Suspicions

Theo’s home was a short drive on quiet streets, so Ashley didn’t pay much notice when he rolled the windows down. She felt the chill of the night air across her body, but it was kind of freeing and naughty. She quickly snuck a pair of her panties under her butt so her juices didn’t get onto his car seat.

Her eyes popped wide when didn’t take the turn towards home that Ashley expected. Instead, he pulled out onto the main road towards a late-night restaurant they’d used to frequent. On the quiet little streets, being naked in the car was a thrill, but Theo’s low sedan offered her no privacy from cars with a higher ride. Sure enough, at the first stoplight a large pickup pulled up on Ashley’s side, and leaning out the driver’s window was one of the players from their school football team. Ashley covered herself automatically as she saw the goon looking down on her. Theo was watching the cross-traffic as the light switched back to green, and didn’t notice until the guy made a disappointed sound and pulled off at the green.

“What are you doing?” He said, glaring at her. “I didn’t tell you to cover up.”

“But, Master. We know him.” Ashley said, and cringed at how lame it sounded as an excuse.

“So?” Theo said, with such an eye-rolling, patronizing tone that Ashley felt even more foolish.

“Well…” Ashley knew it was digging herself deeper, but she couldn’t stop herself. “You were so proud of me back there. I just thought you… wanted me to yourself.” Ashley finally caught that runaway train and switched tracks before it went off the cliff. I almost said because you loved me. What would he have done?!

“I was proud of you back there.” Theo said, putting a harsh amount of emphasis on the past tense. “And I do want you to myself. But I decide the terms of that, not you.”

Ashley nodded quickly. Theo scanned the road, and saw the truck a few car lengths over and in the turn lane, heading into the same fast food place she’d been expecting them to visit.

Oh no.

“Open your bag, pull out your dildo.”

“Theo…?”

“Master.” He snapped. “And even the dildo outranks you, so don’t disrespect the both of us.”

Ashley quickly dove into the backpack and pulled out the dildo. It was still slick with Danielle’s juices, and even with the windows down the smell of sex was permeating the car now. Ashley couldn’t help feeling turned on at that, and her skin flushed all over again, making her shiver from the cool night air coming in the window.

“Recline your seat.” He ordered, and Ashley dropped way back until her head was almost level with the window line. “Spread your legs.”

Ashley did as she was told, feeling the car bump as Theo pulled off the road and into the parking lot of the drive-in restaurant. Ashley used the excuse to poke her head up to see. Thompson’s was a classic burger and fries drive-in restaurant, and had always been a hotspot for kids from Ashley’s school once they could drive there. The restaurant had no seating, you would just pull up and order from one of the waitresses that would walk out to your car. Generally college girls in their sneakers and jeans, with the attitude to match. You could roll down your windows and chat with the people in the next space, or get out and sit on the hood if you wanted to hang out longer. No one bum rushed you out, so it was a good place to hang if you had the time. Ashley could only eat here on her “cheat days” and Theo wasn’t really into the people watching, but it was cool to be out from time to time and see what people were up to. They hadn’t been for a few months, well before Ashley’s enslavement.

The place had apparently changed ownership in that time to Harvey’s, because it was a totally different vibe now. As Theo pulled in, Ashley’s jaw dropped at the state of the place. It was packed, Theo was just able to grab the last space as someone pulled out. And the sassy college waitresses were quite different. Instead of comfortable sneakers and casual clothes, they zipped around between the cars on roller skates, precariously balancing the trays of food as they went. They had short skirts - shorter even than Ashley’s uniform - along with tiny crop tops bearing the restaurant’s name.

Theo parked and set his eyes on one of the waitresses, who was currently bent over away from them, leaning into another car. Her skirt rose all the way up, exposing her brown buttcheeks split by a thong so tiny that her rear had no coverage at all. As Ashley watched, the driver of the car shoved his cash down the front of her bra and shamelessly grabbed a tit as he did so.

“Is this place staffed by slaves?” Ashley asked.

“Some of ‘em, I think.” Theo said, without taking his eyes off the woman. “The others are pretty close to the line.”

“Woah, that’s nuts.” Ashley said.

“We might finally get decent service here.” Theo said. He turned to Ashley. “Start fucking yourself with the dildo. Now. Don’t stop unless I tell you, understand?”

