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It was hard- in more ways than one- to fall asleep that night, even after some exercise and a cold shower. As I laid there in bed, I couldn't help but keep thinking of Emily telling me not to touch myself, and the pleasure she'd seemed to take in the idea, which (strangely) just made me press against my boxers even more desperately. Finally, I drifted off.
As soon as I woke up the next morning, I texted her:
"Hey Emily. You asked me to tell you how I was feeling in the morning, and...well...I can't wait to see you again. And I feel a little frustrated, to be honest."
About thirty minutes later, she texted back: "Only a little? :("
It occurred to me that she was loving this. I was too, but I was also a little nervous. Where was this heading? And what had she meant about a chastity device? She wasn't really going to...?
"Haha, okay, fine. A lot! I keep thinking about you. I...don't know how much longer I can manage this."
Her reply came back quickly: "Mike, it hasn't even been 24 hours! You can hold out for me, can't you?"
The thought of saying "no" was out of the question, and somehow I knew that I wouldn't be able to bring myself to cheat, either.
"You're making me tremble, Emily. Yes...yes, I can hold out."
A few minutes later: "Haha, good boy."
The endorphins ran through my brain again. Hearing that from her was suddenly better than a silly, fleeting orgasm.
A minute later: "Tell you what. Since you're being so good, I'm going to give you permission to ask me over three nights from now, on Wednesday."
I stared at that message for a few minutes, both incredibly relieved- surely I could hold out three days- and incredibly nervous. Not telling me all the rules immediately, letting me figure a few things out for myself, seemed to be part of the fun for her.
"Emily", I texted back, "would you like to come over on Wednesday night for some dinner and a movie?"
"That sounds wonderful. :)"
I became increasingly nervous- and increasingly horny- as Wednesday approached, and during the day I could hardly concentrate at work. Once I got back on Wednesday, I made sure to clean my kitchen and living room, have the Chinese food and wine ready (I'm not much of a cook), and to shower before Emily arrived. I chose khakis and a buttoned shirt, nothing overly formal, and just as I was looking at myself in the mirror and wondering if I should have shaved my beard, I heard the doorbell.
My heart pounded in my chest as I opened the door, and there was Emily, smiling. In no more than a few seconds, I breathed in her perfume- she smelled wonderful- and took in her smile, which was achingly pretty. She had on white blouse buttoned to the top, a loose black skirt, and a touch of pink lipstick, and her hair was down around her shoulders.
"Hi", I said, a little breathlessly.
"Hey", she smiled, and leaned upwards to kiss me on the lips. After our date, and after the three intervening days of not touching myself, my erection grew immediately in my pants, and my whole body started to shake, just a little. I moved my hand to her cheek, started to kiss her back, but after a second she broke away and smiled, swatting my hand.
"That's all for now, Mike", she smiled, walking past me. "That's the rule: I can kiss you, but you have to ask permission."
Somehow that just made me harder. "Permission. To...kiss you?"
She smiled back. "For everything. Wow, it looks like you really have prepared."
"Well, I tried...would you like some wine?"
"I would love some."
She sat down on the couch as I uncorked the wine and started to pour into two glasses. When I brought the glasses over and handed one to her, she took it and smiled. Sitting with her legs crossed under her black skirt and her flats off, she patted the couch next to her. "Sit down."
I took a deep breath and sat down, trying to get control of myself. To fortify myself and to gain some confidence, I put my glass of wine to my lips.
"Mike", Emily said, sounding patient but a little disappointed, "thank you for the wine, but aren't you forgetting something?" She was looking at my glass.
"Um."
"What did I say when I came in."
Then I remembered. Did she really mean...?
"Emily...", I began.
"Miss Emily. Or Mistress is fine, too."
"Miss Emily...may I have my glass of wine?"
"Please, Miss Emily."
"Please, Miss Emily...may I have my glass of wine?"
She clapped her hands, delighted, and laughed. "Oh yes, you may, Mike. I'm not that cruel."
I started to sip.
"But just one sip!"
I almost spit out the wine, and looked at her, astonished.
"Just kidding!"
I exhaled, trying to relax, and then took a longer sip while Emily watched me. I felt terribly exposed just sitting there like that, and I crossed my legs to feel less self-conscious, although I had the distinct impression that Emily wanted me to feel exposed.
I put the wine down on the coffee table, and I turned to Emily with my legs crossed, like hers, trying to seem casual.
