The Rise of Rachel Price T-Girl Pt. 25

Story Info
Rachel negotiates a new stricter contract with Levant.
5.8k words
4.76
3.3k
9

Part 25 of the 44 part series

Updated 10/09/2023
Created 12/14/2022
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

It was a couple of days after the Italian election. Rachel's friends the artist Peyton Harrington, DJ Brooke Sterling, and the critic Elijah Carter had dropped by from the bay. They were vacationing in Tuscany for the summer and couldn't pass up the opportunity to visit Rachel and Douglas in Venice.

These were truly Rachel's friends from the clubs, and they didn't mind Douglas ignoring them for the day. Peyton had mentioned that the bay was quite dull after Rachel had left, and everyone had sorely missed her. No one knew about the FBI visit, so they assumed it was merely business that kept Rachel away. Levant had assured Rachel that the court cases were underway and it would be years before anything significant happened. It was just tax and accounting stuff, Levant promised her, perfectly normal and nothing to be worried about. Therefore, it was safe for them to return, which he promised they would do soon.

Rachel had managed to spend the day with her dear friends. They had leisurely strolled from one café to another, with Rachel acting as their impromptu guide. It had been a delightful experience on a sunny day in Venice. There was so much to catch up on. Brooke had a new DJ gig coming up in Ibiza and had dyed her signature bangs cyan once again. Peyton, with her long auburn hair and prominent cheekbones, had sold another artwork to a new tech company called Satori. Elijah had given some lectures and was working on a new book about contemporary black writers. They exchanged well wishes and updates from everyone back home, including Samantha and Nicky Hilton. Rachel already knew most of the news from Samantha since they regularly chatted on WhatsApp anyway, but it had been a delight to hear it in person.

The trio said how good Rachel looked and how much Italy agreed with her. It might have been one of Rachel's new looks. Or it might have been something to do with the fact that Rachel had just emerged after a particularly raunchy session with Peter that morning. There was something about multiple girl orgasms while being held down by Peter's muscular arms, which had brought a positive glow to her face. Her ass was still buzzing after Peter's pegging, so Peter and ass were hungry for more. She had told Peter no, and he had slunk off to a gym to work out his frustrations.

During a sumptuous lunch at the Vineria all'Amarone, Elijah excused himself from the table, prompting Brooke to lean in. "I've noticed that you've started tweeting more poetry again," she remarked.

"TwitterVerse. It's not really poetry," Rachel admitted. "It's more like a selfie captured in a serenade of syllables."

"I read them, and so does Brooke," Peyton chimed in. "We were saying they sounded like the words of a woman deeply in love."

"Or someone having their brains fucked out of their skull," Rachel thought to herself

.

"It's the city," Rachel explained as she poured more wine. "It's a city of love. Passion, desire, infatuation, and adoration are woven into every brick, every window, and every cobblestone. You can't escape it."

"Levant is such a fortunate man," Peyton remarked.

"You should approach a publisher," Brooke suggested.

Rachel smiled. "You always know how to inspire people, Brooke," she replied sweetly.

"That's a lovely ring," Peyton said, noticing the gold and copper ring Rachel was wearing, "where did you find it?"

"This? " Rachel said, showing the gold and copper ring "Levant flew us for a picnic to the ruins of this palace of Knossos on this massive island called Crete. The ruins are huge and were supposedly a maze, but I think the Asylum is bigger and, frankly, more complicated. Makes you think. You know of thinking that one day people in the future will be having a picnic on the ruins of the Asylum. wondering about us."

Rachel said she didn't mention she had known her way around the palace as its likeness had appeared in Assassin's Creed Odyssey. It had been a wonderful day, and, if anything, deserved a well-earned kiss. then, it did. In the ruins, he had introduced her to the limits of heavy petting. The sun and the warmth were relaxing; her body was screaming for a man's touch, so she didn't resist too hard.

Elijah returned, and the conversation naturally drifted into politics. They couldn't help but analyze the meaning behind the surprising results of the Italian election. They indulged in a lengthy discussion until they rationalized the rise of the far right as the people's response to poor economic conditions. It was a relaxing day, and Rachel managed to put her mother's problems out of her mind temporarily. Engaging conversation and good wine, she decided, can be a temporary escape from the truth, but Rachel realized it was never going to be enough to completely banish it.

