Masculinity Lost Ch. 17-18

Hi guys and gurls!!! Thank you so so much for the love! i really appreciate you guys loving this story! Ive been reading feminization stories for years and felt like i needed to contribute. Im so so glad youre enjoying it! Please let me know what you think! i love love love reading all your comments so much it makes it all worth it!

Anyway heres the next chapters of Dannys rabbit hole!

xoxoxo Jessica

Chapter 17:

Danny stared at the big white cock in front of his face. Covered in powder blue lace from Jasmine's panties, the cock was a perfect duality. Both incredibly masculine and feminine at the same time. He could see a drop of precum forming on the tip and his revulsion from what he was about to do was all he could think about.

Jamie, now Jasmine in her dominant demeanor, pointed her phone camera down at the pink clothed sissy kneeling down on the bathroom floor. "Now apologize to Miss Jasmine for being a bad sissy and beg her to make you the prettiest little gay sissy possible. And make sure to end it with a big kiss on Miss Jasmine's girl cock" Jasmine slightly lowered her panties even more, letting loose the whole 9 inch shaft while her heavy balls were still covered in powder blue lace.

Danny sighed, trying to psych himself up for this demeaning moment. "Come on Danny. Just get through this. You can do it. He looks like a girl so just think of her as a girl. It's just a girl... with a big fucking cock. Damnit why did he have to be so much bigger than me??"

"Miss Jasmine. Sissy Danielle is so sorry for not being a good sissy. I want to be the prettiest sissy girl in the whole world. Please help me to become the sexiest... girliest.... Sluttiest.... *gulp* GAY sissy possible" Danny femininely begged the femboy standing in front of him.

Danny pursed his lips and started leaning forward to plant his lips onto Jasmines rock hard phallus. He closed his eyes shut as he leaned. Slowly, his big lips approached the throbbing cock. Hesitating an inch before contact, Danny finally made the decision and closed the gap. His thick lips planted on the head of Jasmines thick cock as Jasmines phone captured every glorious moment.

The bead of precum leaking from the tip slipped between Danny's lips and Danny finally tasted another man for the first time. "Holy shit, I'm kissing another man's cock! What is that taste in my mouth!!?? Wtf wtf wtf!" Ran through Danny's head.

Panicking at his first moment of "willing" homosexuality, Danny tried to pull back. He'd done the deed, he had kissed Jasmines dick. But as he tried to pull away, his knee slipped. Danny fell forward rather than away from the throbbing member. His lips, slick with precum, opened and Jasmine's girl cock started to slip into Danny's wet mouth.

In slow motion, Danny's eyes opened, looking up at Jasmine holding her phone to capture the moment. The dick slid further and further into Danny's mouth. Gravity causing it to reach the back of his throat, and continuing deep into Danny's throat. Danny raised his hands up to stop himself on Jasmines thighs, but it was too late.

Danny felt his nose make contact with Jasmines pubic bone. He looked up again, tears welling in his eyes at the sudden intrusion and saw Jasmine gasp in pleasure seeing Danny deep throat her 9 inch cock in one motion. The practice on "Daddy" last night must have opened up Danny's throat, suppressing his gag reflex.

Danny felt every inch of Jasmines cock, from his lips down his tongue all the way to his esophagus. All the veins and ridges were gripped by Danny's unwilling throat. With a final push, Danny disengaged the cock from his mouth, feeling all of the cock on the way out. With a loud pop, the cock left the sissy, dripping with saliva. Danny, now gasping at the intrusion, was lost in his own thoughts.

"Holy fuck I just deep throated a cock! I'm a cocksucker, FOREVER! Omg omg omg!" Danny panicked when he felt a wet slap on his cheek. And then another on the other cheek. Back and forth he felt them. Opening his eyes, he saw the glistening member in his peripheral before Jasmine swung her hips and another wet THWACK sounded on Danny's cheek. He was being cock slapped!

"Oh wow, sissy! I just said a kiss, not a full on deep throat! You must be really hungry for some cock huh?? Don't worry, there will be plenty more where this came from, bitch. Now thank me for allowing you to worship my dick and cockslapping your slut face" Jasmine ordered.

Jasmine didn't realize Danny slipped, he thought Danny willingly deepthroated her cock, only cementing the thought more that Danny really wanted to be a sissy. And humiliating acts like a cock slap is exactly what Jasmine would want, so of course Danny would too.

