Masculinity Lost Ch. 22

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Dani learns how to please on his date with Demarcus.
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Part 11 of the 17 part series

Updated 04/26/2024
Created 02/03/2024
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Chapter 22: Some date "practice" before getting dressed

Danny and Candi walked hand in hand back into the back room of the salon where they found the three girls laughing away while a Dua song played in the background. "Well, I guess not technically three girls with Jamie, but close enough" Danny thought.

Candi stopped Danny right before the door, turning him to face her. She bit her lip as she searched for exactly what to say. "Listen, I know this really sucks for you and I'm sure your mind is going a mile a minute trying to figure it all out, but I'm... I'm happy you're here. Not happy you have to go through this like I did, cause it's been a nightmare. But happy that I finally have someone that can understand. Someone forced into skirts and heels and tits and... and... everything! I just wanted you to know that you have... a friend, ok?"

Danny wasn't expecting this reaction. Everyone he'd met so far as Danielle has wanted to torment him, or get in his panties (pants! Damnit Danny don't give in man!). He realized that Jessica and Jamie weren't going to let him go anytime soon, even though he'd try as quickly as possible to get out of their acrylic claws. So if he was stuck like this, it was good that Candi.... Cameron could commiserate with him.

"Th-thank you.... Candi. I'd like to be friends," Danny said with a weak smile and squeezed Candi's hand in his own.

Candi and Danny opened the door. The girls had clearly gotten into the wine quite a bit as there were a couple empty bottles on the table. Jessica was sitting in Danny's salon chair with both legs tucked under her and her heels off her feet sitting on the floor. She was laughing good heartedly while looking at Jamie and Stacy, a flush on her face.

Danny was surprised to see Jamie and Stacy on the couch sitting very close together. Well, more exactly Jamie was basically sitting on Stacy's lap. Jamies legs were draped over Stacy's while Stacy had an arm around Jamie while playing with Jamie's long blonde hair. Jamie was giggling like a love struck girl, looking up through his long lashes, with a blush across his cheeks that didn't seem all from the alcohol, as the tall voluptuous red head while Stacy was grinning like Cheshire Cat down at Jamie.

As the three girls heard the dual click clack of Danny and Candi's heels on the tile floor, they all looked up at the two feminized sissies standing at the door way. The giggles and laughs quieted immediately. Stacy turned her grin to the slutty looking boys and it widened at the sight of Danny in his tiny little bikini, a twinkle in her eye as she shifted in her seat, tightening her thighs together in her black wet look leggings.

Jessica swung her feet out from under her and stepped back into her strappy heels, a similar grin on her face seeing her ex boyfriend looking like a stripper working to pay off her new tits. She couldn't believe how far he'd come in just a day and couldn't wait to push the womanizing bastard even further.

While Jessica seeing him like this was mortifying enough, having the guy he bullied for years seeing him in this tiny pink bikini with DD tits and heels with a fresh spray tan made him want to die. Jamie sprung to her feet with a squeal of glee as she rushed over to Danny clapping. She stopped short when she saw the two sissies holding hands. His own hands flew to his mouth and another squeal came out of his mouth.

"Oh. Em. GEEEE!!! This is sooooo cuuuuttteee!! You have a sissy bestie!!! Here I thought I could be that, but I guess after seeing and tasting my big girl cock I'm a little too dominant to be your beta best friend. I get it honey, you need someone your.... Size hehehe" Jamie drunkenly gushed over the two feminized boys as they blushed at what he was implying. They immediately dropped holding hands but Jamie grabbed them both and forced them to hold hands again, interlocking fingers this time.

"Nuh uh! Don't be shy now! We already know you're best GURL-friends. You're gunna hold hands until *hiccup* we tell you to stop" Jamie sternly told them.

Danny and Candi blushed, both embarrassed by the relatively intimate act of holding hands, especially in front of these girls. Both looked down at their heeled feet before feeling the other squeeze their hand in support.

Jamie, oblivious to their reaction, stepped in front of Danny. Eyes slightly glazed over, he stared at Danny's new tits with lust before cupping them in his small hands. "Omg they're gorgeous! This is the best work you've done, Stacy! Even better than mine before I went on that vacation with that sugar daddy! For an older guy, he really knew how to play with these puppies. I know I really liked it when he did this"

Jamie roughly groped and squeezed Danny's left tit while gently rubbing his thumb over the right nipple through his tiny pink bikini top.

