Josie Date 2, Part 3: The Chapter Where the Master Finally Gets Laid

Scarlet

Daphne is huffing, apparently overexerted. Of all the humiliations she has suffered today, being lugged around by the mermaid wasn’t the worst. But carrying both of the fighting women at once was obviously too much. The fish dragged us to the bathhouse. She making it a point to stay between me and the bitch that fucking **** me into doing... that.

Daphne summons a spear out of nowhere and stamps it on the marble floor. Her clothes also disappear. “Ok, three ways we can handle this. The dumb human way would be to civilly talk through the issue over Honey Ginger Salmon Ice Cream. The proper mermaid way would be wrestling and I found this really cool item in the shop for wrestling purposes. The compromise way would involve a dip in the pool. How are we wanting to do this?”

Salmon flavored ice cream? What is the fish tripping on?

The bitch speaks first, “This item, what is it?”

“Ooooh, Dinah is voting for wrestling,” Daphne drools, “It’s a sponsored item from this place called Cum Guzzlers? I don’t know what a breastaurant is, but the concept is intriguing. Anyways, here is the item description.”

A Kiddie Pool of Customer Cum: Exactly what it says on the tin. A plastic kiddie pool filled three-quarters of the way up with the cum of various Cum Guzzler customers (of various qualities and freshness). This item is sponsored by Cum Guzzlers, the multiverse’s most perverse breastaurant! 10 BP (First one free for Tina).

“No way in hell are we wrestling in a kiddie pool full of cum!” both yell simultaneously.

Daphne looks disappointed, “But then I can’t drag you to the edge of the pool, jump in, get my mermaid-ness back, and lick up the remnants.”

“Why are we listening to the fish right now?” the bitch asks, turning to face Scarlet.

“’Cause she has a spear and knows how to use it, bitch.”

“Fine, middle choice it is. I am dragging one of you into the water at a time. You’ll tell me your side of the issue, then I will cast judgment. Tell me who’s going first.”

Scarlet checks her phone. She shows Daphne the text notification, stating, “I got a thing I need to do for Josie’s date right now. You can listen to her lies.”

She orders the breast transformation that they discussed during Josie’s pre-breakfast date planning session. By the time she’s done, Daphne is beckoning her to get into the warm scented bath.

Scarlet tentatively wades into the shallow end of the pool. Daphne wraps her arms around Scarlet’s neck. The mermaid is certainly intimidating in her own element. She leans in the whisper in the redhead’s ear, “So, remember the telepathy thing we did during the challenge? Well, it only works when we are close to each other while completely submerged. I can provide you with air for a bit, but it’s not super healthy for either of us for me to be breathing for the both of us. So, precision is important. Don’t waste time with lies or embellishments. Just answer the questions. ‘K?”

Scarlet nods, then feels Daphne lean back and pulls both of them to the deeper end of the pool. Then, she swims down. The warm, scented water fills her senses. Then the sensation of Daphne’s lips pressing hard on her mouth. It’s somewhere between a very hard kiss and the mouth position one uses to give a rescue breath. She feels Daphne in her mind, “When you want a breath, pinch my egg extractor. Understand? Remember to think hard.”

“Understood.”

“So, in brief, what happened.”

“Asked Dinah to give me a trigger. She added to it without permission. And it was embarrassing.”

“Embarrassing? What did she add?”

Scarlet pinches Daphne’s nipple as she answers. She tastes the fish flavored air fill her lungs as Daphne moans into her mouth. “She made me masturbate in front of Francis. Naked.”

“What’s the big deal about that? I’m naked all the time and I masturbated in front of him. Even teased him the whole time with telepathy. My Beloved being with me made it feel even better.”

“Focus. Remember that humans have this feeling called shame?”

Scarlet only picks up the mental equivalent of TV static until she pinches Daphne’s other nipple. Another breath, this one staler. Scarlet thinks at Daphne again, “You good there, Daphne?”

“Sorry. Distracted by remembering this morning. Gonna think a spell more. This time on topic. I’ll let you breathe on your own. Feel free to play with my egg sacs while I think.” While the iron grip doesn’t relent, Scarlet feels her head lift above the water. She bears the bare bear hug, enjoying non-fish tasting air. After five or ten minutes of squeezing, she feels Daphne swim towards the shallow end. Once she knows Scarlet can stand, Daphne lets go.

