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Chapter 16
by
Cdslavejessie
Is Jamie sweet or vindictive to Dani as a sissy?
A bit of both
Jamie stared in shock at Danny, sprawled out with all his pretty lingerie blatantly on display. Danny’s legs spread wide open, heeled sneakers flat on the ground accentuating his calves and thigh muscles, back slightly propped up by the wall. He looked like a dirty truck stop slut in some degrading porno trying to entice her next John. Jamie stared, completely dumbfounded that his bully who relentlessly teased and bullied him for years for being a gay crossdressing faggot cocksucker (his words not Jamie’s) now was looking just like that!
“Uhhhh…. WOW! That is some outfit, Danny! When I first saw your panties in class, I thought you lost a bet with your frat brothers or something. Or even a little kinky play with your girlfriend Jessica. And I was gunna get a little bit of vengeance by making fun of you for it like you did me in high school. But… THIS… this is a lot more. Holy fuck, is that a chastity cage??” Jamie covered his mouth with his tiny feminine hand to suppress his giggle. Jamie knew all about chastity cages as a crossdresser himself. He owned a couple himself but typically only wore them when he was dating some dominant boy who liked the whole dom/sub thing. While it was hot, it was uncomfortable for him to wear it long term. But seeing his bully wearing a cage and seeing it through his basically sheer lace and silk pink panties, Jamie had to adjust himself from breaking his tuck, even in his super tiny daisy dukes.
Dannys brain was in shambles from humiliation and fear. He’d bullied Jamie forever for being a sissy twink, or so Danny and his friends thought that’s what Jamie was. Pushing him into lockers, humiliating him in front of the girls in class by claiming he knew he sucked the high school gay guys dick. Him and his buddies sneaking a girlfriend’s panties into his backpack and revealing it in lunch that “the sissy must have stole them to wear. What a sissy faggot hahaha.” And here he was, looking like a flaming poof waiting to get dicked down in a public toilet.
Jamie just continued to shake his head looking Danny up and down. While shocked and, to be honest, delighted that his bully was dressed like one of the sissies he sees on Reddit in those humiliation subreddits, Jamie started to realize something. Danny was wearing a full set of lingerie, cage, and heeled sneakers to an exam. It seemed like he purposely left off a belt so he’d be at risk of being caught. And Danny had always been a pretty boy with a big ass in highschool, it looked like he had seriously been working on his glutes and legs and purposely neglecting his upper body to be as slim and feminine as possible.
It clicked with Jamie that Danny was actually a sissy like him! That’s why he had been so cruel to Jamie all those years, he was repressing his inner girl and trying to fit in with all his macho jock friends. Sympathy flowed through Jamie, realizing that Danny had the same tormented brain that Jamie had growing up. And those thoughts finally got better once Jamie accepted that he was a feminine sissy girl. Sure, being a “sissy” was a kink thing, he wasn’t trying to **** what trans women and other non-binary people go through, but being a sissy was a part of Jamie. A sissy was different than a crossdresser or trans woman in Jamie’s eyes, as he’s sure people view it differently. It was a lifestyle choice for sure, but focused on hyper feminity and girliness. And also the want, no need, to be desired for that hyper femininity by women and men alike. To be owned and used for other people’s pleasure. Maybe it was because of Danny and his buddies constant bullying that made him a sissy, or more likely they just drew what was natural to him, but Jamie had accepted it and embraced it. And at that moment, Jamie knew that Danny was like him. And he was gunna help Danny embrace that aspect. Jamie’s smile turned warm and accepting, with still that look of lust in his eyes.
“Come on Danny, let me help you up so I can get a better look at this new you.” Jamie held out a small hairless hand, nails topped with oval acrylics 1/2 long painted a powder blue. Danny took the effeminate hand, still in shock at this turn of events and lifted himself off the ground. He tried pulling his pants up and pulling his shirt down, but Jamie stopped him. “Nuh uh, girl. I’ve already looked at your pretty undies, now I want to see that whole shebang. Hold on, let me lock the door.” Jamie pranced over to the bathroom door, wiggling his tight butt naturally, and locked it behind him.