With tears in his eyes, not just from the lack of oxygen, Danny's eyes pleaded with Jasmine. "Miss Jasmine, t-thank you for f-feeding me your c-cock. And thank you for... *sob* cockslapping me"

Turning off the recording and then sending the video to her email, Jasmine addressed the pathetic sissy before her. "Good bitch. You know this is what you wanted so I'm glad you can accept it. Now get up. You made a big step just now by taking my cock. I'm very proud of you, girlie" Now Jamie, grabbed Danny's hands and carefully helped him up onto his heeled feet before wrapping him in a hug.

All the humiliation and degradation of before slightly melted away when Danny was hugged. Visually, he was being hugged by a pretty girl, giving him warmth and compassion. Lost in the moment, Danny melted into the hug and wrapped his arms around the shorter sissy girl. The moment didn't last long as rhe feeling of rhe 9 inch member resting on his leg destroyed the image of the pretty girl.

"Now Danielle, let's get out of this bathroom and get out of here. I think we have a lot to catch up on. But there's no way I'm letting you leave in those icky boy clothes. I think I have something in my bag that will work for you." Jamie opened his back pack and started rifling through it. Pulling out some tiny pieces of fabric with a dramatic "ta-da" Jamie held out Danny's new outfits. "Since you went above and beyond with sucking my girl dick, I'll let you choose your outfit sweetie"

Jamie held up two different outfits, each oozing femininity in their own way. First was a clearly gym outfit that left nothing to the imagination. A Barbie pink sports bra with a strappy back that left most of the back exposed. The sports bra cups with heavily padded, with the cups sticking out stiffly on their own. Pair with a pair of black work out shorts with a ruched back, designed so that the fabric has seam that goes up your butt crack to lift and accentuate your peach. On Jamie and his perky butt they would look great, but on Danny with his big butt and wide hips they be obscene!

The other outfit was less revealing, but oozing femininity. A white cotton skater skirt that hung to mid thigh. It was loose and flowy, but Danny knew that was a trap from his time wearing a similar skirt last night. Bending over or a gust of wind could show off his panties at any moment. Paired with a hot pink tank top that had "Barbie" across the front with thin should straps and very low cut. Finally, a blue denim jacket that was cropped short, very stylish with girls Danny's age.

"The gym bunny outfit is soooo sexy! Revealing nothing but everything at the same time! You'll look so hot in it with your sexy girlie body, Danielle! I know you've worked hard on it so I think it's time you showed it off. You'll have to take off your corset and stockings of course for this one, which I'm sure you'll hate not wearing the corset to keep your training regime up. And you'll have to be careful with your cage. You won't be able to tuck so maybe just hold your purse in front of you, unless you want to show off your little caged clit of course! Hahaha I know, sissies like us like to show off."

"Or, this suuuuppeerrr cute Barbie girl outfit. You can keep your stockings and corset on for this one. The stockings will match perfectly with the Barbie tank and make your legs look super yummy with your little skirt bouncing as you walk. It is a really cute outfit, but I think with your ass and those stockings You'll be sure to catch a lot of eyes. What do you say, sissy girl?"

Chapter 18:

"Miss Jasmine, can I please wear the.... Ugh gym bunny outfit?" Danny reluctantly asked Jamie. He knew the outfit would be revealing, but it (hopefully) wouldn't be too different than his normal gym attire of a tank top and shorts. It would just be showing a little more skin, well.... ALOT more skin, but Danny thought he could manage.

Just looking at the over the top girly Barbie outfit was too much. At least the gym attire was made for working out, something Danny attributed to masculinity and alpha-ness. The Barbie girl outfit was solely for looking..... cute! No way Danny wanted to look cute at all! Plus, he'd have to wear the waist trainer with it and he'd give anything to get this thing off and take a deep breath for once.

"Oh yippeeee! I'm so glad you chose that one! Now we can go to the gym together and you can show me how you got that big fat butt" Jamie squealed as she spanked Danny's panties bottom watching it wiggle wiggle wiggle.

Danny blanched at the thought of working out in such revealing outfit! He remembered just yesterday getting hit on in his boy clothes! If he showed up in these booty shorts and push up sports bra, he didn't know what would happen!!

"Oh fuck, John asked me out on a date tomorrow! And I texted him I'll be there. Jamie or Jessica CANNOT find out about that! Fuck, Demarcus wanted to take me out tonight! I gotta stay away from him and the apartment until I can get changed into my normal clothes. And I gotta stay away from Jessica today cause she knows! Fuck how did I get two dates with men??"

