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Remembering Mrs. Bolton

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Young man begins training from an older woman.
1.7k words
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All during high school, I had managed to do it, and it being the last day of my senior year, I decided that I deserved one more time.

Checking up and down the hallway and confirming that nobody was near, I leaned in and cracked the door to the girl's locker room open just enough for a quick peek. Most of the time my peeks had been so brief that I rarely saw more than girls in their panties and bras and occasionally some wrapped in towels, but I always had high hopes of the one reason I peeked - to catch a glimpse of a naked Brenda Baker, the hottest cheerleader in school.

I was about to give up and back away from the door when Brenda appeared, wrapped in a towel, hair soaked from a shower. Her back was to me as she pulled the towel free. I grabbed my crotch involuntarily as I stared at her perfect ass.

I was so mesmerized that I nearly yelped as I felt a finger tap me on the shoulder.

Shit! I turned slowly and saw Mrs. Bolton, the school head nurse staring at me.

"Did you lose something in there, Mr. Norman?" she asked firmly.

"No, ma'am," I answered weakly.

"Then what were you looking for, and don't bullshit me or there will be consequences?"

"I was hoping to see one of the girls naked; I have a crush on her," I answered honestly.

"Haven't you already seen naked girls in magazines?"

"Yes, Ma'am, but not a real girl like Brenda."

"Perhaps her parents would like to know how you feel about their daughter," she said in a threatening tone.

"NO, no, ma'am, Brenda doesn't even know that I like her, it would be embarrassing."

"I think you need to visit the nurses' office after school so we can discuss how to best handle this situation."

"But I'll miss the bus," I contested.

"I'll give you a ride home after our little chat, now get back to class and don't be late this afternoon."

Mrs. Bolton was a 52 year old widow who had been a nurse at the high school for years. She was well liked by her peers and well respected by the students. She was average in height with shoulder length brown hair. Her figure was attractive for a woman her age, just slightly too heavy to be called slender.

I was ten minutes late when I arrived at the nurse's office and Mrs. Bolton was waiting for me. I sat in one of the chairs opposite her desk as she walked behind me and closed the door. She stood in front of me, leaning on her desk with her arms crossed over her chest.

It was then that I noticed how short her skirt was. Standing inches in front of me, her legs were parted slightly and the hem of her skirt was midway between her knee and her thigh, and as she leaned back, her thighs were visible.

There was deathly silence in the room as I realized I was staring and then that she saw me staring, and at what I was staring. I shifted uncomfortably in my chair.

"Is there something wrong, Mr. Norman?"

"Uh, no, ma'am," I said.

She looked down and gasped; "Oh, my God, do you have an ERECTION?"

"I'm sorry, Mrs. Bolton," I answered as I crossed my legs.

"It's nothing to be embarrassed about," she said calmly, "but how are you so easily stimulated?"

"It's your legs, ma'am; seeing a girl's legs up high like that turns me on; I can't help it."

"Well, I'm pleased that you like my legs and very pleased that they excite you."

"You are, I mean, it's okay that I like looking at them?"

"Of course it is; it's a compliment to a woman my age." She was quiet for a moment and I took advantage of the chance to stare closer. Did her hem just creep higher?

"Would you like to touch them?" she asked softly.

I was so excited I just reached out and rested the palm of one hand on the inside of her thigh. My dick strained against my pants. As I was running my hand up and down her thigh, she asked, "What do you do when you're this excited, Will?"

"Usually, I, you know, as soon as I have the chance."

"You mean you masturbate?"

"Yes, ma'am."

"Would you masturbate while thinking about my legs?"

"Um, yes, ma'am as soon as i get home."

"That's very exciting and another compliment to me. Pull it out, Will."

"Excuse me?"

"Your dick. Pull it out; I want to see how hard it will get."

"I don't think so, it's pretty embarrassing as it is."

"Nonsense. I've accidentally aroused you and you shouldn't be embarrassed; It's only natural to relieve yourself when you get this way."

Slowly I stood up, unbuckled my belt, unzipped my pants and pushed them and my underwear down to my knees. My erection pointed straight at her.

My reaction surprised her. "I expected to see it but not quite like this," she said with a grin.

"This is the way I, um, relieve myself," I answered.

"Very well, but I want to try something that I've never done with a young boy before; would you mind?"

"No, ma'am, anything you want," I answered, thinking I might get fucked for the first time in my life.

"I want you to wrap your fist around the base but don't stroke it; I want to tease you to see how hard and how big it can get."

"Okay, I guess," I said, doing as she told me.

She opened her blouse and pulled her bra down off her breasts. Her full breasts spilled out, the nipples staring right at me.

"Do you like my tits, Will?"

"Oh, YES, ma'am!"

"Put your hands on them and squeeze them, nice and gentle."

I filled my hands with her breasts and my dick throbbed with joy.

