Masculinity Lost Ch. 09-10

Hi Guys and Girls and Gurls!

Omg! Thank you all so much for reading my story! It makes my day every comment I see people talking about my little fantasy story, good or bad comments! Please let me know what you think i truly appreciate you all!

Now lets see what befalls poor sissy Dani next!

Xoxo Jessica

Chapter 9: Dani learns to suck.... On camera!

Jessica paused recording the video "what's the matter, sissy? I told you you would pay for trying to get out of having your cute little butt plugged! Well, this is your payment!"

"No, this.... This is too far! I can't suck.... THAT! I'm not gay! We're stopping this now! I'm getting out of these clothes and out of here.... *WHACK*" Danny finally grew a backbone, seeing the black bone in front of him. There was no way he could suck that monster, and no way actual dicks could be that big. When he was about to turn around, he felt a solid whack against his cheek. Danny held his gloved hand to his cheek and looked up at Jessica. She had cock slapped him with the dildo!!! "I just got cock slapped!" Danny thought, horrified.

"Stop it right there, missy! You ain't going anywhere. Did you forget what happens if you disobey me? The pictures and videos go everywhere! That little snippet you just said about how much of a gay sissy slut you are will be hard to discredit, sissy girl. And, if you're just going to leave, sure you can get out of those clothes and wash away the make up, but those heels are locked on and I have the only key"

Jessica dangled the keys in front of him. "If you don't suck it, I'll hold you down over my knee and spank your ass with this black cock before shoving it up your sissy ass. So, turn the fuck around and get ready to suck some big. BLACK. DICK. Bitch!"

Danny was stuck. Jess had his clothes for one so he would have to trek back across campus in this skimpy outfit. Even if he stripped of his clothes, those heels were locked to his feet. Sure he could cut the locks but he'd need to get back to his apartment first. But more so he was terrified of that big, veiny black cock going into his ass. A tiny voice in his head said "that plug felt amazing. What would this feel like....?" but he quickly shut that voice down.

Danny reluctantly turned around and faced his tormentor. "Ok Miss. I'll do it. Just please let me go after this. Pleaseeee!"

"Oh Danni, you can go home after this. I promise" Jessica said with a wicked smile. "Now put a smile back on your face for the camera sissy!"

Danny put a fake girly smile on his face as she started recording again. "Ok Danni! You ready for your first taste of cock? Come strut your sexy ass over her and get on your knees for it" Jessica said as she put the dildo against he crotch like it was her own dick.

Danny shuddered at the thought of what he was going to do, but visibly it looked like he was shaking with excitement combined with the smile on his face. Danny took small mincing steps, rolling his hips due to the heels and plug combo, towards his ex girlfriend.

As he approached, Jessica stopped him "Even if you weren't smiling, I can see how happy your new image is making you! That is not a very feminine bulge in the front of your body suit, honey! Even though it is pretty small for a man, it works great for a sissy! And wow you move so much better now in your heels, girlie! What caused such a change in your gait? Turn around and show the camera your little "tail" girl!"

Completely ashamed and humiliated, Danny spun on his heel and bent slightly at the waist, poking out his satin covered ass and white fluffy cotton tail. "Oh come on sissy, shake those sweet cheeks! Gotta get your mans dick hard before you suck him off!" Danny shamefully started shaking and rolling his ass back and forth.

He was grinding it back and forth like a girl in the club, like he had had so many girls do to him. Suddenly, Danny felt a hand on his ass and he slowed down his twerking. Then, a thick pressure in his ass as he felt the plug being slowly pulled out, widening his sphincter as the plug pulled out slowly. She worked it in and on, never taking it fully out, cause Danny to squirm and moan as the feelings were too much for him to handle.

"Ooooooo our little sissy girl likes it! Danni was complaining to me that she just couldn't get her walk sexy enough and asked me what she could do. I knew that sticking a cute little plug up the bee-hind would give her the wiggle she was looking for. She begged me to plug her sissy pussy, didn't you Danni?" As Jessica asked her question, she pushed the plug home to its base, causing Danny to moan in mix of pain and pleasure.

"Eeeeeepp! Yesssss Miss!" The confirmation came involuntarily from him, as he covered his mouth with a gloved hand, humiliated he had admitted to wanting this infernal plug in his ass.

"Now that's good girl! Begging for your pussy to be filled. But before you can do that, you gotta get your man's cock ready! Turn around and on your knees sissy!" Danny turned around and knelt down before his ex, who was waving the 12 inch black cock in front of his face. "Now first, before you suck it, you gotta tease your man a bit. Tell him about how badly you want it while lightly stroking it up and down. Go on sissy girl you've wanted this for so long"

Danny, fighting back tears, hesitantly reached out with a pink gloved hand and circled the black phallus at the base, barely circling the cock with his hand. "It's just plastic and silicon. It's not real. You're ok, Danny. You can get through this. It's not real. It's not real. It's not real" Danny thought to himself.