Danny wrestled with his new conundrum as He felt Jamie fiddling with the knots on his corset. "Um, Danielle, how did you do this yourself??" Jamie asked quizzically.

"What do you mean?"

"Well for one, this is tightened very tight and knotted behind you with no slack. I know I struggle with that with my own corsets so unless you're an acrobat, I'd say someone tightened this for you. But more importantly, the laces are locked"

Danny froze. "LOCKED??"

"And there's the answer to if you tightened it yourself. Yeah bitch it's locked with a heart shaped lock. Super cute I might add. So tell me.... Who has the key?"

Danny stumbled with his words, coming to grips with not only that he was locked in his waist trainer, but that Jamie knew that someone else was doing this to him. Maybe telling Jamie he was being blackmailed and wasn't actually a sissy would give him leniency and Jamie would help him get out of this shitty situation. Sure Danny was terrible to Jamie for years, but he couldn't imagine Jamie would allow him to be blackmailed into all this!

"It was Jessica, Miss! My ex-girlfriend! She lured me over to her place last night to talk about the Halloween party and next thing I knew I was in a bunny costume! She took pictures and everything and blackmailed me into all this! And she... she.... She....." The words tumbled out of Danny's mouth, hoping that Jamie would help Danny.

But he was just about to tell Jamie about the other.... Stuff Jessica had done to him, he stumbled over his words. He shuddered thinking about sucking "Daddy" and the memory of the feeling that the vibrator left as he watched a sissy getting dicked down.

"Ok ok ok! Calm down Danielle! Jessica Barlow? The rich girl in Kappa Gamma Alpha?" Jamie knew Jessica pretty well. When Jamie finally came to grips with his sissy hood and started presenting as, at a minimum a femboy, he had a few classes with her.

She asked Jamie one time where he got his cute teal corset tank top and became pretty good school friends from then on. She was a sweet girl, very smart and driven, but very friendly nonetheless. While she was definitely an "alpha bitch" she couldn't see Jessica doing this to Danny.

"Yes! That Jessica Barlow! After last night she came to my apartment and made me wear this.... Lingerie! She told me if I didn't then she would tell everyone that I... that I... umm... am a sissy. She didn't tell me she put a lock on the corset though!" Danny hung his head in shame thinking of how pathetic he sounded, hoping that Jamie would believe him.

It sounded far fetched to Jamie. Looking at Danny, he.... Well he looked way more like a she and that doesn't happen overnight. Jamie was naturally feminine but it took years to get his body looking the way it did. There's no way Danny did this overnight. But the tightened laces and lock on the corset said that someone else was involved. "Mhmm ... ok Dani. I know Jessica. Let me talk to her. You stay here while I call her." Jamie unlocked the bathroom and stepped out with his phone to his ear.

Danny stood in the bathroom alone in only his pink lingerie and high heeled sneakers. He realized how vulnerable he was and went to cover himself up with his boy clothes but realized they were gone.

"Fuck, Jamie must have taken them with him." Stuck in just his slutty lingerie, Danny needed to cover himself up somewhat. Faced with either the girly Barbie outfit or the tight gym outfit, Danny stuck to his original decision and decided the gym outfit was better than nothing. The girly girl skirt and stockings was too much for Danny. At least the gym outfit somewhat resembled what he wore himself to the gym, although much more revealing and slutty.

Danny stepped out of his heeled sneakers and unclipped the silky pink stockings. Running them down his smooth shiny legs, Danny shuddered and his dick twitched in its cage. "Fuckkk why do stockings feel so good! Maybe that part isn't so bad..." Danny thought and he slid them off his feet.

Next, Danny struggled to unclasp the bralette and was finally able to wrestle himself out of it. His naked nipples were pointing straight out and he grazed across them. A euphoric feeling rushed across his nipples and deep inside him as he brushed them, causing him to bite him plump bottom lip. "It's gotta be the cold and the nerves of the moment." Danny consoled himself.

Danny grabbed the padded push up sports bra and sighed as he held it in front of himself in the mirror. "It's just like a tank top, Danny. Come on man you can do this" Danny lifted the feminine garment over his head and shimmied himself in. Fiddling with the cups so they fit over his small chest, Danny saw that his cleavage was back. The push up effect of the padding lifted his flesh into a dramatic change, looking again like he had a C-cup. It seemed like the padding was gel silicone rather than just cloth, so the bra felt heavy on his chest.

