Kinky Day with Stephanie

Nikki Spends Day with Stephanie and Grace

This is the third installment of Jamie's business trip to Seattle. Jamie was caught dressing femme underneath his male clothes by one of his best customers. Brian in Chapter One met Nikki for cocktails, terrific sex then departed Nikki's hotel room, vowing to return in the morning.

In Chapter Two he doesn't return alone. Stephanie, one of Brian's staff members joins them. Stephanie convinces Nikki to extend her stay in Seattle, accompanying her for the day and an evening of frivolity. Brian passes Nikki's chastity key Stephanie.

Nikki or Jamie if you prefer, lead a double life. She is gainfully employed as Jamie, a male marketing executive in the airline industry. Jamie travels extensively for business. When Jamie, err Nikki travel, she packs her male business clothes alongside of her feminine attire.

Jamie has been dressing as a femme since her college years. A limited few of his colleagues know anything about his alter ego, Nikki. Nikki emerges, almost daily outside of Jamie's work responsibilities.

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.

So, then the life story of Nikki Madison's Kinky Adventures continues by adding another episode, at this point in her life's journey.

Yes, we do have unfinished business, so I agreed to extend my Seattle stay at least one more day. Stephanie and Nikki will spend the day together. Stephanie will show Nikki the sights in the city, then a dinner at one of her favorite restaurants on the Pike/Pine Corridor in the Capitol Hill area. Dancing the night away is also a possibility.

Stephanie resides nearby and of course I will be spending the night. I have a late flight home tomorrow, that could also be extended one more day. But first we must clean up from an early morning tryst with her boss, Brian, Stephanie, and me.

Entering the hotel's bathroom together, Stephanie removed her red bra, then helped me out of my silicone self-adhering breast forms. Stephanie's boobies are gorgeous, nice and firm, with pink nipples. I plan to lick them later. My sissy clit was still encased in my white chastity.

As we entered the bathroom, I thought she set the chastity key on the countertop. Turning on the water, we entered the shower together, the warm water cascaded over our naked bodies. Pushing next to me Stephanie began soaping my back. I felt very relaxed with her soft touch and long strokes across my body. When she stepped closer, I felt her firm globes on my back, then her right soapy hand, reached around my body to softly caress my sissy clit, still caged. My clit was now twittering. I moaned softly at her touch.

Stephanie apparently had inserted the key in her left hand, as she reached around my waist with her left arm, and I felt both hands on the cage. I then felt the key turn in the lock, then heard a soft thump as she gently dropped the lock to the shower floor. Stephanie slid the silicone shaft tube off, gripping my sissy clit in her left hand, she dropped the silicone shaft. I whimpered. She then removed the ring from my balls. My sissy clit was now semi aroused in her soapy hands. She gently squeezed my sissy clit, turning me to face her.

She handed me the soap. I quickly rubbed the soapy suds all over her firm globes, gently pinching her pink nipples. Stephanie pulled me closer; my whimpers became moans. She slowly runs her fingernails lightly along my sissy shaft, then cups my balls. Stephanie leans in to smell my neck, pressing her warm, closed lips against my neck. She looked up to make eye contact, then gently kissed my neck again as she continued to squeeze my sissy clit.

Stephanie moved her mouth to my lips. I tilted my head slightly, matching Stephanie's open mouth, pressing our lips together, gently, then more firmly as we held the kiss. Stephanie, releasing from her grip my now aroused clit, whispered, "I want your cock in my pussy now Nikki!" I moaned. No one has called my sissy clit a cock in a long time.

I pressed my mouth firmly on her lips, pushing my tongue softly between her lips, tickling her tongue with the tip of mine; I parted our lips, looked into Stephanie's eyes, saying, "I want to be in you!" Stephanie moved her left hand to massage her clitoris as I slowly moved my right hand down to insert one finger, then a second into her vagina. She was indeed ready.

The warm water cascaded over both of us, I braced Stephanie against the shower wall, as she lifted her right leg for support on the shower bench, I slowly entered her pussy. Gentle strokes at first. Stephanie whimpered softly. I could feel the soft silky wetness of her pussy squeezing then releasing my sissy clit. My thrusts sped up to match her movements.

Stepanie murmured in my ear, "I need your warm cream deep inside me. I want it now!" Her whimpers turned into moans, then soft screams, "Now, now, Nikki now!" She took several deep breaths, then her breathing calmed down. Another orgasm for her this morning. First my tongue, now my sissy clit.

