His wife Cynthia died, his crossdressing son steps into her shoes, literally.
This story is completely fictitious and is for adult readers only, not for minors. As such you the reader must be advised that it contains graphic, explicit sexual descriptions of Incest and Gay sex. IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE NOW.
I in no way condone the actives described below, nor do I support those that do. My stories are for entertainment purposes only.
This is the work of a fertile mind. It remains the copyright property of the author and therefore may not be copied or reproduced without their express permission. As stated, it is fiction; Any similarities between characters and real people are unexpected and unintentional. If you recognize yourself or anyone you know. Please tell me to change any future chapters.
If sex between older males and young teens, gay sex, or incest offends, leave now.
For those that do like the above, please read on. I try to write detailed, sexy stories; My objective is to hopefully excite the reader. So, sit back, put your ear buds in, or get your headphones on. Take hold of yourself and listen to the tale of Jerry and his dad, Doug.
Part 1
The Discovery
Doug suspected his 14-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 webcam behind the mirror in his bedroom. He had used the very same two-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 through his mother’s things. 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 could not 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 throughout 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 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 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 had not 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 went back to the trunk and quickly found the black Lycra G-string and lace top stockings he knew 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 eyeshadow / 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 too excited, instead he opened the bag and dumped the contents out onto the dresser. Taking a big gulp of air, Jerry looked at 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 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 downstairs 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 webcam 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 could not believe it; His cock started to get hard for the first time since Cynthia’s death.
“Fuck off! He is your son. He is a fag!”
But Doug still could not stop himself from watching; his brain was telling him no but something far stronger overrode 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 had received an electric shock, Doug clicks the close icon on the web cam. “Agh what are you thinking!” Doug closes his eyes and tries 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 replayed the footage he had 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 could not detect the slightest hint of makeup, and it would be the last thing he would ever mention to Jerry. For the next week Doug found it harder to concentrate on his work; He could not wait for everyone to leave each day so he could check his home security system. As each day goes by and he does not discover his special girl, Cynthia, Doug finds it exasperating. Finally on Friday he was surprised at how delighted he was to see his son sitting at the mirror applying eye shadow when he logged on. This soon becomes a Friday night ritual, and Doug does not let on but continues to secretly photograph Jerry’s cross-dressing sessions.
Now whenever 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 too is his favorite wig too. Jerry could still detect a feint trace of his dead Mother’s perfume. Inhaling deeply, he sighed and thought this is why his dad had not gotten rid of Cynthia’s considerable wardrobe. Each week Jerry stole more of his dead Mother’s lingerie; He did not wear anything under his normal clothes but his mother’s sexy underwear anymore. Without 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 somehow. What clinched it was that he 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 would be repulsed but instead was hooked. There was something extremely erotic about a 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 webcam for 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 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 filled with the scent of his dead wife Cynthia’s favorite perfume. Jerry did not hear his father come into the room behind him. Doug folded his arms and waited, glancing at the dresser mirror and spied his son’s reflection, sure enough he could see 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, eyeshadow, and eyeliner. Doug saw the blood drain from Jerry’s face when he realized it was his father’s reflection in the mirror, that 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 not bring himself to meet his father’s gaze any longer. Dropping his eyes, Jerry nervously bit his lower lip. Before he knew what He had said, Jerry replied in an almost inaudible voice; it just slipped out.
“Whatever you want.”
In a flash, Doug stepped forward, and he did not want to give Jerry a chance to reconsider; this was better than he had imagined.
“What did you say?”
Jerry knew he was trapped his face started to burn as he blushed brightly, lucky for him the heavy make-up he had on hid most this from his father. Clearing his throat, Jerry answered in his best girlie voice, 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 what Jerry thought he did? Dad wants me to suck his cock.
His Father’s actions answer that question: Doug pushes his trousers down around his knees and moves beside the bed. Jerry cannot quite believe his luck; He has 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 cock in real life, he was eager to have his first taste though. Licking his shiny red lips, Jerry looked 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 was not sure where to start, he could not believe it was his own Father’s tool less than an inch from his lips. He need not 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 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 with 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 had always desired made it even sexier.
“That’s a good girl Cynthia, suck Daddy’s fat cock, you little whore.”
Hearing his father calling 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 had seen loads of girls in this position, and he knew it allowed Doug’s tool to have easier access to his willing throat. Doug grunted with each quickening stroke, it had been so long since he had had any sort of sex, other than his hand, it did not take much before he was ready to explode.
