Masculinity Lost Ch. 07-08

Hey guys and girlies (and gurlies)! Thanks for all the likes, comments, and especially messages! Please let me know what you think about the stories and if you have ideas too! Even just a simple hello makes my day!

Anyway, here goes the next chapter in sissy Dani's story!

Chapter 7: Dani finds out Jessica's Plan

Danny stood there stunned, hand to his O shaped lips as Jessica took more and more pictures of the pink covered sissy! Finally, he came to his senses and tried covering himself up. One hand flew to cover his satin covered cock, still hard as a rock (a small rock), and oddly one hand went to cover his chest. Seeing his chest look so full and such deep cleavage, he oddly felt the need to cover them up to try and preserve his modesty.

"Oh Dani that's just precious! Your new girly image has already started to have you think like a girl, covering up the girls! Hahaha too late sweet heart, I've already got dozens of pictures of your newly enhanced assets! How about you come here and show off for the camera sweet cheeks! Hahaha" Jessica smirked as she switched to video mode.

Danny couldn't believe what was happening. I'm a straight guy, masculine guy (or so he thinks). I can't be seen dressed like such a slutty.... SISSY! While he may look beautiful, his hard cock on such prominent display would ruin his reputation. I'll never have another girlfriend again, let alone what the frat bros will think if they see these pictures! Why was he still so hard with all this going on? These clothes, the soft sensual feeling on his skin, it just wouldn't go down! He had to get rid of these photos.

Danny started stepping towards Jessica with the hopes of grabbing her phone and deleting these incriminating photos. "Jessica no please! No one can see me like this! Please.... Eeeppp!" Danny, still unfamiliar with his sexy stilleto pumps, took a few steps but immediately fell back onto the bed, covered in a pink comforter. Danny's stocking covered legs and patent pink heels flew back to his head as he lay on his back, showing off Danny's barely covered crotch and ass, cock still hard as ever covered in pink satin.

Due to the strict bones of his corset, a Danny flailed around kicking his sexy legs trying to get up, providing Jessica with plenty more footage. Danny finally rolled himself onto his front and got on his hands and knees. Unfortunately, his satin covered ass was on display for the camera.

The body suit was already cut in a cheeky manner to show off the bottom part of the wearers ass. But due to the size of Danny's pronounced rear, as well as the bent over position, the material wedged itself between his Lucious cheeks into a near thong. Panting from exertion and fear, Danny ass also swayed back and forth and up and down, looking like he was enticing someone to come and take it.

Danny finally turned around and got onto unsteady heels. "Listen Jessica, I don't know what the fuck this is but it needs to stop!" Danny pointed a finger threateningly at Jessica, too afraid to try and take another step in the skyscrapers on his feet, but with his new outfit and girly makeup, he looked like a cute teen girl, pouting with her big full lips, failing terribly at being fierce.

"Now you listen here you little shit. You shut your pretty mouth and listen. I don't want to hear another word from your mouth until I tell you to speak. If you say one more word, these pics and videos get posted all over IG and Twitter with you tagged in all of them. Got it, sissy? What I hold in my hands can destroy you. Your reputation as a playboy frat boy will be over once everyone sees how pretty you fill out your pink body suit. Now sit your sissy ass on the bed and cross your legs while I fix your hair and make up. Your thrashing around messed it all up. Oh, and don't try and grab my phone. I've already uploaded them into my cloud storage sissy Dani."

Danny stepped back and sat down onto the bed with his mouth gaping like a fish. Finally, he sat down and shut his mouth with a loud click of his teeth. When Danny saw Jessica's raised eyebrow while waving her phone back and forth, Danny quickly crossed his legs and put his hands on his knee.

Jessica bent down and started grabbing stray strands of hair and started smoothing them back into his pony tail. "Now Danni, you turned out better than I imagined! I first called you over here to reject you like you did me. Dumped and humiliated like a sack of potatoes. I was gunna get you all horned up, ready to go, and leave you blue balled and naked. Buuuuttt you showed up in that cute little outfit, already looking so feminine and girly and I was like, what did I see in him as a guy. I mean, don't get me wrong, I'll mess around with a girl or two, but I want a man, a real man to be with." Jessica finished slicking back Dani's tight high pony tail and moved onto fixing his eye make up, grabbing the eyeliner and fixing any smudges.

