What Happens Stays a Secret or Not Transgender & Crossdressers

What Happens Stays a Secret or Does It!

It’s Trade Show Season. Jameson and his sales team attend the largest trade expo in the sports business. His airline is a major promotional partnership sponsor providing travel services, hospitality suites and exhibition services. There is a team of fifty colleagues that converged on Miami Beach Convention site.

All the major brands support and attend the Convention. Worldwide industry leaders, business icons, professional sports stars and agents, and top experts are in attendance. Team, ball, winter and racket sports are all showcase. It’s a must attend event for Jameson and his team.

Jameson always arrives a few days before the Convention for a little R&R and private meetings. Once the Convention opens the days and nights are long and extremely busy. Jameson stays in South Beach at a trendy boutique hotel that is a colonialstyle facility unique from the Art Deco hotels, restaurants, and bars that is prominent in South Beach. He adores staying at The Dakota on Ocean Drive; it’s not far from The Carlyle. Jameson also prefers the more intimate bar at The Dakota. He’s familiar with the hotel staff and many of the bartenders. They love Jameson and his alter ego Jennifer Nicole.

Let’s step back to set the stage for the first time readers of Jennifer Nicole’s journey.

So How Did Jameson and Jennifer Nicole Get Here?

Jameson is gainfully employed as a male marketing executive in the airline industry. He has risen through the executive ranks as a marketing executive for the airline. He travels extensively in North America and Europe for business. Originally based in San Francisco for the airline. He currently resides in Dallas. Since his college years at UMD an alter ego, Jennifer Nicole has evolved.

During all the years he has worked in the airline industry as a male during the day, all other times his alter ego, Jennifer Nicole comes out to play. Jameson travels, with his male business clothes packed alongside Jennifer Nicole’s feminine attire. A limited few of his colleagues know anything about his alter ego Jennifer Nicole, who emerges almost daily outside of Jameson’s work responsibilities.

This contains ual activities and situations between consenting adults. All characters are above the age of 18. Any similarity to any individual, living or deceased, or any location, is purely coincidence and unintended. The life of Jennifer Nicole Madison’s Kinky Adventures continues by adding another episode, at this point in her life’s journey. From now on, the will be told in first person.

South Beach is Always Fun

The staff at the Dakota is always professional, efficient and discrete. Arriving at Reception, Gabriel, greeted me, “Welcome to The Dakota Mr. Madison. I see that you will be staying with us for six nights. We have reserved a room for you with overlooking the courtyard. “

I nodded affirmatively, “Yes, that is correct Gabriel.” I remember her from previous visits, and she obviously remembered me, but I am sure my guest profile refreshed her memory. When I am in Miami Beach I almost always stay at The Dakota.

Gabriel added, “Mr. Madison, will you need two key cards? Also, will Miss Jennifer be joining you during your stay?” I nodded affirmatively. “As in the past, will Miss Jennifer have the ability to charge to your room?” She handed me two key cards. “Enjoy your stay with us Mr. Madison; Rafael will help you with your bags.”

The Dakota is a relatively small Hotel, with about 120 rooms and suites, located on Ocean Drive, not far from Collins Avenue. The rooftop pool and terrace bar have sweeping vistas of the Atlantic Ocean and South Beach. The hotel has two restaurants, one formal, one casual and a very intimate off the lobby bar. I have always enjoyed my stays at The Dakota.

Once in my room, I quickly changed into my Jennifer Nicole persona. It’s a gorgeous afternoon to catch a few rays at the pool. I applied my casual makeup, my teardrop adhesive breast forms, then donned my skyblue onepiece bikini with a highcut design. Decent coverage in the front, with a low cut back that is minimal but daring. A matching little skirt will help hide my bulge too.

Sun and Fun on the Rooftop

The sun was warm on your body, it wasn’t a summer sun basking day, but the views towards the ocean are magnificent as were the few lovely females sunning themselves at the pool. One or two couples. One single man, he is one hunky black male reading a book on a lounger in the corner. He was definitely eye candy too. I found a lounger situated in the middle. The pool was not crowded.

Hurley, the bartender made his way over to me. Recognizing me, he said, “Good afternoon Miss Madison, may I get you a cocktail?”

“Hurley don’t be so formal, It Jenn or Jennifer. A Malibu Sunset will be yummy today.”

“Yes Miss Jennifer!” Hurley hurried off, retuning quickly with my pineapple, orange juice, coconut rum, grenadine, and cherries cocktail. It looked yummy and was.

