Bridging the Gap

By NPhillyDogg/Scedmark

Published on Dec 8, 2009

Transgender

Monday morning. Dad was in the bathroom getting ready for work while I lofted around in bed, enjoying the afterglow of our love making. I couldn't believe how great my plan (to seduce my own biological father) was working. I had always fantasized about changing faces and identities, and then coming back home to Madison County and seducing my dad without him knowing who I really was. It had been easier than I expected. Dad had no idea I was really his long lost son that ran away from home 10 years ago at 15. I mean, how could he really? I had changed sexes with a new face, new tits, and brand new body with a tummy tuck, hip implants, and a butt lift. I had long beautiful blonde hair, soft pouty lips, and a state of the art brand spanking new showroom factory vagina! The best money could buy. All so I could pass as a real woman. No one could tell I wasn't the real thing, not even a gynecologist! Most of the women I encountered hated me, because I was so beautiful and all of their men wanted me. I couldn't walk into a room without every head turning.

My plan had worked beautifully. In fact too beautifully. Dad wanted me to stay here in Madison County and be his stead girlfriend. I wasn't prepared for that. I must admit it sounded better than my original plan; to fuck him silly and then reveal who I really was, breaking his heart and leaving him shattered. Somehow staying here and becoming dad's live-in girlfriend seemed not only appealing, but right in some sorted sinful way. I had always wanted my dad's love and acceptance (oddly though, how I finally achieved it as the woman he's fucking and never as just his son). It certainly got my loins all fired up every time I thought about it becoming dad's girlfriend. The only problem was that everyone in town hated me. They suspected that I was only with dad for money or security or something. The most demanding of them by far had been my former classmate Nicolas Cartwright.

Nick openly accused me of lying about my real reason for being in town. He was a real estate agent, and looked into my claims of settling property here for my deceased grandparents (how stupid was I to say that knowing everybody knew everybody in a small town?). Now he wanted to see him privately in his business office, or he said he'd tell my dad everything he knew about my lies.

I knew it would be in my best interest to just up and leave, to disappear as easily as I came. But I was torn. I was finally getting the type of relationship I always wanted with my father, and now that I was finally fulfilling my wildest dreams, I wasn't quite ready to watch it all go away. I knew I was treading on thin ice, but I needed to know exactly what Nick Cartwright knew, and I needed to know what he planned to do with that information?

Dad finally came out of the bathroom, freshly shaved and showered as he began to dress for work. "You're still gonna be here when I get back from work, won't you Alex...?" he asked, putting on his uniform.

"I have a few errands to run this morning..., but I should definitely be back before you get home...!" I assured him, causing him to grin broadly.

"I have an extra key for you..." he said suddenly, surprising me. I watched as he walked over to his dresser and pulled open mom's old jewelry box. My eyes watered when he turned around, holding mom's old key ring. "This used to belong to my wife..." he said, walking back to the bed.

I sat up, the covers falling down off my perfect tits.

"Lester, I couldn't..." I said, too afraid to touch it.

Dad had always been so guarded towards mom's things. As a child I was never allowed to go near her closet, to look through her draws, or touch her jewelry. Dad had always secretly blamed me for mom's death (mom died in childbirth having me), and never really bonded with me fatherly.

"I insist...!" said dad, placing the keys in my hands delicately. "They've just been sitting in that jewelry box for twenty-five years..., its time they were put to good use!" he smiled, kissing me on the forehead.

I suddenly felt warm all over. I kissed dad on the lips, then reached down between his legs to feel his cock. I wanted him so badly. "That will have to wait til I get home tonight...!" he said, grabbing my hand. "How do you plan to run your errands today...?" he asked, giving it second thought.

"I dunno..." I said, studying the keys as I leaned back against the headboard. "...taxi I guess!"

"You know how to drive, right...?" asked dad out of the blue.

"Yes..." I said, confused by the question. Maybe he wanted me to drive him into work so I could borrow his car...?

"My wife's car is in the garage..." he said, making my skin turn ice cold. "...it's a bit old..., but it was brand new when she bought it! The engine runs perfectly..., I take it out for a spin just to warm it up every couple of month...! But it runs in perfect condition, and it's yours to drive around for as long as you're in town!"

"Gee Lester..., are you sure...?" I asked, my heartbeat racing in my chest.

"Definitely!" smiled dad, putting on his utility belt (the final touch to his uniform). "I'll see you later tonight...!" he said, leaning over to kiss me gently on the lips.

I laid in bed as dad walked out the room. Moments later I heard the front door slam, then heard his car start up in the driveway before pulling off.

