Let the Spirit Lead Ch. 02

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Andrea becomes part of the strange hotel.
15.3k words
4.81
8.5k
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Part 2 of the 2 part series

Updated 06/09/2023
Created 06/05/2019
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Picking up from the first chapter: We find Andrew, a hidden cross dresser going by the name Andrea, in a special hotel that offers condom-less sex-workers offering their services. Alexis, her new guide to his new world, just left the shower with Andrea and has a plan.

"You're going to need some work though if this is going to work. I'll be right back." Alexis said.

She finished toweling off and put on her clothes tossing her now used and soiled panties and bra into the purse. Once dressed, she picked up the black strap-on and walked back into the bathroom. Andrea could hear the sink running and assumed she was washing and sanitizing the monster that had pummeled her ass a short while ago. Walking back into the bedroom area, Alexis looked around ensuring she had all her things and made for the door out of the room. Before she crossed the threshold, she stopped and looked back at Andrea.

"Pick out something slutty. I'm sure you have plenty. Do you own any dresses or clothing?"

Andrea nodded.

"Shoes?"

She nodded again.

"Good, pick out some options for me to choose from. You and I are going out tonight."

Andrea's heartrate picked up again. She had no concept of what Alexis had in mind, but it involved the two of them going out into public, Andrew dressed as Andrea. Fuck.

"Do you own a wig?"

"I don't", Andrea said.

"Okay, let me handle that. Our little establishment has options considering what services we provide. I'll find something perfect."

And with that, she closed the door behind her and left Andrea there alone in her room, her thoughts and mind reeling from the ordeal she just experienced and profoundly nervous of what was to come.

Some while later, a knock on her door. It was Alexis returning from wherever she had gone.

In her time alone, Andrea had gone down to the van in the parking lot, dressed as Andrew of course, and brought up all of her secret collection stored in the boxes of what was Andrew's attic above the garage. On the bed, which she had also made up, she had laid out several outfit options she owned and considered slutty enough to serve whatever intentions were in store for her to come. The first was an off-white, almost cream-colored, ribbed sweater dress which clung tightly to her body and exaggerated her curves, including whatever sized boobs she chose to wear. The second was a well cut light pink silk dress transparent enough to reveal the details of whatever lingerie worn beneath it. The third option was a black, high-spandex content dress that hugged curves and accentuated a woman's assets. The final and fourth option was a dark grey pencil skirt and white satin blouse which had a feminine bow that tied around the collar. Whatever option Alexis chose, Andrea of course, had the necessary lingerie to go with it. She did have an excellent collection and she was always prepared. Andrew had great taste that suited her sense of style like they were the same person.

Alexis set down the bags she was carrying and admired the outfits laid out on the bed. Being the submissive that she was, Andrea had made her a drink and offered it to her when her hands were free of the baggage she had brought. She immediately drank half the glass in the first gulp and then thanked for her the offering. Looking at the bed again, you could almost see the wheels in her mind spinning, making decisions. Alexis glanced at Andrea again eyeing her up from head to toe and then again at the bed.

"Okay, I think I have it." Setting the remnants of the cocktail down again Alexis picked up one of the bags and started walking to the bathroom. "Follow me slut."

Andrea obediently did as commanded.

Alexis had changed her clothes while she was gone and was now wearing a black dress. Every woman owns a little black dress or three and this one was exquisite. It hugged her curves perfectly and was more than likely expensive. She had also reapplied her makeup and fixed her hair. Her stocking clad legs and feet made almost no noise as she crossed the short distance from where she had set the drink down to the bathroom and she turned on the tub again. With the water running to fill up the tub, she squirted some soap from a bottle into the water and Andrea watched as the bubbles immediately formed and the scent became evident as very clearly, girl.

"Take of you clothes and get in." Alexis demanded, although without being harsh in her tone.

Again, Andrea submissively complied.

"Shave your facial hair off and check your body for anything you may have missed. I see this is something not unknown to you. Shave off everything. And hurry."

Andrew had kept facial hair for as long as he could remember and with it now gone, he felt more naked than he had in as long as he could recall. It felt odd. His face had always been somewhat of a baby face. Despite that, his six foot frame and moderately muscular features still screamed male. He knew this of course which is the predominate reason he never attempted to pass in public. Well, that and fear.

