The Making of Ana

Ana looked at herself in the mirror as she applied her bright red lipstick. It was the finishing touch that he had requested, he said it would make or break the outfit. She knew she had to make him happy, or things could go very badly for her. Her! she was even referring to herself as a she now. So much had changed over the past few weeks.

Ana stood up and waked to the full-length mirror on the wall of the hotel room, she was dressed just as requested. Black silk and lace lingerie complete with garter belt, black silk stockings and black stiletto heels all finished off with a sheer black robe with feather trim.

She had painted both her toenails and fingernails bright red, also a request and spent hours making sure her body was completely smooth. Her flat chest was to be padded with breast forms tucked into her push up bra. The final request was her long raven hair was to be straighten and her makeup was to be done to the best of her abilities. She had spent a long time on YouTube watching tutorials to make sure she did the best job she could.

As she was admiring the fruits of her labour for the last hour and a half, she heard the buzz of her phone vibrating on the dressing table. It was from him.

"Look outside the door, your guest will be with you in 10 minutes, I trust you are ready, remember I'll be watching."

"Yes Sir, I'm ready."

"You will be when you see what's outside."

Ana timidly opened the door; she'd never been dressed in public and certainly not dressed as a slutty as she was now. On the floor in front of the door was a small red bag, the kind you would put a gift in.

Ana took the bag inside and closed the door quickly. She pulled the small black box out of the bag and opened it. Inside was a white card, when she picked up the card, she gasped at what was underneath, a large silver plug with a red heart shaped jewel and a small black chastity cage, complete with tiny black padlock. There were no keys in sight, however. Ana turned over the card.

'Put these on. Your guest has the keys. If you please him enough, he may let you take off the cage when you are done. Master x'

Ana walked to the bedside table and picked up the lube she had laid out, lube and condoms were part of the shopping list she had been sent earlier in the day. also on that list were her outfit, makeup and one last item that made Ana's heartbeat quicken, a leather flogger.

She sat on the edge of the bed, slid the black silk thong down her stocking clad legs until they were around her ankles, she really did enjoy the feeling of the stockings on her smooth freshly waxed legs. She caught herself rubbing her red fingernails up and down them, she felt a warm sticky substance at the top of her legs and realised that she had started to leak. How could this be turning her on! She looked at the clock, shit! Only 5 minutes to go.

She squeezed the lube into her hands and started to rub it around the plug, she reached back and ran her fingers around her tight little hole. Inserting one to make sure she was well covered. She pushed the plug to her puckered hole, she could only get it a little way in before it started to hurt, she held it in place and took a deep breath before pushing further.

Again, the pain was too much, and she had to stop but soon after the pain went away and she pushed again, little by little this cold metal plug eased into her ass, until the widest point had passed here tight entrance and her ass almost sucked the plug deep inside, at that point she was filled. She had never felt the feeling of being full before, she thought to herself that she had never known what she'd been missing.

She was leaking even more now, this helped her to slide the cage over her limp cock, sorry clitty as she had been told to call it from now on. The padlock clicked into place, and she was trapped. She pulled her thong back up; she could still see the cage through the lace of the panties.

And then it came.... the knock at the door.

___________________________________________________________________

"Come in!......" the knock at the door had startled him from his daydream, he'd been scrolling through his phone looking at the usual sissy content, lewd captions, and images skinny fem boys next to huge men. He quickly locked his phone and put it face down on his desk.

Henry's office was small and grey with one tiny window, he liked to call it an office, but it was more of a large cupboard. He'd earned it by being one of the best salespeople in his small company, he hated his job, but it paid well, everyone kept themselves to themselves and he could do the job in his sleep.

The door crept open and Charlie, Henry's assistant poked her head around, not actually coming into the room. Charlie was petite but had curves in all the right places, she dressed really plainly for work, simple skirts, and blouses but Henry always thought that she was secretly promiscuous, it's always the quiet ones.

"Rob wants to see you in his office, he said it was urgent."

Henry walked down the corridor, passed the glass walls looking into various conference and meeting rooms until he came to the big corner office at the far end of the building.