Regaining her control of my sissy clit, her pussy lips hugged my shaft tightly, as if she was milking me. Hearing her screams, I could not hold back, my legs buckled as my sissy clit twisted and turned inside Stepanie's pussy. I could feel my release. My arms tightened around her body; I too was totally satisfied. Calming myself down I softly kissed her neck, advancing my mouth to her lips, we kissed again, we held a long kiss. Stepanie and I had indeed established a new bond this morning.

Stephanie broke, the silence, "Nikki we need to dry off and get dressed! We have lunch plans."

Stepping out of the shower, I slipped back into my breast forms. Sharing my cosmetics kit, along with her purse cosmetics we both applied our make up to our faces.

Stephanie slid her red satin thong up her smooth legs, covering her bare pussy, adjusted her matching red bra over her stunning globes, she then wiggled back into in a tight black leather skirt, that fit snugly to her body, finishing with her white crop top, that showed a little bare mid drift. I grinned to myself, thinking the blouse was not suitable as office attire. She held her blue blazer in her right hand. She wore 3" red slingbacks.

I found a solid black lace push up bra and pantie set in my suitcase. She helped me with my high waist leather leggings. My bulge was not pronounced. I found a silk button down V neck tunic top blouse. I slipped on my 3" black slingbacks. We both looked in the floor length mirror, twirled together. We were eager to take on the day.

As I finished packing my suitcases. Since I pack for two people, Jamie, and Nikki, I always seem to have more than one suitcase. This trip was no different. I checked my briefcase, then my purse for personal items, sliding my chastity device and lock into my clutch.

Stephanie dialed the valet desk to have my rental car brought to the front. We made our way, down the elevator to the lobby, the bellman helped Stepanie take my bags to the front door to be loaded into my car.

I proceeded to the reception desk, to check out. When the front deck person pulled up my portfolio, she did a double take. I clearly did not appear to be Jameson Madison. She smiled broadly as she handed me my paid hotel charges with the zero balance, saying "I hope you had an enjoyable stay with us Mr. Madison."

I gave her a big smile back, reading her name tag on her uniform I remarked in my sexiest female voice, "Indeed I did, Amelia!" I winked further stating," I will be back soon." I strutted across the lobby to the front exit. I could feel her eyes staring at my booty, thinking to myself that's why I dress the way I do.

Stephanie had been handling the valet and bellman. My suitcases were loaded into my rental. As I arrived, I was again getting a few strange looks. I commented to Stephanie, "It's always interesting when Nikki departs instead of Jameson."

She grinned back at me.

I held Stepanie's door as she jumped into the passenger seat. I moved to the driver's side, tipped the valet again, then instinctively leaned over to kiss Stephanie full on the lips. I noticed both the valet and the bellman were staring at us.

Eyeing Stephanie, I said, "Where to girlfriend? BTW, where's your car?"

Stephanie commented, "I took a ride share this morning. We have plans so let's get some lunch, I am famished. I know a cute place on Capitol Hill."

We left the hotel heading north to the trendy Capitol Hill neighborhood.

Until now, our relationship had been all about business or sexuality. No in between, so it was time to get to know each other. I didn't even know her last name until now. We chatted about our upbringing, our education, our careers, and how we got to where we are now. Our journeys were similar, but clearly mine offered a different twist.

Stephanie is a University of Washington graduate, single, 23, living with another female friend, Grace, in the Capitol Hill area of Seattle. Stephanie and Grace are besties, who have sexually shared more than one partner together. Stephanie indicated that Grace works in the Capitol Hill area so she would be joining us for lunch.

Of course, she wanted to know everything about how and why I became Nikki. She was fascinated. She told me about Charlie, one of her friends, who had transitioned, but remained pre-op. She mentioned that we might see her later this evening. Arriving at the restaurant, Stephanie said she had twenty more questions, if I was willing to share, but could wait until Grace joined us.

I simply said, "Although Nikki is my alter ego, and clearly a secret with most of my work colleagues, I was an open book so to speak. I will gladly talk about Nikki!"

We valet parked my rental, entering the restaurant, Grace texted Stephanie that she was running a little late. We were seated quickly. I ordered a glass of Washington state Pinot Gris and Stephanie ordered a local Sauvignon Blanc. A mixed dozen of Olympias, Pacifica and Kumamoto oysters arrived as appetizers.

