Covid 19 - Pete Turned into Charleigh Pt. 03

"But a man Mistress, a man? I'm not sure I can do that."

"You just said you'd do anything, you've been filmed savoring 5 different shots of cum on cam today. You chose the cum you liked the most, what's another shot of cum?"

If Pete had been there he'd have rebelled, but Charleigh was in charge now, "Sorry yes Mistress, what do I have to do."

"My lovely Scott has installed a Glory Hole training box, just for you, inside the door as we came in, you probably didn't notice it as you tottered in. It's custom made and allows me to secure you in, so that if people pop in they can make use of your holes."

"Ohh my, not both holes Mistress." Charleigh was truly frightened for the very first time since she'd been found by her wife, earlier that day.

"Not this afternoon, no, but in time, yes both holes, that's what good sissies need to do."

"So follow me to the door and let's get you ready for your first ever customer, ohhhh how exciting is this. Make that ass of yours sway and make sure it gets you in the mood." Red picked up a 12 inch black dildo and a thick leather leash as they left the dungeon.

As they moved back along the dimly lit corridor, Charleigh saw the box just inside the lobby way, when she'd entered the dungeon earlier that day she'd not even noticed it, but now she could see that it came just above waist height and was made of wood painted the same dark color as the walls, presumably so that it would blend in.

Red unclipped a padlock from the heavy clasp and lifted the lid of the box, Charleigh looked in to see a range of attachment points, the box was sitting on a large concrete shower tray with a drain in the middle. What looked to Charleigh like a vaculock attachment for dildos was set in a slot in a metal grove fixed onto the shower tray floor. It was immediately clear to Charleigh that the position of the vaculock could be moved. On the front wall Charleigh saw the unmistakable Hole, cushioned on the inside to prevent the sub from damaging it's head or face. She didn't have time to take in the other refinements, her mind was pretty scrambled with what she'd seen already.

"Ok sissy, first the kneeling cushion and then I'll get a nice big dildo in place for you, I want you to be able to fuck yourself while you're in here, we wouldn't want you to get bored would we, you might be in here for some time. Then you can see your first customer and I can get on with some more arrangements for your stay. I'm not sure when your date will come by, but not knowing when just adds to the fun doesn't it. Just give me a moment to fix this one in there." Red leaned in and slotted the vaculock dildo in place.

"Now bend over and we'll get your plug out and you can squat onto this lovely big cock of a dildo and get yourself comfortable and I'll get you all fastened into place."

Charleigh bent over the box, Red rotated, and wiggled and pulled on the plug eliciting moan after moan from Charleigh until it finally came out and Red put it to one side.

"I think your pussy looks nice and lubed up, it should be enough to get this big cock in that dirty slut hole of yours, but let's see, I want you to squat over it until the tip is in your asspussy and then carefully kneel down onto it bit by bit, don't want you to have an accident do we, then we can adjust the position if we need to slut."

Charleigh carefully lifted her leg over the side of the box and gingerly stood on the slippery floor in her high heel, before lifting the other leg over, she faced the hole and held onto the sides of the box as she slowly tried to line up her asshole with the dildo head.

"Come on slut faster, we haven't got all day, ohh well we have, but your date is waiting desperate to see how good that mouth is of yours."

Charleigh loved bondage and being restrained by her Mistress but this was extreme, even for her. She wasn't sure she could go through with it, but the ball gag made arguing impossible. Then she got her encouragement. Red struck Charleigh on her bare ass cheek with her riding crop. "Hurry the fuck up slut."

Red bent and reached in lining up the thick dildo head with Charleigh's hole and as Charleigh lowered herself, Red rubbed it up and down Charleigh's crack until it lodged just a little inside her still open hole.

"There, it's in, lower one knee to the pad and then take at least 6 inches into your whore hole and then lower the other knee."

Charleigh carefully did as she was told and was then on her knees with just 3 inches of the cock inside her.

"Ohh come on Charleigh you can do better than that, your mouth is too high, sink down so the back of your thighs meet your heels please." Charleigh did so slowly, this was a huge cock to take most of it in, but after a few times rising and lowering onto it, she was sitting on her heels. Red reached around and attached a clasp locking the back of each thigh cuff to the respective ankle cuff.

