The Angelica Lu Sissy Diaries Ch. 05

Dear Reader,

We've firmly entered into fantasy territory, so expect the next few stories to be a bit more imaginative. To recap:

Chapter 1 - Angelica Lu takes her first step in becoming a sissy prostitute.

Chapter 2 - Angelica Lu sucks her first cock.

Chapter 3 - Angelica Lu has doubts but doubles down.

Chapter 4 - Angelica Lu loses her anal virginity.

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I've accepted that I'm Angelica Lu, but I still don't accept that Angelica and I are the same person. We're two entities trapped in the same body and she comes out when I get dressed. As long as I'm not dressed, I'm not her right? I don't desire men and I don't care for what she does. It's only when I put on the makeup, the outfits and the wigs that I'm her. As long as I don't dress up... as long as I don't dress up...

Over the next couple of months, Angelica Lu became more popular. Mrs. Dev's clients began spreading stories about Angelica through word of mouth and also through anonymous online forums where they discuss sex workers. Soon, the Asian sissy slut began coming up in more and more discussions. At first, Angelica was booked maybe once a month. Then, it became once every two weeks. After a certain point Angelica was seeing multiple customers on Fridays and the weekends where she had more time off. The vast majority of customers were only paying for oral, and Angelica was more than happy with that.

"Gulp! Slurp Slup... ughhh."

Angelica deep throats daddy's cock, bobbing her head up and down while maintaining her gaze with her client's eyes. He closes his eyes and begins to moan. Angelica feels the cum move up daddy's cock and when he explodes in her mouth, Angelica takes it all. She opens her mouth to show daddy the cum all over her tongue and inside her mouth. She closes her mouth and swallows and then opens her mouth again, showing the customer she drank every drop.

After the client leaves, Angelica cleans up and Mrs. Dev helps reapply some of the lipstick which had smeared off. Angelica was going to see another customer in thirty minutes. Angelica was now making about two thousand dollars a week at this point just from being a prostitute. Combined with her pay from her job, Angelica was finally able to save up money for things that she had always wanted. A new car, a better neighborhood to live in, and even some guilty pleasures like new clothes and other, more sensual items like butt plugs and dildos for her to practice on. Angelica was embracing her new lifestyle and began to live a bit more lavishly.

One day, Mrs. Dev called me out of the blue. As she normally doesn't call, I ask her what's up.

"I have...I have someone who's very special that I'd like you to meet. He's umm...let's just say if you can meet his expectations, you can make a pretty penny."

"I'm interested, go on."

"I'm just warning you though, he's a bit eccentric, okay?"

I was told that the client was very wealthy and was interested in booking me for a whole day. I had to find a good time, and it looked like it was going to be Friday again. He had booked Friday from 12:00 PM to 12:00 AM, which needless to say made me question things. The longest session I ever had was my first anal session, which had lasted over two hours. I wasn't even sure what we would even possibly do for twelve hours, but the client was paying an amount of money that I've never received before. On top of it all, Mrs. Dev told me she would be giving me a bigger cut ahead of time, because this client might be...difficult. I was extremely nervous, but at the same time extremely tempted and excited.

I arrive at 11:00 AM on Friday to prepare for this client. I was given the usual enema and douche to clean out my anus, which I figured this client would be interested in if he was spending that much time with me. Mrs. Dev begins to apply makeup as usual, but this time applies a darker eye shadow and darker lipstick. Mrs. Dev is putting more work into the makeup than usual and when Angelica looked in the mirror, she was shocked. Angelica can often pass for a woman if she really tried, but today she looked like she was passing with flying colors. She brought out the ponytail wig along with the wig cap and wig bands to secure the wig. Angelica knew what that meant. Mrs. Dev then brought out an outfit for Angelica Lu. Angelica was dressed in an extremely short white skirt that revealed the bottom of her butt cheeks and a small string top that left a lot of skin exposed.

The client arrives on time. He's an older man with a bit of a belly, but otherwise a pretty handsome man. He showers, changes into a bathrobe and approaches Angelica, who stands up to greet him.

"Hey Angelica Lu, I've heard a lot about you, it's nice to finally meet!"

