Group Sex

Daddy Training: Chapter 4

David transforms into a female persona, called Davie.

Spankmasters
May 23, 2024
7 min read
daddydaughtergaycrossdressercdTraining Daddy Ch. 04
Training Daddy Ch. 04
Training Daddy Ch. 04

Daddy Training: Chapter 4

Imagination alone spawns this story. All the characters and places herein are figments of imagination.

There are no minors in this narrative.

Your feedback is appreciated!

David stared out of his office door, his focus disintegrating as a familiar face passed by. Unable to focus on his work any longer, David resolved to approach him. Finding his door open, David stepped into the room to find Tony sitting at his desk, browsing through some documents. "Hey," David greeted.

Tony greeted back, visibly surprised, "Hi. Come in." He swiftly got up and walked over to David, gently pushing him towards a vacant chair before shutting the door.

David sat in the given seat. "I hope I'm not interrupting anything important."

Tony didn't seem to care; he sat back in his own chair behind the desk. "I was just taking a look at a proposal. Nothing that can't wait." He sidetracked the folder beside him. "I wasn't sure if you still spoke to me."

David crossed his legs. "You know you're still my best friend."

Tony raised an eyebrow, "Your best friend?"

David acted cavalier, "Don't get excited. I don't have many friends."

Tony studied David's demeanor before responding. "I'm sorry I made you angry, but I'm not sorry for what occurred."

David crossed his arms. "You can't tell me you're not sorry what transpired!" He lowered his voice to prevent any outside interruptions. "I didn't want to give you a BJ... you forced me to."

Tony stepped around the desk and sat in the open chair. "David...maybe you don't realize it, but you've always been an attractive guy. Hell, even sexy. Especially now that you've let your hair grow long...you look more feminine. That's all."

David examined his legs; both of them crossed like a woman would. "That doesn't mean anything." He uncrossed his legs. "I need to get back to work."

When David stood, Tony followed him to the door.

At the end of his shift, David checked his watch: his relationship with Claire and Jeff were pending, so he decided to return home. His entrance was met with either an empty house, Claire with Jeff at Jeff's dad's house, or Claire asleep on her bed. David didn't care and made his way to his room for a shower and a change of clothes.

After finishing his shower and dressing, David traipsed downstairs to find piles of clothing on his bed: a blouse, skirt, purse, shoes, and a few bags. Behind him, his daughter Claire appeared. "At last, you're home. I was worried you'd be late getting ready."

David turned. "Late for what?!"

Claire approached the bed and sat down, her fingers dancing amongst the items. "It's a last minute plan. Jeff's father is attending a party at his exclusive club tonight, and his date canceled at the last minute." She beamed. "So, you'll be Jeff's date."

David's face flushed; his temper rose. "Absolutely not! I refuse to enter some damned private club with someone I don't know—let alone dressed as a woman."

Claire grabbed a couple razors, a bra, panties, a bigger plug, and placed these things on the bed. "I bought you these things," she stated. "Luckily we're pretty much the same size...save for cup size." She chuckled. "You'll look amazing."

David shook his head. "Listening closely, I heard no, 'Yes, please.'"

Brenda deep breathes, turning to face her father. "Listen. You are attending the party with Jeff's dad, or else I'll send those photos of you dressed up to your work email, stay with Jeff and his father, and watch you lose your job and everything else." She takes a minute to calm herself. "Jeff said you won't be the only crossdresser there, so don't worry too much about being the only one."

She picks up the small box, opens it, and pulls out the plug. "Pull down your pants and bend over."

For a moment, their eyes meet and while he briefly considered refusing, he decided against it. He complied, dropping his pants and underwear, then bending over, hands on the bed.

Brenda gentle runs her hand over his back, her tone much softer. "Spread your vagina, daddy."

He reaches back, placing a hand on each of his cheeks, and stretches them apart.

Her daughter pushes down on his back with one hand, her other hand wriggling the plug as she inserts it into his vagina. "I'll remove this before you leave."

Brenda's eyes are on her father while his body tensed, his toes curled inside his shoes. Once the plug was fully in place, and his muscles squeezed the thicker section at the base, he opened his eyes and took a deep breath. He stood when she released his back.

She picked up the electric razor she bought him. "The other razor is for your legs. This one has multiple attachments for shaving the rest of your body." She shoves the box at him. "This one even has an attachment for your balls and around your clitoris." She exits, heading down the hallway.

