Bridging the Gap

By NPhillyDogg/Scedmark

Published on Jun 5, 2010

Transgender

BRIDGING THE GAP-8

Deputy Mackie dropped me back off by my mom's car, then said goodbye awkwardly before driving away. I understood his weirdness towards me (being that he was engaged and we had just fucked for the first time in a jail cell), and didn't really take it personally. I still wanted to see him again, and hoped I'd get another chance with his cock before I finally left town (probably in disgrace).

I got back home, showered, dressed, and got dinner started long before dad got home from work. He was a bit tired after a long day of standing on his feet, but he was in good spirits and feeling a little rambunctious. As soon as he got home I sat him down in his favorite chair, got him a beer, unbuckled his pants, then gave him the best blow job of his life. Dad lay with his head against the recliner, moaning and groaning in heat as I worked my mouth up and down his rigid cock with expert precision. I swallowed his cock down to the balls, churning it around in my open throat before slurping my way back towards the head. After about 10 minutes of uninterrupted oral massage, dad finally burst forth in my mouth, flooding my oral cavity with his creaminess.

"AARRRHHH...!!" he groaned as he came, pumping my mouth full of the cum that created me. I swallowed my brothers and sisters, then quietly got up and went back into the kitchen to finish cooking dinner.

Dad walked in behind me, staring at me from the door...

"What...?" I asked, looking over at him innocently.

"Where did you come from...?" he asked with a grin as he folded his arms across his wife beater and stared at me.

"I TOLD you..., California...!" I said, playing dumb.

"I know..." responded dad, his uniform pants undone around his waist. "...that's not what I meant...! I mean..., why aren't you married with a house full of children...? Any man would be happy to have you! I find it hard to believe that someone this beautiful and sexually gifted as you, is still walking around unspoken for...!"

"Well..., maybe that's because the right man's never asked for my hand...!" I said coyly.

Before dad could rebuttal, we heard the doorbell ring. Dad looked a little annoyed as he zipped his pants and headed for the door...

"Lester...!" said Susanne (the waitress from the diner), "How ARE you...? I came over as SOON as I heard!"

"Heard what...?" asked dad, standing in shock.

"Of Alex's arrest, of course...! Haven't you heard...?!" asked the aging woman, trying desperately to hide her wrinkles behind bad makeup!

"Arrest...?" said dad, confused. "I don't understand...!"

"Margret Bushwater told Gail Sheerwood who told Wilma Sidebottom that she saw the Sheriff arresting her this afternoon for stealing your wife's car! It's all over the county!"

"What...?" asked dad, completely lost.

"I know!" said Suzy. "I KNEW she was up to something..., but I never would have guessed it was to steal an old 30 year old car! I'm so glad she's out of your life! You're much better off without her walking around town flaunting her big perky breasts...! I bet their not even real anyway! They set up too high and unmoving..., it ain't natural!" laughed Suzy motor-mouth. I loved the shit faced expression on her weather beaten face when I stepped in from the kitchen. Her jaw dropped, her eyeballs popped, and all the painted color flushed from her pale vampire like face...

"Hello Suzy...!" I said, wiping my hands on a dishtowel. "What brings YOU by...?"

"Alex...!" she cried, spooked out of her wits. Obviously whoever her informants were, neglected to tell her that I was paroled after only 90 minutes of jail time. "I uh..., I, uh..., I..."

"Susanne..., I don't know who your sources are..., but I LEANT Alex that car...!" defended daddy, coming to my honor as I walked over and wrapped my arms about his 38" waist. "She needed to run some errands today while I was at work, and I didn't want her having to catch taxies all over town...!"

"But..., but..., you NEVER let anyone drive your wife's car...!" said Susanne, looking as if someone had just slapped her straight across his Crept Keeper's face!

It was priceless!

