Kinky Travel - Hotel Staff

Next Day and Hotel staff

Hotel Staff the second installment of Nikki's business trip to San Francisco. 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. Jamie has been dressing as a femme since her college years. A very limited few of his colleagues know anything about his alter ego, Nikki.

Nikki, the alter ego emerges, almost daily outside of Jamie's work responsibilities. Last night Nikki met Ken at the fancy hotel bar. You will learn more about the hotel staff in this chapter.

This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. Your comments and feedback are greatly appreciated. So then the life story of Nikki Madison's Kinky Adventures continues by adding another episode, at this point in her life's journey. 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.

I was a little sad that Ken had left but my mind went back to the great time we had last night. It was enjoyable getting to know him and of course the sex was terrific. Not every man knows how to give a trans woman a sissy orgasm. Ken does.

My morning wakeup call silenced my thoughts. As I picked up the phone, the female voice on the other end, "Good morning, Mr. Madison. Enjoy your day!" Before she could hang up I requested a pot of coffee and fresh fruit from room service. "Right away!"

I needed a shower, but I was not sure how much time I had, before the coffee arrived, I decided to stay femme. I picked up my dress and assorted lingerie off the floor. I was still dressed in my black sheer gown, so I slipped into the red G string to conceal my sissy clit. As I did, there was a knock at the door, "Good morning this is Manny, from Room Service."

My gown flowed across my body, so I tightened the fabric closer. to my body. Opening the door, Manny entered with his cart. He looked around the room, then placed the fruit and coffee on the table. He poured me a fresh cup of coffee. I signed the receipt, reaching into my clutch for a tip, my gown revealed my red G string. I could see a smile on Manny's face. I looked down, my sissy clit was bulging outside its tiny covering. As he backed out the door with his cart, I handed Manny a generous tip.

I had one more day and night in the city. Work time was over, so I had all day to spend in the City, sitting down at the table I took a few moments to relax and enjoy my coffee. Crossing my legs, I could feel Ken's juices dripping down my thigh. I searched my suitcase for my anal plug, popping it in my puckered hole to keep him inside me for a while longer.

My cell phone pinged. I picked it, it was a text, I scrolled my messages, both text and emails. Nothing of immediate importance, I started to remove my make up. I needed a shower, using my shea cream I did touch up to remove any unwanted body hair. I took extra time on my face this morning. Since it was a casual day, I would keep my make up light. Although I couldn't resist pink lipstick. I was very fortunate to have smooth skin with female facial features. Good genes from my mother and three sisters. I finished my make up.

I put on a pair of seamless skin-colored shape forming spandex panties. No pantie lines. My black yoga pants fit nicely and highlighted my perfectly rounded booty. Thet crisscross back scrunch butt style gives me a lot of compliments. It accents my booty. I was very causal for a relaxed day in the City. I chose a magic mesh red sports bra that enabled me to wear my breast forms without anyone noticing.

A pair of walking shoes, shoulder purse and I am off. I took the elevator down and briskly walked across the lobby. I could feel the eyes on my booty. I love it. I could feel my jeweled anal plug as I walked towards the door.

Outside I worked my way down California Street to my favorite coffee shop on Washington Street. Yes, I needed more caffeine. I didn't want to act like a tourist, but San Francisco is one of my favorite cities to explore. I sat outside the coffee shop to enjoy my latte with their special croissants.

I wanted to take control of my day, relax, catch up on my texts and voice mails. I sent Ken a text thanking him for cocktails and wonderful evening of sex. I told him that I too wanted an encore. We exchanged texts as we set up a time to talk next week. I took the cable car to Fisherman's Wharf, enjoyed an Irish coffee at its American home, strolled over to the bocce bar courts to watch some the local older gentlemen enjoy their early afternoon. It was a gorgeous San Francisco day, so I walked along the Embarcadero. As late afternoon approached, I was able to catch the California Street cable car back up to my hotel. Tonight, I wanted to go to dinner at one of my favorite restaurants in Cow Hollow.

I slipped into the hotel bar to see if Jason was working. I wanted to thank him for introducing me to Ken last night. Terrific, he was there setting up his bar for the evening. I noticed his big smile as I walked in. I beamed back at him. We chatted; he acknowledged identifying my secret when I signed my bill the first. I told him I was so delighted I had shared my secret with Ken.

He asked me about my plans for the evening. I told him about my dinner plans, telling him that I use to hang out there when I lived briefly in San Francisco. He said he was very familiar with the restaurant. In passing he reminded me that the hotel bar closes at midnight. Since Clare, the waitress from last night was assisting him at bar tonight, he casually mentioned that he might be getting off earlier than expected tonight.

