tagTransgender & CrossdressersFinishing School For Ladies Ch. 02

Finishing School For Ladies Ch. 02

byMicheleNylons©

Chapter Two -- The Butterfly Emerges

"So why Valerie Swindon?" Sally asked, sipping a gin and tonic with her stocking feet up on the coffee table.

"It's the first name that popped into my head so no one should associate it with anything to do with my past life," William replied, also sipping a G and T and smoking a cigarette.

"That's smart. A lot of trannies take on femme names that resemble their male names; Steven becomes Stephanie, Robert becomes Roberta, Michael becomes Michele, and so on.

"You really have mastered the art of makeup," she smiled at him appreciatively.

"I like artistic stuff; and when I was staying with a friend a while ago, I found out through his sister that I liked feminine stuff too," William appraised the glowing end of his cigarette.

"Did you ever try on your mother's underwear or her clothes?" Sally smirked.

"Why would you ask that!" William was suddenly defensive.

"Don't get angry babe. That's how most of us trannies start out, trying on our mother's or sister's knickers and stockings. Slipping into a slip," she giggled, the gin was taking effect.

"I told you. I'm not doing this because of any fetish or sex malarky; I'm doing it as a disguise," William sounded enraged.

Sally snuggled up to him on the couch and he couldn't but help notice her dress ride up to the very top of her thighs; the scent of her perfume was very alluring.

"You're not angry with me are you honey," she kissed his cheek teasingly.

William blushed.

"I told you there is no need for you to provide any intimate services," he replied, reddening.

"But what are you going to do when those randy men come after you Valerie? I've seen how you look in makeup and when I get you dressed you're going to look stunning," she nibbled on his ear playfully.

William pushed her away.

"Don't call me that until I am fully dressed. And I'm sure I will be able to deter any advances made on me in that way. I am not at all interested any of that perverted stuff. I might be dressed like a girl but I will still be a man," he growled.

"Like me?" Sally laughed.

"Not like you! You're...you're..." William faltered.

"A tranny?" Sally smiled solicitously at him.

"You don't find me attractive?" she leaned into him and slid her nylon-encased legs along his thigh and nuzzled his earlobe.

"Stop that! You're drunk!" William blurted out and drained his own glass.

Sally blew in his ear and whispered.

"And so are you and I think you fancy the pants off me," she raked her red fingernails across his fly where a thickening bulge was growing.

Sally leaned into William and offered her lips and he couldn't resist. They kissed. At first tenderly and then their ardour grew. Sally put down her drink and offered William her complete attention. He might be effeminate but he was still handsome. She kissed him and snuggled up against him.

The hotel room was dark except for the lamplight, a haze of cigarette smoke hung from the ceiling. William had been drinking as heavily as Sally had and their defences were down. Sally snaked her slim body around William and he responded, kissing her passionately.

His hand slid up her thigh, the cool nylon of her pantyhose was scintillating to his touch. His hand slid under the hem of her dress and reached the top of her thighs; his fingers drifted across the front of her silky panties and he was surprised not to find a bulge. After all he knew Sally was a transvestite.

Sally's fingers traced the outline of William's erection in his tight jeans and then she squeezed his cock through the denim and he gasped in her mouth.

Williams fingers caressed the front of Sally's panties and then drifted to her crotch. He found her penis there, hot and hard, taped between her legs. He pulled his hand away, shocked.

Sally kissed him harder and then bit his earlobe and whispered.

"What did you expect to find? You know I'm a tranny?" she moved her lips back to his and playfully bit his lip.

William returned his hand inside Sally's dress and he tentatively stroked her through her knickers and pantyhose. He was actually quite delighted when she groaned and her penis became harder. He tore away her gaff.

Sally pulled down Williams fly and extracted his erect penis. Sally stroked and squeezed William's cock while he kissed her and tentatively caressed her member.

Sally extracted herself from William's embrace. She stood up and held out her hands and William arose from the couch. She unbuttoned and removed his shirt and then unbuckled his belt and helped him shuck off his jeans. His socks joined his shoes and he stood before her naked except for his briefs tented by a generous erection.

Sally reached into William's underpants and grasped his hard cock and stroked it. She stepped into him and his erection pressed against her belly as she caressed his engorged penis. They kissed passionately and William undid the zip at the back of Sally's dress and helped her out of it.

