Miss

In the spring of my senior year of high school, another student and I were selected to attend a leadership weekend sponsored by a national organization.

"We're both eighteen," I argued when I learned our history teacher was to go along as chaperone, throwing in a few gratuitous references to being able to vote, own a gun, jump off a cliff.[OK, I didn't put that last one in there, just wanted to see if anyone was paying attention. I thought it though...perhaps in my valiant, quixotic attempt to debate the impossible, I'd gotten my metaphors mixed.]

"But it's aLEADERSHIP conference!" I moaned when the administrator, Miss Anastasia, remained unmoved by my rhetoric. "What kind of leader needs a chaperone?" What I wanted to say was, "What fucking kind of fucking leader fucking needs a fucking chaperone?" You know, using adjectives to emphasize and clarify a point.

"It's not just school policy," Miss Anastasia explained, "the conference won't accept unescorted students. Do you understand, Blaine?"

I was looking out her window, sighing inappropriately loudly with a degree of petulance only teenagers and toddlers can muster.

"Look at me, Blaine!" Miss Anastasia said sharply. Then, when my eyes were focused on her incredibly beautiful countenance (part of the reason for looking out the window was self defense because staring at that face, with those ruby-red, pouty lips, for too long would give me a hard-on), she asked again if I understood.

"Yes, Miss," I answered. I don't think it was a school rule or anything that students call her that, but we all did. Never "Miss Anastasia" just "Miss" even when we were talking among ourselves. "Did you see how hot Miss looks today? Christ I'd like to tap that!"

Our history teacher cum chaperone, Mrs. Stevens had graying hair and was overweight. Her bulk, though, was very well distributed as she had huge titties, a trim waistline for her size, rounded hips, and a nice plump ass. She often wore tight sweaters with plunging necklines. I'm sure most of the boys in her class had fantasies about her. I know I did.

Even her legs were shapely and she wore her skirts short to show them off. Some times she would move her chair from behind her desk, sit at the front of the class and read to us. She would cross and uncross her legs and we would all try to catch a glimpse of her panties but she was always so careful. It was like she was taunting us, saying, I may be a chubby fifty-year-old but there's not one of you who wouldn't fuck me if he had the chance.

I had a reputation among the students for having a big cock. In private, some of the girls would tease me about it and ask me for it. Some of them got their wishes. Emily, the other student on the weekend with me, hadn't been one of those girls. We weren't very close outside class and I figured she just wasn't interested.

Saturday night, however, I got a call from Emily in my hotel room. She asked me to come over to her room. I told her we weren't allowed to do that. She said no one would know (we had assigned roommates from other schools but Emily's hadn't shown up). I told her no, that it was too risky.

She said please, that she had a question about the reading assignment we'd been given. When a pretty girl says please to me, I have a very difficult time refusing. I checked the hallway and snuck down to her room.

As soon as I was inside, she said, "Show it to me."

"The assignment?" I asked, confused. How would I know what part of the assignment she wanted help with?

"No, she said, 'IT'" I just stood there. I had no idea what she was talking about, that's how dumb I was. "Your dick," she said smiling. "I want to see what everyone is talking about. Ever since I found out we were going on this trip together I've been dying to see what it looks like."

I told her no, that we'd be sent home if we were caught. She began making sounds like a chicken, trying to taunt me into showing her. She also said she wouldn't be sent home because who would believe an innocent girl like her had asked for such a nasty thing.

She went behind me and began rubbing her body against me. She put her hands around my waist and pulled me back into her. She started rubbing my chest and told me she'd suck it if I took it out.

I spun around and started tickling her to make her let me go. I wanted what she promised but was too scared of getting caught. I had just thrown Emily on the bed and was continuing to tickle her when Mrs. Stevens walked in.

I immediately jumped up and Emily pushed her skirt down her legs where it had ridden up very high.

"It's Blaine, Mrs. Stevens," Emily accused immediately.

"Blaine what?" she asked.

"H-he," Emily stammered, "he's got something in his pants and he's threatening me with it."

I could see that Emily was almost ready to burst out laughing but Mrs. Stevens took her statement at face value.

"What is it Blaine?" Mrs. Stevens asked, immediately taking Emily's side.

"There's nothing," I said.

"Why would she make up such a thing?"

"I have no idea," I lied, not wanting to tell the truth. Emily stuck her tongue out at me when Mrs. Stevens wasn't looking.

