Memoir of a Young Mistress Pt. 15

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A date with Sierra and Emily results in backseat blowjobs.
2.6k words
4.64
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Part 15 of the 29 part series

Updated 06/07/2023
Created 12/17/2015
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Emily laughed out loud, and Sierra assumed it was because of her right-to-the-point question, but Ted and Emily exchanged a quick glance because they knew otherwise.

"Oh gosh, don't tease me girl. It's been years. So long I don't remember what it was like."

"Emily, get in the front and keep a watch out for anyone walking by the car. Ted, back seat." Sierra pushed Ted towards her car.

"Are you serious?" Ted was having a great time, but certainly did NOT expect this.

"Totally, get in," and she pushed him again.

Ted looked at Emily, and he could see in her face a combination of jealousy and disappointment. Ted did his best to convey a look of, "The ends justify the means," and she reluctantly agreed.

They got in the car, and Sierra wasted no time, unzipping Ted's pants and pulling out his cock. Emily couldn't bring herself to turn around and look, but she stole peeks in the mirror at Ted's face while she kept a watch for anyone walking too close to the car.

Ted had overheard Sierra talking to a couple of the boys in the youth group in the parking lot once. She was saying, "Honey, if I give you a blow job, you will never have a better one, so you might want to wait or the rest of your life will be really disappointing."

Ted thought to himself, "Time to find out if she's all talk or not."

Sierra didn't hesitate; two licks around the tip to make it slick, and she was right at it. Ted was only slightly hard, but her sucking and tongue work had him fully erect in less than a minute. Once there, Sierra held a firm grip at his base and repeatedly pushed herself all the way down onto Ted's shaft, and Ted could feel the tip of his cock going into the back of her throat. She had a pattern, one time long and slow, until she had all of him in, then she held it there a second, then slowly back up, followed by several quick thrusts, but every time going as far down as she could. Ted had never experienced head like this, and he knew he wouldn't last long. He couldn't help but moan out loud.

Emily couldn't handle it. Ted was HER man. She was the one who could please him, that was her place. She started the car abruptly and said, "Cop! Stay down, stay down! Don't come up they'll see you!" She pulled out of the lot, driving away from the nonexistent police. Ted had immediately panicked and pulled away from Sierra, tucking his stiff cock back into his pants as best as he could, and Sierra looked upset that he wasn't willing to keep going. Emily drove to a better-lit area a couple of blocks down the road, and stopped the engine.

"Maybe we'd better get home," said Ted. "I told my wife I wouldn't be too late," he admitted.

"Oh, come on, at least let me finish you off," teased Sierra. "I know you were close."

"Yes, I was, but there's no way I could explain to my wife, either of your parents, or the church leaders why I got caught by a cop at the beach with you two, getting a blow job."

"Yeaahhh..." admitted Sierra. She got out and swapped seats with Emily, who was looking at Ted with a triumphant smile on her face.

Once the car was in motion, Ted and Emily both were surprised and pleased when Sierra suggested, "You should try to finish him off before we take him home. I'll take the back roads and go slow."

Emily acted innocently enough. "I, um...I've never done a BJ before."

Ted did his best to sound sincere in his lie. "It's okay, you don't have to, I've had way more fun than I expected, really..."

"Go on, girl, just do it," Sierra laughed. "It's easy. Just don't bite him."

"Okay..." she said, with feigned hesitancy, and leaned down to unzip Ted's pants.

Sierra did as promised and drove slowly, taking as many dark side streets as she could find, even circling around at one point. Ted enjoyed Emily's blow job and Emily did her best to deep throat him, but it was difficult in the car at this angle. Ted admitted silently to himself that Sierra was much better, but he knew that was from plenty of practice. In time, he planned to turn his young mistress into the best provider of fellatio that ever lived.

Ted watched Emily's head bobbing up and down on his cock with pleasure. A couple of times, he glanced up at the rearview mirror, where he saw Sierra's mischievous eyes looking back at him. He gave her a wink and she winked back. Ted wondered if the wink was just because she had started all of this and was satisfied with herself, or if she was flirting with him too.