Danny's nipple sent pleasure throughout his body as he bit his lip to stifle a moan. Danny clenched his thighs together involuntarily as the pleasure coursed through him. "Omg that's only brushing the nipple! What else is gunna happen when it goes farther than this??"

"Oh the little sissy likes it!" Jamie teased. "Remember in high school when you found that bikini in the locker room? You and your buddies thought it would be hilarious to have the sissy wear it 'cause that's what he really wants'? How you forced me down and stripped me and put me in that tiny bikini? How you spanked me and slapped my 'tits' in my bikini? You wanna know something, Danny? That was one of the hottest things to happen to me in my life. And I think you're like me, loving this as much as I did" Danny groaned in response, unable to deny it like he wanted to cause it felt so damn good.

"Well you'll really like this then, I know I did." Jamie pulled the tiny triangle from his boob, revealing the tan lines. Jamie laughed with glee at the sexy tan line before dipping his face down to his nipple. He looked up into Danny's eyes as his tongue flicked across the stiffened nipple. Danny gasped with pleasure, eyes locked with his former victim as he wrapped his lips around the nipple while viciously manhandling his tits.

He sucked and teased the tip with his tongue, lathering around and around. Danny was lost in ecstasy, gripping onto Candi's hand for dear life as his knees buckled. A wet spot formed in the tiny triangle of his bikini bottom as his ass involuntarily clenched and tried to suck in his plug. Danny let out a girly moan as his other hand grabbed Jamie's shoulder for stability before pulling him in tighter for an embrace.

Danny was on the tip of a massive orgasm before he heard a loud clap from Stacy. "Enough, Jasmine. You've had your fun with your bully. You'll be able to play with her again soon enough. You almost made her make a mess in her cute little bikini. The number one rule for sissies is to keep them on the edge, both mentally and physically. Remember that, girl."

Jamie reluctantly backed away from the quivering mess of his bully. "Yes Miss. I'll try to remember in the future" Jamie said as he licked his lips, looking her former bully up and down like a piece of meat. Danny saw him adjust the crotch of her tiny Jean shorts as she backed away and Danny nervously licked his lips and shuddered at the thought of that monster in his daisy dukes.

Jamie of course saw this tanned beach babe lick her pink lips staring at his crotch. "The whole blackmail thing was a ruse like Jessica said. Look at him eye fucking me wanting my cock again. Gawwwddd I cannot wait to get his pretty lips on my cock again. I've been dreaming of this since high school. I'm gunna make him my little bitch" Jamie thought to himself.

Jessica motioned to the sissified boy to come to her. Danny walked across the room, still holding tightly to Candi's hand. His butt jiggling with each step in his high heeled slippers. But even worse, his new boobs bounced up and down as his new bikini did practically nothing to support them.

Jessica grabbed a handful of Danny generous DDs and giggled herself. "Gosh Dani, you've really changed in the last 24 hours! You're a knockout honey! And to think just yesterday I wanted to get back together with 'Danny', my masculine alpha ex boyfriend. I don't think that's right anymore, is it? A boyfriend wouldn't have tits like these right?" Jessica squeeze his melons while grazing his nipples, causing Danny to lightly moan and squirm.

"Hahaha that's right, a good girl likes her titties played with. A boy wouldn't. A boyfriend wouldn't be wearing such a tiny little bikini. Look at these tan lines! A little slutty, I think, but I think it works for the new you. Demarcus likes his girls a little slutty. Well, a lot slutty I should say hahaha. This little tanned heart is soooooo cute! And did you like my choice for the playboy bunny? Thought it was fitting for your Halloween costume hahaha I'm sure the boys are gunna love it just as much as I do!" Jessica gave Danny's butt a slap right on the playboy bunny tan lines, making him yelp and his butt jiggle.

Jessica looked down at your feet with a quizzical look. "I didn't order you or Candi to put on heels. Why'd you choose to wear them, Danielle?"

Danny stammered, not wanting to let his ex know his feet hurt from not being arched in heels. It was humiliating enough knowing it himself, and Candi already knew too. He didn't want to give Jessica any more ammo. "I- uh... um..." Danny stumbled.

"Did you choose to put them on yourself?? Omg that's so precious! You're thinking so much like a girl already that you're matching your shoes to your outfit! And killer choice honey! You look like you'd break some necks at a pool party. Heels are definitely a permanent part of your wardrobe from now on. They really make that ass POP!"

