Masculinity Lost Ch. 11-12

Chapter 11: He gets out of the costume, but not out of being a sissy

Danny was pissed. Seeing his pride and joy locked away like this was too much, even with all the punishment and humiliation and blackmail, he couldn't hold back his anger at his manhood being locked up.

Danny stood and tried to give off an intimidating presence by crossing his arms, shrugging his shoulders, and giving Jessica a mean look. But in his new feminine attire, he looked like a petulant brat, more adorable than intimidating. Crossing his arms just made his breasts more pronounced and his angry look came off as a sexy pout.

"Now listen here, Jessica. This is too far! I've followed all your orders for your little game tonight. All the demeaning shit you did to me *shudder* was horrible but I did it! This cage is too much. Now give me the key or else I'll...." Danny struggled to think of what he could do to her, as she held all the cards. He had no masculine clothes, she had the key to his locked dick, and most importantly all the blackmail material that would ruin his life forever.

"Or else what, sissy? You think you can go back to being masculine Danny again just by puffing out your chest? All that does is make your "girls" look bigger honey, which is a good look for you sweetie. You're going to wear that cage until I tell you to, and you're gunna be doing a lot more than just having your little clitty locked away. So fix your fucking attitude or I'll kick you out on your satin covered ass and post all this for everyone to see! Now say 'yes Miss I'm sorry I tried to be a man again. I'll be a good girl.'"

Jessica drew herself up and put a finger squarely in Danny's prominent chest and pushed him back. Danny, not expecting the sudden movement and still unfamiliar in his new heels, fell back onto the bed letting Jessica lord over him as he gazed up at her submissively.

Danny, shocked by her sudden anger, gulped and submissively whispered "Yes Miss. I'm sorry I tried to be a man again. I'll be a good girl and do whatever you say!"

"I was gunna be nice as you were such a good girl for "Daddy," and how far you fell into your new found girlhood that you came from your sissy button, that I was gunna let you get dressed in your ugly boy clothes, but this outburst ruined that. So you have two options. One, you leave in your sexy little bunny outfit and make your way home through a drunken college at night. Orrrrr.... I dress you like a normal college sorority girl. What do you say, sissy?"

There was no choice for Danny. There's no way he would be able to make it home like this on his own. He'd either be found out as a sissy and humiliated, or worse he'd be molested and taken advantage of cause they thought he was a real girl! Looking at the slutty bunny with her tits popping out of her corset in the mirror, the second option was more likely. He'd have to accept the lesser of two evils and let Jessica choose a new outfit for him.

"I'd... I'd like to change, Miss" Danny said submissively, hoping she would take it easy on him if he turned up the girliness.

"Good girl, that's what I thought. Alright then, little Miss Priss. What should we deck you out in" Jessica teased as she looked through her closet. "Aha! Perfect! Ok little sissy, let's get you looking like a college slut rather than a playboy bimbo hahaha"

Jessica untied and loosened the corset as Danny breathed in a sigh of relief, thrilled to be out of the constricting garment. She undid his garters and had him step out of the body suit. She took off the gloves and bunny ears and choker collar as well. Unlocking his pink stilletos, she had him take them off and took off his sulking pink stockings. The electric feel on his freshly denued legs made him shutter and bite his lip as his cock tried to get hard in his cage. "Fuck why does that feel so good! Stop it, Danny! You're a man, not some girly gay boy! Just get through this and get home!" Danny thought to himself.

Standing there in his matching pink thong and push up bra, Danny felt free from all the restricting clothes for the first time it felt like in forever. His feet ached from the sharply pointed pumps. His waist and chest finally felt free, but he could still feel how the corset had crushed him into an hourglass shape. Those feelings would go away, but the tightness of the cage around his cock remained, as well as the sore, slightly loose feeling from his backside.

The relief was short lived as Jessica returned with a pile of fabric in her arms. "Seeing your bombshell hour glass figure, I have to keep it going. And I know you love how it brings out all your curves! So arms up sissy!" Jessica teased as she wrapped a black underbust waist cincher around him. Danny moaned in displeasure, but kept his mouth shut not wanting to anger her once again. Danny grunted as Jessica tightened the laces one by one and let out a gasp of air as she put her knee into his back to really get it tight. Tying off the laces, Jessica was happy to see Dani's curves on display again, his waist being reduced to 28 inches!

