Kinky Adventures - Caught

This is another chapter in the Kinky Adventures of Nikki Madison. This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. I have several chapters in various stages of drafts, editing, and completion. If you are reading this chapter, then it was approved. Your comments and feedback are greatly appreciated. If you are an Editor at heart with the time and patience to assist this new writer please contact me.

I work in sales for a major airline. I travel around North America and sometimes Internationally into Europe. I oversee national accounts. I work at industry events, on site customers visits, arrange events for customers and set up events on site at customers facilities, hotels, and convention centers. When I travel, I pack my business clothes and of course my feminine attire.

If I am not with customers, I am in full Nikki mode. I always wear at least panties under my male clothes. Sometimes chastity too and of course a plug from time to time. If I am really feeling randy, I will slip on garters and stockings. I will hide the stockings from the outside world in cowboy boots. On this business trip I am in Seattle making on-site customer visits. I normally stay at downtown hotels so can easily go out as my alter ego Nikki. I stand about 5'7" and weigh about 160 pounds. I wear my hair pixie style, so I can pass as male or female.

Today I was feeling particularly randy, so underneath my male clothes my female attire was lace top pink stockings, lacy pink garter belt, and pink satin camisole with a touch of lace. I stuffed my semi aroused clitty in a pink g string adjusting the panties over the garters. I did a quick twirl in the mirror as I buttoned my blue dress shirt, to hide the pink cami, my male trousers and slipped into my cowboy boots. I fixed my tie, grabbed my blazer, and briefcase and headed for the elevator.

While waiting for the elevator I noticed that I needed a manicure as my clear polish was coming off my pinkie finger. I giggled as I thought it's a good thing that no one today would notice my deep pink toenails.

A few customer calls in the morning were uneventful. I stopped for a brief lunch alone as I headed back downtown to see my best Seattle customer in his office. It was not far from my hotel so hopefully the meeting with Brian, my key contact, would be a short one today. Things were going very well with his company. Lots of business and very few issues. Brian is a tall black man, very much Nikki's type. He is over six foot, with broad shoulders. A little older, just like Nikki likes them. Brian is new in his role, and he's been a good supporter. This is my third visit with him in this role.

The meeting was a little longer than I expected. Brian brought in two female staffers, Jessica, and Stephanie. Both are eye candy. Near the end of the meeting in the conference room, Jessica got up to leave. It's all I could do but stare at that beautiful booty of hers in her tight leather skirt. Trying to stand, and reach out to shake her hand I knocked a bottle of water all over my papers and the bottle landed on the floor. I felt like klutz. I didn't know what to reach for first. As Stephanie grabbed some towels to clean up the water on the table, I bent down to pick up the bottle from the floor, I could feel my shirt ride up the back. I am not sure what I exposed... garter or camisole. I do know that Brian was behind me. I quickly stood up and sat back in my chair. I was not positive about what he may have seen.

The girls left as Brian, and I finished up. We did a little small talk as he led me out of the conference room to the front door. My head was spinning as this company was one of my best customers. I had been so clumsy and exposed. As we reached the front door, Brian looked at his watch and said, "Jamie, would you care for a cocktail at your hotel?" I nervously said sure. Brian said he needed to finish up and would meet in forty-five minutes to hour at the bar. I nodded okay and headed to my car.

I took a deep breath. That was close. I drove to the hotel trying to figure out what to say to Brian if he did indeed see my feminine attire. I valet my car and go straight to my room. I take off my male clothes but stay femme. I pace back and forth. I slipped on a pair of pink heels. I continued to pace. If I came out to Brian, what would he do. I came to a simple conclusion. Be Bold! Let's go for it.

I took a double check of any body hair that needed to be touched up. I sat down to put on my female face. I wear a diamond stud in my left ear. My right ear lobe is also pierced but I don't wear an earring when in male mode. I inserted the matching diamond stud. My g string was now damp, so I changed panties. Since I brought my silicone self-adhering breast forms, I could go braless. I rummaged through the dresses I had packed.

I went with my black midi shimmer that laced up in the back. I also found my pink studded butt plug. I lubed my boi pussy and shoved it in. I found a floor length mirror behind the bathroom door. Did my twirl to make sure I met my own approval. Transferred all my personal items, including my lube into my pink sequined clutch, then walked out the door heading for the elevator.

