Timothy Asks pt1

This is a story inspired by the image below.

Today was the day.

Timothy had been planning this for months.  Well, he'd been thinking about it for months....  The actual planning and preparation had come in a rush this morning.  But he had been steeling himself for the conversation throughout his school day.  He sat through Ms. Johnson's class, completely unable to concentrate on the day's lesson.  Fortunately (or, he ruefully thought to himself, unfortunately...), he was a good student...especially in Ms. Johnson's class, so it didn't get him in trouble.

Finally, the last bell rang.  All of the other students, eager to get outside on a beautiful spring day, bolted for the door.  Ms. Johnson remained seated behind her desk, looking down at a few papers she was marking up.  Timothy lingered a bit as he packed his supplies into his school bag.  He took a deep breath and pulled a single sheet of paper from the bag.

"Ms. Johnson?"

"Yes, Timothy?"  Ms. Johnson looked up at him and smiled.  Timothy thought she was the most beautiful woman he had ever seen.  Tall and willowy, but with a clear strength that showed in her control of the class.  She kept her dark blonde hair cut short, which gave her the appearance of a '50s housewife, if an exceptionally attractive one.

Timothy walked towards the teacher's desk, the paper clutched in his hands.  The picture was facing towards him so Ms. Johnson didn't get a look at it before he was able to explain.  He stepped away from his bag so that he had no opportunity to chicken out and stuff it back into the folder where it had been sitting all day.

"Ms. Johnson, there is something I wanted to ask you.  It's a little embarrassing."

Ms. Johnson looked up, a mixture of interest and concern on her face.  Timothy was one of the best behaved students she had ever had.  Even though she didn't like to admit it, even to herself, he was very clearly her favorite student this year.

"Yes, Timothy?  Is something wrong?"

"This is very hard to ask, and I knew I wouldn't be able to get it out....so I drew you a picture.  Would you mind looking at it?"

"Of course, Timothy. Let me see."  She reached out her hand.

Timothy's mind panicked.  This was the point of no return.  He'd set it up deliberately so he'd have no way out that wasn't more embarrassing than the conversation he was about to have.  He handed her the paper.

Ms. Johnson looked at the paper.  She was very confused. On it was a colored pencil drawing.  Timothy was a talented artist, and the figures were clear.  A woman with Ms. Johnson's features was seated on a chair, her right arm upraised. Her face was stern.  Across her lap was a young man, with his pants  down, exposing a pair of white briefs.  His head was slightly turned, but the face was recognizably Timothy's.  There were tears running down his face.  It was very apparent to Ms. Johnson what was happening in the picture.

Ms. Johnson looked up.  "Timothy, this is a very good drawing, but I admit I am kind of confused.  I am thinking back over the year, and I don't think I ever had the need to spank you."

This was sadly true.  Ms Johnson did spank her students on rare occasion, but only when they truly deserved it.  Timothy's birthday was not during the school year, so he had been denied even the playful birthday spanks she gave to students fortunate enough to receive them.

Timothy breathed deeply.  "I know Ms. Johnson.  That's what I wanted to ask you.  I can't get the thought of that drawing out of my head.  I....I was hoping you could give me a spanking before summer vacation started."

Ms. Johnson was taken aback.  "Well Timothy, I have to say that is the most unusual request I have ever had.  Most students try very hard to avoid spankings.  That's why I use them."

Timothy nodded silently.

"I'm going to have to think about this.  I'm not saying no.  In fact, I am probably going to say yes.  But I think we need to get a few things clear first.  Is that OK?"

Timothy nodded again.

"Ok.  First, this obviously needs to stay between us.  When I discipline a student in class, there is a record.  And I don't want your excellent school record being marked up for something that you don't deserve.  Also, I'm sure you can imagine that other people knowing about this would be just as embarrassing for me as for you."

Timothy doubted that, but he nodded his enthusiastic agreement.

"I notice that you are crying in this picture.  That makes me think you aren't asking me for a playful birthday spanking. Is that right?  You want a real one?"

"Yes Ms. Johnson."

"Is there something you feel you need to be punished for?  Something you want to tell me?"

Timothy started listing a number of petty misbehaviors, both in school and at home.  Ms Johnson listened and smiled.  "Well, Timothy, that's quite a list.  But none of those are bad enough for a spanking.  And I think you might just be exaggerating a few of them a bit."

Timothy blushed.  She was right.

"You are a very well behaved student, Timothy.  I don't think you deserve a spanking at all.  Are you sure this is something you want?

"Yes, please Ms. Johnson.  I really need you to do it."

Ms Johnson nodded.  "OK Timothy.  In that case, I need you to understand three things.  I want to make sure I give you what you need, and so I'm going to be very clear about what a 'real spanking' means.  First, I will pull down your pants and spank you on your underwear. Your picture shows that you already know this, but I want to make sure we understand each other."

Timothy had made a few preparations with exactly this in mind.  He nodded again.

"Second, and I know you know this...I spank hard.  You've seen me spank other students.  You know it hurts a lot, right?

"Yes Ms. Johnson.  I think I need it to hurt."

"That brings me to my third point.  If this is a REAL spanking you are talking about, then this is your last chance to change your mind.  A real spanking ends when I think it should end...not when you decide that it hurts too much.  Are you quite sure you want to find out if the reality matches your fantasy here?" She gestured towards the drawing.

"Yes Ms. Johnson.  You can spank me as long and as hard as you think you should."

Ms Johnson sighed and stood up.  "OK Timothy.  I honestly thought I was never going to have to do this to you.  You are so well behaved in class.  But I understand that this is something you think you need." She walked to the classroom door and locked it, then pulled the curtain over the small window.  She walked back, pulled the chair from behind her desk and sat back down.  "Please come stand in front of me."

Timothy stepped around the desk and stood in front of her.  The moment had come.

"Hands on your head."

Timothy immediately complied.  Ms. Johnson's hand went to the button on Timothy's shorts.  She slid them down to his thighs.  Then she stopped.

"Timothy, you are not wearing underwear."

Timothy had no response.

"Did you do this on purpose to get me to spank you on the bare bottom?  You know that's not how I spank."  Her voice was very stern now.

Timothy slowly nodded.

"Well, young man.  That is far, far worse than any of the little crimes you listed for me earlier.  Only the naughtiest boys get spanked on the bare bottom, and it looks like you are about to find out why that is."  Leaving him standing with his pants down, she reached to a drawer on her desk.  She slid it open and retrieved something.  She placed it on the desk.  It was a very ominous looking hairbrush.  Timothy had never seen it, let alone seen it used.  Ms. Johnson had threatened a few other students of its existence, but this was the first confirmation he had of its reality.

"It looks like it will be a day full of firsts for both of us.  I haven't had to use this in a few years. I think you're going to regret this request.  Come stand on my right side.  And I mean now."

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