“I have made my decision. Both of you are in the wrong. Now, you can either apologize or wrestle each other in the cum pool. Your choice.”

“What the fuck did I do wrong?” Scarlet growls, “She’s the one who violated my trust!”

“A number of things. Dinah tried to apologize and you decided to flip your lid instead of accepting it. Harem-sisters shouldn’t fight like that. And we both know how your temper can get the better of you.” The fish has the nerve to pause for emphasis. She then continues, “The bigger thing you did wrong was to assume you understood how the transformation works in the first place. This was the first time Dinah used it, right? The magic we, wait, sorry, they use is so primal that it is somewhat unpredictable. Now that we know that Dinah will give into the urges to use the spell when being milked, it is completely on her if she doesn’t disclose it.”

“Fine. Sorry.”

“I’m sorry for adding to your script, Scarlet. I really didn’t mean to.”

“Gonna apologize for the rest of it?” Daphne adds

“Sorry for trying to brainwash you into accepting my apology when you flipped out.”

“We all good now?”

The two relatively normal women nod.

“Great! Now who wants to teach me about how to enjoy my weird not-cloaca thing?”

Josie

Tina and Francis are sitting on his clamshell bed, as expected. As expected, they have gotten fully naked (though they were basically undressed enough for sex during the game). Tina is still lightly teasing herself; Francis looks both excited and a giant bundle of nerves. We’ll see which way this goes by the end. Josie popped over to the sex dungeon to grab some supplies; she tossed what she needed in a small pirate’s chest and carried it over to the bed. If Josie is honest with herself, the eagerness Tina hopped into bondage gears makes the gym wolf a little uncomfortable. She indulges her girlfriend, but doesn’t want to commit to that lifestyle all the way. And the way Francis is eyeing the chest of supplies makes her think that he is even more ****.

“So, as our resident expert on transformations, I asked Daphne about what counts as ‘group sex’. Basically, we all have to give at least one orgasm to everyone else. Transformation triggers count. So, 4 rounds of sexy time. 1 round of each of us in the middle. Then the grand finale. Tina, you’re in the middle first. Are you sure you want to do what you were planning?”

Tina gulps. “Yeah. I am fucking terrified that, if I don’t do this now, Vinny will **** me to do it tomorrow night on our date. Francis, I don’t want him to ruin our date, so, even if you are uncomfortable, please just let it happen. Okay?” She pulls out a lolly.

He takes it, examines it, eyes glowing, a bit. “How bad is this?” he finally asks.

“Pretty bad, from what we can tell. Mind control.”

“I’m keeping this one. I saw some of that this afternoon, so, if you swear that it’s not going to do lasting harm, I will allow it. But I’d highly prefer something less ****.” The candy disappears, presumably into his inventory.

She sighs, “According to our contract that I can’t read, the bastard can mind control me at any time. This is as voluntary as I can do this, Francis. At least until I’m strong enough to fry his dick off. So, forgive me.” She summons another lolly and declares to the camera, “This blow job is brought to you by Cum Guzzlers, the multiverse’s most perverse breastaurant. Even lesbos love licking lollies at Cum Guzzlers!” She pops the candy in. Josie watches Francis as his face shifts to one of horror. Then Tina starts to devour his cock.

“Francis, she’ll be okay. 3 of us were **** with them last night. She’ll come out of it. For now, tug her ears. Help me get her to cum.” Josie leans down to start lapping at Tina’s dripping cunt, slowly teasing at the moment. Always keeping eye contact with Francis. It takes a moment for Francis to start responding; Josie is afraid his guilt will overcome his desire to see this through. Soon enough, however, he starts to gently thrust deeper into Tina’s throat; he starts to play with her ears. Seeing he’s starting to get into the mood, Josie picks up the pace on her end. She inserts a finger into the bunny girl and teases her insides, kissing her clit, nibbling on her lower lips. Tina moans around Francis’ cock. Only sleeping with her for a week and I already know how to press her buttons. Man, commitment can be soooo fuckin’ hot.