******

Later back at the hotel it was the early evening. Solemnly the zombie army of tired tourists had trudged home, leaving the Venetians remaining, and the Ghetto area became tranquil. The familiar sound of waves softly lapping against the building filled the air. Occasionally, boats bumped gently into each other, creating an irregular wooden drum beat.

Rachel stepped out of the shower and began dressing for dinner. Douglas was coming, and she needed to make a good impression. She also had to be attentive and composed for Levant, as per their contract. Peter was assigned to security duty, and she knew his discreet gaze would embrace her, his eyes intimately exploring every inch of her skin.

Meanwhile, back in the Bay, it would be midday, and her mother would be finishing her shift at work. Mom would then come home to care for Grandpa, who had now fully recovered from his hospital stay.

A stranger coming into the hotel room would have been met with a strange sight. A grown woman sitting naked before a long mirror but with a dick, talking down the phone. It was like some living Futanari Manga. Denver had locked the door, Levant didn't like seeing Rachel like this. Denver pulled an old teeshirt on, hiding his breasts. Apart from the manicured eyebrows with hair tied back in a white cotton towel, he looked a little like this old self. His thin spindling legs had grown to quite curvaceous ones. Round hips leading to a narrow waist. Even naked, he looked undeniably feminine now. Denver remembered studying a number of before and after HRT pictures on the internet. He kept thinking that these were all fake. Normal guys before and mostly fetching women after. Hard to believe they were the same people. Yet he was his own evidence, and that was after a year of HRT. If he stayed, there was more to come.

There was one white earbud in Denver's ear, connected to his phone.

"Mom, I heard," Denver said as he dried his long platinum blonde hair with a towel. The sound of the hairdryer would be a dead giveaway.

"Heard what?" Mom replied.

"About you. I get the bills. Why didn't you tell me, Mom?"

There was a pause on the line. "We were all hoping to see you at Thanksgiving. It doesn't feel right, you know, telling someone over the phone. The doctor at the hospital did it in person."

Denver felt tears welling up. He held his head back.

"I'm sorry I didn't have a chance to come back," Denver said.

He walked over to the wardrobe and started searching through a small rack of dresses.

"It's okay," Mom reassured him. "You're doing your part. You're doing so well, my son. You're strong. You're manly. You're the man of the house."

Denver knew he wasn't. He wasn't sure what he was any more.

"Look, I have a chance to extend the contract a bit," Denver said, waving his hands in frustration. He threw the dress onto the bed.

A sigh could be heard on the other end of the phone. "You need to be back here in Tenderloin where you belong. Back with your family. Back with your friends. Butcher is missing you. We all miss you."

Denver sensed an impending argument and decided to avoid it. He took off his T-shirt to reveal his breasts. Standing before the mirror, he admired his perfectly feminine form, perfect except for his genitals. Denver stroked his naked body, searching for any signs of hair. Even his crotch didn't escape the Nair treatment. Denver then found a bra that matched well with the dress and put it on.

"I miss you too, Mom. What did the doctor say?" Denver spoke clearly and loudly as he sat down in front of the makeup mirror.

Mom's voice sounded distant. "They say your grandpa is doing fine. He'll be discharged soon."

"Listen, Mom," Denver said, starting to cleanse his face, "I'm going to accept this new contract. I'll take care of everything."

Mom sounded argumentative. "What new contract?"

Denver continued expertly applying concealer and foundation while explaining, "The people who currently employ me want to extend the contract for a few more months. So, as I said, I've got it covered."

"We don't need a new contract. You should come home," Mom insisted. "We'll manage somehow."

"Look, I know what I'm doing. I'll complete this job, and then I'll be out. I'll earn the money to take care of everyone," Denver said, working down to his neck, smoothing out the foundation.

"You don't have to do that," Mom replied. "You don't sound well, son. Are you okay?"

Denver took a pencil to one eyebrow. "I'm fine, Mom, and I do need to, Mom. If not me, where is the money coming from?" He said, moving the pencil to the other eyebrow.

"By the way, your grandpa says hi," Mom mentioned while Denver began applying some liquid eyeliner to his left eye. "What? Okay, I'll ask... Your grandpa wants to know if you'll be back for Christmas."

Denver looked around for the right eyeshadow. "Tell him I don't think so," he said, applying it.

"Denver doesn't think so," Mom relayed away from the phone.

"Don't they celebrate Christmas where you are? Is that it?" Mom asked.