Once freshly shaven and out of the tub, Andrea toweled off. She felt like a child somewhat being bossed around by a mother. It was a somewhat natural feeling for her considering her childhood and she easily fell back into the roll just as a woman now which seemed to even further accentuate the submissiveness. This kind of mimicked the story of her life. Andrew was a leader at work, a partner in a successful company and people had a healthy fear of him as a boss, but somewhat secretly he was a softy. He struggled to fire people unless they truly deserved it. His ex-wife would often boss him around until he had too much and would fight back and then she would subsequently back down. Eb and flow. Back and forth. Like fucking. Strong and weak. With Alexis, everything was different so far. Andrea was just weak. From the moment Alexis jumped on her and smothered her face with her cum filled pussy—she just gave in. Andrew let Andrea lead now and gave in and submitted and was happy to do so.

"Hey, fuck meat. You with me?"

"Sorry, heads just kind of spinning right now."

"Look, I have plans for you. I have a strong belief you'll love this and so will we."

"We?" Andrea asked.

"Yeah, there's about eight other girls here that all do the same kind of work. You're gonna be our little bitch tonight. Trust me. You don't like this, you let me know."

It made sense now. The woman she had seen earlier rushing past the door as Alexis was leaving was another of the prostitutes working in this strange hotel "above the fifth floor".

"Sit down at the desk."

Pulling out the chair from the desk, Andrea sat down, staring at her reflection in the mirror. It was odd seeing Andrew without the facial hair he had worn for so long.

"Okay, I picked this out for you while I was gone."

Reaching into the bag on the floor next to the desk, Alexis pulled out a reddish, long wig.

"You're beard was kinda red and I can tell your pubes were probably red, so I figured this was perfect."

She was correct. The facial hair was indeed red and when she actually wasn't clean shaven down there, it was also red. The colors weren't identical but they were close. Positioning the wig onto Andrea's head and straightening it, Alexis moved it into place. Using hair pins, she secured it ensuring the thing wouldn't move during whatever events they found themselves in tonight. Alexis reached down into the bag again and pulled out a brush and proceeded to fine tune the style of the wig to make it look as real as possible. This wasn't a cheap wig and it looked about as real as Andrea could ever guess a wig would look like. Having never worn one besides cheap things for Halloween, it looked completely natural and real. Andrea finally had hair!

"That looks fantastic. Make-up time."

Andrea figured this was coming but couldn't imagine what she could do to make this thirty-something male look anything like a passable female.

Just then, the door knocked again and Alexis took one step towards it and opened the door to the room. In walked a gorgeous black female.

"Hi there, I'm Emma. How are you?"

"Ugh" Andrea stammered as Emma caught her staring at her breasts. "I'm Andrew. Ugh, I mean Andrea. Fuck. I'm both."

"Yeah, Alexis mentioned you. Said you two got up to some freaky shit tonight. I've only ever fucked one other person in the ass before. It was fun as hell."

Andrea's face reddened. She had never shown Andrea to anyone before tonight, now people would know her and her perverted proclivities. Making it worse, Andrea was apparently a topic of conversation among the women working here.

"Ugh...yeah." Was all Andrea could muster to squeak out.

"Well, let's get started." Emma said.

"She's super easy. Does whatever I ask." Alexis added.

Setting her own bag down, Emma undid the buttons on her dress and let the soft fabric of her dress fall to the floor. Standing there, Andrea was quite sure the eyes in her head bugged out of their sockets as she took in the sight of this woman.

White, high-heeled patent leather shoes. White stockings going up to her thighs, held up by thick white straps attached to a very pretty and very vintage looking garter belt. As Andrea's eyes moved up her body, she noticed something out of place. She was pregnant! The top of the garter belt was bowed out around the clearly blossoming tummy of her baby bump. She guessed she was about five months along judging by the size. Emma reflexively, like all women, placed her hand subconsciously, and protectively, over her belly. Her belly button had been pushed out from its natural inner position and was sticking proudly outwards from the growingly restricted space inside her womb. Her bra was also white and was also quite vintage in its styling. Thick, wide straps holding up full-coverage cups. Andrea could see from the hooks below her shoulders but above her boobs that it was a nursing bra. Andrea's erection was immediately pronounced and pushing against the fabric of her shorts.