On the way down, my stomach was turning, and my head was spinning, debating if I was making the right decision. If I am wrong Brian could make my business life miserable. I reached the lobby, took a deep breath, and strutted to the bar on the first floor. As I entered the bar area, I looked around for Brian. He was seated at a small pub table for two.

He saw me coming towards him, he smiled broadly. I asked if this seat was taken. He stood to help me sit. I crossed my legs to reveal the lace stocking top through the slit in the midi dress. I slowly covered up and Brian sat back down.

I giggled and asked Brian if he liked what he saw. Brian placed his hand on my stockinged knee, "Absolutely, I liked what I saw in the conference room you are gorgeous ..."

He began to say my male name but interrupted." I am Nikki, nice to meet you!" My heart skipped a few beats as Brian caressed my knee. We were both staring into each other's eyes. I knew at that moment I had made the right decision to come as Nikki. The waitress appeared out of the shadows. Brian was drinking a Manhattan, I pointed to his glass. "I will have one too." Brian ordered a second.

We were in a secluded area. We could have a quiet conversation but moved our chairs closer together. Brian did not remove his hand from my leg. We chatted more about the incident at his office, my transformation this evening to Nikki. Brian told me he was enamored with girls like me, even admitting that he had a few previous encounters. That eased my concerns about my decision. The conversation with Brian was very comfortable. I learned more about his personal life. He learned more about me. The conversation all centered around my persona Nikki.

We finished our cocktails and two more arrived. I waited for an opportunity to lean in to kiss Brian, instead he leaned in first to kiss my pink rose colored lips. We exchanged tongues. I could not get enough of this man. His hand began to explore my stockinged leg, finding the garter clasp and he playfully snapped it. I smiled back, placing my hand on his crotch. As I expected he was hard and as I had hoped, he was huge.

I slowly unzipped his trousers and his cock head slipped out. He wore no underwear. I fingered his pre-cum, immediately sucking the juices off my finger. His huge hand found my pantied clitty. I moaned and took a deep breath. I whispered in Brian's ear, "Come with me to my hotel room!". He squeezed a little harder and motioned for the check.

The waitress arrived with the check. She noticed Brian's huge cock head sticking out of his pants. She smiled, looked directly at me, "Enjoy girlfriend!" I winked back at her simply said I will! Brian a little embarrassed tucked his cock back into his pants. He paid the bill in cash with a generous tip. We walked hand in hand to the elevator. We punched 10 and rode up alone fully embraced and kissing each other like school kids. His hands held my head as he leaned down to kiss me. We found my room, unlocked the door, and fell inside Brians hands were all over my booty.

As I stumbled back into the room, Brian held me to keep me from falling. I stepped back so he could get the full image of me. I turned around so he could unlace my shimmer. It dropped to the floor as I stepped out of the silk dress. I placed my arm across my breast forms to find my pink lacy bra. I slid it over my breasts and asked Brian to clasp it. He didn't. I turned around to face Brian. He stepped to take me all in then said, "You are one sexy bitch Nikki! Keep the bra on for now."

Brian had removed his shirt, showing me his chiseled torso for the first time. I moved closer to Brian to unclasp his belt, so his pants could drop to the floor. I gasped, Brian's cock was bigger than I thought, It was all mine tonight. I dropped to my knees; my fingers inched up his huge thick shaft. My tongue discovered his huge helmet. I could feel my clitty get hard.

I continued my tongue movements up and down his shaft. I eased my lips around its head, slowly making my way down the shaft. Brian was filling my mouth. I wanted all of him in my mouth. I went back to the tip of the head and again slowly eased down. I repeated this again and again, taking more cock into my mouth each time. I cupped his huge balls. I could hear Brian moaning.

Brian reached down to the bottom of his shaft trying to control his own orgasm. I pushed my mouth down further, feeling his fingers in the way. I replaced my fingers where his were to keep him from cumming. I released my hold on his shaft. I moved my mouth up and down his shaft a few more times. His huge shaft filled my mouth.

I squeezed Brian's shaft one more time with my fingers, released them again. I immediately felt the surge of his cum in mouth, I gagged as I eased up on the shaft. I swallowed as much as I could. I grabbed his thighs to brace myself to the force of his load streaming into my mouth. Brian's hands were on my shoulders, trying to lift me up.