Ted had kept his eyes open so he could watch for other cars that got too close, but there were none on the deserted back roads. He succumbed to the sensations and closed his eyes, letting some fantasy creep into his thoughts. The girl that was fellating him drifted back and forth between Emily and Sierra, and he fantasized about a three-way. With that image, it didn't take long to finish, and soon he unloaded in Emily's mouth with a slightly-suppressed groan.

Sierra still caught it, and cheered Emily on. "Swallow, you got to swallow it!"

Emily had already planned on swallowing, but a part of her enjoyed this combination of exhibitionism and being told what to do, and she hungrily swallowed all of Ted's load without hesitation.

Ted and Emily both made a show of how much fun this first-time experience was, and Sierra gleefully asked both of them questions about it, relishing the fact that it had been she who started the whole thing. Once Ted was cleaned up and properly stowed, Emily and he shared a couple more kisses and then Emily leaned on his shoulder and closed her eyes the rest of the way to her house. Soon she was nodding off. Ted played with her hair and thought to himself that he might like her hair to be longer. He made a mental note to tell her so and see how quickly she complied.

Sierra saw that Emily looked sleepy so she didn't talk more, but she often looked in the mirror at Ted and about half the time caught him looking back. Ted knew that look; Sierra was already cooking up more risky plans.

When they were a couple of blocks from Emily's house, Sierra pulled over so Ted could get out. The plan was that he'd be picked up again after Emily was dropped off, and that way, there was no risk of Emily's parents seeing him in the car.

Emily had fallen completely asleep, and Ted gently slid out from under her and let her lay down in the backseat. He kissed her cheek and got out, walking around to Sierra's side. "This was an amazing night. Make sure she knows that too. You guys are now my official new best friends."

"Be right back," said Sierra, with a smile.

It was about ten minutes, and Ted got a text from Emily just before Sierra returned.

Emily: I'm sorry I fell asleep. Why didn't you wake me up? (sad face)

Ted; You looked exhausted, Angel. I'll see you soon enough. (wink) (heart)

Emily: I love you (smile)

Ted: I love you baby. Hey, I have a question...

Emily: Yes?

Ted: I bet you'd be even more stunning if you grew your hair out. Would you try that sometime?

Emily: Sure. (smile)

Ted: She's here, go to sleep baby.

Emily: Ok (smile) g'night.

Ted walked towards the rear door but Sierra waved him around. He saw that she had tossed her books and purse into the back seat. He opened the front door and slid in.

"So?" she asked with a big grin.

"So? Um...thanks?" he laughed.

"You're very welcome," Sierra was very satisfied with herself. Ted thought she probably just added him (and Emily) to a long list of people that she had corrupted.

"Admit it. You've never had so much fun in your entire life," she was quite sure of herself.

Ted admitted, "It was definitely in my top ten. Maybe top five."

As she drove Ted home, Sierra's conversation focused on the new CD she had playing, and how much she loved that band. When they were a few blocks away from the convenience store, Ted suggested she just go down a dark side street so that he could get out with less spectators and walk quietly home. She pulled onto a road in a part of Ted's subdivision where no houses had been built yet and stopped.

Ted looked over at Sierra. "Shut the car off for a minute, if you don't mind. I want to ask you something." She complied.

He leaned closer to Sierra and rested his arm on the seat behind her shoulder. His fingers slightly brushed on her long hair, and she felt it, and she shivered. Ted noticed the reaction. Sierra turned to face Ted as he spoke.

"All the talk, the Suicide Girl stuff, teasing guys at church, the pictures you sent me...why do you do it?"

"What do you mean?" Sierra was caught off guard by the question.

"We've shared a lot of secrets recently. You know me pretty well, but I can't quite get a read on you yet. What drives you? What...well, what tuns you on? I'm getting a fetish vibe off of you, and honestly, it's something I've been reading about. Is that something you want in your future?" Ted wasn't sure of the reaction he'd get with his question, but he was confident enough that by now he could ask Sierra anything and not get in trouble. After all, his cock had been in her mouth less than an hour ago.

"I am interested in fetish stuff, yeah. Mostly dom/sub stuff," she admitted.

"And you're a sub," Ted was guessing, but he was pretty sure he was right. Although she was outgoing and blunt, her poses in the pictures and behavior in the back seat were more that of a girl that wanted someone else to take charge of things.

