Jenn Knows How To Be Bad
Note: Publishing in this category will be a first time for me. Most of my stories have been published in one category, Transgender and Crossdressers. I am comfortable writing in that category. But I have started to venture out. I hope you enjoy the read. And your feedback is appreciated.
This story is also a continuation of 'What Happens Stays a Secret or Not', that appears in the Jennifer Nicole's Hotel Encounters. It's not imperative that you read it first, but it might give you a better perspective of some of the characters.
Miami Beach - Day Two
When I left Lincoln's suite all I was wearing was his white tee shirt, that was barely long enough to cover my booty but not my silky sheer shiny stockings with lace tops. Underneath the tee my breast forms were now stuffed back into leopard print bralette and my cock was firmly encased in my matching thong. My black silicone chastity cage was in my clutch. My stilettos were in my right hand. My make-up was a mess.
It was a quick descent from the penthouse suites to the lobby. The lobby door popped open. The lobby was not busy, but not empty either. I stepped out. The morning sun shined through the large windows. It was bright and in the right light the bra and thong silhouette was visible through the white tee.
This wasn't my most difficult walk of shame, but it's still a little scary.
Once in the lobby I needed to make my way to the nearby bank of elevators, that serviced my floor. I did my best confident strut. I pressed the up arrow. The light panel indicated that two elevators were descending. One car stopped on three; the second car arrived at the lobby first.
The door opened; three men dressed in suits holding briefcases stepped out. Two were in deep conversation, the third guy blocked the door from closing. As I entered the elevator I could feel his eyes focused on my body especially my rear. My bare booty cheeks were showing. Once inside the car, I turned and curtsied as I pressed my floor button. We exchanged big smiles.
As the door was closing, a female hand pushed it back open. She jumped in; as she glanced my way she hit her floor button, two floors above mine. She was dressed in tight running gear. She sported long legs and a perky booty. She appeared to be my age. Giving me the once over, she placed her hand over her mouth to suppress her giggling.
I know my appearance was very revealing. I was not perturbed but rather amused at her reaction. A we ascended she was still giggling she remarked, "It looks like you had fun last night. The proverbial walk of shame is never easy. I know from personal experience." She paused, "BTW if he has a friend, I am available."
We arrived at my floor; the door opened. I stepped out, smiling I replied, "And yes he knows how to use his huge tool."
The girl smiled back at me, quickly responding, "I'm serious, I'm Heather. I'm in room 710. "
I instantly pushed my hand on the closing elevator door, to keep it from closing. "I'm Jenn, I am seeing him later. And if you are indeed serious I'll ask." She smiled and nodded yes.
I turned right to head towards my room, I looked back to see if Heather was watching. She was. She remarked, "You have a nice booty Jenn!" I lifted the back seam of my tee shirt, revealing my leopard print thong and my bare cheeks.
Before we go any further, let me give you some background.
So How Did Jennifer Nicole Get to South Beach?
I am Jennifer Nicole; Jameson is my given name. As Jameson I am gainfully employed as a male marketing executive in the airline industry. I have risen through the ranks to become one of the top marketing executives. I travel extensively in North America and Europe for business. Originally based in San Francisco for the airline, I currently reside in Dallas. Since my college years at UMD my alter ego, Jennifer Nicole has evolved almost daily.
During all the years I have worked in the airline industry as a male during the day, all other times his alter ego, Jennifer Nicole came out to play. Jameson travels, with his male business clothes packed alongside Jennifer Nicole's feminine attire.
It's Trade Show Season. I'm in Miami Beach for the largest trade expo in the sports business. I arrived a few days before the Convention for a little R&R and private meetings. I always stay at
The Dakota
on Ocean Drive. I've stayed there often. The hotel staff is familiar with Jameson and his alter ego Jennifer Nicole.
On Day One in
'What Happens Stays a Secret or Not'
Jenn met Lincoln Carey at the pool, then had dinner and cocktails and more.
This story contains sexual 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 story of Jennifer Nicole Madison's Kinky Adventures continues by adding another episode, at this point in her life's journey. From now on, the story will be told in first person.
My Morning Took A Twist
I returned to my room. Instead of a shower, I took a warm bath in the soaking tub in my room. It was relaxing and I needed to relax. Lincoln pounded my ass last night. I was able to touch up my smooth skin removing any unwanted body hair. After the soak, I checked my messages. My private meeting has been rescheduled to tomorrow. I caught up with my emails. The rest of the day was now all mine. Lincoln hasn't contacted me yet for our return engagement.
