Nikki - Cheers to New Beginnings

Prelude to New Year's Eve Auction

This installment is the final stage in the evolution of Jamie's journey. Nikki or Jamie if you prefer, has led a double life. He was gainfully employed as Jamie, a male marketing executive in the airline industry. Jamie has been dressing as a femme since his/her college years.

He has risen through the executive ranks as a marketing executive for an airline. Due to the international nature of his role within the company, he has been able to live in various locations throughout the country.

After brief stints in California, Arizona, and Texas, he moved back to the East Coast to be closer to my family for their support and guidance. When he moved back, he met his wife Ashley, as Nikki, Jamie's alter ego. Nikki was serving a dinner party.

As Nikki/Jamie they spent time together, then marriage, unfortunately, or fortunately, an amicable divorce. She was openly female with her and their friends, always working as a male during the day then all female when not at work. Of course, a power exchange existed.

After the divorce, she, Nikki, found strength in her divorce process, gaining a great deal of experience and courage in the exchange. she was able to transition to full-time girl, living and working as a female.

Resigning from the airline, and well-off financially, she eventually left the Annapolis area to live and work in the beach towns on the Delmarva peninsula. This area is defined as portions of three states that encompass Chesapeake Bay's Eastern Shore.

Nikki moves in with two bisexual men, who own and operate several restaurants and bars in the resort towns along the Atlantic coast. She works as a Bartender, Hostess, Event Planner and Escort. Nikki has chosen to remain Pre-op.

This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. Most of her family and close friends, with the benefit of being able to comprehend and appreciate her exploits, are aware of and love her.

Any similarity to any individual, living or deceased, or any location, is purely coincidence and unintended. Jennifer Nicole is very cognizant of the importance of safe sex. She uses a highly effective preventive medication that reduces her and her partners' risks for disease.

The life story of Nikki Madison's Kinky Adventures continues by adding another chapter, at this point in her life's journey. This episode is out of sequence of her full-time transition but is very seasonal in nature.

Beach Bound in The Fall

The off season, November to March, at the Mid-Atlantic beach resorts is always a little slow. The high season summer months June, July, and August are booming. September and October, the second season, are slower months at the beach, but cold weather creeps in beginning in November through February.

The beach nightlife slows to a crawl, until March launches the ramp up to the summer months. So our annual seasonal beach cycle begins again.

During the winter months I can slip away to warmer weather to visit with my kinky family and friends. I may take a few quick trips in November and December, but I always stay around until New Years.

Sure, the locals always stop by our restaurants and bars, but the number of partygoers does not compare to the peak months. During the holidays we do get a bump and New Year's Eve has become a huge event night for our restaurants. At the LBGTQ restaurant, that my two guys own, we hold our Annual Kinky Charity Date Auction.

It's a private event, by invitation only, that includes dinner, dancing, cocktails, with a Kinky Date Auction beginning at 10 PM and ending at midnight. A silent auction of also offered. It's a Gala Event attended by many in the community.

The Auction raises money for several local LBGTQ charities. Individuals, men, women, and couples volunteer themselves and/or their services to the highest bidder who will donate proceeds to charity for the privilege. Each consenting adult volunteer provides a synopsis of the fetish type services they will provide to the winning bidder.

This is the fourth year that I have participated as a consenting volunteer. The first time, my kinky maid services were offered through the silent auction. After receiving a sizable charity donation, I was elevated to the Charity Date Auction. I have become quite popular. I am proud of that as 100% of the Auction proceeds go to a good cause here in the community.

Over four years ago, after my divorce from Ashley, I started a catering and events business. Our separation was amicable, and I must say I financially benefited, but that's a story for another day. The divorce led to many changes in my life, a change in careers, and a complete change in lifestyle as I transitioned to living as a full-time female.

Some of my best feminine body features have come to me genetically, but I don't do things halfway, so to be more feminine, I started with silicone breast augmentation and jaw and chin facial feminization surgery. Other minor surgeries may come. I chose to remain pre-op. I must say, I have been told I have an incredible figure. I blush every time someone mentions my beauty.

One of my close friends Tommy, who owns several restaurants with his partner Ralph, after a competitor opened a new nearby restaurant four years ago, called me out of the blue. The new restaurant "stole" several key people at the beginning of the summer peak season. Tomy and Ralph were in urgent need of temporary assistance.