Then a second rush filled my mouth once again. I swallowed what I could, my tongue was now coated with his load and dripping out of my mouth. I released his cock and Brian lifted me to kiss me. My tongue tried to get every drop. We kissed as I swallowed the rest of his juices. I collapsed into his huge chest and arms.

Brian lifted me off the floor and gently placed me on the bed. He crawled in next to me. His huge hand moved my g string to the side as he rubbed my clittty in his huge hand. I gently whimpered to his touch. He removed my plug as he slid two fingers on my taint to massage my p-spot, then he slips the two fingers into my boi pussy. I looked up to him, gasping trying to control my breathing, to say, "You have done this before, haven't you?"

He smiled back to say, "Yes I have sexy Nikki!" He found my p-spot gland, I screamed a little louder at his pressure. My body shakes as he massages me. I scream, "Milk me Brian! Make me yours!"

My entire body shudders with a stream of spasms from head to toes, I buck a little and can feel my own clitty gushing all over my stomach, even my g string. Brian pushes my hand down to my stomach to catch as much fluid as possible. He brings my hand to his mouth as he slurps my fluid then immediately leans in to kiss me sharing my own juices with me. We collapse into a pile on my bed.

I felt very comfortable in Brian's arms. He was strong and he loved to cuddle, too. I turned my body to spoon, placing my firm booty into his stomach pushing on his semi-aroused cock. He got harder. I smiled. He stroked my back and shoulders with long strokes. He even tweaked my breast forms, commenting on how real they felt.

He ran his fingers down my legs. I was still wearing the stockings. I moaned to the touch of his slow caresses. He is gentle. He is caring. He knows how to make love to a girl like me. The sex has been terrific.

Brian reached down to clitty. As he touched her, my clitty, she became hard once again. Brian was stroking me again. I let out a few more moans as his firm hand encompassed my clit. He then used the fluid from my pre-cum to begin to coat the entrance in my boi pussy. He whispered into my ear, "Nikki where is your lube?"

I caught my breath, "In my clutch". Brian found it on the floor next to my shimmer dress. He opened the clutch. He found the lube but also discovered my pink chastity. Brian, pulled it out and said, "What have we here? Let's put it on you Nikki!"

I nodded, as if I had a choice. He quickly stroked my clitty. I whimpered and moaned loudly as I came quickly in Brian's hand once again. Brrian used my natural lube to smear my entire clitty. He then slid the penis ring behind my balls, resting it firmly against my body, pulling each ball through the ring. He continued to crush my hard on so he could fit the cage over my limp clitty. He pulled my boi clitty downward, so the cage fit snugly. He lined up the holes as he slipped on the lock. As I smiled back at Brian, I said thank you. I love being fucked in chastity!

Brian stood up and gently tugged my legs down to the foot of the bed. He placed one of the pillows under my lower back, lifting each leg around his waist, crossing them behind his back.

He liberally lubed his fingers, inserting the lubed fingers into my puckered hole. I wiggled my ass as Brian's manhood started pushing its way inside me. He went deeper and deeper, I was bouncing on his huge shaft. I whimpered and lightly moaned as he slowly pushed even deeper into my boi pussy. I tried to muffle my screams, to no avail. Brian's thrusts continued as if he was pile driving me.

He continues to slam my boi pussy, my caged clitty was moving up and down with each thrust. My full body began to shake and shudder once again. I screamed with pleasure. I was breathing deeper and shaking more violently with each thrust. Internal orgasms rock my world. I lost count of my orgasms tonight. Brian pulled out leaving spread out on the bed. Brian sat down on the bed next to me. He was gently squeezing my caged clitty, then softly said, I want to spend the night, but sadly Nikki darling I can't. Do you have any calls in the morning?"

I nodded no, softly saying, "I am scheduled to leave in the early afternoon." Brian smiled, "Good, order us room service breakfast. I will be here at 7. He looked at his phone. I must run."

He slid his clothes back on. He put my room key card and the chastity key in his pocket, grabbed his jacket, kissed me, then headed for the door. I followed him, we embraced and kissed again. I watched him make his way to the elevator. I closed the door, then leaned against it. I could feel his juices running down the inside of my leg. I smiled, mumbling to myself, "This trip to Seattle has been exciting!"

To Be Continued