“That’s it ya little Cockpig, suck that big fuckstick, suck Daddy’s cock ya little cross-dressed fucking whore cause He’s gonna cum down your slutty throat soon Cynthia Honey.”
Jerry could not 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 had ever imagined or fantasized about for that fact. He had been drinking his own cum for ages he could not 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 can. Hearing his dad is close to orgasm Jerry reaches out and starts scarping his brightly painted cropped fingernails 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 is the matter with you my little cockpig? Can’t Daddy’s Little whore take it?”
Two thick streams of man juice squirt from Jerry’s nose but his father could not careless, 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 gullet. Poor Jerry does not have any other choice but to try and swallow as best he can or suffocate. After what seems like three or four dessert spoonfuls of semen is deposited in his gullet, Doug’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 a dessert spoonful at best so he cannot 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 spoil 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 cannot wait to relive himself. Closing the door behind himself 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 does not want to bring it up, but one thing is for sure he 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 could not wait any longer, so he decided to skip classes that afternoon. Jerry arrived 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 had 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 had 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 particular care applying his makeup. Even though Doug had spent the last hour and a half locked away in his office downtown 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 was not a very slutty version of his dearly departed wife Cynthia. Jerry met Doug in the kitchen carrying a glass of Bourbon with 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 did not 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 was not the first time Jerry had thanked God that he had taken after his mother’s side of the family. At 4’9″ tall and barley 100 pounds, he was blessed with a petite frame, the same size as his mother. Since her death two years earlier he had not had a haircut, and his reddish blonde hair had grown well past his shoulders.
“Agh that hits the spot, Cynthia Honey.”
Doug placed his glass on the countertop 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 pushes 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 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 soft skin, Moaning into his dad’s hungry 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 a really nice kiss Baby, and with such a talented tongue too. Now what have you prepared 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.
You look especially nice tonight, Cynthia Baby. Did you dress up for me?”
Tossing his head to flick the long red fringe out of his eyes, Jerry looks back over his shoulder and smiles as sweetly as he could manage.
“Yes, of course, Daddy. Who else do I have to dress up for?”
“Well, that can always be fixed, can’t it? I suppose I could always bring one of the out-of-state reps here with me for dinner sometime. That’s if you’re a good girl, Cynthia Baby.”
Jerry did not trust himself to answer this question without delay. He quickly left the room using the excuse he had to check the steaks. Seeing Jerry’s embarrassment, Doug followed his son into the kitchen. He had seen the reaction and was intrigued to see just how far Jerry would let him push it.
“So, is there a special reason why you’re all dolled up tonight, Cynthia Baby?”
Jerry smiled back at his father, slowly toying with the two-inch gold hoop earring hanging from his right ear.
“Well, there’s no special reason really, I just wanted to look good for my Daddy.”
Smiling sweetly, Jerry continued.
“Can’t a girl dress up nice for her Daddy?”
Doug wanted to take it slowly with his son. He did not want to scare him off but from Jerry’s actions and conversation he was becoming increasingly certain there would not be a problem. They ate their meal in near silence only making small talk now and then. Jerry was starting to get desperate for something to say, and Doug made sure not to change the topic of conversation to what he desired, sexual relief or gratification. It took his willpower to stop jumping on his son. The only thing that did was the fact that he masturbated twice in the office while watching Jerry transform into Cynthia before coming home. Finishing the delicious meal, Doug pushed the plate away and feeling indebted, Doug pulled out his wallet and dropped three-hundred-dollar bills on the table.
“Great meal Cynthia Baby, get your-self something nice with this.”
Jerry picked up the notes, folding them carefully before putting them in the top of the stocking, just beside the suspender clip. He looked up at Doug.
“Why thank you Daddy you’re too kind, do you have any suggestions?”
“Well, I do like those boots you’re wearing Baby. How about a pair of high thigh boots with 6-inch heels and it wouldn’t hurt if you got your ears pierced properly either.”
The next four Friday nights followed the same pattern; Doug would arrive home to a warm welcome from Cynthia. They would sit down for a hearty meal and then Doug would excuse himself and retire to his den. Poor Jerry was desperate to have his father again, so he decided this weekend he would step it up a notch. Little did Jerry know, but his dear old Dad had that same idea. Instead of watching his son transform into Cynthia, he was recording it and was out shopping for a special gift for his son. Some sexy lingerie a matching G-string and bra set the assistant at the lingerie store was extremely helpful when it came to choosing a lace up corset that matched. The one Doug finally picked had six suspender straps.
