Magic Man - Hotel Encounter

Story Info
A chance meeting on a business trip leads to new things.
2.7k words
4.25
9.8k
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is the first part of a long-form story. It's my first ever story so please give me any feedback for editing the other parts! All characters and places are fictional.

"Here is your room key, Mr. Carson. The mini-bar in your room is gratis with the rewards points you used. The Public House bar and restaurant are open until midnight tonight. If you need anything at all please call." The lady behind the counter gave him a polite smile as she handed over the card holder.

"Thank you so much", said Andrew as he took the proffered cards. Turning from the check-in desk, Andrew walked towards the elevators. It had been a long month on the road, but a successful one. Having stayed in motels of varying quality (though none being great), he has asked his VP if it would be alright to splurge for his last stop. He could already tell it was worth asking, this place was far and above anything he was used to.

The 'ding' of the elevator brought him out of his reverie and he started to step inside when he noticed a woman walking out. He nonchalantly looked her over as she minced over towards the 'Public House' in 4-inch heels, a modest blouse and skirt combo. There was something off about her though....

Maybe also traveling for business he thought as she walked away. The sound of the closing elevator doors forced him to look away and catch them. He dragged his suitcase inside, thinking maybe that bar and restaurant was worth a look tonight. Pushing open the door to his room, he was met by a large, well-appointed room with a full-foam king bed, and sitting area with a couch and tv. He was very happy to live here on the company dime for a few nights before he could return home for a well-deserved stint of being off the road.

As a field service tech for a large company, it was his job to routinely visit all the customers in his area of responsibility 3 times a year for repairs and updates. Being on the road so often and for so long had precluded having a family, among other things, he thought as he changed out of his travel clothes and stepped into the shower. The hot water washed away the stiffness of sitting in a car for 10 hours and brought back to mind the woman from the lobby. "I think a visit to 'Public House' is just what I need after today", he said as he toweled himself off. One small touch, he thought as he willed a small amount of scent into his hand, which he deftly rubbed into his neck and chest. Not enough to cause any problems, but enough to give him some help in finding company tonight. He dressed business casual to match the woman's outfit with a French blue shirt, slacks, and casual shoes.

Arriving back at the first floor, he walked smoothly over to the Public House entrance and gave the room a once-over. Andrew spotted the woman sitting at the end of the bar with a cocktail playing with her cellphone. Definitely not what she appears, he thought watching her furtively look around. He closed his eyes and breathed out slow, allowing his inner eye to awaken. Her aura burned with a bright pink flame, just a tinge of blue in the center.

Bingo, time to work.

He walked to the bar and sat a few stools away, and ordered a beer. As he sipped at the beer, he glanced over and examined the pedestrian makeup, modest chest, and slightly messy hair. The crossdresser looked up from their phone and noticed his gaze, quickly looking away and taking a nervous drink from their cocktail. Andrew looked back to his beer, and whatever was playing on the bar television.

He finished his first beer, and looked over to assess the CDs drink. Empty, he thought as he flagged down the bartender. He ordered another beer for himself and another of whatever she was drinking. She looked up from her phone as the bartender brought her drink and pointed over to Andrew, who took the cue to give a friendly wave.

The CD said "thank you" in a soft tone that Andrew could barely hear over the bar noise. He picked up his beer and walked over to her.

"Do you mind if I sit down?" he asked pointing to the stool next to hers

"If you want" she replied quietly.

He sat down, taking another sip of beer and turned to her. "Hello, my name is Andrew" he said. "I'm here traveling for work. I saw you in the lobby and thought maybe you were also here on business."

"My name is Julia. I'm traveling but not for work" she replied. Her voice sounded odd but he couldn't immediately place what was different about it. They chatted back and forth for a while as they finished their drinks. He watched as she nervously brushed at her hair, There it is!.

As she stroked the long blonde hair, he saw her wig slip just a bit, but enough to expose the truth that she was trying to conceal. Good work, he thought as he smiled back at her, fairly good at passing, but far from perfect. He had seen better but the CD in front of him had a nice base to work from. Short enough for heels, thin enough to wear most women's clothes, some experience with makeup but the wig was a big issue.

He had not been expecting to run into an opportunity like this during a work trip but here it was looking nervously at him as he looked back. He made his move.

"You're good", he said under his breath, bringing himself closer, allowing his scent to come into play. "But I think you could improve, and I can help."

