Chapter Ten: The Coming Week
Jack woke up and for the first few moments he'd forgotten, then the events of the night before flooded back into his memory. His cock was already half swollen and now it became a fully fledged erection as he remembered his part in Tamara's role play the previous night. He propped himself up on his elbows and surveyed the debris of their night of kinky passion.
A very short black miniskirt and a four strap black suspender belt were hanging over the back of a chair. On the floor nearby was a pair of black stockings and a pair of size eleven black high heeled shoes. Still around his right ankle was a pair of lacy black panties. Underneath the suspenders and stockings on the chair was Tamara's spectacular red dress. Her stockings, stilettos and six strap suspender belt were also strewn on the floor.
Jack lay back down on the bed and grasped his erect cock. Images of the previous night revolved in his head as he started to play with himself. Tamara fondling his buttocks through the mini skirt, feeling for his suspender straps, cupping his balls in his lacy panties and ogling him at every opportunity whilst he served her a three course meal.
Tamara looking glorious in her red dress, pinning him against the wall and pulling up his skirt so that she could grasp his cock. Calling him Jackie and telling him what a naughty girl he was, what a dirty little tease he was. Calling him her waitress and pushing him onto his back on the sofa so that she could fuck her/him. Then taking him upstairs and binding his hands behind his back for one last spectacular hard fucking whilst repeatedly moaning 'Oh Jackie, you dirty fucking slut' into his ear as she came.
These deviant memories had Jack approaching an orgasm fast and he shot his come onto his abdomen and groaned quietly.
"Did you enjoy that Jackie?"
Came Tamara's teasing voice from the other side of the bed. Jack had thought that she was asleep.
"Don't forget what you agreed last night before we went to sleep."
Jack had promised to dress as a woman and have sex with Tamara at least four times a year. He pretended it was for her benefit but the thought turned him on immensely.
"Don't worry, I remember."
"What would you like to be next time? I fancy you as an air hostess, or maybe a nurse."
Tamara drifted off to sleep again still fantasising about how to dress Jack up. Jack got up, wiped his come off his abdomen and smiled at himself in the mirror. Life was good, he loved Tamara to distraction and between her and Sheryl, he had the sex life he could only have dreamed of a few years ago. He realised that he'd never pass for a woman, but there was something highly erotic about wearing a miniskirt, stockings, suspenders, lace panties and heels while he fucked Tamara in her short skirt, stockings, suspenders, skimpy panties and stilettos.
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Parents' evening on a Monday in mid May 1999, Tamara was dressed in her mid blue skirt suit with black four in inch high heels. She looked smart, businesslike and subtly understated. She drew admiring glances from fathers and mothers alike as she sat showing just enough thigh to be considered mildly provocative, rather than deliberately seductive.
The last parent to sit at Tamara's table was the mother of a sixth former.
"Ms Fox, can we have a word about Jessica please?" said the woman in a soft Irish lilt that warmed Tamara's pussy.
"I'm sorry Mrs Hodges, she's legally an adult now and she didn't give her permission for us to discuss her progress. Off the record, you have no need to worry, she's doing well."
"I'm pleased Jessica is doing well, but can we discuss the crush that she has on you please?"
Tamara knew exactly what Mrs Hodges was referring to but didn't want to admit it.
"Oh! She's very attentive and willing to please but why do you think she has a crush on me?"
"Because I found a message to her friend on her phone saying how she felt in awe of you and how she turned to jelly recently when you wore a black skirt suit, very high heels and had your hair slicked back."
"Oh goodness! I had no idea, I did wear a black skirt suit a couple of weeks ago and my hair was arranged differently because I had a lunchtime business appointment. But I would have described it as a businesslike look. As an assistant head I have to look the part and dress appropriately."
Tamara was aware that she was talking too much in an attempt to justify herself in the face of charges that had not been laid against her.
"Look, I know she's eighteen and is considered to be an adult, but I'm concerned that her head has been turned by an attractive and very seductive older woman, and I'd like your assurance that you will not take advantage of her in any way."
Tamara was thrown off balance for a second or two, she wondered if she'd misheard what Jessica's mother had just said, "attractive and very seductive, take advantage." Could she really have just said that? She regained her composure.
"Mrs Hodges, you can rest assured that I have every concern for the safeguarding of your daughter. A crush on a teacher is quite common, but it usually passes fairly quickly. Like I said, she's a nice, polite girl and she's doing well academically. I really shouldn't be discussing her with you without her permission."
Jessica's mother gave Tamara a lingering, perceptive look.
