tagTranssexuals & CrossdressersDaddies New Girlfriend

Daddies New Girlfriend


Part 1

Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cynthia on more than one occasion. Jerry had been dressing up every Friday night for about three months and still every time he went snooping thru his Mother's stuff he was amazed at the things he found lurking at the back of his parents' huge walk-in wardrobe. Then he found the chest containing his Mother's lingerie, seeing this new abundant collection of lingerie poor Jerry couldn't help himself.

The suspenders G-strings and matching bra sets in his room paled in comparison to what the chest held. Slowly reaching into the wooden chest as the silk, satin and lace touched his skin it sent electric shocks through out his entire body, his teenage cock was rock hard and he knew why. Jerry had been fantasizing for some time now just what it would be like to wear just such totally feminine clothing. He kept looking slowly stroking his dick through his shorts. "Why the fuck not!" Jerry pushed his shorts and under pants down then kicked them away into a corner, his 6 inches bobbed to and fro. Gently gripping his shaft Jerry looked at his reflection in the mirror and he liked what he saw. Slowly he started moving his clenched fist along his ridged tool a long low groan of pleasure escaped his throat.

"Your gonna look so good in sexy lingerie Jerry, I can't wait to see your cock hidden behind sexy Lycra and lace."

Jerry picked out a 4 inch wide black lace trimmed in fire-engine red suspender and matching cup bra. He quickly snapped the suspender around his waist followed by the cup bra around his chest. His rampant dick poked out at a right angle, Jerry hadn't been this turned on in his life. He put his hands on his hips and admired his reflection, Jerry liked wearing sexy lingerie and when his next thought came he simply shrugged his shoulders and went with the flow.

"We'll have to hide that Jenny, and where are your stockings?"

Jerry crossed to the trunk and quickly found the black Lycra G-string and lace top stockings he knows were in there. Pulling out a new packet of black fishnets he saw a zip up bag in the corner. Opening it Jerry was delighted to find it contained a whole host of make-up. 4 or 5 different shades of mascara at least 10 separate packs of eye-shadow / eyeliner what seemed like a ton of blushers in a myriad of shades but strangely there was only a single tube of lip stick. Jerry took it along with the stocking and sat at the dresser he rolled the fishnets up his smooth legs and clipped them to the suspender. Standing he stepped into the Lycra G-string, buy now his erection had subsided and he was able to bend it backwards between his legs tucking it away. Jerry struggled to get the Lycra prison all the way up around her boyish hips but finally managed.

He had to stop himself from staring at his reflection because it made him far to excited, instead he opened the bag and dumped the contents out onto the dresser. Taking a big gulp of air Jerry looked himself in the eye.

"Come on Jenny you know you've always wanted to do this."

A sexy smile crossed his face.

"Oh yes I have wished this day would come. What do you want me to do? Make myself all slutty for you? Is that what you want?"

As he said the words he felt exhilarated and even though he was submitting him-self he still felt liberated funnily enough. Every fiber of his being seemed like it was pleasured at the same instant twenty minutes later Jerry had finished putting his face on and was proud of his handy work, Jerry pursed his painted lips and blew his reflection a kiss it was now time to put the finishing touches on. Jerry rummaged around in the wardrobe until he found a sexy short latex mini that shows Jenny's stocking tops clearly. As usual Jerry went down stairs and watched a little television before retiring to his Father's King sized bed where he masturbated while watching himself in the huge mirror.

Doug pushed the last file into his out tray finally able to take a break he logged onto the home security system. As the web-cam opens he finds Jerry son sitting directly in front of the mirror dressed in his dead wife's clothes. Doug immediately moves to close the web cam but when Jerry picked up Cynthia's butt length red wig and slipped it onto his head the resemblance to his dead Mother was uncanny. Doug couldn't believe it, his cock started to get hard for the first time since Cynthia's death.

"Fuck off! He's your Son. He's a fag!"

But Doug still couldn't stop himself from watching, his brain was telling him no but something far stronger over rode those impulses. As Jerry started applying bright red lip stick Doug realized he was rubbing the growing bulge in his trousers. Pulling his hand away as if he'd received an electric shock Doug clicks the close icon on the web cam. "Agh what are you thinking!" Doug closes his eyes and tried to get the images out of his head instead of Jerry all he sees is Cynthia.

"Oh God how I miss you Cynthia Honey."