"Show me, Blaine," the teacher I'd fantasized about ordered.

"Show you what?"

"Show me what Emily is talking about." I didn't know what to do so I just stood there. "Show me right now or I'll send you home tonight! I doubt your parents will be pleased with you being caught alone in a young lady's room."

I got a little pissed off because I'd done nothing but try to be good and now I was the one to be punished. So I did it. I unzipped my pants and took out my cock. I let it hang in front of my fly.

Mrs. Steven's jaw dropped. She wasn't breathing and Emily was nearly hyperventilating as they stared at my long, fat, flaccid, black cock. After about a minute, I became concerned with Mrs. Stevens' lack of respiration.

"Would you like to touch it, ma'am?" I asked, taking a step towards Mrs. Stevens, finally breaking her hypnosis. If student sex was what this chubby old teacher wanted, I had her covered. Instantaneously, she regained her composure and got very stern.

"Put that away young man and go back to your room! And don't ever speak of this to anyone," she scolded.

I quickly put it away and practically ran from the room, so glad to be out of trouble. I barely got back to my room when Emily called. She was giggling and laughing and told me Mrs. Stevens was gone. She wanted me to sneak back into her room.

"But your cock is so beautiful," she said sweetly when I refused. "I promise I'll be so nice to it. You won't be sorry."

"I already am," I told her and hung up.

No sooner had I hung up on Emily than the phone rang again.

"Listen," I said almost shouting, "I told you I'm not coming back to your room! Leave me the fuck al..."

"BLAINE!" came the sharp retort of a female voice but not Emily's. It wasn't Mrs. Stevens' either. I immediately fell silent.

"This is Miss Anastasia," the voice continued. She'd lowered the volume but increased the degree of firmness.

"Yes, Miss," I uttered when she paused, awaiting confirmation from me.

"Mrs. Stevens just reported what you did to Emily and her. You need to report to me.

Miss Anastasia is a member of the school administration although she is far too young for her position. She is in her late twenties and, by far, the most beautiful member of the staff.

"Yes, Miss," I answered dejectedly. I wasn't out of the woods yet. "Should I report to your office on Monday?"

Even though I was upset that there would be punishment yet to come, just the thought of sitting alone with Miss Anastasia, excited me. I had already begun formulating the fantasy that I would use to jerk off when I got under the covers that night.

"Not Monday, now," she ordered in a calm, steady, but demanding voice.

"I-I..." I stuttered, not comprehending. Was I being ordered home? At this hour? How would I get there? Was I to go to her house? On Saturday night? I didn't even know where she lived.

"I'm at the hotel, Blaine," Miss Anastasia said more soothingly, sensing my panic. "I'm a member of the committee that sponsors this conference. "Now, please report to room 722." She'd said "please" but her words were a command.

Not only was she staying at the hotel, but we were on the same floor! I walked down the hall and knocked on her door. When she let me in, I was stunned. I had never seen her, never seen any teacher dressed like that.

She wore a red sequined gown. On her feet were red, patent leather platform shoes consisting of several strips of shiny red leather that wrapped the arch of her foot, her heels, and her ankles on top and clear plastic platforms with seven-inch heels on the bottom. Her toenails were painted the same color red as the shoes and the dress, and matched her fingernails and lipstick. In those shoes, she was even taller than I.

I noticed when she turned to re-enter her room the dress had almost no back, plunging nearly to the swell of her ass. All I saw was the clear, milky skin that looked to be the very definition of softness. I watched the swish of her hips and heard the gentle rustle of one nylon encased thigh rubbing against its twin as she led me into her room.

Her lovely blonde hair flowed over her shoulders and down her back. Stopping in the middle of the room, she turned and faced me. Despite a reputation for firmness with the students, Miss Anastasia has the face of an angel.

Her makeup was done perfectly, the blush on her cheeks, the shadow above the eye, the gooey red slickness on those pouting lips. I had to look quickly away from her mouth as I felt a jolt in my loins and my cock began to harden. I must be very careful about avoiding erections because of my size.

I wanted to look at the floor in my embarrassment about why I stood where I did. Instead, I found my gaze drawn to her eyes, bluish, greenish, grayish, steeled by resolve, those bright eyes began drawing me into them. I couldn't so much as blink.

"You're beautiful," I murmured though my voice was so dry it cracked.