"Well..." said dad, placing his arm around my shoulders protectively (Suzy could have shit bricks). "...Alex is more than just ANYone...!" he added, smiling down at me warmly. I couldn't resist leaning upward to steal a kiss. Suzy cringed at the display of affection. "Oh..." said dad, breaking the kiss when he remembered Suzy was still standing there. "...would you like to stay for dinner...? Alex is cooking...!"

"No..." said Suzy (wisely), hating the way we flaunted our feelings in front of her (I could see it all in her face). "...I have to get back to work..., I'm only on break..., doing a double shift tonight!" she said with a nervous grin.

"Some other time, maybe...?" asked dad, totally unaware of Suzy's feelings for him.

"Yeah..., maybe..." said Suzy, walking away as fast as her stumpy little legs could carry her.

"Bye Susanne...!" I said sarcastically, closing the door behind her.

When I turned around, I pulled dad into my arms and kissed him again, thanking him for coming to my rescue. We ate dinner, then retired on the sofa to watch old movies. Dad ignored phone calls from other nosey neighbors who thought I was in jail, and trying to rip him off. We went to bed around 11pm, after taking fresh showers. Dad came into the bedroom with his soft cock resting between his legs. I had oiled and lubed my cunt while he was in the bathroom, getting it moist and delicious for him in case he wanted sex.

"You know..., all of the guys at work praised me today..., saying that I had the hottest girl in town!"

"aww..., that's sweet!" I said, knowing all of them would love to be in his shoes.

"They wonder what a beautiful young girl like you would want from an old man like me...?" he asked, climbing into the bed.

I pulled the covers back, holding my arms open as he closed in on top of me. I parted my legs, allowing him to nestle his body in-between as we pulled the covers back up over us.

"You tell those guys at work..., that this young hot girl is just completely crazy for you and that big hard cock between your legs!" I said, kissing his stubble chin.

"Is THAT why you're with me...?" asked dad, pulling back. "You're only interested in my body...?" he joked, kissing me back.

I could feel his cock starting to grow between my legs, the plump shaft getting fatter and fatter as it swelled with blood. I reached down and maneuvered myself under him, getting his hips directly aligned as I aimed his hardon up to my cave pit. Dad sank in slowly, taking his time to feed my cunt his staff. My eyes bulged slightly as he filled me, his big cock moving straight into me swiftly as he settled in on top of me and began to kiss me again. I loved having his weight on top of me, weighing me down into the mattress as he fucked me.

Dad slowly slid his cock back and forth through me, taking his time to open me up and allow my body to adjust to his dick. His tongue dug into my mouth like a small animal burrowing into a hole. I suckled his wet tongue, loving the taste of it as his hairy chest scratched against my tits.

We made love for nearly 45 minutes, with his body becoming sweaty as he came off inside him, bathing my insides with his male essence. I loved hearing him groan when he came, his big dick pulsating inside me as it pumped me full seed. We slept the night away in each other's arms, dad cuddled up behind me in spoon position as he cupped my right tit in his hand like a love handle.

The next morning dad was up and showered before I woke up. I had wanted to make him breakfast, but had been completely puckered out after all the wild sex I'd had with Nick, Mackie, the Sherriff, and dad. When I finally woke up, dad was fully dressed in his guard's uniform and ready to leave. "Don't worry about me, honey..." he said, kissing me gently on the forehead as he fumbled with his tie. "...I'll pick something up at the diner on my way in to work!"

The diner...' –I thought, still groggy. ...where THAT BITCH works?'

By the time I dragged my ass out of bed, dad was gone. I could just picture Suzy giving him the google-eye while he ate his flapjacks! I walked into the bathroom where I got a good look at myself in the mirror. I examined my face, making sure that all the old manly flaws of my former face were completely camouflaged. The last thing I needed dad to see were remnants of the face of his long lost son lying next to him when he woke up in the morning.

