Kinky Travels - Jessica Joins Us

The More the Merrier - Jessica Joins the Party

This chapter is a continuation of Nikki's hook up with Jason and Clare during her business trip to San Francisco. For story background Jason, one of the hotel's bartenders was privy to Nikki's secret. In the previous chapter Nikki invited Jason to her room. With Nikki's permission Jason invites Clare, another bartender, to join their party. The story now continues with Jessica joining the party at Clare's invitation. Whew! To catch up you may want to read the two previous installments of Kinky Travel.

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. The alter ego, Nikki, emerges, almost daily outside of Jamie's work responsibilities.

This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. The life story of Nikki Madison's Kinky Adventures is 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. Nikki is very cognizant of the importance of safe sex. She uses a highly effective preventive medication that reduces her and her partners' risks for disease.

Closing the door behind her, Jessica's eyes widen as she surveys the scene in front of her. I was on my knees with Clare's sissy clit filling my mouth. Jessica's sudden arrival startled Jason, he stopped kissing Clare to motion Jessica to his side. Clare remained intensely focused on me, as my mouth was now engulfing her clit.

When Jason turned to greet Jessica, she noticed, apparently for the first time, his enormous cock. She exclaimed, "Wow, I heard you were huge!" Jessica and Jason embraced, wrapping her hand around his massive cock as they kissed. Never letting go Jessica led Jason by his manhood to the bed... my bed, pushing him down on his back. Jason laid back naked on his elbows, watching Jessica undress in front of him.

She dropped her beige uniform jumper to the floor, pulled her blue blouse over her head. She stood before him in her skin toned pantyhose, sans panties and black bra. He ample boobies were overflowing the wired bodice. She seductively crawled to Jason's naked body on the bed. Jason pulled her up his body to kiss and embrace.

All of this was all a blur to me as Clare forced my mouth back onto her sissy clit. She was now fucking my face. Her thrusts became faster and faster. Her precum was dripping down my chin. I couldn't get enough of her sissy clit. As best that I could I wrapped my mouth tight around Clare's clitty bobbing my head quickly up and down with her pounding motions. She held the back of my head pushing it with each thrusting motion.

She slightly pulled back. "Are you ready sissy bitch?" I wasn't, but then I was. I moved my head up and down, then I felt the sensation of her clit explode. Her sweet fluid filled my mouth. As I swallowed a stream of cum, a second surge came from Clare's shaft. I cherished it. I swallowed more of her thick liquid. Clare pulled me up to kiss me. I exchanged a small bit of her remaining fluid in my mouth with her. As we kissed our tongues intertwined. My heart was thumping, I took several deep breaths trying to calm myself down.

As Clare and I continued to embrace, I could hear Jessica moaning heavily. Jessica, top, was bouncing up and down Jason's huge cock, her pantyhose was ripped. Jason was holding Jessica at the waist, controlling her up and down, to coincide with his upwards thrusts. Holding each other with arms around our mid sections, Clare and I turned to watch. Jessica's moans swiftened, she shrieked incoherently at Jason, then screamed with a massive orgasmic scream. Jason continued his upward thrusts, filling her pussy with his load, then collapsed to take a few deep breaths.

Being a voyeur watching someone else experience orgasmic pleasure has always given me a tingling feeling throughout my body. Clare, then caught my attention when she began squeezing my caged clitty, "Nikki who holds the key?" I stammered, "I do. I am self-locked today!"

Looking directly in my eyes, "Give the keyto me!"

I broke our embrace clumsily trying to find my clutch. I finally found it on the floor next to the chair. Searching uncomfortably though it, tossing out contents of the clutch I held up the key.

Clare grabbed it out of my hand, smiling, Clare said "I will take the key sissy bitch!" She motioned me to approach her. I moved to the spot she pointed at directly in front of her. She cupped my encased shaft, inserting the key in the lock. She unhooked the device, sliding my sissy clit out its restrictive rings, holding me in her palm. I became aroused quickly. She took her finger to catch the drippings of my pre-cum, then swiftly pressed her coated finger to my lips. I opened wide, as she pushed her finger inside my mouth. I eagerly licked her finger dry.

She then turned me around facing Jessica and Jason. She then placed my arms behind my back, pushing my head down, to rest my chin on my upper chest. They stayed on the bed, captivated by the power exchange between us. Clare sat down on the edge of the bed.