That was surprising. I finished my drink, paid my bill, and with a generous tip, I smiled then said I would see him later. Jason gave me a big smile back. I could feel his eyes on my booty as I left the bar. I gave it a little shake as I went out the door.

Back in my room, I took care of a few text messages. It seems that my day job never ends. Although there was a text from Jonathan one of my friends with Nikki benefits would in Las Vegas later next week. He invited me to join him. I texted back affirmative.

I laid out my outfit for the evening. Another black ensemble. A silk back bra and bikini pantie set. Both had lacy inserts. My breast forms fit perfectly in the balconette bra. No garters tonight as I opted for a pair of matching patterned top thigh highs. I slipped another silk skimmer. As I stepped you could see a flash of the thigh high tops. I love the feel of silk, so it was all silk tonight, . It makes feel very sexy.

No chastity tonight either. I still had my jeweled anal plug tucked inside my booty. I slipped my 3" red heels that matched my lipstick.

I did my twirl for self-approval. I am ready! I went to my Uber app to order a driver to Greenwich and Divisadero. I rode down the elevator and across the lobby to the front door. My ride was waiting. I jumped in and flashed the doorman with a nice view of my lace topped thigh highs.

It was a short ride to my destination. A restaurant with no name on the outside.

The after-work activity at the bar was heating up. I found a seat at the bar. I recognized the bartender, Colin. A transplanted Brit. I greeted him, by name. He looked at me quizzically, trying to remember me. I don't believe he did. I gave him my hand... Nikki here. I ordered an Italian Spritz. Then another.

Colin kept coming back to chat, then finally said, I recognize you but... I smiled and simply said because you have never seen me this way. You know my male alter ego. I explained.

We chatted back and forth. I had dinner at the bar, along with a glass of a nice red Napa blend. When he wasn't busy with other customers Colin, and I chatted some more. He was a perfect gentleman. He was fascinated at my feminization. He kept repeating how stunning I was as a female.

A gentleman that looked familiar sat next to me, I said, "Hello Michael." He looked quizzically back at me, trying to figure out who I was. When he couldn't and gave up, I leaned and whispered my male name in his ear. His jaw dropped.

His hand reached out to shake my hand. I redirected it to my stockinged leg. His eyes lit up. I smiled back. I couldn't resist. I am a pure tease.

He rubbed my leg. I know he wanted to slide it up to my thighs, but he never took his hand off my knee area. I whispered to Michael that I had plans for the night but would be back in about 3 weeks. He smiled back, indicating that I could find him here on most nights. I knew that already.

My inner self was telling me that it was time to go back to the hotel. I wanted to spend some time with Jason. I tried to settle with Colin, it said it was on him. I smiled and thanked him profusely. I asked if he could call me a cab. He did. I placed a generous cash tip on the bar.

As I left, I leaned up on the bar rail to kiss Colin on the cheek. My skimmer dress exposed the tops of thigh tops, perhaps even showing a glimpse of my booty. I could feel Michaels eyes on my back, as I stepped back, I bent into Michael, pecked him the cheek and moved close enough so he could feel my sissy clitty hardness on his arm. I scooted out the door and into my waiting cab.

Why the hurry. I wanted, I needed to get back to the hotel before Jason left for the evening. A short rider later, I was back at the hotel.

The doorman caught his second flash show from me. I flashed a smile, then dashed into the hotel making my way to the bar. It was nearly eleven. I looked around, the bar was nearly empty. Jason saw me coming and gave me a big smile once again.

As I got comfortable on a bar stool, he complimented me on my silky skimmer outfit. I giggled as I gave him a clear look all the way up to my silk panties. Feeling a little tipsy and flirtatious I sat there a little slutty exposing my thigh high tops. He poured me a high-end orange flavored cognac in a brandy snifter. He said he was surprised but glad I was here! I just said I am here for him.

The bar would be closing soon, so he began cleaning up. I asked him how long he would be. He said he would be right back. After talking with Clare, the other bartender, he came back smiling. Clare, our waitress from last night, was a cute short haired blonde with a nice booty said she would close out, only if she could join us after she closes. I started to ask but he said yes, she knows. I gave him one of my room keys for Clare.

He said give me the other one too since I need to meet you in your room. I kissed him on the cheek as I left, smiling back at him and Clare. I went to the front desk in the lobby.

