Darling Nikki, Chapter 2: Popping Nikki's cherry

Discussion in 'Fictitious Stories' started by D_Phil_R_Upp, Nov 2, 2010.

  1. D_Phil_R_Upp

    D_Phil_R_Upp New Member

    Jun 8, 2009
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    If you missed Chapter One, a quick recap: Nikki used to be Nick, a pretty twenty-something twink boy, but a hot, odd hookup led to her surprise transformation into a head-to-toe woman, with huge tits and a hot, tight, real pussy. She's a tranny girl, but made an express transition - and possibly a supernatural one. She's had a sexy, probing OBGYN exam and now wants to lose her pussy's virginity.

    I feel like a can of Coke that's been shaken for weeks but not opened...and I swear, when I am opened, I'm going to EXPLODE!

    Ryan helped me get a job as a waitress in the club his buddy Ace works in as a bouncer. I am making a lot of money and getting a lot of favorable attention from the guys that go there, but it's so distracting - and most of them are with their (very jealous) girlfriends. At least I've been making enough money to catch up on rent and buy some new clothes....

    And I love my new clothes - my lacy panties, short skirts, high heels and fuck-me boots. The only thing I haven't bought much of is a bra - I wanted these 40DD tits to be front and center and on display for every guy who wants a peek.

    Last night I had a night off and went to another club. So many hot guys my age, and a lot of flirting and attention. But for some reason, none of them took it to home base. I wondered if I'd missed some part of male/female hookup chemistry.....had I come on too strong?

    I almost got Wyatt, a seriously hot jock stud type I'd gone to high school with, into bed. But I ended up telling him that he knew me (and that I was Nick) before. He'd been making out with a few girls all night, and was so turned on when I told him that, he shot a load in his pants right there, which ended anything before it even began!

    It's now 2 am on a Tuesday. I didn't feel like heading back to the club, so I am at the bar at the hotel next door. An older crowd here, mostly groups of businessmen.

    A few guys are hot, but at this hour, they all seemed to be older, douchier versions of the douchebags I've been dealing with at the club. I put my head in my hands in frustration. Damn, I thought. I always fantasized about being a girl, and how much easier it would be to get laid. But it doesn't seem easier now.

    "Is this seat taken?" a deep voice to my right said. I looked up and the sight nearly took my breath away.

    "No, please, be my guest," I said. The man sitting next to me was amazing. He was so tall and broad - at least six foot four. He was in his forties and very muscular, with a balding, nearly shaved head. His face reminded me of Mike Rowe. His shirt and jeans hugged his hard body.

    He extended his hand. "I'm Jed." I smiled. "I'm Nick....I mean, Nikki. Nice to meet you, Jed."

    We traded small talk for a while; I learned he was an architect and a builder. After a small pause, he looked directly at me and said, "How long has it been since your transition?" I was stunned. He said, "It's OK. You look great, incredibly natural. I'm just curious."

    Hmm....he thinks I am a surgical M to F tranny. "It's been a few months," I fibbed. "Last call!" the bartender shouted.

    Jed looked at his watch. He stood to leave, then turned to me. "Nikki, I'm going to my room - room 435. If you'd like to join me there to continue our chat, I'd love that. If not...it was a pleasure to meet you." He grabbed my hand and kissed it.

    I finished my drink. As if there was any question where I was going. My hands were shaking as I walked to the elevator. I got on with the group of businessmen.

    As we went to 4, one of them whispered, "Man, what an ass on her." Another was trying to cop a feel. I smiled and said, "Good night boys!" as I got off on 4.

    I knocked on Jed's door. He opened it and looked great in his robe. I looked up at him - now standing face to face, he was a foot and a half taller than me.

    He closed the door and wordlessly picked me up, kissing me. Jed's tongue felt magical as we passionately made out. He laid me on the bed and slowly ran his huge hands up and down my body.

    He was still in a tank top and boxers under his robe. He told me to stand. "I love to unwrap my packages," he rasped, as he slowly took my heels off. He undid the strings of my dress. "Woah! Wow!" he exclaimed, when he saw my tits. I leaned back on the bed as he slowly peeled down my panties.

    He looked closely at my wet pussy and then looked at my face. "Your surgeon must have been Michelangelo," he murmured. "You are an amazing woman."

    "My turn," I told Jed. "I love to have a guy put on a show for me." He chuckled and stepped back. He slowly untied his robe and peeled it off.

    He peeled his tank top off, and I could not believe how V shaped Jed was. He had enormous broad shoulders and a narrow waist. He wasn't ripped to the max ab-wise, but was a solid brick wall of muscle.

    He stepped closer and pulled his boxers around his ankles. When he stood up, I gasped. Jed had a nice huge cock, thick and so meaty it curved downwards.