I stood motionless in the middle of the room; all eyes were fixed directly on me. I felt very vulnerable.

Clare sternly ordered me to pleasure myself. I closed my eyes, clutching my shaft with the palm of my hand. As I gently stroked, I could feel my sissy clit becoming even bigger. My sissy clit is not huge, but not tiny either. I'm not embarrassed stroking myself to an audience, but there is a bit of humiliation when you are not in control. Clare broke the silence again, "Make it last Nikki!"

I continued to squeeze the shaft, still holding my breath slowly stroking. I was now fully aroused. The stroking resulted in a slow whimpering noise from me. I could feel the pressure building in my hand. Clare again ordered me to make it last. I tried to keep focus on Clare's demand slowing the pace of my rubbing. I took deeper breaths to calm down.

My legs were becoming weak. I so much wanted to cum. I needed to cum. More deep breaths. The room became quiet. Clare, sensing my predicament, told me to, "Do it now. Don't spill a drop.!"

As my juices began to flow freely from my sissy clit, I cupped my right hand to catch my load. I opened my eyes, as Clare stood to move closer to me. She moved my hand to her nose. She smelled my juices, dipping a finger into my hand. She placed that finger in my open mouth. I cleaned Clare's finger of my juices.

She then took the finger of my other hand, dipping the finger into my hand, then motioned me to place my finger in her mouth. She licked my finger dry. "Nikki, you smell and taste yummy!" Pleasing her made me smile. She then tipped my cupped hand to my mouth; I slurped it dry. Clare, stared into my eyes, "Are you still thirsty Nikki?" I nodded yes. She motioned to Jessica, who was now sitting up on the bed. "Jessica needs your undivided attention! Clean Jason's load from her pussy."

I crawled up the bed, Jessica opened her legs to great me. I pulled what remained of pantyhose down her legs, then nestled my face between her thighs. Kissing and licking, I moved my tongue up to her inviting pussy. Jessica pushed her pelvis up to greet my tongue and lips. Parting her vagina lips, I licked her inner walls, catching the drip of Jason's load, now mixed with her own juices. Her aroma and taste were very sweet. I was now on my knees with my booty in the air with my boi pussy exposed. I heard Clare say to Jason, "She's all mine!"

Jessica was grinding her pussy in face. She moaned with each flick of my tongue. Her fingers were already massaging her clit. I start slowly moving my tongue from side to side, then tightening my tongue, I moved up and down. Jessica reacted to the firm tongue moving up and down I could hear her soft moans turning into more intense lower body movements,

Gently I continue to move my face deeper into vagina. I placed two fingers inside widening her vagina lips, 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 me take control. 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.

Jessica's whimpers become quicker in response. My face becomes wetter. Her juices are pleasing on my tongue, 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. Jessica's moans are slowly swaying, then she turns into calming deep breathing.

Clare climbs onto the bed to mount me. Pushing her sissy clit towards my puckered hole, she smears my boi pussy with lube that had dropped out of my clutch. Her clit head pushes slowly into my hole. As she entered me, I tightened my cheeks around her swollen sissy clit. Clare pushed in further. I gasped when she pushed harder. I could feel her balls pounding against my taint. I tried to match her rhythm with my booty as she pounded my hole. My whimpers became faster and faster. She reached around to find my aroused clit. She stroked the shaft firmly, several times back and forth. I lost concentration, with my mind trying to concentrate on her grasp of my clit then back to her sissy clit in my booty. I could also feel my balls puffing.

Clare continued to give me several quicker and deeper thrusts. My whimpers became loud intense moans. Clare found my p-spot. Feeling my body tense, she dropped her load filling my booty.

Spurting my load, I screamed uncontrollably. It was my turn to calm my breathing. I fell on top of Jessica. Pulling her sissy clit out of my boi pussy, Clare fell on top of me. I rolled over, Clare lowered her mouth to mine, kissing me full on the lips. She then whispered in my ear, "Tonight has been wonderful Nikki. I want an encore!"

Jason had been watching the threesome scene in front of him. His hand was jerking his large cock. He picked up a glass to spurt his load, smiling directly at me, "For your enjoyment later!" I licked my lips.

