Jenn and Ted Go Private

Jenn and Ted Go Private

This story has been posted to Literotica. com with the full knowledge of the original author under my pen name, NikkijMaadison. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author. I edited this story using Microsoft for spellchecking, flagging punctuation, grammar review, and as a dictionary. I use any other suggestions only as a guide. You may discover mistakes. That will happen.

© Copyright NikkijMaadison - All rights reserved.

This story is a sequel to 'Jenn and Taylor Are Bed Partners.' Taylor spots one of her work colleagues, Ted, who is one of the executives at the firm that employs Taylor as David. Ted is a bigwig at the Financial Investment Firm. He doesn't know about David's Taylor persona and of course he has no idea that Taylor is a part-time sissy.

On Friday night, I met Ted. He called me his Princess. I will become his Princess, tonight but I also have to secure that Taylor's, err, David's identity is safe.

This story contains sexual activities and situations between consenting adults. All characters are above the age of eighteen. Any similarity to any individual, living or deceased, or location is coincidental and unintended. The story will be told in the first person.

Boys Make The Best Girls

I waited a few moments, then confidently strutted to the bar. As I strolled alone to the bar, all eyes seemed focused on me. More than one male stared at me as I strode towards them, and all eyes were on my booty as I walked away.

The white silk full-length cape covered my body. I was Princess Butterfly in my white and black feathered wings. As I strutted across the bar, my wings fluttered with each step.

I spotted Ted at the bar; he was smiling. He motioned for me to join him. I did. Tonight, adorned in all white, I was indeed his Princess Bride. I am the epitome of irresistible sissy innocence.

He stood, and he kissed me on the cheek, remarking, "Hello, Princess. You are a woman who keeps her promise!" I sat next to Ted, and Julian, the bartender, placed an Italian Spritzer in front of me. He also refreshed Ted's Bourbon Neat.

When I crossed my nylon-clad legs, my white silk cape fell to the side revealing the lacy top of my thigh highs. Ted was in awe once my lace top thigh highs were visible. He took the seductive tease as he consciously placed his hand on my knee. He couldn't stop smiling, remarking, "Jenn, will you be my Princess Bride, tonight?"

Blushing, I replied, "Ted, if you remember, I keep my promises!"

He nervously laughed, responding, "Yes, I do!" He gently squeezed my knee.

One of my biggest turn-ons is knowing that I have turned someone else on. Tonight, I have promptly accomplished that with Ted. Lingerie is not just clothing. It's a celebration of who I am. Never underestimate the power of a pair of heels, pink lipstick, and a pair of legs clad in lacy stockings.

No respectable T-girl is ever completely naked, and I love exposing suggestive hints of my body to men. I am first and foremost a sex object. Men are infatuated with me; I am the straight male's fantasy, and once they are with me, their fantasy becomes a reality. I always try to remember that I am just a decoration and a stress relief toy when I am Jennifer Nicole. I don't attempt to be anything more.

We exchanged idle chat, then surprisingly remarked, "Is your girlfriend okay? You were in a big hurry to find her last night." He didn't elaborate, but I sensed that he wasn't happy with me leaving abruptly.

Smiling, I replied, "Yes, Ted, she's fine now. She was experiencing a little anxiety. She may come by the Club later tonight. But let's talk about me and you right now." And we did, or rather, we started to!

Our Small Talk Set the Hook

Tonight, I wanted the conversation to center on me. He said I was his Princess. It did not. The conversation was all about Ted and his perceived needs. Unfortunately, the conversation was typical of many men like Ted.

I don't begrudge him, and I am not judging him, but I learned was 'that his wife was out of town visiting friends and family.' That he stayed home due to his work commitments.' Then the classic, 'That she doesn't understand his sexual needs.' Followed by 'His wife is vanilla when it comes to sex!' I didn't need to hear his reasons or justifications; I just wanted to surrender myself to a man tonight.