Tina starts slamming down on Francis’ dick, finally getting her nose to touch his hairless pubis. She gurgles as she thrusts back and forth, harder and harder. Francis is pulling on her ears as much to try to slow the girl as he is trying to stimulate her. He looks worried. Josie, pulling herself off of Tina’s snatch, reassures, “She’ll be fine. Enjoy it.” He continues to fingerbang Tina as she checks in on Francis, slipping in a second finger in the process. Tina squeezes down hard on Josie’s fingers as she becomes a quivering mess. Josie can’t tell if Francis came before or after Tina, but he’s in the throes of an orgasm as well. Once Francis shoots his last squirt of jizz, Tina slips off of his deflating cock and sits on her knees, mouth agape. She stops moving completely. Shit. Not this again.

“Swallow.” he commands, firmly. She smiles and does so. Then she comes to.

Tina: +20 BP

Tina: +2 VP (Gave Master a Blow Job x2 bonus [first time contestant participant], 0.5x penalty [magically compelled])

“Eww. Eww. Eww. Eww. Gross. BRB. Gotta get something to wash this out.” Tina rushes out of the room. Francis looks deflated.

“Don’t tell me you would’ve preferred that happen tomorrow, Francis?”

He sighs, then replies, “No. Can they really **** her?”

“Saw her lock up like that after presenting lollies for Scarlet and me to sample. She stopped breathing. They can...”

“Got it. I need to do something about it.” Sensing Josie was about to object, he adds, “Not personally do something about it. Maybe the producer can help?”

“I mean, she offered,” Tina notes, with bottled electrolytes for the three of us, “Just don’t know if it’ll help.”

“Take her up on it. When you hit Level 4, we might be able to solve part of the problem ourselves, but she’ll be a much stronger asset.”

Francis downs a significant amount of electrolytes. Josie sips some as she digs into the chest. “Okay, Francis, you’re in the middle now. Before we sexy times you, I want you to put this on.” She pulls out a pink chastity cage.

Josie expected some resistance, but not of the nature she got it.

“Please, please lock this disgusting thing up. Or, better yet, chop it off. It doesn’t deserve to remain. Shut up. Josie, why do... No, you shut up, pathetic male worm. I am your superior! You should worship all women! If one asks you to chop that thing off, you do so with pleasure! Understand! Fuck you.” He starts to shake. Then, looking utterly defeated, he takes the cage and slips the ring of it to the base of his cock. “Are you sure I need to?” he stares at Josie, almost pleading.

“We figured that if you wear the cage, when you get conflicting signals like when we compliment your clothing, it would remove it by removing a physiological response. Something worth experimenting with, at least. Or is the voice...”

“Going to insist, now that someone suggested it? Yes.” He finishes slipping the cage on and presents the lock. Josie locks him up. “Throw away the key.”

“Tina, hold this. We’ll unlock Francis when we’re done and he’s feeling himself.” Tina grabs the key and plops it into her inventory. “Okay, Francis, do you want us to make you feel good. Feel good like a girl?”

He leans into Josie. “Yes. Sorry. The fucking voice...”

“I hate to stop, but we can if you need to.”

“Scarlet and I did some therapy today. Came to some initial conclusions. The voice is going to get worse before it gets better. If we actually want to kill it, we need to do this. And...” he pauses, not quite sure how to voice the thought, “and I can’t believe I’m saying this, but I want to be pretty. Need to be pretty. Not to please or to kill the voice. For Daphne. And for you, Josie. So, please, let’s continue.”

“What am I, Francis, chopped liver?”

“Am I still ‘future hot girlfriend’ in your eyes, Tina, or something more?”

Tina leans in and starts to brush Francis’ hair, “Current ‘work-in-progress’ girlfriend.” She kisses his cheek and he seems to melt in her hands. “Right, Josie?”

“Right.” Josie kisses his neck, going down his shoulders. She then starts to rub his nipples. He lets out a keening whine as he starts to palm his cage. Francis is waaay more vocal as a woman. I like it.

Josie spins Francis around and presses him in Tina, his head resting on one of the bonny bunny’s bodacious breasts. The bunny continues to stroke and tease his braids. Josie looks down briefly at Francis’ crotch and sees how it seems to recede even within the cage. She then starts to suck on one of his nipples, continuing to tweak the other. He moans, “Please, harder. Both of you, harder.”