Denver tilted his head to do the other eye. "They do, but I can't get away. If I work during that time, I get overtime. So I can get everything done faster."

"This call must be costing you a huge amount. Where are you? " Mom inquired.

"Um, Italy. I can't say much more; they are very private," Denver replied.

Mom sounded impressed. "Italy, wow, that sounds glamorous."

"Yeah," Denver said, applying lipstick and searching for the right fake eyelashes and mascara.

"I guess this call is expensive," Mom noted. "Are you sure you can afford to do this too?"

Denver got up and flicked through the wardrobe, searching for the right dress the way he used to browse the used games section. He then held the dress against his chest to check it in the mirror.

"Of course, I can. They have the internet in Italy too. It's a shame I'm not allowed to Zoom you."

Mom's voice changed, "I'm getting tired. I don't want you to lie to me. I was stopped by that friend of yours at school, the one who hangs out in the hallway. He said you had been picked up by a limo used by a drug dealer. He said they always need people to back them up. They go to places like Colombia. He said they pay well. Just tell me you'll be safe."

"I'm going to be fine, Mom. I'll be coming through the front door soon," Denver said. "Look, I've got to go."

"Okay, see you soon. Call when you can," Mom said.

"Will do. Bye!" Denver said.

Denver in one practiced move bundled his shrivelled parts up and tucked them away under the gaff. Rachel put some more body tape on. Perhaps Mimi and the other trans girls were right. Getting a piercing on Denvers head with a chain to a ring on her rear pussy would be far more convenient and clean. Rachel slipped some panties on, and put her fingers into her fine Saint Laurent Swarovski tights and pulled them over her curvaceous legs.

Standing up Rachel pulled the dress on and cleared her throat. It felt sore speaking so low these days and was becoming a strain. She looked at herself as she tightened up her corset dress. It was very sexy and a favorite among Douglas, Peter, and her Instagram followers. It was the type of tight dress meant for him, the kind that filled the front window of an expensive boutique but no one dared to wear. Normally, it was there to shock passersby, enticing them to explore the more conventional clothes inside. This was the kind of stuff she was famous for. Italian fashions where generally too much for Americans but nothing was too chic or shocking for Rachel.

Rachel began brushing and styling her hair. She felt like talking to Charlie. She needed to discuss renegotiating with Levant. Usually, she wouldn't take an action like this without discussing it with Charlie first. However, considering what Lucy had told her, Charlie might not be the best person to confide in. Charlie depended on Rachel's presence, so she couldn't trust her. She needed a few more months; so far being the attentive girlfriend had only made Levant desire her more. On the other hand he was more busy so it might be working. This time she would agree to more things he wanted and not be so remote. That was her last mistake she wouldn't make it again. In the mean while she had to go all out begin more intimate with Levant. After all doctor Cooper's tests proved it, perhaps if she explored her feminine side more thoroughly she might figure out why she still thought about going back.

"Okay," Rachel said to the mirror as she brushed her hair, "Douglas, I think I have some good news... Hi, Douglas. Look, I've been thinking about things. Douglas, I was wondering how you felt about handjobs... Hi, Douglas, I suppose you know why I'm here."

*****************

The morning after the dinner with Peyton, Elijah, and Brooke, Rachel entered Levant's luxurious Venetian bed room carrying a large breakfast tray in her hands. The room was adorned with elegant furnishings and a sense of grandeur. She placed the tray on Levant's lap as he struggled to sit up in the four-poster bed, surrounded by plush pillows and sumptuous bedding.

"Oh, breakfast in bed," Levant said sitting up, his voice filled with surprise. "Why did I deserve this?"

"Nothing," Rachel replied, gracefully removing her dressing gown and slipping into the other side of the warm bed. "Just being with you," she said, pulling the soft sheet over herself. "Putting up with Peyton, Elijah, and Brooke. I know they are my friends more than yours, so for them and the a trickle of people who have been swinging by it was to show my flag of appreciation. Any way I figured you might have a headache after last night's celebrations," Rachel added, her eyes scanning the opulent surroundings of the room.

"It's fine. Cinnamon, you look fabulous," Levant said, his gaze fixed on Rachel. "You always do. I can't believe I get to see you every morning and every night. Every day with you feels brand new. It's hard to describe. With you, it feels fresh, full of excitement, and the possibilities feel unlimited, but only with you." While he spoke he picked up the wild flower in the vase on the tray and ran it over her breast.

