Red Swallow Ch. 03

Story Info
Desiree prepares for and entertains her first patron.
7.6k words
4.77
9.6k
15

Part 3 of the 9 part series

Updated 06/09/2023
Created 03/18/2020
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

After completing "The Diary of Jewel Delacroix" I was approached via E-mail by Rachael Ricci Swede and asked if I would consider writing a story idea she had. After a few emails I was intrigued by her idea and agreed to write it.

This is an original story by Barbara Jean Goodhead.

Written in collaboration with Ideas and Plot Points by Rachael Ricci Swede.

All characters are fictitious and bear no resemblance to any person living, or dead, fictional or non-fictional, in this or in any other universe. All are over the age of 18 unless specifically stated otherwise.

The following story contains themes of cross-dressing, feminization, forced feminization, reluctance, non-consent, and many other adult topics.

Here are the usual disclaimers:

This is porn; you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is.

You're an adult, life is short, find porn you like and read that instead. But if this is a style you enjoy, then feel free to comment and provide constructive criticism and feedback. I need to grow as an author and honest constructive criticism is always welcome.

******

Red Swallow Chapter 3

The swallow bird is usually associated with love, loyalty and peace. Swallows as bird spirit animals are considered joyful, decisive and full of hope.

**

At first, Dustin was appalled. Then merely astonished, and then just uncomfortable.

Every evening Dustin would arrive at club COBALT and transform into Desiree and waitress for the club. As he waited tables he watched as the Diva's and Hostesses would work each table and attend to the customers. At first he found he couldn't really watch when the hostess would lead a customer away, taking him (or her, depending on the case) upstairs for private entertainment.

Dustin was wearing his waitressing uniform. It varied quite a bit from day to day what the uniform would be but today was a replica of the iconic playboy bunny uniforms from the last century.

Dustin...Desiree when he was working and in character, delivered the tray of drinks to the table and was rewarded as a fat customer with greasy hands shoved his tip into the hem of her thigh high fishnet stockings.

"Thanks love. Are you on the menu today?" The fat man asked as he copped a feel of Desiree's ass.

"I'm sorry, not today." Desiree answered sweetly with a smile.

The fat man spanked her ass and his companions at the table all laughed as she let out an involuntary yelp of surprise.

"Maybe next time then, 'eh love." The fat man leered at her as she made her escape to wait on her remaining tables.

Desiree checked on each table before retreating back to the bar where other waitresses had gathered until they were needed. She pulled out the money from her fishnet stocking and was disappointed to see a one dollar bill.

Fucking cheapskates!

At this rate, with her minimum wage salary she was not going to make enough to pay for her rent this month.

"How is it going?" Trixie asked, as she sauntered past. She had just returned from upstairs and obviously showered and changed as she was wearing a different dress than the one she wore earlier.

"Bad. Tips are lousy today." They were lousy everyday really. Waitressing was a tough way to make a living. Desiree really needed this job. She had sent out her resume to all the financial institutions she could think of but not a single one had called back. No interviews, no communications, nothing. Desiree wondered if she had been black listed.

"How is it that you are always doing so well?" Desiree asked Trixie as she watched her tables.

"I provide extra services" Trixie answered with a wink.

"Anastasya mentioned something like that to me. What services?" Desiree asked innocently.

"Look, Dez, You've been here three weeks now. I'm sure you've figured it out." Trixie watched Desiree as she blushed furiously.

"I'm just not sure that I can do that."

"It's just like any other role, right? You're an actor...it's all about getting into the right frame of mind."

Desiree found herself nodding along in understanding.

"This," Trixie indicated herself and the dress she was wearing "Is just a role. You're an actor, play your part, don't act the whore, be the whore."

Desiree blushed more deeply than before. Anastasya was keeping Desiree as a waitress and not a hostess because she was not "on the menu" and the customers couldn't choose her for "private entertainment."

"Or starve; your choice."

Trixie walked away to attend to another table, She was one of the most popular hostesses here.

**

"Do I really have to buy all these clothes?" Desiree whined. Costumes for an acting part were supposed to be provided by the production company.

"Yes you do!" Anastasya said forcefully. "Each outfit is yours and yours alone; measured to fit you perfectly."