She stared back at him in utter shock, and turned away as if to run, but was struck by something which held her in place. A calming sensation washed over her as she looked back at him.

"It's quite alright", he said calmly, gazing into her eyes. "I can imagine this is one of your first few times going out fully dressed?"

She could only nod her head.

"Well a bar doesn't seem the right place to talk. Why don't you come to my room? There's a place for us to sit, and I promise you nothing will happen that you don't want to."

She hesitated, and he could see the battle happening behind her eyes. But these kinds of things needed to be decided by them, and he simply sat back and sipped his beer while he waited.

"W-We're only going to talk?" she whispered back clearly nervous.

"If that's what you want, yes", he replied looking back at her. Got her.

"Alright, I'll go with you". He stood and offered a hand to help her off the high stool.

They walked out of Public House together. He took a measured pace, not wanting her to struggle in heels she clearly hadn't practiced enough in before making this outing. At the door to his room, he paused, looking back at her. She was nervous, but seemed to have decided this is what she wanted to do. He opened the door.

"Please, have a seat. Would you like some water, or maybe something stronger?" he gestured tothe mini bar.

"Just water for now", she said, taking a lady-like seat on the couch. Andrew grabbed a water bottle from the fridge and sat down at the other end, giving her space.

"You have lovely taste in clothing, I was particularly taken by those heels. How long have you been dressing?"

She shifted and re-crossed her hose-clad legs. "Since I was 15, so almost 10 years now."

"So your desire to go out in full 'girl-mode' has been a recent development I take it?"

"Yes." she seemed to be relaxing just slightly, telling your story to someone always seemed to have a calming effect with his charges. "After college and living on my own, I just realized that I wanted to be who I wanted to be, so I've been slowly building a wardrobe and working on makeup as much as I can.

"If you could be a woman for real, would you?" At the question she snapped her head to look at him as if he were making a joke. When he remained serious, she seemed to slump a little.

"Well yes, but I'm already 24, and I don't have the kind of money it would take to be what I truly wanted to be."

"And what is that?" Andrew asked, moving himself over to sit directly next to her.

"Well...beautiful, curvaceous, a bombshell kind of woman that no man can ignore. A woman who is striking and stops conversations when she enters a room. I don't think I could ever be that" Tears were starting to form in her eyes.

He gently clasped her shoulder. "What if I told you I could make that dream a reality? What then?"

She looked up, and saw the incredulity on her face. "Even with all the money and surgery in the world, I don't think that could happen." She took the offered tissue and dabbed at her eyes.

"Well I think it's time I tell you something about me, something only very few people know. I have powers, powers that can help you become the woman you dream of." He held up a hand as she started to stand up. "Wait, I know this sounds unbelievable, but I can show you the woman you desire."

"How?" Julia crossed her arms, still standing.

"Please sit", he patted the couch. With great reluctance, she sat down again. "I'm going to hold your hand, and I'm going to place my right hand on top of your head. You're going to feel dizzy at first, but then you'll see her, I promise."

She offered her hand. He clasped it in his left, feeling for her heartline. He gently placed his right hand on her head and closed his eyes. He emptied his mind for a moment as he felt her connect to him. Then he pictured Julia as she dreamed, a cascade of brown hair, gorgeous face with perfect lips and nose, high cheekbones, feminine neck, strong shoulders, large firm breasts, a trim waist. He continued with her hips, firm ass, strong thighs and tight calves down to perfectly proportioned feet complete with bright red painted nails. Now that she was formed, he flashed images of office wear, dresses, yoga pants, all making her appear as if she was a goddess come to Earth. He emptied his mind again as he severed the connection with her heartline.

"Well?" He asked, sitting back and rubbing his temples.

"How did you do that?" She asked, staring at him intently. "No one except me knows that dream. What are you?"

"As I said, I have powers, powers which can let you become the woman you just saw. Your heart burns with a great desire to be her, I can read your desires through your heartline, and I can show them to you with that connection. I wish I had a better explanation myself", Andrew shrugged. "So, now will you hear me out?"

Julia grabbed his hands in hers, "Please tell me what I need to do". She looked as if nothing could sway her from this decision.

Now for the interesting part.

"Well, it takes four sessions to become the woman you desire to be..." Andrew started, waiting to see if she would interrupt. When she didn't, he continued. "In order for you to truly become Julia, I need to fuck you three times."

