tagTranssexuals & CrossdressersHis Son's Teacher Ch. 01

His Son's Teacher Ch. 01



Dave Monet hated meeting his son's teachers for the first time. It was always awkward for one reason or another. Sometimes the teacher would be attractive and he could not help but stare, which he thought was disrespectful to his wife, now his ex-wife. Most of the time what he hated most of all was the not knowing what she would say about his son's behavior and/or academics. His son was the typical teenager, at 17 he cared more about cars, sports and girls than about academics and his future.

But tonight was especially awkward. Eric had talked a lot about Ms. Stepford, the new social studies teacher. He had described her as a 'MILF', not too old but old enough that teenage boys were shocked they were attracted to her. Dave felt excited at the prospect of having a pretense to talk to an attractive woman. The numbness of his divorce was beginning to wear off, and he found himself missing the warmth of a woman.

* * *

Tiffany breathed a sigh of relief as Mr. Atkins' appointment ended and he got up and left. The other teachers said that tonight would be easy, that by high school most parents had become less involved in their kid's education seeing it now as their kid's responsibility and thus less inclined to come in and blame her. However, tonight, all of her parents were showing up at their regularly scheduled time. Correction; all of her kid's fathers were showing up and mostly the ones from kids whose parents were divorced.

It was the same story when they came in the door. She would stand and cross the room to greet them. They would look her over and she would let them, secretly she enjoyed all the male attention. It made her feel more feminine. However, they would inevitably lose interest. She should not have worn heels. Sure, she loved her new black platform pumps. However, it only added about six inches to her already tall 6'1". Therefore, as she waited for her next appointment, she slipped out of her shoes and let her feet take a break from the heels.

There was a knock at the door, she looked up and saw a tall shadow through the narrow window slit of her door. Awkwardly she fumbled for her heels but it was too late, Mr. Monet was early and had entered her room.

* * *

Dave was not disappointed. The woman sitting at her desk was a pretty brunette wearing a black dress. It was made of a stretch fabric which combined with a split neckline gave a subtle hint of her curves. A princess waist only accentuated her hourglass figure. He was happy when she stood up; most teachers sat at their desk and made you cross the room to them. She had been playing footsy with something under her desk, and judging by her bare feet it had been her shoes and they had won.

This gave him a chance to appreciate her legs. They were shapely and athletic and shimmered in expensive black nylons. He, correctly, imagined that they were thigh highs and that their lacey tops were attached to a garter belt. He found that he liked the fact that she was barefoot and that she was coming to him, and that he had stopped just inside the doorway forcing her to cross the length of her room. And she did, with a smile. She offered a hand and he shook it, her skin was soft, yet her grip was a little more strong and sure than he was used to in a woman. He found that her confidence was a strong balance to what he, again correctly, perceived as a natural submissiveness.

* * *

Tiffany blushed a little when Mr. Monet shook her hand, it was strong and firm as a man's shake should be. She looked him in the eyes and the strength she saw there made her look away. She glanced back up at him and smiled because he smirking, a self-satisfied smirk. Then she realized she was looking up at him. He was a good 6'5" and she was glad fate picked that moment for her brand new heel to break.

"Pleased to meet you, Mr. Monet." She said showing him to his seat in front of her desk.

"Please call me Dave." She had a strict rule about calling her kid's parents by their first name. She thought that it was unprofessional.

"Alright, Dave." The name felt good on her lips. "I was hoping you'd come. Eric is one of my favorite students."

"He is?" Dave was a little shocked. Eric being a mediocre student meant either he was a pain in the teacher's ass, or they did not really have anything to say about him.

Tiffany giggled. "No really. He seems to really enjoy American history and he's always paying attention and engaged in class."

"He is?" Again, Dave was a little shocked.

Again, Tiffany giggled. She opened her desk drawer and leaned over to get Eric's folder from her locked file drawer. As she moved Dave caught a whiff of her perfume, it was Beautiful and it reminded him of an old girlfriend who wore that perfume in high school. Tiffany sat up straight and opened the folder. "Yes. This is his last test."

He looked at the paper in disbelief. "104%?"

"Yes, he missed one but got the bonus. He's getting straight A's in my class."

* * *

It had been the best thirty-minute parent teacher conference she had had tonight. Mr. Monet had been engaging and genuinely caring about his son. Then there was the spark. She felt a definite attraction and she thought that maybe it was mutual. Too bad her secret would not let her act on the attraction.