Robert Cline Managing Director the door read. He knocked and waited, wondering what the boss could want. He tried his best to avoid all contact with Rob after what had happened at last year's Christmas party, he'd still not gotten over it.

"Enter!" Henry hated how pompous Rob was, just say come in like anyone else.

He opened the door and strode into the office, immediately noticing who was sat on the green leather chairs in front of Robs desk. His heart immediately sank, and he felt sick. It was her, the women that had torn his heart out only 6 months earlier.

She looked incredible as always, legs crossed in tight leather trousers that were tucked into black suede ankle boots, a tight white wool jumper that really highlighted her slender figure and small but beautifully formed breasts, her blonde curly hair sat just on her shoulders perfectly styled as always, her outfit finished with bright red lipstick. She turned her head and looked Henry up and down, "hi baby," she said.

"Please don't call me that," Henry snapped.

"Sit down henry," Rob interrupted "Talia and I have something to discuss with you."

Rob was tall and extremely handsome, he dressed well and exuded confidence, everything that Henry wasn't. He was around ten years older than him, but he clearly kept himself in shape, his arms were nearly the size of Henry's waist. Today he was dressed in a navy-blue suit, it had clearly been tailored as it fit him perfectly. His open collared white shirt was unbuttoned just enough to give a glimpse of his chiselled chest and his suit trousers fitted enough to emphasise his huge thighs without looking too tight.

Henry could feel butterflies in his stomach, he'd not actually been in the same room as the two of them since that day. The day he found out rob had fucked Talia in this very office at the Christmas party last year. Henry and Talia had been engaged when it happened and were all set to get married, Henry looked at the date on his watch, the 17th, in just over a week's time.

Henry couldn't get the thought of Talia bending over the desk, her long legs on tip toes as Rob's huge frame pounded her from behind, her calling out his name and asking him to fuck her. The pair of them locked in carnal lust. All the while henry was stood down the hall in the conference room making small talk with his colleagues.

"Henry, as you know we have just had our new state of the art IT system installed and the report it has generated has flagged some interesting usage on your account."

Rob typed something into his laptop and swivelled the screen around to face Henry and Talia. It was the cover page of a report that was titled user history: HMadson1.

"Is this your username?"

"Erm...Yes," Henry said, not really sure where this was going.

"We ran a review on all current business users just to check nothing untoward was happening, your report all came back clear, no problems with your work laptop or work phone."

Henry breathed a sigh of relief; he was always extremely careful not to search for anything inappropriate on his work devices.

"But then we ran the check on your personal devices...."

"My personal devices!?" spluttered Henry.

A sly smile broke out across Talia's face, she clearly had already been shown the report.

Rob scrolled down to a page titled, personal mobile: 27 red flags.

"How.... did you get into my personal device?"

"Ah good question Henry, the system can get information on any device that logs into the company WIFI at any point, whether they are currently logged in or not."

"Do you want to have a look at what came up from yours?" Rob had a malicious grin as he spoke.

"No, I don't, what does this matter? You can't fire me for what I do on my personal device? I could report you for invading the whole companies' privacy!"

"Who said anything about firing Henry, where would the fun be in that! Also, we haven't run this report for anyone else in the company, just you."

"We were both intrigued, given your 'history' with my beautiful fiancé."

All the colour drained from Henry's face. "fiancé?!"

"Oh, sorry baby, didn't you know? Rob got me this last week and I obviously said yes! It's so beautiful isn't it!" She held out her hand and showed off the biggest diamond henry had ever seen. He almost burst into tears right there, this was the women he had loved for so long sitting in front of him without any care of how he felt. She was like a totally different person.

"Your visited websites make interesting reading henry," Rob continued.

Hypnotube, sissyhypno, sissysocial, sissymarket. Were all listed on the screen Infront of him

"Something you want to confess?"

"Erm, no, I just like looking at trans porn, there's nothing wrong with that!" Henry spluttered.

"Oh really?" said rob unrelenting "how about if we scroll down the page?" he scrolled down, and henry's heart sank.