She pulled back, letting go of his hands. "You need to FUCK me?! What the fuck! And why three times?! Are you some kind of pervert?!"

Andrew made a warding gesture, trying to calm her down. "Yes, I do need to fuck you. My seed has the power to transform your body, but the sex needs to be consensual. We need to connect similarly to how we did just now in order to form your body to your desires. But it can't happen all at once. Two times will make you the woman you desire to be, but that effect is temporary. It won't be until I fuck your new vagina that the effect becomes permanent."

"So your cum will make me a woman? How do I know you're not some faker just looking to fuck some poor crossdresser and move on?" She sat back, clearly not fully committed to the idea.

"Yes, and you'll see changes after the first time. Your aura is ready to accept a new identity, and as I showed you earlier, I have a clear vision for what your desired outcome is. You don't need to decide now, but I'll only be in town for seven more days before I need to go home."

"Why are you doing this? Why would you want to help some random crossdresser you happened to find at a hotel?" She seemed to be coming around to the idea that Julia could be her new reality.

"It's a long story, but someone gave me these powers a long time ago and it was up to me to help people like you or not. To date I've helped six people become the women they dreamed of, you could be number seven if you so choose." He took a long drink from the water bottle as he watched her decide.

"I want to do it," she said, her voice unwavering.

"Ok, we can start tomorrow evening. I need you to do a few things over the next three days: 1) prepare yourself for sex, however you want or need to. That includes bringing whatever lingerie or other things you need to feel feminine 2) You need to make sure you have time to recover. The changes your body will go through aren't without some pain, and you will not want to be going to work while they happen. And finally 3) envision Julia perfectly to include what size her clothes will be. Once you change anything you own will not fit your new body, so having clothes sized for your dream woman will make things much easier on you. Does all of that make sense?"

She nodded, clearly dismayed that the process couldn't start immediately. "Here is my room key," said Andrew, proffering one of the cards. "I have my actual job tomorrow and you can use the room to prepare yourself before I return, around 6pm. Do you have any questions?"

"Yes," She said. "How..uh, big are you? I've only used smaller toys and I'm..." She trailed off.

"Well I'm about 8 solid inches, but don't be afraid. Once we establish our connection you won't be worried about pain.." He smiled and winked at her. "Yet another of my powers".

She turned and gave him a quick kiss, "Thank you" she said. She stood up and walked to the door. "I guess I'll see you tomorrow", she said as she pulled it open.

"Get some rest, you're going to need all your strength". Andrew said, waving goodbye. As the door closed he stood up and stretched. He was going to need extra sleep tonight, and a lot of patience to get through the day tomorrow. His cock swelled at the thought of another sweet, tight ass.

Calm down, I need you tomorrow, not tonight you big oaf.

Sleep took him quickly. He awoke prepared to conquer work and a virgin ass. He was barely able to focus on work, and the hours seemed to crawl by at a snail's pace

I'm sure it's the same for her, he thought as he tapped away at his workstation keyboard. Luckily this client's admins actually knew what they were doing, so things were much easier for Andrew. When 5pm arrived he packed up and nearly ran out the door to his car.

The hour-long commute back from the data center gave him much needed to time re-enter himself and focus on the task ahead. By the time he arrived back at the hotel he knew he was ready.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
Mermaidlover1960Mermaidlover19607 months ago

Loved this storyline!! Please write at least one more chapter.

AnonymousAnonymousover 1 year ago

Great start. Well written

Please continue writing

BrendaNWBrendaNWover 2 years ago

Very creative and well written .. I think that he could have a new full time job if he wanted it .. and had the strength .. one lady a week who would become the woman of her dreams .. he would be very popular :)

missrhondamissrhondaover 2 years ago

Can't wait for you to take us further with this story. Great start.

Show More
Share this Story

Similar Stories

An Ex-Boyfriend's Punishment A girly ex learns a lesson from a more experienced sissy.in Transgender & Crossdressers
Feminized by Cum Pt. 01 After losing a bet a young man gets hooked on cum.in Transgender & Crossdressers
Falling Under Mommy's Spell Pt. 01 A cross dresser and his mother discover their secret sides.in Transgender & Crossdressers
The Cabin Ch. 01 I stumble upon a cabin containing more than I anticipated.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
More Stories