The mounds of flesh looked massive to Danny as he looked down. The low cut top showed off a generous amount of cleavage. Danny turned in the mirror and fixed the four thin straps that crisscrossed his back. The straps went from one shoulder diagonally across his back to just below his shoulder blade where they connected with the front cups underneath his arm pit. With no strap straight across his back, he didn't think this sports bra would provide too much support to his new chest.

Testing it, he bounced up and down in the mirror and was shocked to his his chest jiggle and bounce up and down as he did. "How could a girl even work out in this? I guess it wasn't really designed for work outs, more to be ogled" Danny thought as he cupped his new breasts.

Danny then grabbed the tiny black booty shorts. "I don't know if these are even gunna fit" staring at them quizzically. Danny started to step into the shorts, one foot and then another bent over at the waist to lift the tiny fabric. Before he was even half way up his thighs, he heard the door open behind him. "Shit, why didn't I lock the door????" Danny thought as he looked over his shoulder.

Jamie walked in putting her phone in her pocket and lit up in a smile seeing the little sissy. He was bent at the waist, pink bra straps crisscrossing his back, accentuating and revealing rather than covering his sexy back. The black booty shorts were tight across his thighs and his big peach covered in pink lace was framed deliciously. Jamie stared at the beautiful ass when he saw something buried within the crack of his ass. A shiny pink jewel! Danny was wearing a butt plug!

"Well well well, sissy Danielle. I love that you still went ahead and put on your little workout outfit. Thought you would have changed into your boy clothes since you're being 'blackmailed' to do this" Jamie mockingly used finger quotes saying blackmailed.

"You took my boy clothes and I didn't want someone to walk in with me in just lingerie. I thought at least this would be better...." Danny mumbled, clearly embarrassed that he willingly dressed up even more.

"Danielle, I didn't take your clothes there right there behind your bag." Danny looked and sure enough His polo and jeans were right there. "Now Danielle... Jessica and I had a nice little talk and I think I can help you"

Danny couldn't believe he missed his normal clothes, ashamed that now Jamie thought he was even more willing to dress like a girl. But his attention focused once she said she would help! "She must believe me now that she talked to Jessica! Maybe she can help me get those videos and pictures back so I can return to normal!" Danny smiled at the thought, looking like a happy girl to Jamie.

"Yeah I can definitely help you, Dani. Cause Jessica made it clear about your whoollleee situation." Danny was thrilled! Jessica must've explained how she tricked Danny into all this. Thank god! "Yeah she told me how you came to her last night and explained that you broke up with her cause you're actually a gay sissy girl and didn't want to hurt her anymore." Dannys smile wiped away and his jaw dropped.

"Yeah she said she totally understood and would love to help you become the real you! She showed me pictures of your super sexy bunny outfit. You fucking rock that outfit btw girlie! Your figure is killer in it! She told me you asked, no begged her, to lock up your little clit until you found a real man to hold the keys. She even sent me the videos. My GAWD! You sucking 'Daddy' was incredible! I don't even know if I could get that deep and I have a lot of experience. And how you came like a bitch having your pussy vibrated! Oh em gee! A sissy gasm is an incredible experience honey. I almost came in my panties watching it!"

Danny's shame couldn't get any worse. He wanted a hole to swallow him up where he stood. Jamie, the target of his bullying for years, saw him suck a big black dildo and cum from getting his ass toyed, all while wearing a pink bunny costume. His blushing couldn't get more red, or so he thought.

"And Jess told me how you begged her to hold onto those videos and pictures to keep you in line. How you were afraid that your Danny self would try to change you back into being a boy. I get it honey, we all go through those 'sissy purge' episodes. Smart for you to take it out of your hands. And don't worry, sweetie. I'll be sure to hold onto our videos, just in case you try to get all macho again. Now, I'm sure this is one of those episodes, all that BS on how you don't want this. Well don't worry honey, I'll make sure to knock the man out of you and leave only a girly. Little. Sissy. Bitch." Jamie had stepped close to Danny at this point and wrapped her arms around his big ass. She punctuated her last words with slaps on his jiggly cheeks.

"Now, let's finish getting dressed honey. But those panties just won't do with those shorts. Here, I have a work out thong for you so you won't have panty lines." Jamie turned and grabbed a pink microfiber thong and handed it to Danny.

Danny was stuck. There goes his chance for help. And now he had another blackmailer set on making him as girly as possible. Danny shuddered wondering what the rest of the day would bring at the hands of his bully victim.