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Chapter 28
by
Cdslavejessie
Final VIP section and then going back to who’s place?
A new job and VIP Humiliation
Jessica Jamie and Danny climbed back up the stairs to the VIP section finding it had gotten much more filled since they were on the dance floor. And also much more drunk. Bottles and glasses littered the tables and arms of chairs. A haze of smoke covered the area as they saw several blunts being passed around.
Large strong black men all well dressed clearly with money, sat joking and laughing with their brothers. Each of them had a pretty white girl dressed in something small and tight hanging onto their arm or sitting in their lap. A few interracial couples were making out on the couches. Danny saw in a dark corner there was a very large and buff black man facing the corner and you could just make out a pair of white legs on their knees and red heels poking out from between his legs.
Danny’s mind was much more relaxed at this point from the potent weed, calming down from his tormentors showing up on his date. “It’s not a date man! They’re forcing you to do this remember that! You’re a man and you love women!” A small voice said inside his brain but Danny could only faintly make it out in the fog of smoke so he ignored it, focusing on the happy chemicals in his brain and how good and horny he felt at the moment.
Danny scanned the room and saw Demarcus talking with a group of very well dressed men with probably tens of thousands of dollars in jewelry hanging off of them. Demarcus saw Danny staring at him and gave a happy smile back and waved him over. While his smile was happy, his eyes were intense, burning with passion and desire for the pretty brunette in a short skirt and heels. Danny’s stomach turned to butterflies at the intense stare and his clit twitched involuntarily from the appreciation and desire for him.
“Just let go. Play the part and no more punishment. Jessica and Jamie are here so don’t give them the opportunity to expose you. The guys here are big and Demarcus is huge you don’t want to get hurt. So play the part of Danielle, the ditzy bimbo.” Danny thought to himself. He strutted over to Demarcus, involuntarily putting significant wiggle and hip rocking to his walk, and grabbed onto Demarcus’s big buff arm.
“Hi Daddy, did you miss me?” Danny beamed up at Demarcus, lightly bouncing up and down to look eager to be back with Demarcus. But Danny forgot about his DDs and they jiggled with each bounce causing Demarcus’s eyes to stray from his face down to his chest.
“You’re damn right I did, Shawty. Here, let me introduce you to these fine gentlemen….” Demarcus started rattling off names but Danny quickly got lost in his fog, his thoughts elsewhere as the names and titles went in one ear and out the other. He put on a big friendly smile as each of the men shook his hand, which Danny daintily held out for each massive black paw. He assumed these guys were important, and rich based on how they looked. Danny thought he caught that most of them were professional ball players, and Danny could tell from their size. Danny thought he recognized a couple of them but his sports memory was lacking in his current state.
“Um, like im sorry? What was that?” Danny said when he saw them all looking at him waiting for a response.
One of them, a big guy with a short neatly trimmed goatee, laughed. “Nevermind sweetheart, just wondering if you liked basketball or just the players?”
Danny thought for a moment, touching a long tipped nail to his lip thinking. Not liking one team more than the other, he’d always liked players more than teams, following the superstars and rooting for them. “Um, like I love basketball! But I def love the players more *giggle*! Players are sooooo much more interesting and fun! OMG! You’re, like, you’re-you’re- you play for Boston! Omg you’re, like, super good!” Danny realized at that moment that these WERE professional basketball players. “Wow! That’s crazy! Can’t believe I’m hanging out with real NBA guys!” Danny thought.
The group laughed good naturedly at the brunette bimbo, cause Demarcus had introduced all of them just a few minutes ago. But the girl was cute so it just made her more endearing to them.
Looking them up and down, Danny stared in awe at the size of them. “Damn, basketball players really are big. I wonder if they’re all as big as Demarcus” Danny thought as he looked quickly at their crotches, or so he thought. But Danny didn’t realize that the looks he was giving weren’t ones of awe but ones of desire. His “quick” looks were actually stares at the guys bodies, especially their crotches. Danny had even licked his lips a few times unconsciously.