I needed to step up my game, to turn the conversation back to me, So, I did. I became playful and engaging. I turned on my charm. Ted was taking the hook.

He gently touches my elbow, my arm, and the top of my hand when he talks,. I gently trembled each time. Ted loves to caress my knee. When he gently rubs my skin through my nylons, I quiver inside. When he tenderly touched my thigh, I spread my legs, giving him access to my inner thigh. Ted took the hint, and his fingers roamed up my leg. With each caress, his fingers roamed further.

I love being touched tenderly, and Ted's touch was indeed affectionate now. Flirtatiously, I tightened my legs, capturing his exploring fingers. My eyes were focused on his. I smiled and quickly spread my legs even wider. His fingers explored deeper, tenderly caressing my inner thigh. I noticeably shivered. Ted abruptly stopped.

Leaning my head closer to Ted, our foreheads touched, and I whispered, "Ted,

I know this may be wrong, but your hand up my skirt makes me blush." I warmly kissed him. He kissed me back, and he did not remove his hand from my inner thigh.

Ted replied, "Princess, you are playing a dangerous game! You are a risk and a mystery." I consciously played coy, slowly running the tip of my tongue along my lower lip. It was Ted's turn to turn on the charm.

When a man affectionately calls you Princess, you want to truly be his Princess. You want to believe him, and you want to live it. When Ted calls me Princess, I melt. Ted knew it.

Smiling, I replied, "Sweetie, the fact that I am dressed, a little naughty, confirms that I'm here after what you're here after! Sweet Ted, I will be your Princess Bride tonight!" I warmly kissed him on the cheek.

There was intense sexual heat building between us. We were toying with each other's emotions.

Occasionally, Stephanie would stroll through the bar area to check on me. Each time we exchanged smiles. On the last stroll, she gave me the thumbs up; I nodded. Without delay, Elizabeth, Charlotte's Assistant, tapped me on the shoulder, whispering, "Jenn, your private room is ready!"

I instantly stared into Ted's eyes, gently gripped his hand, I said, "It's Showtime, Ted. Let's misbehave!" I quickly stood, as did Ted. I demurely handed him the end of my leash and motioned toward the private room hallway. Ted proudly led me away from the bar area. I strolled a conscious step behind him.

It's Showtime

I quickly keyed the digital door lock to access the private room. I consciously did not lock the door as I faked locking it.

Once inside the room, Ted grabbed my hand, pulling me toward him. We embraced, and Ted pressed me up against the inside wall. Even in 3" heels, Ted towered above me. Dropping my cape to the floor, I wrapped my arms around his neck, pressing my scantily clad torso against him. Ted, holding me at the waist, pressed his body into mine. I was his prize.

Ted hastily kissed me on the lips, not passionately, but hungrily. I returned the kiss, tilting my head to accept another kiss. This kiss was not passionate either; Ted appeared overly anxious now. I needed to slow him down, but his hands were now tightly gripping my booty cheeks. His voice sounded uneasy as he spoke, "Princess, I need to fuck you now."

My body is now shaking from head to toe. I'm the one anxious now. I sensed that he was very nervous. I wanted to taste his cock, but I wasn't ready yet. I softly replied, pushing his "Ted, let's go slow, I want to enjoy this moment with you."

Ted took several calming deep breaths. He slowed down. Caressing my booty cheek with one hand, and with the other, he held my chin, this time kissing me gently. As we exchanged soft kisses, my heart began to race. We were now in no hurry.

My arms are wrapped around his neck. His arms are back around my waist, and he's holding his body tight against me. Ted runs his lips along the edge of my cheek- slow nibbles and pecks. I moan softly. He backs away slightly, to softly peck his way to my right ear lobe, gently kissing and licking my lower lobe.

He gently blows into my ear. The heat is continuing to build in my body. I began whimpering. I needed him now. I lowered my arms with both hands to caress his cock through his chinos, staring into his eyes I added, " Sweetie, your Princess wants your cock inside her now!" He ignored my tease.