"Good, even tighter waist than with your bunny costume! I think we can get even smaller with continued waist training. Let's get you into your cute outfit girlie!"

First she slid some thigh high white socks onto his smooth legs. While not as sensuous of a feeling as the silk stockings, they still caused a wriggle up his spine. Next was a black and white checkered pleated mini skirt, falling a few too many inches above the knee. The flouncy skirt would need to be handled carefully when he walked or he'd be showing his pink thong to everyone.

Next came a black long sleeved sweater tucked into the skirt. The top was extremely low cut and showed off his generously enhanced chest. Finally, for a splash of color she put back on the pink rounded closed toe stilleto pumps. With a final click she locked them tight onto his ankles. She put a simple fake gold chain necklace and some bangle bracelets as accessories. Finally, she put a pink head band on his head.

"All set, sweetie! Ugh you look so cute im so jealous of you girlie! Now, take this bag with you but don't open it until you get home. I'll be watching your walk of shame, slut so you better be a good girl! Oh, and I completely forgot! Can't have my girl walking without her signature wiggle now can we? Bend over sweet cheeks!"

Danny's cheeks became even more pink at the humiliation of being bent over again to get plugged, but with how exhausted he was, he couldn't put up any fight. So he simply bent over at the waist and rested on his elbows as Jessica flipped up his flirty little pleated skirt and pulled his pink thong to the side. With his asshole still lubed from his "fucking", Jessica began sliding in the plug. This time, even with all the stretching, it felt big, bigger than before. Danny's eyes began rolling back into his head, the same feelings of euphoria beginning to creep up on him. As his sphincter was reaching its breaking point, he felt his hole suck in past the widest point to the flanged base. With an eeep! Danny's hole was once again plugged.

"Thought you'd need to go up a size, sweet cheeks. You will not take that out until tomorrow morning, do you understand me?"

"Yes, Miss."

"Good girl, now get out of apartment, slut!" And with a sharp slap on the ass, like a common slut, Danny was pushed out the door.

Chapter 12: The walk home, Danny meets someone

Danny stood on Jessica's doorstep afraid to move. He had his black shoulder strap purse (his purse? Omg I have a purse!) clutched in both hands in front of his waist as his eyes darted around him looking for someone. He was terrified, looking for someone to call him out as a man in a skirt, but no one was around. He started to calm down, realizing he was alone in the night.

"Ok Danny. You got this. You're out of that lunatics apartment and free to go home! Sure, you're in a skirt, wearing a corset, with sky high pumps on your feet and an infernal butt plug up your ass, but you're free! Now get your ass moving and get home to get out of this shit"

Danny thought as he took his first steps towards home, hearing the click-clack of his heels on the pavement cause him to shudder again at his predicament.

The warm late spring air felt great on Danny's exposed skin. He was surprised how nice of a feeling the warm air felt flowing under his skirt. Danny scolded himself. The swinging of his loose mini skirt did feel nice on his exposed thighs. And the thigh high white socks still felt great on his glossy legs. Now that he was free from Jessica's wicked clutches, he could admit that some of the clothes felt.... Well good actually. And the plug, while making him feel very very full, was prodding at his prostate with each rotation of his hips.

"Stop it, Danny! You don't like wearing a skirt! This is the last time! Youre not gay, you're not gay, you're not gay!" Danny tried reminding himself as he felt his little member start to waken up in its cage.

Danny tried to make his way quickly through the darkened campus. Streetlights lining the paved walkways between the full green trees. At almost midnight on a Tuesday, the campus was basically empty, and Danny was very happy that was the case. He kept his eyes peeled, searching back and forth as his pony tail whipped from side to side looking for anyone coming up on him. But Danny was alone, only having the sensuous feeling of his girly clothes, the click clack of his heels, and his own thoughts questioning his reality to himself.

Danny came upon a cross street and was waiting for the signal as a car slowed to a stop behind him. "Shit shit shit. Come on keep going please!" Danny pleaded but saw the light turned red and the car stopped. Afraid to look, Danny kept his eyes down towards the ground not wanting to make eye contact.

"Hey! Hey girl! Whatcha up to tonight looking so good??" A masculine voice called out.

"Fuck. Fuck fuck fuck. No come on light turn please!" Danny thought. He tried to look surreptitiously at the car and driver. Hanging out the drivers side window and back window were two college boys. Fairly attractive in their own right (I'm not gay I don't find men attractive, Danny thought), both the brown haired white boys looked like any number of attractive college hunks on campus.

