The Elephant in the Room Ch. 02

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MicheleNylons
MicheleNylons
3,965 Followers

Elizabeth did exactly that. She sought out Rosemarie, a friend she had made who had told her all about the Saint Trinian's Escorts, even though she shouldn't have. They stayed awake until the early morning, drinking and smoking in Elizabeth's room while Liz grilled her about working as an Escort.

Elizabeth asked to see Miss Swindon the next day and was given an appointment after the last class of the day.

Elizabeth hadn't had time to change for the meeting and was still in her school uniform.

The uniform at Chelmsford Finishing School had changed little over the years. It consisted of a grey pleated A-line skirt with the hem resting mid-thigh, a white nylon or satin long-sleeved blouse, and a navy blue blazer that hung to the hips. Girls were now allowed to choose their own underwear so longs as it was white and were allowed to wear tights of fifteen denier or less in summer and thirty denier or less in winter. The girls were required to wear black low-heeled court shoes but most of them flaunted the rules and wore moderately high heels. They still wore the traditional French Topper hat as part of the uniform.

Some people claimed the uniform sexualised the girls but as the average age was eighteen with a minium age of sixteen and maximum of twenty-two, the girls in general liked the uniform.

Once again Valerie was immaculately dressed but she'd taken off her jacket and kicked off her high heels now that school was out. She indicated for Elizabeth to close the door and pointed to the same lounge chair she had sat in yesterday. She poured them both generous nips of scotch.

Elizabeth dropped the signed copies of the Saint Trinian's Escorts code of conduct and her contract on the coffee table.

"Very dramatic dear. Anyway, I'll assign Rosemarie to be your mentor and chaperone, you start this weekend ok?" They chinked their glasses together to seal the deal.

"Ok. We're all done. Report to Emily at the gardener's cottage tomorrow afternoon at three," Valerie finished her drink.

'The cottage' as it was referred to, was where the Escort agency was run from, located in a copse at the back of the school. It also had a bedroom that the girls used to entertain visiting punters.

Elizabeth spun on her heels and headed for the door.

"Anyway; I suppose I had to lose my virginity sometime," Elizabeth said resignedly reaching for the doorknob.

Valerie was stunned.

"Get back here right now!" she bellowed.

"Jesus! You're a virgin? What about old Bertie?" Valerie held Elizabeth by her shoulders and examined her eyes.

Elizabeth shook her head.

"Jesus!" Valerie exclaimed again.

"I'm not sure I want some lecherous businessman or fumbling schoolboy taking your cherry. You deserve better," Valerie said.

Elizabeth dropped her chin; once again she felt inadequate. But her mother's advice echoed in her psyche.

"What about you miss?" Elizabeth lifted her head and engaged Valerie.

"Don't be silly," Valerie swallowed.

"But you said you have the same as a man down there," Elizabeth took a step forward.

"And wouldn't it be nice for a lovely special lady like yourself to be my first. Someone gentle and kind who understands women," she took another half step and was standing toe to toe with Valerie.

"Well that may be so but..." Valerie didn't get to finish her sentence.

Elizabeth pressed her lips to Valerie's and tentatively put her arms around her.

"Oh Jesus," Valerie whimpered and returned Elizabeth's kiss.

The two women embraced and kissed each other softly, taking time to explore each other. Valerie slipped her tongue hesitantly into Elizabeth's mouth, tasting the girl's sweetness. Elizabeth had never experienced that before but she liked it; she slid her tongue past Valerie's lips and savoured her piquancy; Scotch whisky, cigarettes and breath mint. She breathed in Valerie's perfume as their bodies pressed together.

There was no urgency or harsh thrusting and humping like she had experienced with Bertie. Valerie pressed against her softly, tentatively, their supple breasts yielding to the pressure. Elizabeth had never been held and kissed like this before; a yearning and excitement was building inside her. She felt herself becoming wet.

The two women kissed and caressed each other; to Elizabeth who was yet to kiss a boy, the experience was utterly delightful. The soft feminine feel, taste and smell of Valerie was so different to the harsh humping she'd endured as she lay under or beside Bertie.