She stood before him; her small but well shaped breasts cupped in a lacy black brassiere, matching black lace panties over the gusset of her sheer-to-the-waist tan pantyhose. She kept on her high heels and she matched him in height. They kissed.

William pulled her body against his, enjoying the sensation of satin, lace and nylon against his sensitive skin. Sally pulled down his underpants so he was naked.

Sally led William to the bed and lay him out prone. She knelt over him and lowered her face to his crotch and engulfed his penis with her hot wet mouth.

William groaned. It was the first time he had been fellated and the feeling of Sally's tongue on his penis was exquisite.

Sally scooted around on the bed so her groin was over William's mouth while she continued to suckle him. He tentatively liked at her swollen penis through the layers of pantyhose and panty but he soon became frustrated. He pulled down her knickers and freed her erection from the sheer gusset of her pantyhose and took it in his mouth.

He was pleasantly surprised to find that it was quite a nice sensation. He mimicked everything that Sally did to his penis.

If she teased his fraenulum he did the same to her. If she sucked on his shaft and slavered his glans he did the same to her. If she tentatively explored his scrotum with the tip her tongue he did the same to her.

Sally was so excited; her young protégé was arousing her like he was a well versed lover. Her cock was leaking preseminal fluid which William gladly suckled and swallowed as she did the same to him.

But now Sally wanted something more. She wanted to feel like a real woman; the only way she knew.

Sally snaked underneath William so they were face to face again, kissing each other passionately.

She lifted her legs. Her pantyhose were already pulled down to her thighs and all she had to do was grasp William's penis and guide it to her entrance.

He looked down at the gorgeous creature underneath him and she raised her nylon-sheathed legs and rubbed them on his flanks as he slowly entered her.

Sally was so tight, even though unbeknown to him she had pre-lubricated herself in anticipation of such an event, she was so tight that he was forced to take his time thrusting himself into her.

Sally gasped as William slowly entered her but she hung onto him and encouraged him by playfully biting his earlobes and lips, raising her buttocks off the bed to meet him, and rubbing her sheer-nyloned legs against his sensitive flanks.

When he was fully in her she kissed him passionately and began to fuck him. She wrapped her arms around his shoulders and her legs around his waist and lifted herself up to him and wriggled her bottom.

William groaned and kissed her. He dropped his hands to her hips and pushed her down into the bed and fucked her hard and fast. His climax was on him and he felt his spend ready to ejaculate.

Sally sensed it and pushed back against him and drove her tongue into his mouth. William felt Sally's hard cock pressing against his flat belly, dribbling precum. He thrust hard and fast and emptied himself inside her, driving her down into the bed.

Sally screamed and rose to meet him as best she could, wrapping her arms around him and her nyloned legs drummed against him. She ejaculated against his tight stomach and sighed. It felt so wonderful.

William fucked Sally hard and fast until he was spent and exhausted and then he lay on top of her kissing her tenderly, stroking her hard nipples absentmindedly.

They kissed and stroked each other as their lust subsided into sensuality. Sally kept her silken-clad legs wrapped around William as she sensed he really liked the feeling of the gossamer fabric on his body. Their bellies were wet with Sally's semen, and William's spend was dribbling from Sally's anus as his cock slowly deflated.

He looked down at her and smiled.

"Besides being a wonderful cosmetician you are quite the accomplished lover," he grinned.

"For a young man, you are quite accomplished yourself. I am guessing there has been some tutelage?" she grinned up at him.

"A story for another day but that was totally amazing. So exciting and unconventional for me," William beamed down at her.

"Yes. Imagine you are in my position," Sally grinned up at him.

William's face clouded over.

"I hardly think so!" he growled.

"Sure honey. Wait and see. Now turn out the light and cuddle up to me. I'm tired," she kissed him on the cheek and manoeuvred into a spoon position.

William turned out the lamps from his bedside switchboard and snuggled up to Sally. He kissed her shoulder and then pulled the duvet over them.

"Goodnight princess," he whispered.

Sally wriggled her buttocks against his goin and mewed. They were both asleep in minutes.

Sally woke to the feeling of William's cock probing between her buttocks and she smiled. She reached back and guided his glans to her sphincter and relaxed so he could enter her. She was still lubricated from the previous evening's lovemaking.