"Thanks," Rachel said, her appreciation evident. "I'm pretty lucky to be with you too. Do you have any plans for the next day or two?" She glanced down at the exquisite espresso before her, served in the smallest and most delicately designed cup, it fitted perfectly within the luxurious ambiance of the Venetian hotel room.

She was accustomed to Levant's flexible schedule. It was her role as his "pop-up" girlfriend. Perhaps that's why he liked her--she could be picked up or dropped at a moment's notice. She didn't fuss or frown when he wasn't around. Today if he was unavailable, she might fuck with Peter again. He had promised to take her on a night tour of the local bordellos. He planned to check into a hotel that charged by the hour and provided a bowl of condoms in each room. But that was for later. Right now, she needed an extension to the contract term.

"I don't have any meetings this morning," Levant said. "We could do something fun today."

"It's been more enjoyable being with you than I anticipated," Rachel said. She reached under the sheets and placed her hand on his stomach. Levant's eyes slightly widened at the touch. Charlie had done the same thing with Rachel whenever she wanted to explore something particularly kinky.

"Italy has been a blast," Rachel continued, running her hands over his firm six-pack stomach. "Remember when we spontaneously flew to Rome for the evening? That was very romantic," Rachel said, her hand gently stroking Levant's hard abs. "Oh and that trip to Ibiza that was amazing. I've never danced so much. This country has been a constant delight. My head has been spinning the entire time my dear little monster."

It was true; her notebook, filled with ideas for poetry, overflowed with effervescent words and annotated napkins from various expensive restaurants.

"Oh, I so feel the same way, Cinnamon " Levant said, smiling.

Rachel rolled over, intentionally revealing more of her breasts through the negligee. Her hand wandered over Levant's body beneath the sheets.

"Let's be honest. You know I still don't believe I'm the right long-term girl for you. You take so many risks for me, which I appreciate, but it's not fair on you in the long run. Let's face it, you deserve a woman who can fulfil all your needs and desires," Rachel confessed. Her dark eye shadow looked pensively down.

"But," Levant interrupted, "there's always a 'but' here."

"But... she's not here," Rachel said, smiling mischievously, moving her face closer to his, "and I am."

As she spoke, she reached down and began to caress Levant's arousal. He took a sudden, sharp intake of breath. She kissed him them pulled away far to early and smiled coquettishly to him.

"I'm not a good girl," Rachel said with a seductive smirk "I know I can be quite capricious. To be fair, it's my only vanity." Her eyes looked at him with seduction and a hint of mischief, daring him to explore the depths of his desire. She reached under the sheets and thought of hospital bills.

Rachel held Levant's cock for the first time and wrapped her fingers around it. It bristled to her touch.

She replayed in her mind what Charlie had done to Denver. She knew she had to do something to make Levant feel that extending the contract would carry a huge pay off. This payoff had to be big enough to outweigh any barbed words Lucy might have been dripping in his ears.

"I've learned a lot during the time I've spent with you." Rachel continued as she began massaging his dick.

Levant reached for his crotch.

"A a a." Rachel corrected. He stopped.

"You enjoy your breakfast. Let me drive," Rachel said softly continuing.

Levant smiled and leaned back into the soft pillows.

Rachel carried on moving her thumb and fore finger up and down Levant's rapidly firming cock.

"I've learned lots of new things in my time with you," Rachel said softly.

Levant leaned back to enjoy Rachel touching his manhood for the first time. Rachel could feel Levant's firm dick in her hands, which wasn't much different from Denver's, or at least how Denver's had been. She gently stroked his balls. As she did so, the image of the Italian journalist popped into her head. He was suave and good-looking. Rachel would have enjoyed rejecting him.

Levant reclined with serene ease, his body sinking into the soft embrace of pillows and blankets. A mischievous curve played upon his lips, revealing an enigmatic smile that stretched across his face, as if harboring secrets and radiating pure joy.

"Nice," he said, relaxing, then refocusing. "Are you okay with doing this?"

"You know," Rachel said, shifting slightly to give him a better view of her ass, "I actually am. With you, I've grown and evolved. I still have my limits, but... I can see where the boundaries truly need to be, and that means the fun doesn't have to stop, you know? Not exactly where it used to. Isn't this nice?"

12