Valerie helped Elizabeth out of her blazer and slowly began to unbutton her blouse; taking her time, her long red fingernails gently scraping Elizabeth's delicate white skin. Elizabeth hissed with pleasure as Valerie stroked and caressed Elizabeth's flat belly and then languidly dragged her fingernails up to her breasts. Their kisses subtly intensified when Valerie reached for the clasps on Elizabeth's brassiere.

Elizabeth moaned when Valerie cupped her small firm breasts, her fingers grazed Elizabeth's nipples, eliciting exquisite little shards of pleasure.

"Oh Miss that is so wonderful," Elizabeth simpered when Valerie broke their kiss and lowered her lips to Elizabeth's bosom.

She licked Elizabeth's milky-white globes and then she let her tongue trace the areola surrounding Elizabeth's little berry-shaped nipples. Elizabeth gasped and guided Valerie's mouth to her nipples and when Valerie used her lips, tongue and teeth to suck, lick and nip them; she let go a stifled scream.

Valerie smiled and removed her face from Elizabeth's bosom. The look of disappointment on Elizabeth's face didn't last long as Valerie kissed her harder this time; driving her tongue into Elizabeth's mouth. She took a breath and smiled into Elizabeth's pretty face.

"Your turn sweetheart."

Elizabeth needed no further encouragement. But being inexperienced, she took her lead from Valerie. She nervously unbuttoned Valerie's blouse.

"Take your time honey, enjoy it," Valerie smiled into Elizabeth's eyes.

And she did; she eased Valerie's blouse from her shoulders and allowed it drop to the floor. Valerie's breasts were bigger than Elizabeth's but were not ponderous. They were firm for a woman her age; cupped securely in a black lace and satin bra.

Elizabeth traced the outline of Valerie's nipples through the gauzy fabric; her nipples hardened and Valerie whimpered a little.

"You're a fast learner honey," she sighed and lowered Elizabeth's head to her bosom.

Elizabeth fumbled with the clasp on Valerie's bra but Valerie was patient and allowed Elizabeth to take her time. She didn't want to intimidate Elizabeth, she wanted her first time to be wonderful; she felt privileged that she the one to take Elizabeth's virginity.

Elizabeth lapped at Valerie's breasts while struggling with the clasp but then Valerie's brassiere fell away revealing her cleavage in all its glory. They were full and shapely and begged to he suckled. Elizabeth obliged and Valerie gently held Elizabeth's face to her bosom as Elizabeth explored them.

During her exploration Elizabeth found the fine silvery scars underneath each breast; instead of being repelled she followed the scars with her lips, kissing then softly.

Valerie smiled and stroked Elizabeth's hair.

"How else does a tranny get great tits like these," she joked.

"Mmm; they're wonderful," Elizabeth nuzzled Valerie's left breast and stroked the other with her fingers.

Valerie pulled Elizabeth away from her chest and lifted her face so that she could kiss her again. They wrapped their arms around each other, pressing their bosoms together. Valerie slid her hands down Elizabeth's body into the waistband of Elizabeth's skirt. Elizabeth froze momentarily but Valerie persevered and began to slide Elizabeth's skirt down her legs. She dropped it and it pooled around Elizabeth's feet and she kicked it away, not wanting to break the kiss.

A scintilla of the scent of a woman aroused reached Valerie's nostrils and her already tumescent penis began to become fully hard. This was a problem for Valerie as she was gaffed. That is, her testes were pushed up inside her body and her penis was wrapped in her scrotal sac and taped between her legs.

"Ahem...I have a little, well not so little problem," Valerie quipped.

"What's that?" Elizabeth looked concerned.

Has she done something wrong?

"Probably best shown rather than explained," Valerie smiled seductively.

She took Elizabeth's hand she guided it under her skirt to the front of her black satin knickers. Elizabeth stroked the front of Valerie's slinky panties and found nothing untoward. The she realised.

