Chapter 32
by
Cdslavejessie
What happens at Britney’s?
Britney learns about Dani, Dani gets a uniform
Danny walked up to the familiar entrance of his apartment building with trepidation. Well, his former apartment building, as he’d officially moved out earlier that day. The realization that the building that used to be his home as a boy, where he’d drink beer and play video games hanging out with his buddies, where he’d bring home girls from his frat parties and do what any red blooded man would do with a beautiful girl, was now in his past hit him hard as he looked up at it. How had his life changed so quickly? It was only a few days ago that he was lounging in his room in comfortable sweats playing madden with his buddies. He had to get his life back. His despair turned back to hope, as he was determined now to get rid of all the lace and silk and heels and panties and get back his manhood.
But first he had to deal with the nearest alligator to the boat. And that was Britney. He had no idea how she found out that Danielle was actually Danny and he needed to make sure she kept it a secret. Regaining his manhood would do little good if everyone found out he was a slutty girl with a black boyfriend. Demarcus wasn’t his boyfriend right? They’d only been on one date, he wouldn’t expect him to be in a relationship would he? What was he thinking! He couldn’t think about boyfriends! He’s straight! He was **** into all this. “Damn my brain is a mess right now” he thought to himself.
Maybe she could help him out of his **** from Jessica? Was it worth the risk? Would she be willing to help him? She seemed like she enjoyed him as Danielle from their encounter at the gym, so would she even want Danny back?
Danny stood in front of the elevator, adjusting his top so it didn’t fall down too much. Showering at the gym was something Danny definitely wasn’t ready for, having to go to the women’s locker room. What would have been a dream for Danny a few days ago would now be a nightmare, fearful his caged friend would be seen by the college girls as he changed. He didn’t want to end up on some viral video of a transgender woman wearing a cage in a woman’s room! So he quickly headed back to his new apartment to shower and change. Thankfully, he didn’t have to try and figure out an outfit on his own as Jessica had left him outfit to put on. But maybe he would have been better off on his own as the outfit was way more revealing than he wanted. But, he did think it was cute, not quite realizing that he was already starting to think of his girly outfits as cute.
He was wearing a white off the shoulder cropped top. The top had long flouncy sleeves that stopped at his wrists and connected to the bodice of his top, showing off his bare shoulders and upper arms. His tan was still strong from yesterday, so the bikini tan lines around his neck were a striking difference from the sun kissed skin of his collar bones. The bodice itself was a stretchy material that was very tight, showing off the curves of his new chest in intimate detail. Thankfully, Jessica didn’t have him wear a pink or black bra underneath, as that would have been tacky and trashy. The white push up strapless bra had some lace detailing on the cups and was very sexy, but couldn’t be seen through the top. The neckline of the top was heart shaped, tracing the tops of his pushed up breasts. The bottom of the top came just above his navel, showing off his pink dangly heart piercing.
He also carefully adjusted his denim mini skirt. While not an ultra mini, it still felt far too short on his legs, showing off far more of his tanned and oiled legs than he wanted to. The denim skirt was low waisted, showing off his navel as well as his heart shaped tan line on his hip. The skirt was also stretchy which allowed some freedom of movement but also was very tight on his heart shaped butt, showing off every curve. Underneath he wore a white silk thong with A thick lace waist band. The Y shape in the back cut perfectly between his tanned butt cheeks. Of course included in his outfit was his silver butt plug with the pink heart shaped gem, which was now lodged deep inside Danny’s butt. He found it slid in a lot easier now, and was much less uncomfortable than just a few days ago. It actually felt good and kinda… right for it to be inside him.
His legs were bare below his jean mini skirt and freshly oiled, gleaming in the May early afternoon sun. In his feet he wore a pair of strappy brown heeled wedges with a cork wedge on the bottom. Of course the wedges were still tall at 6 inches with a 1 inch hidden platform, but Danny found them much more comfortable than his usual stilettos he’d been wearing. His pink toenails gleamed through the strappy open toed look.
Thankfully, Danny didn’t need to do much to his make up, but Jessica had insisted he put on lip stick when he wasn’t at the gym. He wore a bubble gum pink glossy lipstick with over lined lips making them appear larger. His fake eyelashes were still well in place from the glue and his dark Smokey eye with inner corners of white, while a little heavy for his casual outfit, still looked impeccable. His cheeks were pink from blush and his contour and concealer made his jaw smaller and face much more feminine. His eyebrows were still carefully manicured and dark and looked even better with some eyebrow pencil outlining them.
