Nikki Meets Macy And Gavin

Nikki Meets Macy and Gavin -- New Side Gig Clients

This story has been posted to Literotica.com with the full knowledge of the original author under my pen name, NikkijMaadison. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author. I edited this story using Microsoft for spellchecking, flagging punctuation, grammar review, and as a dictionary. I use any other suggestions only as a guide. You may discover mistakes. That will happen.

© Copyright NikkijMaadison - All rights reserved.

This story contains sexual activities and situations between consenting adults. All characters are above the age of eighteen. Any similarity to any individual, living or deceased, or location is coincidental and unintended. The story will be told in the first person.

This story was intended to be submitted to the "On the Job 2025" challenge. Unfortunately, it was not finished by the deadline.

Prelude

I'm a bartender at '

Prepare to Be Amazed'

, a trendy LGBTQ bar in Rehoboth Beach, Delaware. Rehoboth Beach is an openly gay community that caters to the gay lifestyle. Beachgoers who reside in the major cities on the East Coast flock to the beach year-round, not just in the summer months.

My name is Jennifer Nicole Madison. I'm called Nikki. I'm a full-time non-op, functional trans woman. If I must say so myself, I am a stunning woman, very athletic, with great legs and a round, perky booty that has always been one of my greatest assets. And yes, I've been under the cosmetic knife, adding 370 cc breast implants, hairline and eyebrow lifts, a reshaped chin, and a tracheal shave.

After transitioning, I moved to the beach. I am kinky and naughty with a wild side. I'm epitomized as a slut that is a woman with the morals of a man, but that's not much of a stretch for a chick with a dick.

I live and work with the

'Amazed'

co-owners Tommy and Ralph, who also co-own several other restaurants in the beach towns on the Delmarva peninsula. I give pleasure to the guys I live with. I am perfectly fine being their sex toy. Besides bartending, I do event planning and fill-in Hostess at their restaurants. I also escort on behalf of the guys. Yes, they pimp me. I am a whore, and I love it. I look forward to my side gigs.

Tuesday at the Restaurant

I don't usually work on Tuesdays, but Tommy asked me to help with the bar's lunch crowd. He also had a few dates set up for me this afternoon.

'Amazed'

has a private playroom to entertain special customers. He also wanted me to meet a new client. Her name is Macy.

Today I wore a short, pleated white skirt, low cut top that showcased my boobies. Underneath, I wore a pink silicone chastity and pink lace panties.

Even in late September, our lunch business is brisk. At two o'clock, Aaron, a fellow bartender, took over my bar duties so I could entertain my two regulars, Cole and Carson. From time to time, Aaron and I are also bump buddies.

Cole is a handsome black man with a chiseled physique and no body fat. His cock is sizable, not the largest I have sucked, but still large and circumcised. I genuinely love sucking his cock and swallowing his cream. This afternoon was no different. Cole loves my sissy role playing. He's all business, and once I finished, he left quickly, discreetly leaving my envelope on the table.

On his way out, he always says the same thing, "See ya sissy slut!"

Carson was my next client, and he was always fashionably late. That's cool, as it gives me time to freshen up. Carson is a laid-back and free-spirited man. He is 30ish with a full head of dirty-blonde locks in the classic quaff. His short stubble facial hair complements his chin and jawline.

He loves to kiss, which makes our sessions more intimate. I love to press my naked boobies into his bronzed muscular body. His cock fits nicely into my butthole. Today, he found my P-spot as he filled my ass with his cream. My cream squirted out too, soaking my lace panties. Yes, wearing chastity is both complicated and humiliating.

As Carson kissed me goodbye, he caressed my bare booty. He tightly squeezed my cheeks and remarked, "Nikki, I love fucking that gorgeous ass of yours! I can never get enough of you." As he left, he tossed my special envelope onto the sofa.

I heard my cell chime. Tommy sent a text, saying that Macy wanted to meet me. I quickly freshened up. Carson's cream was already dripping down my thigh. I found an anal plug in my bag, unfortunately, I did not have a fresh pair of panties to change into. Instead, with my already soaked panties, I cleaned my sissy clit, cage and inner thighs. I stuck my fingers in my mouth sucking them dry. I love the taste of my own cream. I hurried to meet up with Tommy and our new client.

Meet Macy Price

I found Tommy sitting with a stunning blonde at a corner table in the bar. Tommy motioned for me to join them. Their eyes were transfixed on me as I approached their table. As I sat in one of the empty chairs, Tommy introduced us: "Macy, this is Nikki, and Nikki, this is Macy."

