Whatever Happened to Jimmy? (Miss June)

 This is a flashback for my Sissy Calendar caption "Miss June" 

“One extra large package just for...” Jimmy announced as he stepped off the elevator. “...Oh! It's you...” He instantly dropped the act upon seeing that the only person behind the ShackUp Lettings reception desk was the stony faced and significantly overweight Matilda. The boring cow was the kryptonite to his charms and an instant buzzkill. While he loved flirting with the other receptionists, especially the long-serving Ellen, who even after all these years was still his favourite, there was just something about Matilda that stopped the Jimster dead in his tracks.

“Ellen's not here today,” Matilda stated flatly, watching the courier slide the parcel silently onto the front desk. He was unable to meet her eye as he fiddled with a handheld device for collecting receipt signatures. The scrawny man appeared completely dejected by her presence. “Ellen, was talking about you yesterday though actually.” She said suddenly, her voice uncharacteristically bright. Jimmy's head shot up to attention. “She was saying how you're always asking her out – and that she has said 'no' about a million times.” Jimmy's gaze dropped back down to his device. “She said you do absolutely nothing for her. Except...” Now she had the courier's attention. “Except...this one time about ten years ago you posed for a charity calendar. You were Miss June, I think. Ellen showed it to me. She still has it, you know? Just that month, of course. I can see why. You were very cute. She said she bought a joke book to keep the banter going between you two, but you weren't interested. She said you were embarrassed. It's a shame really – sounded like she was willing to make a go of it if you had been willing to embrace your feminine alter ego.” Matilda used her finger to scrawl out a signature on the electronic screen. “Hey, how about I talk to her? Maybe she would give you another shot? What do you say? Would Miss June be willing to bring out an early summer?”

Three days later and Jimmy was waiting in a booth at a local bar, his heart thudding in his chest. You could say a lot about the courier, but you couldn't say he wasn't punctual. The wig was the same one from ten years ago. He had left the offices in such a daze that day, he had forgotten to remove it on the way out. The rest of the outfit was new though. He had guessed the sizes and ordered online, yet the hot pink playsuit fit him like a glove. It had taken him four hours to get ready but it would all be worth it if it got him some action with Ellen. The makeup had been the hard part. All the YouTube tutorials in the world couldn't steady his hand as it held those tiny brushes, and he had left trying to walk in the heels until far too late – badly underestimating how much practice it would take to be able to stride confidently into the bar. Though again, this was just a means to an end. Once Ellen got to know him, he wouldn't need to bother with all this crap.

“There she is!” A confident female voice proclaimed from the opening of the booth. Jimmy instinctively took up a defensive position, his hands stretching wide and pressing back into the sofa and his silk stockinged legs sliding up onto the leather. “There's my date!” Matilda said matter-of-factly. “There's my Miss June!” She stood over Jimmy imposingly. “Come on, sweetie, let's go get a drink in you!” She licked her lips hungrily. “I have much to get in you by the time this night is through!”

The Date Part 2

 

With every vibration of Otto's phone that followed, his feminine prison was built more secure. If the picture of the epoxy resin in Tilly's hand had been a barred window, the heavily edited videos that came next each added a lock to an already firmly bolted steel door. His so-called girlfriend was drip feeding him clips of him seemingly willingly, heck excitedly, dressing himself in the figure hugging outfit he was now wearing. 'This is going to be so good!' he exclaimed in one video as he ran fingers through the long hair of his wig. 'I can't wait to see Elijah see me like this!' as he pulled a pair of satin panties slowly up his silky smooth shaved legs. How had he let Tilly persuade him to wear the panties? Boxers would show show from under the short dress, she had said – they wouldn't hug his manhood tightly enough and Elijah might notice... Otto sighed – how had he let Tilly convince him to do any of this...

