Bridging the Gap

By NPhillyDogg/Scedmark

Published on Aug 21, 2009

Transgender

Dad waited for me patiently as I removed my makeup, cleaned my face, exfoliated, lotion and moisturized, reapplied foundation, lip liner, lipstick, eye liner, and blush, AND washed my hair with a 5 minute sitting foam which instantly curled my long luscious blonde hair and gave it that rich warm glow.

I fully expected dad to hit the roof after waiting for me in the bathroom for so long, but as I slowly descended the stairs in my tight form fitting sundress with the plunging neck line, my stiletto heels and my long curly dirty girl blonde hair cascading down around my bare shoulders, he merely smiled, adjusted his hardening cock and said "wow..., now that's worth the wait!"

I blushed as he opened the door for me like a gentlemen, a far cry from the abrasive asshole whom kicked me out of the house as a teenaged boy. We drove in dad's car out to the motor Inn Motel on rt319, where I had checked in the day before. He walked me into my room as I started to run around to pack up my scattered clothes, lotions, and girly things I had lying around and stuff them in my two heavy suit cases. Dad walked around the room, examining things as if he was an inspector of some sort. I suppose he was curious about this woman he'd just met the day before, whom he'd already fucked 3 times and had asked to move in with him without knowing a single thing about her.

He packed my bags into the trunk of his car as I went into the motel office to settle the bill with the money dad gave me to pay the bill. "You hungry...?" asked dad as I came out of the rental office. "...I know a really good diner in town were we could get a late breakfast..., or lunch...!" he said, looking at his watch.

"Either sounds good to me, Lester...!" I smiled as he opened the car door for me, making me feel like a lady.

We drove through town. I had to act as if I were seeing many of the landmarks as if for the first time as dad pointed out everything of significance. There was the General Store where I worked as a teenager, bagging groceries and stocking shelves during the summers off from school before getting fucked in the back office by the store's manager. There was the high school I used to attend, sucking teen cock in the boy's restrooms. And there was the cemetery where mom was buried. Dad and I used to go there on her birthdays and at Christmas to leave fresh cut flowers on her grave. "Where's this diner...? I'm ready to eat!" I said, taking my mind off my past.

Mel's Diner was a staple in the community since before I was born. Its just about the only restaurant dad ever took me to as a kid. We used to eat breakfast, lunch, and dinner here (until I learned how to cook). As soon as we walked into the diner (the welcoming bell overtop the door signaling our entrance), everybody in the place seemed to turn and stare at us at once. "Morning Lester...!" smiled a middle-aged red headed waitress as she grabbed a wet rag off her hip and wiped up a clean spot for dad at the counter. "...want your usual...?" she asked, grinning at him as if he he'd just offered to double her lousy paycheck.

"uh...Susanne..., I have a friend with me today...! We'll take a booth!" he said, putting his arm around my waist.

"Oh..." said the waitress, her smile dropping like it weighted a ton. I saw her cut her eyes over at me as she grabbed up two menus and showed us to an available booth by the window. Dad may not have noticed her sudden cold demeanor (as he helped me into the booth), but I did. "Do you know what you want...?" she asked coldly, the warm demeanor she had when we came in suddenly out the window.

"uh..., I do..." said dad, settling in next to me. "...but I think the lady will need a minute or two to look through the choices." he added, handing me my menu.

"Fine!" said the waitress, walking off.

"What's her problem...?" I asked, opening the menu. "She acted like she had a bug up her ass! You two dating or something...?" I inquired.

"Me and Susie...?" he asked, looking at her as she walked back behind the counter in her pink waitress uniform and sensible shoes. "No...! We're just friends...!" he said.

"Friends with benefits...?" I asked, unsure.

"No..., just friends!" laughed dad. "Susie's been a waitress here for like the past 12 years! She knows me, is all!"

"hmmm..., from the way she rolled her eyes at me..., I'd say she wants to be more than just friends!" I surmised.

"Susie...?" asked dad, doubtful. "...I doubt it!"

"Take my word for it, Lester..., a woman knows when another woman's interested in her ma...!" I caught myself before I said it.

"In her what...?" asked dad, smiling.

"Nothing." I said, looking through my menu.

"No, tell me...! Interested in her what...?" he asked again, probing. "You were gonna say MAN, wasn't you? You were gonna say `a woman knows when another woman's interested in her man!' Admit it!"

"I don't know what you're talking about...!" I said, keeping my nose in the menu.

"Here's your coffee, Lester..., just the way you like it...!" said Susie, bringing dad a hot cup of black coffee without being asked.

"Thanks Susie!" smiled dad, flirting with that bitch.

"You want your usual...?" she asked, putting her hand on his shoulder.

