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Chapter 25
by
Cdslavejessie
Where do Demarcus and Danny go on their date?
Drive to Demarcus’s place, meeting Demarcus
Jessica, Jamie, and Danny drove in Jessica’s expensive white BMW, cruising through the city back towards campus. It was a warm almost summer night with the sun starting to go down at 7 PM as the girls sang and danced to a girly pop song with the windows rolled down. Well, the two girls, or close enough, in the front were singing and dancing. Jessica and Jamie were vibing away to Olivia Rodrigo while Danny sat glumly in the back seat, alone with his thoughts.
Danny struggled with the seatbelt across his much bigger chest for what seemed like the 100th time this drive. Under his boobs, on the other side, in between them, all just seemed to draw more attention to his unwanted chest. Danny settled with it between the two mounds while he pondered what had happened today.
Danny was trying to come to grips with what had happened back at the salon. The clothes, make up, and hair could all be changed easily enough. The tits could be taken off. Hell even the piercings and tan would heal and fade with time. Danny could accept those facts by looking at the future, where his clothes wouldn’t be tight and silky and lacy and he could go back to being a guy again. But what was bothering him was something he couldn’t change. He was now a cocksucker. Forever. No amount of time or cleansing showers or having sex with real girls would change the fact that he had sucked a cock, a big cock, to completion. And he’d done it willingly. Of course there was the threat of **** and spankings and further modifications that started him to take the cock in his mouth. But once he had it in his mouth, he had willingly bobbed up and down trying to get Jasmine to cum. At first his enthusiasm was just for fear of punishment, but after awhile he….. he had wanted to make it spurt. It was like a challenge to him. And in his horny haze, it felt…. Good? Of course the mouth on his caged dick felt good, as did having his plugged played with but those could be explained. When Jasmine had shoved her cock in his throat and he felt it stretched and leaving him breathless, he’d never been hornier in his life. Having something so…. Powerful inside him and it was his job to give it pleasure he found was pleasurable in itself.
But now looking back at it he was horrified by his actions. He remembered the feeling of his hair being gripped tightly and his mouth used. Having no control felt…. Freeing? Just giving up in that moment and going along for the ride and riding the wave was a wildly new feeling for him. And it scared him to no end. How he wanted to be controlled again and feel that pleasure went against every straight thought in his 21 years of life. Danny’s heterosexuality was rattled to its core.
Danny looked at Jamie in the front seat, dancing like any other girl and looking very…. Cute, and all Danny could think about was the python trapped between his thighs. As he stared at her lap, Jamie turned around and saw him staring at his crotch. Jamie grinned happy that his former bully now seemed fixated on his cock.
“Earth to Dani! I know you had your first taste and can’t get my dick off your brain but you look like you just saw a ghost! Smile honey and be a good girl! If you don’t cheer up, I’ll climb back there with you and fuck a smile back onto your face” Jamie teased.
Danny eyes snapped up to Jamie’s and had a horrified look on his face. “No no no! Not again! I-I can’t! I’ll be a good girl Jamie!” Danny **** a cheery smile on his face but it looked as **** as it was.
“Jamie! Maybe a little too crude for our little sissy girl. I’m sure she’d love for you to come back there but with her makeup freshly done I’m sure she doesn’t want you to ruin it again before her date. Here, Dani I know you’re nervous for Demarcus but you shouldn’t be he’s gunna love you. Take this and take a few hits. It’ll make you much more relaxed sweetie” Jessica handed back her THC pen and Danny took it in his pink nailed fingers. Wanting to stop the intrusive thoughts, Danny took a bunch of big hits, filling the backseat with vapor. Danny relaxed back into the seat as the weed hit him on the drive back.
His hands stroked over his smooth legs, feeling the silky nylon caressing his skin. “If there’s one thing that’s good about all this is the feeling of my smooth legs. When I get back to being a guy, I think I’ll keep them shaved. A lot of guys shave their legs so it won’t be that weird, right?” Danny thought as he rubbed his thighs together, making his dick twitch in its prison.
The drive continued on as the girls continued singing their hearts out in the front while Danny puffed away in the back. After awhile, Danny loosened up enjoying the girly pop. Realizing in this situation he wouldn’t have to hide his love for girly pop songs, he soon was singing away with the other girls to T-Swift. The girls at first shared a glance when Danny started singing along, but then giggled and joined right in with the feminized boy. Danny lost himself in the music, just enjoying the high and embracing belting out the lyrics society said a man shouldn’t enjoy.