* * *

Dave smiled as he left her room. There was something about her that was different. She had a warmth and empathy that was different from other women he knew. He had noticed the coffee cup on her desk, her lips had left an imprint in red lipstick on the rim of the cup. It was from Kallisti's Coffee, a small coffee shop in the college district and the interns at his firm would bring coffee in from there. He thought that he should maybe start going there himself.

* * *

Tiffany got home and went straight to her bedroom. She was so horny and had to take care of business. She just could not get Dave...Mr. Monet...out of her head. She slipped out her dress and just let it drop to the floor. She was wearing a black and panty set and gartered thigh highs. She flopped on her bed, rolled on her back, and slid her hands into her panties. Her cock had become untucked on the drive home and now her 'clitty' was fully erect and she slowly started stroking herself. She closed her eyes and started to moan. She began rubbing her breast, the hormones she had taken had worked better than she and her doctor expected. She now had a decent set of C-cup breasts. Her nipples were almost as erect as her 'clitty'.

Dave was all that was on her mind as she touched herself. She rolled over on all fours, reached into her nightstand, and pulled out a purple dildo from her nightstand. She lubed the toy and buried her face in her pillows as she jerked off and slowly slid the anal training toy into her ass. She thought about it being Dave's cock inside her, making her his girl. In minutes, she was cumming shooting her honey across the mattress. Slowly she took the toy out of her ass and looked at the mess she had made. It was cloudy and soaking into her sheets. She started slurping it up, another training regimen she had started when she moved to Portland. Eventually she would work up the courage to accept a man's invitation and get her V-card punched, and she wanted to be ready when that happened.

Satisfied that she had slurped all she could from the sheets she swallowed and stripped the bed and put clean sheets on before hopping in the shower.


This would be the last time Dave would come to Kallisti's Coffee. The coffee was not as good as his interns raved, and the food was all right but nothing great. The only reason he had come here was it was on the way from dropping Eric off at his mother's house and the new apartment Dave had moved into across town. Moreover, he was hoping to see Ms. Stepford. He looked over and reading a book on the Korean War was Ms. Stepford. She was wearing a white, cowl necked sweater dress. After all, it was February in Portland. She was drinking what looked like cappuccino from a wide coffee mug, taking an occasional sip and not looking up from her book.

As he waited for his cup of coffee, he admired the woman that he had come here to see. Once again, he could not take his eyes off her legs. They were clad in opaque, black leggings and she was wearing black suede, corset-tie high-heeled boots. He got his drink and screwed-up his courage. He crossed the coffee shop towards his target.

Tiffany looked up as a shadow darkened her page, and was more than pleasantly surprised to see Mr. Monet. She smiled broadly. "Hello, Mr. Monet." She said standing and offering her hand. She was shocked when he took her hand and pressed it to his lips.

"I said call me Dave." He said with a wolfish grin.

"Okay...Dave." Tiffany blushed, finding herself at once at ease with him and off-balance. "Would...would you care to join me?"

"I'd love to." He said taking the seat across from her.

* * *

They stayed at the coffee shop for about two hours before getting bored with the college environment. Dave suggested a bar he knew with an Irish pub motif and nice dark corners where they got lost in each other's eyes and stories. At some point, they stopped talking and started kissing. Dave was a slow kisser, drawing her close to him as their tongues danced. Soon his hands were sliding up her sides and then to her breasts. It felt so good to feel a man's hands on her breasts. However, once his hands started drifting south, she gently guided them back to her chest.

She had dreamt of this moment since before she moved to Portland, since before she began the transformation. It was finally here, but as much as she was excited and living in the moment, she was terrified. Not only was she in the arms of a man for the first time, but it was the man she was crushing on. However, what terrified her was what would happen if he wanted to take it to the next level. Her secret would be out, and if he wanted to make an issue of it, she could lose her job.

The obnoxious sound of a bell and the blinding light of the house lights caused them to break their kiss. She bit her lower lip and watched him as the waitress came over and handed him the check. She reached for his purse. "Hey, pretty lady, I've got this." He said and pulled out a $100 bill and gave it to the girl. "Keep the change." He slid out of the corner booth and offered her his hand. "My place?" He asked.

"Sure." She knew she should not accept the offer, that she should not go back to his place. However, she could not control herself; she wanted this more than anything so she let him lead her out into the cold night and his Lexus. He opened the door for and she slid into the passenger seat.

