Memoir of a Young Mistress Pt. 20

It was the first day of Spring, and Emily was excited. Her parents had told her that since she was enrolling in the local college soon, she would need a car. They had promised to help her look on the first day of spring. Several phone calls and test drives later, Emily was ecstatic to be backing out of her parents' driveway, alone, in her very own car.

Nothing fancy, almost ten years old, but it was all hers, and she could do anything she wanted to make it "hers". She went to the auto parts store to get floor mats and seat covers. The car had minor cosmetic damage appropriate for a decade-old car, but nothing terribly unsightly. The one thing that bothered Emily the most was the black painted rims, as the car had long ago lost all four of its factory wheel covers. Those would have to wait, along with upgrading the radio.

Next, Emily drove to one of her favorite shops, and tried on several outfits, taking a minute to tease Ted with a couple of photos shot in the changing room. Since last fall Ted had amassed almost a hundred pictures of Emily, most sent from her phone, and almost all of them nude or semi nude.

After he responded to her first picture message with a "Hot!" comment, Emily asked if Ted was free, and he said that he was. She offered to pick him up in her "new" car and he agreed.

Familiarity and repetition causes one to fail to see the need for discretion. This was evidenced by Ted allowing Emily to drive directly to his house, where he walked out and got in Emily's car, not caring who saw. There was a time not too long ago where such a pickup would have involved walking several blocks, and darkness.

Now, oblivious to Ted and Emily, neighbors were noticing his comings and goings. People were starting to gossip about "the man that keeps going to Emily's house".

As they drove, Emily happily pointed out all the features of her new toy, and Ted noted the minor flaws. He told her to drive to the custom shop where she had bought the mats and seat covers.

Ted and his wife had separate charge accounts, the excuse being they could use them to buy gifts at Christmas and not spoil any surprises. The bonus to Ted was he could use the card to verify his age to access premium content on porn sites, but now that he had Emily, that need was obsolete. He now used the card to buy gifts for Emily, which he had already done on several occasions. A dress here, some makeup there, and a few dinner dates on the outskirts of town.

Now he used the card to purchase a new set of wheel covers for Emily's car. As they watched the tech install them, Emily hugged Ted and thanked him. He smiled.

After a lunch, Ted saw a small shopping center and told Emily to pull in the lot. He had noticed one of the shops sold school uniforms.

"Let's go look around," he said. "I have an idea."

The shop had racks of the usual polo shirts in beige, white, burgundy, blue, and pretty much any other school color, along with co-ordinating slacks and skirts. There were jackets and sweaters, and shoes and caps.

Ted found the garment he had pictured, and directed Emily to the rack. It was full of pleated skirts, like the stereotype "Catholic school" uniform used. There were solid black, navy, and the near-famous plaid.

Ted pointed at the rack. "Find one that looks good."

"Haha, really? Okay," and she browsed the rack for her size. She took a couple of the skirts into a changing booth. While she tried them on, Ted found several shirts to complete the outfit and went to her booth and passed them under the door. "Try these too," he added.

She came out in her favorite, a combination of plaid pleated skirt and white oxford uniform shirt. The skirt was too short to be "school-appropriate" but that was perfect for what Ted wanted. He got a pair of white knee-high socks and handed them to her.

"Put these on too, and take off all the price tags. You're wearing this out of the store."

Emily went back to the booth and did as she was told.

The cashier gave a sideways look at Ted as she rang up the sale. At first she thought it odd a father would buy such a poorly-fitting uniform for his daughter, then she concluded this wasn't a father and daughter, and she disapproved even more.

Ted told Emily to drive to the park where he first met with her last Fall. They had returned to the park a few times for lunch dates, and would sometimes sneak off into the trails for clandestine fun. Ted was in the mood for some dirty, kinky fun right now.

"So," he said as he led her by the hand down one of the trails. "Let's talk about your daddy incest fetish more."

By the time they got to a clearing in the path, Ted had created a scenario that he wanted to role play with Emily, and Emily was eager to play the game. It combined her incest kink with being told what to do by Ted, and to make it even more exciting, they were out in a public place. A jogger or hiker could come upon them at any time.

