Summer Surprise Pt. 10

"Nonsense. Yolanda, show her how it's done."

Marty reached under her blouse and unclipped the snaps. Yolanda pushed the straps down her arms and pulled her bra out of her arm holes. "Ta-da," she said when she was finished, stuffing the bra in her purse. Marty kissed her.

"Do you need help with the clasp?" Karl asked, wiggling his fingers.

"I've got it," Rosilyn replied. "It's a front clasp."

"Perfect." Karl held the bag out and waited for Rosilyn to add her brassiere to the bag, then handed the bag to her. "If we fuck, I'll keep a pair of panties," Karl said. "One more thing I need you to do before we give our food orders. I need you," emphasizing you, "to put this inside your pussy." Karl held out the Lush.

Rosilyn looked at Karl. He remained calm, a slight smile on his lips. "We're just getting a little better acquainted," Karl said. "I want to know how badly you want to see the concert. You can give it back to me before you leave the restaurant."

There was no give on Karl's face. He waited patiently for her to take the Lush. Rosilyn took the device and spreading her legs under the table, inserted it into her pussy. She was surprised how wet she was and how easily it went in.

"There's a button at the end of the tail," Karl said. "Depress the button for three seconds and your work is done."

Rosilyn did as he requested. Nothing happened. The waitress, Andrea again, came and took their order. She didn't recognize Chloe either. Karl ordered champagne for the table. While the waitress was taking the orders, Rosilyn felt the thing inside her pussy start buzzing, well more than buzz; she was feeling some deep vibrations against her g-spot. She had trouble concentrating on the menu. It wasn't loud, but it was insistent and Rosilyn knew she was going to cum. She managed to get through her order and the waitress was taking Yolanda's when Roz climaxed. She squeaked, trying to hold her moan in, plus she knew her eyes were rolling in her head as her eyes couldn't focus on anything. She felt Karl squeezing her hand as she spasmed. The waitress left with their orders.

The champagne arrived and Rosilyn quickly downed two glasses. Karl began talking to Rosilyn as if it were a normal date, getting to know her, asked her about school, her major, her family, what books and movies she liked. Rosilyn found Karl to be quite charming and amusing when he wasn't acting like an asshole. She found the champagne really mellowed her out and she enjoyed the conversation.

When they brought the food, the devilish device went on again. Karl wore a slight smile as it went off. Worse yet, he put his hand on her leg and she didn't even notice until he was fingering her clit. She couldn't raise a fuss because the waitresses were there and it would call more attention to it. That made her orgasm even more explosive when it happened and there was more than a squeak. Indeed, there were several moans Rosilyn was sure they could hear in adjoining booths or tables. The waitresses definitely heard them, smiling as they went away. Rosilyn opened her eyes and Karl was licking off the fingers which had been touching her pussy.

"Definitely tastes as good as it smells," Karl said. Rosilyn blushed as Marty and Yolanda laughed.

The same thing happened when they took the orders for dessert, except Karl left it on. Rosilyn orgasmed three more times before she finished eating her dessert and was a wet mess before Karl turned it off.

When the bill arrived, Karl peeled off four hundred dollar bills from this huge wad of cash. He told the waitress to keep the change. It was a seventy dollar tip. Karl told Rosilyn she could remove the blasted vibrator and wipe herself off with her napkin. She pulled it out and handed it to Karl, who sniffed it again, before wrapping it in a handkerchief.

"I definitely know more about you now, Roz, and you know more about me. Do you still want to go to the concert?"

"Yes," Rosilyn whispered. "Please."

"Then you have one more thing to do for me and I'll take you to Madison."

"What?" This is when Rosilyn figured Karl would at least ask for a blow job or something, if not sex. Instead he pulled something else out of his coat pocket.

"These are Ben Wa balls. Tomorrow morning, before you go to class, you'll put these in your pussy. You'll send me a video of you inserting them. Then you'll take a photo of the little tab hanging out of your pussy every couple hours and send it to me. Obviously, it can't be the same photo. It will keep you stimulated all day long at school, so by tomorrow night, you may be looking for some relief. I want you to take a movie of you masturbating yourself and send it to me by seven PM. If you do all that, you can text me the address where you want me to pick you up. We'll need to leave La Crosse by four, so be ready. Pack some overnight clothes and something for Saturday. We'll be spending the night in Madison."

"Where?"

"A friend's guest house."

