Summer in Amber Ch. 02

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Miss Amber forces Jacob out of his comfort zone.
5.6k words
4.59
22.8k
15

Part 2 of the 7 part series

Updated 06/09/2023
Created 12/04/2019
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I was getting ready for school when I received a text from an unknown number, and as soon as I read it I knew it was from Miss Amber. How did she get my number? I thought, but then I realized I didn't care. It read:

This will be your only reminder Jake. Absolutely no cumming unless I say so. THAT MEANS NO MASTURBATING. Save it all for me ;) - Miss A.

My classes went by in a complete blur that day. Lectures, homework, tests, nothing mattered except Miss Amber. She had made herself at home in my mind, and was occupying every vacant spot. What we did in the staff lounge, in secret and unknown to everyone else, was a huge turn on for me, and I could tell it was for her too, and from that point forward working at the library became thrilling. I used every possible excuse to spend as much time as I could in the children's section, putting away every cart there was, after which I would go back and shelf read, which was tedious work, but worth it to be around her.

Miss Amber wasted no time baiting me, and I became more bold in my leering. Nearly every day she wore something that accentuated her finest parts in different ways. She began switching it up, often changing out her usual dresses and skirts for dress pants that showed off the curves of her lower body. Sometimes I'd catch her bent down, ass in the air as she went to pick up her phone or some other item she dropped. I never could figure out if she was actually that clumsy or if she was taunting me, but regardless I relished the view as often as I could. Her pants were so well fit that I could make out the subtle shape of her ass, and I imagined what it felt like clasp it in my hands, or to give it a nice, firm slap. I hoped one day that I would.

Often times she'd unbutton her shirt, just enough to reveal an enticing amount of cleavage, always while making some offhand remark about the heat and lack of proper air conditioning. Again, I wasn't completely sure she was always doing this for my benefit, but that didn't stop me from staring. He tits were her best feature. Sometimes she'd lean forward and they looked like they were about to pop out of her shirt, and I'd wait with bated breath to catch a glimpse of a nipple. I wanted to see her nipples so bad. I wanted to feel them in my mouth and taste them. And I had to constantly remind myself that if I did exactly what she said, there was a chance that I would get my wish.

No matter how she teased me, I'd get hard every time, and every time she'd turn back, lock eyes with me, and smile that devilish smile of hers, her eyes trailing down to my erection, and I would blush, sheepishly smile back, and make no attempt to hide myself from her. She was catching me like this on a regular basis at this point, and her knowing, her acceptance, was the hottest part of all.

Those early days were full of uncertainty, and it took all of my will power not to masturbate; imagining what she was going to do to me, or have me do to her. I figured her foot job was just the tip of the iceberg, and I couldn't wait to experience what she had in store. But I was just as anxious as I was excited. I was deathly worried that I wouldn't be capable of pleasing her, which, given that at that point I was a late-blooming virgin, I figured was a guaranteed certainty. I hoped she would understand. I didn't want to ruin this opportunity. And the first step to make sure that didn't happen was to make sure not to break my promise. I wanted to wait for her, not just because of where it could possibly lead, but because I desperately wanted to please her. And as nervous as I was, I admit, I was also eager to learn.

All of this went on for an agonizing two weeks, and I could tell she was getting off on blueballing me. By the end it felt like I was bursting at the seams, and I desperately wanted relief more than anything.

Finally, as the annual Summer Reading Program was about to begin, I was informed by Sandy that Miss Amber had requested my help with sign ups. They were expecting record participants that year, and she thought having a partner at the desk would increase efficiency. I was told to head back to the children's department for training.

I was apprehensive about this because not only was this outside my normal responsibilities, but it would require interacting with people, specifically kids. I was not comfortable doing this, but then I thought about Miss Amber. I was fairly certain there was an ulterior motive to this request, so I had no choice but to put aside my anxiety and face my fears. If it meant being with her, it was worth it.

No matter what, do what she says, I reminded myself on my journey back to children's that day. I was nervous when I met her at the desk, and I did my best to hide it from her, but she saw right through me.

"Ah, there's the man of the hour," Miss Amber said, patting the rolling chair to her right. "Don't be nervous. Come, sit next to me. It's time to begin."