"We're not on a date, Blaine!" she snapped. Then, as if softening to acknowledge the compliment said, "I've just come from a committee dinner. Now tell me what happened,"

Miss Anastasia's order was issued with a calmness of someone asking me to describe how the milk had been spilt rather than what I was doing taking my dick out in front of my teacher and a fellow student.

"Emily and I were just kidding around a little," I began. My first thought was to tell a lie to mitigate any guilt.

"I'm not interested in whatever bullshit you think you can spin to get yourself out of this, young man," she scolded. "I want the truth. Why were you in Emily's room?" I was shocked to hear a school official use such coarse language.

"She was having trouble with the assignment and asked me to come help her," I answered giving a half-truth.

"That's a lie," Miss Anastasia accused, "or at the very least, not the whole truth. When Mrs. Stevens entered, you had Emily on the bed. Her skirt was up about her waist. Mrs. Stevens could see her panties. That doesn't sound like collaborating on an assignment to me. What were you doing?"

"I was tickling her," I answered honestly.

"Why?"

"She had deceived me," I answered without thinking about how I might explain what I meant by that.

"Deceived you how?" Miss Anastasia asked.

"She hadn't really wanted to study," I answered feeling suddenly trapped.

"What had she wanted?"

My eyes went to the floor. I stood silently. "S-she wanted..." my voice drifted off, not completing my thought.

"The truth, Blaine! And I mean it!"

"She wanted me to show her my penis," I answered dejectedly. I felt my face flush hot. I was blushing but it wasn't noticeable under my black skin.

"Why did Emily want to see your cock?" Miss Anastasia asked, again using language I'd never thought appropriate for use with a vice-principal.

"She said she heard it was big," I answered. Suddenly I felt a burden lifted from my shoulders. The truth was out. I didn't need to lie anymore.

"Is it?" Miss Anastasia asked. "Is your cock big?"

"Well, I don't exactly know," reverting back to hedging my answers again. Then determined not to do that, I continued. "Some people say it is."

"Big or very big?" she asked. The entire grilling was being conducted with her steely gaze on me.

"Very, very big," I answered, feeling an unwanted smile creep across my lips.

"Do you think this is funny, young man?"

"No, Miss."

"Your impudence is causing me to doubt your veracity."

"No, Miss, it's true. And that's why Emily wanted me to come to her room."

"First you fabricate, then you become cheeky, I feel I can no longer take you at your word, Blaine. You will have to prove it to me. Strip off those clothes."

I started to protest but quickly realized it would be useless. Tugging down my zipper, I was prepared to expose myself to a third female in the space of half an hour.

"No, Blaine," Miss Anastasia corrected, "I don't want you to just pull out your dick like you did for Mrs. Stevens and Emily. I want you to strip naked.

"But..." I started to say before my protest was silenced by a sharp look from Miss Anastasia.

I began unbuttoning my shirt, pulling the tails out of my slacks, unfastening the cuffs, and sliding it down my arms.

Seeing the confusion in my eyes over where I should put the garment, she said, "On the floor," and pointed to an out-of-the-way place next to the nightstand.

I lay my shirt down carefully, pulled my undershirt over my head and set it on top my shirt. I kicked off my shoes and placed them next to the shirt. As I was removing my socks, I realized that, despite my nervousness, I was getting excited undressing for this gorgeous woman.

As I unbuckled my belt, Miss Anastasia walked around behind me, scrutinizing my body. When she got back to the front, I pushed both my pants and boxer shorts down at once. She wanted to see it, so there it was. I thought I saw a glimmer of desire in her hard eyes as I kicked my pants toward the rest of my clothes.

Miss Anastasia began circling me again. She let a sharp fingernail trail down my chest to my abdominal muscles. She said I must do a lot of sit-ups. At least two hundred a day I told her. She pinched the taut skin where love handles sprout but found nothing but firm musculature.

Continuing, she moved her hand over my forearm and hip. When she was behind me again, I felt her cup my buttock and squeeze. Her nails dug painfully into my flesh but amazingly it aroused more than that it hurt. Up my back and over my shoulder she traced, and she was back in front of me again.

"Is that what Emily was so interested in?" Miss Anastasia asked, looking squarely at my semi-hard, black cock.

"Yes, Miss," I confirmed.

"Stroke it," she commanded. "Get it hard so Miss can see exactly what that poor girl was threatened with." I took my cock in my hand and began masturbating.

"Is that how you jerk off?" she asked.

