Kinky Travel - Hotel Encounter

This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. If there is any similarity to any person, living or dead or any location, then that is pure coincidence, it was not intended. Your comments and feedback are greatly appreciated. Nikki or Jamie if you prefer, leads a double life. She is gainfully employed as Jamie, a male marketing executive in the airline industry. A very limited few of his colleagues know anything about his alter ego. Nikki, the alter ego emerges, almost daily outside of Jamie's work responsibilities. Nikki has been dressing as a femme since her college years. 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.

Friends have been asking me to tell my story. I have been reluctant after much thought here goes. This is one of my many adventures. It's not the beginning. It's simply a chapter in my life. I hope you enjoy it and please give me honest feedback. So, the life story of Nikki Madison's Kinky Adventures continues at this point in her life's journey.

After a long day of doing my male related business in San Francisco, I return to my hotel on Nob Hill to relax to enjoy evening free of all clients. It's time for Nikki to fully reappear.

Whenever I can I always wear sexy lingerie hidden underneath my male clothes. Sometimes it's just sexy panties or like today a full lingerie set. As I slipped out of my male clothes, I glanced at the floor length mirror and smiled., saying out loud to myself, "I do look good in this red cut out unlined bra, lacy garter, and thong. The red sheer stockings hooked to the garter give me a sexy sensation throughout my body." I removed the lingerie, placing the lacy undies neatly on the chair in the corner of the room.

I quickly take a shower, using a floral scented body wash, touching up with shea body cream to remove any body hair. With years' experience I have my make up routine down. I quickly bob my hair. I finish with red lipstick that enhances my complexion. A nice pearl choker will be added later.

Tonight calls for fresh lingerie. I will do black tonight. I picked out sheer lace boned cincher, with an embroidered underwire bra, that fit snugly over my silicone breast forms, giving a sense of cleavage to my dress. My matching G String fit perfectly over my perky booty encasing my sissy clit.

I sit on the edge of the bed to roll up my stockings. I had packed a new pair of sassy 20 denier sheer stockings that have a red top with a baroque, floral pattern. The stockings are hot, giving my legs a vintage thigh to ankle back seamed look. I always get turned on when I roll a pair of stockings up my shaved and smooth legs. My excitement swelled as I snapped the stockings to the garters, fitting them under the pantie string. I slip on 3" red stiletto heels. I stand, then glance at the mirror.

Smiling, again, as I admired my sensual body, the feeling that something was not right overcame my thoughts. I was feeling very submissive tonight, so I reached inside my suitcase, to see if I remembered to pack my black silicone chastity cage. I did. I slide the G String down my legs, then stuffed my semi aroused sissy clitty into the chastity. It's always a challenge.

I then cover my clit in the black G string panties. I look back to the floor length mirror. I changed my mind, let's do a red sheer G string. Red lipstick, red stilettos. The red lace stockings compliment my look! I then slipped a silk LBD shimmer, knee length over my body, revealing just enough cleavage. I gaze into the floor length mirror again. I twirl for self-approval. I flash myself. I am ready!

The hotel bar on the property sets off the lobby. It's the perfect place to show off Nikki this evening. It's a full Mahogany wood bar with an ideal atmosphere of sophisticated ambiance. I enter the bar and stroll straight to one of high back stools. I feel all eyes on me as slowly walk across the room. Knowing that people are watching my every step gives me goosebumps. I hop up and sensually cross my legs, revealing just a touch of red lace stocking top.

Jason is the bartender again tonight. Jason served me last night too. Our conversation was pleasurable and very flirtatious. I enjoyed spending time at Jason's bar last night. I am sure my secret was apparent when I settled my bill to my hotel room under Jameson Madison. As I prepared to leave, Jason was a true gentleman last night. as he asked for my hand to kiss me. "Good night, Nikki Madison, I hope to see you again." I smiled, "Of course, I promise!" I strutted out, wiggling my perky booty.

So, tonight as I sat down, I simply said to Jason that I always keep my promises. We exchanged broad smiles. Jason acknowledging my presence, said, "Welcome back, Nikki." I ordered a Manhattan straight up. My Classic 'go to' cocktail.

My eyes wander the room checking out the men and the women, seated at the bar and tables. Everyone seemed to be enjoying themselves. There were few that interest me. Two attractive women at one of the round tables caught my attention. My assumption was that they were friends waiting for other friends to join them. Their animate conversation ruled out working girls.