The guys definitely took notice of Danny’s hungry looks and knew they had a snow bunny by “her” constant giggles and girly voice and flirty mannerisms. It didn’t seem like she had a lot going on upstairs from her excessive use of “like, um, totally!” And how she would seemingly lose her train of thought mid sentence. These guys had seen “her” type a million times, but that didn’t mean they didn’t like it.
Demarcus saw the sharks circling, trying to move in on Demarcus’s “prize.” While he was still young, he wasn’t about to let these old heads alpha him and take his girl. So Demarcus wrapped one arm around Danny, firmly gripping his butt with one hand while forcefully tipping Danny’s chin up to meet his gaze.
Danny looked up at Demarcus through his big lashes, overcome by the passionate fire in his eyes that made him feel so small but desired at the same time. His eyes closed as Demarcus leaned in and quickly but forcefully kissed Danny. Danny melted as it felt like heat passed from Demarcus’s lips into his and down throughout his whole body. Involuntarily Danny’s right legged kicked back as he was kissed.
“Why don’t you go find Jessica and Jamie, girl? I’ll be with you in a minute. And get me another drink sweetness. Crown and diet.” Demarcus ordered.
“Y-yessss Daddy” Danny practically moaned, still feeling the kiss and Demarcus’s hand on his butt. But a soft slap on his butt got him moving, mincing over to Jamie and Jessica over on the couches. He looked over his shoulder once and caught the whole group, including Demarcus, staring at his ass as he walked away. Danny blushed, ashamed but also appreciative of the looks, and turned away but not before catching all the guys dapping up Demarcus. “Damn, white girl’s got a booty, dawg! Atta boy, big man!” Danny heard between the cheers and laughter. Danny blushed even harder as he scurried away.
Approaching Jessica and Jamie on the couch, Danny saw Jessica sitting alone while Danny was busy chatting with a handsome black man. The two were turned towards each other on the couch, knees touching as the man slowly stroked up and down Jamie’s stockinged thigh. Jamie was clearly more in his submissive sissy headspace as he giggled at his jokes, smiled a lot, and played with his hair while taking every opportunity to stroke the guy’s muscled arm.
But Jessica sat alone, giving off an aura of confidence and superiority. She motioned for Danny to come sit with her by patting the cushion next to her. Danny sat carefully, smoothing his skirt underneath him and pulling down the hem so as not to give a glimpse of what was underneath. He gave a sigh of relief being off his feet. The damn heels were a killer dancing and walking and standing so much. Leaning back and looking down at his legs and heels, Danny did admire how cute they looked. “They do make my legs and butt look great. And they are really sexy. I just wished I was looking at them on someone else” Danny thought. “But…. It is nice to have a personal sexy show of legs and heels whenever I want. Silver linings I guess”
As Danny pondered about his feminine lower body, he felt a sharp pinch on the side of his butt. He gave a yelp and looked at Jessica. “Sit up straight, sissy. And roll your shoulders back. A girl like you likes to show off the goods, not lean back like a deadbeat boy” Jessica ordered. Danny immediately straightened his spine, sitting on the edge of the couch, and rolled his shoulders back and pushing out his faux chest, making his boobs even more pronounced. He had his legs close together but decided to cross them at the ankle to further block the view under his skirt. “Can’t get caught now. I’d be beaten to a pulp” Danny thought.
“Good girl, Danielle! Oh and look, it’s your new besties Tiffany and Trixie!” Jessica motioned over for the two to come. The two bubbly blondes bounced over, tottering in their heels and almost spilling out of their tiny tube dresses. They looked like they had more to drink as they were very giggly and pink faced. Both were holding the hand of a large imposing bald black man.
He stood at 6’ 4” with a shaved bald head and a close cropped beard. There was some salt to the pepper in the beard, but his face still had the smoothness of youth. He wore a custom tailored black suit with expensive looking shoes. His suit probably cost more than Danny’s tuition. His suit outlined his muscular figure, looking like an NFL linebacker.
“Daniiiiii!! Omg you have to meet Deion!” Trixie excitedly said, bouncing while holding onto the man’s arm.
