Masculinity Lost Ch. 15-16

Chapter 15: Danny goes to class and meets someone from his past

Danny walked out of his apartment building, holding onto the waist band of his jeans. The corset had compressed his waist so much that his jeans didn't fit at the waist anymore, they fell down to his wide hips. Surprisingly, the jeans still fit tight on his ass and thick thighs, giving a great look at his heart shaped peach.

But the jeans fell down so far that the bottom of his corset and top of his panties were clearly on display if he wasn't careful. He tried tugging down the blue polo he was wearing but it was too short to cover the gap. Danny was forced to hold onto his waistband and carefully walk.

With the combination of his careful walk, the heeled sneakers, and plug in his ass, Danny was practically mincing. He had had to take short steps and the plug was making him walk almost one foot in front of the other. His ass swayed and rolled side to side, giving off a sexy strut. Danny looked at his phone for the time and saw he really had to hustle to make it to his exam. He had thrown the purse in his backpack, not wanting to look more like a fairy than necessary, and carefully but quickly tottered through campus.

The walk through campus was somewhat uneventful. Danny only drew a couple odd looks from guys and girls alike, with Danny hoping it was cause he was holding up his pants, not walking like some sissy. There was one guy that was walking behind Danny and saw his ass wiggling and jiggling side to side and gave him a wolf whistle.

Danny turned his head to look at him and the guys confident smirk quickly turned to horror as he realized he'd just cat called a dude. He turned on his heel and high tailed it out of there as Danny stood there blushing with embarrassment that his ass had got him hit on AGAIN!

Finally Danny reached the lecture hall for his Econ final. Thankfully, Danny was doing alright in this class and somewhat knew what he was doing. His lack of studying yesterday hopefully wouldn't affect him too much. Danny walked to the back of the class, wanting to hide in the back, but saw the back row was full. He had to take a seat in the next row up and tried to sit carefully so his pink lingerie wouldn't show. As he was about to sit gingerly, his heeled sneaker slipped and he fell hard on his ass.

Unfortunately for Danny, his fall pushed his plug deep inside him, pushing right onto his prostate. Danny's eyes crossed and rolled back into his head from the combination of pain and immense pleasure. A quiet but decidedly feminine moan snuck out of Danny's mouth that he quickly tried to cover up with his manicured hand.

As the intense feeling passed, Danny looked around. Thankfully, it appeared no one noticed his feminine moan. But as Danny looked down at his lap, he saw a good sized wet spot on his jeans. "Omg, it made me leak through my pants!!!" Danny internally screamed to himself. He didn't think he fully came as his clit was trying its best to still get hard in its plastic prison and Danny was as horny as ever.

Trying to calm himself, Danny scooted his chair under the desk hoping no one would notice his precum stained pants. Forced to sit up straight from his corset and plug, Danny tried to adjust his clothes to make sure his lingerie wasn't showing. "God this is a nightmare! Please help me get through this class so I can get changed!" Danny prayed to himself. Just then, the professor let the class know to start the test.

Danny flipped through the test and started filling in the bubbles. He managed to get through most of them with little difficulty, but the constant reminder of what was under his clothes was eating at the back of his brain.

The tightness of his bra wrapped around his chest. The straps of the garters tight on his thighs. The constricting feeling of the corset forcing him to take shallow breaths. The silky feeling of the stockings sending electricity throughout him. The lace of his panties on his ass and plastic cage. And most of all the plug deep inside him. All working together to jumble Danny's boy brain into a haze of pink feminine pleasure and discomfort.

Danny worked through until his pencil broke. Sighing is exasperation, Danny bent forward in his chair to grab a new one from his bag. Realizing as he sat back up that his panties and corset were on display from his raised shirt, he quickly fumbled with it pulling it down sweating nervously and looking around, Danny only saw downturned heads working diligently on the exam.

Sighing in relief, Danny turned back to his exam when a pair of eyes caught him. Behind him sat a familiar face, one from his high school days. What was his name? Johnny? James? Jamie? Jamie! That was it. Danny and his jock buddies used to bully the little twink, calling him Jasmine the fairy.