I took my morning pee, took my hormone injections (which I always carried in my travel case under lock and key), then jumped in the shower for a nice long scrub. I had to make sure to douche out all the semen that had been shot into me the night before by daddy and Deputy Mackie, as my body had no real way of absorbing the slimy liquid as a real woman's vagina might. After the shower, I lotion down with my special creams, then began the daunting task of applying my makeup. It was usually the first rule of thumb in transformation, --`learn how to apply makeup flawlessly!' A real woman could always be mistaken as a man so long as she had the right credentials between her legs..., but the real trick was to be a man who passed believably as a woman in what was essentially known as a man's world. If one could do that successfully, he practically had a ticket to ride! It was sometimes embarrassing how stupid men get in front of a pretty lady, thinking more with their dicks instead of their brains. I was just about finished with my makeup when I heard the telephone ring. Believing it might be dad, I reached for it...

"Hello sexy...!" said the voice of Nicolas Cartwright in his usual cocky tone. I could practically hear him smirking at me over the phone.

"How did you get this number...?" I asked, suspiciously.

"Are you kidding...?" he asked with a chuckle. "This is a small town..., everyone has everyone's number around here! Besides..., I used to be friends with mister Wilcox's son Alex...!"

"Really...?" I asked, skeptically. "Somehow I find it hard to believe you could truly be friends with anyone...!"

"Well..., friends might be too strong a word...!" recanted Nick. "We were more like..., arranged friends!"

"Arranged...?" I asked, curiously. "What kind of arrangement did you have...?" I inquired.

Nicolas chuckled...

"Well..., Alex was gay..., and would do just about anything to be my friend..." he confessed, thinking Alex (the girl) might find his story fascinating.

"Really...?" I asked, trying to sound amused. "What did you make him do...?"

"I didn't MAKE HIM do anything...!" defended Nick. "...but he would..., suck my dick just to hang around me...!" he laughed, making a cold chill run up my spine. "He was wimpy kid who clung to me like a lost puppy! I knew he was gay just by the way he used to look at me..., like he could picture me naked or something...!"

Instantly memories of me ogling Nicolas on the football field during practice came to mind, watching him score touchdowns and throw passes and wishing I could be something more than a friend. I remember the first time I tasted his cock, sucking it until he flooded mouth with its first taste of sperm. I was hooked from the moment I felt his cock pulse in my mouth, pumping me full of fresh spool.

"And so you took advantage of his infatuation...?" I asked, feeling betrayed.

"Believe me, as the town's queer he LOVED it!" assured Nick, confidently.

"But you let him suck it..., so what does that make YOU?" I asked, knowing the challenge to his manhood would get under his skin.

"Hey, I was 15 and getting my cock sucked royally...! Do you know how many teenage boys would kill for that...?" he defended. "It was hard finding girls who put out at that age back then...? But once I started dating girls, I dumped him...!"

"So you USED him...?" I stated angrily, the memories flooding back as if it all happened just yesterday. "You let him suck you and your friends off until you didn't need him anymore! You're a PIG, Nick!"

"You didn't think so yesterday when YOU were on your knees in my office doing the same thing!" countered Nick

"I'm a girl..., I'm SUPPOSED to like it!" I argued.

"You sure are...!" he said over the phone. "What are you wearing...?"

"Winter clothes and a wool coat!" I lied, standing in my bra and panties.

"Lair!" he said. "What if I told you I wanted to see you again...?"

"I'm with Lester, remember?" I reminded him.

"Yeah, and I'm married..., so what...?" he asked, shooting me down. "Is he home...?"

"Yes!" I lied.

"No he isn't..." he said correctly. "...his car's not in the driveway...!"

"uh...? So what're you doing..., SPYING on me...?!" I asked, rushing to the window. Peering through the mini-blinds, I could see a strange car parked across the street, the own sitting inside on a cell phone.. "Are you stalking me...?!"

"I want to finish what we started yesterday!" he said getting out of the car, his cell phone pressed to his ear. "If you think you're gonna get away with just sucking my cock..., you're sadly mistaken...!" he added, walking up the driveway.

I ran across the room to finish getting madeup...

"I'm not letting you in...!" I said, applying my smear proof lipstick.

"Don't worry..., I know how to get in..." he said, hanging up.