Stephanie reached across the table to hold my hand, smiling she remarked, "This morning was incredible Nikki. I want to get to know you better and of course that means intimately, too. So, what makes Nikki, Nikki?"

I nodded and simply posed a rhetorical question, "Where do I begin? Pausing, "I have three sisters, two older, Melissa and Megan and one younger, Amanda. My mother wanted four girls. I always thought I wanted to be a male, but I yearned to be feminine. I became torn so right now I can be both!"

I went on, talking about my Nikki beginnings, "At University at 19, I experimented more and more with wearing female clothes. I started with lingerie. I loved the satin and lacy ones and the different styles, low cut, high cut, even boy shorts. It seems like I have always been fascinated by the feel and texture of their clothes, especially their undergarments. "

Continuing, "My first lacy garter belt and stocking set "hooked" me for life, which made it more of a temptation to be a femme! My sisters caught me, didn't judge me, accepted the femme me, and helped transform my alter ego! I have become Nikki almost full time outside of work!"

As I was talking, Grace joined us at the table. She kissed Stephanie on the cheek, then leaned in to do the same to me. Grace was just as gorgeous as Stephanie. She was slightly taller, but that could be her choice of heels.

She appeared to be a true red head. She wore a cowl neck charmeuse blouse with blue denim skinny jeans. Her nipples protruded through the silk fabric, so she must be sans bra, and the jeans fit snugly encasing her legs and nearly perfect booty. She was wearing Black 3" stilettos.

Looking back at Stephanie, "Pardon me Nikki, but Stephanie there is no way?"

We both smiled at each other then as if on cue back to Grace. Stephanie spoke up, "Yes, girlfriend she is and Nikki, with her permission, will be our sex toy all weekend!"

I nodded affirmatively and smiled broadly at both women. Just then our waiter returned for our lunch orders.

Over lunch we talked about everything, lots of girlfriend talk; shopping, clothes, men, music, dancing, did I say men. I truly enjoy being treated like one of the girls. Then Grace addressed the white elephant at the table ... me and my little secret.

Looking straight at me, "So Nikki Stephanie tells me that you are submissive? I believe her words exactly was that you are a sissy sex toy!"

Being a little embarrassed and averting my eyes, I nodded affirmatively.

Grace grinned mischievously at Stephanie, then back at me, asking, "Besides your chastity, did you pack any other toys with you?"

I nodded, negatively.

Grace continued, "Very well, Stephanie and I are very happy that you are staying with us. Tonight, we will dine out then dinner and dancing at our favorite club however from this point on you will need to follow my lead. Do you understand what I am asking Nikki?"

I glanced at Stepanie for guidance.

She looked back at me, saying, "Yes Grace is my Dominant. We want to invite you to be of service and pleasure during your stay with us. It will be fun, and I assure you the sex will be terrific!"

I looked back at Grace, remarking, "Yes Grace, it will be my pleasure to serve and service you and Stephanie!"

Reaching under the table, placing her hand on my crotch, Grace smiled broadly, "Yes, I see you are now excited. Do you have your chastity with you, now?"

Feeling even more humiliated, I tried to reply, but could only nod affirmatively.

Grace spoke up, "Stephanie, take the sissy to the ladies' room, help her fix her hard-on problem, then refit her chastity!" Checking her phone, "It's getting late. We have a little shopping to do before we go out tonight. I will take care of the check!"

Stephanie immediately stood up, grabbed my hand, leading me away to the ladies' room. I grabbed my clutch, stumbling trying to keep up with her.

Out of the corner of my eye, I saw Grace motion to the waiter for the check.

Stepanie, pushing the door open, tugged on my hand, to follow her into the room. She locked it behind us. I had 20 questions for her, but Stephanie placed her forefinger in front of her mouth, silencing me. She then held both of my hands.

Staring at me sternly, she quietly said, "Do you trust me? Are you good with the arrangement?"

I nodded approvingly!

She then locked the door behind us.

She then ordered me to drop my leggings and panties.

I wiggled out of my leggings, letting them plunge to my knees. Stephanie pulled down, my lace panties, my fully aroused sissy clit popped out. Stephanie knowing how impatient Grace can be, began stroking my clit.