Jerry on the other hand was quite a bit bolder in his plans he had long passed the point of caring about what anyone else thought. The only thing on his mind was how to bring about another session with his father. Jerry was desperate to have his dad’s big cock again, his desire to drink Doug’s jizz was overwhelming. He dressed in a matching green semi see thru G-string, bra and 6″ wide suspender set. To the suspenders, he clipped white stay-up stockings, stepped into his knew white six-inch stilettos and strapped them around his ankles. From his mother’s wardrobe he had taken a green and red tartan skirt that could not have been any shorter, in total it was only 12″ wide from waist to hem. So, not only did his stocking tops, but all the attached suspender straps showed. Jerry lifted the fake boobs into place he had ordered them from eBay weeks ago, and they had only arrived that afternoon.
He had spent over two hours trying on most of his lingerie seeing which outfit looked the best. The one he had chosen was made of stretch Lycra, and the weighted fakies filled the cups of his bra perfectly. Jerry adjusted the straps of his bra and reached for the long sleeve white blouse he purchased that morning. It hung over the back of the chair. Buttoning the blouse, Jerry saw his father’s large dresser mirror. Tossing his head from side-to-side, Jerry stood on one hip then the other checking his profile. Pursing his lips Jerry blew a kiss at the long-haired red head looking at him from the mirror.
“My Cynthia, you do look gorgeous, don’t you?”
“You bet I do.”
Glancing down at the clock Jerry realized it would be quite a while before his dream man would be home. To pass the time he decided to paint his nails, he knew just which draw held his mother’s considerable collection, but he already knew which colour he was looking for, something to match his slutty red lipstick. Crossing his stocking clad legs, Jerry proceeded to paint his nails, carefully blowing them dry when finished. For the next half hour Jerry practiced his slutty girlie looks. When Doug arrived, Cynthia was waiting with a double Bourbon as he walked in.
“Agh you’re a marvel Cynthia Baby; You know what I need.”
Doug had worked on this opening line; it could be taken to have so many meanings. Rewardingly, Jerry could not have answered any more positively.
“That’s right Honey Cynthia knows what her man needs.”
Although encouraged Doug to let it pass.
“You’ve out done yourself tonight, Cynthia Baby, you look absolutely gorgeous.”
Jerry took hold of the hem of the super short skirt and pulled it outwards; he bobbed down in a cute curtsey.
“Why thank you Honey, your so kind.”
From the kitchen came the beeping of the microwave oven, it had finished heating their TV meals. As they ate, Doug devoured the food as heartily as his eyes devoured Jerry’s scantily clad body. Pushing his plate away, Doug loosened his belt a notch and belched loudly.
“Not bad for a quick TV dinner Cynthia Baby.”
“Thank you, Honey, I could’ve made something better if you wanted.”
“No, no I can’t expect you to prepare gourmet food all the time now can I Cynthia Baby?”
“Whatever you say Honey, it doesn’t bother me.”
“That’s my girl.”
Hearing his father refer to him as his girl made Jerry’s chest swell with pride; To say nothing about what the wors did to his tucked boy clit. He smiled, licked his lips, and batted dark mascara-covered eyelashes. Jerry’s brain was doing somersaults his plan was working out better than he dared hope.
“I’ll always be your girl Honey, you know that.”
Jerry stood and cleared the table; Doug watches his boy marveling at the way he instinctively knew what to wear to excite his old man. It did help that he was using his mother’s wardrobe for the main part.
“Another drink Honey?”
“Mmmmmm yeah why not Cynthia Baby, make it a double and have one yourself.”
This was the first time Doug had let his 14-year-old son drink alcohol even though he knew Jerry had tried it before. Doug followed Jerry into the lounge room. He sat on the sofa while Jerry half-filled his father’s glass with Jack Daniel’s then another with Vodka into which he squirted a little soda. Jerry dropped several ice cubes into each glass and turned towards where his dad sat. Doug took the offered glass of whisky, picked the remote up from the table and patted the seat beside him-self.
“Come sit here with daddy Cynthia Baby.”