At first I didn't understand what he meant, then I remembered how he used to climb up the ivy along the outside wall of the house to sneak into my room late at night when he wanted some ass. I had barely gotten into my silk housecoat when I heard the sound of something falling over in my old bedroom. My heart was pounding a mile a minute as I stood in the doorway looking down the hall. I heard the sound of a lamp crashing to the ground, then saw the doorknob turn as Nick stepped out into the hallway. "Not as easy as it was when I was 15...!" he said, starting towards me.

"Stay where you are...!" I warned, stepping backwards as my robe fell open to reveal my perfectly scupltured body and pricy Victoria's Secrets underwear.

I could see Nick starting to foam at the mouth as he stared at my gorgeous body. "If you touch me, I'll scream...!"

"I plan on making you scream!" he informed, stepping into the bedroom while I stumbled backwards onto the bed. I watched as Nicolas (my childhood crush) started to undo his tie. "Tell me you don't want me..." he said, tossing the tie to the floor as he stared me knowingly in my eyes. I could see him looking through my soul! "...tell me to get out, and I will...! I'll turn around and take my hard cock back to work...! Is that what you want...?"

"What about your wife...?" I panted breathlessly as he began to unfasten his belt and trousers. "I'm sure she doesn't like sharing...!"

"Who does...?" he asked, letting his trousers drop to the floor. I could see his hardon pressing out the front of his boxer shorts. I subconsciously licked my lips, already imagining his cock in my mouth. "You look hungry..." he said, pulling his cock from the underwear slit. "...why don't you come over and get a taste...?"

Mesmerized, I got up to walk over to him when he suddenly stopped me in my tracks. "No..." he said, firmly. "...crawl..., on your knees!"

Flashing back to my childhood, I got down onto my knees and crawled over to Nick's stiff standing cock with absolutely no will power of my own. He stood there watching me smugly as I crawled over to him, then stretched my painted lips to take in his gorgeous cock. But just as I was about to envelop it, Nick pulled his cock away.

"What's the magic words...?" he asked, looking down at me.

"Please..." I begged, alternating staring at his cock and staring up into his cruel eyes.

"BEG for it!" I ordered, flexing it as it bobbed up and down before me.

I couldn't believe it. Here I was a beautiful woman (perhaps the prettiest girl in town), and here I am allowing Nick Cartwright to treat me as if I was still a skinny pimple face fag sniffing around his jock strap in the school lockers hoping to get a glimpse at his dick!

"Pleeeesssseeee..., can I have it...?" I asked, pouting sexily.

"Why...?" he asked, keeping his cock away from me. I could see pre-cum already starting to form at the tip, indicating that he was as excited as me.

"Because I'm a dirty little cocksucker...!" I said with a sad face.

Nicolas smiled, then offered me his cock by aiming it down at my face. I took it between my lips graciously, suckling the cum droplet from the head.

"That's a good girl..." he said as I savored the flavor of his pre-cum. "...suck my cock for me..., make it good and hard so I can shove it in that pretty pink pussy of yours...!"

I blushed as I took more of his cock into my mouth. I bobbed my head back and forth, dragging my lips up and down the length before taking it into my throat. "awww you're such a good cock sucker...!" he sighed, grabbing two fistfuls of my hair as he pressed my nose down into his pubic hair. I could feel his cock lodged in my throat as it ballooned outward to accommodate his girth. Nick head me there for several seconds before relaxing his hold and allowing me to back off. I slowly dragged my lips back up to the head, then sucked feverishly about the head.

"Enough of this shit..." he said, pulling me up off the floor as he threw me back onto the bed. With my robe open, my legs instinctively parted as he dropped to his knees. Pulling the sill of my panties aside to exposed my vaginal lips, he buried his face into my snatch then began licking me, tasting my manmade cunt for the first time.

"Oh god..." I groaned to myself as he ate me alive. Just the idea of Nicolas Cartwright's mouth on me (pleasuring me), was enough to make me have an anal orgasm. My legs shook uncontrolably as I came, my body stiffening and reacting to an orgasm I could no longer physically produce.

