tagTransgender & CrossdressersFrom Her Ex-Boss to her Bitch Pt. 02

From Her Ex-Boss to her Bitch Pt. 02


The day had been excellent, and the end of it was looking up. Pete had thought he might get a bit of fun with Rachel, but now he knew she was a true Domme and now that he'd admitted to her his submissive leanings, it looked as though it was going to be a very interesting few hours. Bring it on, he thought.

Rachel looked at him as a predator looks at prey, he'd no idea what he was getting himself into. She would run rings round him and transform him stage by stage into her perfect vision of a submissive male sissy slut. Now he was hers to own and use, even though he just thought it was likely to be one night of fun. This was just where the journey started. Once he had started down this path with her, he was done for.

She put one arm around his shoulders and kissed him deeply, their tongues intertwining. He was shocked and worried that someone he knew from the conference would see. But his innate horniness got the better of him. He kissed her back passionately pulling her to him, clasping onto that fabulous booty and pulling her onto his rock hard cock.

Rachel had a simple plan, she wanted to get him as horny as possible, to ensure his barriers were completely down so that she could have her very wicked way with him. As she did this she reached with the other hand and pushed the butt plug in a deeply as she could making him moan into her mouth.

"Come on bitch, let's start your journey."

Like a puppy he nodded and as she took his arm in hers he walked excitedly with her. The range of sexual things he fantasised he might do to her was spinning in his mind. He hadn't completely grasped that it wasn't about what he would do to her, it was about what she would do to him and also what she'd force him to do very much against his will.

She led him outside to where the Uber taxi she'd ordered waited. She'd ordered a big black SUV with tinted windows. She got in the front seat again another little point of superiority. The driver drove them to her apartment and she got out. She had to open the door for Pete, she'd asked the driver to set the child lock so he couldn't get out when he chose, stripping his level of control bit by bit.

As she opened the front door to the apartment, he was seriously impressed by how smart and large the apartment was,, how on earth did she afford this on her salary.

"Wow Rachel it's lovely."

"Sorry what did you say slut?"

"Wow Mistress it's amazing."

"Indeed it is, having a number of rich bitch slut bois who provide for me, does allow me to live in the way I have become accustomed." What she didn't tell him was that she also earned from her bitches by whoring them out to some depraved local rich guys. Her clientele were a very discerning lot.

"Through to the lounge, strip off, fold your clothes and put them in the chest including the panties, make sure you have a good sniff before you put them in bitch and then kneel in front of that chair and I'll explain what is going to happen."

Half an hour had passed since he had pushed the suppositories deep into his pussy, the wax had melted releasing the active ingredient which was irritating his bowels and had been making him want to sit on a toilet for some time.

"Mistress please may I use the facilities?"

"No you may not bitch, do exactly as I said." The coldness was increasing in her voice every time she spoke, she wanted him to focus on her as his Mistress now, not as Rachel the girl he wanted to fuck.

"Yes Mistress sorry."

He stripped quickly and folded the clothes neatly, not wishing to get punished. He piled them in the chest and finally took off the black lace panties placing them over his nose and breathing in deeply, repeatedly, loving the musky, faintly pissy aroma, mixed with the smell of his sweaty balls.

He didn't realize that she'd come back in and was watching him sniffing her panties with such gusto.

"You dirty little whore, sniffing at my panties. Now kneel as I told you to."

He wanted to respond that she'd told him too, but didn't want to make her more angry.

He placed the worn panties on top of his clothes and knelt as instructed. "Sorry Mistress."

"So you fucking should be slut, now, legs as wide apart as they will go, hands on your ankles please."

He assumed the position as she closed the lid of the chest locking a large padlock in place, then taking the key and putting it on a chain around her neck.

"OK slut here are the first requirements for you, you'll need those clothes to go home in, but you have to earn the key back by carrying out come challenges, some of which you'll like as you're a dirty little slut. Some of the other more demanding challenges will genuinely stretch you mentally and physically, really stretching your limits and what you think you are capable of. If you want to back out, now is the time bitch, last chance?"