It was another twisted and sexual thing Karl wanted her to do, but at least it wasn't sex, so Rosilyn accepted the balls and put them in her purse. Karl gave her his phone number printed on a piece of paper and she added that to her purse as well.

"You'll love those," Yolanda said. "I've got some inside me now and they're marvelous."

Rosilyn nodded. Karl gave her another open mouthed kiss, lightly stroking the outside of one of her braless breasts as he leaned into her. She felt her nipples stiffen in response and knew they'd be poking out of her dress as she left unless she put her bra back on. Karl smiled and left. She watched him get into a top of the line Lexus SUV and drive off. Rosilyn hated to admit it, but she was beginning to enjoy what Karl was doing to her. She'd had five fantastic orgasms and he'd barely touched her yet. She supposed she'd be having more tomorrow.

******

When Chloe returned home, she went to her room, removed her make-up and prosthetics, took off all the clothes and hung them up. She'd need to find something different for Friday and Saturday, but she had plenty of time. Marty and Yolanda had sent her photos and movies they'd surreptitiously recorded when Rosilyn was cumming tonight. She went into the bedroom where it appeared Dianne, Sophia and Matt just finished a bout of fucking. All of them were a little breathless.

"Did Slut cum?" Chloe asked.

"Three times, Mistress," Dianne admitted.

"Has she been punished yet?"

"Not yet, we were waiting for you."

"Fine, she can get busy licking me while you swat my fine ass. I'll let you know if she seems to lose focus on what she's doing and we can add five swats every time she does."

Chloe got on the bed and felt her slave get between her legs and pleasure her to four glorious orgasms. Slut only needed five more swats during her spanking she was doing so well. When they were finished, Chloe showed them the stuff Yolanda and Marty sent her. She also told them what Rosilyn had to do tomorrow. They enjoyed thinking about what was going to happen.

******

Dianne got to wear a lacy bra on Thursday, but the shirt she had over it was damn near transparent, so what was covered by the bra was exposed by the shirt. It wasn't much different from what a lot of actresses and female singers were wearing, but they weren't wearing them in LaCrosse. It got some attention until everyone realized they couldn't see her nipples because the bra had an inner layer of nude fabric. She didn't have anything in her today, no plugs, Lush or Ben Wa balls, Bree still had to help put on her medicated cream. Every time Chloe received a text from Rosilyn, she forwarded it to Matt, Sophia and Dianne. Dianne would snicker a little, but delete the picture. Rosilyn deserved to be taken down a peg, but not have photos of her floating around forever, even if it was an anonymous pussy.

They were all home studying when Rosilyn sent the last one of her masturbating. Chloe showed them the video. Not only did Roz cum once for the camera, she climaxed twice, nor did it take her long to do so. Chloe deleted it after they watched it. Chloe received Rosilyn's address shortly thereafter.

"The hook is set, Roz is ripe for plucking," Chloe said. "I'll be fucking her after the concert."

"Are you sure, Mistress?" Dianne asked. "Once she goes to the concert, she could just as easily say fuck you and leave."

"First of all, she's going to wearing the Lush in music mode during the concert, which should prime her. Second, Fiona's contact says she likes to do ecstasy when ehe goes to concerts. Plus, she still needs to get home. I'm sure between those three things, she'll spread her legs. She wants to anyway. Karl is getting to her. Flashy, rich, snobby, just like her."

"Are you going to make her eat you out, Mistress?"

"Not until Saturday night when we go out drinking and dancing. I've already arranged a date for Matt with Barbara. Marty and Yolanda will also be there. You, Erin and Fiona will go together and be dancing and making out. We'll make fun of the gay bitches and eventually, I'll spring it on her she's been having sex with a gay bitch, which must mean she is too. Then I'll make her get between my legs and worship cunt. I'll probably make her eat you and Fiona too, since it was you she was rude to."

"How will you get her to do that?" Matt asked.

"I think she'll want to by that point; she's probably having the best sex of her life. But if she's still resistant, I'm sure she can be encouraged."

"I don't want to do anything illegal," Matt said.

"Nor do I. It won't come down to anything illegal. Slut, I think it's time you pleasure me again. Matt, you want to fuck our Slut while she's taking care of me?"

"Of course. I've been erect ever since we watched Rosilyn stroking one off."