The front reception desk person, Jessica, accommodated me with another access key at first, she was reluctant but since my ID matched the name on the room, she smiled broadly as she handed me another key. I said thank you. I gave her my sexiest walk as I paraded to the elevator. As I neared the bank of elevators, I pushed the button to summon a car, then turned. I threw her a kiss. She smiled back. She was indeed an attractive brunette.

Once on my floor, I rushed to my room. I checked my make up in the mirror. Did another twirl. I was still satisfied with my look.

I decided to take my panties off, then thought I should cage her. I slipped on my black silicone chastity.

A few minutes later I heard a knock at the door. Jason unlocked the door and popped in. As he entered, I stood in front of him and let my dress drop to the floor!

Wow is all I heard from Jason. He quickly moved over to me, we embraced to begin madly kissing each other. He pushed his body into me. For the first time, I felt his hardness up against my body. I dropped to the floor. Doing so, I began unbuckling his belt and pants zipper. Jason wiggled out of his pants.

He was without underwear, so my eyes stared right at his shaved cut cock. It was hard and magnificent. I started licking his helmet, flicking my tongue back and forth, slowly inching my way up his shaft. Jason pushed on the back of my head, pushing his cock deeper in my mouth. I gagged a little, but Jason kept fucking my face. Jason pulled out. I want that beautiful ass of yours. He pulled me up to eye level, then gently turned me around pushing me forward over the sofa back. I loved it hard and fast. It brought out the slut in me.

He fingered my boi pussy pushing one then two fingers inside me. I moaned as each finger entered me. His other had reached to rub my sissy clitty through my cage. My pre-cum dripped into his cupped hand, that he used to lube my hole. Jason removed his fingers then began pushing his gorgeous cock slowly inside me. He quickened his pace. With each deep push I moaned louder. I screamed, "I need you now." Boy did he. I am not the first boi pussy that Jason has satisfied this way.

I could feel his thrust pounding my puckered hole I moaned louder and louder with each thrust. He found my p-spot. My body shook wildly. He final thrust filled my I could feel Jason's load filled my boi pussy. He fell on top of me with his hard cock still in my boi pussy. I was spent.

Just then the door to my suite opened again, Clare entered saying, "I see you started without me. Jason's cock popped out as we turned to react to Clare. She had changed out of bartender's tuxedo. She was lovely in her short red pleated skirt enhanced by a black low-cut blouse. She dropped to her knees in front of both of us inspecting Jason's cock with her fingers. Jason was semi hard, and Clare held his balls in her... and just said, "I bet there is more juice in these."

She then squeezed my encased sissy clit in my cage. She swiped one finger over the gap. My pre-cum dripped onto her fingers. She licked her fingers and smiled, "Tasty for a sissy bitch."

She squeezed my sissy clitty cage again, discovering Jason's juice dripping down my leg. She rubbed her fingers up my smooth leg, rising up sticking her wet fingers into my mouth ... I sucked her fingers clean. She stepped back to look me over. "Lovely choice of lingerie sissy. Is that caged sissy clitty still functional. Feeling very submissive, I stammered yes.

She pushed my mouth in her cleavage. I began licking the tops of her beautiful mounds. I backed up as Jason moved in behind Clare, he grabbed the hem of her low-cut top as Clare put her hands in the air. Jason slid the top off as I continued to lick her full round boobies overflowing in her red lace bra. Her pink nipples were hard to the touch of my tongue. Jason then reaches down to remove Clare's skirt. I felt it hit the floor at my feet. Clare then pulled my body completely into her. For the first time her hard pantied cock was pushed against my bare stomach. I had no idea.

Clare pushed me down for me to get a closer inspection of her clit. Her body is slim and tight. Her red silk thong smelled sweet. I slipped my fingers inside the fabric, enabling her wonderful cut sissy clit fall into my hands. I stroked her shaft gently. I cupped her balls. Her clit was gorgeous. She was smaller than Jason but with a very sculptured helmet. Running up and down both sides of shaft, my tongue licked her shaft. I moved my tongue back and forth, up and down. I grabbed her booty cheeks, as I opened my mouth pressing her shaved clitty deeper into mouth. The sensation of her growing clit engulfed my mouth. It was intense. Clare held my head down, content with me doing all the work. I reached down to my caged clit. I pressed with my fingers on my pre-cum for my juices, then pushed one then two fingers, in Clare's puckered hole.

Jason began kissing Clare. The suite door opened again. In rushed Jessica, the front desk clerk, saying, "Sorry I am late!" Clare broke her lip locking with Jason, then spoke up, "I invited Jessica to join us. I didn't think anyone would mind." I never looked up. I was preoccupied with satisfying Clare.

To be continued