My catering and event business was struggling, so when Tommy invited me to come to the beach to work temporarily for him, I jumped at the opportunity. I was clearly in need of a change of scenery.

My temporary agreement has now turned into full-time, evolving into event and private party work, bar management, and bartender during the peak season. I also live with Tommy and Ralph, providing pleasurable service and services as their live-in sex toy.

That's a short version of how I got to the beach, so let's talk Auction.

Prelude to the Annual Auction

The countdown to the Annual Kinky Charity Date Auction has begun. Pictures of the consenting volunteers have been posted in the restaurant. This year, we have six participating consenting volunteers for the live auction. Two males, one individual female, a male and female couple, a female couple, and me the sole transgender. Next week the kinky services synopsis will be added to peak interest.

The silent auction has seven volunteers offering services ranging from maid to special event services. The year I did the silent auction I offered sissy maid services.

The last two auctions I offered undefined "Toy" services. Last year a couple were my winning bidders, with a record donation. The one-day commitment led to three wonderful pleasurable days. Hopefully they will be the winning bidders again this year.

For the next two weeks I will be bartending during the peak nights at the bar. During the winter months I wear mostly spandex leggings and bodysuits, that showcase my perky booty. Heels always enhance my legs too. Tight sweaters show off my gorgeous globes.

If it's warm enough, I trade in my sweaters and leggings, for short skirts, and low-cut tops. I always wear sexy lingerie. I adore the feel and the touch of silk, or satin, or lace, or spandex, on my body. On occasion you might see my sissy clit encased in chastity without panties.

I am always horny, as the thrill and sexual sensation engulf my mind, core, and spirit every day.

Tonight, I worked the early evening shift. Aaron the second bartender will close. It was a little chilly, so I slipped into black scrunch bum glossy high-rise leggings, with pullover sweater V-neck jumper. My lacy black underwire bra was visible underneath. When you flash a little lace, the tips are more generous. Once I got to work, I self-locked into a black silicone chastity cage.

For a Tuesday, tonight was busier than normal for the off season. A few regulars, a few new customers. Then, last year's winning bidders Melody and Amari popped in. Before they sat at the bar, we exchanged hugs and kisses.

Melody's arms circled my waist, as she kissed me on the lips, she commented, "Nikki, you are looking gorgeous as usual."

A simply blushed, trying to speak, but Melody kissed me again full on the lips, whispering, "I want your tongue between my lips!"

I tilted my head and pushed my tongue into her mouth, but Melody pushed back, smirking, "I love kissing you Nikki, but I need your tongue much, much lower."

She beamed into my eyes as her left hand found my caged sissy clit in my leggings. She gently rubbed me through the spandex, "Just the way I like you girlfriend!"

Amari stood patiently behind Melody, waiting for his turn for hugs and kisses, so Melody stepped aside, to let Amari get his hugs. He pressed his firm athletic body against me, his manhood pushed against my stomach. Doing so, he caressed both booty cheeks with his huge hands. Whimpering at his touch, I looked up as he stared into my eyes with his gorgeous brown eyes, grinning, "That's how much I want your boi pussy Nikki!"

I smiled back, commenting, "Amari I started to drip as soon as you and Melody walked through the door." Before I could finish speaking Amari ran his finger up the back crease of my leggings, then licked his lower lip with his tongue. I melted into his arms.

I then heard Aaron mischievously speak, "Melody and Amari its good to see you again." Gesturing to the service area of the bar Aaron added, "Nikki has other customers to tend to. What do you guys want to drink tonight?"

I scurried off to the other end of the bar, to tend to the wait staff's customer drink orders.

From time to time, I glanced at Melody and Amari; I thought to myself, they are a stunning couple.

Melody is an energetic blonde, with the classic blue eyes that mesmerize you. In heels she's a little taller than me. She has long athletic legs, a toned body, her boobies are large, hard, and firm. Much more than a mouthful. Tonight, her gym toned booty fit snugly in her red spandex leggings. The black low-cut silk blouse extenuates her large firm globes. She was braless tonight with her nipples poking through the silk. Her classic round brilliant and pear-shaped diamond ring glistens on her ring finger. That's truly a fine piece of jewelry.