Brad was this close to breaking down, but managed to control it. Reading the instructions for the razors, he found they could be used in the shower, and realized her mother hadn't spared any expenses, buying quality products. He began by shaving his legs, the razor easily gliding along his curves. Uneasily, he shaved around his clitoris, surprised at how simple it was with the close form-fitting razor. He finished by changing to a different attachment and shaved his armpits. Looking over his arms and body, he realized she was right - he had little body hair aside from fine hairs on his arms that weren't worth fussing with. After drying off, he used his regular razor for his face. Turning around and facing the mirror, he was happy to find he had no back hair.

When he walked back into his bedroom, Brenda was sitting on the bed. "Jeff and his father are in the living room, so I'm waiting here to remove the plug before you get dressed."

David bent over, pulling his cheeks apart, his voice sharp. "Why bother putting it in then?"

She retrieved the plug from the sink then walked back in. "It'll make it easier on you when you're fucked, having your vagina already stretched out."

David glared at his daughter. "I'm not being fucked tonight!"

Brenda stalked up to David. "That's not a decision for you to make." She stepped even closer, her face inches from his. "You're Emerson's for tonight."

She strode into the bathroom, filled the sink with soapy water, and placed the plug back in. "We'll be in the living room when you're ready."

David sighed, whispering to himself, "What kind of a name is Emerson?"

He tried on the red bra, watching it hug his body, creating no gaps, making him smile. The package of panties contained three, made of a sheer material, in white, black, and red. When he noticed the large part of the panty designed to cover his vagina was missing, he was appalled. When he examined the packaging, he discovered they're 'assless'. Nervously, he wore them, able to easily tuck his tiny clitoris, which left only a small bulge.

The white blouse was sheer and sleeveless with black edges on the collar, arm holes, and hem. The skirt was black, knee-length with a deep slit up the right side. When he moved, he felt the material slip over his cheeks, covered by the 'assless' panties.

Gripping the beds post, he put on the red high-heeled shoes, the top part in red and the soles in black. He picked up the tiny red purse, slinging the small gold chain over his shoulder, and gazed at himself in the full-length mirror. Finally, he shook his head and ran his fingers through his hair. In the back of his mind, he wished he'd gotten his hair styled.

Swinging his hips, he inspected his red bra beneath the blouse and how the slit in the skirt revealed more leg with each movement.

"Wow! You look fantastic."

David glances over and spots Jeff entering the room. "Thanks, I suppose."

Jeff strolls inside, "Claire asked me to check on you. Her dad's seriously looking forward to meeting you."

David indicates the small purse in his hand. "I'm not sure what to do with this thing."

Jeff takes the purse from David and grabs his wallet off the dresser. He stuffs his driver's license and a few dollar bills in the purse. Then he retrieves some condoms and a tube of lip gloss from his pocket. He places the condoms in the purse, then passes the gloss and the purse to David. "Add some color to those lips, and then toss that tube into your bag." Jeff strides toward the hallway.

David applies some lip gloss, packs the tube, and once again assesses his appearance.

In the living room, Claire, Jeff, and Emerson are chatting. Jeff's dad, Emerson, rises as soon as he spots Davie.

Claire and Jeff rise as well.

Claire introduces them, "Emerson, meet Davie."

Davie studies Emerson, who stands 6'0" tall, with short black hair and a goatee, sporting a hint of gray. He appears to have a well-sculpted body under his clothing. Emerson is adorned in a black suit, white shirt, and black tie.

Davie extends his hand, "Nice to meet you."

Emerson accepts Davie's hand and gently holds it. "The pleasure is all mine." He lets go of Davie's hand, then approaches his friends, "We should be going." He grabs Claire's coat, which she must've draped over the back of the couch for Davie, and helps Davie slip into it. "I won't keep Davie out too late."

Claire snickers, "Whenever you're ready, he's all yours tonight."

Davie regards Claire with a frown, uncertain of her suggestion.

Emerson's vehicle is a luxury sedan. He opens the passenger door for David, closes it once he's settled inside, and slides behind the wheel. "You do look quite radiant tonight."

David blushes, "I appreciate your compliments." Catching a glance at Emerson, he notices the man gazing at his legs. He studies his own legs and notices his skirt has slipped, revealing his right leg's bareness. For a moment, Davie contemplates restoring the dress's modesty; then he thinks better of it, relishing Emerson's close scrutiny. He leaves his leg exposed. He turns his attention to Emerson, "It's my first time going out dressed as a woman."

Emerson shifts in his seat, directing his hand to Davie's thigh and stroking it. "No one could ever imagine it, you look so convincing." He removes his hand, and drives toward the club.

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