The pretty blonde extended her hand, "I'm Macy Price. Nikki, aren't you just a pretty little thing? Gavin is going to love you! Nikki, can you give me a little twirl? "

Macy has one of those deep southern accents.

As I twirled to show Macy my body, I pushed down on my skirt hem, in an attempt to conceal my caged sissy clit. Apparently, I didn't hide my cage and sissy clit very well, as Macy remarked, "My, my, what have we here?" She tugged at my hem so she could get a better view. She tenderly ran her fingers along the silicone shaft.

Staring at Tommy, she spoke, "Tommy, where can I get a cage for Gavin?"

I started to chuckle, but Tommy interjected, "Macy, I will have one delivered tomorrow. We'll even have it gift wrapped in a pink box with a bow!"

Macy commented, "Sweet Gavin is not as big as our girl here."

As she placed her hand over mine, Macy replied, "Perfect!" Focusing on me, she added, "Nikki, sweetie, you are my hubby Gavin's 50

th

birthday present, but he doesn't know yet that you and I have an even bigger surprise for him. " I've role-played before, but this scene might be awkward.

Macy then interjected, "My dear, sweet Gavin is going to learn all about a

'Female-led marriage'

tomorrow."

Macy turned to Tommy, remarking, "Okay, Tommy, see you at Two O'clock tomorrow. I'll let you and sweet Nikki work out the details!"

She stood, hugged me, and when Tommy stood, they embraced. She whispered in Tommy's ear, "Melody has told me all about your cock too!" She squeezed Tommy's crotch area before she walked out. And all eyes were staring at her gorgeous booty as she strutted out. I was watching too.

Tommy Fills Me In

Once she was out of earshot, Tommy and I began to laugh. As we sat, Aaron brought us two glasses of Chardonnay. Tommy gave me the back story.

Tommy spoke, "Apparently Macy caught Gavin watching porn on the internet. He confessed that he fantasizes about shemale porn. There's more to his story, but Macy has looked the other way for several years. She's tolerated his infidelity."

Tommy paused, then added, "Macy says Gavin thinks he's a stud, but Macy says he just doesn't measure up. He's been unfaithful before. " He chuckled, "Using her words,

'It's time to take him down a notch!'

And you will play a huge role. "

I interjected, "So, my role tomorrow is to be his little sissy cocksucker?"

Tommy replied, "Not exactly. Macy has concocted a story that he's meeting you in the bar to fulfill his sissy shemale fantasy and as his birthday gift, you will take him to the playroom. Macy will already be waiting in the playroom."

He paused, then added, "Once you are both inside the room, Macy will inform him of the change in plans. And that she's in charge now. Apparently, Gavin has never said no to her!"

Somewhat amused, I responded, "Sure, Tommy, but are you okay with her plan?"

Tommy continued, "Amari and Melody, two of our good friends and customers, are their references. Amari tells me that Gavin manages Macy's family investment portfolio. If Gavin doesn't obey, their pre-nuptial agreement will devastate Gavin." Tommy smiled at me and added, "Macy has been unfaithful too. But Gavin has no clue. In case you need us, Amari and I will be enjoying lunch and cocktails in the restaurant."

I quickly surmised, that Amari has been tapping Macy's fine ass. I know all too well, having experienced his enormous cock inside me more than once. That's another story that hasn't fully been told yet.

Tommy, smirking, said, "Macy expects a lot of begging for forgiveness. She says Gavin's not a fighter, so he will acquiesce. The gift boxes will contain chastity, cuffs, an anal plug, and leashes. Just follow her lead, and you too will get to enjoy Macy's pleasures tomorrow. Macy told me that Melody speaks highly of you!"

I sat back in the chair as Aaron served us two more Chardonnays. I just smiled inwardly, I love cock, and I'm a terrific cocksucker. But I love pussy too. I've role-played the sissy and submissive roles. I've learned to enjoy the switch role when I get the chance. I'm looking forward to tomorrow. I just love side gigs too.

But Today Was Not Just Another Day

Today was the day that I would meet Gavin Price. Today was the day that Gavin would become enamored with a sissy named Nikki. Today was the day that Gavin will remember for a long time. Helping his wife, Macy, turn the tables amused me.

But first, I had to dress the part. If Gavin wanted a sissy shemale slut, then I had to dress like a surreal doll, a perfect blend of sissy and slut was required. I slipped into my favorite pink silicone chastity. I was excited, so I had to crunch my semi-aroused cock into shaft.