"Hey baby it's alright. We just wanted to see what you're doing tonight. If you want, let me get your number and we can meet up?"

Danny turned and looked at the boys, realizing the little sedan was packed full of college jocks. Each of their gaze was filled with lust as they hungrily looked up and down Danny's feminine body. From his pink stilettos up his white socked legs to his tiny pleated skirt, up his thin corseted waist, stopping for a long time on his enhanced chest, the horny boys undressed him with their eyes. Blushing at the shame of not just being undressed and ogled, but that they seemed to have no clue that Danny had a male appendage between his thick thighs. Before Danny could answer, or do anything else, the car behind the boys honked as the light turned green.

"Shit, alright girl well here's my number. Hit me up ok? Names Jason, cutie!" The driver said as he threw a piece of paper, hitting Danny right in the cleavage before bouncing to the ground behind him. Without thinking, Danny turned and bent over to pick up the paper.

Still stuck in his girly practice with Jessica, Danny bent at the waist, giving the boys a great look at the bottom of his pronounced butt cheeks under his skirt, the pink thong barely visible between his girly cheeks. Danny heard multiple whistles and a "daaaaammmmnnn that girl has an ASS!!!" Before another honk caused the boys to drive away.

The shame of what he'd just inadvertently done, showing off for that car full of boys, brought another flush to his cheeks. He snapped back up, holding his hand to his mouth as the reality of his slutty pose hit him. "Damnit, Danny! You're not some slut you're a man! Get it together!" Danny scolded himself again as he continued his trek home, unconsciously slipping the paper with the boys number on it in his purse.

Finally, his apartment was within eyesight and not a moment too soon. His feet were starting to ache from his slutty heels and the corset was really doing a number on his waist. But the plug was really getting to him. Each step forced the plug to run his prostate and he'd begun to leak through his cage. While unable to get hard, Danny was getting hornier and hornier by the minute. "Almost home Danny almost home!"

As he approached the front door of his complex, home almost within reach, he saw a man leaving. And not just any man, a large black man, none other than his roommate, Demarcus.

"Shit shit shit! No please no! Ok just walk away and wait for him to leave" Danny thought as he turned on his heel to do just that. But, still unaccustomed to his new feminine footwear, Danny turned to quickly and fell on his feminine rear. "Eeeep!" Danny femininely squeaked as he fell on to his butt. Before he could get up, a large black hand was in his face.

"Woah girl! Watch yourself on those stilts! Here let me help you shawty" Demarcus low masculine voice rumbled as he grabbed Danny's hand. Looking at the stark contrast between the two hands, one black and massive, the other white and dainty looking, Danny again felt a wave of humiliation course through him. As Danny was helped up, the humiliation was made even worse as Demarcus's put his other big paw on his lower back. Well, very lower back as most of his hand landed on Danny's ass!

Danny stood back up, his hand still engulfed by his buddy's massive mitt and his ass still covered in the other. He still felt unsteady on his feet and put his feminine hand on Demarcus's chest to steady himself, unknowingly flirting with the big man as he stared up at him through his big lashes. He still had to look up at him, even with his 5 inch pumps

Demarcus smiled down at the little brunette white girl. "Damn, getting these little snow bunnies is almost too easy at this school. They practically throw themselves at me. This little bitch can't stop stroking my pecs either. I fucking love college" Demarcus thought to himself.

Danny was in shock. Here he was, being held by his roommate dressed like a slut. His big hand on his ass felt like a hot iron. He was so humiliated to be seen by his friend like this, he couldn't let him know who I am. "I gotta play into the role. Can't let him know who I am. Fuck, this plug is making me so horny. Why's my cock twitching so hard in this damn cage??"

"What's your name, cutie? What're you doing over here" Demarcus asked as his hand crept lower, fully encompassing Danny's ass.

"Um I'm Dani...elle. Danielle. I'm um, just visiting a friend in the building." Danny responded in his new feminine sissy voice.

"Oh a friend huh? Boyfriend or girl friend?"

"Oh a girl friend! I don't have a boyfriend!" Danny quickly responded out of habit to explain he wasn't gay, not realizing how that would sound in his new attire.

"Oh really? No boyfriend huh? Well maybe we can change that" Demarcus flirted as he brought his hand up to brush back a lock of Danny's brunette hair off his face.