“I’m glad you’re embracing your girly side Danielle! I know Danny secretly enjoyed this music, now you can be open with it, just like all the other girly things you’ve been hiding. Aren’t you glad you finally came out to me as a sissy girl?” Jessica asked as she gave Danny a hard look in the mirror.
At the moment, Danny felt so good from the weed and music, as well as the sensual feelings of his legs rubbing together, that he did feel happy. He smiled back at the mirror “Yes Miss Jessica. I am happy”
“That wasn’t what I asked Dani”
“Yes, I am happy I came out to you as… a… sisssssyy! Oh gawd! That felt good!” Danny said, losing his train of thought as they hit a bump in the road, pushing his plug into him again. Jessica and Jamie grinned and giggled, thinking Danny said it felt good to say it out loud.
“Good girl! Now we’re a few minutes away, I made you a few new social medias while you were getting pampered. Just insta and snap and added a few friends to them and followed some profiles I think you’d like. Why don’t you send your Daddy a selfie on snap? Gotta tease your new look to really get him going.”
Danny had completely forgotten about his phone as he opened up his purse and unlocked it for the first time today. There were some notifications and texts from friends about the party on Friday, but nothing major. He did see he had a new email set up that had subscribed to a bunch of feminine stores filled with promotions and sales for beauty products, heels, lingerie, dresses, work out clothes, the works. None of the brands were “modest” and all were leaning towards flirty girls who liked to show off.
Opening up insta, he saw that he now had two profiles, one for Danny Stewart, the other for Danielle Bennett with the handle @DaniBambi. He only had one post, one of the outfit he walked home in last night that Jessica must have taken with the caption “Time to break free”. He looked at who he followed and there was Jessica and Jamie as well as Stacy and the page for New You Salon.
He saw he was tagged in their latest post, a shot from the neck up showing off his new balayage cut and freshly done make up with the caption “Danielle came in nervous as a baby deer but by the time we were done with her she was a whole new woman!” Danny was sure that caption was done on purpose hinting at his transformation. He was shocked that he had been posted on social media, worried that people would see through all the make up, but all the comments were just complimenting her and Stacy on how incredible she looked. Danny was relieved but also worried that no one could tell he was a man, taking another chip at his eroding masculinity.
Danny saw that he followed Demarcus as well and saw he had already commented on his post “Looking GOOD girl!” And just below that was Josh, the guy from the gym commenting “Daaammmnnn!!” With a bunch of heart eyed emojis.
Unable to handle the shameless flirting from guys over his own image, Danny switched to snap chat and saw he had a new profile there as well, with a message from “D-ruckus18”. He opened it up and saw a selfie of Demarcus shirtless at the basketball court. Sweat was dripping down his face and down his torso, accentuating his big black muscles. His pecs were so defined and there must be at least 10 super defined abs on his stomach. It was captioned “Just finished at the gym. Can’t wait for tonight babygirl”
Danny looked at this epitome of masculine physique and was jealous. Jealous Demarcus was able to look so masculine while Danny was stuck as a girly girl. Surprisingly, looking at the toned muscles, Danny felt a slight twitch in his cage. “It must be the weed! Not looking at Demarcus!” Danny consoled himself, only half believing it.
Jamie leaned into the back seat and saw the ebony stud on Danny’s phone. “OH. MY. GAWD!!!! He is a fucking BODY girl! Ooooo I know exactly what to do. Give me your phone. Were gunna send him a video of you!”
Danny thought about holding onto his phone but the look on Jamie’s eyes made him give it up with a sigh. Jamie grabbed the aux and put on a Selena Gomez song.
“Ok girlie, now we know you love girly pop and we know you know this song. So just listen to the music and vibe with it. Feel your girly body and embrace it honey!”
Danny thanked god for the potent weed he smoked as it calmed his nerves. Danny closed his eyes and listened to the music, swaying back and forth in his seat.
*cause I just wanna look good for ya, good for ya* lyrics bumped through the car as Danny lip synced along, moving his shoulders and hips along with the song.
*gonna wear that dress you like, skin tight* Danny slid his hands down along the sides of his breasts, down his stomach, down to his short skirted thighs.
*gonna do my hair up, real nice* Danny moves his hands up to his hair, running his fingers through the soft curls.
*I just wanna look good for ya, good for ya*
Danny leaned towards the camera, arms tight to his breasts pushing them together in his pink top, finishing the lyric. He parted his lips and in his high haze his eyes looked lustful. Enjoying the high and the girly music he leaned back with a big smile and broke out into a fit of giggles.