His hair was out of its braids, but not out of the ultra girly bows. Instead of two braids he had brushed out his hair and put it into a pony tail with an intricate knot at the base. At the knot, a big white bow sat at the back of his head, making the casual outfit much much girlier in his eyes.
The elevator door opened and thankfully no one was waiting as Danny stepped out onto Britney’s floor, a few floors below Danny’s old apartment. Danny was thankful Demarcus didn’t decide to pop out at that point cause with how he looked like a cute sorority girl on a day out, there’s no way Danny would have gotten away from his powerful hands. He knew he looked good and that’s what scared him the most.
Danny walked down the hallway, carefully heel to toe due to his heels, big butt swaying side to side in his denim skirt. He arrived at Britney’s door and took a big breath, his breasts heaving with the effort. God he was never gunna get used to that, seeing his boobs in his lower peripherals as all times and unable to look past them when he looked down. He brought his pink nailed hand up to the door and carefully knocked a couple times.
“Just a minute!” Britney’s cheery voice called out. Danny nervously rocked back and forth on his wedges. The door opened and Britney stood there still in her gym outfit from earlier but dripping sweat. “Sorry was just finishing up some cardio and abs, about to get in the shower. You look soooooo CUTE btw! I love your top! And THOSE look so real! How did you…. Nevermind tell me more in a minute come in” Britney was staring at the big pushed up globes pouring out of his cropped top before grabbing his hand and pulling him inside. Danny almost fell from the strong pull, gosh she was strong, but kept his footing and clipped along behind the persistent and strong pulling of Britney.
The two entered Britney’s surprisingly spacious two bed room apartment. There was an open floor plan kitchen/living area separated by a tile counter top. The kitchen was covered in protein powders and other fitness food products, relatively messy. The living area was relatively clean with a single couch and coffee table in front of a TV, but could use some vacuuming and dusting. The master bedroom was full of clothes, mostly work out clothes but some casual clothes as well as some sexy lingerie. It looked like a bomb had gone off in her closet. The bathroom was a mess, like most girls bathrooms the counter was covered in various cosmetics and lotions and products. The white countertop had powders and liquid cosmetic leaks all over it. The shower and toilet were relatively clean.
The second bedroom Britney had converted to an in home gym with a treadmill, bench and squat rack, and dumb bell rack. There were weights all over the place, a lot of them very heavy.
Britney brought Danny into the living area and sat down on the couch, still breathing heavily with sweat pouring down her face and chest as she sipped on a bottle of water. Danny moved to sit next to her, smoothing his skirt in the back as he did. Britney giggled at the feminine action as Danny sat gingerly down next to her so he didn’t push in his plug.
Britney took another sip of water as she eyed Danny critically without saying a word. Danny just nervously shifted in his seat looking down. He tried to tug down his skirt hem line more to cover his exposed tanned legs, but it barely did anything. He looked back up at Britney and just saw her staring curiously at him. Shame filled him for the millionth time this week, being under such close scrutiny with a former girlfriend who knew who he was. So humiliated and emasculated that she knows this tanned bimbo is actually her former alpha masculine lover.
The silence stretched and he couldn’t take it anymore. “Ok, like, how did you know?!?“ unable to stop his new bimbo lingo from leaking in and mentally kicking himself for sounding so ditzy.
Britney smiled at his girly vocab before setting her water down. Looking into his made up eyes (wow he did a great job on his make up!) Britney said, “I didn’t know at first but had my suspicions last night. Your face is super pretty and feminine but you looked so familiar. Seeing you with Demarcus though really started putting it together. You are really short, sorry but you are, and it was always wild seeing you two standing next to each other. Plus, your butt gave you away. I’ll remember that big juicy butt forever hahaha”
“But I still wasn’t 100% sure until the gym today. When you bent over I could see a tiny little bulge in your shorts. I’m sure no one else saw it but I was looking for it. I didn’t know you were so kinky that you wore a chastity cage sweetie. We could have had a lot of fun hahaha”
Britney put her hand on Danny’s bare thigh and looked him deep in the eyes. “So now I have a question. Well, so many questions actually. When did this happen?? I saw you like a month ago and you didn’t look…. *gestures to his body* like this? Are you trans? And Demarcus is into it?”
Danny took a deep breath and closed his eyes, thinking back on his conversation with Jessica earlier when he told her the situation at the gym and how Britney knew who he was.