"Oh um... I... ummmm... maybe?" Danny responded, completely confused on how to respond.

Demarcus took that as an invite, as he bent down to bring his face to Danny's. Danny looked up at him through his big lashes, plump pink lips slightly opened in shock but looking so inviting to Demarcus. Before Danny's brain could respond, Demarcus's manly lips met his pink ones.

Danny's eyes opened wide in shock as he felt the manly lips touch his. The 5 o'clock shadow brushing his cheeks. Demarcuses hand on the back of his head, pulling him into the gay kiss. Demarcus's big thick tongue pushing into his mouth felt so strange! Danny was used to being the aggressor with a woman and here he was on the other side.

It only got worse as Demarcus's hand started pawing at Danny's skirted rear. His big hand was groping Danny's ass. The groping itself felt good to Danny's body even as his brain was screaming inside about the forced homosexual act. But what was worse was the plug was being pushed and pulled inadvertently with the manhandling, causing waves of pleasure to roll through Danny's body.

Due to this pleasure, Danny moaned into the kiss, starting to dance his tongue along Demarcus's. Danny pressed his body into Demarcus, pushing his enhanced chest into him as well as his skirted hip. As his hip pushed into Demarcus's groin, Danny was further shocked by the massive python he felt underneath Demarcus's sweat pants. "OMG that thing is huge! There's no way that's real!" Danny thought as his hips continued to gyrate, causing the big black snake to twitch and move on its own.

Suddenly, Demarcus pulled back from the kiss, still kneading Danny's ass. Danny's eyes were closed, lost in pleasure with his mouth still parted. "Mmmmmmmmmm" Danny moaned.

"Yeah, I think we can fix that boyfriend issue, Danielle. Sorry but I got somewhere I have to be but let's continue this soon. Tomorrow. Here girl, take my number. I'm taking you out tomorrow. Be here at 8. And as much as I like the chase, I expect you here on time and looking.... Sexy"

Demarcus said as he eyed up the cute little white girl in his arms, continuing to manhandle her big ass "damn, this shawty got a phat ass. Not a typical white girl" Demarcus thought.

Lost in pleasure, Danny just rolled with the waves flowing through him. He bit his lip as Demarcus talked, only somewhat understanding he was to be here at 8 tomorrow. As Demarcus stopped talking, his hand pressed the plug deeper into him, cause Danny to gasp. "Yesssssss, sir!" Danny half moaned.

"Mmmm sir. I like that, girl. Why don't you make it Daddy" Demarcus smirked as he pressed on her ass once again.

Another jolt of pleasure coursed through Danny. "Mmmmmm yessssss Daa-daddy!"

"Good girl. I'll see you tomorrow, shawty." And Demarcus left, not before landing a hard slap on Danny's skirted ass. With a yelp, Danny grabbed his now sore ass as he watched Demarcus saunter away.

"What the fuck was that???" Danny thought, shaking his head. He unconsciously smoothed out the front of his skirt and felt a wet spot on the front. Shame coursed through him as he realized how much he leaked precum from the manhandling his roommate just put him through.

"Just get inside and get to bed, Danny. You can fix this in the morning" Danny thought as he strutted into his apartment building.

Unbeknownst to Danny, Jessica sat in her car in the parking lot and turned off the recording on her phone. "God this couldn't have gone better! Now I have the little fairy making out with his buddy! And calling him Daddy! Fuck I've got the little bitch right where I want her"

Jessica thought to herself as she surreptitiously touched her own crotch. She'd never been more wet in her entire life. Turning this straight boy into a gay sissy crossdresser was the hottest thing she'd ever done. Jessica stopped herself from continuing as she turned the car on to go home, excited to wake the sissy up in the morning.

Danny entered his apartment slowly, not wanting to have his other roommates see him in such a slutty outfit. Thankfully, everyone seemed to be gone so he quickly pranced over to his room and locked the door behind him. Danny quickly took off his low cut top and skirt.

Going to his bathroom, he looked at himself in the mirror. In front of him was a slutty brunette in pink bra and thong, black corset, white thigh high socks and pink platform pumps. Her enhanced chest heaved its cleavage with each tiny breath the corset allowed him. Her ass and hips looked incredible framed by the pink thong and black corset. Danny turned and saw the pink strap engulfed by his naturally large cheeks.