Danny opened his eyes to the girls Wooooooo-ing in the front. “Danielle that was fucking HOT! I want to jump back there and put those pretty lips to use again!” Jamie gushed.
“Not now Jamie, can’t be messing up our new girlies make up. Be a good girl and sit in the front” Jessica ordered with a smile on her face. She had always been friends with Jamie and knew of his…. Proclivities. But they really bonded over Danny and feminizing him. Jessica now knew what was so hot about feminizing boys that Jamie loved so much, and relished her new role as Domme, which Jamie also loved. Jamie gave a small smile in return and said “yes Miss. I’ll be a good girl *giggle*” but shot Danny another look of hunger, slightly adjusting her jean shorts.
Danny was still lost in his giggles but saw Jamie adjust her shorts. His giggles slowly subsided but his smile remained as he stared at Jamie’s crotch where a bulge was forming. But as Jamie tapped away on his phone and sent the video, he realized he just slutty danced for his roommate! He told him he dressed like this for him!
Before Danny could calm down from his realization, they pulled into his apartment parking lot. Jamie and Jessica turned around to give a talking to their sissy girl.
“Ok Danielle. It’s time. I talked to Demarcus earlier on your snap and let him know how eager you are to please your Daddy hahaha. After your practice today, I’m sure you’ll have no problem making sure daddy’s happy. But if I hear otherwise, Miss Stacy and I will make sure your ass pays the price. She’d love to permanently lock up little dani like she talked about. We’ll know if you’re not a ditzy bimbo btw, Jamie and I will be watching from afar.”Jessica gave her orders to Danny who fearfully remembered the look Stacy gave him while threatening him with a permanent chastity cage.
“You’re a little early but I know you’re eager for a date with that stud so wiggle your little butt up there sweet cheeks.”
The trio stepped out of the car into the parking lot. Danny, still not used to the short skirt, gave a full view up his leather skirt as he swung his legs out. With how tight it was on his thighs, he couldn’t put one leg out first. Jamie gave a good laugh about the upskirt moment causing Danny to blush.
The girls had him pose in the parking lot, taking numerous pictures of him in his hot new outfit. Danny was made to bend forward at the waist with his hands on his knees giving a full view down his little top as he blew a kiss to the camera. But the one of Danny standing with his butt to the camera looking over his shoulder with eyes partly closed to show off his new lashes and pretty eye shadow really got the girls going. His pink shiny stilletos stuck out Dannys butt and made his legs look so toned in his stockings. And the little bows on the heel looked “sooooooo CUTE!” As Jessica pointed out. Dannys big butt strained the leather skirt, and with how low it was and getting out of the car, the sides of his pink thong were showing out of the waistband.
Finally they were done and as Jessica tapped away on her phone, Danny tried to turn to walk away. But Jamie grabbed his hand and spun the high heeled sissy towards him. Before he could react, Jamie’s lips met his with dominant ****. Prying open his lips with his tongue, Jamie forcefully made out with the sissy. After a few seconds, the **** filled brain made Danny forget who he was kissing and he started kissing back. Tasting Jamie’s lipstick and feeling his soft skin, he could pretend he was making out with a girl for once.
Just as quickly as it started, Jamie pulled away and slapped him on his leather covered butt, causing a ripple across his ass. “Mmmmm that’s right sissy girl. That lip stain is perfect, not even a smudge. But touch up your lip gloss before you see Demarcus. Go make daddy happy. And, make sure you record it. I want to see you take your first BBC sissy bitch. If you do, I’ll make sure you feel reeaaaalll good later” Jamie whispered as she felt up Danny’s butt and pressed on his plug, eliciting another soft moan from Danny. “If you don’t, there will be punishment” Jamie reached under Danny’s skirt and squeezed his balls. The squeezing, combined with being so worked up and backed up, made the pain so intense that Danny’s knees faltered making him grab onto Jamie’s shoulders for support.
With a final spank, Danny was sent on his way, fishing out his lip gloss from his purse and applying it. Taking one last puff of his vape to calm his nerves, Danny shouldered his purse (his purse??? What happened to me??) elbows tight to his side, wrists turned out, and strutted into his apartment building.
Danny pressed his finger for the up button on the elevator, not trusting himself in these stilts to navigate the stairs. He was annoyed that he couldn’t press the button normally because of the glued on pink fingernail. Danny held out his hand to inspect his nails as he waited for the elevator. “I gotta say, if the hand wasn’t attached to me, it would look really pretty. These nails are…. Hot” Danny thought to himself when he heard the sound of footsteps behind him.