Camera Roll was the title and underneath were at least 50 images of henry, all in various outfits, panties, thongs, stockings, wigs.

Pictures on his knees, tongue out, pictures on all four's ass in the air, it looked like a porn magazine.

"Anything to say for yourself?" Rob asked.

"Erm, er..."

"I always suspected you were a faggot," Talia chimed in harshly, "That's why I had to get me a real man that would take care of my needs! You know the same needs you have sissy!"

"I'm...not...I.....just," Henry couldn't compose himself.

"You just like to send lewd photos to men," she continued "have you ever thought about pleasuring a man?"

"No....no...."

"Well maybe we should have some fun with this little bitch, baby?" Talia had the same sly smile on her face that she had when he came into the room.

"I imagine if we ran the same report on your personal laptop we would find more of the same?" Rob asked.

Henry just bowed his head and nodded, instantly realising he had used the company WIFI several times on his personal laptop.

"And I also imagine that what's on there and your phone, could make life a little tricky for you if it got into the hands of say, your family and friends, or it accidentally got posted to your social media?"

"What!? No please! Please don't," Henry pleaded.

"Talia has all of the contact details of your family, so if you don't play ball, they may just get an anonymous message of how their youngest son likes to wear women's lingerie and pose while men jerk off to him."

"Please, please don't,'" tears started to well in Henry's eyes.

"Oh, would you look at that! The little sissy bitch is all upset," Talia sniggered.

"This arrangement needn't be all bad for you Henry, we will make sure you get plenty of pleasure from it, perhaps just a different type of pleasure to what you are used to!" he chuckled to himself.

"Talia honey, show henry how this can be pleasurable for him if he cooperates."

"Yes, daddy!" she replied.

Daddy?! Henry thought to himself.

Talia stood up and pulled the tight white sweater over her head, revealing a scarlet red lace bralette, henry instantly recognised it, it was part of his favourite set that he'd bought her for their anniversary last year, he knew it had a matching lace thong and instantly wondered if she was wearing it.

She pulled a hair tie from her wrist and tied back her long curly hair into a hair ponytail, then she slowly lowered herself between Henry's legs, looking up at him with her beautiful doe eyes. She rested her head in his lap and his cock immediately started to twitch, she had always had that effect on him. As she leaned forward, he could see the top of the matching red thong poking out from the waist band of her tight leather trousers, this made his cock grow even more.

"You remember this baby," she whispered in a seductive tone, "you remember how much you loved my mouth?"

As she spoke, she started to unbutton his trousers and slid them down his legs along with his underwear. His cock sprung to attention.

"Someone hasn't forgotten me," she giggled.

She ran her red manicured nails up and down his shaft before taking it in her hand and slowly jerking it.

"You like that baby; you want me to taste you?"

Henry couldn't help himself, this was all he had wanted for the last 6 months, to be with Talia again, to touch her toned body, to feel her.

"Yes!" he blurted out, "yes, please suck my cock."

"Oh, this thing isn't a cock baby," she continued to stroke him while speaking "this is a little clitty, my fiancé has a real cock!"

The insult stung henry but the pleasure was too much for him to give it too much thought. On the other side of the desk, rob was unbuttoning his suit pants and pulling them off, he laid them neatly on the desk making sure not to crease them and took a seat in his chair. He started to rub over the top of his tight white Calvin Kleins, Henry could already see the outline of his cock, it looked huge!

Just as he was staring at Rob's growing cock, Talia took his entire length deep into her wet mouth, Talia had always been amazing at giving blowjobs and she clearly enjoyed doing it. She bobbed her head up and down on his shaft, using her hands and slurping up the precum with each stroke.

Henry was in heaven, he felt pins and needles rushing all over his body at the familiar pleasure he was experiencing, and he closed his eyes and leant his head back. Moaning with every stroke...

He didn't see Rob stand up at this point and remove his underwear, his big dick hanging heavy between his legs, he took it in his large hands and started to stroke. As he did, he made his way round the desk and stood right next to henry.