Danny realized that Jessica thinking he chose them himself was way worse! Now she thought she really was breaking him into becoming this slutty bimbo! Before he could correct her, Jessica placed her hand on Danny's thong covered butt and pressed a single finger on Danny's plug. Danny's protest died in his throat as a moan escaped instead.

"Goooood girl. This is what you get when you make the right decisions. Pleasure instead of pain." Jessica pressed a little harder, pushing the plug against Danny's prostate and making his clit throb in his cage. Danny was already incredibly worked up from his new tits being mauled by Jamie. He didn't think he could be more horny. His lips parted and he panted like a bitch and Jessica alternated pressing and releasing the plug in Danny's butt. Candi held Danny's hand tight, knowing exactly what the poor boy was going through.

Jessica removed her hand from Danny's ass and Danny was left panting for air. "Now that you know what the carrot brings, as well as the stick, it's time to get to training for your date. As slutty as you look, you're woefully unprepared for making sure your new 'Daddy' is taken care of and warmed up."

"So first, let's make sure you know how to walk like a good slut. The plug and heels have helped, but your new tits will need some getting used to. So you're gunna walk across the room until we get your sashay right. Candi, let go of your sissy friends hand for now and stand in the corner. And get us more wine too, girl. Hop to it, slut!" Jessica spanked his ass, eliciting another yelp from Danny and causing him to take a few nervous steps.

Jessica sat down with the other two girls, Stacy and Jamie cuddling on the couch with more Prosecco, while Candi stood in the corner with a bottle at the ready.

Danny recovered from his stumble and nervously took a few steps in his heeled sandals. He realized these sandals would be more difficult without the ankle strap support so he needed to be careful.

Danny minced carefully but clumsily across the room. While he was used to wearing heels, the lack of support was difficult. And combined with the new weight on his chest he was top heavy and felt like he was gunna fall over at any moment. Plus, the tits had no support from the flimsy bikini top, so the bounced and jiggled with every movement. Danny carefully turned around and minced back, with a lot of laughter and taunts from the now drunk women (mostly women) watching him.

"Hahaha omg I remember my first time in heels and I was better than this! Come on, Danielle, really strut your stuff! Make the big ass wiggle for the boys! Hahahaha" Jamie teased.

"Oh no, honey that just won't do! What happened to my slutty ex boyfriend who strutted across campus last night? Roll your hips and straighten your shoulders! You got those puppies on you, show them off baby!!! Hahahaha" Jessica jeered laughing away.

Jessica leaned towards Jamie and fake whispered loud enough for Danny to hear. "This was the alpha male bully you told me about from high school?? Are you sure? Cause... just look at HER! There isn't an ounce of alpha male left. He barely even makes a bulge in that tiny bikini bottom! Youre like twice the 'size' of him! You easily could have taken him down in high school honey"

Danny's eyes started tearing up from the taunts. One from a sissy who he owned just a few years ago who wouldn't dare make fun of him. Now Jamie was laughing away as Danny's titties bounced along with his big butt. And then his ex girlfriend who used to adore him and make him feel like the alpha male he wanted to be. Now she was laughing at him in his tiny bikini as he minced in his high heels.

But what made it worse was that his cock was as hard as it had ever been. Or would be if it wasn't for this damned cage. Every taunt and jeer and laugh only made his cock throb more in its prison. A large wet spot got bigger by the moment on the front of his thong. "What the fuck is wrong with me? Why am I so turned on by them making fun of me??" Danny thought.

The only one who made it slightly better was Candi. Danny looked at her eyes and she gave a small sympathetic smile. He saw her mouth "just do it, it will only get worse."

Danny tried again with a little bit more effort but couldn't get his heart in it. As he turned around and started back across the room, Stacy stood up and walked to him.

"Absolutely not, sissy. You need to put the effort in to look sexy and desirable. Don't worry, I'll make sure you remember." Stacy grabbed him by his new blonder hair and bent him at the waist. Five hard smacks on his right butt cheek one after the other had tears in his eyes. Another five on his left had him openly crying. Five more on the right, Danny was sobbing and begging for Stacy to stop. Another five on his right and Danny couldn't take it anymore.

"Miss-misstress pleeeaseee! Please stop!" Danny sobbed.

"Hmmm I don't know. Will you be a good girl for us?" Stacy coldly stared down at the sobbing sissy.

"Yesss Mistress!"

"Say it then. And make us believe it"

Danny got down on his knees with his hands clasped in front of him, pushing his tits together. "Mistress I'll be a good girl! I'll walk like a sexy girl! I'll wear whatever you want! I'll be the p-prettiest sexiest g-girl for you!"