"You know me, Sue...!" he said with a chuckle.

Susie joined him with a flirtatious chuckle of her own before ripping her order pad from her hip and flipping the top back to a fresh page.

"You ready to order, hon'?" she asked me, in a very crude cut and dry tone.

"I'll have..." I said, pausing as she poised with her pen. "...what he's having!" I said, folding up the menu.

"Are you sure...?" she asked, skeptically.

"You know me, Susie...!" I smiled, repeating what dad said.

Susie snatched up the menus and hauled her ass off into the kitchen as if I'd just slapped her across the face. "See..., I told you she's interested in you!" I said, as soon as Susie left the table.

"I don't see it!" said dad, naively.

"Of course you don't..., you're flirting right with her!" I said, busting him.

"No I'm not...!" defended dad.

"Oh what was that corny chuckle when you said `you know me Susie...ha-ha-ha!' She had her hand on your shoulder! Since when does she need to touch you to get your order?" I asked.

"You sound jealous...!" smiled dad.

"Jealous...?" I asked, frowning my face. "That lady's twice my age...!"

"She's 38!" corrected dad. "She's a divorced mother with two teenage boys her husband was granted custody of...!"

"So...? What does THAT got to do with anything...?!" I asked, flipped.

"She knows what it feels like to lose a child..." said dad, sadly, looking down into his black coffee.

"oh..." was all I said, grabbing the back of his hand in support. Dad grabbed my hand with his other hand, rubbing my smooth soft skin back and forth. He really did miss me. I mean his son...(me), Alex.

"Have you..., uh..." I started, unsure if I really wanted to travel down this road...? "...have you tried, finding him...?"

"No..." said dad, looking lost in thought. "...I figured if he wanted to come home, he would have done it by now...! It's been like 10 years! I'm sure he's happy somewhere being who he wants to be!"

"You'd let him come home if he wanted to...?" I asked, my heart racing a mile a minute after posing the question I'd been wondering for so many years...!

"He's my son..., my only child! Of course I'd let him come back home if he wanted to...!" said dad, looking at me with sincerity in his eyes and voice.

"What if nothing's changed...? What if he's as gay or gayer than he was before he left...?" I asked, wanting to know the truth.

"I wasn't happy to learn that my son was gay..." admitted dad, "...but if I could go back and do things differently, I would! I'd sit him down and try to get him to understand that all I wanted was the best for him! For him to live a normal life, get married, have kids, and continue the family name...! But if that wasn't possible..., I'd tell him that none of that mattered, so long as he was happy!"

"If he knew that..., I'm sure he'd come home...!" I said, fighting the swelling tears in my eyes.

"You think so...?" asked dad, looking up at me as I tried to shield my face. "Are you...crying, Alexandra...?" he asked, as I dotted my eyes with a napkin.

"I can't help it..., that was the sweetest thing I ever heard a father say about his son...!" I answered, covering my sentiment.

"Thanks..., for all the good it does me..." said dad. "...it's not like Alex'll ever hear me say it!"

"Oh..., I think he'll feel it, no matter where he is...!" I answered, touching dad's hand thigh.

Dad smiled at me before leaning over to kiss me. Our lips touched as he slowly snaked his hand around my neck, holding my head steady as what started off as a simple kiss for gratitude suddenly turned heated and sensual. I reached down between his legs and felt his soft cock bulge, rubbing it back and forth until it started to fatten and thicken in his crotch.

"ummm..." interrupted Susie, holding two big hefty plates in her hands.

"Oh..., sorry..." smiled dad, wiping my smeared lipstick from his mouth as Susie sat our plates down before us. My plate hit the table so hard that some of my fried potatoes fell off the side.

"Here you go..." she said, sliding a huge plate of stacked pancakes with blueberry topping, scrambled eggs, sausage, bacon, home fries, biscuits, and grits! "...two hungry man specials!" she smiled, giving me that `I gotcha now, bitch' grin as she placed her hands on her hips and said..., "Enjoy!" before walking away with a smirk.

Bitch!

Pt-2

"I can't believe you ate ALL of that...!" said dad, as we went back to the bar we first met at for an afternoon drink. "Ive never seen a woman put away that much food in one setting! You must have your daddy's genes!" he said, causing me to choke on my drink. "You okay, baby...?!" he asked, patting me gently on the back as I cleared my windpipe.

"I worked up quite an appetite what with all the hot sex I've been having lately!" I joked, once I regained my composure.