The little guy was only 5'2" and maybe 120 lbs. Fair skinned and smooth androgynous, almost feminine face. An unfortunate look for a teenaged boy in public high school, especially when combined with his love for video games and anime stuff. And Danny and his buddies bullied that kid daily. It wasn't anything personal for Danny, he didn't dislike the kid, but when you're top dog and with your pack of alphas, the betas get bullied. That's just nature, in Danny's eyes.

But looking at Jamie now, he noticed his face was much more feminine than androgynous. Pretty almost. With long blonde hair down to his thin shoulders, covered with only the straps of a tank top, it seemed like Jamie had bought into his feminine look. Was that a hint of make up on Jamie's face?

Looked like his eyelashes were much longer than natural, his eyebrows arched more than a straight male would have his, his cheeks a touch more pink, and his lips had a shine to them. And those lips were curled in a devious smile as he locked eyes with Danny.

Flustered, Danny turned his blushing face back to the exam and quickly finished. Barely registering what he was answering, Danny stood up and carefully minced his way to the front to drop the exam with the TA. Not waiting for a response, Danny grabbed his back pack, hiked up his pants, and strutted out of the lecture hall.

Trying to walk as quickly as possible without falling, Danny made his way down the hall. He heard the lecture hall door open and close behind him and the sound of approaching footsteps. Not looking back, Danny turned to the restroom so he wouldn't have to deal with another person watching him wiggle his walk.

Danny entered a stall and locked the door behind him before sitting on the toilet seat, head in his hands worried that Jamie had saw his lingerie. His fear was raised higher as he heard the bathroom door open and footsteps walking in. A pair of white and pink sneakers stopped in front of his stall and Danny started to panic. A knock on the stall door brought an almost full freak out.

"Danny, is that you?" A soft mostly feminine voice called out. "Danny I know it's you, I recognize your sneakers, or should I say heels haha. Open up and let's chat, Danny boy"

Danny, scared shitless, sat terrified to move on the toilet seat. "Open up, Danny. I'll wait here all day for you and any moment someone can come in. If you come out I'll lock the door, ok?"

Danny, knowing he was caught, stood up and slowly unlocked the stall door. He cautiously opened the door to see Jamie standing in front of him. Jamie looked different than he did in high school. He saw his long blonde hair before but now saw it was cutely styled with cute bangs and curl to the hair. Now closer, Danny definitely saw make up on Jamie's face, accentuating Jamie's naturally feminine looks.

The thin strapped powder blue tank top was pretty low cut. Surprisingly, it looked like Jamie was wearing a bra and had some small cleavage. The tank top was cropped short, showing off Jamie's soft stomach and his belly button sported a pink belly button ring with a dangly heart hanging from it. His shorts were very very short, jean cut offs that left Jamie's tight little cheeks peeking out the bottom. And on his feet with the white and pink sneakers. While still barely androgynous, jamie was looking far more feminine. A lot would say pretty for a girl, especially for a boy.

"Soooo Danny. Long time no see. Well, for you to notice me at least. I've been in like 5 of your classes so far and, I guess thankfully you never noticed me. I was tired of all the bullying back in the day, but it seems like we might have a lot more in common than I thought, if that flash of pink was what I thought it was. So.... Are you really wearing panties right now?" Jamie took a step towards Danny, reaching for his waistband.

Danny, freaking out, tried to push Jamie's hand away with both of his. Unfortunately, that let his jeans slide down, showing off the top of his lacy pink boy shorts. Fumbling with himself, Danny pulled back up his jeans and looked back at Jamie with wide eyes.

While fumbling, Danny took a step back and tripped again in his unfamiliar heeled footwear. His feet kicked forward as he fell back, landing hard on his ass once again. His plug pushed deep into him again and Danny once again loudly moaned at the pain and pleasure, leaking even more into the silky gusset.

Danny, sprawled between the wall and the toilet, looked up at the pretty twink before him whose eyes opened wide in surprise and delight! Danny looked down and to his horror saw that his pants had fallen down to his knees, displaying his lace and silk panties, garters and stockings. His shirt had also ridden up, showing off his corsetted waist and the bottom of the lacy cups of his bra. Danny was now sprawled out in his sissy pink lingerie in front of his old bully victim!!!

Chapter 16: Jamie is a sweet bully

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 degrade 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.