“Shining... You really should take those off, she’s gonna be home any minute”, Night warned his effeminate son, who happily sauntered about the kitchen dressed in his mother’s panties and bra.
The girly boy had lost track of the time. Finally having the freedom to move about the entire house in girl’s clothes had kept Shining so pre-occupied, he forgot it was already Monday. He knew this experience would once again be limited to the stealthy dress-up sessions in his bedroom once his mom got back, but he didn’t want it to stop.
Shining bent himself over the kitchen table next to Night, sticking his cute tush out and pouting at his father. “Do I have to?”
Night smiled at his temporary wife and placed a had over Shining’s. “You don’t have to do anything, but you know as well as I do that your mother isn’t going to respond to seeing you dressed in her lingerie the same way I did.”
Shining frowned and stood back up. “Ok… but I’m keeping these”, he hollered back as he went into his bedroom to change.
Shining returned wearing basketball shorts and a T-Shirt, his normal walking around the house clothes. Sitting down next to his dad, the two waited for Twilight Velvet to return. While Shining ate his breakfast, Night noticed Shining had forgotten to remove his make-up, and the boy’s hair was still done up.
Not wanting to discourage Shining any further, Night didn’t say anything. He simply hoped his wife wouldn’t notice.
After about ten minutes, Twilight Velvet made it home. She walked inside and placed her bags on the ground before going into the kitchen to greet her husband and son.
“How are the two most important men in my life holding up without me?”, she asked.
Shining rolled his eyes at the cliché greeting, while Night smiled and responded, “just keeping ourselves entertained until you got back honey.”
“You two do anything special together while I was gone?”
“Ummm”, Shining and Night light looked at each other. Neither could think of a good lie with the truth being front and center in their minds.
“Nothing… really?”, Twilight asked. “Get dressed you two. If you two won’t do any boy things together when I’m gone, then we’re going to do some family things together right now.”
“Alright honey, where are we going?”, Night asked while his wife got her bags and took them to her bedroom.
“The mall”, she hollered out.
While she was unpacking, Twilight smelled something nasty. She looked around for the source and traced it to the bed-spread. Hesitantly, she gave it a sniff. “Ewwww… Night!”
Oh boy, “Yah honey?”
Twilight stuck her head out the bedroom door, “You know how to change the sheets, why does our bed stink so bad?”
“Sorry honey I was umm.. working out, and forgot to take a shower”, Night responded, hoping to Celestia that the lie would sell.
“Well I may have been gone, but that doesn’t give you permission to become a slob!”
“Sorry honey.”
“Hmph”, Twilight scoffed and returned to unpacking.
Night breathed a sigh of relief and looked to his son, “That was scary.”
“Yah”, shining chirped, and slowly stuck another bite of scrambled eggs in his mouth.
“You wanna go wash that stuff off your face before detective-mom in there whips out a blacklight?”
Shining looked at his dad confused, then stood up and made his way to the bathroom. Looking in the mirror, Shining saw he was still all done-up and quickly splashed some water on his face. Letting his hair down, he looked at himself once more and became sad.
Gone completely now was the cute mare he and his father so enjoyed, replaced by the disheveled young boy he had done so much to cover up.
Shining dried his face and made his way back to the table, depressed, thinking he would no longer be attractive to his dad.
As he sat back down, Shining felt a hand on his shoulder. “You ok Shiny?”
“I’m fine, it just sucks not being cute anymore”
Night squeezed his shoulder, “Hey, you were always adorable.”
“Really?”
“Definitely, the lingerie just the final straw for me.”
Shining perked up a bit, “You mean it?”
“If your mother wasn’t home, you’d be in there chewing on my pillow right now.”
Shining’s cock twitched at his fathers words. Placing his hands in his lap, Shining smiled, knowing his daddy still loved him.
At this point his mother exited the bedroom, ready to go to the mall. She looked at her husband and son grinning at each other and tilted her head. “What were you two talking about?”
“Boy things dear”, Night answered, with Shining nodding his head in agreement.
Twilight scoffed and smiled at the two before walking to the door. “Well let’s go then. I haven’t been shopping in months.”