He had tested the resin of course - pulling at the wig with fistfuls of synthetic hair while in the bathroom had only succeeded in giving him an awfully sore scalp. The acrylic nails wouldn't come off either, nor, Otto realised in horror would the high-heels. The figure hugging dress didn't seem attached and apparently he could drop his panties at will, but that's what the subsequent video messages had been for – Tilly wanted him to finish the date with Elijah or the clips of him gaily dressing himself would be circulated.

When Elijah invited him to his dorm room, he had accepted without thinking – anything to remove himself from staring onlookers, even if it was because they thought he was a hot girl. The dork was harmless anyway and proceeded to give Otto a tour of his hand painted figures and binders of completed DnD campaigns. Polaroids of his gaming club were taped to a mirror and the penny finally dropped. Almost all of them featured a single female gamer amongst the group of sweaty nerds – in one she even had her arms wrapped around the greasy bastard...Tilly.

Otto hid his phone in one hand and glanced back over his shoulder to where Elijah stood awkwardly the other side of an unmade bed. Tilly had just sent him pictures of the makeup she had used to paint his face – each tube and bottle was printed with 'LONG-LASTING' or 'SEMI-PERMANENT'. By now his heart was hammering in his chest. 'I see you have been invited to Eli's bedroom,' the message read, 'by now you will understand what this is about. I have been preparing you to be a fool for much longer than you have been planning your date.' Otto seethed. That bitch! How could she do this to him?! His phone buzzed again. 'But how long you stay a fool depends on you! Eli really doesn't have a clue who you are. You can still make this a night to remember for him. How about it? Either I spread these videos and your life will suck for a long time...or you can suck right now!' One more picture came through – it was of Otto posing suggestively with his short dress pulled up to expose his satin panties and a single finger pressed against his painted lips. It had supposed to be ironic but none of that came through in the picture. He just looked like a complete sissy. Hesitantly, he took a deep breath and gestured for Elijah to join him near the bed – taking care not to trip on his glued-on heels as he got down on his knees.

The Date Part 1

Otto glanced quickly at his phone again when Elijah's back was turned – which was a rare luxury considering the chubby boy's eyes had been fixated on him all evening. Still nothing... He sighed, willing Tilly to hurry up with her cue so they could accelerate their prank to the fun bit – the bit that didn't revolve around him being eye candy for Elijah so he could get on with humiliating the fat Dungeons and Dragons obsessed doofus.

“Everything alright, Baby?” Elijah smiled sweetly. “You look cold. Care to wear my jacket?” Cold?! He wasn't cold!? Hell, it was actually pretty warm for early April. But, he did want that jacket. He didn't care that it had been wrapped around that sweaty boy's body. Anything would be better than what he was actually wearing. Otto instinctively looked down at himself and instantly regretted it, cursing the fact he had listened to Tilly when she suggested starting the date early in the afternoon. Of course, there would be more of an audience for Elijah's ultimate humiliation, but by extension more people would get to see him in his role too, and with the daylight lingering, they would get quite the view.

In truth, it could have been a dark evening and Otto would have still cut the striking figure. Tilly had done a fine job of preparing him for their April Fool's prank. Their mark was the greasy and grossly overweight enternal-virgin from their freshman year college study group, Elijah. Their plan was a classic – Tilly would help her boyfriend, Otto, dress as an overly eager female date for their classmate, make him think he was getting lucky, build him up, and then just as lover boy leaned in for a kiss to seal the deal, the wig would come off, Otto's friends would jump out laughing, fingers pointed, phone cameras poised, and Elijah would never speak up to correct him in class ever again. Hell, that stupid ass might never even show his face again.

Otto looked at his phone once more. He was getting impatient now and no longer cared if he seemed rude. Like he was going to upset a guy who wore a DnD shirt on a date. He actually felt offended on behalf of the female alter-ego Tilly had crafted for him. The long flowing hair, the perfect makeup, the short figure-hugging dress that clung to his smooth moisturised skin...the shiny fuck-me heels Tilly had given him as a finishing touch and then proceeding to teach him to walk in. Otto wasn't even a real girl and he was still too good for this loser. It was no wonder Elijah had clearly fallen in love already – the geek's eyes bugging with every wiggle, every shimmy that Otto threw his way. They weren't just going to humiliate him, he thought gleefully. They were going to break his heart.