Tiffany leaned forward, whisper-shouting drunkenly for everyone to hear “he’s the owner of the club!” She said with an excited smile.
Deion smiled down at the feminized man, an imposing figure over Danny’s girly one. “Pleasure to meet you, Danielle. Come stand up let me get a look at you.” He held out his hand to help him up.
Not sure whether it was the weed or ****, or his fear of being outed, or the dominant aura Deion gave off, but Danny felt the need to do what this man said. Danny took Deions large hand in his own, slowly getting to his high heeled feet making sure to straighten and smooth out his skirt. He adjusted his top making sure nothing was spilling out (well more than it was supposed to in this top) and looked up at the man with a smile on his face.
“Beautiful, just like Trixie and Tiffany said you would be. Give me a twirl, girl. Let me see all of you.”
Danny blushed at being called beautiful, not just by Deion but by the sexy blonde bimbos too, and slowly spun on his heel. Subconsciously enjoying the attention, Danny stuck out his butt a little to really show it off.
“Mmm just perfect. Just perfect. With school coming to an end for the summer, I’m always looking to fill spots at my club. A lot of college girls work here during the year to pay for school, but then they leave for the summer. I was talking to your friends here as I have a few spots available and they told me about you. They were… well VERY enthusiastic that you would fit in very well at Spades. Seems you have the right…. Tastes to do well here. So, are you staying for the summer and need a job, Danielle?”
Danny’s mind was swimming between all the booze and weed and his own horniness stemming from his cage. “I’ve gotten way hornier since the bathroom goddamn that cage is tight. But I can’t work here as Danielle! That’s crazy!” Danny thought.
“Ummm I’m not staying in town….” Danny started to say before being interrupted by Jessica.
“Oh Danielle this is perfect! You were just saying how you were trying to figure out how to pay for your rent this summer! And with you having to move out of your old apartment, this will be perfect! And we all know you’ll have so much fun working here hahahaha Say yes, girlie!”
Danny looked bewildered at Jessica. He was planning on going home for summer and working at his dad’s friends firm as a paid intern. Easy gig mostly just flirting with the other coeds and partying all summer. But Jessica said he was staying in town?? But looking at Jessica and her fierce look, Danny knew now wasn’t the time to question it. With trepidation, Danny looked back at Deion.
“Um, like yeah! That would be totally great!” He said in his new found cheery tone. The “twins” squealed, hugging Danny and chattering about how fun this summer was going to be. Danny felt their breasts press into his own and despite his best efforts squealed as his dick squeezed tighter in his cage at the sensation. The girls took that for the same enthusiasm, so excited they had another girl that thought like them. “You know, she’d look sooooo much better as a blonde. And we’d all match” Tiffany thought.
Deion chuckled scribbling something down on a business card “well that’s it then. Here’s my card. I expect you three here on Saturday at 7 pm to get all set up. We’ll have uniforms ready for you girls, just bring your own heels. We have an image to maintain so nothing below 4 inches. It’ll be a pleasure working with you, Danielle.” He patted the top of Danny’s head like a dog before brushing his cheek and ripping his head up to look at him. “I’m sure you’ll be a good little worker. I like my girls obedient, you understand?” Danny quickly nodded his head, entranced by Deion’s aura. “Good girl, I’ll see you Saturday” He took Danny’s tiny hand in his own and gently kissed his fingers before stepping away with the blonde bimbos on both arms.
Jessica laughed once they were out of earshot. “Hahahaha oh perfect, Danielle! Now you have a job that fits your new look. And will help pay your rent to me. Yes, you’re going to be moving in with me tomorrow. I thought you’d appreciate me doing that for you so you don’t have to explain to Demarcus why “Danielle” is living in Danny’s room. Now thank me properly for getting you out of that sticky situation and kiss my ring, bitch”
Danny’s mind whirled, lost with all the dramatic changes in his life, he simply took Jessica’s preferred hand and pressed his lips to her ornate ring. “Thank you, Mistress for giving me a place to live and a new job”
Jessica smirked at the power she held over him. “Good girl. Youll love living with me and your new job. We know you love em tall dark and handsome and this place is teeming with cute black guys hahahahha you know why this place is called Spades right?” Danny shook his head no. “Oh you naive little girl. Well, a spade is a sign of black ownership. Girls who wear a spade are proudly saying they only like black men. Spades is a club that adheres strictly to that notion. You notice there are no white men here?”