"I guess you did tickle my lesbo itch and that's what drew me to you. But seeing you in your little crop top and tiny shorts, with no bulge to be seen, I realized I might not be as lesbian as I thought. But more importantly, I realized how pathetic of a man you are hahahaha. And I decided to change how I was gunna humiliate you. I was gunna get you all dressed up in the cute little outfit you're in now and post your pictures all over campus. Sure, some people would support you for becoming 'yourself', but you know that your life as a womanizer frat boy would be over. Your frat bros would ostracize you and any sorority girl wouldn't touch you with a ten foot pole." Jessica finished with a last flick of mascara and grabbed the tube of lipstick.

"Now pucker those big fat lips of yours so I can smooth out your pretty pink lipstick. So anyway, once I saw you all dressed up, with that fat perky ass peeking out of your cute little body suit, I realized I LOVED feminizing you. Turning a 'straight' boy into a feminine girly girl got me all.... Mmmmm so wet. I guess my lesbian side is still there after all. So an Idea came to mind."

Jessica rolled the lipstick over his mouth and had him press his lips together to set the lipstick. She grabbed the shiny lip gloss and lightly spread it on his hot pink lips.

"You're gunna be my little sissy slut. My little dress up doll. And you will do whatever. I. Say." She punctuated her words with dabs of the lip gloss applicator. "I'll keep your secret, for now, but you will be my little sissy whenever I tell you to be. You'll wear what I tell you to wear, and anyyyything else I want you to do."

"And if you don't, those pictures are going up everywhere, just like I said. So sissy girl, what's it gunna be?"

Chapter 8: Obviously he stays with her

Danny shook his head. He couldn't believe his predicament! There's no way he could live down these pictures. He'd never get laid again, with girls at least. "Ew no! Why would I even think about having sex with guys?? It's just the clothes, get it together Danny!" Danny thought to himself, trying to calm down.

He had to take Jessica's other offer and figure a way out of this. There has to be a way out, right? Jessica isn't evil. Danny will use his sweet talking moves and boyish charm on her and everything will work out. Just have to get out of this ridiculous outfit first. "Ugh and why is my dick still so hard???"

"So sissy, what's it gunna be? Exposure? Or be my little plaything?" Jessica said as she played with Dani's pony tail, curling it around her hand lightly.

Danny sighed, shaking with fear as he said "I... I'll stay with you Jessica"

Jessica's grip on Danny's pony tightened, lifting his head up forcing him to look into her eyes. "No, I want to hear you say it. Tell me what you're gunna be for Mistress"

Danny gulped, scared and harder than ever as he whispered "I'll... I'll be your sissy slut Miss"

Jessica pulled on his hair harder. "Louder, sissy! I can't hear you!"

Yelping, Danny said much louder "I'll be your SISSY SLUT Miss! I'll be your dress up doll and do whatever I'm told!" Dannys voice got higher from the pain.

Releasing his hair, Jessica smiled "good girl! And such a pretty voice too. Keep your voice like that when you're with me sissy. And you'll continue to call me Miss or Mistress. Now, I saw how wobbly you were in your new pretty footwear so we're going to practice. Stand up and you're going to walk back and forth until you stop looking like a clumsy boy in your stilettos. Get up sissy slut!"

Danny stood and Jessica slapped his butt, causing it to ripple and jiggle, eliciting another feminine yelp from the hapless sissy.

Danny started walking very slowly across the room, hands held out like walking a tight rope. He barely made it to the end of the room before falling, barely catching himself on the end of the desk. Jessica watched with a hand to her chin thinking

"Hmm well that just won't do. You look like Bambi on ice! Try holding your arms down at your sides with your wrists turned outwards. Then, make sure you go heel to toe with one foot in front of the other. Chest out with shoulders back and stand up straight"

Danny turned and turned his dainty wrists outward, his arms looking very feminine. Danny was forced to keep his back straight due to the restriction from his corset, and with his shoulders back his new feminine chest was out on display, jiggling slightly with each high heeled step. Danny put one pretty pink heel in front of the other, making a distinctive sexy click clack as he took each step.

Danny's mind was in shambles as he clumsily sashayed across the room. Here he was, a man (supposedly), wearing a push up bra giving him realistic c-cup tits, a thong wedged between his ample backside and barely containing his 4 inch cock, a pink playboy bunny high cut corset body suit with garters attached to his pink stockings, make up covering his face looking like slutty girly girl, all while tottering around on 5 inch pink platform pumps.

