The Naughty Chaperone

THE NAUGHTY CHAPERONE

I am a very suspicious and unemotional woman.

Yes, I am fully aware that the other teachers in my school call me “The tight-assed bitch”. I can’t help that. It is just the way that I am. I would like to be open and bubbling with enthusiasm but I always get bogged down in analyzing the consequences.

Here I am almost 25 years old and I am still a virgin. It is not because I am unattractive. I don’t want to brag or seem like an egomaniac but I am what guys call “stacked”.

Ever since I was about 21 and out on my own, I have relied on my toys to keep me satisfied physically. When I have used them vigorously, I am able to fall into a relaxing sleep. Admittedly it is an act of completion that I would refer to as the “dirty deed”.

I don’t know when I started to think of sex as being dirty or for that matter to think of sex at all until shortly after my sixteenth birthday. Late one night I was very restless in my bed and my daddy caught me with my hand up there in that nice spot between my legs. I think the sweet smile on my face made him very angry and he pulled me over his knee. It was the worst spanking I had ever gotten. I can still remember the way he yelled at me,

“You dirty filthy little girl. You are going to be a slut just like your mum. You are nothing but a silly, stupid little bitch and will probably spread your legs at the first opportunity.”

My tender little bottom was so sore I was unable to sit on it for two days. I vowed right then and there to be a good little girl and not to spread my legs for anyone except my anticipated soul-mate. That was almost 10 years ago and I have not seen anyone even vaguely resembling a true soul-mate in all that time. My only soul-mate was my 8 inch black dildo which I had affectionately christened “James”.

I didn’t know any guy called James other than “007”. My James was well acquainted with my pussy and on those special occasions when I wanted something a little different, my tight little pucker hole. When I used it like that I felt so dirty I always had to take a shower and repeat to myself in the mirror,

“I am a good girl. A very good girl. I don’t ever do that sort of thing. I am not that kind of girl.”

It is not that I have not had a number of dates with attractive, interesting men. Only last week I had a dinner at an upscale restaurant with a recently divorced Pediatrician. He was only in his mid-thirties and his only drawback seemed to be a bad case of dandruff. He kissed me several times in the car and was upset when I pushed his hand out of my lap before he could start an exam of my pelvis. I told him I liked him but was not ready to grant him carnal knowledge of my private places just yet. I was not surprised when he did not call back as promised. It was typical of all my relationships that never seemed to go anywhere at all.

I am pretty sure I am not a lesbian.

I mean, I like women a lot. I love to look at nude women. I love the pretty nipples and the pert breasts so nicely outstanding. I even like to look at older women. I think breasts and bottoms that sag a bit and laugh crinkles around the eyes and mouth are really sexy. Almost every attractive mature woman I have met makes me feel sexier. I think of what it would be like to wrap my arms and legs around her and cover her face with kisses. But I don’t think I am a lesbian because I have such a desire to have a big long fat cock stuffed inside me and pounding me into complete submission.

I knew that one of my students had a crush on me. I have absolutely no idea for what reason. Her name is Alice. Alice is a lovely girl. She was particularly well developed for her age of 17 and has the sweetest disposition with a smile for everyone.

She was my teacher’s assistant in the sixth period and usually helped me to grade the endless papers and tests that always piled up at the end of each and every day.

I noticed one afternoon that she was keeping her head down on the work in front of her and did not look at me. I walked down and asked her,

“What is the matter, Alice? Are you not feeling well?”

When she looked up at me, I could see two perfectly formed teardrops forming in the corners of her lovely blue eyes and a little sob escaped her lips.

“Oh, Miss! I can’t stand it any longer. I just have to put my hand up your skirt and pet you with my finger. Please, Miss, just a little touch and I will be a good girl, I promise.”

I was a little taken aback that the pretty young thing would voice her hidden desires so openly and looked about to make certain we were quite alone. I knew they had been discussing cams in the classroom but decided not to institute them because of the high cost of the project.

My heart went out to this young girl. She reminded me of me when I was younger. I knew she would be astonished to know I was a virgin because nowadays most of the 17 and 18 year old females had lost their cherries in all three orifices as a rite of passage fully accepted.

I stood over Alice and wrapped my arms around her head and shoulders. I stroked her hair to comfort her in her excited state of mind. Somehow, her face got buried into my pubic mound and I could feel the outline of her chin, her mouth, her nose thru the thin cotton material of my short skirt. The proximity of her mouth to my slit made my pussy juices start to leak and I could feel the wetness seeping thru my frilly silk panties.

The simple truth is I was really enjoying her attentions to my pussy and I made no move to stop her hands from grasping my ass cheeks and squeezing them with her strong fingers. Alice was quite the soccer player and was probably the fittest young lady in the senior class. Her head was now firmly pushed deep in between my legs and I am ashamed to say I spread my knees to let her get in nice and deep. The emotions that I felt were overwhelming. I really wished she were a man and could be my proper soul-mate, but I was happy she was a lovely, pretty young girl with her own feminine form to inspire my passion.

I was so enthused with her ministrations that I pulled up my skirt in front and could feel the touch of her smooth skin and lips against my fuzzy little slit. She must have liked it because her tongue was working overtime to lick up my leaking pussy juice before it ran down the inside of my legs.

“Miss, I have to get my tongue inside. Open your legs wider please, Miss.”