Shining and Night rolled their heads as they got up to accompany Twilight on their “Family” trip.
{At The Mall}
“Alright Shining, me and your father are gonna be shopping together”, Twilight explained. Pulling a large bag of bits out of her purse, Twilight handed them to Shining and said, “You go buy whatever you want with this, just be sure meet me and your father back here at three o-clock, ok?”
“Ok mom.”
He watched his mom and dad take off toward some of the more thrifty stores in the west side of the mall. Not interested in artisanal coffee cups and the lot, Shining decided to make his way to the comic book store.
Walking inside, Shining eyed the many books that only days ago he would have given anything to have, but as he sifted through the adventures and tales of his favorite heros, he found that the excitement from reading them paled in comparison to the thrill he received from being fawned over.
“uggh”, Shining groaned placing the comic back on it’s shelf. “I don’t even care about this stuff anymore.”
Leaving the shop Shining wandered aimlessly through the mall, until he came to the front of a ‘de Lis’. His young mind was drawn to all the erotic undergarments and revealing attire within. Sub-consciously, Shining’s mind pulled him inside. Admiring all of the clothing he had only seen in the magazines he kept under his bed, Shining felt as though he were in heaven. (Que that goofy song)
As the entranced boy looked over the store’s wares, an assistant noticed him and assumed the worst. She approached the young boy and asked him what he was doing.
“This is a women’s clothing store young man. I don’t think you’ll find anything for you in here.”
Shining’s fogged brain interpreted her words more literally, rather than the subtle hint to leave that they were. Grabbing a pink tank top from the rack he held it over his chest and asked, “What about this?”
The store assistant was slightly perplexed at the boys response, until she noticed his long hair and the traces of foundation that dotted his face.
“We’ll I mean, that would look wonderful if you were just trying to hook-up with somepony for an evening.”
“Oh… ok”, Shining hooked the garment back on the rack and turned to the assistant. “What do ‘you’ think would look good on me?”
The assistant.. having her suspicion confirmed that this was not just another young boy being pervy, smiled and responded, “Depends, who are dressing up for?”
“My umm… daddy”, Shining answered shyly.
“Oh my!”, the assistant chuckled and grabbed Shining by his hand, leading him to the other side of the store where more fitting clothes could be found; and so the poor boy didn’t have to bee seen in a lingerie shop by every passer-by.
Stopping in front of a rack of unique outfits, the assistant sat Shining down outside a changing booth and asked, “So what does your daddy, like?”
“Umm, he likes it when I wear my moms leggings and underwear”, Shining barely managed to eek out from embarasment.
“Wait, so your daddy is your actual father?”
Shining nodded his head.
The assistant gasped and covered her mouth. She had no idea how deep this rabbit hole of an encounter was going to go.
Pulling herself together she put on a professional face, a small grin visible on the corner of her mouth. “Well love is love. Who am I to judge”, she remarked as she turned and grabbed a small, bright red bodycon dress from the rack. “I think this will strike a good balance between erotic and beautiful for your… partner.”
Shining took the dress and held it over himself in the mirror.
“Go on now, try it on”, The assistant insisted, putting a hand on Shining’s back and nudging him into the changing room.
Once inside Shining eagerly removed his basketball shorts and shirt. Sliding the dress on he was amazed at how perfectly the off-the-rack piece fit him. It accented his slender body so perfectly, he could have passed with it alone, but the assistant had other plans.
As the young boy emerged from the changing room, she quickly took him by the hand and led him into the back, where another worker sat smoking a cigarette.
“Who’s this cute… wait”, the other worker walked up to Shining and eyed him up. “Is this a boy or a girl?”
“Boy Sequin”, the assistant answered, motioning for Shining to sit down in the chair. “I want you to work some of your magic on him.”
Sequin looked at the femcolt sitting in the chair and turned to her friend. “He looks perfect as is, but whatever. He’ll be the belle of the ball when I’m done.”
“Umm, what are we doing?”, Shining asked.
“Your make-up pretty boy”, Sequin then turned back to the assistant. “He’s a light job, give me like ten minutes.”
{Ten Minutes Later}
The assistant returned with a pair of adorable sneakers for Shining, only to find he was gone, and in his place… was a princess.