The clearing was a large circular area, with tables and attached benches. There was an overflowing trash can from all the lunches that had been consumed there, as well as late-night beer-and weed parties. There was no full-time caretaker at the park, and the county only sent someone to clean up about once a week.

"Here's the deal," he told Emily. "You come here once in a while after school, and this is your favorite spot because it's secluded. You do your homework and study, but a couple of times you started daydreaming and got horny, so you laid down on the table and played with yourself. It was so exciting to you that now you come here just to masturbate. You fantasize about someone seeing you, and what might happen."

"Ooohhh... me likey..." she said. She laid down on the table.

"Your dad comes here too, but you don't know that. He sits here and reads. He's going to catch you. He's going to be very angry. Are you ready for that?"

"Yeah..." she answered softly.

Ted and Emily hadn't role played much, and Ted knew he would need to establish a "safe word" for Emily, but didn't want to explain the concept right now. He was already getting aroused thinking about what he was about to do.

"If you get uncomfortable with anything we're doing, say 'chicken' and I'll know you want to stop, okay? That way you can play along and say things like, 'no' or 'please stop' and it can be part of the role play. But 'chicken" means you seriously want to stop."

"Okay."

"I'm going to circle around, I'll be back, but I'm not saying when." He kissed her goodbye, and headed off down a different path.

Emily thought a moment. She wanted to get into her role, as opposed to just playing a game. She had fantasized many times when she masturbated, and this was just an extension of that, but with another person, like a play. But she hadn't fully immersed herself into a part yet. She wanted to do that now. She imagined herself more naïve and innocent. She decided she was a virgin, and had never done much with a boy, actually quite similar to her real self a few months ago.

She pulled the white panties off and stuffed them into her purse, and closed her eyes, relaxing. The sun illuminated the clearing and warmed her face. She began to gently explore the folds of her labia with her fingers.

Ted did a short reconnoiter around the park. There had only been two other cars when they arrived, and he knew one had brought a mother with small children, currently at the playground. The other, he had no clue. As he circled around, he saw a new car was there now, in addition to Emily's compact. So, there was definitely a chance they might be caught. He wondered how fast they could flee if that happened.

Emily had a finger inside now, and her wetness allowed her finger to easily slide in and out. She tried not to peek, or to think about her "father" coming to find her. Instead she sank into the role of Naïve Emily, masturbating in a public place, fantasizing about someone catching her. She unbuttoned her shirt and slid her other hand down the front of her bra, and played with a nipple.

Ted liked the idea of role play, but by his own admission wasn't good at it. He preferred to play his part only to help Emily experience hers. So he made no efforts to get into a character. There was no father going to his favorite spot, who was going to find his daughter masturbating. He was just Ted, but he was going to enjoy what he was about to do.

As he approached the clearing, he slowed, and checked the ground for twigs and other objects he might step on, revealing his approach. It was impossible to avoid everything, but at least he didn't want to barrel in like a rhinoceros.

He got close enough to see Emily in the distance. She was definitely laying on the table, knees up, legs spread. It appeared she had unbuttoned her shirt as well. Good girl.

Ted has chosen a different way back, and he was approaching her from a direction that would conceal his approach for the longest possible time. The disadvantage to this was he couldn't really see what she was doing that well. She was obviously masturbating, but there wasn't much to see from this angle. He instead enjoyed her breasts, as she had completely unbuttoned the shirt now, and had pulled her bra up, exposing them to the sunlight.

Emily loved the feeling of the sun on her breasts. Ever since she had stripped in her backyard, she knew she loved being nude outdoors. She didn't know it at the time, but her neighbors on either side had loved it too. Her thoughts drifted back to that day, and she was distracted enough to not notice the sound of someone creeping up to the table on which she lay.

Ted did all he could to conceal his approach, and was sure that by now, Emily had heard him, and was just playing her part by acting oblivious of his presence. He crept to within three feet of the table, standing directly behind her head. Her eyes were closed and she had her skirt pulled up to a very immodest height, both hands between her legs.

Ted savored the view of her lovely breasts, swaying slightly from the movement of her arms and hands as she pleasured herself.