Jerry slid into the leather seat beside his father; Doug’s meaty right hand settled onto Jerry’s stocking clad upper thigh. As they watch Television, Doug’s fingers slid over Jerry’s thigh slowly tracing the suspender straps and the line of his stocking tops repeatedly. This was having such an effect on poor Jerry; He was glad he had later decided on wearing two G-strings. His clitty was getting so hard it would have ripped its way out of a single Lycra prison. Jerry gulped down half of his Vodka when his Father’s hand slides higher. Doug takes the glass from Jerry and places it beside him on the coffee table. Turning back, he pulls his young teenage son closer and into an erotic embrace slowly massaging his fake boobs while his hot wet tongue searches the insides of the boys’ mouth. Jerry could taste the whisky on his father’s tongue; this was a huge turn on.
“Cynthia Baby, do you remember saying you would do whatever I asked?”
“Yes, of course I do Daddy, of course I do, and my offer still stands.”
“Good cause my dick needs another good hard sucking Cynthia Baby do you think you can handle that?”
Smiling broadly, Jerry let his painted fingernails trace Doug’s stomach onto his zipper.
“I’m sure I could handle that and a whole lot more Honey, anyway if I can’t I sure hope you’re willing to teach me.”
Seconds later Jerry had unzipped Doug’s fly and was fishing around in his trousers trying to get his dad’s big dick into the open. Lifting his buttocks off the chair, Doug unclipped his belt and Jerry pulled his father’s trousers down around his knees. Looking up, Jerry’s gaze was drawn to the lump in Doug’s underpants. He sank to his knees and lightly gripped his Father’s ankle.
“Honey, you’d be more comfortable if I take your shoes off, then we can get those trousers out of the way too.”
Doug lifted first one foot and allowed Jerry to remove the shoe then the other was offered. Before straightening up Jerry slipped his father’s trousers off, folded them, and placed them on the floor beside the lounge. Kneeling in front of his Father Jerry put his hands on his dad’s knees then looking up through his long-mascaraed eyelashes, he smirks then asks.
“Well Honey if you want Cynthia to suck that big dick of yours, you’d better get it out for her.”
Doug cannot get his boxers off quick enough, and as he struggles to push them off his feet, the head of his tool waves inches from Jerry’s face. When his dad collapses back into the leather sofa, Jerry moves between his knees. Reaching for the hard 10″ cock poking out from his father’s curly pubic hair Jerry lazily stroked.
“Such a nice big cock you have Daddy; Cynthia can’t wait to taste it again.”
Jerry ducked his head and licked the fat bulbous knob then took it into his mouth and sucked harder. Pulling back, his father’s dick came out of his mouth with a loud pop sound.
“Mmmmmmmm your big dick soooo yummy Daddy.”
Doug put his right hand on Jerry’s head, pushing the teenager down again.
“Shut up Cynthia and suck my fucking cock you little whore.”
Jerry did not have to be told twice, his mouth opened and accepted his dad’s huge cock head Jerry’s tongue flashed around the swollen gland while he applied steady suction. Tickling the heavy sack with his painted fingernails brought groans of approval from his dad.
“Aghhhhhh fuckkkk yeahhhhhh Cynthia Baby, that’s nice but lick my fuck pole lick it like it’s an ice-cream fagot.”
Doing as he is ordered Jerry pulls back and begins licking his way along one side then up over the knob paying particular attention to the leaking snake eye before working his way back down the opposite side. Up one side and down the other then from front to back Jerry does not leave a single spot untouched by his hot wet slippery tongue. Having seen it on the Internet many times it only seemed like a natural thing to do, and he knew he would love to have it done to him. Rhythmically stroking his father’s cock Jerry tilted his head and ducked down beside his dad’s massive shaft.
Jerry buried his nose in Doug’s pubic hair and inhaled deeply before quickly giving his heavy peach sized balls a severe tongue-lashing. Jerry opens wide and sucks one into his warm, moist mouth. He tries in vain to roll it with his tongue. It is way too big, but he is encouraged when he hears his father’s loud groans.
“Ohhhhh-aghhhhhh-aghhhhhh. Fuck Cynthia Baby you are a cocksucking marvel”
Jerry’s technique surprises the hell out of Doug in two ways. Firstly, he did not believe his son was experienced enough to try and secondly, he was amazed Jerry’s mouth could open wide enough for his balls to fit his mother could never manage that little feat. Jerry grasped his dad’s tool in both hands and began forcing himself down onto it, he was desperate to show his father how good a cock sucker the new Cynthia was. Doug relaxed into the plush leather sofa and throwing back his head gazed down at his special girl’s head as it bobbed up and down.