    "You know, as an architect, I always carry one of these," Jed laughed, and pulled out a tape measure. "Go ahead. You know you want to." I measured the thickness of Jed's dick. Six inches at the base.

    Then the length of his cock on top, from his abs. Nine and three quarters inches. And from underneath his cock? Eleven inches. He was getting harder and harder as I measured.

    I kissed his shaft and then started to slowly take it deeply into my mouth and throat. After a few seconds he said, "Nikki.....lean back first." I laid back in the bed.

    He kissed my tits and laid his face inbetween them, then kissed down my belly.
    He looked at my new, pink pussy and then at me. "Has anyone been inside of you yet?" I shook my head no.

    He ran his huge fingers along my clit and I almost came. He looked closer and shook his head. "I've been with other transgendered women before, Nikki, and I've never seen such a realistic pussy....you're getting wet!"

    "You ain't seen nothing yet, Jed - keep working on my pussy and you'll be soaking wet!"

    He laughed and took that as a challenge. For what had to be an hour, Jed licked, sucked and rubbed my pussy. He spent time licking and sucking on my clit, tongue fucking me with his huge Gene Simmons tongue, and sticking his fingers inside my tight twat.

    Finally I could wait no longer. "I'm close to gushing, Jed."

    His face popped up from between my legs with an excited look. "You're a gusher?" He started licking my pussy furiously and ramming his fingers inside.

    I started to moan loudly and grabbed my tits, and then I felt the Coke can explode - my pussy twitched and I felt honey gush out of me.

    I must have made a lot of noise, because a few rooms down the hall, a group of guys said, "Yeah, bitch!" and started clapping. Jed looked up at me - I had soaked his face. He looked blissful. "Oh, baby.....damn...." he said. His cock was ramrod hard. I knew what was coming next.....

    To be continued....
  2. Empathizer

    Verified Gold Member

    Oct 12, 2009
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  3. D_Phil_R_Upp

    D_Phil_R_Upp New Member

    Jun 8, 2009
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    Jed went into the bathroom for a second. I watched him come out and took a deep breath when I saw him walk towards me. He was just such a big man, in every way.

    He laid on the bed and reached over to stroke my body. He put his hands on my tits. "I....I can barely cover these beauties," he said as he cupped my tits. "A definite two hander!"

    I leaned over to him and wrapped my small, delicate fingers around his massive shaft. "Yeah, you've got a two hander, too...." I started to lick the underside of Jed's cock and he moaned softly. The more I licked, the harder his shaft got.

    I laid back on the bed and pulled Jed to me. He straddled my waist and pushed his cock between my tits, holding himself against the headboard. Jed started to fuck my tits, slowly at first and then making them bounce. At the same time, I worked the head of Jed's cock into my mouth.

    Jed was in heaven. "Ohhhhhh....fucking huge tits....huge bouncing tits.....aaaahhhhh." After tit fucking me for a few minutes, Jed put his face in my boobs and kissed and licked them.

    He stood up and lubed his cock. "You want it?" Jed asked me. "Yes, yes, YES!" I nearly screamed.

    Jed pulled me to the edge of the bed and pulled my legs wide open. The huge purple knob started to slowly penetrate me. I moaned - it was definitely very different than all the times I'd bottomed, all the times I'd been fucked in the ass.

    It felt like an enormous wall of pressure, and as Jed's shaft really started to penetrate me I felt jabs of pain. But the pain would dissipate and burst into a buzz of pleasure. The more friction I felt, the more swollen my clit got.

    Jed was about halfway in when he asked me, "Do you like it slow and easy.....or fast and rough?" I smiled at him and mocked a yawn. "Bring it, big boy," I challenged.

    Jed grabbed my ankles and plunged the rest of his cock into my pussy. I gasped and moaned....it hurt like hell but I wanted more. Jed surprised me by picking me up and holding me. He walked me around the room, with his cock pushing into my pussy with every footstep. When we got to the window, he sat me on the windowsill and started to pump my pussy with long strokes.

    He whispered as he fucked me, "I bet you'd love to put on a show....." The idea of other guys watching us made me even hotter and wetter. Jed chuckled. "Yeah, I got your number, don't I?"

    He picked me up and stood me next to the bed. He looked so amazing as he laid back, hands behind his head, ramrod hard. "Climb aboard," he commanded. I straddled him and started sliding down his pole, then started to bounce up and down on his cock.

    "Cmon babe.....fuck it! fuck it! fuck it!" he muttered as his cock filled up my tight, new pussy. It felt like it was getting even bigger inside of me.