Then one handsome, older gentleman held my attention. He and I are playing coy with each other. Making eye contact, then looking away. He smiled straight back at me; Not being coy any more I smiled back. Of course, he took the bait. He leans in to chat with Jason, then looks back at me. He pointed to himself, then to the empty stool next to me. I smiled back, mouthing sure.

He joined me as Jason placed two new cocktails in front of both of us. Apparently, we both enjoy Manhattans. We exchange pleasantries. Nikki here and handsome Ken now next to me.

Ken appeared to be in his early fifties. Very distinguished. As he scooted in, Ken noticed the red stocking top lace. We started the typical small talk to get to know each other better. We talked about work in vague terms, our music interests, sports. Ken was a 49ers fan, and travel. We both had been to many countries and cities across the globe as well as many USA destinations. As I said, all that small talk stuff.

As we were finishing our cocktails, Ken asked if we could find a table in the room. I said sure, as I wanted to learn more about Ken. Our time together so far has been extremely pleasant.

I closed my tab with a generous tip for Jason to Jameson Madison's room. Ken motioned for Jason, to transfer his bar tab to our waitress. He left a generous cash tip on the bar for Jason. We found a cozy table in a secluded area. It was very private.

As we sat down, two new cocktails were delivered by the waitress Clare. I felt safe as I could still see Jason at the bar.

Ken moved in closer to chat. The conversation became more intimate. I told Ken that I loved to kiss. Ken leaned further in, and I took the opportunity to kiss him full on the lips. Ken cupped my chin and kissed me back moving his tongue into my mouth. I accepted and reciprocated. I could smell his manly aroma.

I took a deep breath as our lips broke away. We leaned into each other again. It's what I wanted from my new companion tonight, and I think Ken did too. Ken instinctively placed his hand gently on my knee running it tenderly across the top of my stockings. I moved my legs by doing to flash the red lace tops. Ken stated obvious, "Your legs are gorgeous. The lace stockings are very sexy! Your sexiness is infectious."

I blushed appreciably. Every girl, me included, wants to be told how stunningly sexy she looks.

As if on cue, Ken softly ran his hand further up my thigh, following the garter strap in search of my pussy. I didn't want him to quit but I had to stop him. I placed my hand on his, I smiled at Ken, and simply said, "I must tell you something."

He placed a finger over his mouth, "I know Nikki; Jason shared your secret. I stay at this hotel all the time and I have become one of Jason's better customers. Please don't be mad at him."

I wasn't. I was grateful.

With all that out of the way, I leaned in to kiss Ken again. I felt his fingers continue slowly up my legs. I opened my legs a little wider to make it easier for him to navigate my inner thighs. He found my sissy clitty, I whimpered but at his first touch, he backed off. I whispered in his ear to squeeze me. He whispered back, "I didn't expect to find your clit encased!"

He pushed my lacy G string panties aside to rub my chastity caged clit. My precum let him easily slide around the cage. He squeezed my gently clit again, running his fingers up and down the silicone shaft. As he continued to explore my caged clit, Ken said, "This will be a first for him."

I moan softly as I stick my tongue deeper into his mouth. Ken squeezed my caged shaft yet again. I pushed back against his hand. My body temperature was clearly getting hotter and hotter.

Clare, the waitress, returned to the table, interrupting us. She giggled to acknowledge her presence. Ken asked for the bill, as it was time to 'get a room so to speak.' I slipped my room key to Ken. He settled the bill. As we walked out hand in hand I waved at Jason, smiled then mouthed the words "thank you."

We reached the elevator as a few others joined us for the ride up. We punched 10. All the others are on the lower floors. One by one they disembark.

Ken placed his hand on my butt finding my bare booty bottom through my black silk dress. He discovers the garter strap again and playfully clicks it. Once the last passengers exit on their floors, I turn to face Ken. He is now cupping my booty with both hands. We embrace. We ascend to 10 in full embrace. He pushes me back against the elevator wall pushing his manhood against my body. He kisses my neck. I am taking deep breaths. We found my room.

Ken unlocks the door, lifts me into his arms, as if I was his new bride to carry me through the door to the bed. We fall onto the bed still kissing. We can't get enough from each other.

I am still prone on the bed as Ken slides off me. We never broke our lip lock. My shimmer was now bunched up around my waist exposing my stockings, garters, and caged bulge. Ken's very manly hand found my caged sissy clit once again. I could feel the pressure as he continues to squeeze my clit through the cage. I was throbbing as my soft moans became louder. Ken slid down to get a closer look at my black silicone cage in my red G String. He again moved the sheer fabric encasing my clit to the side. I was dripping.