Stacy tutted "that's right. Now try it again, slut"

Danny hated it but knew he couldn't take anymore spankings. So he stood up, pulled back his shoulders presenting his new DDs out proudly. He kept his upper arms tight at his side, forearms out to his side with wrists limp and turned out. He walked a tight rope, one heel in front of the other, wiggling his ass and rolling it side to side. His new tits jiggled up and down and side to side with each step and Danny let them bounce provocatively. Each roll of his hips made his muscular and fat booty jiggle. He turned on his heel at the end of the room like a model and strutted back while the girls wolf whistled and yelled "get it girl! Get those dicks hard baby! Woooooo!"

Danny was made to walk 10 more times perfectly. Stacy made sure each mess up he had was quickly and sternly corrected with a slap on his now pink behind.

Finally, the girls had him stop and stand in front of the seated trio.

Jessica spoke to him "so you can walk like a girl proud of her body, but you need to make sure your man fully appreciates it. And since you're dressed like a stripper, I think a lap dance is in order. And who better to give a lap dance to than your former victim. If you can't make Jamie hard well... I think you know your punishment sissy" Jessica held up her hand letting him know.

Danny gulped and nodded his head, his loose curls bobbing up and down. Stacy pulled out her phone and turned on some hip hop over the speakers. Jessica pulled out her phone and started recording.

"Ok, Danielle. You said you wanted some practice and tips for your date with Demarcus tonight and Jamie volunteered to fill in. While Jamie is no where near the masculine presence Demarcus is, I'm sure SHE will appreciate it just like Demarcus will. Now get to dancing, slut!" Jessica ordered.

Danny immediately starting moving his hips to the music. While a bit inexperienced, Danny made up for it with his new found eagerness to perform. While he'd never given a lap dance before, he'd received a lot at strip clubs partying with his buddies. Even getting one from Jessica herself where she stripped out of a nurses uniform on Halloween down to just her thigh highs and heels before they had a wild night of sex. So he knew somewhat of what he should do.

Danny's hips swayed back and forth as he slid his hands up and down his body sliding up his tanned stomach up to cup his new boobs. Danny turned around presenting his tanned butt to Jamie's face as he slowly bent at the waist, sliding his hands down his smooth legs. The thong disappeared between Danny's big cheeks but the pink jeweled plug was front and center, shining in the light. Danny slowly stood back up, running his hands up the back of his legs before cupping his butt cheeks in both hands and making it bounce and clap to the music.

Jamie was entranced by the rolling curves and movements of his former bully. The wine had definitely gotten to him and he was thoroughly drunk. He watched as he jiggled his big plump ass in his face and thought back to high school. The conflicting feelings of hating how Danny bullied him for being a sissy while at the same time loving and craving the humiliation. And also how damn cute he was, mix of pretty boy and "alpha" and how he wanted Danny to really give it to him.

But now, looking at this Uber feminine creature swaying in front of him, putting in so much effort to turn him on, that it further cemented the thought that Danny really was a sissy the whole time. How Danny bullied him because he was repressing those same feelings Danny had. Wanting to be feminine and sexy and desired. But also wanting to be owned and used and humiliated. And Jamie was gunna make sure Danny got what he wanted.

Jamie reached out his manicured hands and grabbed Danny's tiny waist. His 1/2 inch long powder blue acrylics dug into the soft flesh and pulled Danny into Jamie's lap. With a yelp of surprise, Danny fell flat onto Jamie's lap, pushing the plug in at the same time. With a soft moan, Danny was lost in the worked up horniness of the day as well as the wine he had drank early. The feelings of pleasure, combined with the fear of punishment and the humiliation of it all, got Danny to slowly work his butt back and forth running along Jamie's crotch. Jamie must have adjusted himself from his tuck cause Danny felt the big beast half hard from his ministrations, and getting harder by the second.

Danny's enthusiastic wiggling on Jamie's lap spurred on the femboy even more. He started thrusting into Danny's plump cheeks, sliding his hard cock in between the two cheeks. Danny's whimpers at the feeling turned to moans feeling the plug being moved around in his butt.

"Oh that's a good girl, Danielle! Yeah you're doing such a good job girlie. Demarcus is gunna love this" Jamie teased as a hand snaked its way up to Danny's tits and started caressing roughly through the bikini top. Danny's moans got louder as the electrodes stimulated his own nipples causing him to arch his head back and press his body into Jamie's.

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