"Once we start there is now going back, I will have you doing more than you've ever done, before the morning arrives. Consider this carefully as you will be forced to do a great many things you don't want to, if you decide to go on."

He didn't want to back out and so stayed silent.

"So which is it to be, leaving now or going the whole hog, boots and all?"

"The whole hog, boots and all, please Mistress." No hesitation, his cock was so hard he needed this now, he couldn't have gone back to his hotel without at least trying, as she knew he wouldn't be able to, he was too far gone with lust. His aching sexual hunger had to be satiated now.

She picked up her phone and used the video mode pointing at his kneeling naked body, "OK, now slut tell me that you want to be my slut and that you will serve your Mistress in any way possible, beg me to use you or we're finished right now."

This was dangerous, she'd have him on camera, then again he thought, she's already taping and I'm kneeling here naked with a raging hard on, what the fuck, he thought. Others would think he was mad at this point, but Rachel knew that a horny, drunk and heavily poppered up sub sissy is extremely malleable.

"Please Mistress make me your whore slut, use me as a bitch and train me to take more than I've ever taken, I beg you, fill my pussy and mouth with your strap-ons, make me lick you and worship you."

"Ummm not bad for a first time, you'll get better and ask for more and more depraved things as time goes on."

"Now before we start I think you need a drink, we have to crack on, so drink this as quickly as you can." She passed him a large tumbler full of Gin and tonic, made by Claire with 6 shots in it. She chinked her glass with his and they both downed them quickly, his reaction to the strong gin not surprisingly much more noticeable than hers to her water. The drinks did look the same though.

"That's better, nice and relaxed. Now stand up slut."

He stood and she placed a tight blind fold over his eyes and fed him some long sniffs of poppers. "Time to get your pussy clean and you looking a little more presentable."

She took him by the arm into a bathroom and guided him to sit on the toilet, with the seat raised so he sat directly on the porcelain, again another little point of subjugation.

"Take this bottle of poppers and keep sniffing hard, fill your lungs and soak your brain in them. Pull the plug out and then empty your bladder and bowels as much as you can."

With his right hand he reached in to pull the plug out whilst feeding himself poppers with his left hand.

The plug was well dried in his slut hole, with no real lube it took a while to break the seal and get a little moisture on it to release the plug.

He held it out in front of him and it was taken from his grasp. He heard it being dropped on the bathroom floor in a corner.

As soon as it came out the slime created by the suppositories oozed out, his relaxed sphincter (thanks to the poppers) incapable of holding the contents in.

She then handed him the shower shot (an smooth cylindrical aluminium head with holes at the end attached to the long shower hose) and told him to push it as far into his pussy as he could. Once he'd done that she let the water flow, instructing him to hold it in until she gave him permission to evacuate again.

She slowly filled him up with warm water as he began to groan and then he heard her turn the tap off and she reached in to hold the hose, telling him to clench hard.

As she withdrew it a trickle of water escaped from his pussy, but he managed to stem the flow as he clenched as hard as he could.

"Great now hold that water in and then we'll repeat, now let's see what we have to work with. I can see that you shave your balls that's a good start for a sissy."

It was the first time she'd used the word, so far they'd just talked about being a bottom, apart from making him wear the panties. He guessed this was just another facet she enjoyed, who was he to argue.

"Good big balls and so soft." She cradled his balls in her hand making him moan and then tightened her grip. "And that lovely small cock, perfect size for what I have in mind."

He was in heaven now, loving being under her control, loving the constant humiliation, having his balls in her control, in her hand was wonderful. Even though just a few hours ago she'd simply been an attractive ex-employee, now he was putty in her hands. The pressure in his ass was building up and becoming very uncomfortable.

She reached under his balls and felt around his asshole.

"Hmmmm not so good at shaving you pussy, are we slut, time to put that right. A good Sissy slut has to be perfectly smooth for her betters." He heard the cap come off the bottle and knew the smell of depilatory cream from when his wife had used it. He felt her slather cream all around his asshole and over his balls and then some above his balls. He wanted to say that he never shaved above his balls but thought this was a time to stay quiet.

He then felt her stand and heard her wash her hands in the sink, then presumably she'd turned the shower on. For that he was grateful, the cream was beginning to sting now as he'd knew it would, as it did its job.