“Well it was bound to happen at some point, but it doesn’t change anything.” Jessica told him while watching him lightly dust his cheeks with blush. “You know the consequences for trying to get out from under my thumb. Remember what happened when you tried to tell Jamie? You’d look really cute with that playboy tan line as a tattoo. Maybe a tramp stamp of a spade?”
Danny almost dropped the brush in shock as he turned to Jessica. She looked at him hard with menace in her eyes as she reached under his skirt and gripped his balls, HARD. He knew she wasn’t joking. Everything up to this point was temporary. The tan would fade. His hair would grow back. His tits could be removed. All that would remain was the mental scars. But a tattoo was permanent!
Danny just babbled, “Yes Mistress! I’ll be a good girl for you! She won’t know you blackmailed me I promise Mistress!”
Jessica relinquished her grip on his manhood and smiled and patted his head like a dog. “Good girl” was all she said as Danny went back to powdering his nose.
But now, in Britney’s apartment, Danny was struggling. Could this be his chance at freedom? Could Britney help him? She didn’t have any ties to Jessica as far as he knew. Maybe she could get him out of this mess.
Danny took a deep breath, watching his faux breasts rise and fall with the action and took the plunge. He told Britney everything. How Jessica tricked him into dressing that first time. How she took blackmailing videos of him saying he was always a sissy. Sucking the dildo and cumming from a vibrator. Randomly meeting Demarcus outside his apartment and somehow ending up with a date with him. The trip to the salon and how he looked how he did now, as well as the “practice” at the salon with Jamie and Candi. Going on the date with Demarcus and ending up back at his apartment. And how Jessica moved him in with her and he was stuck like this for the time being. Everything.
Britney was silent the entire story as Danny told his sordid tale and remained silent while looking at his blue eyes. Danny couldn’t figure out what was going on in her head and started to squirm waiting for her response.
Finally, Britney put her hand on Danny’s bare thigh and lightly gripped it and grabbed Danny’s hand in her own. She smiled at Danny and Danny was filled with hope. Yes! He could finally be free of his pantied prison sentence!
“That is some story. Come with me, Danielle.” Britney kept her grip on Danny’s hand and pulled him to his high heeled feet. Danny was confused by the feminine use of his name but followed behind the buff body builder.
The two entered Britney’s room and Danny saw an outfit laid out on her queen sized bed that made him worried.
Britney grabbed both of Danny’s hands and looked into his fearful blue eyes. “Now, that story is something. And if it’s true, which it might be, or a lie, it doesn’t matter to me. I can tell THIS” gestures to Danny’s feminine outfit and big breasts, “fits you better. I knew from when we were together that you’re a true submissive at heart. The way you just immediately followed my commands and how cute you were being ridden while I fucked your little dick, and I fucked you not the other way around, I could tell that’s where you belonged.”
Britney grabbed his waist and moved him to the full length mirror. Danny looked at himself in his cute little cropped off the shoulder white top with his big DDs pushed up on display in the sweetheart neckline. Denim mini skirt tight to his thighs and showing off so much of his tanned thighs. His legs toned and accentuated by the heeled wedges on his feet. “And seeing you today at the gym fitting in with your two bimbo friends, who are cute as hell btw. You were practically their twin, well triplet I guess. Your girly girl mannerisms were super cute with your new… aesthetic. It fits perfectly. And you seemed… happier with them. When you’re with your frat buddies you just seemed like a shell of yourself. And they’re always messing with you too. Tell me I’m wrong.”
Danny looked in the mirror at his beautifully made up face. His long lashes and beautiful eye shadow. His face contoured to perfection. His hair in its cute up do. And he thought about how he did enjoy hanging out with Tiffany and trixie. Sure they were dumb but they were nice and sweet and fun to hang out with. Probably the nicest interactions he’s had with friends in awhile.
“And then seeing you with Demarcus. How you clung to his arm and the loving and adoring looks you’d give him. You’re saying you were **** into this but you always looked up to him, physically and mentally. You liked being his girl and him controlling you didn’t you?”
Danny blushed remembering the good feelings of being in his strong arms, his hands gripping his butt, the dominant gaze filled with desire when he looked at him. And the feeling of his hard throbbing cock in his hand as he stroked it. The feeling of it entering his throat and **** him. Danny started to blush and didn’t answer Britney, but that was all the answer she was looking for.