Tina eagerly complies, yanking down on his hair as hard as she can, forcing his eyes to meet hers overhead. “Remember last week, Francis? When I asked you who’s a good girl?”

“Yes,” he gasps.

“Care to change your answer?” She gives his hair another solid tug.

“Fine. Josie’s a good girl,” he whines.

“Boo!” Tina kisses his forehead, then continues, “I want you to know that I think that you’re a good girl. And this isn’t a power play or anything like that. This is me praising you for taking our teasing so well. So, please, cum for us.”

Josie shifts herself to start nibbling her way to his ear, lightly pressing her leg into his cage, continuing to tweak his nipples as she goes, “Such a good girl. Look how pretty you did your make-up for us. How you took care of your hair. How big you’re going to let these breast nubs grow. So, please, cum. Cum all over my thigh. Mark me as your girlfriend. I think I...”

The sensation of wetness on her knee interrupted the thought. His cum oozes out of him. His chest starts to bud out into little breasts. Not quite A cups, but noticeable on his nude torso. His braids start to loosen up as his hair grows. Then the phone notifications start going off like crazy.

Josie: +8 VP (Brought Master to Orgasm [Nipplegasm] x4 bonus [first time both participants])

Josie: +4 VP (Brought Master to Orgasm [Praise Him!] x4 bonus [first time both participants] x0.5 bonus [assist])

Tina: +2 VP (Brought Master to Orgasm [Hairgasm])

Tina: +4 VP (Brought Master to Orgasm [Praise Him!] x4 bonus [first time both participants] x0.5 bonus [assist])

Francis: Identity, Interrupted Progress: +2

It takes a while for Francis to come to. Josie presses herself into Francis while he rides the orgasm to whisper in Tina’s ear, “What was that?”

“I like it when I’m told that I’m a good girl when I cum. I admit my insistence didn’t go great last time, but Dinah did give him the praise kink since then. Thought I’d try it again?”

Josie kisses Tina on the lips, “Follow the plan, rabbit.”

“I called an audible, pup. My cute wolf girlfriend needed the points.”

Josie carefully sets Francis down and takes some more electrolytes. She gives the bratty bunny a swat on her butt for the sass. They both enjoy it. Francis comes back to reality. “Wow.”

“Up for round 3?”

“Give me a minute.” Francis and Tina both replenish some fluids. “Gonna need another one of these after this, probably.”

“Alright. Tina, lay down on the bed, face up. Francis, would you be a good girl and help me undress?”

Tina happily complies for her part. She starts to rub her clit while she waits.

Francis is a little more hesitant. To be fair to him, part of it looks to be his confusion on how to take off her top. He leans in to whisper, “I’m going to try something, okay? Just let it happen.” He puts a hand on her shoulder then she feels a mental tug. Not resisting it, her breasts are freed.

“Hey, I liked that top.”

It’s back in his hands. Oh. Inventory nonsense. Laying the top down, he gets into a squat and starts to pull down her thong. Wow. He looks kind of cute on his knees like that. Can’t wait until we’ve got him perfect.

Josie steps out of the thong and proceeds to sit on Tina’s face. Tina starts to lick, so Josie presses the bonny bunny’s head away. “Well, Tina knows her role. Francis, hop on Tina behind me. Play with my ears. You have no idea how fucking amazing those eargasms are.”

Josie: +5 VP (Displayed Naked Slut Body to Master)

Josie lets Tina get to work. The blonde eagerly laps at Josie’s sex. Francis presses into Josie’s back and both of them moan. His budding breasts poke into her shoulder blades. Her tail pressed into his stomach. But she doesn’t start bucking on Tina’s mouth until he starts to rub her wolf ears. Josie feels a little disappointed as Francis leans back, but some subsequent tugs makes her brain go blank for a while. She continues to mindlessly rut, seeking more and more pleasure, her mouth agape, her tongue lolling out. Tina’s tongue slams into Josie’s G-spot. Josie howls, quivering in ecstasy. She then whimpers when Tina pulls out.

“Francis, she wants you to go harder than you do with me.”