Realization hit him like a ton of bricks. Of course that’s what this club was! He looked around and the only white people he saw were white women. A lot his age but some older as well. He even saw a few wedding rings on some women. He was at a blacks only club, and now would be working at one! He remembered all the spade logos on the waitresses and remembered the tattoos on some of them. “Omg she wouldn’t do that to me, would she???” Danny thought worriedly.
She pointedly looked over at Demarcus and his friends. “You seem to fit right in with Demarcus and his boys. Makes sense cause you WERE one of his boys hahahha how do you like being Demarcus’s arm candy? Does it feel good to be ogled and desired by all these big strong black men? Tell me, Dani” Jessica looked deep into Danny’s eyes. Her strong blue eyes felt so dominating and powerful. He was so captivated by her domineering gaze that in his **** state he told the truth.
“…. y-yes. It feels… good to be desired” Danny practically whispered. He immediately felt shame as he realized what he said. He had just admitted, out loud, that he enjoyed being ogled and wanted and admired by men to his ex girlfriend. He should have denied it, wanted to deny it, but remembering the powerful and passionate looks Demarcus would give him made his stomach turn to butterflies. Feeling so small in his powerful arms. But the humiliation from admitting that was too much for Danny. He adverted his gaze from Jessicas’s dominant one, looking down at his feet. Or he would be looking at his feet if his DDs weren’t in the way. More humiliation washed over him looking at his shiny tanned cleavage. “I shouldn’t look like this. I shouldn’t feel like this. I’m a man not gay or a girl! Stop it Danny stop it!” Danny thought.
Jessica continued her dominant look for a moment, seeming to think for a moment, before erupting in laughter. “Hahahahaha omg it’s only been a day and you’re already turned! You little sissy slut! You like being a pretty piece of arm candy. Being watched as you wiggle and jiggle in front of a bunch of hungry horny men! You little fag hahahaha that’s just precious honey! Don’t worry, we’ll make sure you’re watched sweetheart.” Jessica’s wicked smile spread across her face as she came up with a plan. “When Demarcus comes over here, you’re gunna plop that big butt right in his lap and you’re gunna give him a hand job right here on the couch.”
Danny put his manicured hand up to his mouth in feminine surprise at Jessica’s order. There’s no way he could do that! Even being **** to make Jamie’s cock squirt, he was still coming to grips with what that meant. And he had basically been **** to do it, in the privacy of a room. Well, not technically private as the girls had been watching, but not dozens of people!
But Jessica made the decision for him “remember, sissy Dani. I own you now. I’ll expose you to everyone here and then release allllll the videos and pics I have of you. Confessing that you’ve been a closet sissy fag all along. All the dress up sessions. Walking practice. Your strip tease! You sucking Jamie’s cock, twice btw! Your cum swapping make out with Candi. Your life as you know it will be over. So, be a good girl and make your Daddy happy. Say it now, sissy. Say you’ll be a good girl for Mistress”
Jessica lightly stroked the side of Danny’s face as she ordered him. Danny’s hands were tied. He couldn’t let all this get out. What will his friends and fellow students think? What would his family think??? Danny cringed thinking of his hard nosed, ex military father seeing him prancing around in lingerie professing he was a pretty sissy girl. Dejectedly, Danny hung his head and said, “I’ll be a good girl for you Mistress”
“No, look at me when you say it. And put a smile on. Embellish a little. Make me proud” Jessica dug her nails into the soft flesh of Danny’s thigh, causing him to wince.
Danny looked into Jessica’s deep blue eyes and plastered a smile on his face. “I’ll, like, totally be a good girl for you Mistress! I’ll make Daddy super happy and have all the boys and men wanting me soooooo bad!”
