Tamara In Stockings Ch. 10

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.

********************

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"

********************

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.

She created a quite a stir as she went about her business that day. She was the most lusted after women in the school. There were several other, younger, attractive female members of staff, but they didn't tease pricks and pussies like Tamara.

Jessica looked at her like an infatuated lover, Tamara ignored her and delivered the lesson like the professional that she was, but this just left Jessica yearning for her even more.

Sheryl whispered in Tamara's ear in the staff room during morning break, "My God, I could fuck the tits off you today darling."

Tamara gave her a sultry smile, the bell rang and the corridors bustled with activity. Tamara was in her office for the next period taking care of her sixth form management duties. She couldn't resist texting Sheryl, who she knew would be in a meeting with the Head and several governors and LA advisers.

"Hoping to get my tits fucked off this evening, meeting hot parent for sex, will kiss and tell you all about it at your place tomorrow evening if you like? xxx"

"God yes you sexy bitch, I'll be all ears, and wherever else you'd like to put your tongue!"

"Dirty cow!"

"Who are you seeing tonight?"

"Nice try, You'll have to wait until tomorrow for me to confess all. xxx."

"At least tell me if it's a he or a she."

"No, wait until tomorrow you nosy cow."

"Okay, enjoy, think of me when you come. xxx"

Tamara and Sheryl bumped into each other twice more during the day and smirked knowing smiles at each other. Four o'clock arrived and the school fell silent, save for the odd vacuum cleaner in the distance. Tamara did some marking in her office until five forty five. She hadn't been able to concentrate for the last ten minutes or so. She'd got butterflies in her tummy and tingle in her pussy that she always felt before preparing to seduce a new conquest.

********************

When she arrived at the large modern pub Orla was already there. She was sipping a glass of wine to calm her nerves. The lounge was large and almost unoccupied at just after six o'clock. Orla gave a friendly smile as Tamara approached her table. She was dressed in the same well cut grey skirt suit that she wore to parents' evening two nights previously. With her legs crossed, she showed enough beautifully formed thigh, swathed in nude holdups, to give Tamara's pussy a little pulse of excitement.

Orla's pale blue formal shirt and black stilettos completed a very sexy well heeled appearance, which was enhanced by a simple string of dark grey pearls at her throat. Her large green eyes flashed at Tamara's beautiful hazel eyes again and both women felt a surge of excitement and anticipation.

"I'm so glad you didn't stand me up, I was pretty full on with you the other night, I thought I might have frightened you off."

"You were definitely bold and confident, how come you were so sure that I would be interested"

I watched you most of the evening, you had an eye for the men, and they for you to be honest, but it was the way your eyes followed the deputy head when she walked through the hall. I mean, I don't blame you, she's hot, but I can usually tell whether a woman is just looking at how another woman is dressed, or what she might look like undressed."

"My God, was it that obvious?" said Tamara, not letting on that she knew exactly what Sheryl looked like undressed.

"No, it was just a moment, not everyone makes a living out of reading women's minds like I do."

"How come?"

"I'm a female escort... for women, and now and again, I like to make love to a woman that hasn't paid for my services. You look a little surprised Tamara, here sit down and I'll get you a drink. What will you have? Oh dear, I hope you haven't changed your mind about me."

"No, God no, you're... well you're..."

"I'm what?"

"Incredibly desirable and seductive, I'm just a bit stunned that's all. A large white wine please."

Orla went to the bar to order Tamara's drink. Tamara sat watching and admiring her, still a little shocked, but keen to know a lot more about the exciting Orla. She returned with Tamara's drink.

"I haven't said yet that you look stunning Tamara. So sexy, and you give off a forceful vibe, I can completely understand why Jessica turns to jelly in your presence. Don't take this the wrong way but you could make an absolute fortune as an escort for women. Loads of women want to be taken in hand by a strong woman like you."

Tamara knew this only too well, but she'd never contemplated charging for her services.

"Well I don't sense that you're the submissive type either."

"No, I think we're quite well matched. I'd love to have an affair with you. Are you married or in a relationship?" said Orla.

Tamara explained about Jack and their agreement. She also confessed to having fucked thirty or so men and women in the past two and a half years. She could tell Orla was impressed. She probed Orla on her 'work' and learned that she restricted herself to one client per week, that they were regulars and that she never took clients home.

"You don't have to answer this, obviously, but how do you earn enough to live on with just one client per week?"

"Oh I charge between £150 to £250 per date, depending on exactly what the client wants. I also have a small business running a dating agency exclusively for women who want to meet women, it's very high end, executive and professional only, the annual fees are eye watering, but you'd be surprised how many respectable women are looking for a discreet service like mine. That's my main source of income, I make a good living from it."

"And what do you do when you're being an escort?"

"Often we go out like on a date, sometimes I just visit them at home for sex. Some women are 'out' and they treat me like their girlfriend in public, but some are more secretive and only want intimacy in their homes. Some are lesbians, some are single and some of those like to be with men too, some are married and desperate for the love of a woman."

"It sounds complicated."

"Not really, I've probably had about a dozen different clients in the last two and a half years."

"And Jessica, does she know what you do?"

"She knows about the dating agency, but not the escort side of the business. I'll tell her when she leaves school this summer, I don't want anything to disrupt her progress just now."

"Very sensible, she really is bright and she'll do well."

"And you're sure you haven't been put off by my work?"

"Definitely not, I'm finding you fascinating now as well as devastatingly sexy."

"Good, so how are we going to go about this? I really do want to fuck you but the nights are drawing out now, so a quickie in the car is out of the question. Can we get together sometime soon?"

"We could get a room now."

"Oh, I'm sorry Tamara, didn't you get my text? I've got to be home for eight o'clock tonight, my mother is insisting on phoning me from Ireland at eight on the dot with news about my niece being pregnant. She left me a message this morning saying 'I've got some big news, be in at eight.' I've got to pretend I don't already know; my niece phoned last night. But I thought we could still meet this evening to plan a date"

Tamara looked at her text messages.

"Oh God, sorry Orla, I missed it. Never mind, look, it's half term in about ten days, my Jack's going to want the house to himself and his girlfriend for the first weekend, can you wait until then?"

"Yes, of course, I'm not seeing a client that weekend so I'll keep it clear"

"I'd love to make it a real date, you know, get a hotel room, go for a nice meal then the theatre then back to the hotel to deflower you."

"Ha ha, I like the sound of that Tamara. Will we be lovers in public or just in private?"

"Depends where we are. I'll sort out some tickets for a venue, and I'll book a restaurant and a posh hotel. But it'll be wise to avoid our home city, I know a charming hotel in the centre of Oxford if that's okay? I don't think we'd need to be overly secretive in a city where neither of us are known."

"That's wonderful, it makes a change for me to be dated and not to have to make the arrangements. But we're going halves on this remember, you're not going to be one of my clients."

"Okay, agreed, I feel a new dress coming on, and some expensive lingerie."

"Me too, and I'll ditch the holdups and wear stockings with suspenders just for you."

"You're definitely my kind of woman, while we're on the subject, I assume you're wearing holdups now?"

"Yes, why?"

"Well I know you said it's not dark enough for a grope in the car, but I honestly cannot wait until half term to get a taste of you. I know a very secluded spot where we can get cosy with each other. It's a disused canal bridge about three miles away. I can take you there now, so to speak, and bring you back here before seven thirty."

"I'll ignore the awful puns."

They both laughed. Orla put her left hand on Tamara's left knee. Her touch was electric.

"Okay, I trust your judgement and I'm longing to feel your fingers inside me. Let's go."