Memoir of a Young Mistress Pt. 04

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Emily sends Ted a risqué picture.
2.1k words
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Part 4 of the 29 part series

Updated 06/07/2023
Created 12/17/2015
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About ten minutes ago, Emily did something very out of character for someone so introverted. She'd never figure out what gave her the courage, but she'd sent Ted a text.

He replied almost immediately, and they began talking comfortably, as if they'd been friends for years.

More than friends, actually. The conversation had quickly gone down a path she never thought she'd discuss so freely with an adult in a text conversation. Not to say she wasn't enjoying it immensely; she found herself aroused and even told him about it.

Covered by sheets and a blanket, Emily had drawn her legs up and had one hand under the covers, gently tracing the line that had grown damp on the outside of her green cotton boyshorts. She'd thought about Ted plenty of times while she fantasized, as well as several other older men. Some she knew in real life, others were favorite actors or singers, but all had that in common; they were old enough to be her father.

When she confessed her "older man fantasy" to her best friend, Sierra's first comment was, "That's hot," but then it turned to friendly teasing about Emily having a "daddy fetish". Sierra was very much into fetishes and the kink lifestyle. She had a secret collection in her bedroom of toys and clothes that might make even her mother blush, if she were ever to find them.

Emily had never specifically named Mister Ted, but Sierra knew she had a thing for him, much more than any of the other girls. She saw the way Emily watched him when he came into the church auditorium, never taking her eyes off him.

As Emily texted with her free hand, she shifted in bed, causing the fabric of her loose-fitting tee shirt to slide across her breasts and tease her nipples slightly. They grew in response, and formed small peaks in the fabric of her shirt. She continued to shift her shoulders back and forth, seeing the effect the teasing had on her nipples, and increased the stroking on the outside of her boyshorts. She wondered if she could get away with going out without a bra one day, if the shirt was the right kind of fabric. She practiced the move more, noting how quickly her nipples reacted, and wondered about the reaction she might get if she could pull off the move in the presence of a man. Would he stare? Leer? Maybe make a comment? The thought of a man openly making a sexual comment made her even wetter.

She had already told him she was wet, in response to his revelation that he was fantasizing about her, and although not directly saying it, she was pretty sure he was masturbating that very moment. "We're playing with ourselves and we're texting each other about it," she thought gleefully. Her friends shared stories about the fun times they had teasing boys and being teased back in return. Some even shared pictures, if their phones had a camera.

She considered it.

Emily>Hey can I send you a picture? (smile)

Ted>Ummmm of what? (blush)

Emily>Can't tell you hehe I have to show you (wink)

Ted>Oh my goodness if you do that

Ted>If it's anything like what I'm imagining I would be your best friend forever haha (big grin)

Emily>OK just a sec

Emily pulled the covers back and tried snapping a picture. On the third try she got one that satisfied her; a close-up shot of her hand down the front of her boyshorts. Nothing really could be seen, nothing "bad", she thought. But it was obvious what was going on in the image. She sent the picture to Ted's phone and waited.

About a minute later, she got a reply.

Ted>Oh. My. God.

Ted>That...

Ted>That is the most amazing picture I've ever seen

Ted>THANK YOU (big grin)

Emily>Hehe you're welcome (smile)

Ted>Oh Lord I wish I could call you...

Emily>Yeah? You can if you wanna I'm alone (smile)

Emily>I mean my mom is home but she's nowhere near my room and the door is shut

Ted>Oh God I'd love to I wish I could

Emily>Go ahead then (smile)

Ted>I can't I'm sorry wife is here

Ted>Oh God she would kill me if she knew

Emily realized if Ted's wife ever saw the picture it'd be disaster for Ted and Emily both, and she quickly typed her next message, so fast she didn't check for spelling.

Emily>Omg no youd better delete it niw

Emily>pls delete befpre she sees

Ted>I already did it's okay

Emily's short moment of panic quelled her arousal and she sat up in bed, her senses now so alert that she thought she could hear every sound in the house. No, her mother wasn't coming down the hall. Everything was normal. Everything was fine.

Ted>Hey

Emily>Yes?

Ted>It's okay I deleted it. But thank you so much that was amazing!

Emily>Hehe (smile) (blush)

Ted>Wish I didn't have to delete it (sad face) I could use it later for...stuff. (wink)

Emily>Haha you need to send me one back (wink)

Ted>Oh God don't tempt me girl...

Ted>The things I would do for you if I were younger...

Emily>Yeah? (smile) Like what? (smile)

Ted had never done anything like this. He'd been tempted at times to join chat rooms where strangers would usually pair off into private sessions and have what was popularly called "cybersex", but he never went any further than reading through the list of the names of the available rooms. What he was doing now was so removed from looking at pictures on his PC while enjoying a stroke.

He had stopped touching himself as well, but already regretted deleting the picture, knowing something like that would probably never happen again. He knew he had gone down a dangerous path and contemplated just how much farther he would explore it.

Ted>If I could get away later today, could I call you for just a few minutes? I've never done anything like this but I wish I could hear your vpice.

He didn't catch the typo until he had sent the text, and cursed himself for it; but she didn't seem to notice, or care.