Ashley nodded quickly, not wanting to upset him again. He waited until she had started sliding the dildo into herself, then began beeping his horn to get attention. The girl he was watching popped up and looked over.

Anna.

She skated over quickly and bent in Theo’s open window, looking nervous despite the **** smile on her face.

“Welcome to Harvey’s, How may I - Oh! Ashley!” Anna said as she recognized the pair. “And Master Theo, hello.”

Ashley and Anna locked eyes and both of their cheeks flushed a deep red. Even in light of their recent confrontation that had set their secret power dynamic it was clear that they were both experiencing the vulnerability of slavehood just the same, what wasn’t clear was who was more embarrassed by the situation. Ashley was naked and splayed open in the passenger seat, humping a dildo that - combined with her own wet cunt - was making the car reek of obvious sexual arousal. But Anna was rollerblading around in an outfit that would make a hooker blush, having her tits and ass pawed by every guy with a hungry belly and a few spare bucks. Up close, Ashley could see the grease stains on her chest from where guys who’d been handling the burgers had turned their attention to a different meat.

“Hello Anna, how are you? I heard a rumor you were working here.” Theo said. Anna couldn’t take her eyes off Ashley, and Theo did not seem too put off by that. He casually reached up and began fondling her tits as well, giving Ashley a small side-eye as if daring her to say something about it. Ashely tried to wipe the jealousy off her face, but not quickly enough.

When Anna took too long to respond for his liking, Theo grabbed her nipple through the shirt and pinched until she jumped.

“Sorry, Master Theo. I am doing well, Master Harvey make me work here after class and after I cook him dinner. He says I will work off my punishment here.”

“That’s a smart Master.” Theo said. “He bought this place, right?” Anna nodded.

Duh. Harvey’s. Ashley kicked herself for not making the connection, but to be fair, she was nearly in a sexual fugue state after the poker party and her gruel.

“Can I get you both something to eat?” Anna asked, trying to get out of the car and away from Ashley’s unwilling sex show and Theo’s molesting hands.

“Yes. I’ll take a cheeseburger meal with a large Coke.” Theo stopped, “Actually, I’m feeling kinda flush tonight, I just won a good bit of money off my poker skills and Ash’s cocksucking skills. Make it a double cheeseburger meal. When Anna’s eyes flitted back to Ashley he continued with a clear note of annoyance. “She won’t be having anything, she is on a special diet.”

Ashley, too busy fucking herself with the dildo, didn’t notice Anna’s eyes go slightly wide when Theo mentioned that. But Theo did notice, and filed it away for later.

“Si, señor,” Anna said, popping up from the car and away from Theo’s grip, then skating off towards the central kitchen to put in the order. Theo looked mildly disappointed when Anna left, but not for long.

“Almost as good as your bottle service back there.” Theo said, without looking at Ashley. She wasn’t sure if she should acknowledge the compliment or if he was making a back-handed insult, so she said nothing. Theo didn’t seem to expect an answer anyway.

Ashley panted desperately as she continued to slide Theo’s massive stand-in into her body, and cooed with pleasure as it drove her wild. She was sweating from the exertion despite her level of fitness, the night was one long sex fest and it was keeping her heart rate up like a long cardio session. She must have looked conflicted, because Theo looked over and asked:

“Is there something you wanted to say, ****?”

“No, Master…” Ashley said, but he didn’t seem satisfied by her answer that time. He glared until she felt like she was withering under a brutal interrogation - even though he said nothing. “Ok… I… just… when you said you were going to be with Danielle and Madison and the others… Did you mean it?”

Theo’s expression remained stony.

“No. What I said, quite clearly, was that you and I were going to fuck them. Not ‘be with’ them or whatever girl euphemism you want to use. But with permission next time.”

“But…” Ashley could tell how pathetic she was sounding, so she stopped herself short. But Theo knew what she was going to say regardless.

“But what? Why did I just paw Anna’s tit?” Theo said. “Because I have permission. Your teacher gave me the phone numbers of the other Masters, and Harvey seems more than willing to offer up Anna when she’s in trouble.”

“What does that mean?”

“What are you learning in that class I pay for anyway?” Theo looked disgusted with Ashley, and shame hit her like a punch in the face. I hate disappointing him like this. But I also hate him showing all these other girls attention… “Fine, if Stonebridge won’t do it...”

Theo honked the horn again, and Anna came hurrying back over, nearly crashing off the curb in her hurry to respond.