"There nearly done, that will make sure the cock stays deep within you and your mouth is at just the right height. Now for the final touches, hands behind your back."

Charleigh obeyed and Rd padlocked her cuffs together behind her and then clipped the leash onto the D ring on the front of her CUMSLUT collar and slipped the other end through the glory hole.

"Ohhhhh this is so exciting, your very first proper male cock. Now I want you to be really high for this so you'll see in the corners in front of you are two purpose designed holes for me to put two full bottles of poppers in them. Once the lid is closed, I'll slip a cover over the glory hole so that no fumes can escape and you can enjoy them before your date arrives. You'll be in sub heaven my little slut. Now off with the gag and I'll get the lid locked."

Red opened the two bottles of poppers and put then in the holes so that they would waft up to Charlies nose, then she took off the ball gag, dropping it in the box.

"Mistress, I'm sorry, I'm not sure I can do this." Pete was trying to make a comeback.

"Of course you can, and to be honest Charleigh you have no fucking choice, so shut up, or I'll make you regret it, get breathing bitch." With that Red closed the box lid and Charleigh heard the padlock lock into place, there was no escape now. A little light came in through the glory hole, but before Charleigh could get used to it that was blocked.

Now to wait. Charleigh thought the dildo was too big to cope with for too long, but she couldn't raise up more than a couple of inches as she was restrained. Her breathing rate rose as she got more and more anxious, taking in the poppers in the enclosed space. She closed her eyes and saw the spinning colours and dots and holes that she always did on good poppers. Soon she didn't really care what was going on, she was as high as a kite and now rather than trying to get as high as she could on the dildo, she was just riding it like a true slut. Red could hear her movements in the box, she smiled, once a slut, always a slut, she was sure her piglet wouldn't let her down.

Then again if Charleigh knew who her first customer was going to be she'd be having a fit right now.

Red moved through to the dungeon proper and rang the number. "Well hello Constable Stevens, as you possibly know I'm now in possession of the new slut we discussed, after you chased her today, that was priceless to be honest, she was shitting herself at the thought you and Annie would stop her in the car all dressed and trussed up."

"Just doing what you'd asked for, hopefully she was emotional when she got to the safety of your place."

"Haha, hell yes she was so relieved, she'd have agreed to anything. After you catching him on the way home from here, so perfectly a couple of months ago, she had little choice but to come and serve, so thanks for that and now it's time to pay you back. Normally a blowjob with her would be $20 but for you the first five are free and all future ones just ten bucks, as often as you like. And in time there will be a lot more alternatives for you. For now I don't want her to know who you are, we'll keep that for a fun reveal later. Ohh I meant to ask is Annie into any BDSM or not her thing?"

"Well she was pretty turned on by the whole transformation idea you told us about, but I think from what she's said she loves domination especially of men and I think she has a thing for watersports."

"Ohh how lovely, now one last question before you come over and try the wares, would the two of you ever fancy being involved in dominating her in the dungeon together?"

"Fuck yes, we're pretty open with each other, hell we'd love that."

"OK well come on round, there's a keypad on the door and I'll change the number daily for security, but let's start off easy, it's 1234 for you. Just come in, close the door, slide the bolt in place so you won't be disturbed, she's in bondage in a box and her collar is attached to a leash that is poking through the hole, use that to encourage her if you need to, but don't yank on it too hard as she is cuffed and so won't be able to protect her face. But other than that go for your life and let me know what you think after you've enjoyed using her."

"OK do you provide the condoms or???"

"Hell no, her stomach acid will kill off any germs and now it's her only source of protein so I hope you've not cum for a few days, she'll need all the calories she can get."

"That's awesome and yes I've got a few days worth of spunk saved up for her, but it sounds like I don't get to look her in the eyes?"

"Not this time no, but if you like it and want to maybe have some alone time in the dungeon with her or with both you and Annie, some time in the next four weeks, then you can look her in the eyes and do absolutely whatever you like with her, but that will cost a lot more."