I complied without thought or reason. The flutter of that wet pointed tongue inside my pussy brought me to an instantaneous orgasm that made me convulse with utter lack of control. I remember yelling at the poor girl,

“Right there, you little bitch! Suck me nice and proper, little Alice. If you do a good job, I will let you do the same to my poop hole. Lick it all up nice for mama.”

I was so embarrassed. How could I have said such dirty things?

Alice loved it. She kissed my hand and my lips and told me,

“Thank you ever so much, Miss! I will do anything for you. I love you so very much.”

The girl ran out of my classroom and I composed myself. It was probably the most satisfying sexual experience I had ever had in my entire life. I just couldn’t understand how it could have been with another female and not my long-awaited male soul-mate.

It was time for the Halloween dance. That was always a big event at our school. I think it was more tradition than for any special reason. All of us teachers were expected to be chaperones and keep the students from finding ways to copulate on school grounds. The parents had also volunteered to assist us and several of the parents attended our meeting the night before the party.

I was serving the coffee and cupcakes like I usually do and looked up to see the sexiest man I had ever gazed upon reaching out his hand to take a cupcake from my fingers. I wanted to grab his hand and pull him down to the floor behind the serving table and make wild passionate love to him in front of everybody in the room. Instead, I said in a halting voice,

“I made these cupcakes myself, so if you have any gastric distress you know who to blame.”

I could not believe the inane level of my attempt conversation. A man comes along that I really fancy and that triggered my stupidity button. I wondered what else I could say to drive this interesting man away. I was surprised to see him linger at my table.

“You must be Alice’s teacher. My name is Matt. Alice is my daughter. Ever since my ex-wife moved out of State, I have been raising Alice as a single parent. She told me that you are her favorite teacher and that I should make an effort to be “nice” to you.

I was kind of dumbfounded. All I could think about was the word “nice”. Did that mean he had been commissioned to pound my ass until I begged for mercy or merely to eat my silly cupcakes and tell me how good they tasted?

I hoped, I hoped, I hoped it was the former and that he would get started on it this very evening.

I smiled and smiled and listened to him talking and all I could think was really pertinent thoughts like; how long was his cock? Did he like doing it doggy style? Would he expect me to swallow his cum after a blow job? You know the really important facts.

He left before I could throw myself at him and beg him to strip me of my unwanted virginity.

The next evening, he came into the auditorium when the band was playing a very slow number. Unusual as most of the music was loud and with a rocking beat. Matt asked me to dance. It was on the tip of my tongue to tell him I couldn’t because I was on chaperone duty but a little voice inside me told me to shut up and get out on the dance floor.

Our bodies came together and I could feel every hard muscle in his chest, his flat tummy and his muscular legs. When I felt his cock rise hard between my legs, I just laid my head on his shoulder and let him grind me into a mass of quivering nerve endings. He must have figured out how aroused I was because I swear I could hear my heart pounding and my legs trembled like a silly schoolgirl.

“Alice tells me you have attended to her quite nicely and I feel it is my duty to pay you back for all your kind attentions to her needs.”

When I heard these words, my pussy started leaking big time and I was glad to be wearing the long dance gown to cover my sinful display of wanton behavior. I just looked up into his clear hazel eyes and said,

“I think I would like that very much!”

Matt took me by the hand and led me to the secluded girl’s locker room and locked the door behind him. I was a little nervous, but he spun me around before I could say anything and lifted my ball gown up to my tiny waist. My bottom was fully exposed and I am certain my labia were peeking out from my narrow bikini panties. When his gentle hand pushed my panties to the side, I knew this was the moment of truth. This was the moment when I would lose the cherry hanging around my neck like a restrictive albatross. I wanted that cherry gone so I could enjoy all the fruits of a full sexual voyage of discovery.

He leaned over and kissed me full on the lips thrusting his tongue deep inside my mouth. I was unable to say a single word and that was for the best. It meant I wouldn’t be able to say anything to screw up the most important moment of my life. When the head of his cock touched my pussy lips, I groaned and started to breathe a whole lot harder. He slipped inside with surprisingly little difficulty. I think it was because I was so very wet after the slow dance impaled on his long shaft. I lifted my legs up onto his shoulders to give him a deeper insertion into my pussy. My hymen did not give him any problem. I think it was because of the heated sessions with my very own “James”. The friction of his cock sliding in and out of my vagina quickly took me to the heights of passion and I was literally drooling with my stupid tongue hanging out of my mouth as he slammed my ass against the tiled wall. I wailed my pleasure into the empty room.

Matt picked up the pace and began to grunt like a possessed animal. That signal set off my explosive orgasm and I sprayed my pussy juices all over Matt’s shaft and his balls banging hard against my ass cheeks. When I looked up into his eyes, I saw his face all contorted with the pressure of his spurting creamy cum. He splashed hard into the empty recesses of my no longer virgin pussy.

There was a knock on the door.

Matt unlocked the door after I straightened myself out and we saw Alice waiting outside with a pretend pout on her pretty face.

“You guys are not supposed to do that on school grounds. I am going to tell a chaperone.”

She giggled at the look on our faces.

“Just kidding. What say we all go home and make this a real family affair?”

I looked at Matt and he looked back at me with a smile on his face. I nodded my head in agreement and from that moment forward, I could not really be termed “A tight assed bitch”. In fact, with the proper lubricant, my ass proved quite ready for almost any kind of kinky action Matt or Alice could dream up.