    Suddenly, we heard a crash in the hallway. I pulled off of Jed and he opened the door. It was the four young, drunk, businessmen who'd been at the bar. They'd been listening.

    "Dudes....don't listen. You can watch. She loves to be watched." The four guys stepped into the room. They were a hot bunch: a lean hipster guy, a very tall beefy football-player type, a dude that looked like he could be Jed's younger brother, and a very dark skinned, bald black man.

    Jed again pulled me to the edge of the bed and started sliding his cock back in me. He was smiling. "Making it a night to remember, baby girl...." He started to really jackhammer my pussy with his pipe, and I moaned and groaned and squirmed, feeling the pressure inside of me build.

    Jed started to pick up the pace and as he did, I could see the four dudes, now stripped naked, stroking and watching us fuck. I could only focus on Jed's shaft and Jed's face, inches from mine, sweating and kissing me.

    "Such a sweet little bitch...you love having my big cock stretching open your cunt, don't you? Don't you?" he said as he ran his fingers through my hair. "Say it. Say it loud."

    "Yes, Jed....I LOVE THAT YOUR BIG COCK IS STRETCHING MY CUNT OPEN!" He started to slam me even harder, and I knew he was close to cumming. He laid me flat on the bed and raced to an almost jackhammer pace, and then slowed a little. His moans turned to a roar, and as he bellowed, "Take it! Take it!" I felt his load firing into my pussy. It felt like Jed filled me up with his breeder juice.

    Jed pulled me onto his still hard cock and kept fucking. My pussy felt amazing filled with his monster load, and Jed started aiming for my clit.

    As he pulled me closer, the lean hipster dude came to the side of the bed. He grabbed his seven incher and pointed it at my tits, and three long ropes of cum barreled out of his cock. He grabbed a fingerful and pushed his fingers into my mouth, and I tasted his sweet load.

    The hot black dude came to the other side of the bed. He had a BBC that looked to be as big as Jed's, and it bounced as a huge load ran out of the cockhead and down the sides of the shaft. He shook his cock and his load spattered all over my tits.

    Jed motioned for the hipster dude and black dude to hold my legs open, and the other two guys knelt by each side of me in the bed. They jacked as Jed continued to ride my now sloppy wet cunt.

    I was so turned on. The taste of cum, the smell of it, the sounds of all their voices, and the feeling I had of being under, above, next to Jed...it was making me crazy.

    "Fuck me hard!" I cried. Jed complied and got much rougher. That did it and I.....I.....I lost it. I screamed and moaned. And as they all watched, I came....gushing some juice onto Jed's cock as it kept pounding me.

    That was enough for the other two guys, who simultaneously shot their loads on my tits.

    Jed grunted again and from his vantage point at my feet said, "Open wide, babe." I did, and he pulled his cock out of my pussy. He grabbed his python and aimed for my face. Amazingly, when he came, he shot far enough to land on my face and in my mouth.

    After the drunk rowdy guys got dressed and took off, I curled up next to Jed. We were both speechless for a while. "Thank you," I said. "Thank you for feeding the naughty girl in me. That was exactly what I wanted."

    "You're beautiful," Jed said, and slowly, gently kissed me. After another moment, Jed said, "I have a confession. I was pretty sure I knew who you were when I first saw you."

    I looked at him, completely puzzled. "What do you mean?"

    He paused, then kept speaking. "Well, I like t-girls, and although you look more natural than anyone I've ever seen....you reminded me of someone I'd seen before. And I turned out to be right."

    I was lost now. "Jed, you're an A plus, A1 stud. I would have remembered meeting you."

    "I'm not sure we met face to face, babe," Jed said. "But I remember seeing you at a homecoming game when you were in high school, and thinking how petite and beautiful you were then. When I saw you tonight, I was beside myself thinking that you'd actually transitioned...into the beautiful butterfly I saw."

    I smiled and kissed him. But I still didn't quite understand. "So, you go to all the games at Central High?"

    Jed chuckled. "No, but my son Wyatt was a football player there. I think he was in your class."

    Oh. My. Gawd. Hot, ab-licious, blond Wyatt, the focus of so many of my high school jack off fantasies, was Jed's son.

    Jed chuckled. "Yeah, I know...you like Wyatt. Hell, Wyatt knew that too! Lots of girls like my son. He takes after his old man....in a lot of ways."

    My mind was blown. I couldn't think about it any more tonight, though. I snuggled against Jed's huge body, and still half-hard cock, and went to sleep, totally satisfied.....
  4. D_Phil_R_Upp

    D_Phil_R_Upp New Member

    Jun 8, 2009
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    about to write more….
  5. ilpallazo

    ilpallazo Active Member

    Mar 20, 2006
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    At last! Can hardly wait
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