For his part, Dave was beaming as he shut the door and crossed to his side. He opened the door, slid in, and looked at his gorgeous date. She was checking her texts when he slid into the driver's seat. "I'm sorry, Dave." She said when he shut the door. He looked at her, his heart sinking. "Could...could you take me back to my car? My bff just texted me, some crisis with her boyfriend."

"Oh..." the disappointment in his voice was thick. "Okay." He said as he pulled away from the curb.

"I'm sorry." She said, sliding a hand on his knee. "I want to make it up to you." She leaned over and nibbled on his ear as her hand slowly made its way up his thigh before lightly squeezing his crotch.

"Mmmmm...." He moaned as she kissed and rubbed him. He was shocked when she fumbled his belt loose before unbuttoning his pants and unzipping them, freeing his cock.

"Wow!" Was all she said as she looked down at the large cock in her hands. It was about six inches long even though it was still flaccid. Her warm hands were making it stiffen as she held it.

"Wow, yourself." He said breathlessly. "I wasn't expecting a hand job!"

Tiffany giggled. "Who said anything about a hand job?" She said as she leaned over into his lap and began licking his head. Dave swerved in surprise as her warm, wet tongue touch his sensitive head. She giggled and then started licking the bottom of his shaft and massaging it with her lips. Cupping his balls, she started caressing them and tickling them with her fingernails. She smiled as he grew as she pleasured him. A drop of precum glistened in the streetlights as they drove down the street.

"Ohhhh..." He moaned as she slid the cock into her mouth and started taking it deep. "Do...do you mind," he asked breathlessly, "we're close to my firm...can...can I pull into the garage?"

She pulled off his cock just long enough to reply, "Yes". Her breath was warm on his head as she said the word. She had always been curious what it would be like, what it would taste like. The precum was a little salty compared to hers, but the cock did not really taste like anything. What she loved, and yes, she loved it, was the way his cock felt in her mouth. It was warm, alive and every twitch & moan she knew he was enjoying her effort. From this angle, she could not see where they were. All she knew was they were slowing down and then turned into what could have been a parking garage with how it went from dark to light.

The car rolled to a stop and Dave fumbled to slide the shifter to park. He reclined his seat and rested his hand on her head. Despite his disappointment at her needing to go home, this date had gone well for him. He had had drinks with a lady who understood him, and was incredibly nonjudgmental. Sure, she liked the Rams over the Seahawks, but she seemed to genuinely enjoy football. And that was something. Now she was sucking his cock in his firm's parking garage.

Dave's hands in her hair felt exquisite as he controlled the speed as she sucked him. His fingers intertwined in her hair, his grip was strong and tugged at her roots. Each time that he pushed down, he went in a little deeper. She was making little gurgling noises as the cockhead pushed past her gag reflex. She relaxed her throat and let the cock slide back into her throat. She began to dry heave, her throat spasming along his shaft. He held her there for a moment and then released her. She came off him, a thick rope of slobber linking her lips to his head. "Fuck, Tiff, I'm going to cum!" He shouted, and she immediately wrapped her lips around his glans. He twitched releasing strand after strand of hot cum into her mouth.

About half of her reward shot straight down the back of her throat without her tasting it. The other half splattered her tongue and cheeks as she tasted his cum for the first time. It was salty like she was used, but also a little sweeter than she expected. It was also quite a bit thicker than her's. Slowly she swallowed. Lovingly, she kissed the tip of his penis and reverently slid it back in his underwear and zipped, buttoned and buckled his pants. She looked at herself in the small vanity minor of her visor. A small dab had tried to escape from the corner of her mouth, with a delicate pinky she pushed it into her mouth, making a show of it. "Don't want to waste a drop." She said, turning to him she could see the passion in his eyes.

"That was amazing Tiff!" He said, leaning in to kiss and nibble on her neck. She moaned and rolled her head to one side, lost in the magic of the moment. "My turn." He said and quicker than she could react to stop him, his hand darted to her crotch. Her clitty had come untucked and was now fully erect. His hand squeezed and stroked it, but clumsily. He was no longer kissing her, but looking at her with a quizzical expression. She could not make out what he was thinking. "You...you have a cock!?!"

Tiffany began to cry.

(To be continued)

Report Story

byGillianCD© 20 comments/ 77667 views/ 68 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartGrannyman, Ffelicity and 66 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous08/14/17

A 6'1" woman

Wearing 6" heels to parent teacher night. The story is too stupid to read past that line.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 20 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: