The Transformation to Lindsey, part I

Part I

Mike woke up in the middle of the night soaking wet, sweating from everywhere, like all the prior nights of the weeks leading up to his vacation. For the past two weeks he has been having dreams, the same dream, and the response has been the same as well, sweat and abrupt waking. He turned to his wife, Lucy, but she was sound asleep. “Thank goodness,” Mike thought, he didn’t want to disturb Lucy, especially over this dream. 

Mike glanced at the clock, 3:15am. He had two more hours until the alarm went off. Lucy & Mike were catching a 9am flight to Virgin Gorda. Mike laid back down and tried to go to sleep for the next two hours but was unable to. He kept thinking of this recurring dream. 

Mike was Lindsey in his dream. Lindsey was a hot blonde bombshell with big breasts and a perfect hourglass body. In this dream she was sun bathing on the beach, topless. A handsome young man was standing over her with an ice cold margarita. In fact, a cold drop of condensation from the glass dropped onto Lindsey’s back and that is what got her attention. Actually, that cold sensation is what woke Mike up from his dream. As Mike laid in his bed with the sheets cool due to his sweat, he rationalized that the sweat cooling on his back is what he was feeling and the sweat is what actually woke him up. Mike couldn't stop thinking about his nightly dreams!

Lucy and Mike arrived in Virgin Gorda the next afternoon. The flight and water taxi to the island was uneventful except for the fact that the airlines lost Mike's luggage. Lucy spent twenty minutes talking to the airlines and the resort to get Mike's luggage handled and she told Mike that everything was under control. Lucy reassured him that he didn't have to worry about a thing.

As they approached their villa, Mike was thinking it was picture perfect, the villa was secluded from all the other villas and it had a private dipping pool, hot tub and their own access to the beach. Mike's jaw dropped as he walked inside the villa and Lucy started getting very excited! The inside of the villa was decorated in a very feminine decor. In fact it was almost too much. The entire villa was painted in various shades of pink. All of the rooms were ultra girlie with pink glitter walls, fabrics and curtains. The bedroom had a four poster bed with a pink and white netting draped over the top and cascading down the sides. There was a makeup table and tufted bench in one corner of the bedroom and a full length mirror in the other corner. Lucy was jumping up and down with excitement and Mike was a bit apprehensive.

"I can't believe the airline lost my luggage, what the hell am I going to do?"

Lucy calmly replied, "Look Mike, you're fine. The clothes will show up and in the meantime, the property manager told me there where cloths in the closet and the dresser. She said to make ourselves at home and use whatever we wanted to."

Mike opened up the closet and start checking out all the clothing options. Much to his horror, all of the clothing was female. All of the hanging items were slinky dresses, fancy dresses, blouses and skirts. The closet was huge, there was an entire wall dedicated to shoes, all of them female shoes, mostly high heels.  He went over to the tall chest of drawers in the bedroom and again, everything in the dresser was feminine. All fo the drawers were full of panties, bras, stockings, garter belts and other lingerie.

"What the hell am I supposed to wear! Everything in here is girlie," exclaimed Mike. 

"Well," Lucy answered, "You are fine in what you have on for dinner." Lucy toyed with him a bit and pulled out a pink satin nightie from the closet, "But, I want you to wear this tonight."

"No way!" Mike snapped back, although he felt a twinge of excitement at the thought of wearing a nightie. He had no idea of why he felt this way but he was instantly reminded of his nightly dreams. In the back of his mind Mike was thinking that it wouldn't be so bad if he had to wear that.

Lucy just giggled and whispered under her breath, "yeah, we'll see about that."

At dinner, the resort manager came up to Mike and Lucy to greet them. She was a stunning tall blonde with hardly any body fat. "Hello Mike & Lucy, my name is Rebecca and I am your resort manager. It is a pleasure to have you staying with us. I trust you will find everything here extremely delightful and relaxing."

"Please, let us know if there is anything that can do to make your stay here the best that it can be. And, here are two pills. One for you Mike and one for you Lucy. These pills are a type of vaccination to prevent sickness from the Virgin Gorda beach flies. I encourage you both to take them right now, I wouldn't want your vacation to ruined with sickness. I must be going now, have a great dinner!"

As Rebecca turned and walked away from their table, Mike whispered, "Wow, what a body." Lucy kicked him under the table, "Really, Is that all that you can think about? Take your pill, I don't want to you get sick and miss out on all the other hot bodies that are here!" Lucy sarcastically snapped. 

What Mike didn't know is that Lucy had secretly arranged for this entire vacation and all of the events that have transpired up until now. Yes, she had the luggage "conveniently" lost and yes, she had made arrangements for the villa to be 1,000% feminine! Mike was in for the vacation of his wildest dreams and he didn't even know it.

Mike obediently took his pill, he always took direction from Lucy without arguing back. He didn't noticed that Lucy slipped her pill into her purse. After a few more drinks, the two decided to stroll along the beach and head back to the villa. Mike's body started feeling tingly and his voice was cracking a bit.

"Hey, Lucy, do you feel a bit strange? My body is all tingly" Mike looked over to Lucy as he spoke, realizing that his voice almost sounded like a girl! His eyes were wide open and Mike started to feel a warm sensation in stomach.