“That is it my girl, Cynthia Baby, lick it whore, lick my fucking cock, fagot cockslut whore. Lick that cock like the little whore you are. Show your Daddy what a little whore he has for a daughter.”
Being referred to as his Daddy’s daughter gave Jerry a huge thrill. Quickly changing positions Cynthia concentrates on working half of Doug’s tool in and out of his wet mouth; loud slurping noises fill the air. Jerry had been using bananas to practice his deep throating technique but his father’s massive 10″ fuck stick was a whole new dimension.
“That’s a good girl Cynthia Baby make your Daddy’s cock nice and slippery.”
Jerry was too caught up in the moment to realize the true meaning of his father’s comment. He continued licking away at Doug’s shaft blissfully unaware of what his dad had in store for his special girl.
“That’s the way Cynthia lick my fat tool you little crossdressing fag whore.”
When Doug pushed Jerry away, he did not know what was happening. At first, he thought his father had second thoughts and was going to chicken out. He felt heartbroken and looked up. Jerry knew that his tears were not far away.
“What’s wrong Honey?”
Doug stood above Jerry’s kneeling form, looking down at his son he could not help smiling.
“Nothing Cynthia Baby, nothing at all. There’s a present for you on the washer.”
Jerry stopped licking his father’s shaft and looked up.
“Can I have it now, Daddy? Please?
“Of course you can Baby. It’ll give Daddy some time to catch his breath.”
Jerry jumps to his feet and scurries towards the laundry where he finds the promised gift. Jerry carries the gift-wrapped box back into the lounge. Doug pats the seat beside himself.
“Sit here Baby girl.”
Dropping into the plush leather chair Jerry rips at the bright wrapping paper, inside he found a white box. Opening the box, he gasps. “Oh, thank you Daddy, it’s beautiful. Do you want me to put it on for you?” “No, not tonight I’ll let you surprise me Baby, besides you look so sexy tonight that Daddy’s gonna fuck his special girl.”
Jerry was not sure if his father’s huge cock would even fit inside his ass, but he could hardly wait to try. Doug grabbed his teen son’s wrist and spun him around, so he was now facing away from him. Doug pushed his son down towards the coffee table and began stroking his enormous dick to keep it hard.
“Okay Cynthia Baby show Daddy just what’s under that sexy skirt you’re wearing.”
Jerry quickly flipped the tartan skirt up showing his father the Lycra G-string disappearing between his plump butt cheeks. In a flash, Doug had reached out and landed a slap on Jerry’s left butt cheek. It made Jerry jump and Doug laugh. Then there was a second on his right cheek.
“Get that fucking G-string off, how do you expect me to fuck you when you have that on?”
Jerry bent from the waist at right angles and reaching up he slowly and seductively as he could began rolling the light blue Lycra down over his hips and then thighs, allowing them to gather around his knees.
“That one too ya silly Cockpig.”
Jerry does as He’s told and quickly slips the black lace G-string over his hips and down his legs. The cool air hitting his freed clitty made Jerry gasp in pleasure. “Ooooooooooo that feels so goooooood.”
“It looks good from my point of view to Cynthia Baby. Now back up a little more.”
Doug’s rough hand rested on his sons’ creamy white butt, gently guiding Jerry into position on the coffee table.
“That’s it my little Baby girl just a little bit further, that’ll do. Now arc your back and get ready for your Daddy, Cynthia.”
Jerry did not bat an eyelid at the word “Daddy”, but he noticed the way his father’s voice changed when he said it, Jerry was sure that his father found it a certain turn on. Bent over the coffee table with his ass pointing skywards Jerry felt so vulnerable but still could not wait for his father too make his favorite fantasy come true. Jerry tossed his head several times trying to move the long fringe from his eyes finally he looked back at his father.
“Is this where you want me Daddy?”
Doug did not miss a beat hands massaged Jerry’s white cheeks.
“Umm, yeah that’s fine Cynthia Baby.”