Aware of her staring, Emma said: "Alexis said you would be fan. Was she right?"

Andrea couldn't even speak. Her mouth had gone dry. She picked up the cocktail she had made for myself and took a drink. "You look gorgeous."

"Thank you." Emma more smiled than said. "Let's get started. Our clients are waiting. And drinking. We shouldn't take too much time. Clients can get rough when they drink too much. These guys are younger, so..."

Moving chairs from the other side of the room closer, Emma and Alexis sat down and laid out the makeup they planned to use on the desk in front of me.

"Turn your chair around so we can do this as fast as possible."

Andrea complied and closed my eyes. This was a surreal experience. Perhaps twenty minutes later, the two attractive sex workers almost said in unison: "Take a look."

Andrea stood up from the chair and turned around to look at herself in the mirror. Being taller than both of these ladies, wearing shorts and a t-shirt and with only limited time, it wasn't some movie level transformation. But it was stunning nevertheless. Andrea was being realized. Her long, red hair flowed down over her shoulders and behind her back. Her face was softened considerably and definitely appeared feminine. The effects of the cocktail she was drinking weren't full realized, but in the right lighting, or lack thereof, and of course sitting down, Andrea at least from the neck up would surely pass in public.

The girls squealed in delight discerning from her reaction that Andrea admired their workmanship. Work-woman-ship?

"Okay, take your clothes off girl." Said Alexis.

Andrea didn't hear her at first. She was mesmerized by the woman looking back in her in the mirror. A woman's face and head but with the tall and somewhat muscular physique of a man. Snapping back to reality she stared down at her body and pulled off the clothes she had on.

"I want you to wear this one." Alexis said. "Oooh, me too. That's hot as fuck." Said Emma.

"This is what I planned to wear underneath. Is this sexy enough?" Andrea asked.

Considering the options in her mind, Emma said; "That's perfect."

"Yep, that'll do sissy." Said Alexis.

Careful not to smudge makeup or misalign the wig, Andrea began the task she had become quite proficient at of putting on the lingerie and garments that enflamed the sissy, slutty urges. The black thigh-highs were usually the first thing she put on when dressing. But she opted for the bra and forms first tonight.

"Which ones?" Andrea asked.

"These." Emma pointed to the large ones. The second smallest of the four options, they were probably the most realistic ones for Andrea's size and frame. Large but not comically large and they would fill out the blouse well enough but not portray the pornstar she often presented as in private.

Andrea had chosen the perfect bra for this outfit. The Playtex 18-hour bra was older, purchased like most of her lingerie through ebay as she could never face a store clerk in public buying things for herself. It had a very prominent bullet shape which she loved and it was black, a little too tight and held her forms in place without them moving too much. She often chose this type of bra to sleep in when traveling because when she woke in the morning, her silicone tits barely moved. She could roll out of bed and she had boobs like a real woman. The materials were nylon, satin and lace—what could be better?

Reaching into one of the smaller boxes from the van, Emma picked up something else that was black. "You'll want this probably." Handing Andrea the butt plug, the new redhead meekly smiled and held it in her hand. Embarrassed, her hand dropped to her side in an attempt to hide the short device. "This too."

The tube of lube destroying any modesty Andrea had left as well as pretense where tonight could lead.

"Come on! Hurry up, we don't have all night! You want us to do it? Asked Alexis.

"Yeah, that sounds fun. Bend over sissy." Said Emma.

Andrea did what she was told. Placing her hands on the desk, she bent over prepared to have something else shoved up her ass tonight.

"Pull your cheeks apart."

Alexis lubed up the plug and then Andrea's ass and popped it in where it belonged. Andrea didn't even jump. After the anal reaming Alexis had performed on her earlier, the little black plug barely registered on the same scale. Standing up and turning back around, Andrea continued with her work.

The panties were cute but high-cut, but she had chosen them for a reason. She wanted to protect her ass from some kind of unknown invasion these women had in store, but the girdle panties also had built in pads at the butt and in the hips to give more of a female shape.

"Stop. What's that?"

"What's what?" Andrea asked.

"My God, you really are a sissy. Is that a pad in your panties?"