I read my book, sipped my cocktail, then rolled over to get a little bronze on my back. I fell asleep. Sometime later, I felt a presence lurking over me. Startled I jumped pushing myself up with my elbows. Standing over me was the hunky black male who was reading his book.

“Sorry I did not mean to startle you, but you might want to put some lotion on your lower back. BTW, my name is Lincoln Carey. I am staying here at the hotel too.”

I felt a slight tingle on my skin I reached into my beach bag, all I could say was, “Thank you.”

Lincoln seeing that I was going to have some difficulty applying the lotion, “May I help Miss…?” with his huge hand, he reached for the lotion tube.

I interrupted him, “I’m Jennifer or Jenn! Absolutely you can!” Of course, who would not want those huge muscular hands on their body. I stretched out, giving Lincoln full access to my back. He started applying the lotion on my lower legs, raising each leg to have better access to my thighs and calves. His touch was soft and gentle. He lightly but firmly applied lotion all over. I tried to hold back my moans. I wasn’t very good at it. Lincoln knew how to give a girl a massage.

Lincoln broke the silence, “Jenn, if I can be so bold, your booty is nearly perfect. Do you work out regularly?” I hope that when he lifted my legs that my bulge wasn’t exposed. Oh well, too late now if it was.

Between moans, I mumbled, “Yes I do. I try to go to the gym 4 to 6 times a week. It can be difficult sometimes when you travel as much as I do.

He added, “I travel a lot now too. When I was playing, I worked out daily. Since I retired it’s much more difficult to keep my routine..” Ah, the name finally registered, Lincoln Carey played professional football for one of the East coast teams. I think he was on a championship team.

Lincoln grazed my booty with his hands, as he started to apply lotion on my lower back, running his gooey fingers cup my neck. He ran his fingers in circles. I quietly whimpered at his touch. My cock was now almost fully aroused.

Hurley stopped by. We ordered two drinks and a small cheese platter. Lincoln spoke, “Hurley, please put everything on my tab.”

I turned over to sit up. Lincoln held my hand, helping me. I bunched my cover skirt onto my lap, trying to hide my aroused cock. I am almost positive Lincoln now got a glimpse of my bulge. If he didn’t he didn’t let on.

Hurley returned with our cocktails and snacks. Lincoln and I chatted for some time. He is also attending the Sports Convention. He is one of the professional stars that promotes a major athletic ware brand. I said I was also attending, but I was very fuzzy in what capacity. Lincoln didn’t push my vagueness.

It was getting late; a little chill was in the air. Lincoln glanced at his watch; it was a luxury Swiss watch. He smiled at me, then spoke, “Jenn I have a few phone calls to return. I have enjoyed getting to know you. Will you join me for a cocktail before dinner, and if you don’t have dinner plans, I would love to buy you dinner here at the Hotel? I have dinner plans with another couple, will you join us.”

I hesitated to answer, then replied, “I would love to Lincoln. What time do I need to be downstairs?”

We both stood, we embraced, I either inadvertently pushed my lower torso against his body or he knowingly pulled me into him. I know he felt my still aroused cock. Lincoln reached cupping my balls and aroused cock, whispering in my ear. “Yes I suspected Jenn! I adore girls like you. Does 6:30 at the lobby bar work?”

Catching my breath I replied, “Absolutely Lincoln!” He gave me peck on the cheek, as he squeezed my balls again. I added, “See you at 6:30 Linc!” As I walked away I swayed my hips, so he got a perfect view of my booty.

Get Ready For Tonight

Meeting someone like Lincoln Carey is exactly why I stay at The Dakota. He’s handsome, muscular, gentle, and I love big cock. He couldn’t hide his package in his bathing suit either.

Back in my room, I wanted to masturbate but I did everything I could not to. I did find the biggest anal plug in my luggage. I quickly lubed my butthole; I popped the plug inside me. I gasped. I want Lincoln inside me tonight.

Makeup time. I needed more than a refresh, so I went through all my steps. I needed to look sensual, not slutty for my dinner date with his friends. I readjusted my breast forms, slipping them into a leopard print bralette with crystal rings, champagne flower crystals, and tiny bronze sequins. I love the sparkle. The garter belt and thong matched. Since we were in the Art Deco capital of the world, my silky sheer shiny finish thigh highs added a retro style look.