Jessica wiggled out from under us, looking at her watch, saying "I have to get home!" She hurriedly dressed, throwing her torn pantyhose in the trash can by the desk. She leaned back down to kiss Clare, thanking her for the invite. She then kissed me, smiling, "Thank you Nikki." She then stood, embraced Jason, squeezing his cock, she murmured loudly, "You are wonderful Jason! I want a repeat performance with you soon!" She quickly walked out the door.

I rolled off the bed, excusing myself, I headed to the bathroom. I tidied up, then returned to the bedroom, finding Clare and Jason talking. They stopped when I entered the room. We chatted for a few minutes, exchanged cell numbers, Clare glanced back at cell phone pinging. She read her incoming text to herself, then abruptly said she had to leave. She jumped off the bed, she picked her bra off the floor, turning me to help her dress, fitting her low-cut blouse in over her head, slipped her back into the red pleated skirt. She motioned me to come to her.

Jason tossed her my clitty cage. She squatted, pushed my balls, through the ring, attached the silicone shaft, then quickly locked the cage. She stood up, dropped the key into her bra, smiling back at me, "I assume you have another key at home?" I smiled back and said yes. She then said, "Good for you but it should be an interesting experience today, going through Security!" She kissed me, then quickly turned to leave, exiting the door in a hurry. I stammered, to no avail.

I looked at Jason, he grinned back, handing me his filled glass, I drank the contents, turning back to him simply saying, "Tasty!"

He just said, "Let's get some sleep Nikki!" We climbed into bed." We snuggled; he playfully rubbed my sissy clit through my cage. I whimpered. He then smeared my hole with the lube that had been in my clutch. Thinking I was going to get his wonderful cock again instead he pushed an anal plug in my butt. Jason said, "Perfect, I don't want to sleep in the wet spot." As we cuddled; he rested his huge cock into the crack of my booty, we soon fell asleep exhausted.

I woke up to Jason kissing my neck. She was leaning over me, fully dressed. I grabbed his arms trying to pull him back to bed. He was resisting. "Nikki darling, I must run. I want to stay but I have a few things to do before working again tonight. Last night was fantastic!" Jason kissed me again; our tongues intertwined. As he pulled away, I leaped out of bed to embrace him.

He broke our embrace, "If I don't leave now I never will." I followed him to the door, and we kissed again. He cupped my caged sissy clit. He grinned, as he walked out the door. I stood naked at the door holding the door, watching him walk to the elevator. He, turned then blew me a kiss goodbye.

Nature called I quickly strode to the bathroom. With the chastity still on, I had to sit, a gentle reminder that my clitty was still caged. Then I recalled that I didn't have the key; Clare had it.

I immediately stepped into the shower. It was now time for Jamie to reappear. As I cleaned up, I started to dress in my male clothes. I slipped on a black satin thong, that fit snugly over my sissy cage, I kept my booty plug in. I was in a predicament, I could remove the plug later, but I was at a loss as what I was going to do with chastity cage. Looking down at my cell phone, I noticed that it approaching 11 am. I needed to check out, get to the airport then catch my flight home. I finished packing, then I called the bell desk to help me with my bags.

The bellman arrived, handling me an envelope, addressed to Jameson Madison. He was loading my bags on his cart, as I opened the envelope. Out popped the key in my hand, Inside was a note from Clare, that read.

"Girlfriend last night was pleasurable. You are a stunning and kinky woman that I want to get to know better. Hurry back to San Francisco; or I will rendezvous with anywhere, anytime. Safe travels Nikki! Kisses Clare. There was an imprint of her lips in red.

BTW, sissy girl you only have the key because I don't want you to be embarrassed at security, this time. "

The Bellman left with my bags, when I tipped him and asked him to call me a cab. I dropped my pants, unlocked the chastity cage, then removed it from sissy clit. I would have put it in my checked luggage, instead I dropped it in my briefcase. I said to myself, I will deal with it later. I kept my butt plug in my booty.

I checked out at the front desk, walked across the lobby to the front door, the doorman whistled for the cab, opened the door for me as I slid into the backseat. He did a double take, I simply smiled back, wondering if he knew my secret.

As I rode to the airport, my thoughts flashed back to my stay. My trip was memorable in more ways than one. More importantly, I knew I would be back. I will cross paths with Ken, Clare, Jason and Jessica in the future.

Your comments and feedback are always welcomed.