"Oh my god! I've seen you in your sports gear; in tights and leggings and that's why I thought the girls were joshing me about you being transsexual. You have...well you have a mound just like the rest of us girls. So I guess it's hiding," Elizabeth smiled mischievously.

Her fingers went exploring and found what she was looking for tucked under Valerie's crotch.

"Probably best if I...oh my god Elizabeth!" Valerie was about to suggest that she remove her gaff; but Elizabeth simply ripped off the surgical tape and gripped Valerie's penis as it sprang free.

"Mmm that's what one feels like," Elizabeth sighed and crushed her lips against Valerie's.

All the times she'd been panty-popped by Bertie she had never seen or touched his penis. It was always done in the dark and was usually over with quickly. She'd only ever felt it against her buttocks or her pubic mound and always with her knickers on.

Valerie did the equivalent of a kegel and her testes dropped into her scrotal sac. Elizabeth caressed Valerie's erection through the silky fabric of her panties for a while but she wanted to explore the intriguing appendage. So she did; she hefted Valerie's erect phallus in her hand and began to examine it.

She had seen pictures of penises of course and the girls who worked at Saint Trinian's had told her about the penises they had encountered 'on the job'.

"Some are big, some are small, some look nice and some look ugly, but really it's how the man uses it that counts," Rosemarie had said to her one day sitting in her room drinking and nattering with some of the other girls.

"Yeah...but I like the big ones," Cynthia Williams had said and they all started giggling.

Cynthia Williams was not a boarder and as such was not employable as a 'Saint Trinian's girl' but she was well known for her promiscuity.

Valerie gasped and Elizabeth's fingers traced the veiny shaft of her penis and finally found the bulbous glans and the ever so sensitive fraenulum. Elizabeth found the appendage quite fascinating and extremely exciting, she was getting wetter.

"Oh that's so good Lizzy," Valerie hissed as Elizabeth used her fingernails to gently scour the corona of her glans.

Their kisses were becoming frantic and Valerie unbuttoned and dropped her own skirt so the women were now dressed just in knickers and hosiery. Elizabeth was wearing tights and Valerie hold-up stockings. Elizabeth was still in her heels and towered over Valerie so she kicked her shoes off too.

Elizabeth pulled down Valerie's panties and took her penis fully in her hand and began to stroke it. Valerie traced the outline of Elizabeth's labia through her white satin panties and the gusset of her tights. They were already damp and pungent.

Elizabeth gasped. It was the first time anyone other than herself had touched her there and she had never masturbated.

The feel of Valerie's fingers, sliding the delicious silky nylon into her wet crevice was sublime. Then Valerie slipped her fingers inside the gusset of Elizabeth's knickers and slid her middle finger inside her fleshy labia. When she found Elizabeth's clitoris Valerie had to hold Elizabeth up as her knees buckled.

Valerie guided Elizabeth over to the day bed and lay her down. She smiled down at Elizabeth, Valerie was now naked except for her stockings. Valerie eased Elizabeth's panties down her legs and tossed them aside. She was tempted to use her mouth on Elizabeth but both of them were more than ready.

Elizabeth opened her legs and Valerie knelt between them and lowered her face and kissed Elizabeth who raised her arms and pulled Valerie to her. Valerie's cock nestled in the folds of Elizabeth's labia, only a whisper of nylon between her penis and Elizabeth's vagina.

She rubbed her cock against Elizabeth's sex and Elizabeth moaned with delight. This was nothing like what Bertie did to her; this was sensual and exciting. Valerie's lips and tongue found Elizabeth's breasts and she began to suckle but Elizabeth wanted to kiss, she eased Valerie's face back to hers.

"Take me Valerie; be my first," Elizabeth looked into Valerie's eyes with both affection and lust.

Valerie used a fingernail to snag the nylon in the gusset of Elizabeth's tights. She made a hole and put her finger in it and then ripped out a scrap of gusset big enough for her to get her penis through.

Valerie positioned her penis inside Elizabeth's labia at the entrance to her vagina. She kissed Elizabeth again and then looked at her lovingly.