Desiree stood on a platform in just her bra and panties. Anastasya had the shop assistant pad Desiree's ass and thighs and also place larger C cup breast forms inside her new larger bra cups. Every outfit would be tailored to fit Desiree's new curvaceous form.

"But I can't afford all this." Desiree whined again.

"I am loaning you the money. You will pay me back each week with a percentage of your earnings." Anastasya said in a tone that would brook no discussion.

Anastasya also allowed herself a small smile of victory. Paying back the money for the clothes would take a long time, keeping Desiree in her debt and working for her for quite awhile.

The shop assistant finally spoke up.

"Ok. I have all her measurements, you just need to select the outfits and we can tailor them all to fit."

Desiree put her dress back on. Anastasya had insisted that she accompany her to the store while dressed in feminine clothing. For practice she said. Actors need to rehearse after all, don't they?

"Firstly, we will need school girl uniforms, they are one of the most popular fetishes there are." Anastasya selected the items from the display without consulting Desiree.

"We need these three French maid's uniforms, a cat suit, a leather dress, these leather skirts, tops..." Anastasya's fingers seemed to blur as she worked the keyboard and touch screen for the on-line catalog.

"Shoes...stockings...garters...garter belts...bras...panties...corsets..." Item after item flew by in a blur too fast for Desiree to follow.

After about 15 minutes of typing Anastasya had a look of satisfaction as she finished with her selections.

"How much?" Desiree worriedly asked.

Anastasya just pointed to the bottom of the screen where the total was displayed.

Desiree nearly felt faint...the bill was over $4000 dollars.

"Do I really need this much?" She asked. Mentally calculating her expected income she realized that it would likely take her at least a year to pay off this much money.

"Yes!" Anastasya answered. "And we haven't even started on Jewelry. We can come back for the rest after you've started working."

The Rest? There's more? Desiree was suddenly worried. What the hell had she managed to get herself into?

Anastasya led Desiree from the store after she paid the bill. Anastasya and Desiree had walked from COBALT to the store, a distance of several city blocks. Anastasya said she wanted Desiree to be more comfortable when dressed in women's clothing and more practiced when walking in heels.

Desiree was wearing a light summer sun dress, in a pale yellow with a floral print around the bust, matching pale yellow 4 inch heels and a similar handbag to carry her accessories.

Desiree didn't have any trouble with heels anymore. Spending the nights working at COBALT on her feet wearing high heels had been enough of practice to make her proficient.

And walking around New York City during the day dressed en femme wasn't as serious a challenge as Dustin had thought it would be...He just stayed in character as Desiree and found that he had no problems at all. She even found the cat calls and whistles from strangers were unexpectedly flattering to her.

Despite now owing even more money to Anastasya and COBALT, Desiree was having a really good day.

**

"Ok, so how do you do this anyway?"

Desiree sat next to Trixie and Anastasya placing the dildo at the edge of the coffee table before her, the suction cup base holding it securely in place. Part of her recoiled at the thoughts she was having while another part could only think of the late notice she had received from her landlord. Past due rent was nothing to laugh at.

"Just hold onto the base near the balls." Trixie instructed.

"Start with a kiss on the head, and maybe stroke the shaft with your other hand."

"Good" Anastasya praised as Desiree followed the instructions. "Also you may want to tenderly fondle the balls with your fingers, most men like that."

Desiree was kneeling at the end of the coffee table while she fondled the dildo's silicon balls that dangled over the edge of the table and as she kissed the tip and head and stroked the shaft.

"Good girl, now slowly open your mouth and let your lips encompass the head of the cock." Trixie continued.

Desiree closed her eyes as she made an O with her mouth and began to fellate the head of the dildo.

"Don't always close your eyes at first" Anastasya commanded. "Focus is important yet most men also like eye contact. They like to see you are enjoying serving them."

Desiree opened her eyes and made eye contact with Anastasya, as she bobbed lightly on the head of the cock.

"That's good Dez," Trixie observed "Head bob up and down, but each time you go down, go down a little bit more."

"Good girl," Anastasya praised again, "Now when you get this far down you are about to hit your gag reflex. Some girls just relax their throat and let it slide back down. Others find that swallowing it will let it slip past the back of the throat easily. You will have to try and see what works best for you."