Andrea said nothing.

"This guy really does wanna be a woman."

"I told you!" Said Alexis.

"Okay baby, nice pad. You're thinking ahead. We use those all the time."

Andrea's interest peaked, she said: "You do? What for?"

"This is an optional condom joint. Most men don't. That shit's gotta go somewhere. Running from room to room servicing clients means you often don't have time to clean up. The pad does that for you. Most girls here have a preference, so the hotel keeps all of them in stock. Holy hell, you're already a natural. That's strange."

Emma didn't mean to be cruel with the word strange. She didn't have to apologize to the man in woman's clothing before her. His submissive and happy-to-please-you attitude would tolerate a lot before it truly affected him. But she did anyways not fully understanding Andrea's psyche.

"Come on people, we have to hurry." Said Alexis breaking the pause in wardrobe.

Andrea stepped one leg into the panties and then stopped. Realizing her mistake, she peeled them off and sat down on the bed and reached for the stockings. While she couldn't remember the brand, the stockings were quality and durable. The lace tops were fine and very detailed. Once they were in place, Andrea reached for the garter and pulled it up to her waist. And, like a million times before and with clearly experienced hands, she fastened the straps of the garter to the stockings. Turning around to reach for the panties, her very erect penis swung left and right for all to see. She picked the panties up, looked inside to ensure the pad was stuck appropriately inside and again stepped her first leg and then her second into the garment. Pulling up, she situated them on top of the garter and secured her cock inside them as best she could. Experience taught her, in time, her little clit would relax and she could tuck it between her legs. Much like the submissive person she could be.

Lingerie done, Andrea looked from one face to the other of the women watching her get dressed.

"Very nice." They both said.

Shoes! She thought. She reached into one of the boxes on the floor and pulled out the black ballet flats. No heel. Not when you're six foot. It had taken her hours to make sure her male to female size comparison was accurate before she purchased a pair. They fit perfectly.

Turning around, she picked up the blouse from the bed and pulled it over her shoulders. Situating it on her frame, she quickly did up the buttons and tied the bow around her neck. Looking into the mirror again, she ensured it was done properly and that you could see the black bra beneath the white top. Sure enough. No self-respecting woman would dress this way. Perfect. Nice and slutty. Her large breasts were pointy enough without being silly. She played with the hair of the wig to get it just right in her mind. Andrea was coming together nicely.

Andrew couldn't believe it. He could hardly see himself anymore. Apart from the height and shape of his face and upper body, he looked the part of a woman. Well, sort of. Mostly anyways.

Pushing down the self-doubt and negativity, Andrea grabbed the grey pencil skirt and hiked it up her legs and over her now shapely hips and butt. Amazing what a good pair of padded panties could do. Turning at the waist and checking out her own ass, she admired the look. No sign of the pad between her legs and no sign of her penis. She turned straight to the mirror and took in the whole picture. Emma and Alexis came up behind her and adjusted a strand of hair here and fixed a wrinkle there. They didn't say anything. They could both tell this was an experience for this person they would never forget. Maybe none of them would ever forget. This man, whose life was a total mess, had fully indulged in his secret pastime and found out he, she, looked pretty damn amazing.

The ladies wouldn't admit it to him, but Andrea probably would never fully pass in public in the light of the day without some serious assistance. But in the dark and with the help of some bachelor party booze, she would do perfect.

"Holy shit, you look fucking amazing." Said Emma as she added some finishing touches no woman would forget. Some clip-on earrings, nothing too big, a ring on her right hand and a bracelet capped off the visage of a real woman. She put her arm around Andrea and said something Andrea would never forget: "You my dear, are a real woman tonight."

"Okay, we gotta go!" Urged Alexis.

"Okay, okay, okay, go! Have fun girls. Since I'm not working, can I hang here and go through your stuff?"

Andrea stopped and looked at her for a moment. Let the spirit lead she thought. "Sure! Have fun." And with that, Alexis and Andrea left the hotel room, leaving the pretty Emma in her underwear and very pregnant to peruse the very, very secret belongings of a person she just met. The thought of it would have sent Andrew into a severe panic, but tonight Andrew was gone. Tonight Andrea just let another woman pick through her closet like sisters or roommates would do.