So, pool time it was. I applied my casual make-up, my teardrop adhesive breast forms, then donned my sky-blue one-piece bikini with a high-cut design. It provided decent coverage in the front to help conceal my bulge and forms, but the low cut back that is minimal but daring. It showed off my booty. A matching little skirt will help hide my bulge too.
I made my way back to the rooftop pool. Hurley, the bartender was there again today. I looked around, the pool and deck was nearly empty. I had my choice of loungers. There were two in the corner that were private.
Hurley made his way over to me, he said, "Good day Miss Jenn, may I get you a cocktail?"
"Same as yesterday, Hurley." Hurley hurried off, retuning quickly with my pineapple, orange juice, coconut rum, grenadine, and cherries cocktail. It was yummy. I read the book I started yesterday, sipped my cocktail, then rolled over to get a little bronze on my back. I fell asleep. I have no idea how long I had been dozing.
There was a little rumble next to me. I had company. It was blonde in a very skimpy side tied emerald bikini, adjusting the deck lounge. We made eye contact. It was Heather from the elevator. We both recognizing each other spoke at the same time. I said, "Heather right" She nodded.
"Jenn, right. I'm sorry that I just disturbed you, but I see that you are more relaxed now."
Smiling, I added, "I fell asleep. I didn't get much sleep last night."
Hurley arrived before Heather could reply. She pointed to my drink, remarking, "I have what's she's having."
She settle in face down on the lounger. We both were laying on our stomachs. It was a good thing, as my cock was semi aroused, just looking at Heather's body. Her boobies were overflowing out of her small bikini top. And the bottom barely covered her almost flawless butt cheeks.
As we chatted, we soon learned that we were in Miami Beach for the same trade show. She was the USA Sales manager for a European apparel manufacturer. I said I was also attending, but I was very fuzzy in what capacity. I always need to hide my true identity in public. Heather was based in Chicago. I told her I now lived in Dallas.
She took a quick dip into the pool. Her body is even more stunning wet. She returned to her lounger laying face down again.
Two Girls Just Chatting
We talked about everything but business. You know girl talk. We talked about men. Yes girls talk about men. She said she was formerly married but she's now single. She didn't give me any details on the split. I remarked that I have never been married.
After a while, I saw her gently press her upper thigh with two fingers. She was starting to get a little red. I remarked," Heather it looks like you need some lotion." She nodded affirmatively.
"Jenn, will you apply sunscreen, to my legs and back?" It was my turn to nod affirmatively. Who wouldn't want to caress her hot body.
Heather's head was face down on her bundled beach cover. That was good. When I stood I had to tuck my semi aroused bulge back inside the lower seam of my suit.
I generously applied the tube of Sun Bum, to her back and bare booty cheeks. I also slowly massaged and applied the lotion to her long legs. I could hear Heather softly moaning. She pushed herself off the longer, to turn over. Her nipples were visible. I noticed that Heather had also removed the liner in her bikini bottom, her camel toe was pushing against the thin fabric.
I handed her the lotion tube. She generously applied the lotion to her stomach and boobies. Heather's fingers pushed under the bra cup. Her nipples hardened at her touch. She looked at me again, remarking, "Now it's your turn Jenn!"
Will Heather Discover My Secret?
I lowered my body back onto the lounger. With great difficulty I tried to hide my aroused bulge that was pushing against the thin fabric of my suit. I was so hard that I instinctively knew that the silhouette was visible. I stretched out, giving Heather full access to my back.
She started applying the lotion on my lower legs, raising each leg to have better access to my thighs and calves. Her touch was soft and gentle. She lightly but firmly applied lotion all over my semi bare booty cheeks. I started to whimper softly at her touch. Heather then sat next to me on the edge of the lounger.
Heather gradually pushed my legs wider, giving herself an opening to my inner thighs. Her fingers were now very close to my crotch. I tried to hold back my whimpers. I wasn't very good at it. She pushed her fingers underneath my lower torso, discovering my balls and aroused cock. I gasped. Heather tenderly rubbed my shaft through the suit fabric. She leaned down to whisper in my ear, "What have we been hiding here Jenn? Aren't we a horny femboy?" I did not respond.