Tina nibbles on Josie’s labia as Francis pulls, soo hard. The world goes upside-down as Francis stares into her eyes. He looks like he wants to kiss her, but is hesitant. Josie tries to unarch her back, but, her body all noodley from pleasure, Francis is too strong. She thrusts and grinds on Tina’s face, as that is all she can do in her lust addled state. With one final tongue lashing in her love canal, Josie lets out a howling orgasm.

Josie: +2 VP (Master Brought her to Orgasm [Eargasm])

When she comes off of the orgasm high, she finds herself laying down on the bed. Tina’s already gone to the bathroom, Josie presumes. Francis is laying beside her, brushing some hair out of her face. Wow, old man, you did amazing. Now to make sure you’re ready for the grand finale.

Francis

“Hey, girl, Tina giving us some privacy now?” Josie asks, still basking in the aftermath of her orgasm.

“No old man talk? Who are you and what did you do with Josie?”

That earns him a love slug on the arm. “Grand finale is going to be just you and me. Wanted to talk about it before we begin. So, Tina entertaining herself?”

“She took some lube and a toy from the chest and headed to the bathroom. Hopefully, she doesn’t spend the whole night buzzing herself in there.”

“She does need a good 10, 12 orgasms to fall asleep. We’ll check on her and shower together after the grand finale.”

That is concerning. “So, what is the plan?”

“Well, I did buy something for the date. Now, we are going to hopefully have fun using it.”

Josie gets up and pulls out a strangely realistic looking dildo. It’s flaccid, hot pink, and slightly twitching. There seems to be plus and minus sign embedded into it. Is that a...

Josie: -10 BP

Daphne: +1 BP (Commission)

“Daphne called it a PP. And it’s supposed to...”

“I know what they do. I just didn’t think it would have a physical manifestation. I guess the signs are there to set which way it works?”

“Got it in one, old man. Don’t interrupt. So, as an item, it does it’s thing by cumming inside the target. With your permission, I plan to plow your ass. Normally, I’m not a big fan of toys or anal, but I like helping my playmate out if she likes them. Amy loooooves it when I peg her. So, what do you think?”

Francis is stunned. His brain is in utter turmoil. On the one hand, the woman he has had a crush on for months is right here, naked save her high heels, offering to have sex with him. On the other, she has him locked in an embarrassing, deserved chastity cage and is wanting to put him on the receiving end of anal. Not exactly the way he would normally want to lose his virginity. On the third hand, the voice is forcing itself out and it is taking everything he has to keep it down.

“Francis, you okay in there?” Josie asks, brushing some loose strands of braids behind his pointed ears.

“Stop asking this worthless pathetic worm if it is okay. It is beneath your concern. Take it. **** that cock up it’s ass and make it less disgustingly male.” Francis grit his teeth and forces his mouth shut.

Josie drops the PP and wraps her arms around Francis. The feeling of her nipples pressing into his is starting to stir another feminine orgasm, but being held just feel so good. He lets out a moan and Josie leans back, still keeping her arms around his neck. She’s tearing up a little.

“Francis,” she begins, “You have been such a good friend to me and I’ve treated you like shit back home. I’m so fucking sorry for all of that. And, as fucked up as this is going to sound, being on this show has done me some good. I finally figured out why people commit. And how it’s good to actually love and be loved and all of that girlie shit. I know I’m not 100% there yet, but I think I’m finally able to fall for you. So, please, if you don’t want to do this, I’ll support you.”

She then leans in close, “And, as for you, you evil bitch living in my friend’s skull, I will tear you out and beat you to **** with a rusty spoon if you ever say something so awful about him ever again in my presence. Do you understand me!?!?”

“Thank you,” Francis whispers. Speaking up louder, he asks, “How do you want to take me?”

“As gently as I can. Tell me to stop, and I will. Okay?”

“Okay.”

Josie gets up and starts to grab the supplies she needs for this. She found a strap-on harness than will fit her thong transformation requirements. She slips it on and attaches the PP to the dildo mount. She asks Francis to scoot to the edge of the bed. She lubes up the PP and then considers what to do with Francis. “Hey, 2 different ideas. We can get you ready the normal way or I could spend some BP to make it easier. Have a preference?”