"No Mike, I feel just fine. Its probably the drinks you had with dinner. Let's get back to the villa so you can lay down and rest" Lucy replied, but she was thinking to herself, 'wow, the pill is working quickly, I need to get him inside soon'


As soon as they stepped into the villa, Mike started to feel weak in the knees. He stumbled into the bedroom and plopped onto the bed. Within a few seconds he was dead to the world, in a deep sleep. Lucy managed to get his head on the pillow and slip his shoes off. As she was starting to unbutton Mike's shirt, there was a  knocking at the door.

"Who is it?" Lucy yelled.

"Its me, Rebecca, I wanted to check in on you."

"Come on in, Becca. I need your help," replied Lucy.

As Rebecca entered the bedroom, Lucy said, "Oh my God, that pill worked so fast! We barely made it home." Lucy continued to unbutton and remove Mike's shirt. She then started to remove his shorts and underwear.

Rebecca giggled, "Yes, I gave you fair warning though! And wait until you see what happens over night! You'll be amazed by the time he, I mean she, wakes up tomorrow. See, look at her chest, all the hair is already gone! By the way, what is her name going to be?"

Lucy had thought long and hard about that already and without missing a beat she answered, "Lindsey"

"Oh, Lindsey is such a girlie name, how did you come up with that?"

"Well, Mike, I mean Lindsey doesn't know it, but back at home she kept having dreams that every night and before she'd wake up, she was talking in her sleep. I heard it every night and knew that she was dreaming of being Lindsey! So I decided, we may as well make her dreams come true! Here, help me get Lindsey into her nightie, I picked this satin pink one for her to wear tonight."

The two women managed to get Lindsey into the nightie and tucked in bed. Then they went into the kitchen and shared a bottle of wine while they planned out the rest of Lindsey & Lucy's vacation.

Around 11:30am the next morning, Lindsey started to waked up. Lucy was already up and had coffee made. She peeked into the bedroom, "Come on sleepy head, time to rise and shine. Lets go sweetie, its such a beautiful day, I don't want to waste it by staying inside all day!"

Lindsey was wide awake at this point and horrified! "What the fuck! Why am I in this nightie!" Her voice was higher pitched than yesterday "What happened to my voice?" She started trembling in bed. Her body was smooth all over and she had breasts. "What the hell is going on? I'm a fucking girl!?!" 

Lucy bounced into the bedroom giggling, "Yes sweetie, isn't it great? Get out of bed and lets take a look! Oh my God, look at your hair, its as long as mine and your body is so smooth, no more body hair!"

Lindsey slipped out of bed and her nightie fell down to mid-thigh. As she stood up, she caught a glimpse of herself in the full length mirror and was shocked by the sight. Sure enough, there was a stunning hot blonde woman staring back at her in the mirror. Lindsey started to cry.

Lucy came over to her, "Its okay dear, no need to cry"

"I'm not crying because I'm sad, honey, I don't know why I'm crying. I can't help it. I'm shocked by all of this. How did it happen? I... I just don't... I feel so good! Its amazing" Lindsey sobbed.

Lindsey was confused, she had a million thoughts running through her head... How could this be?... I've been dreaming of this for last couple of months... I even started wearing some of Lucy's panties, I can't believe that I turned into a beautiful lady. Lindsey went back to the bed and sat on the edge holding her face in her hands sobbing uncontrollably.  

Lucy came to her side and said, "Its okay sweetie, I knew for the past couple months about Lindsey."

Lindsey lifted her head out of her hands and looks at Lucy, "But, how?"

"Honey, you talk in your sleep!" she giggled.

Blushing, Lindsey felt embarrassed. Lucy, wrapped her hand around Lindsey's shoulder and whispered in her ear, "Its okay, I love this!" and she starting kissing Lindsey's neck and caressing her newly developed breasts. Their lips met and they started kissing passionately, each others tongues darting in and out of the others mouths. Lindsey's body felt amazing, her nipples were getting very hard and she was getting wet between her legs. Her pussy lips began to swell and she had an urge & desire to make love deep in her belly.

The two ladies got naked and continued kissing and caressing each other in bed. Lindsey started to move down Lucy's body, kissing her nipples and then her belly but Lucy stopped her. "No, honey, you always go down on me. Today, I am going to let you experience what it feels like to be a woman being pleasured." and with that Lucy started to move her lips slowly down Lindsey's neck. Lindsey moved down to Lindsey's right breast, taking her tongue and gently swirling it around Lindsey's nipple and playfully nibbling on it with her teeth.

She then did the same to Lindsey's left breast. It was so erotic, Lindsey was in heaven. Lucy started kissing Lindsey's stomach, moving down to her pleasure box. Lucy was in a playful mood, she started kissing Lindsey's inner thigh on one leg and then the other leg, inching up to Lindsey's pussy. Then, she took her tongue and started licking Lindsey's clitoris, moving her tongue around Lindsey's clit. Lindsey started moaning, she had never felt like this before. I was pure ecstasy.