Desiree tried swallowing as the cock head hit the back of her throat and was overcome with the urge to throw up. She spit out the offending member from her mouth with an unpleasant "Aawwpp" sound and sat back to catch her breath.

Desiree massaged her throat as her mouth and throat recovered from the unfamiliar sensation of fullness and being stretched.

"That wasn't bad for your first time." Trixie encouraged.

"But you will have to do better." Anastasya ordered, her Russian accent giving her a commanding and imperious tone.

"You can close your eyes to focus when you reach that point. A lot of men like it when it looks like you have to concentrate hard to swallow their dicks. It makes them feel larger than they really are."

Anastasya waited until Desiree caught her breath.

"Good. Now begin again."

Desiree started to practice sucking on the dildo once more. I can do this, she thought determinedly.

**

Desiree was waiting tables again when Trixie approached her.

"Have you been practicing with your dildo?" She asked rather loudly.

The men who were sitting at the table she was waiting perked up at the announcement and all smiled at her lasciviously. The one woman in their group looked embarrassed but also curious.

"Not so loud...please..." Desiree took Trixie by the elbow and led her away.

Back near the bar she let go, and turned to face her and saw that Trixie was smiling at her, still waiting for the answer to her question.

"Yes...damn you."

Desiree was irritated by the question. She still felt uncomfortable with her 'homework' as Trixie and Anastasya called it.

Desiree's waitressing uniform today was modeled after a maids' uniform. COBALT was delivering a Japanese Maid Café style presentation this night and all the waitresses were dressed up with cute white maid's uniforms with pale pink collars, cuffs, gloves, and aprons.

Desiree's high heel stiletto shoes were also the same shade of pale pink to match the uniform. Her hair was in loose pintails that had extensions woven into them to make them longer than normal. Pink bows detailed each pintail at the top of her head. The icing on the cake was the cute little cat's ears she wore on top of her head.

The uniforms had black ribbons as an accent color for each item of clothing. Pink ruffled panties, white petticoats, and pink and white striped thigh high stockings completed the outfit. The hem of the skirt fell to just above mid thigh and the tops of her stockings and her garter belt straps were showing.

Needless to say, the costumes were very popular with the clientele.

"And how was it?" Trixie asked? "Did you practice the way I told you?"

Desiree's homework had been to take home the dildo, buy some lube and an enema kit, and after cleaning herself out, practice anal sex with the dildo.

"It hurt! And yes, I practiced just the way you said." Desiree answered, face flushing with embarrassment. She had followed Trixie's instructions and placed the suction cup dildo in her shower so as to be able to push back onto the dildo using her hand on the opposite wall.

"Did you get it all the way in?" Trixie found she had to exercise a lot of self control to keep from laughing at Desiree's embarrassment.

"Yes." Just when she thought she couldn't blush any deeper...

"For how long?" Trixie just couldn't let it go now, she had to know.

"30 minutes, just like you and Anastasya said." Desiree wanted to crawl away and hide now.

"Good girl." Trixie praised. She was mildly surprised to see Desiree relax a bit at her praise.

"So...do you have it?" Trixie asked her final question?

Desiree just nodded as her blush returned full force. Trixie patted Desiree's bottom through the petticoat and the ruffle panties and felt the hard end of the butt plug that was firmly inserted inside Desiree's ass.

Trixie smiled; she knew she had seen the extra bit of sway in Desiree's hips and bottom that plug inside her would induce!

"How long do I keep it in?" Desiree asked.

"All shift. Take it out after you go home." Trixie answered.

"I have to go home with this?" Desiree asked, shocked.

"Of course; you also have to go home dressed in this as well. The walk will do you good and the extra practice will as well."

"Trixie, Table 10 requested you." Anastasya had been listening in on their conversation and only interrupted since Trixie was needed now.

"Keep up the good work Dez." Trixie said as she smiled and walked away to her next hostessing session.

"Yes ma'am." Desiree responded politely.

"You looked thirsty. Have you been drinking water?" Anastasya asked.

'Yes Ma'am." Desiree answered. She indicated a bottle of water she was keeping out of the way at the waitressing station, one among the many bottles each of the girls kept when on duty.