Oh my Celestia, he’s perfect!, The assistant thought as she set the shoes down beside him, and admired the great work Sequin had done.
Shining’s face was done up in such a way so as to leave no indication what she was looking at was ever a male. Light rouge tinted his cheeks, and his hair had been done up in a long flowing pony-tail, with symmetrical bangs lining the sides of his face, and his nails had been given a coat of sapphire nail polish.
His lips had been coated in thin layer of similarly colored gloss, and a light helping of mascara made his beautiful, ocean-blue eyes pop like nothing else. All of this had been done in ten minutes with Sequins trademark minimal make-up mentality. The assistant could only imagine how pretty this boy could be if she were forced to go all out on him.
Sequin spun Shining to the mirror, and the two watched as his face light up like a toddler looking at a shiny new bicycle under the Christmas tree.
“Oh,my… I-I look sooo”, Shining sniffled.
“No crying! you’ll ruin my work”, Sequin ordered.
“I’m sorry I just… I never thought I could look this pretty”, Shining replied as he admired the girl in the mirror.
“Let’s get you a few more things, and then well send you off”, the assistant helped Shining from the chair and walked him back into the front. After getting him fitted in his new shoes, she handed him a small bag.
“What’s this?”, Shining asked.
“Some additional items I think will make your partner smile.”
Looking in the bag, Shining found a set of nylons, a pair of four inch heels, a matching pink bra and panties, a bottle of lube, and last but most certainly not least...
A chastity cage.
Shining blushed, quickly closing up the bag and looking around. “Thank you so much, miss?”
“Rarity” she replied. “I plan on someday opening my own boutique, but so long as I’m here, you feel free to drop by anytime cutie.”
“How much money is all this going to cost?”, Shining asked as he pulled out his bag of bits.
“Keep your bits darling. I’m just happy I got to bring out the true beauty in somepony today. That’s what I live for.”
“Thank you!”, Shining hugged Rarity and ran out of the store to meet back up with his parents.
{At The Mall Entrance}
Shining sat on a bench. Both eagerly and fearfully awaiting his parents return and subsequent reaction to his appearance. He didn’t know what his mom would think, and that was his main concern.
But judging from many lustful gazes of stallions passing by, some of whom were even with their marefriends, he knew his dad was going to love it.
As three O-clock approached, Shining seen his parents coming over.Alright, this is it.
Or was it?
Shining was slightly confused when his parents walked right by him and sat down on the bench to his right. He watched them place their bags on the ground by their feet, and listened to them talk to each other.
“Where do you think he’s at honey?”
“He’s probably still shopping for comic books or swords or something. I’m sure he’ll show up before to much longer.”
Oh my freaking…, Shining gasped. They don’t recognize me!
Turning to face away from his parents he wondered what to do now. Should I leave and go change? No, no it’s too late for that. Maybe I could..
“Shining? Is that you?”, Twilight asked the cute mare sitting across from her. Getting up she walked in front of the girl and asked again. “Shining?”
“Hi mom”, he answered.
While Shining tried to turtle inside himself, Night piped up, “Shining you look… amazing!”
“Thanks dad.”
“Night that’s your son!”
“You know what I meant honey, I mean look at her!”
“HER?”, Twilight’s brain was running a million miles a minute as she tried to understand what her son had done to himself. “Shining, why are you dressed like… this!?”
Shining took a deep breath. “I.. I wanted to be pretty, like you mom.”
“Well you got that in spades”, Night added.
Twilight glared angrily at her husband before returning her attention to her son.
“Do you like it mom?”
“Yah honey, tell the boy what you think.”
Twilight Velvet honestly had no idea what to think. On the one hand her son did look beautiful, more beautiful than her even… though she would never admit it; and on the other he was still her son. She had no idea how to handle this situation.
“I, umm?”
“You hate me now don’t you!”, Shining wailed as he buried his face in his palms.
“NO! I just…”, Twilight looked to her husband, who stared back at her expecting she do the right thing. Twilight slowly knelt down, took her son’s hands, and held them tight.
“You look amazing Shining.”
“Really… you like it?”