Danny practically gagged as he said it, but leaning into the ditzy bimbo role was the only thing keeping him sane. Jessica smiled at Danny’s announcement.
“Perfect. Just perfect. Being an air headed bimbo is just perfect for you, Danielle. Now, make sure Daddy is happy, be over the top and make him want it. Oh just in time, your boyfriend is coming over” Jessica said as Demarcus sauntered over. He looked at Danny the whole time, an easy smile on his face. And he didn’t walk, he more prowled like a panther through the jungle, unafraid and confident that nothing could hurt him as the alpha. Danny watched with wide eyes, both incredibly fearful of what was coming… but also fascinated by his aura. He’d never looked at Demarcus this way in the past, he was just a buddy of his. But now he saw why girls were throwing themselves at him.
“Hey baby girl. I see you’re catching up with Jess. Mind if I join?”
“Remember your role. Ditzy pretty airhead. Make him want you.” Danny thought.
“*giggle* of course, Daddy! You can sit right here!” Danny bounced up, making his titties jiggle before turning around and bending at the waist. “Oh shoot! There’s a spot here. Let me clean it up first” Danny started wiping away imaginary dust, making sure his butt wiggled back and forth invitingly. Snapping back up at the waist making sure his hair went flying, Danny turned around with a big fake smile.
Demarcus grinned, loving the attention Danielle gave to him as he sat. “Girl’s got it bad for me. I like that. She might not be the brightest but she’s sweet and nice and my boys like her too. Plus she’s a smoke show. Those tits are amazing but nothing on her ass. Can’t wait to get a piece of that.” Demarcus thought before his thought was cut short by that very ass plopping down on Demarcus’s knee.
“There’s not enough room for all of us, but I’m sure you won’t mind, will you Daddy?” Danny batted his fake lashes and lightly stroked Demarcus’s defined pecs.
“No not at all baby girl, not at all. What were you two talking about before I intruded?”
Jessica laughed but Danny kept stroking nervously along his chest. “Oh erm… uh nothing daddy. Just girl stuff! But YOU are much more interesting!” Danny felt like he had to change the topic so he gripped Demarcus’s shirt and leaned in and forcefully kissed him. This was the first time Danny had initiated a kiss with a guy and he didn’t necessarily like what that meant. But it was better than the alternative. So Danny kissed him with passion, rubbing his chest while wiggling his big butt into Demarcus’s powerful thigh.
Demarcus was off kilter at the passionate kiss, taking a back role for the moment. But that didn’t last long as he quickly took back control, kissing Danny back and dominating his mouth. He had one arm behind Danny’s back and the other kneading and rubbing his thigh.
“Now or never. God, please don’t let anyone see.” Danny prayed as he took his delicate hand down Demarcus’s strong rippling body to his crotch. The bulge in his crotch was semi hard but twitching and moving. Danny traced the outline through the pants with his fingernail, and kept tracing, and kept tracing, and kept tracing until finally he had traced the whole outline. “Holy fuck he’s big! Please don’t have him put that thing in me! I’ll die!” Danny silently begged.
Feeling Danny’s exploration down below, Demarcus laughed to himself. “Oh the little bitch is adventurous for sure. I’ll play her game.” Demarcus’s hand slid up his thigh, tracing Danny’s tight abdomen before coming to rest on his faux chest. As the big strong black hand rubbed his nipple, Danny gasped, opening his mouth wide inviting Demarcus’s tongue in further.
Danny, ignited with passion, quickly undid Demarcus’s fly and stuck his hand inside. Grasping the huge phallus through his boxers, Danny couldn’t believe the size. He couldn’t put his whole hand around it!
Demarcus pulled away from the kiss, kissing and nibbling up Danny’s neck until he reached his ear. “Go on shawty. I know you like putting on a show. Let’s give em a show. Pull out Daddy’s cock baby girl.” Demarcus whispered before sticking his tongue in Danny’s ear and pinching Danny’s nipple.