"Perhaps we could discuss this in a less formal setting, I'd hate you to get the wrong impression, I can see why my daughter is so infatuated, could we perhaps meet for coffee somewhere and continue this discussion?"
A slightly flustered Tamara was trying hard to read the signals, if indeed there were any to be read. She looked closely at the woman opposite, she was in her mid forties, with red hair, a handsome face, deeply attractive green eyes, and a very firm well proportioned figure. She also was wearing a skirt suit, pale grey with black high heels, Tamara imagined that she was probably a senior manager in large business somewhere in the city. She looked so unlike her 'mousy' daughter that Tamara wondered if the girl had been adopted.
"Er, yes Mrs Hodges, perhaps we could, as long as we both... erm... understand what we... erm..."
"Relax Tamara, yes I know your first name, it was written all over a notebook that Jessica was using. Please call me Orla, and I understand your professional caution, but I didn't really think for one second that you had any designs on my daughter. Look, I'll just say it out loud, I find you very desirable and attractive, can we meet up for sex?"
Tamara was taken aback but the approach worked, she was flattered and she felt a rush of arousal.
"I don't think I've ever been propositioned quite as directly as that Mrs Ho... Orla."
"Well?"
In the short pause before Tamara answered, the growing chemistry between the two women was palpable.
"The answer is yes. Do you have a mobile?"
"Yes."
"Give me your number and I'll text you tomorrow."
Orla opened her classy 'Radley' handbag and took out her phone, found the number and gave it to Tamara.
Tamara's eyes followed Orla's perfect buttocks, perfectly accentuated by her short tight pencil skirt, and short fitted jacket, as she strode confidently out of the school hall on her five inch heels. With a tingle in her pussy and feeling that she'd just been swept away by Orla's sexual energy, Tamara packed her briefcase and made her way to her car, it was past ten o'clock and almost everyone else had left.
Tamara's car was on its own in a dimly lit area. She was tired but very aroused by her encounter with Orla, so she took her bullet vibrator from her handbag and slipped it under the hem of her skirt. She imagined Orla's large green eyes looking up at her from between her legs. It took several minutes for her to reach orgasm, but it was well worth waiting for. She grasped the steering wheel tightly with her left hand and raised her pelvis to greet the waves of pleasure that radiated from her pussy.
The next morning at break, Tamara texted Orla.
"Hi Orla, just checking I've got the right number?"
"Hi Tamara, yes you have, do you still want to meet?"
"Definitely, how about that pub on the bypass near Linley Woods tomorrow at 6?"
"Ideal, see you then, wear your black suit."
"Okay, wear stockings for easy access."
"Will holdups do? That's all I ever wear."
"Perfect, holdups are stockings. Can't wait xx"
"Me neither xx"
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Later that night in bed, Tamara cuddled up to Jack and reached for his flaccid penis.
"Jack, guess what? I got propositioned by a parent last night and we're going to fuck. I'm meeting her tomorrow after work. Do you want to know what she looks like and what I'm going to do with her?"
"The answer's in your hand love," said Jack as his cock swelled rapidly until it was rock hard.
Tamara put her mouth to Jack's ear and murmured her description of Orla and what they would do to each other. Jack was soon at the mercy of her expert touch, he lay on his back while she masturbated him to the rhythms of her dirty fantasy and he shot his come over his chest.
Once she had milked him to her satisfaction, Tamara got on top and made use of his still hard cock. She smeared his spunk over him and put her fingers in his mouth to lick them clean then coated her fingers again and seductively licked the residue from them. She closed her eyes and imagined Orla, lying beneath her, connected to her by a double ended dildo, as she rode Jack's cock until she came.
Wednesday morning, as usual, Jack had left for work before seeing Tamara fully dressed. She was in her lingerie when he departed the bedroom and that was enough to give him an erection all the way to his workplace, forty five minutes away. Tamara finished adjusting the last of her six suspender straps, her red nail varnish looking very seductive against the welt of her barely black stockings.
She would be wearing a crisp formal white shirt, so she had opted for a white bra, panties and suspender belt. She looked amazing standing in front of the full length mirror and stepping into her tight black suit skirt. Then she stepped into her four inch high black heels and put her stilettos in a bag for later. Her perfectly ironed crisp fitted white shirt contrasted well with her black skirt. Finally, she put on her suit jacket and took in her own image as it stared back at her.
She felt magnificently sexy in contrasting black and white, offset by scarlet lips and nails, and a string of dark red beads at her throat. She tucked a cylinder of hair mousse into her handbag so that, after work, she could flatten her hair to complete the severe but sexy look that Orla's daughter so admired.