I slowly but eagerly shuffled over and sat down in the chair, and as I did she continued to stare at me, turning the pages of my mind. She had her hair up in a messy bun, and she was wearing a dark purple cardigan over a black tank top, along with matching tight fitting black pants. It was different from Miss Amber's usual way of dressing; less formal, but it suited her. She looked lovely, and the cherry on top was the thick rimmed rectangular glasses she was wearing. That was new, and it intrigued me.

"You're wearing glasses today," I said, "I've never seen you wear glasses." Seeing her wearing them now though, I wished she had more often. Miss Amber was already a potent combination of beauty and intelligence, and those glasses really enhanced the effect.

"Yeah, they're non-prescription. Sometimes I like to wear them to see if people treat me differently. And for special occasions of course." She looked down for a second then back at me. "What do you think?"

I inhaled slightly. "I think they look great on you, Miss Amber." Saying that made me scream inside, and I clenched up, instinctively waiting for rejection. I was starting to sweat.

Instead, she smiled appreciatively. "Thanks. I knew you'd like them."

Being near Miss Amber was intoxicating. My heart pounded as I tried to think of something else to say, and I blurted out the first thing that came to mind. "So, I'm supposed to help you with Summer Reading sign ups?"

Miss Amber looked amused. "Don't worry yourself about that Jake," she said. "It's easy, it'll take me ten, fifteen minutes tops to show you. There's no rush." She leaned in towards me, her hand creeping towards mine. I was trembling, and she noticed. A look of pity crossed her face.

"You poor boy. You really are a mess, aren't you?" Miss Amber gently grabbed my hand and held it in hers, lightly caressing my finger tips. "Do you trust me?" she asked warmly.

I felt the sensitivity of her fingers on mine, and I looked into her green eyes, seeing her intentions. "Yes."

"That's good Jake. You're such a smart young man. Soon you won't recognize yourself."

Miss Amber's words and her touch began to calm me down, and soon the tremors and the tornado of intrusive thoughts subsided.

"Are you ready?" she invited.

"Yeah," I gasped out, equal parts elated and panicked.

"Say yes Miss Amber, I'm ready."

"Yes Miss Amber, I-"

"Say it louder," she interrupted, the warmth in her voice replaced by cold, unflinching insistence. This was not a request.

I looked around, trying to scan the library for people. She squeezed my hand, bringing me back to her.

"Never mind them. Say it."

"Yes Miss Amber, I'm ready," I said loud and clear.

She let go of me and leaned back into her chair. "Good," she said, crossing her legs. "Today is very simple. I just need to see what you can do. Show me."

"Um, show you what?" I asked, feigning ignorance. I knew exactly what she meant.

"Don't play dumb. Show it to me."

"Really, right here? What if somebody sees?"

Miss Amber looked annoyed. "What did I tell you Jake?"

I flinched, remembering her one rule. "Do exactly what you say."

"That's right. Do I have to repeat myself? If you're gonna go on like this then I'm done with you. Understand?"

"I understand," I said, resigned.

"Good. Now right now I want you to show me what I've been waiting for."

I reached down and began unzipping my jeans. My hands were back to shaking, but then I saw an unmistakable look of desire in Miss Amber. I stopped trembling and blood started rushing to my cock. I was getting hard fast.

"Go on," she said, biting her lip.

I slowly unzipped my jeans and pulled them down just below my knees, revealing my boxers, and my quickly growing cock sprouting out of the fly.

Miss Amber let out a faint whimper of frustration. "Hurry up, I wanna see you," she insisted.

As far as I could tell the children's department was empty. It was now or never. I couldn't believe I was actually doing this. I reached in through the fly and pulled out my slender, now fully erect cock. At six and a half inches, I was slightly above average, the effect of which was enhanced by my naturally thin frame.

Miss Amber's green eyes lit up, and she leaned down to get a better look. "Not bad Jake. I like the little birth mark on the tip. Gives it personality."

Her remark drew a timid laugh from me, and then, to my surprise, I thought of something bold to say in return.

"You're always welcome to get to know it better," I suggested in my first ever attempt to be provocative.

Miss Amber looked startled and giggled slightly. "Oh my, I walked right into the one didn't I? Maybe there's hope for you after all."