Before going home that night Doug brought up the security program and played back the footage he'd copied earlier. He quickly saves a dozen or more still photographs where Jerry resembles Cynthia the best. Arriving home he studied Jerry's face as closely as he dared and couldn't detect the slightest hint of make up and it would be the last thing he'd ever mention it to Jerry. For the next week Doug found it harder and harder to concentrate on his work, he couldn't wait for everyone to leave each day so he could check his home security system. As each day goes by and he doesn't discover his special girl Cynthia, Doug finds it exasperating. Finally on Friday he was surprised at how delighted to see his son sitting by the mirror applying eye shadow when he logged on. This soon becomes a Friday night ritual and Doug doesn't let on but continues to secretly photograph Jerry's cross dressing sessions.

Now when ever his son is dressed Doug refers to him as Cynthia. Soon Jerry starts trying more of his Mother's make-up, but still picks up his favorite long red wig every time and this pleases Doug as it to is his favorite wig too. Jerry could still detect a feint trace of his dead Mother's perfume. Inhaling deeply he sighed and thought that this is probably why his Dad hadn't gotten rid of Cynthia's considerable wardrobe. Each week Jerry stole more and more of his dead Mother's lingerie, he didn't wear anything his normal clothes but his Mother's sexy underwear anymore. With out realizing it Jerry's Friday night ritual had become his Father's Friday night ritual too.

Doug had quickly come to terms with watching his son dress up in his wife's clothes it was as if Cynthia lived on through the dressed up Jerry some how. What clinched it was the fact that he actually got an erection while watching Cynthia's Friday night shows. The first time He'd kept watching and saw Jerry slowly peel off his Latex G-string to reveal a freshly shaved semi hard clitty he thought he'd be repulsed but instead was hooked. There was something extremely erotic about a totally hairless cock poking out from between some sexy lingerie Doug wrapped his fist around his rigid tool and enjoyed a long awaited wank. It was the first time he'd cum since Cynthia's death, Doug continued to collect still photos and a few cam shows from Jerry's Friday nights he even found himself fantasizing about using Cynthia, as time passes he warms to the idea.

Doug had now been watching his special girl Cynthia via the security system web-cam for nearly 5 months now and decides its finally time he took the next step. Arriving home 3 hours early Doug switches off the motor and rolls down the drive and into the garage almost silently. Creeping up the stairs he glances at his Rolex and knows exactly where to find Jerry AKA Cynthia. Walking into his bedroom and finds his teenage son lying on his stomach across the King size bed, dressed in a pair of four inch spike stiletto heels with black fish-net stockings the tops of which peek out from under his short Lycra mini skirt every time Jerry kicked his feet. Neatly tucked into the wide waist band was a sheer white semi see-thru blouse, from behind it was clear just how see-thru it was. The low back and thin straps of Jerry's body suit were there for everyone to see and his father new from seeing his dear departed wife in the very same outfit when his son turned around nothing would be left to the imagination.

The air was filled with the familiar scent of his dead wife Cynthia's favorite perfume. Jerry didn't hear his Father come into the room behind him Doug folded his arms and waited. Doug glanced at the dresser mirror and spied his son's reflection, sure enough he could see almost all off his son's Latex waist clincher/body suit with the suspenders attached. What really caught his attention was the waist length red wig Jerry was wearing he spent some time doing his make-up and wore his Father's favorite super slutty shade of red lipstick. (What choice did he have anyway? None.) Jerry's eyes were covered in mascara, eye-shadow and eyeliner. Doug saw the blood drain from Jerry's face when he realized it was his Father's reflection in the mirror he was blowing kisses at.

"What the fuck is going on here?"

"Dad! It's not what you think."

Jerry's movements caused his skirt to ride up showing more of his smooth thighs the higher it goes the harder Doug got. Putting a slight hint of menace in his voice Doug asks.

"What the fuck am I going to do with you?"

Jerry could bring himself to meet his Fathers gaze any longer. Dropping his eyes Jerry nervously bit his lower lip, before he knew what He'd said Jerry replied in an almost inaudible voice, it just slipped out.

"Whatever you want."

In a flash Doug steps forward he didn't want to give Jerry a chance to reconsider, this was better than he'd imagined.

"What did you say?"

Jerry knew he was trapped his faced started to burn as he blushed brightly, lucky for him the heavy make-up he had on hid this from his Father. Clearing his throat Jerry answered in his best girlie voice only a little louder.