I looked down to see Nick looking up at me, half of his face buried under the mound of well trimmed pubic hair. He stared up at me while he ate, watching my every move as he reached up and pinched and pull my fully erect nipples. I was in heaven watching Nick Cartwright eat my cunt. All during our teen years I had been the one servicing him, the one on my knees using my mouth and ass to pleasure HIM. Now (finally) it was HIS turn to please me, and his talented tongue and mouth was doing just that!

Nick obviously liked eating pussy. He sucked and chewed on my vaginal lips until he had it dripping slick saliva inside and out, then he climbed up on top of me and poised his big 8" cock up to my cunt and looked down at me. "I've been waiting for this moment ever since I first saw you walk into that bar...!" he said, pressing his cock into me. I bit my lower lip as his cock slipped in, sinking all the way up to his hairy balls.

Nick ground his pelvis into me as he ground his cock around in my cunt, basking in the hot silkiness of my vagina. I spread my legs wider to give him better access. Nicolas laid down completely on top of me, resting his bare chest against my breasts as he began kissing me and sucking the crook of my neck. I could feel his cock moving through me as he began humping, fucking through me hard and rough as if he was already late for work, his tongue buried deep in my mouth. I was french kissing Nicolas Cartwright, the boy I had confessed to love so many years ago!

For nearly 10 minutes Nicolas fucked me, burying his cock again and again as he pumped his way through my vagina with increasing roughness. I panted aloud breathlessly, as most men like to hear girls moan. Nick was no exception as he alternated watching me, watching my tits bounce back and forth, and watching his cock disappear up my snatch.

I felt every jab, stab, and thrust as he fucked my cunt with deep hard repetitive strokes. Over and over he banged me, juicing my cup with his pre-cum. Occasionally he would pull out, just to make me suck his cock for awhile before shoving it back inside me. The more he fucked me the more I wanted to feel him explode in my man cunt. After all the money I invested on my sex change, I still got more fulfillment from having my asshole screwed. The last time Nick pulled his cock out of me, I begged him to fuck my ass.

"You want me to fuck you in the ass...?" he questioned, looking at me genuinely surprised. "You really ARE a freak, eh...?!" he laughed, motioning for me to roll over onto my stomach. "I've always wanted to fuck a girl in the ass..." he admitted, as he laid on top of me and rubbed the length of his cock up and down the valley of my ass crack. "...but no girl would ever let me...!"

"I will!" I offered, lifting my buttock invitingly.

Nick removed his cock, parted my ass cheeks, then buried his face in my ass and began licking my boy-hole (the only part of my body that hadn't been changed by doctors). I nearly jumped out of my skin as his tongue drilled into my body's most sensitive area. Nick was eating the same asshole he used to fuck as a kid. He wasn't eating Alexandra's asshole, he was eating Alex's. He swabbed my anal orifice with spit, lubing it thoroughly before aiming his cock back up to my hole. I recalled all the times I had lay in my own twin sized bed late at night and into the wee hours of the morning with Nick (or his brother Pete) on top of me, holding their hands over my mouth to keep me from making too much noise and waking my father down the hall while they fucked me. I remembered moaning into their palms as they humped away on top of me, giving me every inch of their teen cocks as they fucked me until they came in my ass.

Now I felt Nick's cock head kiss against my asshole. I felt the pressure increase as he began to push into me. I relaxed my anal muscles, allowing safe passage into my rectum. As soon as the head entered me, I tightened back up, squeezing his slick shaft as it continued to slide through. "OOOOhhh yeah that feel great...!" he moaned, his face just behind the back of my head as he sank his big prick all the way into me.

Nick lay down across my bare back as he reached down under me to grab two hefty handfuls of my tits. I could feel him squeezing and molesting them as he ground his hairy pelvis into my soft ass. Slowly he began to fuck me, pulling back to retract his buried cock, then pushing forward to sheath it all back up inside me. I loved the way his cock felt in my anal pussy, bringing back old times as two old friends reconnected to become one.