I began whimpering. Stephanie increased the pace, stroking my shaft more vigorously as my whimpers became louder moans. She leaned down, inserting my sissy clit fully between her lips. Cupping my balls now, she squeezed hard, as I spurted my heavy load in her mouth. She swallowed it all.

Fingering her mouth, she inserted her fingers in my mouth. I licked them dry.

If I hadn't been humiliated before, I was now. She sucked me off in less than 60 seconds.

She squeezed my now softening clit, as I handed her my purse, squatting she pushed my balls through the chastity ring, the slid the silicone tube over my now flaccid shaft, slipping the lock through the two slots fastening it in place, she then secured the lock with the key.

She smiled up at me, as she sucked the silicone chastity shaft, she then rolled my panties back over my cage, fitting my sissy clit snugly. I wiggled back into my leggings.

Stephanie padded my now crotch eyeing me, saying "Nikki your sissy clit bulge is so sexy!" She then grabbed my hand, leading me out the door,

Grace was waiting for us on the sidewalk at the valet stand, my rental car parked immediately behind her with the valet holding the open doors.

Grace, seeing my prominent sissy bulge, she grinned, commenting in a voice, louder than I desired, "Nikki, your sissy bulge is so cute!"

I walked around to the driver's side, as the valet handed me the car keys, he saw my noticeable bulge for the first time, he smirked, saying "Are you really a boy? You could have fooled me!"

Stepanie climbed in the back seat; Grace sat next to me. As I turned the key, I turned to Grace, Asking, "Where to now, Grace?"

Grace spoke up, "We have one stop before we return to our place. Turn right at the next corner, we are headed for the fetish store. BTW Nikki, from now on in private you will act and do as Stephanie does. You will refer to me as Mistress Grace!"

I quietly nodded my head in agreement, "Yes Mistress Grace!"

The Fetish Store is just a few minutes from the restaurant. The store is an upscale fetish boutique owned by Charlotte, a close friend of Grace and Stephanie. Charlotte also owns a Fetish and Dance Club nearby.

During the short drive to the Fetish Store, Grace outlines our activities for the rest of the afternoon and evening. At the store, we will be purchasing a few items, for me, Nikki, then to Grace and Stephanie's house to freshen up before dinner. After dinner, we will go to Charlotte's Fetish and Dance Club for a little cavorting on the dance floor and private rooms, then home to become more comfortable.

I pulled into the parking lot next to the store. Grace glanced back at Stephanie, saying, "Are you now wearing your pearl choker Stephanie?

Stephanie quickly responded, "Yes Mistress!"

Exiting the car, Grace, removing a gold chain from her purse, turned to Stephanie, clasping the chain to a hook on the pearl choker. I gulped. She led Stephanie into the store, freezing me in my tracks. Grace, looked back at me, saying," Come dear Nikki, keep up!" I hurried in behind Grace and Stephanie.

Stepping inside the store, I was overwhelmed. It was not your typical fetish store. It was a high-end fashion boutique that also sold various types of sexual paraphernalia. There were a few dressing rooms in the back, accompanied by three diagonal floor to ceiling mirrors. Two doors, with the words, "Private" on the gold plate were to either side adjacent to the dressing room area.

In the center of the store there are two couches, with a small podium in the middle. Several stools were strategically placed around the room.

Grace and Stephanie were greeted a lady in all pink, "Welcome back Mistress Grace and Stephanie!"

Grace acknowledged, the lady in pink, "Good to see you again, Elizabeth, is Miss Charlotte here today?"

Apparently, hearing the voices, a stunning woman, in black leather pants and knee-high boots emerged through one of the "Private" doors. Charlotte is a very striking blonde, with a very deep neckline in her black silk blouse that concealed her firm round boobies. Charlotte's face was exquisitely beautiful, her beaming smile was one of her best assets.

Elizabeth quietly moved to lock the front door, placing a sign in the window that read 'Private!'

Walking directly to Grace, she hugged and kissed her, then immediately hugged and kissed Stephanie. Stephanie stepped back, as Charlotte extended her hand, for Stephanie to kiss her hand. She bent slightly to kiss the top center of Charlotte's hand.

Kissing one's hand is a gesture of courtesy, respect, admiration, and extreme politeness. It also denotes that Charlotte has a higher social status.

Seeing me standing behind the two women, she noticed me, "What have we here, Grace?"