His usual masculine bravado had been silenced by the encircling femininity. The bra straps tight on his shoulders causing his titties to jiggle with each step. The garter straps getting taut with each step reminding him of his leg wear. The heels causing him to hold his arms at his side, wrists out turned, chest out while he tried his best to strut on a cat walk, or a stripper stage. How could he get out of this nightmare???

As he reached the end of the room again, Jessica tapped a long pink fingernail against her lips in thought. "Hmm, still not quite girly enough. You're looking much too mechanical and "manly" in your steps. Too stiff. We need to get those girly hips and ass moving. Aha! I know just the thing! And, it'll get you ready for your new life, sissy Danni! Now, bend over the bed and stay there. If you move, I'll spank your ass raw AND send the photos out to all your family and friends. Now hop to it, bunny girl!"

Danny pranced over, carefully, to the bed scared that she will make good on her threat. Always a lover, never a fighter, a spanking sounded terrible, let alone being exposed as a pretty pink sissy princess! "Please don't Miss, I'll be a... good girl" Danny struggled to get the words out as he bent over at the waist on to the bed with knees locked and ankles close together.

Danny heard Jessica rummaging through a drawer and sat up on his elbows to look over his shoulder. Jessica saw Dani laying on the bed, her plump ass showing a lot of skin from the skimpy body suit and sexily framed by the garters, looking over shoulder like a girl waiting for her lover to enter her. Jessica gave a wicked smile as she was all to happy to oblige, hiding what she found behind her back.

"Now now, sweet sissy bunny. I know you're anxious for your little gift but no peeking." Jessica slapped Danny's ass moderately hard, letting it jiggle. Danny gave a yelp of pain and surprise, knowing he couldn't handle any more spankings.

Surprising to him is that his cock got harder at the slap and he felt a little more wetness at his crotch. Jessica bent over to whisper in Danny's ear, her crotch pressed up against Danny's sissy ass "Any more issues I'll spank you ten times. Understand? Now, this will be a little training tool for you to get that feminine wiggle and roll to your hips. Just lay there and look pretty sissy girl."

Jessica stood up once more and set up her phone to record, wanting to capture the moment. She walked back in her heels and started caressing Danny's ass and back of his legs. Her soft touch crept up between Danny crotch, forcing his legs apart like a man does to his woman before entering her.

Her soft hands gently brushed Danny's rock hard cock, feeling the wetness from his precum. "Mmm your little clit is so hard sissy girl. I think you've been lying about not wanting this. Your little clit here is telling the truth. Just wait, sissy girl there's so much more to explore"

Jessica kept gently stroking his clit with her finger tips, careful not to let him explode, as Danny closed his eyes and moaned softly, lost in the euphoric feelings. Danny suddenly felt cool air on his ass as Jessica unzipped the back of his body suit from the top of his ass just down to below his little hole. Danny then felt a cool liquid being softly applied to the outside of his hole with a finger.

Danny had his ass played with by a few girlfriends in the past while getting a blowjob, but it was only to the first knuckle. While he didn't hate it, it really affected his straight masculine image so he didn't pursue it again. But now, combined with the soft feminity surrounding him, the edging, and also the fear, Danny softly moaned at the pressure on his hole.

Jessica giggled "Ohhh my little sissy likes this! If I had known you liked your boy pussy played with when I was dating, I would have done it a lot more! Hahaha oh your ass is just gobbling up my finger. You think it could take a second? Mmmmm oh that's tight! And those lovely feminine moans. That's right sissy girl embrace it!"

Danny was moaning, the feeling of his pussy, (my ass not my pussy!), being filled was incredible. But the physical feelings were combating the mental. A man shouldn't enjoy having his ass played with! He should be doing this to some slutty girl, not be the slutty girl.

"Ohhhh Miss, please.... Please... please" Danny couldn't get the words out.

"Please what? Please more? Oh I think I can accommodate that sissy girl"

Jessica pulled her fingers out of Danny's wet pussy and Danny let out a sigh of relief. But why was he pushing his ass back, trying to get filled once more! Jessica saw the wanton ass begging to filled and placed the metal plug at his slightly gaped entrance. The plug was medium sized, only 2 inches across and 4 inches long. Have to work the slut up to bigger plugs! She slowly started pushing it in, rotating it to let it slide in easier, as she continued to play with the sissies satin covered clit.