"Would you like to suck on them sometime?" she asked, smiling at me.

"Oh, fuck, yeah," I gushed. "Oh, sorry, ma'am."

"That's okay, I know you're excited. Stroke yourself but very, very slowly."

My hand began to jerk up and down but she stopped me. "No, no, you can't do it the way I want; let ME do it for you," she said. Her delicate fingers wrapped around the tip of my dick and she just twisted it slowly like a fleshy knob.

"I know boys think of jerking off on a girl's tits. Would you like to come on my tits, Will?"

"Oh, yeah, please, Mrs. Bolton, can I?"

"No, dear, remember it's "May I?""

"May I please come on your tits, Mrs. Bolton, please?" I begged.

"Of course not," she said, lightly squeezing the tip of my dick.

"Lift up and hold the hem of my skirt so you can see my panties."

I nearly lost it when I saw the soaked crotch of her white cotton panties.

"That's my vagina, right there, Will. Have you ever seen a real vagina?"

I moaned like a puppy. "No, ma'am, can I, I mean, MAY I see your vagina?"

"Oh, no, that would be inappropriate," she said, squeezing her fist around the tip of my erection. The tip was already slick with precum and it was getting wetter.

"Reach down with one hand and rub the crotch with your fingers, Will."

Nothing in life could have made me harder, and my heart beat in my chest as I slid my hand down between her legs and rubbed my fingers across the wet fabric. I moaned with excitement.

Her fist rubbed back and forth over just the tip of my dick and I felt that I might cover her hand with my sperm any minute. The fingernails on her free hand lightly scratched the underside of my scrotum.

"Smell and taste your fingers, Will, it's just like smelling or tasting my vagina."

My dick throbbed uncontrollably in her fist as I smelled my finger tips and then sucked on my fingers. I almost whined with excitement and need.

"Close your eyes and imagine this, Will, I'm going to put my vagina right on your tongue; can you taste it, can you taste my vagina, Will?"

I nearly cried with frustration and excitement. Why was she torturing me like this?

"Cum for me, Will," she said, jerking the tip of my dick, "CUM NOW!"

I am certain anybody outside the building heard me yell as I came, shooting my load, spurt after spurt as she stroked my dick.

When I was spent, I opened my eyes and collapsed into the chair behind me. Mrs. Bolton stooped in front of me, displaying a small puddle of my cum in her cupped hand.

"Very impressive, Mr. Norman," she said.

I was panting and unsure of what to do or say. "That was amazing, Mrs. Bolton; thank you for relieving me," was all I could muster.

"You're welcome and thank you for letting me try that experiment with you. I've always wanted to see just how excited I could make a young man get."

As I was rearranging my pants, she went behind her desk and sat down. She looked at me pensively for a moment. "Ordinarily at this point a man would reciprocate in some way, but I doubt you have the right experience to do that."

"No, ma'am, I'm still a virgin except for what you just did and my own masturbation."

"There is so much a woman my age can teach a young man like you, Mr. Norman. If you would like to visit me at home we could spend time in my study to discuss and experiment with things that will change your life."

"I would love that, Mrs. Bolton. May I call you by your first name?"

"No, you may not. I am Mrs. Bolton to you, or if you prefer, ma'am will do."

"Yes, ma'am."

"Good boy. And if you keep our little experiment here confidential, you'll experience everything sexual you ever dreamed of and more."

"I'm looking forward to it, Mrs. Bolton."

"Excellent. Shall we we say this Saturday afternoon for your next lesson?"

"Yes, ma'am."

"Oh, and Mr. Norman, do NOT masturbate before then."

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11 Comments
shadysweetshadysweet15 days ago

I’m not really super into the mature genre but I really enjoyed reading this! Thank you for reading some of my stories as well and leaving your thoughts, I appreciate it very much. (Especially Taming a Brat.) It’s been almost a year but I am in the process of editing/submitting chapter 12 and it’ll be a nice long one. :) Now on to chapter two of Remembering Mrs. Bolton! :)

AnonymousAnonymous24 days ago

HOPE SHE TEACHES HIM ABOUT ANAL!!

Freesoul50Freesoul5026 days ago

I found the story very interesting and I am looking forward to reading how Mrs. Bolton educates Norman on how to pleasure a woman. Thank you for writing this interesting story.

jjfronjjfron26 days ago

Love it...sequel PLEASE!

AnonymousAnonymous27 days ago

Chapter two needed! NOW!

HotJimHotJim27 days ago

This is an excellent coming of age tale. It's a perfect stand-alone piece. Follow-up would also be welcome.

AnonymousAnonymous27 days ago

Love it. More please!

timothy522timothy52228 days ago

WOW, Please continue!

AnonymousAnonymous28 days ago

Waiting for a 2nd chapter when he fills her mature pussy with his young seed.

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