She could tell he was on the hook, the free blowjobs were just to try and get some other sessions booked either for domination with her, or in this case for dominating Charleigh.

"How much?"

Red shook her head, why were cops always so tight with cash.

"Well, normally for an hour with me it's $350, if you want to be dominated by me with her in attendance it's $400, but for just using her it's only $150."

"And you said we get a discount on the normal prices, after all we forced her into your clutches didn't we."

"I don't know about forced, but yes you certainly helped me to get her. You have to remember It does tie the dungeon up, so this would have to be in the quiet times or evenings when it's not in use.So I can do it for you at $70 an hour, how does that sound?"

"It depends on what we can do in that hour? and what the dungeon is like?"

"OK, why not come round, open the outer door, bolt that and text me and I'll give you a quick guided tour to get your imagination running riot and then you can fuck her face thinking of what you'll do to her once you get her in the dungeon, how does that sound."

"Sounds fantastic, I'm on my way right now, I'll be there in ten minutes."

Red grinned as she put the phone down, this was too easy and all thanks to her new little slut. Her plan was really coming together. Even $70 once a week when the dungeon would other wise be empty was a good result.

She strolled down to the box and knelt down to talk to her sissy. She listened and could hear Charleigh's heavy breathing and her rising and falling onto the dildo, she was in slut heaven obviously.

"OK baby gurl time for you to earn your keep, your date is on his way and he wants to look around the dungeon first to see if he might be interested in you entertaining him in there at some time. So today you have to be the very best cock sucker you can be, it's crucial that you make him cum like he's never cum before, worship his cock like a whore."

"Yes Mistress Red I promise that I will be the best whore for you. Ohhhh god the poppers are soooo goooodddd Mistresss. I love them."

"Good that's my little sissy, I'll keep feeding them to you and we'll make you a better and better sissy with each and every day. Better in each and every way." A few hypnotic triggers couldn't hurt for the long term. "You just keep riding that cock and get your throat ready for it's treat."

There was no response apart from the gentle sound of her fucking her own asspussy."

A few minutes later she heard the car pull up, it almost screeched to a halt and then the firm knock at the door.

Red opening it and held her finger to her lips to make sure he didn't speak, she wanted the first blowjob to be a silent one to build it up in her sissy's mind.

She led him down to the dungeon, closing the door after the box behind her as they went.

He walked into the dungeon and stopped, his hands on his hips, "Well I never, this is fucking brilliant."

"So as you can see, a full wet room in the corner, you can do all the watersports of enemas you want there. Dildo's, butt plugs, strap-ons galore, I can use those on you, or you can use those on Charleigh."

"Ohh that's his name, sorry her name now, OK, more into using them on her, but you never know."

"Then my latest attraction is the Shockspot fucking machine, but I have to be present for you to use that, so that's extra, it is pretty insane though. There's suspension in that harness, then the sling in the corner, the bed, the bondage bench, the winch, so many possibilities, just up to your imagination. What do you think, worth the $70?"

"Hell yes, this will be the perfect way for me to take out my frustations, I think I may be a regular."

"Great as I say, my sessions largely in the day, so night time should be fine for your cheapies."

"What about when I finish a late shift at midnight?'

"Ideal, she'll be sleeping in here on the bed, so I can simply restrain her and she'll be waiting for you when you come in for your fun."

'When can I start." he was certainly eager.

"I want to get her a little more used to things first, how about on Monday." She could see he was disappointed.

"Or if you are desperate, how about tomorrow night, that will give me a little longer to get her used to the idea. I'm still not ready for her to know who you are yet so I don;t want her to see you or for you to give it away, but I have the perfect way to blindfold her, you'll love it. So what time tomorrow?'

"I'm on a late so midnight would be great."

"Brilliant, then I'll work her hard all day, get her shattered and you can come in an wake her and go for your life, how does that sound. Tomorrow, I'll be here to show you how to use the equipment, I need to protect my investment. Ohh and it's cash as you arrive. Now go and see if her throat is suitably accommodating." She could see he had a raging hard on, the tour had worked to perfection.