Dad blushed as he excused himself to use the men's room. While I sat at the bar alone (enjoying my drink), I saw a familiar face I recognized as a kid. Nicolas Cartwight walked up to the bar, ordering drinks for him and his lady friend. Nick was one of the main boys that took advantage of me when I was a kid. He and his brother Peter would force me to suck their cocks during sleep overs at their house. They weren't exactly good friends of mine, and would only invite me over so they could fuck me. In fact Nick was the first guy to take my virginity, sliding his big dick up my ass in the middle of the night as we shared a bed and his brother lay sleeping across from us in the same room.

Nick's eyes met mine after he gave the bartender his order. I quickly turned away, not wanting to wrist talking to someone who knew me back then.

"Hi..." he said, walking up behind me as I slowly turned around. "...I couldn't help but notice you sitting here alone...!" he said, smiling seductively as he stared openly at my bosom. "Can I buy you a drink...?"

"I believe you just bought a drink..." I said, playing it cool. "...for HER!" I added, nodding towards the brunette sitting at a table giving me evil eyes.

"That's my sister!" he lied.

"Sister...?" I asked, recalling Nick and Peter had no sisters.

"My name's Nick Cartwright..." he introduced himself, holding out his hand to shake. "...and you are...?"

"On a date!" I said, ignoring his hand as I continued to sip my drink.

Nicolas was always the pretty boy jock in school, all the girls wanted him, all the boys wanted to be his friend (including me). Later I found out that Nick only befriended me because he and his brother knew I was gay. They would make me suck their cocks just to be their friend. If I said I couldn't or didn't want to, they would refuse to be my friends and threaten to tell everyone that I was a cock sucker. All through junior high I sucked their cocks whenever and wherever they wanted. On weekends (if dad didn't have plans for me) I'd spend the night at their house supposedly to play video games, but as soon as their parents went up to bed, I spent the rest of the night with my face buried in his and his brother's crotches, sucking cock til they finally fell asleep.

Eventually they did end up telling some of their friends about me, making me suck them off as well. By age 14 I was blowing at least 30 guys weekly in school, giving group blowjobs after school and at parties. That is, until dad found out and hit the roof...

"You're on a date...?" he asked, skeptically. "I don't see anyone...!" he asked, looking around. Mocking me.

"He's in the men's room!" I said, snobbishly.

"Only guy I see coming out of the men's room is old mister Wilcox!" said Nick, looking shocked when dad walked over to me and slipped his arm about my waist.

"Nicolas..." said dad, holding out his free hand to shake. "...it's been awhile! How's your father...?"

"uh..., not so good mr Wilcox..., he'll be starting on dialysis shortly...!" said Nick, flabbergasted.

"Nick's father has cancer..." explained dad.

"Oh..., I'm sorry to hear that." I said.

"Oh, Nick..., this is Alexandra..., she's a friend of mine that will be staying with me for awhile...!" introduced dad. "Alex..., this is Nick, one of my son's friends from high school!"

"Hi...!" I said, shaking Nick's hand.

"Alex, eh...?" asked Nick, making me nervous. "I didn't know you had a daughter, mr Wilcox...! You've been holding out on me!" he laughed, making fun of our dating.

"I'm not his daughter...!" I said, putting my arms around dad's waist.

"Alex is in town to finish up on some paperwork on her grandparents' house...!" explained dad.

"Really...?" asked Nick, sounding far too interested. "Are you buying or selling...?"

"Oh yeah, I forgot..., YOU and your brother Peter took over your father's real estate company...!" recalled dad

(uh-oh).

"Yeah..." said Nick, reaching into his wallet to pay for his drinks as he pulled out a business card. "...if you tell me who you're working with..., I might be able to help swing you a good deal...!"

"Oh..., I'm okay, thanks! Everything will be finalized on Monday!" I lied.

"Monday...?" asked dad, surprised. "I thought you didn't know how long you would be in town for...?"

"Well..., the paperwork will be finalized on Monday..., but I still have to put my grandparents' furniture into storage, and figure out what to sell and keep...!" I adlibbed.

"I'm sure Joanna would be able to buy most of the stuff your grandparents have to sell..." suggested dad, being helpful. "...she runs a used furniture value store down in the Square...! I'm sure you could unload most of the items on her!"

"Oh, okay..., I'll think about it..." I said.

These lies were getting too deep.

"Okay, well..." said Nick, taking heed of the evil looks coming from his table. "...you have my card! Call me if you think I could be of help!"

"Do I need to be concerned...?" asked dad, taking his seat at the bar after Nick left.

"About what...?" I asked.

"The younger man...!" said dad, coyly. "I saw the way Nick was looking at you when I came out of the men's room..., he looked like the cat about to swallow the canary...!"

"Nick is nothing...!" I assured dad. "He's just a dumb jock with a business card! I got all I need right here...!" I said, wrapping my arms around dad's as I lay my head on his shoulder.