Amari is a tall, muscular athletic black man. His body is fit and trimmed and simply magnificent. I love embracing his carved athletic body. I remembered that his cock, oh his cock, is outstanding. It's long and thick, with a large, mushroomed head. I adore how he expertly uses his cock inside all my holes.

They bought me at last year's Auction for a generous donation to the Charity. I was obligated for 24 hours, I stayed 72 hours.

Amari is a former pro football player, now an attorney representing athletes. Melody is an interior designer. They have a beach house in a nearby coastal town, but their permanent residence is in the Maryland suburbs of our Nation's Capital. When they are at their beach house, I have been invited to become a house guest, bed mate and sex toy.

When the bar activity slowed down, I returned to chat with Melody and Amari. Melody apologized for no advance notice for this trip, then asked if I was available after work. I commented that Aaron might hook up, but grinning back at both Melody then Amari, I simply said, "He will understand that you need a raincheck!"

Melody smiled back, glancing at Amari, "He is a hunk, perhaps we can do a foursome? "

Amari interjected, "I will invite Aaron for another night." Looking directly at me "Nikki, we want your sweet ass to ourselves tonight! We may even have a few surprises for you!" Amari swiftly moved to the other end of the bar, to talk with Aaron.

Amari, returning from his chat with Aaron, said to both of us, "Aaron good for tonight, Nikki."

Melody remarked, "With that done, Nikki will join us. What time do you get off?

I nodded yes, saying, "I need to talk with Aaron!" Adding, "However, I work tomorrow night!"

Amari, laughing added, "That is terrific. I invited Aaron over tomorrow. He will be there a little after Noon. A little sex play before you head off to work Nikki?"

Aaron joined us, at our side of the bar. I was leaning, against the cold cabinets, Aaron, stopped behind me, placing his hand on my right booty cheek, chuckling "Nikki is irresistible, so you can have her tonight,"

Then grinning at both Melody and Amari, "I will love to join both of you tomorrow!" As he walked away, he winked at Amari remarking, "I have heard so much about you two!"

The drink orders got a little busier, so Aaron and I had to hustle to catch up. When I could catch a breath, I returned to chat with Melody and Amari. They needed to leave, so I closed out their tab, Amari gave me an extremely generous tip, remarking that I should share it with Aaron.

I thanked them both, gave them big hugs again, Amari spoke up, "What time can we expect you, Nikki?" He squeezed my booty again, "Don't forget to give Aaron our address!"

I beamed back, "I can leave in about twenty minutes, Aaron is good with that and will close up!"

Amari and Melody left, waving good night to Aaron.

Aaron came up behind once again. As he caressed my booty, once again, he whispered into my ear, "Enjoy yourself tonight, Nikki! Don't you spend a lot of time at their house when they are in town?"

I wiggled my booty to the movement of his full hand, looking back, I smiled remarking, "Yes, I do. It's always delightful to be their toy!"

Aaron, turning me around to face him, smirked, "Is it true that Amari is huge!"

I beamed back, "You will find out tomorrow afternoon!" Winking, as I walked away, I said, "He is much bigger than you Aaron!"

Aaron stood there with his mouth open, as I tossed my bar rag in his direction I said, "When you show up tomorrow, bring me my share of tips. Thanks for letting me leave early! "

I grabbed my purse from the bar cabinet, smacking Aaron on his tight butt, I walked through the kitchen, then out the rear door to my car.

Overnight Stay with Melody and Amari

My drive to Amari and Melody's 5-bedroom beach house, near Silver Lake took only a few minutes. Since I was always taught to be prepared; I grabbed my overnight bag from my trunk, I hurried to the front door.

Greeting me at the front door, Melody, was now dressed in a full sheer black night gown, without panties, her bare pussy glistened, as her stunning globes pushed the sheer lace bodice.

I dropped my bag, then Melody and I fully embraced.

Melody, whispered in my ear, "Amari is waiting for us in the family room! We have a surprise for you."

She took me by hand, directly to the family room. Amari was sitting in black silk pajama bottoms in one of the overstuffed armchairs. He was naked from the waist up showing his muscular upper torso. When he stood to hug me again, I could see the outline of his huge manhood in pajamas. We embraced. I thought to myself, soon that will be inside me.