Nicolas pushed his face beside mine as he breathed into my ear and kissed me along the side of my face and neck. While still a little rough, he was much more tender with me now than he was when we were teens. He had always fucked me as if he had something to prove, as if dominating me. He never made love, he just fucked me, anyway he saw fit. I was nothing to him but a convenient hole, something for him and his brother to practice on until they got real girlfriends. But now was a different story. Now I not only felt Nick's cock pumping through me, but I also felt his hands pulling at my tits and playing with my clit. I felt his lips kissing at my face and neck, his tongue entering my mouth and body in ways it never did when I was a boy.

I arched my torso up off the bed, tilting my head back and sideways to kiss. Nicolas knew what I wanted as he stretched his neck to meet me. Our lips touched again as he slipped his tongue back into my mouth while he fucked me. His hands pulled and squeezed my breasts, making my sensitive nipples rock hard with desire. My ass cheeks clinched every time Nick thrust through them, causing my anal muscles to milk and massage his thrusting rod. Nick groaned into my mouth as he picked up the pace, his thrusts getting harder as his breathing became labored. I started pushing my ass back against him, fucking his cock with my ass and milking the shaft with my asshole. I could hear Nick starting to gasp for breath as he doubled his efforts. He rammed his hips into my ass over a dozen times, giving me the full length of his staff before his dick finally exploded in my colon.

"AAARRRRHHHHGGGG...!!" he screamed at the top of his lungs as he fired shot after shot of thick hot ball cream directly into my ass.

"OH GOD...! OH GOD...! I FEEL IT...! I FEEL IT...!" I panted breathlessly into his kissing mouth as his dick jerked and pulsated wildly inside me. I could feel my rectum becoming sloppy with his load, the heavy deluge flooding my rectal passage as his cock pumped out freshly made gobs of juice.

Nicolas fell weakly against my back, our lips still touching as we breathed in each other's breathes. I could still feel his cock throbbing inside of me when my second anal orgasm hit. All at once my ass cheeks locked together, trapping Nick's cock as my anus started to wildly milk his pulsing shaft, pulling out the last drops of his cum as my anal muscles sucked him dry. I feel forward onto the mattress with Nick still on top of me. We laid there for several long minutes, his dick slowly dying inside me as his heart beat against my back.

"That was great..." he finally said after a long silence. "...but I've got to get into the office before my wife pops up unexpectedly!"

"She does that often, does she...?" I asked, as he removed his soft cock and climbed off of me.

"She will now that she's seen YOU in my office!" he joked, searching for his clothes scattered about the floor.

"Did she suspect anything yesterday...?" I asked curiously, rolling over onto my back.

Nick stared down at my flawless body, his eyes lingering on my fat tits and trimmed cunt. I knew he wanted more!

"Definitely!" he said as if reading my mind. "What wife wouldn't suspect something after seeing a beautiful mysterious woman leaving her husband's office...?" he asked, slipping on his boxers and pants. "But don't you worry about Donna..., I've got her right where I want her!"

"Oh yeah..., and where's that...?" I asked, sitting up on the side of the bed.

"Wrapped around my little finger..." boasted Nick, as cocky as ever. "...right where I'm about to put YOU too...!" he added with a grin.

"Oh you THINK so, huh...?" I asked, turned off by his cockiness.

"I KNOW so!" he said confidently, walking over to me after throwing on his dress shirt. Without saying another word, he grabbed a fistful of my long blonde hair (yanking my head back), then kissed me fully on the lips. Despite my initial anger with his cockiness, I felt my body melt when he tongue once again entered my slack mouth.

Nick kissed me hard for a full minute, then broke the kiss as he pulled back and smiled down at me with that self assuredness that always made me do his bidding. In a flash (and all too soon) he was dressed and out the door, promising that this would not be the last time I saw him!

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

Next: Chapter 9


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