"Good..., then what's say we get out of here and go home...?" propositioned dad.

"Sounds good to me!" I said, leaving the drinks behind.

Dad took my bags into the house, then made room in his closet for me to hang up some of the dresses and blouse I bought with me. I had no idea how long my little plan (to seduce dad and break his heart) would take when I got here, but (being the stylish girl I am) I bought enough clothes to mix and match for a month.

Dad ordered food from some take out place he often used, then we sat back on the sofa (with me cuddled in dad's arms) and watched some of his favorite old movies: Psycho, The Birds, and The Godfather. During the Godfather I got so horny with dad absentmindedly playing and pinching my erect nipples with his hand down my blouse, that I pulled his cock out of his pants and started sucking it for him. Dad looked surprised, but welcomed the gesture as he laid back relaxing on the sofa while I lovingly sucked his cock gently. During the entire movie I kept him on the verge of cumming without allowing him to go over. By the end of the movie I had reached into my bag for my lubricant, moistened my cunt and his cock, then sled down on it until it filled me up completely.

"I couldn't wait any longer...!" I said as I bottomed down against his balls and ground myself in his lap.

"You know..., I've never met a girl like you before..." whispered dad, wrapping his hands around my ass as he started to squeeze my soft cheeks.

"Is that good or bad...?" I asked, bouncing on his cock slowly as we gazed into each other's eyes.

"Definitely good...!" smiled dad. "I could easily fall for a girl like you...!"

"Cool..." I said, having snagged the man I wanted. "...cause I could definitely fall for a man like you too...!"

Dad reached up under my hair and pulled my head down to his face to kiss me. I could feel the strength in his grasp as he pressed his lips firly against mine, his tongue sliding into my open mouth. I sucked on his tongue as I rode his cock, feeling him slip and slide through my man made vagina.

Breaking the kiss dad started to unbutton my blouse as my Victoria's Secrets caught his eye. The bra I wore unclipped from the front for easy access. Dad unhooked it, allowing my breasts to spill out before him. He took both breasts in his hands and massaged them firmly, twisting and turning them as he sucked each nipple into his mouth. "Ooh daddy...!" I moaned, leaning back as I bounced on his cock harder. With all the men I'd been with over the years, this was the one I wanted most. All of my sexual fantasies surrounded my father, him taking my ass or my pussy as his own, making me his official cum dump slave.

Dad pulled me gently up off his lap until his cock slipped from my warm cunt. It remained hard and stiff, shinning with lubricant as he positioned me onto my back. "Wait daddy...!" I said, reaching for the lube as he pulled off the rest of his clothes. I poured a generous amount into my manicured hand, then smeared it all over my hairless asshole. As preparation I shoved two fingers inside to loosen me up, Dad knew what I wanted as he waited patiently for me to give it to him.

Removing my fingers I lay back flat on the sofa, raising my legs to give him a better target into my asshole. Dad aligned his cock with my beautiful rosebud, then slowly sank his thick 8" cock into me.

"Ooohhh yeeessss dadddyyyy..., fuck my asshole...!" I moaned as he pressed his hairy pelvis into my ass, indicating that he had all 8 inches successfully sheathed inside me.

"Oh you're so horny..., I've never known a girl who likes it in the ass as much as you...!" laughed daddy, settling down on top of me as he started to thrust himself in and out of me.

Now with his cock in my ass-pussy, I could achieve the proper orgasm. I pulled my legs up high, elevating my buttock as dad thrust it cock through me with long steady strokes. In this position it was like being fucked in my vagina, but my ass was getting all the action. Dad kissed me on the lips as he continued fucking me, his huge hands squeezing my ass and holding the cheeks open and he pumped his way through them.

Almost immediately I could feel my first anal orgasm coming. My body began to tremble and shake as my anus started to spasm around his plunging cock. Dad never stopped stroking for a second as he plowed me straight throw my climax and kept fucking me.

I felt so weak and helpless underneath him, unable to defend myself as he used my body for his pleasure. After cumming I simply wrapped my arms around his broad back and let him ride me til his heart's content. Dad began to perspire the longer he fucked me. I could feel his cock started to swell brick hard inside of me as his thrust got more frantic. I panted breathlessly in his ear as he suckled my bare neck. With a yelp I felt dad's cock pulsate, then start shooting thick loads of heavy cream inside me.

As dad's cock continued to pour cum into me, I couldn't help but feel my love for him grow all over again. Dad lifted his head as he kept his cock well planted in my boy-cunt, --and kissed me gently on the lips, slipping his tongue delicately into my mouth. I sucked on his oral taster as he finished of inside of me. And for the first time since I was 15, I felt at home!

Next: Chapter 5


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