"Whatever you want Daddy."

"That's what I thought you said well for starters you can suck my cock you little whore."

Jerry gulped and his eyes almost popped out, did he hear his Father right? Did he say?

"Suck his cock?"

His Father's actions answer that particular question Doug pushes his trousers down around his knees and moves beside the bed. Jerry can't believe his luck he'd been watching slutty girls just like himself doing just what his own Father wanted him to do. Jerry had fantasized about men's cocks but never actually even seen another mans cock in real life, he was eager to have his first taste though. Licking his shiny red lips Jerry looked at through the long red fringe into his Father's eyes.

"Did I hear you right Daddy? Did you say suck your cock?"

Having never done this before Jerry wasn't quite sure where to start, he couldn't believe it was his own Father's tool less than an inch from his lips. He needn't have worried because Jerry took to it like a natural. Wrapping his hand around his Father's shaft as best he could Jerry pulled his Father closer. Flattening his wet tongue Jerry slurped at the huge bulbous head greedily swallowing the gathering pre-cum. Opening his mouth as wide as he could Jerry took his Father's thick cock into his warm wet mouth. Looking down Doug swats away Jerry's hand and grasps his meaty shaft directing it towards Jerry's open sucking mouth. Then reaching out Doug places a hand on his Jerry's head to hold him still he slowly starts thrusting his hips slowly driving his hard tool deeper into Jerry's throat. Changing his grip Doug strong fingers are twirled and twisted through the long wig and deep into Jerry's soft hair underneath. Pulling Jerry forward wit each thrust Doug forces his cross dressed son to suck his thick cock. Having Jerry call him Daddy and making his son swallow a fat cock made Doug even hotter and thinking of him as the Cynthia he'd always desired made it even sexier.

"That's it Cynthia, suck Daddy's fat cock, you little whore."

Hearing his Father call him Cynthia made Jerry so happy that he desperately wanted to return the favor. Without letting his Father's rigid cock escape his sucking mouth Jerry rolled over onto his back and relaxed allowing his head to drop backwards. He'd seen loads of girls in this position and he knew it allowed Doug's tool easier access to his willing throat. Doug grunted with each quickening stroke, it had been so long since he'd had any sort of sex and it didn't take much before he was ready to explode.

"That's it ya little Cockpig, suck that big fuckstick, suck Daddy's cock ya little whore cause He's gonna cum down your slutty throat soon Cynthia Honey."

Jerry couldn't believe the way his Father was talking to him but it was such a turn on. Sucking his first cock Jerry was surprised just how much better the real thing was compared to what he'd ever imagined or fantasized about for that fact. He'd been drinking his own cum for ages he couldn't wait to taste his Father's sticky jism.

"Get ready Cynthia Honey, I'm gonna empty my balls in your mouth soon."

Groaning loudly Jerry redoubled his suction and began running his fist along his Dad's rock hard shaft. "MMMMMM ughhhhh ughhhhh ughhhhh MMMMMMM." Jerry slides up across the bed slightly, trying to get as much of his Father's massive dick into his willing throat that he possibly can. Hearing his Dad is close to orgasm Jerry reaches out and starts scarping his brightly painted cropped finger nails across Doug's hairy ball sack.

"Aghhhhhh fuckkkk yessssss Cynthia Honey MMMMMMM, fuckkkk yessssss."

Doug's peach sized balls tighten and grunting loudly he lets his orgasm overtake him. Doug's hips piston back and forth as he drives his tool into Jerry's throat. The first thick ropey squirt of Doug's cum both surprises and nearly overwhelms Jerry. It fills his mouth and throat then is followed so quickly by the next that he chokes and coughs Doug laughs loudly

"What's a matter Cockpig? Can't Daddy's Little whore take it?"

Two thick streams of man juice squirt from his nose but his Father couldn't care he just thrust his cock back into Jerry's throat Holding him firmly on his pumping tool until he empties his balls deep in Jerry's throat. Poor Jerry doesn't have any other choice but to try and swallow as best he can or suffocate. After what seems like three or four cups full of semen is deposited in his gullet his Dad's tool finally stopped shooting and pulsed as the last few drops leaked from the single eye. Jerry's best effort would only be half an egg cup at best so he can't quite believe just how much wonderful tasty cum his Dad can shoot at once. Doug pulled up his trousers he felt so much better now and it didn't worry him in the slightest that it was his Son who'd just sucked his cock but with Jerry dressed like he was Doug didn't trust himself, he didn't want to spoilt it now.