"Yes...but..." she hesitated. Ted continued with his analysis. "You're a sub, you want a dominant guy, but you haven't found one yet. Every guy you date is intimidated by you and you always end up being in charge. That's why you never date a guy more than once or twice, right? Not what you want. Not what you need."

Sierra felt vulnerable at being figured out so accurately. "Yes."

Ted leaned closer, playing with Sierra's hair. "You're not going to find a guy like that in youth group, honey. Boys aren't mature enough to be into anything like that yet. They're nervous as hell and thrilled that you even talk to them. The kind of guy you want is outside your circle, unless you make that orbit bigger." He saw he was pursuing the right track and made his conclusion. "You don't need a boy. You need a man."

Sierra looked into Ted's eyes. The lights from outside the car barely illuminated their faces, but she could clearly see his eyes, and she had never seen him look that way. It frightened her and turned her on at the same time. She saw animal lust.

Ted was letting his demons lead the way as he went on. His voice was deep and it was hypnotic to Sierra. "Tell me your fantasies, Sierra. What would your master do to you?

Sierra felt commanded to reveal her thoughts, as if Ted had her under a spell.

"I want to be treated like a slave. Like property. Like an object. I want to be handled rough," she confessed.

Ted wrapped his fingers deeper into Sierra's long, dark hair. Impulsively, he grabbed it tightly in his fist and yanked Sierra's head back. Sierra gasped.

"Like that. That's what you want," he said in a low voice. His tone wasn't angry, but it was menacing.

"Yes," Sierra whispered. She started to shake. She didn't know if she was afraid or aroused, or both. Ted didn't release the tight grip he had on her hair. He gripped more of it, and pulled harder, making her cry out. "Yes, SIR," he corrected.

"Yes, Sir." she immediately answered.

Ted forced her to face him by pulling her hair again. She was looking down, and Ted saw the submission in her body language. "Look at me! Eye contact." She looked up at him, and her eyes glistened. Ted felt powerful, and extremely aroused.

"You're turned on, aren't you?" he asked. She nodded as much as her limited range of head motion would allow.

Ted reached over with his other hand. Sierra had worn a lightweight top for the weather, but at the beach she put on a hoodie for warmth. The hoodie was now in the backseat.

The top was a two-piece layered camisole. The outer layer was sheer dark green lace with spaghetti straps and the top under it was a lighter green, strapless, and made of cotton. Sierra was not a fan of undergarments, to the point of bragging about it openly at church. Ted wondered if she was wearing panties, because he could clearly see through the fabric of her shirt that she wasn't wearing a bra.

He used his free hand to lower the closer of the straps off her shoulder, then traced his fingertip along the skin just above the edge of the strapless shirt. As his finger made the return trip back, it hooked into the edge of the top, and pulled it down, exposing one pale, petite breast in the dim light.

Ted appraised the breast and nodded. "Nice," he whispered.

"Thank you, Sir," she whispered back.

Ted leaned closer. Sierra felt Ted's breath on her bare breast. His mouth hovered over her erect nipple, just a couple of inches away. He slowly scanned her breast, then up her neck, and leaned in closer, but never made contact with her skin. He was enjoying teasing her. He still held her hair tightly in the balled fist of his other hand. He whispered into her ear.

"You like this, don't you?"

"Yes, Sir, very much."

"This is why you need a man. No boy will ever do this for you. Set your sights higher. I promise you, many men want a girl like you. You'll find your master soon enough if you keep your eyes open."

"Yes, Sir."

Ted backed away and released Sierra's hair. He pulled her top back up slowly, making a point of brushing the back of his fingers against her nipple as he did. As he replaced the spaghetti strap, his tone and demeanor abruptly changed back to "Mister Ted" that Sierra usually saw.

"Thanks for a great time, Sierra. Maybe we can do this again soon," he said cheerfully, reaching for the door handle.

Sierra was still shaken and aroused. "Thank you, Sir-Mister Ted," she stammered. "I mean, you're welcome."

Ted was already out of the car and was closing the door.

Sierra started her car, drove home, and went straight to her room. She stripped and put on a robe, and took one of her dildos from her dresser drawer. She went to her bathroom, got in the shower, and masturbated herself to orgasm.

Ted walked home, took a shower, admired himself in the mirror, and went to bed.

The succubus and the demon each laughed to themselves, and continued their dance.

End of part fifteen.

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