"Excellent. I love it when a plan comes together. I wonder if I can get Rosilyn to play herself in my July play. Instead of a one person play, it will be two. I'll change her name so the only one who knows it's her is her. I wonder if she's planning to hang around summer semester or if she's going home?"

******

Friday morning found Dianne dressing in the nuns costume her Mistress provided for her. It was a regular nun's habit except the skirt was substantially shorter than a regular habit. Being led around the campus on a leash in a nun's habit raised a few eyebrows. The professors who originally questioned what she was doing had the same questions they had before, but despite the new costume, people were getting used to seeing her led around on a leash, so other than the initial stirring, she was largely ignored after the first few minutes.

"It's only one more week, I swear," Dianne told them. Realistically though, her Mistress would always be pushing her buttons, though perhaps she'd find other ones to push. She was certainly pushing Rosilyn's.

******

Karl picked up Marty and Yolanda first, gave them more instructions, then headed to get Rosilyn. She was standing outside her apartment wearing a perfectly acceptable party dress for attending a concert. Karl stopped Sophia's car, got out, grabbed her overnight bag and escorted Rosilyn to the car, kissed her lightly, then opened her door and helped her in. He put her bag in the trunk.

Yolanda slapped Marty's arm. "You see that, Marty. Karl is a gentleman. You don't hold the door for me anymore."

Karl got in. "That is true, Yolanda. I have other peccadillos however. Roz, are you wearing underwear again?"

"Yes," she replied nervously.

Karl handed her another paper sack. "In they go, however, because you didn't quite grasp the concept of how I like my women to be dressed, you can't pull your bra off through your sleeves. I want it taken off the old fashioned way."

"I'd have to lower my dress."

"You've got it."

"I'll be bare on top."

"Exactly." Rosilyn still hesitated. "I can stop and let you do it on the side of the highway, or you can do it in the car, or we can turn the car around. I won't lose that much time taking you back."

Karl started to veer to the side of the highway.

"Stop. I'll do it in the car." Karl started accelerating again.

Rosilyn had Yolanda help her unzip the back of her dress, lowered it to her waist and removed her bra. A trucker they were passing at the moment blew his air horn when he saw Rosilyn topless. She quickly pulled the dress back up, and put the bra in the sack. Yolanda helped her with the zipper.

"Panties too," Karl said, shaking the sack, still keeping his eyes on the road.

Lifting her dress, Rosilyn slipped her panties off and put them in the sack. Karl handed the sack to her and told her to stick it in the glove compartment. She could recover the sack tomorrow on their way back to La Crosse unless she allowed him to fuck her, at which point, he'd claim her panties and she could have the bra back. Karl reached into his pocket and pulled out the Lush vibrator again.

"Are you going to make me orgasm again on the drive?" Rosilyn asked as she inserted the mouselike device in her pussy. She was hoping Karl would. She'd enjoyed the ones she had in the restaurant.

"Not with that. The vibrator is for the concert. It has a music mode and it will vibrate in time to the music. I had a friend try it listening to both Prince and Taylor Swift. I think you'll get more of a kick out of Prince's music than Taylor's. If you're nice to me, I will let you orgasm on the drive, however."

"Do I need to give you a blow job?" She glanced at the two in the back seat. It wouldn't be the first time she'd ever had sex with someone watching, but it would be embarrassing.

"No, that would be dangerous to all of us. I'd hate to have to do without my cock the rest of my life if I had to slam on the brakes." Marty and Yolanda chuckled in the back seat know Karl didn't have a cock to lose. "You'd be nice to me if you'd spread your legs so I don't have to fight you to finger your pussy."

At least there'd be nothing for the two in the back seat to see. There was something dangerous about Karl. Not physical danger, she didn't perceive a physical threat. He didn't force her to do anything. Instead she was given choices. Do this and you can go see the concert. Don't and you won't. Spread your legs and you can orgasm on what would normally be a fairly boring drive, while people watch you cum. Having the climaxes in the restaurant, though they'd humiliated Rosilyn, had also been some of the strongest she'd ever had, maybe the strongest. This had the same feeling of danger and excitement, the sense of living on the edge. She spread her legs. Karl nodded.

"Good girl," he said before running his soft hands up her thighs. Hands that felt as if they'd never done a days hard labor in his life. Karl's hands found her slit, quickly discovering she was already wet, had been so since her told her to remove her underwear again. She moaned when a slim finger penetrated her. Rather than try to work his fingers into her moist cavern while driving, Karl was content to finger her button. Rosilyn wondered how many women Karl had fingered because he knew his way around her cunt better than she did. In five minutes, she was moaning through another powerful orgasm, unconcerned the couple in the back could hear her.