Lucy started to finger Lindsey, sliding two fingers into her pussy as she continued to nibble and lick her clit. Lindsey's body started to tremor and she felt a warm sensation coming over her. Waves of warmness rolled over her and Lindsey moaned in pure pleasure, her eyes rolling back into her head as she let her body succumb to the joy. Lindsey had just experienced her first orgasm as a woman and it certainly was not going to be the last of this vacation. She was perfectly content with laying in bed the rest of the day and continuing to explore her new body but Lucy said, "Okay, enough playtime, lets get dressed and go out, it's such a wonderful day!"

Panic stricken, Lindsey gasped, "Hell, Lucy! I can't go out in public like a girl!"

"Why not, honey? You ARE a girl! And a great looking one at that. What are you planning on doing, staying in this villa for the rest of your life? Now, you know better, that can't happen!" Lucy teased Lindsey, winking at her as she was talking.

"Welllll, I... I guess not. I suppose you're right. But what am I going to wear?"

"Sweetie! There is an entire closet full of clothes! But don't you worry, for today, we're going to the beach and all you need is a bikini! I have the perfect one for you right here." as Lucy was talking she walked over to the dresser and pulled out a skimpy, sexy, black, crochet bikini. It was the kind that had a scrunch butt and tied on the sides at the hip.

"I can't wear THAT!" Lindsey gasped, "It is sooo tiny!"

"Welcome to being a girl, honey!" Lucy laughed, "Its okay, you'll get used to it and you'll love it!"

Surprisingly, Lindsey was able to put on the bikini all by herself. She figured it was all of the experience of taking bikinis off other women that gave her the skills to being able to dress herself. She looked in the mirror and said, "Damn, if I was Mike looking at me, I'd give myself a boner!" and she giggled at how absurd that sounded. 

Lucy was in the bathroom chuckling to herself as she overheard Lindsey. "Sweetie, come in here so we can do your makeup"

"But why do we need makeup?" protested Lindsey. "We're going to the beach"

"Exactly, honey! We want to look great for all the hot men out there, don't we?" Lucy responded. It was then that Lindsey fully understood that she was indeed a woman and that she had the same urges and desires that any other woman had! Lindsey wanted to look her best for another guy!

Lindsey stepped into the bathroom, prepared for what was about to happen next. Lucy said, "okay, dear, sit down so we can apply some makeup. We're not going to put too much on since we just doing the beach right now. we don't want to be too over the top!"

"Now, we're going to start by applying some foundation to your face and some blush to bring out the color. We'll also add eye shadow to your eye lids. Pay attention honey because you'll need to learn how to do this for yourself soon! Next we'll apply some eye liner and mascara, that'll make your big blue eyes pop! Finally, we'll finish off with some lip stick and gloss." When Lucy finished and stepped away, Lindsey saw a gorgeous female face staring back at her through the mirror. She was so excited at how amazing she looked that she forgot about the skimpy bikini. Lindsey jumped out of the seat and hugged Lucy, "Oh thank you sooo much! That is just so wonderful!"

The two ladies packed up a few beach towels, wrapped sarongs around their waists and headed down the the beach. As they were walking, Lindsey started to really swing her hips and walk more like a lady than a man. She didn't even need prompting from Lucy, Lindsey was totally getting into it. Lucy just giggled to herself thinking that it was so cute.

The beach was practically empty, it was truly paradise. They laid out their towels and lathered each other up with sun screen. Then they laid down on their backs, starting to enjoy the warm sun, gentle Caribbean breeze and the sound of the waves crashing on the beach. After a while they both turned over to start sun tanning their backs. Lucy reached over to Lindsey and untied her binik top. Lindsey gasped, "Honey, what are you doing?"

"You don't want to get a sun tan line on your back dear. Relax, its totally ok. Look, I'm doing the same thing!" and with that Lindsey said okay and rested her head on the towel. The two girls were drifting off into a light sleep when two handsome looking men walked over and said hello.

"Hi ladies, Do you mind if we put our towels down next to you two and enjoy this lovely beach together?" asked the taller of the two men. He was about 6'1", probably 190 pounds and looked like he went to the gym every single day. He had a ripped six pack, brown hair and hazel eyes. "by the way, my name is Josh and this is my buddy Ryan"

Ryan was a bit shorter, blonde haired, blue eyed and equally as fit. Both men looked like they could be models in GQ.

"Sure," Lucy answered, "We'd love some company, isn't that right Lindsey?"

Simultaneously, Lindsey was getting up from laying down, forgetting about her bikini top. She still was not 100% accustomed to being a girl and all of the little details that she took for granted as a guy. Remembering to re-tie her bikini top was one of those forgotten details. Her perky breasts were exposed for all to see. Once she realized, she tried to cover up her boobs. Lucy erupted in a howl, laughing uncontrollably while she helped Lindsey cover up.

Ryan chimed in, "It ok honey, you have lovely breasts, don't worry about covering up just for us, we don't mind!" he was sort of giggling as he completed the statement. All four of them broke out into laughter and started talking. They all had a great time hanging out on the beach that afternoon.

Coming up soon... part II
email the author for questions, amberlewiscd@gmail.com