"So", she said quietly, playing with the hem of her skirt. "You might be thinking, this is the part where she teases me. This is the part where she runs her foot up my leg, into my lap, or maybe straddles me, and gets me so close to cumming, makes me beg... Be honest: were you having any thoughts like that?"
"Well, I, um..."
"I'll take that as a yes", she giggled, still not touching me. I wanted nothing more than to reach over, pull her towards me, kiss her, make love to her...but I remembered what she's said, and somehow being obedient was so much better than displeasing her.
"I almost wore stockings today", she continued quietly, and she smiled as she watched me have what might have seemed like a mild seizure. "I could tell last time that you liked them."
"You...you could?" Was all I could think to say.
"Tell me, Mike- what did you like about them the most? The sound? The way they looked? Were you hoping that I would wear them again tonight?"
My dick was truly throbbing now- it was all I could do not to collapse on the floor in front of her in a puddle of abject sexual frustration- and all I could do was force out my answer through chattering teeth. "Yes...Mistress Emily", I managed, "although of course you look lovely anyway. As for what I liked the best, well...I do love the sound they made, but I think the way they looked on your long, beautiful legs was probably the thing I liked the best." I took another, longer sip of wine while Emily giggled.
"I see. Good to know. Maybe next time...I just wasn't sure you deserved it this time", she said, suddenly patting my erection gently and then taking her hand away before I knew what was happening. My body's involuntary response had me humping the air, while Emily giggled and I let out a garbled moan.
"I can see you have been good, though", she continued. "God, it's hard to keep a straight face sometimes. You boys are so, so...predictable." She paused, took a sip of her wine, and looked at me still dealing with the effects of her touch. "How does it feel to hump the air, Mike?"
My voice broke. "F...frustrating, Miss Emily", I muttered. "I...I want you so, so damn bad right now...please."
"Mmmm", she smiled. "I know you do." Suddenly, using just a few movements, she moved across the couch and straddled me, face-to-face, her forehead to mine.
"Oh God", I breathed, and my hands rose to both sides of her torso.
She raised her eyebrow. "Mike?"
Disbelieving, my expression no doubt showing desperation, I removed my hands. She was just sitting there, sitting against my erection, but not moving.
"Miss Emily", I moaned, "may I please...please touch you?"
She shook her head. "No, Mike. No touching." She pushed her forehead against mine again, and now our lips were almost touching. "You don't have permission. Hands at your sides", she whispered. "Now Mike...you know you're not going to cum tonight, right?"
I groaned, and my whole body squirmed in protest, my erection pressed against her lower thigh. She smiled, and her voice took on a particularly playful tone. "Right, Mike?"
I could barely believe my ears. And I could barely believe what I answered. "Right, Miss Emily", I groaned, even as my body screamed in desperation.
"Right about what, Mike?" she whispered, lips on my earlobe, perfume in my nostrils.
I groaned, almost wanting to cry. "I..."
"I didn't catch that, Mike."
"I'm...not going to...oh God...to cum tonight, Miss Emily."
"Or until I want you to again", she smiled wickedly.
"Or...until you want me to- oh God!- again", I managed, my whole body violently trembling now with desire.
"Good boy", she then said simply, and abruptly got up. My body was alone again, she was a few feet away, which suddenly seemed like an infinity of space. She straightened out her skirt and smiled up at me. She looked so lovely that I almost wanted to scream.
"So what now. Oh! Yes, I remember. I have something for you, Mike, something that will help you with our new arrangement. It's in my bag. While I get it...I assume you have an icepack in the freezer?"
I wasn't sure I liked where this was going. "Uh...yes", I answered weakly from the couch, still fighting the urge to hump the mattress, anything, to completion, which in this state wouldn't take more than a few seconds.
"Yes...who?"
"Yes, Miss Emily."
"Very good." She made eye contact with me. "Go get it and bring it here, while I get your...gift...from my bag."
I started to stand up, my erection, stuck in my pants, still stretched humiliatingly in front of me.
"Oh, Mike?"
"Yes, Miss Emily?" It was hard to even form words at this point, I was so worked up.
"Do you want to come here and kiss the hem of my skirt?"
My dick throbbed again, and I almost doubled over. "More than anything, Miss Emily", I said, starting to walk over to her.
"Good. I'm glad you do. Maybe later. For now, go get that ice. Chop-chop."
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