I still get tingles through my entire body when I roll a pair stockings up my smooth legs; when I attach the stockings to the clasps on the garter, my cock always becomes semi aroused. I changed my mind, I removed thong. I tossed the thong towards my purse. Black men love white bitches like me in chastity. I selflocked my black silicone chastity cage over my cock. Tonight, I will be his white sissy slut. So, I dressed the part. Chastity makes me willing to do anything! That’s a given!

My black sheath high neck satin dress was perfect for tonight. It stretched across my body perfectly, my breast forms were not exposed and the slit on the side highlighted my legs and exposed the lace top of my retro thigh highs. Diamond studs finished my look. My chastity key hung on my silver necklace hidden by the high neck.

I never regretted putting on a dress, a silky gown, or lingerie. There is nothing better than wearing a cute matching bra and panties. Then when you add garters and stockings there was no going back. I felt a slight twinge in my caged cock. I was in heaven tonight.

I was ready, I did a twirl in front of the mirror. Perfect! I was a stunning woman tonight. I stuffed my thong into my clutch. I proceeded to the elevator and down to the lobby.

Cocktail Time

At night, the lobby was busy. I got more than a few looks. Mind you the stares were not is this boy dressed as a woman but who is that stunning woman strutting across the lobby. And I did, I was confident, and I owned this y look this evening. Lincoln was seated at the bar.

He stood as I approached. He held my hands, kissed me on the cheek, whispering in my ear, “Jenn, my little white bitch cleans up pretty good!”

I squeezed his hands, smiling, I replied with, “Thank you Linc.”

He tightly returned my squeeze, then sternly spoke, “In public, it’s always Lincoln to you little bitch. My wife is the only one that calls me Linc.” My smile turned into a slight pout; Lincoln had just put me in my place. He set the control in his favor. He then spoke to Grayson, the bartender, “The lady will have a Manhattan straight up.” Lincoln motioned me to sit. A straight up Manhattan is strong, smooth, and potent.

BTW Lincoln is very handsome tonight, dressed in black suit silk shirt, sans tie. He’s wearing a different luxury watch. He’s flashing a huge, studded ring on his left hand. Very Miami Beach. We chat for a few minutes. His friends join us. He introduced Baldrick and Cameron to me. No last names. I am introduced by Lincoln as Jenn, a friend from Dallas that he has known for some time. Baldrick is also a handsome black man, muscular and most likely a former pro athlete. I couldn’t place him yet. Cameron is a stunning leggy white woman, dressed in a silver glittering short mini, that barely conceals her ample boobies. I am jealous.

Lincoln pays the bar tab, we head to the Red Stiletto restaurant, the upscale steak and seafood fine dining establishment inside the hotel. Camerson and I follow behind Lincoln and Baldrick. The hostess addresses Lincoln by name. We were seated at a round table. On my right was Cameron on my left Lincoln; Baldrick was directly across from me. We shared seafood tower, Caprese salads, ribeye steaks and sides and a few bottles of fine wine.

Conversation Over Dinner

During dinner Baldrick and Lincoln mostly talked business. A few times they reminisced about their football playing days. Baldrick played for 10 years on eight different teams. Lincoln and Baldrick were team mates at one of Baldrick stops. Lincoln, a wide receiver went to college at USC, Baldrick went to UT. I mentioned UMD; all they said was ‘oh a basketball school.’ Carmen went to dance school.

Cameron and I were able to chat with each other. She implied that she was formerly an exotic dancer, that worked the exclusive club circuit, with club stops in Dallas, Houston, Phoenix, Las Vegas and Tampa. I wanted to mention Willow, my Exotic dancer friend with benefits who is now in Dallas. I thought better of it.

Baldrick and Cameron now coown Eclectic Elegance Boutique in Tampa. She’s his girlfriend, although she also implied that they were not exclusive. Apparently Baldrick and Cameron are Lincoln’s clients.

A few restaurant guests people recognize Lincoln, not so much Baldrick. Cameron and I are mostly treated as their eye candy, I feel as if I’m a decoration at the table. And I am ok with that tonight. I’m here to have fun and hopefully it will be kinky and naughty later. From time to time, Lincoln will pay attention to me. He will touch my hand or arm.

The conversation only turned to me a few times. That’s good news. I can then be vague about me. Although I always have a few personas when I am Jenn. This week’s persona for Jenn is a marketing consultant. I am always asked in these situations. It explains why I am at the Convention, but truthfully no one will see Jenn at the Convention itself. I never ever bring up the airline business.