“Call me a coward, but the easy way.”

“Hey, I got pegged by a woman once. And I was thoroughly drunk. You’re being plenty brave. Check it before I buy it.”

Butt Slut Fun Kit: Insert the Butt Slut Fun Kit’s nozzle into the anus of your sex partner and squirt. For the next hour, the partner’s anus shall be clean, lubed, and extra sensitive. 10 BP (Temporary).

Francis gives it a nod. 5 minutes later, the order was delivered and a 3 inch narrow nozzle is being lubed up. Josie has Francis hold a leg lift to get the nozzle into his anus. She squeezes the bottle and the fluid rushes in. It feels cool, calming. Francis’ nerves start to settle.

Josie: -10 BP

His nerves start to pick up as Josie begins to get the tip of the PP into position. It feels strangely hot on his anus. He bites his lip slightly. Josie leans down and brushes some of his hair out of his beautifully androgynous face, asking, “Ready? We can still stop.” He answers by wrapping his legs around her waist and pulls her in. The tip slides in; he grunts in pain. Josie starts to push her hips towards his buttocks. The grunts of pain soon turn into moans of something closer to pleasure. He never quite gets to the point where he starts to enjoy the sensation. This is what it feels like to be stretched out and full? It’s... unpleasant.

Bottoming out, Josie waits a moment, letting him get used to it, checking in again, “Are you still up for this Francis?”

“Only way out is through.”

“Not a great answer to my question, but I get it. I’ll go slowly.” Josie starts to slowly thrust. She gets 5, maybe 10 thrusts in before Francis starts to ooze cum on his lower abs. Josie stops and pulls out, the PP dripping in lube. Francis feels his hips shift, widen slightly. Josie grins. Glad someone is enjoying this.

“Maybe a change in position? I kept my heels on for a reason.”

Shrugging, he shift to a tabletop position. Josie lines up the PP again, then thrusts. Hurts less this time. Still not fun. She pounds, a little harder, a little faster. She starts to pant. Francis, not sure exactly what to do other that just take it, tries to look back at the wolf-girl.

“Eyes up front!” she barks, grabbing a handful of braids to turn his head facing forward. A keening moan rips from him. “Gonna take advantage of these handlebars, Francis.” She grabs another handful and yanks back. Francis moans, loudly.

Josie starts frantically groaning, “I’m cumming, Francis. I’m cumming! Damn, this feels way too good. Not as good as using my fingers and tongue, but way too good. Cum with me Francis. Cum with me!” She thrusts as deeply as she can into Francis.

Several things happen all at once. Josie suddenly finds herself without the PP providing her stability in her position, tumbles forwards into the small of Francis’ back. If she wasn’t orgasming already, slamming her abs into Francis’ ass cheeks certainly sets her off. Francis’ head slums forward as his hair grows longer. He feels his ass start to grow and shape into something plumper, almost feminine. And the cage that was around his cock just falls off. He oozes all over it.

Josie: +20 VP (Brought Master to Orgasm [Anal Sex] x2 Bonus [Took Master’s Anal Virginity])

Josie: -10 VP (Master Didn’t Like It)

Josie: +4 VP (Brought Master to Orgasm [Assplay] x2 Bonus [First Time Master Participant])

Josie: +2 VP (Brought Master to Orgasm [Hairgasm])

Josie: +2 VP (Brought Master to Orgasm [Assplay])

Francis: Identify, Interrupted Progress: +2 (Maximum Level)

“You okay, Josie?” he finally asks.

She squishes his new ass meat as she sits up, eliciting a little whimper from him. “More than okay. You?”

“I’m fine, but let’s not do that again.” He tries to stand, wobbling a bit. Legs feel different. He starts to stumble, only to be caught by the wolf-girl. She scoops him up in a princess carry. He nuzzles at her breast.

“Let’s get cleaned up, then ready for bed. You were amazing today. I mean, you beat me 2 to 1 tonight.”

“You certainly out-sexed the virgin. Like that’s saying much.”

“Shut up, old lady, you did good tonight.”

“Oh, I’m a lady now?” Francis only half-teases.

“Of course. And I wouldn’t have it any other way.”