He forced himself to bring his hand up towards the head, lightly stroking it. "I want to suck your.... C-cock." Danny whispered.

"Couldn't quite make that out, sissy. You gotta be louder and more descriptive" Jessica said.

Completely humiliated with a red blush filling his cheeks, Danny replied "oh yesssss. Please can I suck your cock?? It's so.... Big. And black. Can I p-please wrap my big pink lips around it?"

Jessica laughed loudly, "hahahahha that's better sissy girl. Go ahead and give it a kiss and then say "thank you, daddy!"

Quivering with fear, Danny puckered his shiny pink lips, plumped up from the plumping serum, and brought his head forward to the dildo. Eyes closed tightly, showing off his sparkly eyeshadow and big eyelashes, Danny lips connected with the silicone phallus. With a loud lips smack, Danny backed off. "T-thank you....d-daddy" Danny shamefully said with his newfound sweet girly voice.

"Oh that's so sweet. But Daddy needs more than a kiss. Now open those sweet lips of yours and let me show you how to work a cock bitch" Jessica took the dildo in one hand attached to her crotch as she swung it in front of her, slapping Danny's cheeks several times. Danny involuntarily tried to shrink down away from the blows. As his ass met his ankles, the plugged pushed further inside him causing him to open his mouth in a wide O of shock, eliciting another feminine moan.

That's all Jessica needed as she plunged forward with her fake member, filling the sissies mouth with black silicone. Dannys eyes flung open wide, the dildo so wide across that Danny's plump lips formed a tight seal around it.

"Oh what a sexy picture, Danni! Big black cocked wrapped in pink lips! Plenty of eye contact too. Guys love eye contact during a blow job. Let's see how you work this cock now" Jessica began humping Danny's face, not giving him the full 12 inches as the newbie couldn't handle it. Jess would pump to the back of the sissy's throat, causing a slight gag at each thrust.

*glug glurgh glug glurgh glug*

Danny could only take the face fucking, as his body was powerless to stop the unrelenting assault. He had his hands laying softly on Jessica's thighs, but the powerful sensations coursing through his body didn't let him push back, as much as his mind screamed at him to do so. The plug was fully seated, pressing into his prostate, and with each thrust turned the sissy boy on more and more. Plus, the lack of oxygen was causing an erotic, trance light state, as Danny maintained eye contact with Jessica but those eyes started to go cross and then roll up with each thrust.

"That's it my little sissy! You're such a good little cocksucker. Isn't this what you always wanted, sissy fag? No wonder you couldn't keep it up for me when we were dating. All you wanted was a big cock inside you, isn't that right? Do you want more cock sissy girl? See how far you can go down on this BBC?" Jessica teased Danny mercilessly as she pulled the cock from his mouth so he could answer, and cock slapped the sissy a few times for good measure.

Danny wanted to say stop. To say no please! No more! But all that came out as he submissively looked up at Jessica's face, and the camera was "Please...*gasp* Miss"

"Alright, since you asked for it. Open wide bitch" Jess set the camera off to the side as she grabbed Danny's pony tail and brought the cock to his mouth. Slowly but surely she entered the sissy's pink mouth, inch after inch. She hit the back of Danny's throat but kept pushing with little thrusts.

Danny gagged and glucked and gurked, doing his best to suppress his gag relex, completely accepting what was going to happen to him. Finally, Jessica broke through and entered his throat, eliciting a low moan from Danny as the cock got deeper and deeper down. When Danny was almost out of air, he felt his nose hit Jessica's pubic bone, and his chin touching the silicone balls.

"Gooooood sissy! I can't even deep throat this monster! What a slut you are, sissy!" She exclaimed as she pulled out of the sissy's throat with a loud squelch. Danny collapsed to the ground, ass high in the air, gasping for breath.

"You did good sissy princess. Say good night to all your followers!" Danny looked up as Jessica held the camera to his make up smeared face, saliva and tears smearing the artwork Jessica created.

Chapter 10: She lets him go, but not without a gift.

Danny just hung his head shamefully in disbelief at what he had just done. He had just sucked a big black dildo on camera! Not just sucked, but deep throated it like some slut! And his ex, Jessica, made it seem like he wanted all this. To be made up like some slutty coed looking for dick, and finding it! He had to get out of this. Delete the photos and videos and reclaim his life back. He just had to get home first and out of these clothes.

"Danni that was so good! You really showed how desperate you are for cock! I can't even deep throat that monster and believe me I've had a lot of practice, with the real thing as well. Now since you were such a good girl, I'm gunna let you go home for the night. Unless of course you want to stay here and we can see what "Daddy" does to the tight little asshole of yours?"

Danny desperately shook his head no "please no Miss. please don't put... d-daddy inside my ass"

"Hahaha no no not tonight. We gotta stretch that pussy out first. Now, I'm gunna put together a little goodie bag of girly stuff so we can start your new life as sissy Danni."

"What do you mean, Miss?" Danny made sure to call her Miss so no more punishment would be inflicted tonight. "Aren't you letting me go?"