Finally, Otto's phone vibrated in his hand. As expected, it was a message from Tilly and he opened it eagerly. But wait...he narrowed his eyes heavy with false lashes and wrapped his extended nails around the device like talons. He studied the picture Tilly had sent him. She had clearly been holding her phone in one hand and pointing it at assortment of objects on a table. Otto recognised them instantly given he was wearing all of them – a long flowing wig, the high-heels, acrylic fingernails – yet it was what was in Tilly's other hand that stopped his heart in his chest. Her palm was open and facing upwards, a small bottle lay in it with its cap unscrewed – 'Never-break Epoxy printed on its label.

 

Little Benny's Easter Jamboree

 

“What the hell is all that crap?!” Jill screeched upon seeing Ryan unloading the huge box from the back of their van. Brightly colored streamers were bursting from the top and Ryan was using his chin to stop a pile of bunny-ear headbands from falling to the floor. With a confused expression on his face, Ryan lowered the carton to the ground and Jill began to rummage through it. Together, the pair owned and ran a new and already struggling party hosting business and while they were supposed to be partners, having put up most of the investment money and the down payment on the company van, Jill was very much in charge. “What is all this?” She was pulling out items at random – plushy bunnies, paper plates, little yellow fluffy chicks, and dozens of small colorfully wrapped chocolate eggs.

“It's the stuff for Little Benny's party.” Ryan responded as if the answer was obvious. “You know, the Easter Jamboree. I just figured we were going with the standard egg hunt and party games and spent the budget accordingly. What's the big deal?”

“The big deal?!” Jill's mouth dropped open. “The big deal is 'Little Benny' is an ironic nickname. The big deal is Little Benny is a six foot five dude turning thirty this weekend and his friends are turning up here in two hours expecting us to have a surprise party for him, and my idiot partner has just spent our entire budget on baby chicks and chocolate eggs. I bet you haven't even booked a hostess, have you? Did you even read the booking form?”

“Well... hmmm...” Ryan blushed deep red and stammered sheepishly. He hadn't, of course, and was scanning the box of Easter knick-knacks for some inspiration. Finally, his eyes settled on a pair of the bunny ears and he raised them for Jill to see. “Well, I suppose you could wear these, and play the role of hostess?”

Needless to say, Jill did not play the role of hostess. That honor fell to the junior member of the partnership, Ryan. A hasty run to the store for some crates of beer had been enough to distract Little Benny's friends from the lack of an organised party – especially once the hot little bunny girl made her debut. Jill had sped home and returned with a satin corset and matching panties, as well as a blonde wig and her makeup box. She had been merciless in packing Ryan into the underwear, not so much showing him how to tuck as stuffing him into the knickers like a turkey. There was no effort spared when it came to shaping his body with the corset either and by the time it was firmly tied, Ryan could barely breathe. Makeup was then slathered on and by the time Jill was finished with him, he didn't even recognise himself.

“Oh, hostess!” Jill called coyly across the busy room to where Ryan had been trying to hide in a quiet corner. He had spent the last three hours serving beers, listening to drunk guys try to chat to him and dodging the odd wandering hand, and he just wanted the whole humiliating experience to be over. “We're about to sing Happy Birthday to Little Benny!” Ryan glanced to the table where the cake was waiting and braced himself for trying not to drop it while tottering across the room on six-inch heels. He adjusted the top of his corset to make sure the silicone padding was sitting naturally. “Oh no, I've got that.” Jill said. “I have promised the birthday boy that the beautiful hostess will sit on his lap while we sing!” Ryan paused – his stomach would have dropped were the corset not clenching it so tightly, and looked sideways to where Benny was sitting. He really was a mountain of a man – a wide grin on his face as he patted his thigh invitingly.