“Anna.” Theo got right down to it. “Harvey told me about your punishment.”

“Sir?” Anna said, looking more nervous by the second.

“He said that the other Masters in your class could use you as they saw fit, until he said otherwise, right?”

Anna nodded, now wide-eyed. She looked as though she was ready to bolt like a spooked deer.

“Well, the Senator and Peter are busy, and I don’t know what Dexter’s deal is, so that leaves me.” Theo pointed to the hood, “Bend over.”

“Master?” Ashley asked, hoping he wasn’t about to do exactly what it looked like.

Anna obeyed him, rolling around to the front of the car and bending over until her elbows were on the hood and her tits were hanging free, only a few feet from Ashley. She looked scared but also resigned. Ashley noticed that some of the others at the drive in were paying attention now. Between the honking and the girl with her ass up on his hood, all eyes were on Theo now.

But his eyes were on Ashley, and deadly serious.

“I’ll keep teaching this lesson as many times as it takes, ****.” Theo dug in his nails with the final word. “Don’t you dare cum without permission.” He popped open his door and climbed out. Ashley’s heart was pounding hard now, her face flushed with humiliation but also, she admitted, some jealous anger as he casually took up a position behind her **** sister. Anna grunted as he yanked down her flimsy panties and pushed up her skirt.

One of the other waitresses actually gasped as he pulled his massive hog out of his jeans, but Theo didn’t notice or care. Anna tried to put her face down in her hands to hide her reaction as he split her, but Theo would not allow that. He took a fistful of her hair and pulled her back up, using it as leverage to ram his cock deeper and deeper with each thrust. She fell forward onto the windshield, and her tits dragged up and down the glass. The place went nearly silent, leaving only Anna’s grunts and the sounds of traffic echoing through the night as he slid himself up inside the poor girl. Ashley had seen “Mr. Harvey” on her desk, Theo was much, much bigger - maybe the biggest she’d ever had.

Ashley couldn’t help thinking of a primal animal display on some nature documentary as Theo fucked Anna hard on the hood of his car. A few of the women covered their eyes and looked away, but all the other men stood and watching him. In admiration. Ashley thought. She was still jealous, that wasn’t possible to tamp down entirely, but she was also proud. Proud of her Master and proud of herself for being his ****. Anna would have to go home and satisfy herself with Mr. Harvey, but Ashley got to be taken home by Theo.

Theo began grunting himself as he reached his release. She’d blown him only a short time ago, but Ashley beamed at how quickly he was able to fuck again. It was harder not to cum herself just watching him. He started inside Anna, but pulled free and finished his last few shots across her asscheeks as if marking her. She nearly collapsed onto the hood, and another waitress coming over with his food helped Anna to her feet. Theo casually grabbed a napkin off the tray and cleaned himself, then ordered his food to go.

Theo flopped down in the driver’s seat and turned over the engine. Ashley was still edging like a maniac, ordered not to stop but also ordered not to finish. Theo looked marginally more pleased with the situation.

He made her continue as he pulled out and drove them home, slurping loudly on his drink.

“You want to cum?” He asked.

“Yes…. Yes please, Master.” Ashley slurred.

“So what was tonight’s lesson?”

“It was about permission, Master.” Ashley panted. “Masters give it… Slaves need it…”

“Exactly right.” Theo said. “Now I give you permission to finish.”

Just hearing the words was enough to give Ashley an orgasm powerful enough that she worried he’d lose control of the car. She thrashed in her seat over and over, and when she finally came to, she realized they were sitting in Theo’s driveway. The family security camera was pointing right into the windshield and would have caught the entire thing as he pulled in.

“Good girl, Ash.” Theo said, and she beamed a little hearing her name instead of ****. But he kept going. “Now that we’re on the same page, I want you to find out more about Madison and Dex.”

“Master.” She said, not as a question, but apparently it came off as such so he kept going.

“I get a weird vibe off that guy, don’t you?” Theo said. Ashley wasn’t in the headspace to lie, so she just nodded. “Well, she doesn’t have a body like yours, Ash, but she’s still a prime piece of ass. Figure out what’s going on there so I can fuck her. Understand?”

“Yes Master.” She said, successfully hiding her cringe at his description. He wants me to bring him another girl? I can still smell Anna on him and he’s already thinking about the next one.

“Perfect.” He said, leaning over and giving Ash a kiss on the cheek. “Let’s go inside.”