Turning around, Jamie looked at Danny. He was so used to seeing the Danny from highschool. He was always a pretty boy, but Cocky and full of himself. Always dressing masculine and an easy confident smile on his face. Now, Danny looked completely different. His shirt was still stuck halfway up his chest, displaying his hourglass figure from his pink corset and just the hint of his lacy pink bra showing a slight swelling in the cups. His pants around his ankles displayed the lacy pink boy shorts with a silk gusset. The gusset had a significant wet spot and the unmistakable impression of a pink chastity cage showed through. His thick thighs and calves encased in semi-sheer pink stockings smoothed out any of the minor imperfections and his legs glowed in the fluorescent lights of the bathroom. Danny was always so confident, but now his hands were clasped demurely at his crotch, doing his best to cover his wet cage. His knees were turned inward as well as his toes in a stereotypical shy girl pose. Jamie couldn’t get over how fucking HOT Danny’s body looked and was more than a little jealous. He couldn’t wait to see how he looked completely as a girl!
“Alright, Danny, or should I say Danielle? Your outfit choice is fucking HOT girl, but those pants and that top do not match. I want to see the whole picture honey. Now, STRIP.” Jamie ordered. He wasn’t used to giving orders as a sissy herself, but something about this shy little sissy in front of her brought it out of him. And that it was her old tormentor was icing on the cake. And he knew that this is what sissies craved, being told what to do, so she assumed it would be right up Danny’s wheel house.
“Fuck fuck fuck!! Holy shit what is this guy… girl… whatever gunna make me do?? This is humiliating, I’m dressed like this flamer does!” Danny thought. He couldn’t just say no and run out. Jamie was in front of the door and it was locked. He couldn’t yell for help cause then more people would see his girly lingerie! He had to do what Jamie said and get through this. It was turning into yesterday with Jessica all over again!
Danny slowly stepped out of the jeans pooled around his ankles. He carefully stepped in his heeled sneakers, not wanting to trip and fall on his plug again. He looked up at Jamie’s eyes that were sparkling with delight as he grabbed the bottom of his polo and pulled it over his head. His corset and bra now fully on display. His small breasts protruding a little bit beyond the ribbed top of his corset, delightfully covered in the sheer pink lace of his bralette. His nipples poked out obscenely, either from the cold from the A/C, the fear of being in this humiliating predicament, and also the horniness cause by the plug and the silky smooth feeling of his lingerie, or from a combination of all three.
“Oh. My. God. Danielle that lingerie is AMAZING! And you fill it out so well! Those aren’t falsies in your bra are they?? They’re small but looks like at least A cups! Are you on HRT?? Omg turn around, I have to see that ass!” Jamie grabbed him by the shoulders And turned him around. The quick movement made Danny topple a bit and he grabbed onto the stall door for support. Bent over slightly grabbing the top of the door frame, Danny stood with his ass protruding. He had spread his legs to regain his balance and with his legs spread and back arched, he looked like a stripper posing on stage.
“Holy fuck that ass is ridiculous! You always had a cute ass but damnnnn you’ve been putting work in honey! I’m super jealous, I’ve only got a little peach to work with. Yours looks like you can twerk with the best of them!” Jamie lightly spanked Danny’s right cheek, causing Danny to stifle a moan when it shifted his plug, and watched it jiggle for a few seconds after. “Omg it’s like it has a life of its own! Fuck i can’t imagine how it shakes when a hot stud is taking you from behind. Your ass probably gobbles it up like a hungry hungry hippo hahahaha”
Danny turned back around biting his lower lip in shame. “It’s… not that big. And it’s not girly!” Danny pouted.
“Oh Danielle, don’t be so hard on yourself! You worked your butt off lol and it shows. Your ass is super feminine and I’m sure the boys like it.”
“I don’t want boys to like…” Danny was interrupted by Jamie gasping looking down at his crotch.
“Did you leak in your cage?? Omg that’s precious! Hahaha I totally get it, getting seen and admired in your sexy lingerie can make your clitty all leaky! I know I leak in a cage when a man is eyeing me like a piece of meat. Let’s see what kind of cage you have” Jamie pulled down the front of his panties exposing his cage. “Ohhh it’s soooo cute!!! Pink cages are the best! Oh but this one fully covers your little clit, no exposed holes or anything. Not the best for long term wear sissy. Don’t worry I’ll help you pick out a new one! And look how wet the tip is! And that puddle in your panties! *gasp* that’s a lot of precum honey you’re all sorts of worked up aren’t you!” A wicked idea hit Jamie at that moment. Jamie took her nailed finger tip and scooped up a bit and held it to Danny’s face. “Now, be a good girl and get a taste. I know it’s not as good as a real mans cum, but I’m sure you’ll love it sweetie, if you haven’t eaten it before already.”