Season 8 Prologue - Lara Lake's Last Lament Part 1

 0/25

Starting out Season 8 with the Mannequeen

Each call out filled her with dread now. Each crackle of her police rover put a sick feeling in the pit of her stomach that this was it – the time that she would be made to finally lie in the bed she had made. That's why when Detective Lara Lake's radio came to life one shift and the dispatcher informed her of a possible Mannequeen incident in a mansion on the edge of town, she was instantly on edge. Was this where she would be made to pay for aiding and abetting the copycat that went by the moniker of the Cleaner.

The massive house was registered to a man called Wesley Tanner and when Lara discovered the moaning figure in one of the many upstairs bedrooms, she immediately knew two things; she had found Wesley, and this was indeed the work of the Mannequeen.

The woman on the bed wore only a skimpy underwear set and reeked of cum and perfume. Wesley groaned and looked up at Lara through eyes caked with heavy makeup as the detective drew her sidearm and looked around for signs of whoever had been ravaging the bodysuited Wesley – or worse still, the Mannequeen herself.

Entering the room, Lara had to bring her free hand to her mouth. What the hell was that perfume?! It was flowery and pungent like nothing she had ever smelled. And how much cum had been pumped into Wesley that she could still smell it in spite of the overpowering fragrance?! She entered the room and started to circle the perimeter, maintaining her back to the wall. The bimbofied tenant fixed her with his empty gaze and followed her position wordlessly, an ungodly blend of fear and lust—and she felt a premonition of her own future mirrored back at her.

The detective studied the used feminine creature and the bed covers tossed around her, all the while forcing herself not to choke on the fragrance. There was something missing, she realised? Where the hell was it?! The room spun, the walls seemed to close in just as the world she’d known had.

“Where is it?!” She raised her gun. “where's the tape-recorder?” She scowled as Welsey continued to stare at her with same blank expression. “Tell me where it is now!?” Panic was rising in her chest now. Something was wrong. There was always a tape – always a message to let the bodysuited victim know how screwed they were. Finally, the detective lost her patience. Holstering her weapon, she strode over to the bed and grabbed the figure by her bra-straps. “Where is the fucking tape..” she spluttered unable to speak as the perfume entered her lungs, overwhelming her, overpowering her. “Shit...” she gasped at last and fell unconscious onto the bed.

Whatever Happened to Robert? (The Apprentits)

 Robert last appeared on my Apprentits series - specifically this episode. All my Network captions are available on my index page.

“No sex in the champagne room,” The Juggernauts security guy said dryly as he lifted the velvet curtain for them to enter. “No cameras either!” He pointed to the device on Bryan's shoulder. “Come on, hand it over or you're not going in!” Bryan relieved himself of his equipment and followed Madison into the smoky room. The Frontline Entertain Media team were looking for another scoop ahead of the premier of the lost tapes of Femnonymous's perverted version of the Apprentits, and they were surprised to learn that a former Apprentits contestant was still working at a local strip joint. In the room a curvy bottle blonde wearing a black bra and thong underwear set swayed side to side on a pair of six-inch stilettos.

“I know you're here to interview me,” The woman purred from behind a face full of makeup. “But do you mind if I practice my routine while we talk? A prepared dancer is a well-tipped dancer!” Madison made a little surprised 'o' with her mouth but waved for the stripper to continue. “I suppose you're surprised I am still here after all these years... My forfeit on the show was only for a year after all.” The voluptuous woman who had once been Robert Williams, former child-star and losing contestant on the Network's Apprentits smiled wryly. “In some ways this is the best job I have ever had. The tips can be good too... Of course it helped that my trust fund was cut off after I apparently humiliated by family name on that freaking show.”