“Well I’m not a fan of leaving your father with another pretty mare in the house, but if you like to look this way, I support you. Now let’s go home.” Shining smiled. Getting up off the bench, he grabbed his bag.
After his parents had gathered up theirs the three exited the mall… and went home.
{Back At The House}
Shining sat on his bed with his bag of goodies. Now that the cat was out of the bag so to speak, at least with regard to the cross-dressing; Shining felt comfortable trying all his new clothes on.
Shining kicked off his sneakers and pulled out the heels. Before putting them on however, he pulled off his boxers in exchange for the panties and bra that Rarity had so generously given him.
Then,after sliding the pantyhose up his hairless, slender legs, Shining slipped his little feet into the dark red heels, leaving only two items in the bag.
The chastity cage… and the lube.
Shining deeply wanted to give his dad the key to that cage, but was unsure if right after coming out to his mom would be the right time to be gifting him that.
Whether he gave him the key or not however, Shining was going to lock himself up.
Inspecting the cage, Shining easily figured out how it was supposed to work. He layed himself out on the bed, yanked down his panties and nylons, before wrapping the base ring tightly around his package.
He then grabbed she second piece and worked it over his tiny cock. Forcefully pressing the flattened cage down in line with the locking mechanism, Shining stuck the key inside, gave it a turn, and that was it.
Shining’s cock was now off limits… at least he felt that way. It wouldn’t be official until he gave his dad the key. Pulling his underwear and nylons back up, Shining stuffed the key into his panties, and walked into the kitchen for dinner.
Sitting there, Shining immediately noticed his mother glancing at him. He knew she was still troubled by seeing her son in a dress, but hoped she would get used to it.
Night Light meanwhile, was outright staring at him. The guy was basically drooling over him with his wife standing right there making dinner.
Shining appreciated his dad’s attention, and so decided to tease him a little by seductively bitting his newly painted fingernails.
This caused Night to bite his lower lip and pull his seat closer to the table, hoping to hide his raging erection from Twilight. He didn’t want his wife seeing him hard for their son and ruining dinner.
Maybe he could play it off like it was for her, but Twilight Velvet would see right through any lie about how attractive she was, especially given the only sexy thing she was wearing at the moment was an apron. An item that didn’t go very well with sweatpants and emotional stress.
Once Twilight had finished cooking she placed their meals in front of them before making a plate for herself and sitting down.
The three sat in total silence as they ate for a full five minutes before Night broke the ice by asking Twilight how she was taking everything.
“You feeling ok honey?”, Night asked, stuffing a fork full of green-bean casserole in his mouth.
“I’m fine. I’m just trying to figure out how after one weekend alone with you, my son becomes a girl.”
As his wife rubbed her head, Night thought hard about what he should say to her, but decided the best thing to do was to remain silent.
After a moment Twilight got up. “I need some air”, She said before walking outside.
Night looked at Shining, who hung his head feeling bad about the whole affair. “Don’t worry Shiny, she’ll come around.”
“I know. I think she’s just weirded out, I would be to.”
Night nodded his head, “yah, I hope that’s all it is.”
“What do you mean?”
“She’s seen her clothes going missing for a long time now. She always suspected it was you masturbating or something, or maybe that’s what she hoped. I think seeing you like this just confirmed what she already knew.”
“Am I still ok to dress like this now?”
“Of course. It’s just going to take her awhile to get used to it.” Night reached across the table and lifted Shining’s chin up. “I like you like this, and I think given time, your mother will to.”
“Ok dad.”
Outside the door, Twilight heard every word of their conversation, but luckily didn’t see when the two locked lips with each other. Shining broke off the kiss and quickly reached into his panties.
He pulled out the chastity key and slid it across the table to his dad, “I want you to have this.”
Night looked at it for a moment. He recognized the key by it’s size and where it came from, but just to be sure he asked. “Is this what I think it is?”
Shining nodded and fidgeted in his seat, feeling super horny knowing his dad now owned his little prick.
An evil grin moved across Night’s face, and he tossed the key into a trash can across the room.
“Dad! Why?”
Night got up and walked over to Shining, a massive bulge visible in his pants. “You wanna be daddy’s little girl, then you gotta go all in.”