Danny, feeling the cold metal on his ass, went numb with fear. She's gunna put something inside me! Oh no, fingers from a girl are one thing, but having a foreign object inside of him was too much!

"No! NO! Please don't! Don't put that inside me please..... UNNNGGGHHH!" Danny pleaded but was cut short as the widest part entered into his sphincter. Feeling like he was being split in two, Danny's mouth was left open in a wide O, unable to make coherent sounds. Finally, the widest part slipped past his sphincter as it was sucked in to the flanged base.

"Mmm good you got it all inside you! But, that outburst is going to cost you, sissy bitch. Now stand up so I can show you your new toy" Jessica spanked his ass, cause him to jump when the plug inside him shifted from the sharp slap. Danny stood, straightening out his outfit unconsciously as Jessica led him to the mirror once again.

Jess turned him around and Danny was once again shocked. Right in the center of his perfect heart shaped ass stood a white fluffy tail. The plug had a bunny tail attached to the base! Danny involuntary clenched his pussy (ass! Damnit! I don't have a pussy) and saw the tail jump.

"Hahahahhaa oh so cute! The tail moves too! It's like it has a mind of its own, like the little carrot stick you have in your panties!! Hahaha now, try walking across the room with your little helper in and let's get this right"

Danny started taking steps across the room as he was told. Heels to toe, one foot in front of the other. Arms at his sides with wrists turned outwards. Shockingly, he found his hips moving much more fluidly, giving that side to side roll he loved to watch girls in heels do. But now, he was that girl. He glided much more gracefully across the room and turned. Embarrassingly, he saw Jessica had her phone out again filming him.

"Ok sissy, now walk towards me and tell the camera what you are. If it's not convincing, I'll take my 12 inch black dildo to your ass instead of that little plug. So make sure you convince me and the camera that you are a pretty pink sissy girl! And make sure to thank me for helping you come out as what you truly are inside! It better be in your cute little sissy voice too bitch!"

Danny blanched at the idea of saying those words out loud, but the fear of a big black dildo in his ass overruled that fear. He will find a way out of this, but he just had to get through tonight!

"Jessica, thank you so much for helping me get dressed in my cute bunny outfit! It means soooo much to me to have your help becoming the... pretty sissy girl I was made to be! I feel so cute and sexy in my outfit and heels! Thank you thank you thank you *blows a kiss*"

Danny wanted to throw up after the over the top feminine words coming out of his mouth, especially blowing the kiss, but he thought over the top would be better than risk a 12 inch dildo in his ass!

"Oh that's just precious, sweetie! Of course I would help you! When you came over and told me you were actually a sissy girl, I was shocked. You were always such a ladies man, but you said that was just a cover. You wanted to be like the girls you were fucking, not be fucking them. And who knew you were so cock hungry too! I thought you were straight but you told me how you have been eyeing up the guys in the showers wishing that you could have a taste of their big meaty cocks! What a slut! Isn't that right, Dani?"

Danny's face would have gone pale white from Jessica's words if it wasn't for the foundation and blush covering his face and cheeks. He was going to push back against Jessica's words when she pulled out the 12 inch dildo from behind her back.

The dildo was realistic, with veins and dark black lifelike skin leading to a set of heavy black balls. She wagged it back and forth in a "no no no" gesture. Danny immediately put a smile back on his face, accepting his fate.

"Oh yeah of course I'm a.... *gulp* gay sissy girl! I only slept with those girls cause it was the closest I could get to BEING them. I wanted to be the girl being... pushed to her knees by a... big strong man. I wanted to be the girl being.... Ughh thrown onto a bed and.... Fucked like a slut. Thank you so much for accepting me like this and.... *gulp* helping me look how I feel!"

"Well sissy Danni, I'm happy to help! Now, you told me you had never sucked a cock before and wanted pointers. Wellllll, let's practice now!" Jessica showed the big black dildo to the camera before panning back to Dani, a look of shock on his face. While he felt terrified by what she was insinuating, it looked to the camera like his pink sparkly eyes were wide with excitement and his pink plump lips were open to get ready to suck on the black lollipop.