, they were definitely noticeable, especially with the push up effect.

Paige’s shining face popped up next to his, smiling her big smile at him through the mirror. “You ready to get beautiful, princess?”

Ashley looked into his eyes, seeing turmoil inside them. But Paige’s smiling gorgeous face quelled that turmoil in a moment.

“Of course, Miss Paige! Make me beautiful please!” He happily squealed as his inner voice railed and screamed.