"Oh you sweet little bimbo. I'm letting you go home tonight, but that doesn't mean our games are done! No no no, sissy Danni is so much more fun that frat jock Danny *blegh*. And I'm gunna make sure she is here to stay. Now, I already have so many cute and sexy pics and videos of you prancing around as a cute little sissy girl, showing off your hard clitty and your sexy "bunny tail". Also of course your unveiling as a throat GOAT! Be proud of your skills, girl! lol. But just as added insurance, I'm gunna make sure that little clitty doesn't bother you by showing up at unwanted times, like dates with cute boys! Now lay back on the bed or I'll shove "Daddy" in dry!"

Danny, fearful of what she meant by what she meant with his "little clitty", was even more fearful of what Daddy would do to his ass. He scrambled onto the bed, subconsciously keeping his legs together to protect his modesty.

"Now close your eyes, sissy girl, this is the fun part" Danny closed his eyes and felt Jessica pull his ass to the edge of the bed. He got fearful she was gunna make her threat a reality as she pulled his plug out, but it was quickly replaced with a slimmer toy, much smaller than "Daddy". As it entered a few inches and pressed against his prostate, he heard her flip a switch and an intense vibration started. Danny let out a feminine moan and squirmed on the bed.

"Mmmmmm oooohhhhh fuck" Danny moaned.

"Hahaha oh yeah you love your pussy played with don't you? Welcome to the world of vibrators! Now open your eyes, sissy girl."

Danny opened his eyes and saw Jessica had her laptop on the bed next to him. On the screen was a big white jock, similar to a lot of Danny's frat bros, fucking a tiny little brunette girl. He had the girls ankles on his shoulders and was pounding his thick 8 inch cock inside her. Danny moaned and felt incredible lust, as all the erotic sensations from the evening combined with the intense vibrations on his prostate and the full feeling in his ass.

"That's right, Dani. Watch that girl get pounded by a big jacked guy. Look at her take him and stare at her man with lust in her eyes. Look at his strong, hard body flex with each thrust. Biceps and triceps straining. His butt flexing. His abs and pecs so hard and hot. His big cock slamming into her." Jessica said this and started rubbing Danny's cock, not stroking it but rubbing it like a girl does to her pussy.

"Now look at the girl. Her tight tanned body. Her beautiful make up. Her big long lashes, Smokey eye shadow begging her man to fuck her harder with her sexy eyes. Her lips biting between slutty moans. Her tits bouncing in her bra as she grabs and kneads them with her hands. Her stocking covered legs leading to her tall black stilletos. Look how beautiful she is as she takes her man into her."

Danny was so incredibly close as Jessica's words flowed over him. Her vibrator thrusting in and out of him. Danny drew his legs up, unconsciously mimicking the girl on the screens pose. He started grabbing at his full bra bringing more incredible feelings to his body. His ankles are now on his ex girlfriend's shoulders as she pounds his pussy with her vibrator, rubbing his cock, his clit, like a pussy. He was so close.

"Now look down between her legs, Danielle."

Danny looked at the screen and saw that the brunette on the screen had a cock! A small tiny cock that was covered in a pink plastic cage of some sort, but a cock nonetheless! Danny's eyes opened wide at the realization and at the same time Jessica turned up the vibrator. Danny stared at the screen as the gurl on screen screamed and thin, weak stream of cum came out of her cage.

Danny let out a similar scream as the feelings became too intense and he felt his 4 inch cock erupt into his satin thong. This orgasm didn't end quickly like it normally did. It came in waves. Each wave crashing into him, causing more cum to erupt from his satin encased cock. "Omg omg omg! Fuck fuck fuck! Fuck me fuck me fuck me! Unnnnggghhh!!!" Danny arched his back and finally collapsed onto the bed, completely spent.

Danny lay gasping for breath, hearing Jessica saying something but unable to comprehend it. He felt the body suit be unzipped and a cool damp cloth be wiped against his crotch and stomach. He felt her manipulating his dick and balls but was too exhausted to know what was going on. Finally, he heard a click, which brought him back to his senses.

"What a good girl, Danielle. I hope you enjoyed your clit being played with one last time. That won't happen for awhile. But, I'm sure you're glad you learned how much pleasure your sissy pussy can give you! Hahaha"

Danny sat up with a groan and looked down past his pink satin encased "tits". Between his stocking covered legs sat a pink cage, very similar to the one the brunette was wearing on screen. It was maybe an inch and half long with some breatheable holes on the side. Above it sat an internal lock that looked impossible to cut. Danny grabbed it and winced as he tried to tug it off but failed.

"Oh no, sissy. That's not coming off easy. And I have the only keys. Don't worry, I have a couple spares in case your boyfriends want to let you out" Jessica laughed as she jingled the keys in front of his face. "Added protection in case you think you can become a man again after tonight hahaha. Now I think it's time for you to go home. Do you want to stay in your Halloween costume, or do you want to wear something different??" Jessica asked with her signature evil smirk.

to be continued.