The sight aroused Ted magnificently, and he felt his erection growing, yearning to be free of its restraints. Ted quietly unzipped and freed his shaft, giving it a few strokes as he crept closer. When he was right behind her, he leaned down, got close to her face, and pressed one arm against her torso, holding her down. The other hand clamped tightly over her mouth.

Emily was genuinely startled and tried to shriek, but Ted's hand was so tight over her lips that all she could get out was a muffled "meep". Her eyes shot open and all she could see was the sky, the canopy of trees, and a bit of shoulder. For a moment she panicked, not sure it was Ted or a stranger. She calmed slightly when he whispered in her ear.

"You little whore. I had no idea. All those days you came home late and said you were doing homework...and you were out here, showing your body off for the homeless guys in the woods? Do you WANT to get raped? This is how it happens! Or maybe you're such a cheap whore you just fucked the first guy that saw you?"

Emily tried to shake her head to say "no" but he held her tight.

"Yeah, I bet that's how it went down. You were just sooo horny, weren't you? You wanted it so bad you didn't care who you got it from. You just fucked the first guy that came by. You little slut. Teasing me all the time with those short skirts and those skimpy tops. Do you think you can just keep doing that? You can't just keep teasing a man and expect him to ignore it! No, you can't. Sooner or later, you have to pay out."

Emily was breathing hard through her nose, both afraid and impressed at the way Ted was acting. He was really getting into it, she thought.

"It's time to pay, honey. Daddy is tired of your teasing."

Ted backed away enough that Emily could see his face. He was still over her, so he was upside-down. He kept his hand tightly over her mouth, and with the other, began to grope her breasts.

"Is this what you want? You want some guy to feel you up? Run his hands all over you? You want to see what it's like to be touched all over, huh? Okay, I'll touch you. You need to get a taste of what happens when you tease men all the time."

Ted was handling Emily's breasts so roughly she tried to pull his hands away, but he was much stronger. "And what do we have down here? Did you get yourself ready for me? Do you want a man's finger now? Do you?" He shook her forcefully for emphasis as he asked her. She shook her head and he made out, "No," under his fingers.

"Yes, you do. I know you do," he insisted, and he slid his free hand between her legs, probing with his fingers. She breathed in hard through her nose and her eyes opened wider.

Ted sank two fingers deep into Emily's wet pussy, as far as he could, and held them there a moment, then began finger-fucking her. She grabbed at his wrist weakly, unable to stop him. Her other arm attempted to cover her bare breasts.

"Yeah, just like that...you like that don't you? That feels really good, huh?"

Emily weakly shook her head "no" but didn't struggle more. Ted saw that childlike, withdrawn expression again, like she was being scolded.

It was time, Ted decided to teach her more about submission.

"I need to cum now, and you're gonna help daddy. If you help daddy cum, when I'm done, I'll forget I saw you here, and there won't be any more punishment, as long as you promise to stop coming here. Do you understand?"

Emily nodded yes and he heard "Mhmn," through his fingers.

He released his grip on her mouth and withdrew his fingers from between her legs.

"Daddy, I'm sorry, please..." she tried to explain, but he interrupted.

"Quiet!" She shrank back again. "You have to be punished some way, this will be appropriate. Scoot back, towards me."

"What are you doing?" she whispered.

"Teaching you a lesson," he answered. She slid back towards him, and he took her by the arms and pulled her closer to the edge of the table, so her head was hanging off the edge. He aligned himself so his cock was in her face. "Swallow my cum."

Emily took Ted into her mouth, allowing him to push as far as he wanted. He returned his hands to her breasts and kneaded them as he fucked her mouth slowly. She lowered her hands and hesitantly reached for her pussy again, and he allowed it.

Jason took a power walk through a different park every day, in a weekly rotation. This park was his favorite as it had the cleanest paths, and lots of trees. He plugged in his earbuds and set his mp3 player to a setlist of fast songs to help him keep a good pace.

This park had plenty of paths through the woods, and he had a routine he followed each time he was here. First a loop through the path by the swings, then once around the lake, then the one that ended up by the tennis courts. It made for a good workout.