“Yeah, that’s what I thought. So here’s the deal. I won’t tell your Mistress that you told on her. That’s something to deal with between the two of you. But I feel like you were treated harshly in your sissy servitude, so I’m going to show you how good it can feel being a submissive to a true dominant. Sure you got a taste with Jessica and Jamie and even Demarcus, but girl, you ain’t seen nothing yet.” Britney gripped his big butt in her strong hand, making Danny involuntarily moan.
“Yeah that’s a good girl. So, you’re going to be my plaything this afternoon and then we can go from there. I won’t **** you, but I can promise you that you’ll enjoy it. It’s not sunshine and rainbows though girl, but same pain and discomfort can still feel good which I think you already know” Britney slapped his ass hard, forcing the plug to go deeper inside him making him moan again.
“Now, you’re still going to honor your bet and clean up my apartment. And you can’t do it in that outfit. So let’s get you dressed for your duties, sissy.”
Danny looked her in the eyes through the mirror and made a decision. He wasn’t going to get Britney’s help getting out of this prison, but…. He could get some relief. He was so damn horny and Britney was toying with him in just the right way.
After a moment He shyly nodded. Britney slapped his butt again before unbuttoning his skirt and sliding it down his wide hips, showing off his lace and silk thong and his tiny little caged bulge in the front.
“I love your little bulge sissy girl! Too bad we can’t get you out of it, but we have different ways to take care of each other.”
Danny shuddered as her strong hand lightly brushed his caged dick, causing it to twitch and jerk in its silk panties. Britney giggled before helping him out of his top and heels leaving him in just his lace strapless bra and thong.
“Your underwear is cute so you can leave the thong but the bra needs to change. I got something else for you girly.” Britney unfastened his bra and let it fall to the floor, causing Danny’s boobs to jiggle from the sudden lack of support. “God they look so real!” Britney exclaimed as she took both hands and cupped them, bouncing them in her palms to watch them move. Danny was humiliated having his ex lover play with his breasts he didn’t want, until she gently rubbed her thumbs against the nipples. The girly moan was louder this time and Danny was too late biting his lip to hide it. Britney was confused that he made that noise from rubbing fake silicone. “They have… electrodes in them that stimulate my nipples underneath” Danny sheepishly replied wanting to explain his sudden noises. Britney just grinned in response before firmly pinching both nipples, making Danny yelp in pleasure and pain.
“Ooooooo these will be FUN! Now let’s get you into something more fitting for your task”
Danny looked with trepidation at the outfit laid out on the bed and sighed. “God this is going to be humiliating. But fuck I need to cum! Get through it, Danny. You already accepted it” he thought to himself.
Danny stood while Britney wrapped a latex garter skirt around his waist. The thing went from just above his belly button to just below the bottom of his butt cheeks in shiny black leather, threatening to expose his cage at the slightest bend. The top and bottom was trimmed with white ruffles. With how tight the leather was, you could see every outline of his cage in the leather. This was the first time an outfit showed off his bulge rather than hid it, and it made Danny way more uncomfortable. He’d never been worried about if his bulge was seen before cause all guys had them. But now, his hair in a girly ponytail and make up covering his face and huge tits attached to his chest, it just felt wrong for it to be out there. Especially since it wasn’t just his dick but a chastity cage showing through, pinpointing him as a beta bitch, in his eyes. Danny hoped there was something else to cover up the short garter skirt, but he didn’t see anything that might on the bed.
What made it worse was the corseted back, which Danny unfortunately was used to but dreaded it all the same. He yelped as Britney’s strong arms pulled the strings tight in the back.
“Breathe out, baby girl, we’re gunna get your waist nice and tight like I like em”
Danny submissively nodded and let out the last of his breath as Britney pulled even harder and tied the laces in a cute bow in the back. Danny could barely breath at first before he adjusted his breathing, breathing from his chest rather than his stomach, and was able to get a somewhat normal rhythm. He looked in the mirror and saw a ridiculous hourglass staring back at him. With his DDs and gym-worked hips and butt, his proportions were only feminine. No guy could have dimensions like this. And not so much feminine as bimbo in their size difference. Danny cringed that only a few days and some padding up top could bring his figure to such dramatic changes.