We smiled at each other, and she looked radiant. She leaned down under the table and positioned a trash can at the front of my chair, just below my cock.

"Now give me what I want," she ordered. "I wanna watch you stroke your cock right now. Let's see how long you can last."

Miss Amber leaned back into her chair as I gave the room one last quick survey before gripping myself with my right hand. Precum was already starting to leak out of me like a faucet as I began stroking, slowly and methodically traversing the entirety of my shaft. Despite my intense fear of getting caught, I wanted to last as long as possible for her, so I took my time, praying that I had the strength within to endure.

I turned to see her watching me intently, her eyes locked onto my cock, her lips wet with moisture, her chest heaving ever so slightly to the rhythm of her quickening breath. She looked excited, and it was getting me excited. Too excited.

Suddenly I felt the flood gates open and a wave washed over me. No, not yet, I thought as I tried to hold on, but it was to no avail. I let go, splashing weeks worth of myself against the side and bottom of the trash can. I convulsed and groaned with humiliation.

It was exactly what I feared and expected would happen. I had barely lasted thirty seconds, and I didn't even have to look at Miss Amber to know what she was thinking. I felt ashamed.

"Oh Jake," she bemoaned, "this simply will not do. You'll never satisfy me like that."

She grabbed a tissue off the desk and leaned in close, resting one hand on my bare inner thigh, and tenderly dabbed the head of my cock, wiping up the residual semen.

"Can you last longer for me next time?" she sweetly asked, throwing the tissue in the trash.

"Yeah," I said, eager to please even if I wasn't sure I ever could. "I mean, I think so."

Miss Amber grabbed my softening cock and lovingly guided me back into my boxers. My shame began to vanish.

"Do you promise?" she asked, pulling my jeans back up to my waist. "Say yes Miss Amber, I promise."

"Yes Miss Amber, I promise. I'd do anything for you." That last part came out unexpectedly. If she was turned off by my sudden and awkwardly proclaimed admiration, she didn't show it.

"Good," she said zipping me up, "I expect you to do better from now on, and as long as you keep showing progress we'll keep going. How does that sound?"

"Whatever you want," I said to her, soaking in her unbelievable sexiness.

Miss Amber smiled, drew her face in towards mine, lifted me by the chin with a single finger, and planted a light red kiss on my left cheek.

"That's what I like to hear," she whispered, and in an instant I was hard again.

II.

As I laid in bed that night it felt like electricity was coursing through my veins. It was hard for me to wrap my head around what had happened. Not only had I shown my cock to Miss Amber, and not only had she watched me jerk off, but we did it in public, where anybody could've seen. I was lucky nobody did. Not that there was much of a chance for that to happen. I was pissed at myself for coming as quick as I did; it made me feel pathetic. As I hoped though, Miss Amber was reasonable and was giving me the chance to prove myself. And I was determined to do that, whatever it took.

She really was quite the woman. The way she could be so gentle yet so forceful drove me crazy with lust. She was always in control, and I loved that about her. It felt like she was drawing something out of me, as if she had me under her spell, and I was more than happy to submit.

Once Summer Reading was officially underway, I started spending half of my shifts at the children's desk helping Miss Amber. I was back there every day, signing up families, stamping reading logs, and handing out stickers to wide-eyed children. While I was not the least bit enthused about doing this at first, it didn't take long for me to get the hang of it. Miss Amber was right; it was easy, and I began to realize there was nothing to get anxious about. Soon I started to legitimately enjoy working in children's, especially because I got to see her librarian skills in action first hand. It was obvious why she was hired; she was a natural with kids. It was heartwarming seeing so many of them light up with excitement explaining to her how they read twenty books in a week, and to see her earnestly reflect their joy back to them.

What Miss Amber and I were doing in secret however was obviously the real draw. Whenever there was a lull in activity, she'd order me to show her how long I could last, and I'd obey. I had no idea how we were getting away with this so often; it was almost like she had a sixth sense or something. She'd watch me, observing me as I stroked my cock, and I'd watch her and do everything I could not to come, which was no easy task.