She pushed back against William as he slowly thrust in and out of her tight anus and she worked those internal muscles to grip his cock and encourage his orgasm. Sally enjoyed being fucked but felt no need to orgasm herself and let William enjoy fucking her as she writhed against him to encourage him. He took his time but she felt him come as her back passage became flooded with warm secretions.

She smiled and when William was sated she turned around and they kissed and cuddled.

After a while she reached for the bedside phone and ordered coffee from room service and sat up in bed and lit them both a cigarette.

"So?" William said.

"So what?" Sally grinned down at him and ruffled his hair.

"So does it feel as nice being the girl as it does being the boy?" he grinned up at her.

"Oh darling...it feels so much better," she laughed.

The doorbell rang and Sally slipped into one of the hotel's complimentary bath robes and let in the room attendant with the coffee. She tipped him a quid and gave him their breakfast order.

"No big a breakfast for you Miss Swindon. We're getting you a wardrobe today and I want it to fit. But I'm having the full English," she laughed and lit them both another cigarette and poured the coffee.

They had a delightful day out shopping; purchasing lingerie, shoes, jewellery, and perfume. Sally helped William try on skirts, blouses and dresses in the fitting room at Debenhams Department Store. William needed to go to his bank once again and make a substantial withdrawal, but he didn't care. Sally was delightful and he had never felt so unreserved and unrestrained as he did in her company.

They had tea together at a stylish tea house and nattered away like old friends.

They stopped at an up-market hairdressers and had William's hair styled into a classic bob with highlights. They both approved the coiffure and William tipped the hairdresser five quid.

William had an intrinsic sense of style and grace. Sally was impressed with his forethought and appreciation of what suited and fitted him. She could hardly wait to get him back to the hotel so she could make him up and dress him and reveal Valerie to world in all her splendour.

Later that afternoon, the hotel room bed, the couch, and the chairs were littered with shopping bags containing the purchases that the two had made.

Sally helped William change into a black, mid thigh, pencil skirt and mauve blouse. She showed him how to tuck and gaff and watched appreciatively while he slipped into a black lace garter belt, flesh-toned fully fashioned stockings, and a mauve satin panty and bra set.

Sally and William had discussed the issue of breasts. Valerie could either turn up to the interview flat-chested or with a stuffed brasserie. They both decided that it would not be too untoward for a girl of her age to be flat-chested and it presented the opportunity to use breastforms later on if she needed to show breast development.

Sally sent William to the bathroom to do his makeup.

"When you emerge. You will be Valerie Swindon. Your identity as a man will be forgotten for the foreseeable future. Do you understand?" Sally said solemnly.

William nodded and disappeared forever.

The creature that emerged from the bathroom was Valerie Swindon and she was gorgeous.

Valerie was delighted to find a bottle of Dom Perignon on ice when she emerged from the bathroom. Sally had ordered it to celebrate.

Sally gasped. She knew that her protégé would be passable but Valerie was stunning.

Valerie had paid attention to everything Sally had said to her. She placed her feet one in front of the other, toe down, then heel, and sashayed into the room.

Sally allowed Valerie some time to get used to walking in high heels and then she sat her down and they toasted with the champagne and had one last smoke before the biggest test of all.

"Just be confident out there darling; you look stunning so you're going to attract attention. Your voice is very feminine, very smoky and seductive, so there is no reason for you to get clocked. Just think and act like a girl," Sally said.

The girls set off down the corridor and into the elevator and through the lobby. Valerie flung a small leather handbag over her shoulder and they strutted down the street; two gorgeous girls confidant in themselves.

Valerie was a little apprehensive at first, even though she appeared outwardly confident. She was glad she had Sally with her to provide moral support but she knew that she would have to get comfortable being herself from now on; for two years at least.

After a while Valerie's feet began to hurt.

"Walking in heels takes practice babe. Look, what about we stop in that pub over there and get a drink. It will also expose you to being a public place close to people," Sally pointed to a pub across the road.

Sally and Valerie sat in a booth sipping gin and tonics, smoking cigarettes, and spent a pleasant hour turning away would be suitors.

"I told you men would try to get into your knickers. You are quite a stunner," Sally smiled at Valerie.

"You know it's so strange. I feel so feminine and I'm actually very flattered that men are finding me attractive. I didn't think I'd feel like this," Valerie sipped her drink through a straw, very ladylike.