"Get off my bed Cynthia I'm finished with you for today."

Feeling used Jerry stands and walks to his own room, his stiff dick is bent back painfully and he can't wait to relive himself. Closing the door behind him-self Jerry reaches under the hem of his skirt and pulls the G-string aside. Out pops a semi hard hairless 7 inch clitty and two smooth balls watching himself in the mirror Jerry strokes his shaved clitty He's so worked up from sucking his Father's tool it only takes seconds before his balls tighten and cum is squirting into his cupped palm. His Father ignores him for the next few days, they hardly speak. Jerry's not sure what to do He doesn't want to bring it up but one thing is for sure he definitely wanted a repeat performance, three days later he has a plan.

Since the last time his Dad noticed him was when he dressed up to look exactly like his dead Mother Cynthia, Jerry was going to make sure his Father caught him dressed again only this time he'll be dressed as even more of a super slut. Jerry couldn't wait any longer so he went decided to skip classes that afternoon. So Jerry arrives home from school early to get ready for his Dad's arrival later that night. Jerry had spent days thinking carefully about his outfit, eventually deciding on a black and red cup-less Latex dress which from experience would look as if it'd been spray painted onto his petite frame along with stockings a suspender and matching G-string. The matching Latex bra top came separate and Jerry also knew that the fake tits he'd bought from the Internet would look quite good in it too. This was all laid out beside the black 4 inch stiletto boots. Taking courage from the previous encounter Jerry showered then dressed taking special care with his make-up. Even though Doug had spent the last hour and a half locked away in his office down town watching Jerry prepare for his arrival. When he did arrive home half an hour later Doug still had to look twice to make sure it wasn't a very slutty version of his dearly departed wife Cynthia. Jerry met Doug in the kitchen carrying a glass of Bourbon the heels of his boots clicked in time to the ice clinking in the glass.

"Here you go Honey."

Jerry felt a rush of pleasure when he called his Father Honey, and didn't get an adverse reaction after all it was his Mother's pet name for her husband.

"Thanks Cynthia Baby I need this."

Doug had quickly decided to play along just to see where it might lead, in truth watching his cross dressed son parade around for him excited Doug quite a lot. Taking a large gulp from the glass Doug slipped a hairy arm around his son's Latex torso slowly allowing it to rest gingerly on the wide elastic belt enclosing his slim torso. Even though Jerry was wearing 4" heels he was still several inches shorter than his Father. It wasn't the first time Jerry had thanked God that he'd taken after his Mother's side of the family. At 4'9" tall and 115 lbs he was blessed with a petite frame, almost exactly the same size as his Mother. Since her death two years earlier he hadn't had a hair cut and his reddish blonde hair had grown well past his shoulders.

"Agh that hits the spot Cynthia Honey."

Doug placed his glass on the counter top and pulled Jerry closer with a finger under his chin Doug lifted his Son's face upwards. Looking up Jerry could smell a mixture of sweaty masculine aroma and Bourbon. Moving closer to his Son's expectant upturned face Doug plants a wet kiss on his son's lips, slowly he pushing his fat tongue into his boys' mouth. Jerry simply melted into his Father's arms this is exactly what he wanted. As Doug's wet tongue probed his Son's willing mouth his free hand was busy roughly kneading Jerry's latex clad butt. After the initial shock Jerry kissed his Father back, playfully teasing him with the tip of his pierced tongue, now he could taste the Bourbon. Jerry marveled at how erotic his Father's rough whiskers felt against his freshly shaved skin, he moaned into his Dad's open mouth. Doug pulled back and broke their kiss a strand of saliva still joined the pair for a fraction of a second.

"Mmmmm that was nice Baby such a talented tongue. Now what's for dinner?"

"Steak and salad I hope that's okay Honey?"

A devilish grin formed on Doug's mouth, he smiled broadly. "Well it's not just a Man that needs meat is it Sweetness?"

Jerry blushed brightly but quickly recovered.

"Oh Honey your so, so right. We girls need a good dose of meat occasionally."

"More than occasionally Cynthia Sweetie more than occasionally."

As Jerry passes his Father's chair Doug swats his sons' Latex clad butt playfully.

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byLilLindaMelons© 9 comments/ 128129 views/ 90 favorites

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