"Now you can let the water out of your pussy slut, clench and unclench over and over until no more comes out." After a couple of minutes he was empty.

"Ok now take some more big hits on the poppers and here's another drink, this time you can have a wine."

He wasn't sure when she'd had time to get the wine and now he was feeling high, drunk, light headed and horny all at the same time, a very heady mix. She put the heavy wine glass in his hand and again he drank the drink in one go and she took the glass and placed it on the side. She didn't even have water this time.

She walked him forward into the shower again giving him the head of the shower shot, this time though warm water was flowing constantly.

"Ok slut wash off all the cream, really use your hands to make sure all of it and that horrible hair is gone. Then kneel down on all fours facing away from my voice. He did so and felt the now clean butt plug in front of him.

"Good you've found that plug, wash it off, we might need it again." Once he'd washed it off the water was turned off.

He then felt her push the shower shot in him once again, and then the water began to flow, but this time it was cold, very cold.

She was massaging his belly hard and his cock was still stiff and she caught it with her arm every few seconds, if only the water was warm he thought.

"Ok now squat on your heels and you can expel the water again."

He gingery got to his feet facing Mistress, the water was still cold and she was pointing it straight at his cock, which was having the desired effect and shrinking what little manhood he had.

He let the water out and she told him to stay in that position for a few minutes ensuring that every last drop of clear water was out of his pussy.

She got him to stand again, and this time he was more and more light headed. She had him bend forward and again filled his ass up with very cold water and allowed him to squat and expel.

"There we go, a clean, soft, hairless little girly slut ready to be dressed." Each time she used more and more feminine language, but then again so long as he got fucked in the ass he didn't care what she said.

She dried him off with a soft towel, making sure his crack was perfectly dry, then his balls, legs and finally upper body.

"Ohhh look at you, that's so much better, now we really have the making of a fetish slut, just as I knew you would be."

He was proud to think that he'd make a good slut for her, but he wished the preparation would be over and that he might get to worship her pussy or see her with a strap on between her fine strong thighs.

She handed him the bottle of poppers to take another two long sniffs then led him to another room across the hall and sat him in a chair.

"Sit there and wait for me, I'll be a few minutes, on no account take your blindfold off, I will know if you do and the punishment will be extremely harsh. Oh and top up your poppers slut."

He was too far gone, to even think of disobeying, drunk, horny and high, just as she wanted him. Suddenly there she was in front of him, he hadn't even heard her come in, but he could smell her arousal so close to his nose. Losing his sight had accentuated his sense of smell it would see, jeez she smelled seriously horny. God this was going to be a lot of fun.

"Now this might come as a bit of a shock to you, but I absolutely insist on the more suitable of bottom my bois to be fully transformed into sissy sluts. In my mind you're one who definitely fits the sissy profile. I'm quite sure you've been sissified before, nod your head if you have."

He nodded.

"I also know you loved wearing the panties, but you need to know that I'm going for the full sissy fetish look. Now we both know you have no choice in this, I've got enough damning video of you to edit together a complete film for your wife. It will show how you held my waist earlier and flirted with me, Claire did some taping when she went to the loos. It will then show you arriving here, stripping on command and sniffing my panties as you took them off."

She let this sink into his addled sissy brain. Fuck there was nothing he could do, he just had to go along with this."

"Can we agree that should your wife see that film, then your life would be over?"

He hung his head "Yes Mistress Rachel it would be over, completely."

He finally realized that whatever she wanted she would get, now he had no choice. His need to be fucked now also meant he'd have agreed to anything she commanded in the state he was.

He could tell from her voice that she was now kneeling in front of him. He felt her lift one leg and rest his foot on her muscled thigh, even the feel of his foot on her rock hard thigh was a turn on. Then he felt the unmistakable and exquisite feel of stockings going over his feet and up each thigh. When she'd put the other one on his cock was standing to attention again.

"That little fella of yours won't settle will he, still pathetically small though, we'll have to turn it into a clit soon anyway, then it won't be any bother."