Ken cupped his hand to catch my precum. I was on my elbows, leaning forward watching his total fascination. He brought his cupped hand to my mouth, and I licked my sweetness out of his hand. I did not swallow as Ken leaned in again to kiss me and we exchanged tongues along with my sweet juices. Ken's hand returned to my cage. My moaning got louder. As best I could I told him I wanted him in me.

Ken rolled me over so I could get out of my shimmer. He unhooked my back zipper then eased me out of my dress. I tossed it to the floor.

I crawled across the bed to unbuckle his belt. His pants dropped to the floor, and I slid his sexy briefs down his legs. I was face to face with his hard cut cock. His helmet was inviting. My mouth was instantly sucking its large head. Ken removed his shirt; He is very toned for a man his age. Ken lifted me, as he gently pushed me back onto the bed, he then pulled my legs over the end, pushing a large pillow under my lower back. He exposed my boi pussy; my red G string was removed.

I tried to tell him I had lube in my purse, but he had other ideas. Since I was still dripping profusely my pre-cum became the lube as Ken fingered my ass. Ken was big but not the biggest I have had in my boi pussy.

The tip of his cock pushed into my puckered hole; my legs straddled his shoulders as he pushed further into me. I squealed as he pushed harder, my tightness grabbed hold of his cock as he pushed further. My squeals turned into moans of pleasure. My caged sissy clit was flapping as Ken expertly pounded my ass. Ken knew what he was doing. i concluded that my boi pussy was not his first.

My moans became louder. My body began tensing. Ken's cock has found my p-spot.

He pulled my legs closer together as my ass tightened around his cock. My body began shaking uncontrollably. I could feel the tightness of his cock. His cock exploded; my body took over my mind as I screamed. My body was uncontrollable: my sissy orgasm was complete. I shuddered deeply. Then my body began to calm down.

Ken didn't immediately pull out but when he did, I could feel the huge load he left in me. Ken rolled me off his shoulders and laid down next to me. His hand again cupped my caged clit. This time he slurped me into his mouth and kissed me again. We embraced. I fell into his arms and whispered thank you. He simply said, "No thank you Nikki!"

Fully content, I fell asleep in his arms resting my head on his broad shoulder. I was soon startled as I felt Ken move my head from his body. He was on his knees fondling my clitty in its cage.

He was toying with the silicone shaft tube. It was still locked. The ring snuggly fit around my balls. He was inspecting the entire contraption. As he played with my shaft it again tightened in the cage. Ken asked me twenty questions... what's it feel like, can I cum, do I wear one permanently and finally do I have the key. I told him I felt very submissive wearing one under my clothes as well as being used as a sex toy.

I told him I was not permanent and owned six different styles. I self-locked, although I have had more than one key holder in the past. The key was in my purse. He found my purse and flipped it to me. He said, "Show me." I hesitated as I removed the key from my purse. I smiled and he smiled back, saying "Let's unlock you." I did, my clit immediately grew to its full hardness.

Ken began stroking my sissy clit shaft. In about ten strokes I dropped a generous load into his hand. I ran my tongue over my lips, begging for him to feed my mouth once again with my juices. He put his cupped hand level with my mouth. I eagerly slurped my own juices. He ran his hand down my neck forcing me to swallow. As I did I smiled back at him.

I reached for his cock, he stopped me, simply saying, "Not now Nikki, later."

I thought he was going to leave but motioned for me to undress and keep my make up on as he crawled into bed to watch me undress. I did so. I love to undress with an audience.

In my suitcase, I had packed a sheer night gown that covered my upper torso, the bodice held my breast forms in place.

I snuggled in next to Ken. We pillowed talked for a few minutes, exchanging a bit more about our lives. Neither of us wanted this night to end but realized that we had lives to get back to in other cities. We both knew we wanted an encore but were exhausted. We fell asleep with me cuddled with his cock next to the crack in my nylon covered booty. I slept in the wet spot.

I woke up, startled as I heard the door close. Ken was nowhere. I saw a note on his pillow. "Nikki you are awesome. I enjoyed being with you. You are very feminine, and I enjoyed your clit cage. Thank you for that experience. I am sorry I had to leave this morning. I have an early flight back to Seattle. I relished our entire time together. I do want to see you again. Dinner, dancing, and an encore. Call or text me at this number. Let's see how our paths can cross again. Ken"

I was sad that Ken had to leave, my bed felt empty, but I was very satisfied. I took a few deep breaths as I drifted back to sleep.

To be continued