I got up out of bed and jumped into the shower, knowing I had to face Nick sooner or later. I preferred to get it done and over with. I used my lavender scented shampoo and lotioned my body from head to toe with special oils designed to make my skin silky soft and give me a radiant glow.

Once I set and blow dried my hair, I brushed the soft curls out and allowed my long silky hair to cascade down over my shoulders. I picked out one of my sexiest dresses, a pair of high heel stilettos, and painted my face perfectly. I opened the garage door, then took mom's old Rivera out for a spin.

It was amazing driving mom's old car. A small picture of her and dad hung from the rearview mirror. The picture was old, older than me, the colors were all faded by time, but I could still see the love they had between them. If I were a regular woman, I probably would have been put off by the picture of my boyfriend's dead wife hanging in his car, but since it was my mom, I was more than cool with the idea.

I drove directly to Nick's real estate office in the Town's Square. His dad founded the company back when we were kids, but Nick and his brother Peter took over after their father became sick with cancer. When he died, Nick took over as head of the company. I parked outside at a meter, then walked into the office with my tight fitting dress which showed every inch of my womanly physique. I could see the plump secretary's face frown slightly when I walked in (the normal reaction I get from jealous women who don't measure up). "May I help you...?" she asked, looking me over from head to toe as if I'd just tracked dog shit in on the carpet.

"I'm here to see Nickolas Cartwright!" I said, flipping my hair back dramatically.

"Is he expecting you...?" she asked, looking through the daily planner.

"Just tell him Alexandra Wilkinson is here to see him..., I guarantee he'll want to see me!" I answered, confidently.

The secretary tried not to look cross as she picked up the phone and dialed Nick's office. "Yes, mr Cartwright..., there's a woman here to see you. She said her name is Alexandra Wilkinson!" I watched as the secretary's face went stone. She looked up at me briefly, then quickly averted her eyes with embarrassment. I had to hold back my chuckle when she finally said, "Okay sir, right away." She hung up the phone and then said, "You may go right in, ma'am." without looking up.

I sashayed by her desk as I barged into Nick's office...

"Alex..., what a surprise...!" he glee, getting up from his father's old desk. "To what do I owe this visit...? Are you looking to sell your grandparents property...? I'm sure we could get a good price for it!"

"Can the small talk, Nicolas..." I said boldly, shutting the door behind me. "...we both know I'm not here for a social visit!"

"We both also know you're not settling any properties for any elderly or deceased grandparents either...!" added Nick, smugly.

"Then what AM I doing here in town...?" I asked, wanting to know how much he knew.

"Well that's the thousand dollar question...!" smiled Nick, standing directly in front of me. "At first I thought you were a gold digger, trying to swindle old man Wilcox out of his life's savings..." said Nick openly, not caring about hurting my feelings. "...but then I did some checking and discovered that other than some old outdated life insurance polices, old man Wilcox ain't worth too much of anything! And what he does own, is willed away to his faggot son Alex, --wherever he is!" I tried not to react to Nick's hateful description of me as I kept my face stony. "Which means either you have some other scheme going on..., or..."

"Or what...?" I asked curiously, as Nick's eyes slowly wandered down to my chest.

"...or..., you have some sick twisted unnatural attraction to old men!"

"Lester's not old..., he's older...!" I corrected.

"What do you see in a man old enough to be your father...?" asked Nick, twisting his face distastefully. "Did your father leave you as a kid...? Were you deprived of a father figure in your life...?"

"What business is it of yours...?" I asked, offended. "Why are you so concerned about what Lester and I do behind closed doors in the privacy of our bedroom...?"

"It's just sick!" said Nick, shivering as if to shake the idea out of his head. "You could definitely do much better!"

"ah..., and let me guess..., --YOU'RE the better...?!" I assumed.

"Is there any doubt...?" asked Nick, grinning broadly. "You could definitely do worse...!"

"Somehow, I doubt that!" I said, being purposely snobbish.

"Did I..., DO something to offend you...?" asked Nick, unexpectedly. "Ever since I first met you..., you've been acting as if I did something to you personally...! Have we met before that I'm unaware of...?"

"No..." I said, not wanting him to put two and two together. "...but I believe your WIFE might be interested in knowing why you're so concerned about Lester's and my relationship!"

"Oh..., THAT!" laughed Nick, guiltily.

"Right..., that!" I said confronting, fully expecting Nick to back down after reminding him that he was married.

"So..., you're not mad to ME per se..." he said, playing mind games with me. "...you're angry that I'm married...?"

"I didn't say that...!" I defended.