As she described his cock as pathetically small, it twitched at the humiliation. She knew he was sinking deeper and deeper into her clutches.

What on earth did she mean he thought, turn it into a clit? Was she just using the female name again as she did when she called his asshole his pussy, just heaping on a little more humiliation, or did she mean something more. Then he felt an ice sleeve being pulled over his cock and having an immediate shrinking and softening effect. The poppers no doubt helped with that.

She put each foot into the leg holes of some sort of garment, which felt like it was either heavy PVC or maybe leather, this was pulled up to his knees.

He felt a womans shoe being fitted to his right foot, then heard the click of a padlock being closed on the strap of the shoe which was tight around his ankle. As the foot was placed on the floor he realized this was a very high pair of high heels. Then the other foot and another lock of a padlock, now that was 3 keys he'd need to earn back.

"Stand up carefully slut, I'm not sure how good you are on heels and these are 5 inches high. So be careful."

Using the arms of the chair to help him stand, he got to his wobbly feet and she cajoled his balls into the cavity in his body to hide them and then pulled his small cock back between his legs. She stood to his side, her right hand holding the end of his foreskin and pulling his cock between his ass cheeks, her left hand holding his balls up inside his body cavity. She held these tightly in as she instructed him.

"Pull the body up tight over your waist and so it sits tightly in your crack."

He did this and she carefully extricated her hands from his nether regions, his balls and cock firmly held in place by the gusset.

She hitched it up tight and then took one arm to fit into it, then the other, pulling the garment up and over his broad shoulders. It was tight enough that just getting it over his shoulders was a struggle, but the reason she loved that was it held the crotch very tightly between his ass cheeks. Holding

She zipped it up the front half way then pushed and pulled his man boobs into the right position before zipping it up fully. Then he was firmly encased in very tight black PVC. The neck of the garment was high and once she'd fiddled with the zip at the front she tightened a thick collar around his neck and again he heard the click of a padlock. finally a 4 or 5 inch thick belt was tightened so tight it made breathing hard, she'd used her knee in his back for purchase to tighten it as much as she could.

"Breathe out slut one more notch to go."

She obviously managed to get the notch as she pulled even more breath out of him, now all he could take was short girly breaths. Then again the ominous click of a padlock this time on the belt.

5 keys and counting.

She had him sit again and then she turned the chair round. It swivelled, but he had no idea why she had done that.

"Keep your eyes closed at all times now slut. I'm going to make your face up and don't want you seeing until I've finished."

As she took his blindfold off he did as she instructed and felt her work on eyeliner, mascara, eye shadow, blusher and lip stick. After she put on the lipstick he felt his lips begin to sting. Then the final touch a wig was fitted to his scalp.

The chair was swivelled once more and she asked him to stand.

Once he was steady on his heels she said. "Open your eyes now my darling and look at what you have become."

He did so and stared into a full length mirror which he now faced. He or possibly more accurately now, she was amazed, the tight PVC Body accentuated his curves and the belt held the bulges in place, no trace of his package remained.

The high cut of the legs didn't show any stray hairs, she'd obviously been careful with her use of the cream. The makeup was heavy but well done and he looked as though he wouldn't have been out of place in a hard core fetish movie. His lips were visibly swelling, he hadn't heard of lip plumpers, but Rachel had.

In fact he loved how he looked. Now they could get on with some action he thought. He looked at the high heels he was wearing forcing him to push his ass out obscenely, it looked as though he wanted to be fucked where he stood. That thought made him smile, as that was exactly what he wanted, a nice big strap on and soon.

"One more glass of wine and we can begin." He turned his head to her and was rewarded with his first look at Mistress, ohhh my Lord, she looked fucking amazing.

Her big body tightly fitted into a stunning black leather corset, giving wonderful cleavage even with her small breasts, her large erect nipples sticking out of the top of the half bra cups on the corset. How soon might he get to nuzzle on them. Thigh high PVC boots with heels similar to his, stockings underneath and then as he looked down, the sight he was so, so very happy to see, her completely shaved pussy, lovely lips ready to be worshipped. He longed to get to his knees and bury his face in her pussy. He could smell her and see that her pussy lips were moist.

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