I framed the

cherry pink

chastity with more pink, a

Persian pink

garter belt with a shiny finish, and a matching low-cut uplifting bra with peek-a-boo windows and elastic straps across the bust. A pink leather collar with an O-ring completed the look. I set the matching pink thong next to my purse. Pink is my sissy color. This lingerie set says slut. There is nothing better than wearing a cute matching bra and panties set!

On my smooth legs, I slipped into

Foxy pink

silky, back-seamed thigh-high stockings. The back seams showcased my legs with a sheer, shiny appearance that makes the statement. So do the 3"

Barbie pink

stilettos. I twirled in front of the mirror. Admiring what I saw, I felt and looked sexy and demure. I can't lie, I enjoy the delicate and silky lingerie against my smooth skin.

My dress had to match the look. Hanging in my closet, next to all my sexy slutty outfits was the perfect short-sleeved tight

Dark Pink

semi-sheer stretch spandex mini-dress.

When I put on the mini-dress I turned into a cock thirsty slut. I was ready to make Gavin's day; the fantasy that he always wanted. Rose Pink lip gloss with glitter completed the look. There are so many shades of pink for the girly girl to wear.

I was very overdressed for a Wednesday afternoon. Grabbing my purse and travel bag, I quickly exited the door. As I drove Coastal Highway to Rehoboth, I was excited. My sissy clit was pushing against the cage restraints.

Setting the Stage

I arrived at

'Amazed'

on time, just enough time to get situated at my reserved table in the corner. Meeting a date outside of the playroom was unusual but today was different.

Aaron was again tending the bar. When he set the

Baby pink

Cosmos on my table, he blew me a kiss, remarking, " Pink is your color, Nikki! Sexy and slutty always sells!"

As if on cue, Macy and Gavin entered the bar. She wore a black leather skirt and a white, frilly, long-sleeved blouse. Macy also wore black nylons. She pointed Gavin toward me, then sat at the bar seat closest to the door.

Gavin is distinguished-looking, handsome but not hunky man. Seeing them together, Macy was much younger than Gavin. The attraction must be Gavin's money management skills.

As Gavin hurried across the bar, the smile on his face got bigger as he got closer. He extended his hand, "Hello, I'm Gavin, you must be Nikki?" I nodded. He paused, then added, "Nikki, may I join you?"

Motioning him toward the seat next to me, I remarked, "Please do, Gavin. A lady never turns down a handsome gentleman." Gavin sat, pushing his chair even closer to me. His back was to the bar.

Aaron quickly placed a Bourbon neat in front of Gavin, adding, "Compliments of the Lady sitting at the bar!" We raised our glasses to toast each other, then Macy, the lady sitting at the bar.

Gavin and I exchanged a get-to-know-you conversation. He kept telling me how stunning I looked, how pink was a perfect color for me. Gavin was infatuated with me. I loved it, and the more I flirted, the more I charmed him. For most of the conversation, Gavin's eyes were focused on my cleavage.

Aaron brought us another round. I took the distraction to squirm in my chair, to expose the lacy stocking top. When I crossed my legs, Gavin spotted my caged sissy clit. I flashed him on purpose.

He gently placed his hand on my thigh, tenderly rubbing his fingers along the stocking seam and garter tab. He whispered, "Nikki, your legs are gorgeous. You are everything that I wished for!"

I demurely smiled back and tilted my head to the side to encourage Gavin to kiss me. And we did. I placed my hand on his thigh, gently caressing his upper leg, pulling my hand back my palm grazed his now aroused cock. Staring into his blue eyes, I asked, "Gavin, is all that excitement for me?" Gavin smiled and nodded.

I paused and temptingly added, "Let's go somewhere to relieve the pressure in your pants."

Gavin quickly turned to ask Aaron for the check. Aaron waved him off, letting Gavin know the drinks were on him. Gavin placed a few

Jacksons

on the table. As I stood, I purposedly pulled on my mini-dress, to fully expose my caged sissy clit. Gavin's eyes were affixed on my crotch. I slowly wiggled to adjust my dress hem to cover my sissy clit. My facial expression showed embarrassment.

I quickly grabbed Gavin's hand, squeezing it tightly, remarking, "Come with me, Gavin, there's a perfect private spot through the doors. On our way out, Gavin did not notice that Macy was no longer sitting at the bar.

The Playroom Awaits

The keyless lock enabled us to enter the playroom quietly. Once inside, Gavin excitedly pressed my back against the inside wall. He hastily tried to kiss me.

I placed two fingers over puckered lips, softly whispering, "Gavin, let's take it slow!"

He leaned his head to the side to kiss me. I delicately kissed him on the lips. My arms were now around his neck, and I pressed my body against Gavin. Gavin hands held me at the waist, I could feel his hard cock, through his pants pressing into me.