The first path had some tables and benches in a clearing and he used that spot to stretch before he walked. As he made his way there, he saw there were a couple of people on one of the tables. At first he thought one was helping the other stretch.

Emily didn't know if Ted was still roleplaying or just enjoying fucking her mouth, but at this point it didn't matter to her either. She was turned on by being taken this way, and by Ted's fondling of her breasts, and the fact that she was playing with herself, and all this was happening in a public place.

Neither she nor Ted saw Jason as he approached the edge of the clearing. Ted was focused on watching his cock slide down Emily's throat, and Emily had her eyes closed again, enjoying all the sensations of the experience.

Jason froze at the edge of the clearing. He pulled his earbuds out and listened to the pair moaning as they coupled. His view was from the side, but he could clearly see what was going on, and it was better than any porn video he'd ever watched. This older guy was mouth-fucking this hot girl while she fingered herself! He watched the show, hoping he could be still long enough to see it reach its conclusion.

"You like daddy's cock, don't you? Yeah...you do. That's a good girl, honey. Make daddy cum..." Ted was saying the words mainly for her benefit, but it did help him a bit too, playing the part of the frustrated father.

He was pleased at how good she had gotten at taking all of him without gagging, and this position, with her head off the table's edge, helped even more. He could see the bulge of his cock expanding her throat each time he slid in. He glanced down at her hands, now rubbing quickly. She was probably getting close to orgasm herself. He slowed, hoping he could hold back long enough to cum with her.

Jason was amazed at this scene. He could have sworn he heard the guy say he was her dad? That would just be too weird and hot all at the same time. He had read stories about incest, and seen a few bad videos with obvious actors, but this looked pretty real. Or maybe they were just role playing? Either way, it was hot.

Emily straightened her legs, and her toes pointed down, and Ted knew it was happening, so he sped up a bit, and made his thrusts deeper. Just as she was finishing, he grunted and unloaded his balls into Emily's throat, keeping his cock deep in her until he was spent. Pulling out, he leaned down and kissed her forehead, cradling her head for support.

"Good girl, honey, you made daddy cum. Daddy loves you so much."

"I love you too daddy," she smiled.

Jason knew he had to do something, either advance or retreat. He plugged his earbuds back in and started walking, as if he had just came upon the pair. He casually looked in their direction, hesitated as if he were surprised, but kept moving, and went on by, looking back once but not stopping.

Emily crossed her legs and covered her breasts with her arms, and Ted ducked down so that his now-relaxing cock wasn't visible, but they both knew they were in a compromising position. Ted's emotions were a combination of exhilaration and "Fuck, what have I done?" Emily was just trying to cover her nakedness. Both were relieved that the man kept going, apparently just as eager to get on with his day as they were with theirs.

Once he had passed, Ted and Emily both broke out into the kind of nervous, relieved laughter that people succumb to after a near-fatal accident. Adrenaline flowed, and they took in the rush that had come with getting caught, and being seen. Ted recovered first.

"Shit, he saw us! He didn't say anything, but I know he saw us! Damn!" he exclaimed.

"Did he actually see what we were doing?" she hadn't been able to look up as fast as Ted.

"I'm pretty sure he did. He came out of nowhere, I didn't see him until he was in the clearing," he confirmed.

"Oh God, he saw us...oh, God, haha!"

Ted was already tucking his shaft back away and Emily was fixing her bra as they spoke. Emily sat up and buttoned her shirt. "We'd better leave, he might come back," she cautioned. "Yeah, no point asking for trouble," Ted agreed.

Emily hopped off the table, not bothering to put the panties back on. She and Ted went straight to her car and got out as fast as they could without trying to look like they were fleeing the scene. Once away, they were again nervously laughing, and enjoying the rush from getting caught. Ted wondered if the guy got turned on watching them, and again thought about the website and its live video feature. He decided this would have to be something they would do soon.

Jason broke his routine and circled around for a second lap through the last path, but the pair had fled. He went to the table, and saw the wet place at the end where the girl had been playing with herself. He traced his fingertip through the dark spot on the wood and smiled.

End of part twenty.