Ted breaks his silence, "Princess, you smell delightful, your skin is so soft!" He paused, adding, "I love caressing your smooth body." Ted knows how to be charming. His sweet words were captivating. Staring into his eyes, I became mesmerized.

Pushing back slightly, I gently placed two fingers on his chin, gradually tilting his chin to the left. I softly run my fingers to delicately trace his ear lobe, and his neck. I am not rushing; I take my time. It's my turn to be the tease. He moans.

I softly whispered, "Your Princess wants you naked!" I gently edged my hands down his torso, unbuckling his belt, enabling his pants to drop freely around his ankles. His cock is visibly aroused and with two hands, I pull on the hem of his silk boxers, freeing his cock from the fabric constraints.

Ted kicked off his shoes, keeping his gartered knee-length socks on. I suppressed my giggles.

His cock is sizable, not the largest I have sucked, but still Ted's cock was large and circumcised. His cock is bobbing uncontrollably. With one hand, I caressed his shaft, with the other, I tenderly cupped his massive balls, squeezing each one separately between my thumb and two fingers. He moaned as I gently rubbed his balls. But I still needed Ted completely naked. That was our plan.

I pushed back slightly to unbutton his blue dress shirt. Staring into his eyes, I unhooked each button, teasingly running my tongue along my lower lip. When I unbuttoned the last one, Ted eagerly removed his skirt, tossing it to the floor. On my tippy toes, I pushed my mouth into Ted's face, mischievously running my wet tongue along his lips.

His hairy chest is muscular. He's no longer a young stud; his upper body is not toned. Standing before me, he still looked anxious and nervous.

I pressed my lower torso into Ted's naked body, and for the first time he felt my caged sissy clit against his nakedness. When I pressed my sissy clit into his crotch, he gasped and pushed back slightly. His reaction felt awkward. He was no longer projecting his confident self.

Am I His First?

Staring into eyes once more, I whispered, "Is anything wrong, sweetie?" He shook his head no. I spoke a little louder this time "Sweetie, let's get comfortable." I led Ted to the sofa. We both sat, and I pushed my body close to him, gently pressing my nylon-clad legs against his naked body. I gently held his hand, guiding his fingers toward my silicone-caged shaft. He clumsily caressed my sissy clit. I surmised that I might be his first sissy encounter. Was he having second thoughts?

Whispering, "Sweetie, it's okay, Jenn is your Princess tonight!" He started to reply, but I placed two fingers to his mouth, adding, "Sweetie, let your Princess guide you." I knelt before him, pushing my hair to the side, and spread his legs wide so I could wedge my way inside his inviting thighs. His cock was no longer fully aroused.

As I moved closer, my eyes remained directly focused on his eyes, I whispered, "Ted, am I your first sissy?" He nodded his head. In a gentle whisper, I said, "Then just follow my lead, and your Princess will amaze you!"

And I did! I started kissing his still growing cock. He moaned at the touch of my tongue. I ran my tongue from side to side up the front of his shaft. He was now semi-aroused as I sucked his cock. I love it when a cock grows in my mouth. Ted, squirming, moaned softly. "Slow, Princess, slow!"

I wanted to, but I also wanted his cock in my mouth, so I kissed the tip of his cock. I love it when my men manscape their crotch area, but Ted was a little too hairy. Nevertheless, his cock has a nicely shaped helmet, and I joyfully twirled my tongue around the tip of his cock head. When I closed my lips around his engorged head, the sensation of his smooth, fleshy thickness filled my mouth. Ted's whimpers turned into soft moans.

Cock, hard or soft, feels so incredible in my mouth. Ted's sweet cock was no different. As I inched my lips down his shaft, Ted held my head firmly in his hands; he was guiding, not pushing my head down, and I sensed the tension in his body. Ted might be ready to explode but I wasn't done licking and sucking. I firmly pressed two fingers around his immediately above his balls. I needed this pleasure to endure for as long as possible. I needed to slow him down.