Shining gulped as his father leaned down and placed a kiss on his lips. He then pulled away, and smiled lovingly at his Shiny. “Now, go wash the dishes for your mother.”
Twilight heard the chastising, and in her naiveté assumed Night was punishing the boy for something. While she was happy to not be doing the dishes tonight, she wondered what exactly Shining had gotten ahold of to get him in trouble.
Walking back inside she seen Shining running the water for the dishes, and decided to wait until he was out of the kitchen to go digging around in the trash. She then made her way to her bedroom, where she found her husband lying butt-naked on the bed, with his cock pointing at the sky.
“Well well, somepony missed me”, Twilight joked as she shut and locked the door behind her.
“More than I’ll ever admit baby”, Night slowly stroked himself and fondled his giant nuts, as he watched his wife sensually strip down in front of him.
Climbing onto the bed, Twilight threw a leg over Night and positioned herself over his enormous cock, which was still a bit intimidating even to her.
Spreading her knees Twilight gently lowered herself onto it, and began applying pressure. Thankfully not much was needed before the flared head popped inside.
“Oh baby”, she gasped as she shifted her hips, taking some more of her husbands meat into herself.
As his wife continued her painfully slow decent into his lap, Night became impatient and thrusted upward.
Twilight’s eyes went wide as the tip of his cock poked against her cervix, and she fell all the way down to the base of his shaft.
Placing her hands on Night’s chest, Twilight lifted herself up before slapping him in the face. “You wanna be rough, so will I!”
Shining sat up.
Leaning back on his arms he smiled and wiggled his cock around inside her. “Fine by me baby.”
Launching himself forward, Night locked lips Twilight as he rolled the horny milf into a mating press. While pounding away at her, she nibbled on his ear and clawed at his back, encouraging the strong stallion to fuck harder.
Twilight’s primal emotions were causing loss of breath. She layed back with her mouth hanging open, as Night gave his all to make up for lost time.
She came for the first time as Night reached under her legs… around her body, and gripped her tight. She was only half aware of what Night was doing when he hoisted her entire body into the air.
Her ankles by her ears, Twilight looked down to see her husband’s cock making quick full-length thrusts into her pussy. The mere sight of which brought the sex starved mare a much deserved second orgasm.
Night was happy he could still please his wife in such an important way, however his own desire for pleasure was rapidly taking over. Slamming Twilight against his groin, Night locked lips with her once more. They sloppily made out while the strong stallion continued his assault for another two minutes, then…
Night clenched, his balls contracted, and he unloaded rope after rope of his warm seed into his beautiful wife.
Twilight moaned with each pulse, loving the way her husband fucked. It was as though they were trying to have another kid, something she would gladly do should Night only ask.
Meanwhile, her current kid was listening through the door. Shining heard every grunt and moan of pleasure his parents made as they went at each other like animals. Unfortunately with his cock caged, the poor boy was denied the ability to pleasure himself, and the raw desire to free his cock and jerk it right then and there was almost overpowering… almost.
Pulling his hand out of his panties, Shining returned to doing the dishes, hoping the chore might distract him from the fact that his dad was plowing his mom just feet away.
After a few minutes the bedroom door swung open, and Night stepped out, leaving Shining’s exhausted mother to lay leaking hot cum onto the, luckily still dirty sheets.
As Shining finished up putting away the dishes, he felt his naked father step behind him. He closed his eyes as his dad ran his hands up and down his hips.
Night leaned down and whispered, “You want a turn to, don’t you baby?”
A gasped escaped Shining, and he almost dropped the glass he was putting away. “Yes”, he moaned, pressing his satin covered ass against his fathers still rock hard horse-cock.
Post-nut clarity seemed to have zero effect on Night’s love for the boy… either that or he was just super horny.
“One sec”, Shining blurted, and ran to his bedroom to grab the bottle of lube, but when he turned to go back, his dad was standing in the doorway. Shining was a little confused. The prospect of another wonderful night with his father clouded his mind, so when his dad walked over and picked him up, Shining didn’t question it.
Lifting him up, Night carried his substitute spouse down the hall, and into HIS bedroom.