Suddenly Jerry felt a fat digit circling his puckered anus. Doug had picked up the tube of KY gel and unscrewed the cap. He squeezed another large glob directly onto Jerry’s hole. The combination of the cold lube and his father’s fat thumb made Jerry shudder. Doug smiled when he saw Jerry’s anus tighten due to the cool lube. Doug wiped the lube across the purple head of his large cock then pulled Jerry backward until his fat bulbous head rested against his son’s lubricated sphincter.
“Okay my little Cockpig, Daddy’s gonna leave it up to you to set the pace.”
Jerry was so horny and having rehearsed this very occasion with everything from vegetables to candles until he finally bought a dildo a month ago, he was more than ready. So, pushing back, Jerry tried to take his father’s thick tool. Jerry was having quite some trouble fitting his dad’s big knob inside his ass until Doug grabbed his son’s hips and thrust forward.
“Oooohhhhhhhhhhhhhhhhh Daddddddddy, ohhhhhhhhhhh yessssssssss Daddddddddy. Your soooo big Daddddddddy soooo deliciously big.”
“Well Cynthia Baby if you like that just you wait till Daddy’s cock is all the way in.”
Jerry moaned as the plumb sized knob entered his anus, Doug chuckled as he began thrusting his hips slowly. Doug stands up and holding Jerry’s hips he pounds away at his son’s greasy hole, gradually easing more of his monster tool into Jerry’s virgin ass. Reaching around Doug wraps his fingers around Jerry’s throbbing clitty and whispers in his ear.
“Does Cynthia like having her Daddy’s big cock in her ass?”
“Oh God yes Daddy, your little Cockpig whore Cynthia loves your big dick deep inside her willing anus. Fuck my ass Daddy fuck your little whore’s ass harder.”
Doug could not believe how loose his son’s ass was, it had taken several different dildos to open his mother’s anus so she would be ready for his sizable tool. Jerry’s ass had accepted his dad’s 10″ fuck pole with ease. The way he pounds his cock into Jerry’s slippery hole soon has Doug’s big hairy balls slapping his son’s body loudly on each down stroke Jerry moaned in time to the soft slapping sounds.
“Mmmmm Daddy, mmmmm Daddy, mmmmm Daddy, mmmmm Daddy, mmmmm Daddy.”
Feeling his balls tighten Doug knows he is nearing orgasm, sinking his cock all the way to his balls Doug pulls Jerry back against his groin, drilling his huge cock even harder into his son’s virgin ass. As he comes his hips buck and thrust involuntarily, luckily Jerry had been holding onto the coffee table like his life depended on it otherwise they both would’ve gone head over heels.
“Ughhhhh, fuckkkkkking sweeeeeeeet assssssss Cynthia Baby. Fuckkkk yessssss aghhhh yeahhhh take that Cynthia Cockpig, take your Daddy’s sticky cum.” Jerry wanted his father to enjoy this night as much as possible, so he started talking dirty too.
“Oh, Daddy you’re shooting in my ass. I can feel you are hot cum deep in my slutty ass hole Daddy. Your little whore has an ass full of her Daddy’s sticky cum.”
Doug slowly restarted pumping his hips, slowly driving his still leaking dick into Jerry’s sloppy hole.
“Aghhhh Fuck Cynthia Baby, your ass is a perfect fit for my fuckstick. When I pull out, I expect you not to spill a single drop of your Daddy’s special baby fluid, not a single drop. Understand Cynthia?”
“You want me to hold it in Daddy?”
“Yes, Baby Girl. Hold it in for Daddy.”
Doug pulled back until his cock flopped out with a loud slosh/plopping followed by a rush of air that had been trapped. Jerry snapped down on his sphincter as quickly and tightly as he could and just managed to stop any of his Father’s seed from escaping. Doug sat back on the sofa and admired his son’s cross-dressed form.
” Pull your panties up little Miss Cynthia Cockpig.”
Watching his son rearranging his lingerie Doug quickly concluded that fucking Jerry was ten times better than watching him dress up via the security system. Now it was time to put his plan into action, with luck in ten minutes’ time he would know just how much further Jerry would let him push the boundaries. Standing Doug offered his son a hand.
“Time for a shower Cynthia Baby.”
Jerry took his father’s hand and was dwarfed by his dad’s meaty paw. Doug pulled Jerry to his feet and guided him upstairs. Walking into the bathroom, Doug opened the glass recess door.
“Inside Cynthia Baby.”