Danny couldn’t believe what he was hearing. He stared wide eyed with fear at the slimy finger tip in his face. The powder blue acrylic shined in the light covered in Danny’s own lube. Danny opened his mouth to tell Jamie to get the fuck away from him. Jamie took advantage of the open mouth, not letting Danny back out, and shoved his finger in. Jamie knew that sometimes a sissy might balk at a new challenge, but from his own experience a push was needed to reach new heights. So Jamie was gunna push sissy Danielle to the height of femininity.
Danny felt the soft finger enter his mouth. The long tipped nail slight scratching at his tongue. Involuntarily, Danny closed his mouth and wrapped his plump lips around the digit. Jamie gasped in delight and slowly pumped her finger in and out a few times, making sure to get all that tasty pre cum inside the sissy’s mouth. Satisfied, Jamie pulled his finger out with a slight pop and gave Danny a cute smile.
“See, that wasn’t so bad now was it? And looking at you sucking on it like a slut! What was it you called me? A little faggot cock sucker? Well if that little taste didn’t show me , it sure seems like your lips were made for cocksucking haha”
Danny couldn’t take it anymore. Tears started welling up in his eyes and he bunched his fists. He couldn’t take anymore humiliation, any more being called a fairy, any more gay stuff, any more panties or corsets or heels or dresses or bunny suits. “Now listen here, Jamie or Jasmine or whatever you’re calling yourself now! I’m not like you! I’m not a sissy. I’m not a crossdresser. And I’m definitely not a faggot like you!” Jamie practically shouted the last part and stood there, breathing as heavily as he could in his corset, glaring at Jamie.
Jamie, initially shocked by the outburst since he was so submissive and demure a second ago, just smiled at Danny. Reaching into his back pocket, Jamie pulled out his phone and started recording Danny in his slutty lingerie “Oh really, Danny Stewart, what did you say? You’re not a crossdresser but you’re in such sexy lingerie. You’re not a sissy but you have such a cute little cage on that little dicklet of yours. And what was that last part? You’re not a faggot like me? Well, the way you sucked on my cum soaked finger begs to differ. And your cage is still twitching and leaking from trying to get hard. Well, how’s the saying go? If it walks like a duck and talks like a duck, it’s probably a duck. Now, you’re gunna get on your knees and apologize to Miss Jasmine, or else…. Well from the video I’m taking I’m guessing you can figure that out”
Danny fucked up. Royally fucked up. And there’s nothing he could do to get out of it besides follow Jamie’s, jasmines, orders. Reluctantly, Danny knelt down onto the cold tile of the bathroom, ass resting on the back of his heels, and started to beg.
“P-please Miss Jasmine. I’m sorry. I was angry and I acted out. Please don’t send that to anyone please!”
Jamie took a step forward, fully embracing her new roll as Miss Jasmine, and brought the camera up to Jamie’s face. Jamie took his fingers under Danny’s chin and tilted his head up to look at him “No, not good enough sissy. Give me your best girl voice and really beg and make me believe you really want to be a sissy girl for Miss Jasmine. And it better be good, bitch.”
Jasmine stood over the kneeling sissy as he clasped his hands together and looked up with pleading eyes. “M-Miss Jasmine please forgive me! I am a sissy girl! I love wearing cute lingerie and panties! I lo-…love having my…. Clit locked up in its c-cage. Thank you for fe-feeding me my own… cum” Danny said in his little girly voice, his shame spreading across his cheeks as he realized what he said.
“Good girl, sissy Danielle. I know it’s hard to accept your place as a sissy, but now Miss Jasmine is here to help. Now, one last thing to do to show you really want to be a sissy…” Jasmine turned around and unbuttoned her little Jean shorts and lowered them a little. She reached inside to her powder blue lace thong and adjusted things. With a sigh of relief, she turned to the sissy.
Danny’s mouth opened in a wide O as he looked at what was in Jasmines panties. A cock. Not just any cock, but a big one. It was already larger than Danny’s when hard and it was still soft! And as he looked at his with his wide open mouth, it started to get larger in his lace prison. Before too long, it was fully hard pointing straight up. It’s circumcised head poking out of the lacy blue panties. At least 8 inches, if not 9 inches of hard steel covered in feminine lace.
“Now, apologize again and finish by planting a big kiss on Miss Jasmines cock, sissy”
What does Danny do with the femboy cock?
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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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