Ted was now fully aroused. Ted's cock was throbbing in my mouth. I bobbed my head up and down his smooth shaft, inching my way down to my fingers at the base. Deep-throating Ted was not difficult, and I wanted all of cock in my mouth

His cock went deeper each time. His moans increased.

As I bobbed up and down, I needed to catch my breath, and each time I did, Ted gently pushed my head back down his shaft. Ted was on the edge, and I knew it too. He wanted to explode, and voiced, "Bitch you love this, don't you? I know you do." I was surprised at his choice of words, snickering to myself, I presumed I was no longer his Princess.

So, I grinned up at him, "I just love your cock, Ted!" Every guy loves to hear that, but I meant it. Sucking cock gives me dominance over his pleasure. And my ultimate pleasure was controlled by the chastity cage constraining my sissy clit.

It was testing the cage to its limits. I whimpered. My whimpers were genuine.

Ted pushed my head back onto his cockhead, so I firmly tightened my fingers around the base Ted was now fighting my edging. Ted gently pumped his hips, slowly fucking my mouth. I began to drool as Ted was pumped faster. He was getting close, and I tightened my fingers again. I twirled my tongue along the underside of his shaft.

He gripped my leash with one hand and my hair with the other. I gasped again at the pressure building on my caged sissy clit. He was ready, and I was prepared for his explosion. I could feel his cock throbbing. Now was the time. I tightened my lips and mouth around his shaft. I released my fingers and willingly relinquished control. Ted moaned uncontrollably as he exploded a gush of cream into my mouth, which was quickly followed by a second spurt. His cream flooded my mouth. His orgasm was controlled and quiet. He did not scream.

His cream was dripping from the corners of my mouth down my chin. He dumped two loads into my mouth. I did not swallow.

Ted's cock was throbbing in my mouth. My mouth squeezed his shaft, holding him inside. I did not want to release him from my mouth. I tried not to gag. I slurped the remaining cream from his cock head.

My mouth was filled with his load, and I crawled up his torso. As I leaned in to kiss him, I placed my hands on his knees, seductively swaying my body. I wasn't sure whether he was prepared to taste his cream yet. But the plan was to kiss him. I pressed my mouth against his, pushing my creamy tongue into Ted's mouth. He willingly accepted his cream, and the overflow drooled down my chin. His cream drooled down his chin.

Ted took two deep breaths. He spoke softly, "Princess, who taught you how to suck cock? That's the best blow job I have ever had!"

Using my tongue and fingers, I licked his cream off my chin, remarking, "Sweetie, boys make the best girls and sissies are the best cocksuckers!"

Surprise, Surprise

The plan was for Taylor to position herself outside the door and listen for the right moment to join us.

Ted, using my leash, gently pulled me closer toward him. I sat on his naked lap, side-saddled, facing the door. Ted's cock was still throbbing, and I wiggled my booty as I sat. I could feel the heat on my buns. My caged sissy clit was now fully exposed and pulsating. Ted gently placed his fingers over the cage, softly caressing my shaft through the silicone cover. This time, Ted showed more confidence. He was playfully running his fingers along my shaft. My predicament genuinely amused him.

Grinning he remarked, "Princess, what do we do about your locked cock?"

Before I could answer, the private room door burst open, and Taylor walked in. She wore a mask covering her face. Locking the door behind her, she did not immediately speak as she hurriedly walked toward us.

Taylor's entrance caught Ted completely by surprise. He instantly turned his head toward me. "Who is this Princess?" He did not remove his hand from my caged sissy clit.

Acting surprised too, I replied, "This is my friend Taylor!" Ted's reaction was 'Oh!"

Taylor sat in the high-back chair facing us. As she sat on the edge of the chair she spread her knees so that her dangling cock was visible. She quickly removed her mask, remarking, "Tonight, I'm Taylor, but you may know me as David!"