The sudden pleasure made Danny moan loudly, enough for the couple next to them to take notice. They saw a tanned bimbo writhing in pleasure, her plump pink lips wide, eyes closed showing off her pretty pink eye shadow and fake lashes. Her body barely covered in clothing being man handled by a large black hand fondling her DDs through her “top”. And her hand was snaking into her dates pants, very clearly doing some fondling of her own. The couple smirked at each other, the white girl biting her lip watching the scene unfold.
Danny was overcome with feelings, feminine feelings of submission and wanting to please, and his body moved on its own. He felt his hand pull down Demarcus’s boxer briefs and unbutton his pants and let the monster free. Danny looked down through the pleasure his body was in and saw Demarcus’s naked cock hard for the first time. His gasp of surprise was quickly turned into a moan as another electric shock flowed through his nipples. Danny grabbed onto the naked appendage, watching his fake pink nails wrap around the beer can sized cock. The pink such a contrast to the dark skin underneath. Entranced, feeling like he was watching someone else do it, he slowly stroked his hand up and down the rigid cock. Slowly rising up and down, lips parted and panting, Danny felt like he was watching interracial porn. Danny felt Demarcus’s hand snake under his top and bra and starting caressing his nipples directly. “Eeeeppp! Unnghhh! Omg! Omg! Omg! Mmmmmm” was all Danny could get out as he jerked off the cock faster.
“Mmmm that’s right baby girl, jerk my cock for me. It’s all for your shawty. Look at your little white hand jerking it up and down” Danny looked and saw how tiny his hand looked against the thick veiny monster. “You love that don’t you? Your white skin against my dark skin. You love being a little snow bunny, showing off how much you love big black cock to everyone. Say it, Danielle. Say you’re a slut for big black cock”
At that moment, while still playing with Danny’s nipple, Demarcus other hand slid to the back of Danny’s skirt and felt for the plug he saw earlier. He pressed hard on the plug through the skirt. “This bitch is kinky as hell, she loves this shit” Demarcus thought.
Danny was overcome with feelings, his nipples, his butt, all too much for him. Even his cock in his cage was spasming wildly. He lustfully moaned out “mmmmmmmmMMMMMMM! Yesssss Daddy! I love big black cock! I’m a little snow bunny for big black mennnnnmmmm!!!” His last words melted into a moan as he jerked Demarcus off faster.
Suddenly, Demarcus stopped his toying of Danny and gently grabbed the hand that was jerking him off. “Good girl. I know you love showing off. Look around and take a lot at the audience girl.”
Danny looked up, still panting from pleasure and saw at least a dozen people watching him. The couple next to him had taken a page from his book and the white girl was slowly tracing the outline of the guys cock through his pants as he leaned back and sipped his drink. Demarcus’s boys were watching, giving dap ups to one another for their boy. Even the pro player from Boston was grinning ear to ear watching Danny jerk off Demarcus, the guy Danny looked up to as an idol. Shame courses through him, but he realized he didn’t let go of Demarcus’s cock.
He looked over and said Tiffany and Trixie cuddling up to Jamal and Chris. He heard Tiffany fake whisper “See! I told you she was one of us! Were gunna be besties!”
And there was Jamie, still sitting on that guys lap, her big DDs shoved in the guys face as he licked and kissed them. But her eyes were only on Danny, filled with fire and passion watching her former bully wrap his tiny hand around a black cock.
But the final humiliation was Jessica. Sitting right next to Danny, stirring her cocktail with a wry smile on her face. His ex girlfriend had just seen him “willingly” seduce his best friend and jerk him off. Her blue eyes bored into his soul, degrading him completely. She leaned over, her breasts threatening to spill out of her corset, and whispered to the two lovers.
“That was fucking hot! How about we go back to your place, Demarcus, and get this party going?”
Demarcus smiled, looking at the two scantily clad chicks with him, and nodded his head. Dread coursed through Danny’s body as the three stood up. Out they walked, Demarcus in the middle with his arm around Jessica’s bare shoulders and his hand directly on Danny’s ass. Danny gulped, dreading what was to come, but why was he still trying to get so hard???
Demarcus’s place
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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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