Kinky Adventures - Encore with Brian

Brian's Encore

This is the second installment of Jamie's business trip to Seattle. Jamie was caught dressing enfemme underneath his male clothes by one of his best customers. 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. When Jamie, err Nikki travel', she packs her male business clothes alongside of her feminine attire. 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 emerges, almost daily outside of Jamie's work responsibilities. Brian in Chapter One met Nikki for cocktails, terrific sex then departed Nikki's hotel room, vowing to return in the morning. Does he return alone?

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 tossed and turned all night. I could not get comfortable. In the morning I started stirring, slowly awakening in my hotel surroundings. As I rolled over, I felt weightiness on my sissy clit. As I do every morning, I began to rub my clit, feeling that my clit was still confined to cage. I love wearing my cage. Since I self-lock most of the time, I don't normally sleep all night in one of my cages.

Smiling to myself, the warm thoughts of last night's sexual activities all resurfaced. Brian had left me completely sexually fulfilled but, and its big but my sissy clit was still in chastity. I reached into my clutch looking for the key. Then it dawns on me Brian has the key. What's a girl to do.

Hearing a ping, I reached for my cell phone. It was a text from Brian. "Nikki dear, last night was wonderful. I will be back as promised at 7 am. Instead of just two, order room service for three!" I gulped then took a deep breath, my mind is racing, trying to figure out who could he be bringing with him? I glanced at my phone again, thinking I better shower, company is coming. I called room service, hurriedly jumped in the shower. I did a self-check for any body hair that needed touch up.

After, drying off, I sat down to put on my female face, adjusting my silicone self-adhering breast forms. I could go braless. Realizing room service would be here any moment, I needed to finish dressing or at least coverup. I had packed a black silk mid-thigh gown with straps. I wiggled into the gown. As if on cue, there was a knock at my door, a female voice said, "Room Service!" Walking by the mirror, I made sure I was presentable. I opened the door.

Naomi, as her name tag showed, pushed her cart into the room. She started transferring the coffee, fruit, juice, cups, cutlery, and napkins to the table. Since I had my laptop and other work items occupying most of the table, I needed to move some items. I clumsily dropped my laptop to the floor. I squatted to retrieve it. My gown slid up my thighs, exposing my clitty encased in my pink silicone chastity cage to Naomi. I hear her chuckle. I then realized I was caught yet again.

I hurriedly found my clutch, searching for a cash tip. Handing her the money, Naomi smiled, whispering, "Pink and black go well together!" She then turned to push her cart towards the door giving me a little wiggle with her booty. Shaking my head, I lifted the coffee pot to fille one of the coffee cups. Trying to calm myself, I took another deep breath. It was almost 7. I slid my red stilettos back on.

My thoughts went back to pondering who Brian was bringing with him. Looking up, I heard a soft knock on my door, as it opened, in stepped handsome, hunky Brian, following right behind him was Stephanie, one of the Assistants that were with us in the conference yesterday. Stephanie is a very attractive brunette. She was in a tight black leather skirt, that fit snugly to her body. Tucked in her blue blazer was a white crop top, showing a little bare mid drift. She wore 3" red slingbacks. She was still stunning.

I stood up, a little bewildered. Stephanie walked straight to me, kissing me on the cheek, whispering in my ear," I am so happy to be here, Nikki!" Brian, dressed in his business suit, followed her to my side, leaning in to kiss me, but on the lips. Brian took charge, "Let's all sit!" As we all sat down, I took yet another deep breath.

Stephanie spoke first." Jamie, or should I call you Nikki?" I smiled as I nodded yes. "I too saw your secret attire in the conference room. I was excited at the discovery. Brian and I talked before he met you last night. Once he got home, we exchanged texts. He said he was coming back this morning. I invited myself. I hope you don't mind?" She glanced back and forth, first looking at me, then Brian. She was seeking our approval.

Realizing my bold move last night was a risk, I gulped again, clearing my throat, "Stephanie, you are quite stunning. I'm happy you are here. Remember, my life as Nikki is very private." Stephanie held one finger to her mouth, saying," Your secret is safe with me!" She immediately stood, dropping her leathered skirt slowly to the floor, then wiggled out of red satin thong, revealing her bare pussy lips.

I simply said, "Yum!" I stood clasping her hand leading her to the bed. Brian stood with us. Stephanie removed her blazer, Brain stepped in behind her as Stepanie raised her arms. Brian helped her out of her top. Stephanie revealed her red lacy bra, that pushed up, her ample boobies. Helping her to my bed, Stephanie laid down, opening her thighs, pulling me towards her vagina. Her fingers were already massaging her clit.