Eventually though I grew accustomed to Miss Amber's presence, and I found that the more I focused all of my attention on pleasing her the easier it became to control myself. She no longer merely excited me; I began to feel relaxed and comfortable around her, and the more comfortable I was the longer I lasted, and she'd give me delicious words of encouragement that made the wait worth it, followed by a gentle kiss on my cheek. Those alone incentivized me to do better.

There was one time however where we did almost get caught, and I'll never forget it.

It was finals week and my time with community college was finally coming to an end, with so much weighing on my mind. I still wasn't sure what I wanted to do next with less than three months to figure it out. The more immediate threat at that moment however was speech class. The final was to give a fifteen minute presentation, and I felt like I was carrying butterflies in my stomach for days in anticipation. I was dreading it like a prisoner dreads the firing squad. At least I had Miss Amber to carry me forward. She was the highlight of every day.

Also around this time I admit I was starting to get restless, wondering when Miss Amber was going to take it to the next level. I liked having her watch me jerk off, it was hot, but there was so much more I wanted to do with her. It had been weeks since we made our deal and so far all she had done was watch me. I was being impatient, but at the same time I trusted her. I figured she knew what she was doing, and so as frustrated as I was, I always understood. Who was I to question her?

That day when I sat down next to Miss Amber at the children's desk she could tell my head was heavy.

"Let me guess. Speech class?" she guessed thoughtfully.

"Yeah. I have to give my final presentation next Thursday," I confessed. "To say I'm not looking forward to it is an understatement."

Miss Amber sighed, looking at me sympathetically. She was dressed classy that day, wearing an a-line denim blue dress. She had her glasses on again, and her auburn hair was lose and wavy, draping over her shoulders and perfectly framing her porcelain white face on both sides.

"Jake, you know what I always remind myself of when I feel anxious or uncertain?" she said, reaching out and parting a strand of curly hair away from my forehead. "That the world doesn't give a shit about me."

I admit, this wasn't exactly the life affirming wisdom I expected, and it went against so much of the "you are special" affirmations that were hammered into my head as a kid. I was slightly confused, and Miss Amber could tell.

"Let me ask you something," she said, leaning back in her chair and crossing her arms, "how do you think your other classmates are feeling?"

I already knew where this was going, and I didn't want to hear it.

"Yeah, I know, everyone is afraid of public speaking," I snapped, "but not as much as I am. Everyone makes it look so easy while I'm up there embarrassing myself."

The way Miss Amber looked at me, down through her glasses, made me realize how rude I was being. She was trying to help and I wasn't listening. This wasn't like me, and I felt ashamed.

"I'm sorry Miss Amber," I said, hanging my head down. "There's just...a lot on my mind."

Miss Amber reached out and lifted me by the chin, forcing my eyes back to her. "And how many of the other kids in your class are too busy going through the exact same thing to care about what you're feeling?"

Suddenly it all clicked, and I knew exactly what she was trying to tell me.

"I know," I conceded, "I need to stop caring about what other people think."

"That's exactly what you need to do silly," she leveled with me. "Nobody cares; they've got their own problems to deal with. Everybody in that class will forget about your speech an hour after seeing it. You just need to do your best and get it over with."

Miss Amber could see that I was processing what she was saying, and seized the opportunity to work her magic. She grabbed my left hand and began caressing my fingers, forcing all of my attention to her, allowing me to absorb her comforting beauty.

"You know what your problem is? You're too stuck in that noggin of yours," she said, playfully flicking me on the forehead with her middle finger. "It keeps you from getting what you want."

She was looking straight into me, empathy in her eyes. "What do you want Jake?"

There was only one thing I wanted, and she was sitting directly in front of me.

"Just calm yourself and let go," Miss Amber said. "Get out of your head and share yourself with others. It can be painful sometimes but the rewards are worth it. You just have to let go. Do you understand what I'm saying?"

The butterflies started to clear. I knew Miss Amber was right, and in many ways I had always known. It just became more real hearing her say it. She sat my hand back down into my lap.

"Do you understand?" she repeated sternly.

"Yes Miss Amber, I understand," I said, doing my best to appear confident, but she looked skeptical.

"Hmm, I'm not so sure you do. I think we're gonna have to put your resolve to the test" she said, tracing her finger down my chest to my groin. "Show me your pretty cock again, I wanna see it."

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