"Good girl" Anastasya praised. "It's important to stay hydrated."

Desiree nodded her head in agreement before noticing she was needed at one of her tables that didn't have a hostess in attendance.

Anastasya watch as Desiree walked away. She noticed that Desiree's skin had become healthier and clearer, and that Desiree's curves have been becoming more pronounced. Her facial features were also smoother, more feminine. Anastasya smiled at the effects that the cocktail of hormones that were in the water were having on Desiree.

Eventually Anastasya planned to have Desiree receive breast, thigh, and butt implants, at her own expense, of course. Keeping the girls in debt to her helped keep them in line and working after all, contractual obligations being what they are.

She was pretty before in an androgynous way, but she was becoming quite beautiful now. Anastasya was pleased with the improvements. Soon Desiree would be ready to go back onstage and start hostessing instead of merely waitressing.

**

By the time the club closed and Desiree had cleared her receipts, and helped with a few final clean-up assignments it was early morning when she walked home to her apartment.

Desiree enjoyed her walk. The neighborhood was a safe one and it was early enough that she didn't see too many people coming or going. She walked up the stairs at her apartment building and as she made her way down the hallway on her floor to her door the door to the apartment across from hers opened.

Taya hated early start days at work. Her admin job paid well but arranging time for her daughter to have a babysitter prior to day care offset the income she made from the extra hours. As she bundled her daughter out of the apartment she turned to see...was that her neighbor?

"Good Morning Taya." Desiree smiled as she spoke, retrieving her door key from her purse.

"Uh...good morning...Dustin, right?" Taya stifled a giggle as she noticed the over the top Maid's uniform he was wearing. Were those cat's ears in his hair? Still, if she hadn't known he was a guy she would have never known.

"Um...Yep...That's me. Are you heading to work?"

"Yes, early start today."

"Yeah, late night for me though; just getting home now." Desiree smiled back.

"Well, have a good day."

"You have a good one as well." Taya turned to leave. As funny as she thought the situation was she also thought that her neighbor made a really attractive woman.

**

Desiree smiled as she finished her song. She was finally being allowed back on stage and was the opening act tonight and the song she had chosen was picked specifically to warm up and excite the crowd. She smiled as their reaction was exactly what she had hoped for.

"I've been trying to do it right, (hey) I've been living a lonely life"

Desiree was glad that the backing track provided the "Hey/Ho" to the song.

"I belong with you, you belong with me, you're my sweetheart."

People were laughing, cheering, smiling, the mood in the house was good, and the atmosphere was amazing. When Desiree finished the song the applause was amazing as well. She was becoming known for her singing and her oldies song performances.

Desiree exited the stage and went to see Anastasya. She had finally placed Desiree 'On the Menu' and Desiree was nervous and excited. Because she was "new" to the menu she would also fetch a premium price. Desiree had marveled at the sum and what her share was to be. If everything went well she would actually be able to catch up on her rent.

Pushing down her nervous excitement Desiree received her table assignment and went to attend her guests. It's just a role, she silently chanted. Be the whore...

She was quite disappointed to see who was sitting at her table.

**

Carl Marks was sitting alone at club COBALT. He watched entranced as Desiree finished her song and left the stage. She looked amazing and her performance was flawless in his eyes.

Carl was initially confused when he first saw Dustin dressed up as Desiree. He looked so pretty all made up like that. He was prettier than Carl's wife. Carl had slowly begun to find that he was fantasizing about Desiree at the most inopportune moments. Even when he made love to his wife he found he could no longer get off unless he fantasized about Desiree.

His wife was so unenthusiastic when it came to sex. She just laid there as Carl would rut against her, trying to satisfy his urges. Carl's wife thought sex was dirty and only for procreation. That they had no children was a testament to how often they bothered to have sex anymore.

Carl blamed David as well. It was his idea to come to COBALT in the first place and it was his talk that gave Carl his fantasies. And now Carl was obsessed with having Desiree fulfill those fantasies.

"Why do you like Tranny's so much?" Carl had asked, feigning innocence during a coffee break at work one day. "Why not a real woman?"

"Man; Trannies, T-Gurls, She-males...they all want one thing." David stated.