Emily>Sure (smile) just text me first so I'll know

Emily>No one hardly ever bothers me if my door is shut (smile)

Emily>And if anyone comes in I'll say it's Sierra or somebody

Ted>Okay. I need to do some stuff first but I'll text you before. (smile)

Emily>Okay (smile)

Ted>You're amazing (smile)

Emily>hehe (smile)

Ted>Bye for now

Emily>Bye (smile)

Emily deleted the conversation from her phone to be safe. Her parents never looked at her phone, or asked to, but she didn't want to risk this being the one time it happened.

She opened her laptop and re-read the conversation from MySpace. Nothing bad there, just the offer to text. She left it.

She got up, put the laptop and her phone on her dresser, and went to her door and locked it. Going back to bed, she slid out of the boyshorts, noticing the damp place. She stashed the shorts under her pillow, reached for the Gatorade on her nightstand, and took a sip, enjoying the cool feeling as it went down her dry throat.

She laid back, and left the covers off. She looked down at her pale legs, which she hated. She thought her legs were fat, just like her ass, and most of the rest of her. Emily's self-image was distorted, by constant bombardment in advertising, film, and other popular media. Thin was sexy, fat was not. She was envious of girls like Sierra and Amy, and secretly enjoyed knowing at least she wasn't as big as Tawny. She'd never voice that out loud of course; she loved all her friends. Well, maybe Kayla was the exception; because Kayla had crossed Emily more than once by sharing secrets that should have been left untold. It was because of Kayla that everyone knew about the "lousy kisser" incident.

After that, Emily promised herself she'd never trust Kayla with sensitive secrets ever again. She was now glad she hadn't texted anyone earlier about her MySpace chat with Ted, because if Kayla had heard, it'd be all over the youth group by now.

Emily hooked her thumbs under the edge of her shirt, and slid it up over her breasts. Looking down over her almost-naked body, she wondered if any man would find her sexually attractive. "Maybe if they like chubby girls," she thought.

In reality, Emily had a very sexy body by almost any standards. The 36" bustline was matched by 36" hips, and a 24" waist. The first time she heard "Brick House" she giggled when she heard the line, "make an old man wish for younger days".

She let her fingers glide over her full breasts, teasing her nipples again. They responded and rose, and Emily circled each with a fingertip, watching how her pale skin reddened slightly at the tracks her nails made. This led her to try tracing lines on her breast, and then her belly. She watched how long the lines stayed, depending on how hard she pressed. She tried writing, but the lines faded before she could get much written.

Then she pressed harder, hard enough to make her wince, and her sharp nails made thin welts on her skin. She noted that while painful, the sensation was also sexually arousing.

She got up, and stood in front of her dresser mirror. She pulled the tee shirt over her head and looked at herself, imagining what a man would think of her like this; naked, and vulnerable.

She tried writing again, on her thigh, pressing hard enough to leave a mark again. She made an "E" and she could see it in the mirror, although it was reversed and upside down. Looking in the mirror this time, going slowly and carefully, she scratched out three letters on her stomach, just below her breasts.

T E D

She looked down at the red lines, her skin tingling from the marks she had made. In some of the places she had pressed too hard and there was a tiny amount of blood.

She looked back in the mirror. It was very easy to make out, very easy to read.

She picked up her phone, aimed at her reflection, and took a picture. This time, she positioned the phone far enough that her full body was visible, but her face just out of frame. She took a second picture, closer, to make sure the name was visible.

Taking the phone back to bed with her, she began to masturbate, while looking at the picture she had on her phone. She wanted more than anything to send the pictures to Ted, but knew that could cause massive problems if she didn't warn him first. She imagined how he would react at seeing her naked, not just a teasing picture this time, but actually seeing her boobs and pussy. Fully aroused now, she was no longer concerned that she might not be thin enough for Ted's tastes. She dropped the phone to the side. She imagined him stroking to the pictures she sent, wishing he could see her in person, just as she was in the pictures.

She fantasized about them secretly arranging a meeting at a hotel some day and letting him undress her. She imagined him kissing her, so passionately that her lips ached, and him holding her so tightly he lifted her off the floor. In her fantasy, he roughly dropped her on the hotel bed, hungry for her, and quickly removed her clothes, and his own.

Her fantasy lover started with kisses to her lips, but then quickly moved down her neck, and her breasts, licking, sucking, nibbling, even biting. She pinched her nipples with one hand as she imagined this, so hard that she gasped, and the pain, coupled with the fast strokes of the fingers of her other hand on her swollen clit brought her closer to orgasm.

She slid a finger inside herself, then two as she pictured him roughly probing her with his own fingers. Now curving her fingers back into a hook, she roughly pulled up, fast and hard, wishing it were really Ted that was forcing his fingers deeper and deeper inside her. Now with two fingers inside and her other hand rubbing her clit, she whispered Ted's name out loud with each pull. Moving so fast her words ran together into one long sound, "Tedtedteh... tehhedtehteh... hehhededed", she rode the crest of the most powerful orgasm she had ever experienced. Eyes closed, breathing in gasps, covered in perspiration, her body shuddered. Her legs straightened completely and her feet pointed straight down. Her back arched so hard she'd realize later she had sprained the muscles.

Once she relaxed, feeling the waves recede, and her breathing slowing, she opened her eyes and looked down at her naked body, now covered in sweat. Her belly barely showed the scratches now, but there were two small scrapes where she had pressed the hardest. She took a deep breath and sighed, and smiled.

End of part four.

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