Karl didn't stop at one, or even two. He gave Rosilyn three exquisite orgasms before he pulled his hand away from her now messy pussy. He put his fingers up to her mouth and told her to lick them clean. Rosilyn did. She opened her mouth and licked his fingers. She could smell and taste herself on them. It was nasty and dirty, and she loved doing it.

Rosilyn glanced in the back to see how they'd responded to her orgasms. Marty's eyes were closed and Yolanda was bobbing up and down Marty's prick. Marty had a nice cock and she wondered about Karl's; how big it was, how thick, cut or uncut. She reached for Karl's dick.

"I didn't want you sucking it while I was driving. What makes you think jacking me off is any better?" Karl turned on the SiriusXM radio and tuned it to the newest hits station.

"Sorry," Rosilyn murmurs. The music isn't loud enough to drown out the slurping, sucking noises in the back seat and the low groans Marty makes when he orgasmed in Yolanda's mouth.

They spent much of the rest of the drive kissing in the back seat. Rosilyn knew Marty's hands wandered because she could hear Yolanda moan and saw her squirm on occasion. It made her want to cum again.

"Can't you turn the vibrator thing on again?"

"No, the battery only lasts about three hours. I want it running during the concert. It will be the best concert you'll ever go to. You can masturbate yourself if you're so anxious."

Rosilyn had no doubt that was true. Really, would masturbating be any worse than Karl fingering her for a half hour. Not really. She put her seat back, closed her eyes and touched herself. It felt good and she orgasmed three more times on her own fingers, moaning indelicately through each one.

They pulled onto a beautiful estate a little after six. Karl ordered everyone to stay in the car. He went up to the door and rang the doorbell. Ethel answered the door.

"Who might you be, young man and what do you want?"

"Ethel, it's me, Chloe, and I'm here for the tickets."

"Chloe?" Ethel stared at her for several seconds, "Oh my God, it is you. What a remarkable transformation."

"While I'm dressed like this, I'm Karl. I don't intend to see you while I'm here, but if we do speak, make sure everyone addresses me as Karl. Do I need a key to the guest house?"

"Nonsense. You must come for breakfast. The lock has been keyed to your phone. When you get close, it will unlock. Who's with you? Is Matt and Dianne in the car?"

"No, Marty and Yolanda and a woman named Rosilyn. We're playing a trick on Rosilyn. She's the anti-gay person I told you about when I asked for the tickets and she thinks she's been with a guy for a couple dates. She had a fight in the ladies room with Dianne which is why Matt and Dianne couldn't come with. I suppose we could have breakfast, but it's critical everyone addresses me as Karl and pretends they don't know Marty and Yolanda. Oh, and you can't be a lesbian. Georgina can be a college friend visiting you. No kissing and smooching while we're there. Who should I be in relation to you?"

"You can be my nephew. I'll be your Aunt Ethel. I'll make sure everyone knows to keep the secret. Let me get the tickets, they're in my purse."

"I can't be Bill's son though. He's too easy to look up."

"No problem, Fred's kid."

Ethel left 'Karl' at the door and returned a minute later with an envelope, handing it to him when she returned.

"I still can't believe it's you."

"Listen, I'm pretending to be a rich asshole, so if we have breakfast, just play along if I act like a twit. If this works. It will probably end up being my next play."

Ethel kissed her on the cheek. "Got it. You're Karl, annoying twit nephew, play along with anything you do. Georgina and I can't be a couple. I'll let everyone know and we'll work it out."

Karl hugged his 'aunt', thanked her for the tickets and left with a little wave.

"Who was that?" Rosilyn asked when Karl got back in the car.

"My aunt, Ethel. We're staying in her guest house tonight and she picked up the tickets after I ordered them. One of the servants did, probably, but what the hell."

At the concert venue, they traded in their tickets for passes they wore around their neck, taking their seats in the front.

"Thanks, Karl," Yolanda said, "I would never have gotten to see this concert if you hadn't bought the tickets. I love being friends with a rich guy."

"Ditto," Marty said. "You take good care of us."

"I'd like to thank you too, Karl," Rosilyn said.

"So far, you've done everything I asked," Karl said. "You've earned it. Get ready to cum. I've turned your Lush on to music mode."