The chaperone

Written by , on 2019-05-13, genre cheating

Diana king was a thin, curvy built woman
5'5" tall 105 pounds with a very athletic 34DD-23-34 figure. Green eyes and wavy raven black hair that fell to her tight, sexy bubble butt in light curls. At 34 years old she knew she had all the answers.
Diana was as smart as she was beautiful.
She was a virgin on her wedding night at 22 years old.
Sure she had dated some. But, refused to let men interfere with her studies. Her husband was only man she had ever been with and did not care about any other.
Thought they where all below her husband.
Partly out of loyalty and partly for fear of being caught.
She seen how they where as young men in her english class acted that she taught. They all had one thing on there minds and most young men treated her differently then all the rest of the teachers anyway.

All but Conrad McDonald.

Conrad was different then most of the students.
He treated everone with the same respect and very seldom ever gave Diana even a side glance.

Which in truth deep down really got to 34 year old teacher.
"How could a boy of his stature not even give me a wondering look." Diana huffed to herself several times frustrated.
She had come accustomed to young men learning over her.
What even bothered her more was Conard wasn't rich. His parents did not have money.
While the rest of his class was going off to hire learning Conrad would not be.
At 6 foot tall and 220 very lean sexy pounds Conrad had signed up for the military.

Diana was standing with a couple of the other teachers as they watched the students dance.

"Care for a dance." One young man asked Mrs. Smith.
"Oh, I don't know." The older lady laughed blushing thinking about it. Know it was perfectly acceptable at the senior prom for the teachers to dance with the students.
"Oh, okay." She finally agreed after some serious puppy dog eyes.

Before long Diana king stood alone as the students and some of the teachers danced and had a ball.

Which didn't surprise Diana. Only once she was asked to dance and that was 10 years earlier on her first year teaching and being her first chaperone job.
Diana turned the young man down flatly then went on to belittle him in front of the other students and teachers that stood close by. Feeling proud of herself that night, it wasn't till a few years later she realized the magnitude of her mistake.

Diana stood alone off to the side of the room mainly trying to stay hidden.

"Can you not dance?" Diana heard in a deep sexy voice next to her almost making for scream in fright.
Gathering her wits quickly. Diana looked up into Conrad's soft, warm brown eyes.
"I didn't mean to scare you ma'am." Conrad smiled one of his deep true smiles.
"Yes, I can dance." Diana said in her always stone cold look.
"You know. You'd be a hole lot prettier and more approachable if you smiled." Conrad grinned that sexy grin of his walking off.

"Fuck you." Diana sneered under her breath.

"You know Diana that young man didn't deserve that." The much older Mrs. Clayton said lightly with a soft smile.

"He's just like the just all young men. Thinking about how he could get in my pants." Diana snarled.

"Well maybe that us just what you need is for one if these young stud to take you back to your room and screw you like a slut. Because obviously your husband isn't doing the job right." Mrs. Clayton said softly with her same welcoming soft smile.

"What?" Diana gasped.

"You heard me young lady and if there was a young man here that could give you that type of fucking he just walked off." Mrs. Clayton grinned.

Diana didn't know what to say or think. The older woman had hit the nail on the head.
Sure the sex between her and her husband was mediocre at best when they had it once a month or every other month. But, still she was married.

Diana never would admit it. But, young Conrad stirred something inside her.
She would dream of him late at night when her husband was asleep as she worked herself to a withering mess on the living couch.

"Think about it." Mrs. Clayton smiled. "I know your one of only three soundproof rooms on the top floor." The older smiled before walking off.

Diana stood there in awe of the conversation that just took place.
Deep down she knew mrs.Mrs. Clayton was right.
As her mind wondered as small almost unnoticable and involenteertly orgasm ran up her spine.

When Diana looked around the room after composing herself she Mrs. Clayton smiling at her tapping her watch.
Diana took a glance at hers. 9:30 on the dot.
Then her bald little love hole spasmed again causing her to shiver a bit.
When Diana looked mrs.Mrs. Clayton was still smiling at her with a knowing grin.

Slowly Diana started to make her way around the ballroom. Till she was standing next to Conrad.

"My room thirty minutes." Diana smiled lightly not looking up at him as she slid a key card into his left pocket.

Conrad looked at his watch and just grinned as nothing was going on and watched Diana as she slowly escaped the ballroom.

Diana stood in the middle of the floor in her suite clad in the most sexy red lace bra and panties that she owned.

"My, my." Conrad grinned as he walked across the floor eyeing the sexy teacher.

"I'm yours for the night." Diana moaned in lust and need as Conrad pulled her tight to him and kissed her neck as she wrapped her legs around his strong body.

Diana laid flat on here belly spred eagle grasping the bed sheets as her lady juices flowed freely from her need flower as Conrad licked her forbidden hole.

No one had ever touched her there. Certainly not her husband who thought it was vulgar to even get close to that area.

"Mmmmm. Yum." Conrad moaned in truth as Diana laid on her back holding his head as he devoured her tasty sex.

Diana couldn't believe how good and free it felt. The last time anyone had stuck there tongue down there was her wedding night.

Diana dilengatly sucked Conrad's large man hood.

She couldn't believe his size. Soft he was bigger then her husband and hard. "Oh my fucking god." Was her words.

Diana couldn't believe how nasty she was being.
She sucked Conrad off every chance she got.

Something her husband would never allow her to do. And here she was willingly and diligently sucking a dick.


When Conrad emptied his large nuts into her mouth she swallowed every drop then licked her hands and chin clean like a hungry pup at the feed bowl.

Diana was on top of Conrad riding him hard when she asked him if he wanted to fuck her ass.

"Oh Jesus fuck!" Diana moaned out as Conrad popped past her rubbery ring.
And her eyes rolled back in her head, as her body quivered and shook and she started talking in tongues when she orgasmed.
"Fu-c, go-d, da-mned, I, cum, ming, sh---ittttt."
"Fuck, fuck, fuck!" Conrad grunted out as she drove herself down on his entire length in powerful thrust.

It was after 5 in the morning when they both tired to the point of exhaustion curled up in each others arm in orgasmal bliss.

Diana was the first to awake.
At first she thought about sneaking out with waking Conrad till her stirred and the sheet fell off him and revealed his semi hard man meat.
Thirty minutes later Diana was swallowing another large load of his sweet man juices.
For almost the next hour they played out senses from the previous night and made some new ones.

Conrad banged her hard again in the shower bring her to several large orgasms.

Bent over the couch in the front room Conrad licked her to orgasm again and took her in her forbidden hole once more.


"Good morning Mrs. King." Mrs. Clayton smiled as Diana enter the lobby.
"Good morning Mrs. Clayton." Diana chirped back with a big grin.
"I see you slept well last night." Mrs. Clayton said with a knowing grin.
"It was a wonderful night and just as good morning." Diana smiled.
"Good for you." The older woman grinned.

"Conrad!" Mrs. Clayton smiled at the sexy young stud.
"Aunt Meg. Who are you this morning." Conrad grinned.
"Not as good as you." The older woman smiled. "Hope you have enough left for me." Mrs. Clayton smiled kissing her nephew.
"Always"

This story from has been read 6 2 7 8 times

Report abuse in this erotic story

Reader comments on the erotic story

cookies policy For your best experience the site uses cookies. By using this website you consent the use of cookies in accordance with the terms of this policy.