"You didn't have it..., it's implied!" he smiled, confidently. "Well..., my wife's not here now...!" he said, stepping up close to me. I looked down and noticed a prominent lump forming in his trousers. "See what you do to me...?" he asked, knowing I was looking. "You've got to be one of the hottest women to ever walk through Madison County..." he added, touching his hand against the bare skin of my neck. I felt my knees grow weak as memories of Nick Cartwright and his brother Peter butt fucking me front and back filled my head.

Memories of how they would take turns ramming their hard teenage cocks in my ass turned me on like nobody's business. I felt his hand slowly rub down my neck and across my breasts. He hooked his fingers into my cleavage and pulled down the front of my dress and bra, exposing my bare tits. "Beautiful..." was all he said before licking his lips, and bending forward to take one of my tits into his mouth.

My mind swooned as Nick Cartwright sucked my left titty. In all the years he and his brother used me as a sexual guide to fucking girls, he never used his mouth to give me pleasure, he never lifted a finger to make me feel good (other than fucking me or allowing me to suck his cock). I was amazed at how hungry his mouth was as it sucked my left nipple inside. His lips formed around the fatty skin as he suctioned inward, creating a vacuum with his mouth.

I moaned softly as Nick latched his mouth to my breasts, then used his hands to roam over my body and ass. He pulled me into him, grinding his crotch bulge into me as his hands tightened on my ass. I couldn't help grinding my cunt into him, wanting to feel his cock against me again after all these years.

Nick pulled the back of my dress up as his fingers pulled at my panties. I could feel them searching as they poked at my cunt lips and asshole. I gasped when he suddenly sank a finger into my cunt. A second later he pulled away and began unfastening his pants.

"Wha...what do you think you're doing, Nick...?" I asked breathlessly, my tits still hanging out of my dress.

"One good suck deserves another..." smiled Nick, reached his hand around the back of my neck as he gently guided me down to my knees in his office.

I must confess as a bonafied cocksucker, I was mesmerized by the bulge. I wondered if his cock still looked the same after all these years? I waited with bated breath as he unfastened, unzipped, then pulled his erect cock free. Sure as I remembered it, it popped out into the open, demanding service.

I stared at the cock for a few seconds, getting reacquainted when Nick pulled my head forward. His cock head touched my painted lips as I kissed the tip. I heard him moan as I began to lick it. I coated the head and shaft with my tongue and saliva before finally opening my mouth to let him in. It was like being taken back through a time machine. Suddenly I was 14 years old again, sucking Nick's cock in his parents' garage while they sat in the family room watching television.

My entire childhood from 11 to 15 was consumed with pleasing Nick and his brother. For years they dominated me, making me their own personal cocksucker to use and abuse when and wherever they wanted. I remembered times when they made me suck their cocks so much that my lips looked like they had been injected with collagen. I sucked their cocks in their bedroom during sleepovers and while we were supposed to be studying or playing video games. I sucked them off in their backyard treehouse, in their father's car, in the school's boy's bathroom and stairwells, I even blew Nick one day on the school bus (after he had told everyone about me). Suddenly I was in dejavu, sucking the cock that tormented me and gave me the greatest pleasure as a kid.

Nicolas knew nothing of my past (of course), as he held my head and fucked my face. I could feel his cock sliding easily (familiarly) between my lips. I think he was pleasantly surprised when he pressed his cock into my throat and was met with no protest, nor a gag reflex. I swallowed Nick's fat 8" cock all the way down to the balls as he groaned happily above me. I latched my hands around his clothed thighs and bobbed my head back and forth. I sucked feverishly on the head of his cock, making him squirm before pummeling my own throat down the shaft. I took his man meat from tip to base with every stroke, fucking my own face harder and faster than he ever did. I was no longer the skinny shy kid who sucked cock timidly under the bleachers during home games, --now I was an experienced woman who knew exactly what she wanted and how to get it.

"Geez..., you really know how to suck cock...!" gasped Nick, grabbing the edge of his desk for support as I went to work.

I bobbed back and forth like a sucking machine, devouring his entire cock to the very root. I could feel Nick starting to thrust into my mouth, meeting my downward suck with an upward thrust. Soon we were fucking with a steady pace, --his cock and my mouth. My lips slammed into his hairy pubes over and over as I gobbled down every inch of his rock hard manhood.

"Oh this is sweet...! You're the best cock sucker I've ever had...!" he moaned, lost in lust. That only inspired me to suck harder as I picked up the pace, wanting to taste his load. I went wild, sucking hungrily as I smeared my lipstick all along his cock shaft. Nickolas could barely keep his composure as I gobbled his manhood relentlessly. He grabbed my tits, squeezing them in his hands as he fucked my face. My hair flung back and forth messily, getting hung up on his cock and my wet lips. But that didn't stop me from swallowing his rod full length every time, feeling his cock pummel my throat.