I buried my face between her thighs, eagerly licking each thigh. I start slowly moving my tongue from side to side, then tightening my tongue, I move up and down. Sensing Stephanie's reaction through her soft moans turning into more intense lower body movements, she clearly loves a firm tongue moving up and down her legs. Gently I continue to move my face up to vagina. I placed two fingers inside widening her vagina, pushing my tongue deeper. Her body begins to shake. I place my right hand on top of hers, helping her massage the hood of her clit. She placed her hands on my head, as she let's me take control.

Pushing my tongue deeper between Stephanie's moist labia lips, I could feel her body moan louder to the touch of my rotating firm tongue. I keep pushing my tongue from side to side, alternating with up and down strokes. Stephanie's whimpers become quicker in response. My face becomes wetter. Her juices are sweet, with deep breaths my nose absorbs the aroma. She squeezes the side of my head, as I feel her body shake. Her body tenses as she screams, yelling "Yes, Yes, Yes!" She gushes all over my face. Stephanie's moans are slowly swaying, then she turns into calming deep breaths.

I turned my head, trying to find Brian. He's sitting in the chair close to the bed, completely naked stroking his manhood with his right hand. He is absorbing the scene in front of him. He stands moving closer to us. I am still on my knees, with my body still hovering over Stephanie. I wiggled my booty looking for attention from Brian. Brian climbs onto the bed to mount me. Pushing his cock towards my puckered hoe, he cups my caged clit using my pre-cum to lube my boi pussy. His cock head pushes slowly into my hole,

As he entered, I tightened my cheeks around his manhood. Brian pushed in further. It was Deja Vue. I gasped as he pushed harder. I could feel his balls pounding against my taint. I tried to match his rhythm with my booty as he pounded my hole. My whimpers became faster and faster. He reached around the find my aroused caged clit. He placed his massive hand tightly on the chastity shaft. He stroked the shaft firmly, several times back and forth. I lost concentration, with my mind trying to concentrate on his grasp of my caged clit then back to his cock in my booty.

I tried to refocus on his huge cock that was pounding my boi pussy. I was overwhelmed by the pressure in my boi pussy that contrasted with his strong hand on my shaft. I then felt wet lips on my caged clit. Stephanie wiggled underneath me sucking on my covered shaft. I could also feel my balls puffing.

Brian continued to give me several quicker and deeper thrusts. My whimpers became loud intense moans. Brian found my p-spot once again. Stephanie's mouth had engulfed my caged shaft I filled her mouth with my white fluid. I heard her gasp, then gag. My orgasm surprised her. Brian, feeling my body tense, dropped his load filling my booty. I screamed uncontrollably. It was my turn to calm my breathing.

I could feel Stepanie's mouth licking my shaft. She scooted from under me, to kiss my lips. She had not swallowed all my juices, so as we kissed, she pushed my sweet fluids deeper into my mouth. The three of us fell into a heap on the bed. Brian was the first to move, pushing himself off the bed.

He looked at his watch, saying he had to get to the office to attend late morning meetings. He looked at Stephanie, remarking, "You can stay. Take the rest of day off." Stephanie nodded affirmatively, as she stood up. She picked up her red thong, skirt and crop top from the floor, then turned towards me, asking if she could stay for a little bit. It was my turn to nod yes.

Brian dressed quickly, walked directly to me, we embraced, then kissed. Brian was much taller, so looking down at me, saying, "It was indeed my pleasure getting to know Nikki Madison. Plan to spend the weekend next time. We, glancing at Stephanie, would love to show Nikki around town." Walking towards the door, he stopped, turning back at both of us. He reached into his pocket; he then flipped my chastity key in our direction. Stephanie reached out to catch the key. She tucked the key in her bra bodice. I smiled at her.

Brian laughed, "Well, lass its your decision to unlock her!" He opened the door to leave.

As Brian left, Stephanie held out her hand, pointing towards the table for us to sit. "Do you have time to chat?" We sat. She placed the key on the table. I reached out to hold her hand.

Stephanie spoke first, "We have unfinished business, so to speak. I want, need, more of you. When do you have to leave Seattle? "I indicated that I was planning to leave in the afternoon, but sensing her disappointment I indicated, depending on the flight schedules I might be able to extend until later?" Before I could finish, she asked if I could leave tomorrow so that we could spend the rest of day together, then I could stay with her tonight. She then begged, "Please, please stay!" To give me a little incentive, she spread her legs apart showing her glistening bare pussy. I nodded yes. I could not resist.

Smiling, I used the room phone asking for late check out. Then using the app on my cell phone to check flight availability for tomorrow. Stepanie waited patiently. When I returned to the table, I simply stated, "Girl friend, I'm all yours until tomorrow." Stephanie grabbed the chastity key off the table, then my hand, saying, "Let's take a shower together." We sprinted to the bathroom.

To be continued.