The client extends his hand for a handshake. Angelica is completely surprised. It was like the client was there to take Angelica out on a date, not fuck her brains out. Angelica sheepishly extends her hand for a handshake. The client then puts his arms around Angelica's waist and moves in for a hug. He sniffs Angelica's neck and gives her a a kiss on the lips. Angelica is taken aback. Clients have fucked her tight boipussy, they had licked Angelica's clitty, but no one had kissed her on the lips.

"Are you ready?"

"Huh?"

Daddy took Angelica's hand and led her outside. He clicked his keys and opened the door on his Range Rover to let Angelica in. They drove to a nice steakhouse where daddy ordered Angelica some food. Angelica was extremely uncomfortable wearing her short skirt and revealing top outside to such a nice restaurant. Angelica ordered a steak salad as she didn't want to stuff herself while daddy bought a steak and potato meal. He cut the steak deliberately into even chunks and ate with the most proper manners Angelica had ever seen anyone eat. Before he ate the last piece of steak, he stabbed into it with his fork and told Angelica to open wide and fed it into her mouth. The piece was a bit bigger than she thought and when she bit into it the juices came out of the side of her mouth. Daddy took his napkin and wiped Angelica's mouth. At this point Angelica was lost on what was happening. This was her first time outside as a sissy and she could feel some people looking at her, questioning if she was a man. She began acting extra demure by looking down at the table and sulking her shoulders together to appear more feminine, especially when the waiter arrived.

After lunch, daddy went to go get his car but instructed Angelica Lu to stand in front of the restaurant to wait for him. The restaurant was located at a busy intersection where lots of people were walking by and they all seemed to be staring at Angelica. A man who looked to be a day laborer approached Angelica and grabbed her clitty before walking past her. Another woman looked and her and muttered 'whore' before walking by. Angelica was scared and tired of waiting, but at the same time she was also getting turned on by the attention she was getting. Finally, after what felt like an hour, daddy pulled up and told her to get in.

"Oh my god daddy where were you? I was standing there for such a long time and..."

"Shhh baby. Shhh."

On the drive back to Mrs. Dev's place, daddy began to touch Angelica's little sissy clitty. He began to fondle her while still maintaining his eyes on the road. They pulled up next to another car and daddy suddenly gripped Angelica's balls hard. Angelica let out a slight scream causing the drivers in the other car to look at her. As soon as they looked, daddy began to rub Angelica's clitty hard and she began to moan. The light turned green and daddy drove off. They arrive closer to Mrs. Dev's place but instead drive past it. Angelica became worried; she had no idea where daddy was taking her.

"Umm where are we going?"

"Shh."

Daddy kept driving until he reached the outskirts of town. He pulled into a gas station and told Angelica to get out. Then all of a sudden, he pulled down his pants and instructed Angelica to get to work. Angelica was dumbfounded. She couldn't do that there! Daddy gave her one look and she realized she had no choice in the matter. She got down on her knees on the gas station floor and began to suck on daddy's balls. She started licking his shaft and put his head into her mouth, licking it like a lollipop. People are walking by observing the scene, but they said nothing and walked past.

"That's enough baby, let's go."

"Y-yes daddy."

Daddy drove them back to Mrs. Dev's place while continuing to fondle Angelica's tiny sissy clitty until they arrived. Angelica was so uncomfortable with everything that had happened yet she was also so turned on. By the time she got out of daddy's Range Rover, her little clitty was hard and dripping with pre-cum.

They go into Mrs. Dev's place, who opens the door to let them in. She gives Angelica Lu a wink and leads them to the bedroom where she promptly closes the door behind her as she walks out. Daddy instructs Angelica Lu to get on the bed. He takes off his clothes and snuggles next to Angelica's warm sun kissed body and begins kissing her. He kisses her shoulders, her neck, her ears and pulls down her shirt and starts kissing her nipples. He then holds Angelica Lu's chin in his hands and moves her face towards his, where he begins kissing her lips. He then pulls her chin down and opens Angelica's mouth and begins deep French kissing her. Daddy's tongue is molesting Angelica's mouth and he begins to lick her tongue and lips. Angelica's little sissy clitty begins getting harder and harder.

"Mmm who's a good girl."