Henry felt Robs presence and opened his eyes, his bosses 9-inch member was right in front of his face.

"Stroke it sissy," rob commanded.

"What? No!" henry replied.

"Honey!" as Rob spoke, Talia stopped everything she was doing and rocked back on her heels, no longer touching Henry in any way, his hard cock stood straight up and glistened with Talia's saliva.

"Pleasure comes at a price sissy!" rob continued, "We can stop right now, and Talia can start sharing those images if that's what you would prefer?"

"No, no please," henry reached up and grabbed robs shaft, it felt so warm in his hands, he slowly stroked it back and forth. What was he doing!

"Good girl," said Rob patronisingly, "honey you can continue."

"Yes, daddy," Talia said as she rocked forward and swallowed henrys cock whole once more.

Henry stroked Rob's cock, very apparent that it was only inches from his face. He could smell his musk; it wasn't unpleasant but certainly not something he was used to. As he stroked, rob started to moan, "That's it sissy, stroke your daddy's cock."

The head started to glisten with precum, and henry looked up at rob, rob nodded down at henry "Taste it slut!"

Henry had often thought about what it would be like to have a real cock in his mouth, but he'd never thought it would happen, he was quite happy to have his secret sissy life and that no one would be any the wiser. But now there was this huge cock right in front of him, waiting for him to suck it.

Henry continued to hesitate.

"Hon....." Rob was in the middle of getting Talia to stop, when he felt henry slide his mouth over the tip of his length. He moaned loudly in pleasure as he felt henry run his tongue around the tip.

Henry could taste the precum on his tongue, salty but also sweet. This spurred him on, and he hungrily lapped at robs member. He couldn't get that much of his cock in his mouth due to its size, so he stroked the shaft at the same time, to make up for it. He got faster and faster with his hands, trying to keep to a rhythm as he knew that's how he liked to be sucked.

"That's its slut, keep going like that and you'll make daddy cum," Rob moan breathily.

He could feel Rob's cock swell in his mouth, he places his other hand on robs balls and felt them tighten.

"Yes slut, I'm getting close," as rob said that henry looked up at him and saw Talia, she was standing next to Rob, he had been so focused on sucking Rob's cock that he hadn't noticed she's stopped sucking his.

"Cover this little faggots face daddy," she said has she pulled him in for a deep kiss.

That sent rob over the edge and henry felt his mouth fill with rope after rope of hot cum, some of it spilled out of his lips as he tried to control the torrent.

"Oh fuck!" Rob exclaimed as he emptied his balls into henry's mouth.

"Did you like that daddy?" Talia asked biting her lip seductively.

"Not bad for a first try, a long way to go to match you, my love."

Henry's heart sank as his lust subsided and he came back to reality.

"Pull up your trousers sissy and get out of my office, I need to satisfy my lady." Rob scowled.

"Actually wait!" he exclaimed, a devilish grin spreading across his face, "You wait there for a second, I want you to know exactly what I'm doing in here, while your sat in your tiny little office."

"Honey get ready for daddy's tongue."

"Yes daddy," Talia replied as she removed her boots and slid the tight leather trousers down her beautifully toned legs. She stood in front of henry for a brief moment wearing only the red lingerie set he was so fond of, his cock ached as he pulled his underwear back on.

She removed her thong and lay back on the desk, opening her legs, giving them both a perfect view of her glistening pussy complete with clit piercing. "Come get me daddy," was all she said.

"Out!" Rob pointed at the door and looked at Henry. "We'll be in touch about the next step of your service."

As Henry closed the door, he could hear all so familiar moans that Talia used to make when he went down on her.

What on earth had just happened he thought and what else was to come?

He skulked back to his office and closed the door; he couldn't stop thinking about what Rob was doing to Talia just down the corridor. Her body writhing on his desk with Rob nestled between her long legs.

The Knock at the door broke him from his thoughts.

___________________________________________________________________

Ana nervously stood, almost tottering on her heels, she straightened her outfit in the full-length mirror next to the bed and walked towards the bedroom door.

She took a deep breath and pulled the handle towards her.

To be continued...