I could feel Nick's legs starting to tremble as he got closer to cumming. I wanted his load so badly. I cupped his hairy balls in my hand and churned them around while I sucked. That sent him over the edge as he suddenly grabbed my hair (locking his fingers in the roots) and shoved his cock down my throat and came.

"Uhh...! Uhh...! Uhh! Aww fuck...! Yeah! Damn yeah! Oh god...! ARRHHH...!!" he grunted and groaned, trying to keep his voice down as he came down my throat.

I could feel his cock pulsating as it pumped and poured cum straight down into my stomach. My nose was buried in his pubes as my lips stretched around his cock base. When his fingers started to loosen in my hair, I knew he was finished cumming. I slowly drew my lips back up his cock shaft, gathering the last of his seed on my tongue before swallowing.

"How long are you going to be in town...?" asked Nick, recovering from his orgasm.

"I'm not sure..." I said, allowing his softening cock to fall from my mouth. "...it depends..."

"On what...?" he asked, helping me up off my knees.

"On..., what happens with me and Lester...!" I answered, honestly.

"You're not looking for him to fall in love, are you...?" he asked, his face frowning again.

"He's a good man. A nice man!" I argued.

"You don't want nice...!" he said, pulling me into his arms. "You want someone young, rough, and dangerous!"

"You're already taken, Nick...!" I reminded him, pushing him back.

"You can't deny there's something between us...!" argued Nick, as I pulled out my makeup kit and began to fix my face. My lipstick was everywhere! "I felt it the first time I saw you at the bar! There's some connection there...!"

If only he knew!

"You're married, Nick..., and I'm with Lester!" I said, snapping my mirror closed as I put away my kit and my tits. "Forget any of this happened...!" I warned, turning towards the door.

Nick put his cock away as he refastened his pants.

"When can I see you again...?" he asked as I reached for the doorknob.

"You can't!" I said.

"I still have to fuck you!" he stated boldly. "You can't leave town until I've fucked you...!"

"You already have a woman for that...!" I sniped.

"But I want yours!" he insisted.

"Do you always get what you want, Nick...?" I asked, coyly.

"Of course!" he smiled.

"So do I!" I laughed back, opening the door and accidently bumping into Nick's wife Donna! "oops...!" I said surprised, as she suddenly appeared in the doorway out of nowhere (I suddenly had flashes of Nick's secretary frantically phoning the misses, warning her of the beautiful blonde visiting her husband!). "Hi...!" I said, trying to act natural.

"Hello..." said Donna coldly, looking at me oddly, then at her husband.

"Honey...! What're YOU doing here...??!" he asked, trying not to sound suspicious. "This is an unexpected surprise!" he beamed, grinning hard. "uh..., Donna, this is Alexandra...uh..."

"Wilkinson!" I said, in case Nick didn't remember my fake last name.

"...Wilkinson...!" added Nick. "She's looking for an agent to settle some old properly of her grandparents...!"

"Really...?" asked Donna, sounding skeptical. "Are YOU from Madison...?" she asked, looking directly at me.

"No..." I answered, "...I wasn't very close to my grandparents..., I'm from California!"

Before Donna could rebuttal, I turned to Nick..., "I have your business card..., I'll call you once I decide what I want to do with the property...!"

"Do that!" said Nick, as I left the office as fast as my stiletto heels would take me.

I left Nick's office feeling hornier than ever. I had sucked the cock of the boy that had turned my entire life around from the very beginning, and nearly got caught by his wife. Lord knows what Donna was saying to him right now behind closed doors? I wondered if she was sniffing him for my perfume? Or if she was checking his cock for my lipstick?

I reached my hand down between my legs as I drove, rubbing my pussy through my panties as I imaged Nick fucking me. I remember how his cock felt in my ass as a teenager, how he used to hold me down and butt fuck me until he came off inside me, then would switch off with his brother, or one of their friends. My asshole started to pucker hungrily as I drove. I needed cock in me, and I needed it quickly. I decided to head over to dad's job for a mid-morning quickie. I know he was something of an old fuddy-duddy, but I was sure I could get him to fuck me if I could get him alone! With my mind made up, I headed for his work. I made a right turn on a red light, and was instantly met with the flashing lights of the Sheriff behind me in my rearview mirror...

To be continued...

___________________________ Written by Eugene Marvin aka NPhillydogg@aol.com Or hit me up on Facebook for updates of my stories.

Next: Chapter 7


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