"Ohh I will." with that he raced down the hallway,

Red wanted to watch, but that wasn't fair, she'd enjoy seeing the condition her slut was in after her next lesson. It would be harsh, but she needed it.

Constable Stevens was desperate to have his cock in a warm cock sleeve, he'd always been a jerk with women and wanted to go at things harder than they ever wanted, a cop who chokes his girlfriend not being a good look, but now he had the perfect solution, for a small investment each week he could have his very own sex slave and the thought had him truly hot.

He closed the door and stood in front of the glory hole, he smiled and dropped his flies, then pulled his cock out, it wasn't huge, but at 7 inches it wasn't small either and what it lacked in girth the size made up for. He was cut and clean and his balls were heavy. He picked up the leash and wrapped it tightly around his right hand before knocking on the lid of the box. He moved the cover aside.

Charleigh had been away with the fairies before the knock but now she knew it was time for action, she opened her mouth and took in a few deep breaths to load up more poppers.

He pulled the leash until her bright burgundy lips were at the hole and he licked his thumb and ran it over her top lip, trying to be intimate before he fucked her face as hard as he could. He wanted to tell her she was a worthless sissy whore, but he'd promised not to speak, so his cock would have to speak for him.

He moved his hips forward until the head of his cock touched her lips, she opened still wider and moved forward as far as she could to suck the head of his cock. She had her tongue out along the underside of his cock and it felt good, but he wanted to be balls deep as soon as he could be.

He wasn't in the mood for a sensual blowjob, this was to be a face fuck and make no mistake. He thrust forward and held himself there, she'd managed to take 4 inches before he came to the back of her throat. He moved back and forth, getting her to lubricate his cock with spit and then going just a little deeper each time, her gagging stimulating him. he'd always loved the sound of a helpless woman, and found the sound of a helpless sissy just as much of a turn on. The fact he'd caught the guy for drink driving helped him to dislike this sissy, she'd pay for that. As she tried in desperation to move back from his invading cock, he pulled her forward with the leash until her forehead was jammed against the padding of the hole. He reached down and held her nose and he thrust forward once more, this time gaining access to her throat proper, ohh how good it felt.

This was the best, her helplessness turning him on to such an extent that he didn't last long, but he fully intended to deposit his load as deep in her throat as possible. He pulled her tight until he was balls deep and felt his cock unload into her. It felt so, so good, he threw his head back and savored the moment, holding her gagging on his cock as it continued to pulse and unload. When he finally let her go, his cock was spent, he was breathing hard, it had been quick but the fact that he knew it was the first of many, meant he was still happy. He did need a piss though.

He wasn't sure, but then again he hadn't asked the question although they had talked about Annies love of watersports, what the fuck he needed a piss. He pulled on the leash again and out popped the lips, the cum obviously having been swallowed. he let his stream go straight into her mouth, pushing his cock in a couple of inches. She worked hard to swallow it all, he tried to keep the torrent to a sensible level so she could swallow most of it, but some inevitably spilled.

Charleigh had gone to town on his cock, using all the tips she'd watched on sissy hypno videos, if she'd been asked how she would have responded to a man cumming in her mouth she thought she would have almost thrown up, but in her turned on and poppered state she had eagerly swallowed it down. She had crossed the Rubicon, there was no going back now. The piss hit the back of her throat and shocked her, but as Mistress Red had made her drink her own piss before it didn't seem too extreme.

When the Constable finished, he simply said "Good job whore." and with that he was gone.

Red had heard it all from the other side of the door, chuckling to herself. This was perfect the slut had done her job and would definitely be a money earner from here on, she might even be better than Red had hoped. Time to see what a state she was in. She opened the door, slid the outer bolt back in place and then unlocked the padlock and lifted the lid. There was her slut, lipstick smeared all over her face, cum and piss on her tits and sitting in a small pool of piss. Still impaled on the dildo.

"You did well baby, you really did well, lets get you out of there then you can do some more exercise so we work off that weight and then we'll get you cleaned up and ready for dinner before bed I think.