"Yes, Miss, sometimes," I answered.

"What else do you do?" she asked.

"Usually, I use both hands."

"Show me."

I grabbed my dick with both hands and started jerking it. It immediately got completely hard.

"You see, Miss?" I said, trying to confirm my earlier veracity "You see how much still sticks out even when I have both hands on it. It is very, very big, isn't it?"

"Yes, Blaine," Miss Anastasia conceded, "your cock is indeed quite large."

Between the stroking and having such a beautiful older woman say something nice about my dick, I was rapidly approaching orgasm.

"Miss!" I said urgently, "if I don't stop soon, I'm gonna cu..."

Miss Anastasia slapped my hands harshly away from my phallus, scraping a fingernail sharply across the cock head in the process. I took my hands away immediately, leaving my cock to stick straight out and throb unattended. A pearl of precum glistened at the slit.

"Young boys like you are always behaving inappropriately, Blaine," Miss Anastasia snapped, spoiling my mood. "You need to learn there's more to life than just those always demanding erections of yours. Now, down on your knees so we can drive some of this sass out of you."

I had no idea sass what she was talking about but I quickly got on my knees. My eyes popped open and my cock hurriedly re-engorged as I watched Miss Anastasia slowly slide her dress up her thighs. Her legs were that same lovely shade as the skin of her back I'd admired earlier. It was like I was looking at the surface of the liquid in a cream pitcher.

Her dress went higher and higher until a triangular patch of shiny red the same color as the dress, it even had matching sequins, appeared as she exposed her panties to me. How this was supposed to knock the sass out of me I wasn't certain. My cock bobbed wildly as I ogled that beautiful red Vee before me. I felt a string a precum dangle then drop to the carpet.

"Lick it," Miss Anastasia ordered, pulling those red panties to the side.

I pressed my face forward inhaling a wonderfully musky aroma and kissed her bare mound. Shifting her feet to achieve a wider stance, I was allowed to wriggle my tongue partway down between her juicy labia, slipping it across her clitoris as I went. I felt a shudder go through her body. I continued jabbing my tongue against the juncture of her thighs but was having a little difficulty getting it in as far as she wanted.

"Wait," Miss said with some urgency, pushing my face away from her crotch. "Take these off," she said hooking a thumb into her panties. I slid them slowly down her silky legs enjoying the feel of her nylon covered skin.

When the red thong reached the floor, she quickly kicked it aside and hooked a leg over my shoulder and behind my back. With her new leverage, she pulled my face back against her pussy. I began lapping frantically while my desperate dick swayed from side to side untouched and unsatisfied.

I reached between her legs, bringing my hands up to her ass in an effort to pull myself even closer to her now sloppy hole. Miss Anastasia let her dress drop down over the back of my head and I knelt, partly concealed with my head up her dress. She grabbed that portion of the dress containing my head with both hands, holding it firmly in place. It must have appeared as if she were trying to shove a bowling ball into her cunt.

Suddenly, she shuddered violently, and cried out. "Oh shit!" she screamed, OH FUCK!!! Eat that pussy you big cocked bastard!! Oh fuck, oh fuck, oh fuck, YOU'RE MAKING ME CUUUUUMMMMMM!!!!!!!!!!!!!!!"

I licked and tongued as fiercely as I could, enjoying her climax almost as much as I would my own. I wanted desperately to reach down and finish what I'd started before Miss slapped my hands away but I didn't dare. I worried what Miss would say. Besides, maybe she'd want me to do something else, something of mutual pleasure and I would have wasted myself.

Breathing raggedly, Miss disentangled herself and her dress from me and slumped back on the bed. She lay recuperating with her eyes closed for perhaps ten minutes. I remained kneeling on the floor where I'd most recently been ordered, my dick sore and throbbing. My balls were beginning to ache.

Sighing deeply and opening her eyes, Miss commanded, "Bring me your cock."

I stood up and walked to the bed. Miss Anastasia rolled onto her side and took my cock in her hand. "I can't take all of this," she explained, stroking it, "but I want you to put as much in as will fit. Just don't slam into my cervix. Do you understand?"

I nodded and got onto the bed as Miss again lifted her dress over her hips. I placed my arms outside her shoulders and pressed the head of my cock against her slit. She was soaking wet from my saliva and her juices. The head and several inches of shaft slid easily in. When she tensed, I stopped and waited for her to adjust to my size.