"Sure?" Valerie asked.

Elizabeth nodded vigorously and wriggled her hips in encouragement

There is a common misnomer that a girl's hymen is positioned inside her vagina; it is in fact a band of tissue at the entrance and as Valerie pushed forward slowly but gently, Elizabeth's hymen tore. The pain was hardly noticeable over the intense feelings of pleasure she felt as a hard penis entered her sheath for the first time. Valerie ground her pubis against Elizabeth's once she was fully penetrated so that Elizabeth's clitoris was stimulated.

"Oh my god! This is wonderful!" Elizabeth cried and raised her hips from the couch, encouraging Valerie to fuck her.

Valerie started slow and gradually increased the pace as Elizabeth clung to her; their nylons rubbed together intensifying their pleasure.

Valerie tried her hardest but Elizabeth was so tight that she couldn't hold back her orgasm for long. Elizabeth was moaning and crying all once as she squealed and howled with delight, the phenomenon of her first intercourse and approaching orgasm was unbelievably pleasurable and satisfying.

Elizabeth drove her groin upwards and met Valerie's thrusts as they both approached extremis. Valerie drove her tongue into Elizabeth's mouth and gripped her tight and buried her cock right up to hilt in Elizabeth's vagina, she ground her hips as Elizabeth screamed with the passion at magnitude of her first orgasm. Valerie ejaculated deep inside Elizabeth and she too shrieked with excitement at the paroxysm of her climax.

They kissed and pawed at each other as their passions crested and waned and finally lay exhausted with Valerie's cock still deep inside Elizabeth. They mewed and caressed each other, kissing softly now their ardour was waning.

Elizabeth smiled up at Valerie.

"So that was fucking?" she grinned.

"I like it," she giggled.

"It will be different with a man," Valerie stroked Elizabeth's fringe out of her eyes.

"But you were my first," she kissed Valerie quickly.

They lay like that for a while and Valerie explained to Elizabeth what it would be like to be with a man and also about oral sex, which she would be bound to have to perform.

"Mmm...interesting. Why don't we try that now so you can teach me? Then you can hop on me and do that again," Elizabeth said cheekily.

"Why you little minx!" Valerie laughed.

But they did.

When Elizabeth and Valerie were utterly sated they got dressed and Valerie poured drinks and handed out cigarettes.

"So tomorrow is your first day on the job," Valerie said as they sipped and smoked.

"It's easy really; just make sure that you are in control but let the man think that he is," Valerie said sagely.

Elizabeth had heard her mother say exactly the same thing over and over again; the lesson was being reinforced.

Elizabeth left Chelmsford Finishing School for Young Ladies in her twentieth year. She had some considerable savings and a sex education that was unsurpassed.

Like all graduates she swore that she would never discuss her time working as a prostitute for Saint Trinian's Escorts, which was embedded in the contract she had signed. Elizabeth would be leaving with a decent education and the requisite skills to catch her a husband.

Which is what she did when she met Stephen later that year.

To be continued

MicheleNylons
MicheleNylons
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5 Comments
AnonymousAnonymous7 months ago

Now we get to see your usual attention to detail and a much filled out narrative. Very entertaining; especially engrossing with the surprise introduction of a TS Headmaster of St. Trinians - delicious!

AnonymousAnonymousalmost 4 years ago
More Elizabeth Please!!

I know this is not your "style" but this is a good story. More Elizabeth please!

AnonymousAnonymousabout 4 years ago
I know it has been awhile

I know you have been away from this story for awhile. Would love to read more of this take.

AnonymousAnonymousover 4 years ago
Loved this story

I have read quite a few of Michelle Nylon's stories and I love her as an accomplished writer for Literotica . I would definitely love to actually meet Michelle in real life because of her stories she is the most beautiful woman in the world. But please give me more chapters too this story so l'm not left frustrated.

Jb423Jb423about 6 years ago

Enjoyed reading her origins. Audi make sense why she wants her husband "Stephanie" to be sophisticated. I just hope she doesn't end up hurting her husband and her marriage

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