Jerry stopped and started to undress.
“I SAID INSIDE COCKPIG.”
Jerry jumped at his father’s raised voice.
“But my clothes Daddy?”
“You should’ve thought about that earlier Cynthia Cockpig.”
Doug knew full well that Jerry could not have known but that was part of the fun of being a dominant their always right even when they are wrong. Jerry bowed his head and stepped into the shower recess. Not sure what was about to happen, he turned to face his father.
“On your knees Cynthia Cockpig, on your knees before Daddy, he’s got something special for his little Cockpig.”
Slowly sinking to his knees, Jerry was not sure what was happening but did as he was ordered. Doug positioned himself in the doorway about two feet from Jerry. Taking hold of his now soft cock, he points it at Jerry’s face, grunting Doug did the one thing his dead wife never let him he directed a stream of hot yellow piss at his kneeling son.
“Look up Cynthia Cockpig. Look up at your Daddy ya little whore.”
Looking up his father directs his wee straight at Jerry’s face, neck, and chest. His urine soaks into Jerry’s clothing, and Doug is pleased with the sudden new wet look.
“Ohhhhh fuckkkk, ughhhhh, ummm, ughhhhh Daddy.”
The surprise and excitement are evident in Jerry’s voice. He had dreamt and fantasized about golden showers he had even tried peeing on himself. This turned him on it was somehow erotic or exotic, besides, you would be surprised just how hot it really is. Doug decides to push Cynthia a little further just to see how far Jerry would let it go.
“Open wide Cynthia Baby. Open your slutty mouth for Daddy Cynthia Cockpig.”
Jerry had fallen into a comfortable submissive position when he had begun dressing in his mother’s things that afternoon, so by now he was conditioned to do whatever Doug told him to. Jerry’s mouth opened before Doug had finished speaking, but his aim was true. The long stream of piss arced across the gap quickly filling Jerry’s mouth. He did not know what to do; He’d only seen this in pictures on the Internet. Seeing Jerry in a dilemma, Doug pushed it again, closing his hand, reaching out and slapped Jerry’s face.
“Swallow it Cockpig, drink down your Daddy’s nectar Cynthia Cockpig.”
“Gulppppppp, gulppppp gulppppp gulppppp. Yes, Daddy gulppppp gulppppp.”
Doug expected Jerry to baulk or cough and choke but fuck me dead it was him that got the surprise of his life, Jerry’s was drinking his piss. His fucking Son was drinking his piss, Doug changed his aim and sprayed Jerry’s chest and neck before ensuring the last few drops ended up in Cynthia’s gaping mouth. Jerry had happily drunk every drop and was smiling sweetly when Doug stood back from the glass door.
“Gee Cynthia Baby, you must’ve been thirsty, Hehehehe.”
“Thirsty Daddy? Why do you say that?”
“Well, the way you just gulped down Daddy’s pee, I just thought that you must’ve been thirsty.”
“No, not really Daddy. You told me not to spill a single drop, so I’m trying to be a good girl for Daddy.”
“Hehehehe you silly girl, I was talking about the cum in your ass hole.”
“I know Daddy, but Cynthia Cockpig just wanted to be sure besides I’ve told you I’ll do whatever you tell me whatever Daddy wants.”
“That’s a good girl, Cynthia Baby, now you’d better have a proper shower. Daddy will see his slutty Cockpig Whore Cynthia Baby later.”
That night instead of doing his usual thing and slinking off to his bedroom after his shower Jerry powdered his hairless body then slipped into another Internet purchase, a sexy red and black see thru Baby Doll nightie. Jerry checked his make-up in the mirror and went to find his father. Doug was relaxing on his King size bed. Jerry crawled onto the bed and curled up against his father’s hairy barrel chest. Looking up through his reddish blonde fringe he put on the voice he had been practicing for weeks.
“Honey, can Cynthia be your bitch all holidays? Please Daddy, I will do whatever you say. I promise I’ll do what you want for all the holidays, Daddy.”
The last word rolled off his teenage tongue naturally, and Jerry was not worried about what his father would say because he had every intention of dressing as a girl all holidays anyway.
“Daddy would like to have his very own Cynthia Cockpig 24/7. Do you think you could keep up the required appearance for the whole two weeks of Cynthia?
It made Jerry feel much, much closer to his father now that they shared the same type of fantasies.