"I'm a good girl daddy! I'm YOUR good girl. Ughhhhh!"

Daddy continues using his hands and lips all over Angelica's body. He begins to massage her breasts, pull her foreskin back and suck on her clitty. At this point, Angelica Lu's body is in so much pleasure she couldn't help but start drooling out of her mouth.

"Say you love me, Angelica Lu. Say you love your daddy."

"I-I-I love you daddy!"

Daddy pulls off Angelica Lu's short skirt and panties and turns her over. He takes some oil left on the bed by Mrs. Dev and pours it into Angelica Lu's boipussy. He begins to massage it slowly and sensually causing Angelica to moan harder and harder. Once he could sense Angelica loosening up, he begins sticking his fingers in one by one. He expertly massages Angelica's boipussy until it's gaping, letting daddy know it was ready for penetration. Daddy slowly put his penis into Angelica's boipussy and carefully puts some oil onto his cock as well. Then he starts fucking Angelica super slowly and sensually. Unlike her last anal experience, this time it felt so much different. There was no pain, only pleasure. As daddy kept sensually penetrating Angelica Lu, he slowly shifted himself onto his back and placed Angelica on top. Daddy was surprisingly strong and began to lift Angelica Lu up and down on his cock. Angelica was riding daddy with her face towards the ceiling and she began to feel something she had never experienced before. Her body began feeling tight and pressure began building near her boipussy. Before she knew it, she was convulsing involuntarily and cum began shooting out of her tiny sissy clitty. She had came many times before, but never like this. Her eyes rolled to the back of her head, drool came down her chin, and her clitty went from hard to limp and began to spin up, down and around, spitting cum all over daddy.

Daddy had not cum yet, so he continued to lift Angelica Lu's limp body up and down. Angelica's mind at this point was completely gone. She had just sissygasmed and her mouth just kept letting out a deep, continuous moan. Daddy, however, just kept fucking Angelica Lu's boipussy. The sun had gone down already and it was dark, so he must have just fucked Angelica for hours. Then, all of a sudden, Angelica had another sissygasm! She was convulsing and quivering so much that her body looked like a puppet pulled by daddy's strings in all directions. Finally, daddy came. He came so hard and so violent that Angelica flew off his penis and her limp body fell on top of his. Angelica's boipussy began forcing the cum out and it spilled like a stream out of it.

At this point, Angelica did not know who she was. She had been mind fucked and physically fucked so thoroughly that she wasn't sure what was happening anymore. Daddy laid beside Angelica and began whispering into her ear.

"I love you Angelica Lu. You're my woman, my possession. Repeat that back to me."

"I love you daddy. I'm your woman, you own me daddy."

Angelica felt like she would do anything for daddy. If daddy needed her to please him, she would do it without hesitation. Whatever daddy wanted, she would do. Angelica was completely broken and was now daddy's sissy slave.

Angelica fell asleep in daddy's arms and when she woke up, it was already the next morning and daddy was gone. Mrs. Dev came in and brought Angelica some orange juice and water.

"W-what happened to me?" Angelica asked.

"You earned me a lot of money, that's what happened!"

Angelica was thankful for daddy's money, but the experience brought her something she never thought possible. Even after the whole thing, she kept thinking about daddy. She never really gave a fuck about her previous clients even though they made her cum, but this time it was different. She continued to service clients in the next few weeks, but she could not stop thinking about daddy.

The whole experience left me deeply confused. Every few hours, I would check my texts to see if Mrs. Dev would text me about daddy visiting me again, but the text never arrived. My obsessive behavior continued for weeks. I would jump to my phone at the sound of a text, being trained to respond like Pavlov's dog.

One day the text arrived. Daddy wanted to see me again! I was so excited that I began to drip pre-cum out of instinct. Mrs. Dev however, gave me a very harsh warning this time. This session would not be like the last one, she said. The text read:

"For this session, if you accept this, will require you to sign some legal documents indicating that [ REDACTED ] is not responsible for any serious bodily injury or harm, including death."

Mrs. Dev told me that this session would pay double what the last one paid, but personally asked that I not take it.

Against her wishes, I accepted. The money was nice, but my mind had been taken over by daddy and at this point, I would die for him.