Ted tried to push me onto the floor, but I swung my arms around his neck. He blurted, "You bitches trapped me!" He finally stood, and I quickly moved away. He placed his hands on his hips. He was trying to authoritative, but he was buck naked, and his cock was still semi-aroused.

Taylor spoke, "Ted, no one trapped you. Remember, last night you approached Jenn. And when I recognized you, we left. I didn't want to be compromised, and I didn't want to compromise you." It was Taylor who was projecting the power.

Ted responded, "So what's this all about now. So, you caught me... err, trapped me! I'm just living a fantasy! I'm not gay. So, what now?"

I attempted to speak, but Taylor stood and interjected, "Ted, if I wanted to trap you, why would I be wearing a sheer bodysuit, with pasties on my nipples with my cock dangling in a sheer skirt?" I chuckled to myself, thinking, good point, girlfriend.

Shaking his head, Ted did not immediately respond, then added, "But, but, but...!"

Taylor continued, "Ted, all I want is for us to coexist in this lifestyle and cohabit as colleagues at work. I don't kiss and tell. I embrace my femininity. Being soft and feminine on my own time feels right!" She paused adding, "And I'm a damn good financial advisor!"

Ted responded, "Okay, okay, give me a minute, David!" Ted sat, dropping his head into his hands. I moved to stand beside Taylor. We embraced. Taylor led me over to the sofa; we sat next to Ted. I sat on the right, Taylor to his left. We sat in silence.

Taylor, chuckling, added, "Besides Ted, each time I see you at work, knowing that you know I'm wearing sexy panties, turns me on!" Ted nervously laughed, Taylor and I chuckled, too.

Ted, raising his head from his hands, remarked, "David, knowing that you are a little naughty and kinky excites me too. Do I call you David or Taylor?"

Taylor quickly responded, "Ted, when you see me dressed like this, it's always Taylor!" She added, "This is not a dream; we just need to agree to rules in the workplace." Ted nodded.

I glanced at Taylor; she glanced back. Our conversation with Ted was going better than we both expected. Taylor then added, "Jenn and I look amazing in lingerie and when we put on lingerie we turn into a cock thirsty sluts. And girls like us know how to please our men!"

Ted was no longer anxious as he smiled at me and then at Taylor.

I added, "Sweetie, are you ready for round two?" Ted smiled and nodded.

Before we could continue, there was a knock at the door, and the voice said, "This is Grace. I'm just checking on my girls!"

Taylor scooted to answer and unlock the door. Grace stepped in and stood a few feet inside the room. She spoke directly to Ted, she added, " My girls are very precious to me."

Ted stood and quickly replied, "Your girls are caring for me!" Grace smiled. And nodded. His cock was aroused. His right hand was unconsciously stroking his cock.

Grace was amused, "I see that!" She turned and quickly left the room. Taylor hurried toward us.

I was standing beside Ted. I placed my hand over his. My fingers consciously caressed his hard cock, I commented, "Do you want to watch Taylor and I first?" I didn't wait for a response. I led Ted to the high-backed chair. As Ted sat, Taylor and I kissed him on his cheeks.

Taylor and I embraced and kissed each other passionately. Staring into her eyes, I remarked, "Taylor, it's showtime!'

Epilogue

And that night, Taylor and I gave Ted a show. Ted was an active and willing participant. David and Ted agreed on work and playtime rules. At work, they privately talked about Taylor but never crossed the line. Ted recommended David for a promotion. One that enables David to work directly on Ted's work team. Business travel is likely in the future.

Ted hasn't been a Fetish Club regular, but when he is at the Club, Ted always has always has two princesses to pleasure him.

To be continued in 'Jenn's Seattle Adventures.'

My motto has always been, 'Don't wear girly things if you don't want to experience girly things!'

As always, your comments and feedback are valuable. I sincerely hope you are enjoying Jennifer Nicole's Kinky Adventures. Please take a few moments to share your thoughts in the comments section. I always want to improve my stories and genuinely need and want your feedback.