"But don't rush into anything. Allow yourself to get used to being feminine. You're going to spend the next two years of your life as Valerie, take your time and enjoy the transition," Sally reached across and took Valerie's hand in hers.

"I owe you so much already," Valerie leaned over the table and kissed Sally quickly on the lips.

"Hey! Are you two lezzies? What a fucking waste!" one of the more inebriated men who had come on to them yelled from the bar.

"And get used to idiots like him," Sally smiled.

"I have really enjoyed today and especially enjoyed being out with you. But now I want to go back to the hotel," Valerie finished her drink.

Sally looked a little disappointed. Today was her last day with Valerie and she really liked this young tranny.

They walked back to hotel, pretty much in silence. Valerie kicked off her heels and poured drinks. She turned around to see Sally picking up the meagre belongings she had arrived with.

"What are you doing?" the concern evident in Valerie's voice.

Sally hid her face from Valerie to disguise her sadness.

"Two days Valerie. That's what you wanted. Well two days are up and there is nothing more I can teach you. The rest is just down to experience and will come with time," Sally wiped a tear from her face and stuffed some underwear into a carry bag, her back to Valerie.

Valerie strode over to Sally on stockinged feet and spun her around. She searched Sally's eyes.

"Do you want to go?"

"Of course not," Sally grimaced.

"Then don't. Stay with me until my interview," Valerie pulled Sally into her arms and kissed her.

It was so sensual; their soft lipsticked lips pressed together gently at first and then Sally parted her lips and Valerie parted hers and used her tongue to explore Sally's sweet mouth. Valerie held Sally in a firm embrace, she inhaled Sally's perfume and kissed her passionately. This was different to before. Valerie was very conscious and appreciative of the feel of her soft silky lingerie and stockings. She felt so feminine but she was acutely aware of Sally's femininity as well.

It was strange but sensual, licentious, and lascivious...downright naughty!

They fell on the bed, Valerie straddling Sally. They kissed lovingly but lustfully and Valerie slid her hand under Sally's skirt and went exploring inside her panties. She removed the tape from Sally's gaff and squeezed her thickening erection. Sally reciprocated and stroked Valerie's erect phallus through her silky panties.

The two lovers broke apart for a few seconds to shuck out of their skirts and blouses and then fell on each other again lustfully, kissing and rubbing against each other and squeezing hard cocks through satin panties.

Both cocks became unencumbered from their knickers and they rubbed them together, Valerie straddling Sally.

"Oh my! I seem to have awoken the unconscious slut inside of you," Sally giggled.

"Oh daring. I have never felt anything so amazing as this," Valerie moaned with lust.

Valerie lowered her face to Sally's groin and suckled her erect penis. Sally simpered and held Valerie's head and guided her mouth up and down on her cock.

Valerie slavered at Sally's tumescent member, flicking her tongue along the sensitive fraenulum and using her lipsticked lips to suckle on the shaft.

"Oh god you're good at that darling," Sally whimpered.

Valerie wriggled and squirmed and was able to get underneath Sally. Sally straddled Valerie, kissing her and rubbing their cocks together.

Valerie reached between their bodies and positioned Sally's cock at the entrance to her anus.

Sally froze.

"Oh no darling. I don't think you are ready for that yet," she stroked Valerie's face affectionately.

Valerie smiled up at Sally and suddenly gripped Sally's hips and drove her lower body upwards, impaling herself on Sally's cock.

At first the pain was excruciating and Valerie screamed out in agony.

"Oh no darling! I'm sorry," Sally mewed and pulled her penis from inside Valerie's sphincter.

"You didn't do anything. I did it," Valerie smiled up at her.

"And I want it. I really want it," Valerie begged.

Sally reached over to the nightstand and snatched her purse and took out a tube of KY jelly and slathered it on her penis and rubbed it into Valerie's little winkle.

"Let me do it nice and slow and you tell me to stop if it hurts. You're supposed to enjoy this, not get hurt," Sally said and kissed Valerie on the lips.

She lifted Valerie's legs and put them over her shoulder. She kissed Valerie's stockinged calves and smiled down at her lover.

Report Story

byMicheleNylons© 4 comments/ 11924 views/ 16 favorites

Share the love

Report a Bug

Next
2 Pages:12

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:

   Cancel