Twilight was on the bed, half asleep as Night layed Shining next to her. While Night shut and locked the bedroom door, Shining pulled off his heels and set them down at the end of the bed.
When his dad came back he whispered, “What about mom?”
“Yah, about that…”
To Shining’s horror, his dad reached over him and shook Twilight awake. “Hey honey we need to tell you something”, Night said aloud.
Twilight slowly opened her eyes to see Night maneuvering her son into a doggy style position. With his face down on the pillow, Shining looked to his now awake mother, and put on an uneasy smile.
“It might make you happy to know that our little Shiny here doesn’t just want to be a girl”, Pulling down Shining’s pantyhose and underwear, Night went on. “He wants something even better.” Popping open the bottle of lube Shining had brought, Night prepared his cock before dropping the bombshell.
“W-What?”, Twilight’s brain tried, and failed to process the images that her eyes were seeing. She almost lost it when Night hot-dogged his cock between Shining’s cheeks.
He then used some more of the lube on himself before shoving the bottle in Shining’s ass and squirting the remainder in there.“What she wants honey… is to be my wife.”
Night slipped the tip of his cock inside Shining, and let his tight hole clench around it for a moment while he watched Twilight’s jaw fall open.
“Gu-ug… he… you”, she babbled as she watched her husband slide his cock into what was her little boy.
“Yes… deeper daddy”, Shining moaned.
“Yah, there you go. Tell mommy how much you like daddy’s cock in your ass.”
Shining looked at his mother. “I love it so much… ooohh”, Shining moaned as Night bottomed out in him.
“So honey, think you can share?”, Night asked with his son’s cute little ass fully wrapped around his cock.
Something in Twilight’s head snapped, and big smile crossed her face. She reached over and squeezed her son’s hand, “All I ever wanted was for you to find a beautiful wife someday. If what you want to be one instead, even if it’s your father’s well… Ok”
Shining squeezed her hand back, as his father gently fucked him. Having gotten his mother’s blessing, Shining began rocking himself back and forth in time with Night’s thrusts.
“ooooh… good girl”, Night breathed, giving Shining a smack on the ass.
“Mhnnnn!”, Shining yelled into the pillow as his father grasped him by the hips, deciding hard and fast was the better route in this situation.
Twilight watched her husband’s face contort and his thrusts become more sporadic. After being with the man for years she could easily spot the telltale signs of his approaching climax.
“He’s close baby, he’s gonna fill you up!”, She warned Shining, who buried his face in the pillow to muffle the girly sounds he was making.
Taking shallow breaths, Night continued pounding away. As he did so he felt his son's ass clenching around his shaft.
Looking down, he seen the boys caged member leaking a pitifully small ammount of cum. The sight of this stroked Night’s ego. Making a mare and stallion both cum in the same evening had the masculine father feeling pretty proud of himself.
A emotion that translated rather well when he suddenly grunted and held Shining in place, giving the femcolt the creampie of his life.
His wife rubbing her cum stained pussy while she observed the base of Night’s cock as it throbbed, pumping her son full of the same seed that had once conceived him.
She watched Shining’s belly round out against his dress from volume of cum filling him. Hearing her son weakly moaning into the pillow, she wondered if he would be able to take it all.
She was going to ask Night to pull out, but when she saw the blissful smile on Shining’s face she decided it best to let her husband finish breeding his new wife.
As Twilight’s mind tried to cope with this new reality, she wondered aloud, “What kind of wife will you be Shining?”
Shining mumbled something about love and sex into the pillow before collapsing onto the bed, pulling Night’s cock free of his ass as he did.
Once the last of Night’s cock was out of Shining, his abused rear clenched tight, sealing the entirety of his fathers load inside.
“Dad”, shining moaned as he rolled himself onto his back. “Can I sleep in here tonight?”
Laying himself beside Shining, Night ran a hand along his nylon covered thighs. Shining pulled the fabric over his caged member and rubbed along with him, and once his clingy red dress was back down over his legs Shining looked at his father expectantly.
Night pulled the boy close while Twilight scooched over, sandviching the new girl between them. Then Night gave him a final kiss before answering the question…
“Your sleeping here every night”