Danny turned and saw a guy walking up to him busy looking at his phone. Danny had seen him a few times around the apartment building but couldn’t remember his name. Danny pretended to keep inspecting his nails but inside he was nervous as hell, but the weed kept him from running away. The guy looked up from his phone and did a double take at the bombshell in a leather skirt standing there. He looked her up and down, stopping to stare at his ass straining the leather skirt and his DDs threatening to pop out of his top. An easy smile grew on his face as he put his phone in his pocket and stood next to Danny at the elevator as the doors opened.
Danny minced inside the elevator after the guy gave a smooth “after you” holding out his arm to invite him in. The guy followed with his eyes glued to Danny’s ass swaying back and forth. Danny settled into the corner of the elevator when the guy asked what floor he wanted. “Umm… 6 please” Danny femininely responded, remembering to use his girly voice. The guy pressed the button and gave him another long look up and down his body.
Maybe it was the weed, maybe it was the built up horniness of the day, maybe it was the soft sensual feelings of his new clothes, or a combination of all three, but Danny found that he was enjoying this guy checking him out. He’d always been attractive, but pretty boy attractive. He’d never have girls undress him with their eyes like this guy was doing. It felt…. Nice? Good? To be appreciated for how he looked. He knew the weed was messing with his brain but he decided to enjoy it for a minute. Danny crossed one leg in front of the other and toyed with his body jewelry between his DDs as he looked at the guy. While Danny was never into guys at all, he looked at him and saw that he was conventionally attractive. Longish brown hair with a little wave and a hard part. Tall for him at 6’. His arms stretched the sleeves of his t-shirt. Yeah, he could say a guy was objectively attractive without being gay right? Like movie stars you can say are attractive right? Why can’t you say it about people in your life?
Danny sat there pondering, staring at the guys arms (they were pretty muscular. He must work out a lot) and didn’t hear the guy talking to him. “Huh? What was that?” Danny ditzily answered.
“Haha it’s ok. I was just wondering your name and if you lived in the building? Haven’t seen you around and I know I would remember you” the guy asked.
“Oh umm like yeah! I like, live here. And my names um Danny…. Elle! Danielle *giggle*!” The weed was making his brain slow, making him sound like a ditz. Danny almost slipped up saying his boy name and was happy that he caught it so a bright smile and a bubbly laugh came out of his mouth.
Before the guy could respond, the elevator dinged for Danny’s floor. “Like, it was nice meeting you. See you around!” Danny said to the ogling boy as he strutted out of the elevator with a little wave of his manicured hand. Still feeling good from the appreciative looks, Danny decided to flaunt it a bit and put a little extra wiggle in his steps. After a few short steps due to his tight skirt, Danny looked over his shoulder and saw the guy leaning his head out of the elevator around the corner to watch him walk. The guy was staring at his big butt and blushed with a smile when he saw he was caught. Danny gave a giggle and smile in return and strutted to his apartment.
Danny still had a smile on his face as he approached his apartment door. He’d forgotten in his haze what he was actually doing here and went into autopilot. He tried to turn the door knob but it was locked. He tried to reach into his pants pocket for his keys but all he found was smooth black leather. “Shit, forgot skirts don’t have pockets. That’s dumb, skirts should have pockets. It would be so useful” Danny thought as he swung his purse in front and rummaged around in there. Before he could find them, the door swung open to Demarcus looking down at the brunette beauty. Dressed in a white button down with several buttons undone at the top and black jeans and a pair of fresh Jordan’s on, Demarcus looked, well very handsome. “Objectively handsome of course!” Danny thought. He looked like he got a fresh fade hair cut and his beard only had slight 5 o’clock shadow, accentuating his angular jawline.
“Hey there, girl. Thought you were gunna message me when you were here. How’d you know where I lived?” Demarcus asked. Before Danny could answer, Demarcus was looking Danny up and down and a big smirk opened up his face. “Dammnnnnnn girl! I saw your video but up close and personal is so much better. You like fine as hell shawty! Give Daddy a little twirl, sweetness”
Danny realized he messed up. There’s no way “Danielle” should have known where Demarcus lived! But Demarcus gave him an opening being entranced by Danny’s slutty little outfit. “Shit, gotta make him forget how I found our apartment!”