Danny sat on the bed and rolled up the silk stockings into a little donut before sliding them up his smooth tan legs. He still couldn’t get over the feeling over silk stockings on his smooth legs and squirmed a bit from the sensation. Rolling smoothing both stockings so there were no wrinkles and making sure the back seams were straight, Danny clipped the six garters to the stocking welt. Well, struggled really with his long pink finger nails but he had improved his technique with all his practice. The stockings went up high on his thick thighs, but still left a bit of tanned flesh between the welt of the stocking and the bottom of his tiny leather garter skirt.
Britney handed him a black shiny leather balconnette bra with the same white ruffles around the cups and the straps. The cups barely covered the nipples of his faux breasts, leaving much of the upper boobs exposed. The white ruffles were especially humiliating to Danny as they just seemed excessively feminine, more so than the exposed skin. The cups lifted his boobs so they appeared perky and inviting, more so than normal, while also providing no support to the constant jiggling from the silicone weight inside them. Every step made a ripple in his chest and Danny felt them tugging as the bounced up and down.
Britney then handed him black satin gloves that came up past his elbows stopping on his upper arm with a little white bow on side of his arm. Danny slid the soft satin up his hairless arm, getting a smaller but similar sensual feeling as sliding stockings up his hairless legs. Looking at his arms covered in the soft fabric and seeing how much more effeminate they made them look crushed Danny’s masculinity even more. They were so thin and dainty, damn his genetics!
But the worst was to come. Britney came out of her closet with an extremely sexy set of **** devices in her hands. Thigh high shiny black leather stilletos with a 6 inch heel. But these heels had no hidden platform, so Danny’s poor feet would be arched even more than normal. Danny was happy with the relatively comfortable wedges he had been wearing, especially with how his feet and ankles hadn’t been the same when wearing flat shoes, but these looked brutal. But even he had to admit they were incredibly sexy, as his locked dick made itself known with a painful twitch.
Danny slowly slid up the right leather fabric of the boots up his thighs. The leather was skin tight, caressing every curve of his toned and tanned legs. Fixing the thigh high boots up around mid thigh, leaving a few inches of exposed stocking above, Danny zipped them up and felt the full tightness of them. He tentatively stood up, wobbling for a moment on the high arch of his feet, before regaining his footing. With his breasts making him top heavy, he rolled his shoulders back pulling them back to support the added weight so he didn’t fall forward. His breasts were thrust forward, prominent in the black leather balaconnete bra. Danny looked down and saw two tanned globes of flesh that looked like they’d **** him if they were pushed up any higher.
A few final touches were added. Britney liked the girly bow in his pony tail and left it but added a little maids cap to the top of his head, black satin with white ruffles. A tiny little “apron”, if it could be called that, of black satin and white ruffles that was no more than a few inches across was tied around his waist, coming to rest just above his pubic area leaving his bulging cage on display. She also added a black choker around his neck that had the same white ruffles on the top and bottom. Danny wasn’t expecting the click of a lock as the tight choker was closed on his neck. He turned to look, his made up eyes going wide seeing Britney’s smirk.
“Just a little something to get you into more of a subby move. Well, if the maid outfit didn’t work then the locked choker will hahaha” Britney said as Danny panicked feeling how tight it felt around his neck and realizing that he couldn’t get it off without Britney’s help.
“Ok, sissy girl, I think it’s time you get to work on that bet now that you’re maid up correctly, pardon the pun hahaha”
“Wait, you really want me to clean, in THIS???” Danny asked.
“Yes, why else would you be dressed as a maid? And no back talk from the help, sissy. That’s one demerit”
“Demerit?? What do those do??” Danny asked fearful
“That’s two more demerits. One for asking another stupid question and another for not addressing me properly. You’ll find out soon enough what demerits mean sissy. Don’t worry, I won’t be harsh like Jessica but I do LOVE dominating little subbies”
Danny let out a sigh of relief before bowing his head “Yes….. Mistress”
“Good girl, now get to work. I’m gunna shower and clean up. Make me a smoothie first with the protein powder on the counter and then get to work.” Britney spanked him, right on his plug, causing him to moan and jump, making his titties jiggle in their bra. Britney laughed while looking at this feminized fetishized maid with pure lust before sauntering into the bathroom. Not before stripping her sports bra off and tossing it at Danny’s feet, playfully looking over her shoulder and not giving him a glimpse of her bare breasts.
Danny shuddered seeing Britney’s powerful naked back and his normal heterosexual feelings came back to the forefront, but were stopped when his dick got painful in his cage. Shaking his head, Danny carefully minced out of the bedroom into the kitchen, his butt wiggling and tits jiggling with each step.
What happens during cleaning and after?
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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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