“Oh yes Daddy, I’m sure I’ll be able to do it. Can I please?
Whenever Jerry had been cross dressed, his father had not even refereed him as anything other than Cynthia that was until now.
“What’s this then? My sissy little fagot of a son wants to be his Daddy’s little Cockpig Whore, does he? Do you think you can live up to that special name Sissy fagot boy?”
Hearing his father talk like this amazed Jerry, the size of the tent growing in his tight black nylon panties left no doubt he was excited too. Jerry swallowed hard and looked up at his father. Doug’s wide smile gave Jerry some encouragement, batting his long eyelashes Jerry replied.
“Oh yes please Daddy I want to be your Cockpig Whore for more than a night. I love you, Daddy, and I cannot imagine anything better than being your real-life special girl. Here for your pleasure to use wherever, whenever and however you desire.”
“Well, if it was permanent you’d have to go on hormones because those fake tits are a poor substitute for a real pair.”
“Oh, can I? That would be incredible, Daddy. I would give anything to have my own pair of real tits. I’d do anything for my Daddy, anything he desires.”
“It’s the very least I expect from any personal Cockpig I’m looking to own 24/7 but if the whore can’t follow orders or look after me, I’ll throw her Tranny ass out in the street.”
Jerry did not miss the underlying hint in his father’s last statement and gulping in a few rapid breaths; He replied before he could stop himself.
“I’ll make a deal with you Daddy, I’ll gladly become your live in Transsexual Cynthia Cockpig and if I could go on hormones as soon as possible all the better. Legally that is once you have lived as a woman for an entire year, I cannot wait that long to have tits big enough for a boob job. I’ll do that if you let me become Cynthia Cockpig for real all I ask in return is that you find some way of getting me the pills earlier Daddy.”
“So, my sissy fag boy Jerry really wants to be a girl, does he?”
Jerry blushes brightly.
“Yes Daddy, I’d love to be a real girl, and big tits would make me feel ever so feminine. Hopefully, they will make my Daddy want his Cynthia Cockpig even more. Besides, all the clothes I have been buying are sized to fit me with a DD sized bust. It’d be fantastic to fill them out with real boobs instead of these fakies.”
Jerry cupped his fake tits and jiggled them up and down a few times.
“It’d cost me a pretty packet I bet.”
“I’d make it worth your while Daddy, just imagine what you could make your kinky little Cynthia Cockpig do. She’ll do whatever you desire.”
Doug slides his hand down over Jerry’s nylon covered clitty. Grasping his son’s hard clit through the thin material Doug slowly rolls his wrist this brings gasps of pleasure from Jerry’s throat.
“What about this Cynthia Cockpig?”
“Mmmmmmm aghhhh. Well, it would be up to my Daddy to decide. Wouldn’t it, but I’d rather keep it, if possible, Daddy.”
“Agh then you can’t be Cynthia then.”
“Oh, Daddy if that’s what it takes, I’ll do it for you.”
Doug’s hand tightened around his boys’ dick. “Why be so hasty Sissy Boy, watching you has brought out a different side to your Daddy, I’ve found out I like my girls to have a special clitty. Just because you cannot be Cynthia does not mean you cannot still be Daddy’s special girl. You just need a proper name Sissy Fagot Boy, just does not do it for me. If you’d been born a girl, your mother and I were going to call you Jennifer, so I think the perfect name for my new daughter is Jenny Cockpig.”
“So, it’s a deal Daddy? I will become your girl 24/7?”
“Yes, Baby Girl, that’s what I said. From this day forward your Daddy’s special girl you will never dress as a male again and you will take over every role that a woman would do. Every order I give is to be carried out without question. If you can please your Daddy, your outside life can carry on although you will have to be dressed up as a girl then as well. I do not want a Sissy Fagot Boy for a son, so Jerry is no more. Of course, Daddy will supply his daughter with a suitable allowance sufficient to purchase all manner of lingerie or clothing. You might as well make full use of whatever you find amongst your mother’s things too. I know there’s some great Latex, Lycra, and Leather gear that should fit.”
It did not really register what his father said Jerry was too excited about.
“What about my tits Daddy? When can I get my tits Daddy?”
“Leave it up to me, my little Cockpig daughter I’ll get them fast tracked because I can’t wait to tit fuck my sexy little Cockslut.”
Part two is in the pipeline, so I will post it soon.
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