Danny put a big smile on his face “*giggle* thank you D-Daddy” calling his buddy “Daddy” still made his stomach churn a bit. “I thought you might like my outfit. I-I chose it just for you *giggle*” Danny played up the bimbo act as he talked before doing a slow turn on his heel, making sure to push his butt out as he turned around. Danny finished by pressing his arms together pushing his faux cleavage up and giving another little girly giggle and looking up, way up, at the college basketball player. Even in his 5 inch pumps, Demarcus was a full foot taller than Danny at 6’ 10”.
“Please please please fall for the bimbo act! Use your dick not your brain! Wait don’t use your dick!” Danny thought to himself with a big smile, pink lips shining as he waited.
Demarcus’s smile got bigger seeing the little snow bunny flaunting her assets at the big black man. “Damn, her ass is amazing especially on a white girl. That skirt is skin tight. How can she even walk in it? But those tits! That sports bra must have been compressing them down or something cause gawd-DAMN!” Demarcus thought.
Demarcus loved all the attention the girls at school gave him, but most were gold diggers hoping to hook him in college before he made the league. But no girl had put this much effort before a date with him. Looking her up and down, he saw she must’ve gotten a tan as she her skin looked much darker and he saw the little heart on her hip just above her skirt. He saw the dangling pink heart from her navel too, really liking the girly accessory. She got her nails done too, looking at the long pink nails on her hands, but growing up with sisters he knew that they weren’t high quality. “I’ll pay for some nice long acrylics for her. All girls love a guy that will pamper her” Demarcus thought. He looked at her hair and saw that it wasn’t the same dark brunette as earlier that day, but had blonde highlights throughout. “Hmm I wonder what she’d look like as a blonde? Wonder if I can talk her into that” Demarcus thought.
“Mmmm good girl, Danielle. Daddy does like your outfit. I love that body jewelry, it really draws my attention” Demarcus gave a long glance at the two mounds on Danny’s chest. “ it looks like you just got out of the salon. I’m glad you dolled yourself up for me, girl. I always appreciate a girl going above and beyond. Come here and say hi, girl”
Demarcus’s big paws reach down around Danny, one on chin and the other right smack on Danny’s butt cheek, and pulled the feminized man to him. Dannys head was tilted back as his roomie leaned down and kissed him. Dannys head was swimming as the masculine lips met his own girly pink ones. The hand on his back kneaded his butt through the tight black leather mini skirt, moving the ever present plug inside of him. The weed accentuated the pleasure coursing through him, causing Danny to open his mouth and moan softly. Demarcus took the opportunity to snake his tongue into Danny’s mouth, kissing him more forcefully hearing the girly moan. Danny was lost in the sensations, high on weed and his pent up sexual arousal, and started kissing Demarcus back. Danny’s hands went up to Demarcus’s sculpted chest, feeling it for a moment before sliding down to his waist.
The two made out for a few moments, then a few more, and then a few more. After several minutes where Danny was practically panting with need, Demarcus took one of Danny’s small hands in his own and brought it down to the front of Demarcus’s pants where Danny felt a large, VERY large, bulge. Danny’s hand impulsively tightened from shock which made his hand grip the big snake in Demarcus’s pants. Before he could react anymore, Demarcus pulled back from the kiss.
“Mmmm damn girl! Those lips taste delicious. We better stop before I just take you inside rather than take you out. And looking the way you look right now, I wanna show off my new girl. And I think you wanna show off too don’t you sweetness?” Demarcus punctuated his question with a light slap on Danny’s rear, causing a small yelp from Danny.
“Umm… yes D-Daddy. I want to show off for you.” Danny answered, still flustered from the make out.
“Good girl. But I think you better let go so we can get going. Or do you wanna stay in?” Danny looked down and saw his pink nails still gripping the thick shaft through Demarcus’s jeans. Quickly pulling his hand away, Danny nervously smiled and giggled again. “S-sorry Daddy. Yes, let’s go!” In no rush to see the snake out of its prison, Danny grabbed Demarcus’s hand, lacing his fingers with Demarcus big black ones, and tried to pull the basketball star towards the elevator. Demarcus didn’t budge an inch from the weak effort, but just chuckled and started walking with the girly pink brunette towards the elevator.
On to the club?
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Masculinity Lost
How a straight guy was to become a sissy
Danny, a college womanizer, gets taught that his playboy days are over, and it’s time for him to become a different kind of Playboy
Updated on Jun 27, 2025
by Cdslavejessie
Created on Jan 13, 2024
by Cdslavejessie
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