Pushing back slightly, I whispered, "Gavin, let's get you naked!" As I walked toward the center of the room, Gavin followed me like a little puppy. He glanced at the pink gift-wrapped boxes on the tabletop, but did not comment. A

Hot pink

leash and handcuffs were coiled next to the pink boxes.

As planned, Macy is securely hidden in the small room that adjoins the playroom. When I stopped abruptly, Gavin bumped into me. I pulled my hair up. "Gavin, sweetie, help me unhook my dress."

As he unzipped the dress, I let it seductively drop to the floor, exposing my perfect naked booty framed by my garters and stockings. I quickly turned on my heels, now facing Gavin, his eyes were affixed on my caged sissy, my encased boobies. Picking up the

hot pink

leash, I attached the hook to the O-ring. I handed the other end to Gavin, adding, "Now let's get you naked!"

Gavin was mesmerized by me. His sissy shemale fantasy was real.

As Gavin gently pulled on my leash as I unbuckled his pants, letting them drop to the floor. I knelt before him to pull his boxers down his legs, his hard cock popped out nearly poking me in my eyes. Looking up, I focused my eyes on Gavin's eyes, and whimpered, as I ran my tongue along my glittered lips.

I quietly mumbled, "Gavin your cock is yummy! It's so big and hard!" His circumcised cock was chiseled, but not large. Sissies are allowed to tell little white lies. I tenderly kissed his cockhead. His body quivered as my lips touched his soft skin.

Kneeling in front of Gavin, I removed his shoes, leaving his ankle socks on. He kicked his pants and boxers to the side. Gavin tugged on my leash, pulling me up his torso. I hastily unbuttoned and removed Gavin's casual shirt. Except for his ankle socks, Gavin was now fully naked. He pulled me forward to kiss me again, his hard cock was pressed against my stomach.

Then the excitement started, but not the enthusiasm that Gavin expected.

Macy Enters Stage Left

Macy bursts through the side door. She had removed her blouse. She was wearing a gorgeous black leather under-bust corset, sans bra. Her boobies were exposed. She entered the room, talking directly to Gavin, "Sweetie, Nikki might be your desire, but today, she's here just to tease you!"

Gavin's demeanor immediately went into shock. He started to mumble, but no words came out. He glanced at me, then back at Macy.

Finally, he spoke, "Macy, what's this all about. We agreed! What's changed?" Macy was now standing in front of Gavin. Her facial expression was not joyful.

I quickly stood and silently made my way to the table.

Macy spoke, "Gavin, I have put up with your unfaithfulness for too long. Today, the tables are turned! My dear, sweet Gavin, today you will learn all about a

'Female-led marriage'

. We will be living under my new rules!"

He started to talk again, but Macy just said, "Stop! This is not your decision!"

I quietly handed Macy the handcuffs. Macy grabbed his wrists, quickly locking the cuffs.

As I unwrapped one of the pink boxes, Gavin tried to talk again, but Macy abruptly remarked, "Stop!" I handed Macy a ball gag.

I helped her affix the gag strap around his head, stuffing the ball inside his open mouth. The first box also contained a delicate

Sea pink

collar, fit snugly around Gavin's neck.

Macy turned to me, remarking, "Nikki, it appears that Gavin is now the perfect little sissy!" She unclipped the leash from my collar, rapidly hooking the leash to Gavin's collar.

Gavin's eyes were now staring directly into Macy's eyes. He was a little dumbfounded, perhaps embarrassed, and now helpless. Macy cupped Gavin's now flaccid cock and balls.

Inside the second box was Gavin's

Baby pink

silicone chastity. We both knelt, I spit into my hand and using Gavin's precum and my saliva I showed Macy how to securely cage his cock. Before she stood, she kissed his cockhead through the peep hole. Standing up, Macy fastened the key to the chain dangling from her neck.

Staring into his eyes, she spoke, "From now on I control when and if you will cum. Do you understand?" He nodded affirmatively.

She then added, "You will still get your sissy shemale birthday wish, but with a little twist." Macy smiled at me, then added, "Gavin, sweetie, you will get to watch Nikki, our gorgeous transwoman show you how to pleasure a woman!"

Macy gently pushed Gavin into the nearby high-back chair. I knelt to hurriedly restrain Gavin's ankles with the restraints that were hidden under the chair.

Before I could stand, Macy dropped her leather skirt to the floor, revealing her freshly shaved pussy. Her puffy labia lips were very inviting. I quickly crawled toward Macy, and she pushed my face into her sex.