On the table in front of the four chairs were five packages in pink wrapping paper with white bows. Melody smiled me, "The gifts are yours Nikki, open your presents!"

I knelt next to the table, next to Amari, demurely looking at Amari as Melody handed me the first wrapped gift, saying, "Open this one first!"

I meticulously untied the ribbon and bow, setting it aside, quickly removing the wrapping from the box. As I removed the box top, I smiled. Nestled in the tissue were three graduated pink gem glass anal plugs in varied sizes, with a tube of lube and anal douche.

Smiling at Amari, I pulled out the largest plug. He grinned back at me, saying, "We need to warm up your butthole Nikki!"

I rose, handed the largest plug and lube to Amari, then turned around with my booty facing Amari. Melody helped me wiggle my leggings down. I bent at the waist, pushing my derriere up. I gasped as Amari pushed two lubed fingers into my hole. I took two deep breaths as he twisted and turned his gooey fingers in and out of my butthole.

I then held my breath as Amari slowly forced the plug in deeper. I whimpered as the plug slid in as deep as it would go. Amari held me by my hips, saying, "Melody I love the sparkle, show Nikki yours!"

Melody lifted her nightgown, showing me her booty. She modelled a rose colored glass anal plug. Turning back around, she beamed at me, "Amari has promised that he will let you pleasure my butthole too!"

She picked up the white bow and ribbon, wrapping the ribbon around my waist placing the bow on my caged sissy clit, then added "Nikki, your sissy clit is stunning adorned in black and white!"

I beamed, "How apropos!"

Amari, smiling, added, "Yes Nikki, you are well suited nicely between black and white!"

As I knelt, to open another gift, I slid my leggings down to my ankles. Melody handed me the next gift to open. Again, I meticulously untied the ribbon and paper, there were three jewelry boxes inside a slightly larger box. Opening the first box I squealed, lifting out an elegant sterling bubble necklace with a signature O-ring closure. Dangling from the O-ring was a heart tag that read, 'Sex Toy'.

Excited, I immediately brought the choker to my neck. Melody helped me fasten the clasp. It rested elegantly on my collarbone. I was thrilled, overjoyed with excitement.

Melody said, "Open the other two boxes!"

Digging deeper in the tissue paper was a second velvet box, nestled inside were a pair of matching diamond earrings. Melody helped me remove my diamond studs, as I inserted the new pair. I continued to giggle with excitement.

There's more, the third box contained a matching sterling silver leash. I was flabbergasted, I embraced Melody who was kneeling next to me. She handed the leash to Amari.

Amari gestured to me to come closer to him. As I knelt before him, he clasped the leash to the collar's O-ring, adding, "Nikki there is great symbolism of the choker chain. It represents power, dominance, and sexuality, which embodies style, confidence, and individuality. You own all these characteristics."

I giggled again with excitement moving my arms back and forth and up and down.

Melody, added, "Nikki, for me the choker signifies secret lesbianism and not-so secret prostitution. To me, girlfriend you are all that and more." Melody leaned in to kiss me, I twisted my head, to kiss her back firmly on her lips. We continued to embrace.

Amari, light tugged on my leash, "Come here pet, we do not own you, but we want you know how much we appreciate you. "Amari embraced me with his muscular upper torso, kissing me fully on my lips.

Melody then interjected, "Nikki, you have more gifts!"

I stared to move away from Amari, but with his big hands, he held me by my hips, saying, "Remove your blouse, I want you vulnerable!"

I held my arms up high and Melody standing beside me helped me out of my pullover, tossing it to the floor beside us. I stood before Amari, with my leggings around my ankles, my sissy clit encased in a black silicone chastity cage, adorned in a white bow and ribbon, my lacy black bra that encased my own gorgeous boobies and an elegant choker and earrings.

I beamed at both Amari and Melody, "Yes I am your sex toy!"

Amari cupped my boobies, pinching my nipples through the lace fabric, "Nikki you are a perfect little slut, and you are ours tonight."

Melody, stood beside us, caressing my booty with one hand, the other firmly squeezing my sissy clit through the ribbon and cage.