“Is it true the Network bought this club during the show just to force you to work in it?” Madison followed the sight of Robert's naked flesh as it gyrated and quivered before her. It was mesmerising to think this creature had once been masculine. “We've been interviewing Femnonymous victims over the past few weeks, and it's some freaky stuff. But what happened to you is just as extreme?”

“Oh yeah, they pulled no punches with me.” Robert said as he bent over with surprising agility and wrapped his arms around his calves, pushing his ass high in the air right in front of the two interviewers. “Of course, it's all Bryce Murphy's doing. He's the Network's CEO. Total psychopath. As you would imagine a guy who owns a line of game shows fixated on transforming men into women...into bimbos...” Robert put his hands on his knees and sank into a crouch. “You know he gets off on this stuff? Does that even surprise you? He visits the club sometimes too. Gets me to dance for him. He makes me feel like his own personal toy.” Robert finally stopped his routine and stood up high on his heels. “He brings his wife sometimes too. She's a bit of an airhead in her own way...a bit of drone. He has us do a bit of girl on girl. Not that I mind that bit – she's hot as hell... It's just...well, creepy. I know everyone thinks Bryce is crazy for wanting to release the Femnonymous tapes, but if you met the guy, you'd know it was right on brand.” He picked a bottle of champagne, popped the cork on it, and collapsed into one of the leather sofas. “We all know the Femnonymous show is going to be extreme – but Bryce is going to be watching with his ideas notepad in one hand and his dick in the other!”

Whatever Happened to Lance? (A Queen's Ransom)

 This continues my Femnonymous/Network stories, but the flashback is for one of my first captions - A Queen's Ransom. Part 1 is here.

Madison and Bryan knew it was a risk but the time was now or never for getting Frontline Entertainment Media on the map. Online gossip sites were already saturated with stories and scoops on the upcoming airing of Femnonymous's presumed lost version of the Network's own Apprentits and their interviews with past victims of the underground group had barely made a splash.

They stood in front of the large town house, microphone and camera at the ready, and they burst forward the second the door opened, knocking a flustered housekeeper to one side in the process. Senator Laney Charleton, formerly Lance, stood before them in the lobby leaning to adjust the ankle strap of an open-toed high-heel shoe. Her mouth dropped open until she saw the camera slung over Bryan's shoulder, and her politician's mask instantly reformed.

“Senator Charleton...” Madison gasped breathlessly. “How do you respond to allegations that your public gender transition eleven years ago was a total sham? And in fact you were actually the victim of one of Femnonymous's transformations? There first victim in fact...”

“Allegations from whom?” The Senator spluttered. “I will sue them, and you, if any such allegations are ever made public.” The blonde politician scowled and straightened her suit. “Do you really think I would persevere with these blasted shoes if it wasn't what I wanted? Now leave, immediately, before I call the police!”

“It has certainly been the making of your political career,” accused Bryan. “I hear you're in the running for the next vice president...” He shifted his camera to the other shoulder. “In a couple of weeks everyone is going to find out what really happened to those six Network producers who were kidnapped and forced to play the Apprentits. Who's to say some of Femnonymous's other victims won't also be on the tapes?” The Senator's face was suddenly ashen.

“Senator Charleton...” Madison took another step forward. “What about speculation that the airing of these tapes will anger Femnonymous, and provoke them into returning? You may have transitioned, whether willingly or not, but your policies have remained as misogynist as ever. Don't you worry that if Femnonymous do return, you might be high on their target list?”

“Target list?” The Senator repeated mechanically. The blood had drained from her face and she was fidgeting with the top button of her blouse. “Listen to me carefully and turn off that camera!” Madison nodded to Bryan and he lowered his equipment. “If you quote any of this, I will deny it. I don't know what's going to be on those tapes...or who is going to be on those tapes. If it is those producers, you're going to see them transformed into silicone messes for the entertainment of the masses. But if Femnonymous do come back because of this, it won't be me they go after. They will have their sights set much higher. They will have plans far beyond what your little brains could imagine...”