Between the salad and the main course Cameron and I went to the ladies room. She asked, I quickly agreed. Hey girls never go to the rest room solo. We were able to have a quiet chat. She mentioned that she needs a break from Tampa, and I assumed Baldrick. Looking at me, she remarked, “Jenn didn’t you say you live I Dallas?” I nodded affirmatively “Do you know anything about the Cabaret Royale? They want me to come dance for a few long weekends. I used to dance there.”

I gulped, “I have a good friend who dances there.” As I said it, I knew I should not have done so.

“What’s her dancer name? I used to dance under Tamara. I said I didn’t know her dancer name. Whew, I dodged that bullet. Cameron, then added, “Let’s hook up when I am there. Here’s my card.” I fumbled through my clutch for a Marketing Consultant business card. My thong dropped out on the counter. Whew I found one, Jennifer Nicole, Marketing Consultant. I handed it to Cameron. She then added, “I will call you when I know I will be Dallas.”

Seeing me stuff my thong back into my clutch, Cameron remarked, “Baldrick likes it when drop my dress and I am pantie less.” She smiled as we made our way back to join the guys.

Nightcap then An Offer… Or Rather A Demand

We finished dinner, we then enjoyed a nightcap at the small lobby lounge. Lincoln and Baldrick made plans to hook up tomorrow. Baldrick said to Cameron, “We have to go Baby.” He stood, holding his hand out to her. Lincoln and I stood. I hugged Cameron, she whispered in my ear, “Talk to you soon Jenn!”

Then Baldrick and I embraced, his arms engulfed my lower back, but he quickly moved his hands down to my booty. He cupped both cheeks with a slight squeeze. He softly whispered in my ear, “Jenn I want to pound your ass, too!” I grinned looking up at him. He’s a massive man. ” If you get tired of Lincoln, I want to make your sissy cock bounce!” I just grinned again, thinking so he already knows. Apparently Lincoln kisses and tells.

We both watched them leave Lincoln motioned for me to sit. He spoke first, “So my little white bitch, have you ever serviced a Black Man?” I bowed my head as I nodded yes.

“Terrific, then you know what to expect! Then do I even need to ask if you will join me in my suite tonight?” I nodded. “Speak Bitch!”

“Yes Lincoln Sir, I am your white sissy bitch tonight!” This is what I wanted from the moment I saw him at the pool.

He added, “Then you consent!” I nodded.

He stands, I stand. We head to the bank of elevators. Lincoln uses his key card for the express elevator to the Penthouse Suites. Lincoln is staying in one of the two suites. Once on the elevator, he attached a silver leash to my outer silver necklace. He gently tugs the leash down. I bow my head. The elevator quickly ascends the 10 floors to the penthouse level.

The doors open, we step out. There is a long hallway stretching in two directions. Lincoln lightly tugs on my leash, then said, “Take off your dress bitch!” Lincoln unzipped the back. My satin dress dropped to the floor. I stepped out of it, as I picked it up, he discovers my chastity covered cock. With his huge hands he squeezes my caged cock. I gasped at his touch. He wasn’t gentle. He smirks, “I see the white sissy bitch knows what to wear to please her Black Royalty! Sissy clits should always be locked.”

He pulls my face towards him. Lincoln kisses me on the lips. “Now on your knees.” As I did, he took my dress.

The Need to be More Than Just Good

He led me to his suite. Trying to keep up I crawled behind him as best I could. Once inside, he tossed his suit jacket and my dress on the nearest chair, then sat in the other. I kneel before HIM. On the table between the two chairs is bottle of port, and two snifters. He pours the port into one snifter. “Sissy bitch are you a good cocksucker?” I nod yes. He then sternly said, “Speak sissy!”

I mumbled, “Yes!” Then much clearer I quickly added, ” Yes Sir!”

“Sissy in private you will always refer to me as Master!”

I replied, “Yes Master!”

He stands, unbuckling his pants, he steps out of his pants tossing them on top of the other clothes on the chair. His cock is massive, more than fills the pouched front of his tight briefs. He sat on the edge of the chair. Tugging on my leash pulling me towards HIM, he demanded, “Pleasure me sissy!” I place my hands on his hips, pulling his briefs down his massive thighs. His semi flaccid cock is indeed huge. I hold his cock in my hands. My hands are small by comparison.

I took a moment just to admire the size and girth of his cock. It’s heavy, girthy, circumcised, and smooth. Lincoln brought me back to the task at hand, “Sissy stop gawking and start sucking!” I ran my fingers down his shaft, opening my mouth I leaned forward, my entire body tingled, it always does. His cock size was little frightening perhaps, but that feeling all went away when his cock touched my tongue.

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