Training Daddy

This is a fictional story. All the names, places, and situations have been made up.

No characters are under the age of eighteen (18).

Comments and Rating always Welcome!

David is staring out of his office door, unable to concentrate on work, when he sees Tony walk by. Deciding he's not going to get anything done, David decides to see if Tony is going to his office. When he gets there the door is open, and Tony is at his desk looking over some paperwork. David knocks on the door frame. "Hey."

Tony looks up and smiles. "David, come in." He stands and quickly walks over to David, putting his hand gently on the small of his back and nudging him further into the office. "Have a seat." He closes the door.

David sits in one of the chairs in front of Tonys desk. "I hope I'm not interrupting anything."

Tony sits in his chair, behind the desk. "I was just looking over a proposal, nothing that can't wait." He closes the folder and pushes it to the side. "I wasn't sure you were still talking to me."

David crosses his legs. "Neither was I, I'm still mad at you." He takes a deep breath. "But you are my best friend."

Tony looks at him, surprised. "Your best friend?"

David pretends to brush something off his pant leg. "Don't get too excited, I don't have many friends."

Tony studies David before speaking. "I'm sorry that I made you mad, but I'm not sorry for what happened."

David crosses his arms. "How can you say you're not sorry for what happened!" He lowers his voce to make sure he's not heard outside the room. "I didn't want to give you a blowjob...you forced me to."

Tony comes around the desk and sits in the other chair. "David...maybe you don't know it, but you've always been a cute guy." He hesitates. "Hell, even sexy." He leans forward and puts his elbows on the arms of the chair. "And now you've let your hair grow out and you're more feminine than before. It just got the better of me, please understand."

David looks around the room, then back at Tony. "A lot of guys grow their hair long, and I don't act any more feminine."

Tony smiles. "I didn't say you ACTED more feminine..." He nods in the direction of Davids legs. "...I said you ARE more feminine."

David looks down at his leg. He's embarrassed to find they're crossed like a woman would cross them, and the top leg is swaying back and forth. "That doesn't mean anything." He uncrosses his legs. "I better get back to my, I have some calls to make."

When David stands, Tony stands with him and walks him to the door.

When they get to the door Tony puts his hand on the knob, but hesitates opening the door. "I'm glad we're still friends."

David smiles nervously. "Me too."

Tony opens the door for David to leave.

After finishing his last phone call David looks at his watch and sees it's a couple minutes past time to leave. He grabs his things and rushes to his car.

Getting home seemed to take forever due to an accident. When David does get home either the house is empty, or Claire is staying with Jeff at his dads house, or Claire, and maybe Jeff too, is asleep up in her room. David really doesn't care and goes directly to his bedroom, and to bed.

In the morning David crepes upstairs to Claires room. Happy to find the room empty, he has a leisurely breakfast then goes to run several errands. When he returns home he cane can hear Claire up in her room talking on her phone, and goes to his bedroom for a shower and change of clothes..

When he gets to his room there is a blouse, skirt, purse, wedge type shoes, and a couple bags on his bed.

Behind him, Claire walks into the room. "Finally, you're home. I was afraid you wouldn't have time to get ready for your date tonight."

David turns. "Date?! What date?!"

She walks to the bed and sits next to the dress. "It was a last minute thing." She leans back, resting her hands on the bed. "Jeffs dad is going to a party at a private club he belongs to, and his date cancelled at the last minute." She smiles. "So, you will be his date tonight."

David can feel his face turning red, and his anger level rising. "NO! I'm not going to some damn private club with someone I don't know, and definitely not going dressed as a woman!"

His daughter stands, grabs the bags and empties them onto the bed. "I got you a couple razors, a bra and panties, and a larger plug." She spreads them out. "Luckily we're pretty much the same size..." She giggles. "...other than cup size, I have you beat there."

David shakes his head. "Didn't you hear me...I'm not going!"

Claire takes a deep breath then turns around to face him, her face tight. "Listen. You are going to this party with Jeffs dad, because if you don't I'll send those pictures to your work email, go live with Jeff and his dad, and watch you lose your job and everything else." She takes a minute to calm herself. "Jeff told me you won't be the only crossdresser there, so don't worry about being the only one."

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

For a brief moment their eyes meet and David thinks about refusing, no matter the outcome, but decides against it. He drops his pants and underwear and bends over, his hands on the bed.

Claire slides her hand over his back, her voice much softer. "Spread your pussy, daddy."

He reaches back, putting a hand on each of his cheeks, and pulls them apart.

His daughter pushes down on his back with the one hand, her other hand wriggling the plug as she forces it into his pussy. "I'll take this out before you leave."

David closes his eyes, his body tense as the plug slowly penetrates his pussy. His toes curled inside his shoes. When the plug has been fully inserted, and his muscles close around the thinner section at the base, he opens his eyes and takes a breath. He stands when Claire takes her hand off his back.

She picks up the electric razor she bought him. "The other razor is for your legs. This one has lots of attachments for shaving the rest of your body." She shoves the box at him, making him take it. "It even has an attachment for your balls and around your clitty." She walks to the door. "Luckly you don't have much body hair, so it shouldn't take too long." She studies him. "Don't forget to shave your pits, and your face, to get rid of any five-o'clock-shadow. Come find me when you're dressed." She goes into the hallway.

David is almost ready to cry, but fights back the feeling. Reading the instructions for the razors, he discovers they can be used in the shower, and realizes Claire hadn't gone cheap, purchasing quality products. He starts by shaving his legs, the razor easily following the curve of his skin. Nervously he shaves around his clitty, surprised at how easy it is with the high quality razor. He finishes by changing to a different attachment and shaving his arm pits. Looking over his arms and body, he realizes Claire was right, he didn't have any other body hair, other than fine hairs on his arms that aren't worth dealing with. After drying off, he uses his regular razor to shave his face. Turning around and looking over his shoulder into the mirror, he's pleased to find he doesn't have any back hair.

When he goes back into his bedroom Claire is sitting on the bed. "Jeff is in the living room with his dad, so I thought I'd wait here so I could take the plug out, before you got dressed.

David bends forward and pulls his cheeks apart, his voice sharp. "Why even put it in, if you're just going to take it right out?"

She pulls the plug free. "It'll make easier on you when you get fucked, having your pussy already stretched."

David turns and glares at his daughter. "I'm not getting fucked tonight!"

Claire walks up to David. "That is not a decision for you to make." She takes a step closer, her face inches from his. "You are Emersons bitch tonight."

She walks into the bathroom, fills the sink with soapy water, and puts the plug in. "We'll be in the living room, when you're ready."

David watches his daughter go into the hallway, and whispers to himself. "What kind of a name is Emerson?"

He picks up the red bra and tries it on. The way it hugs his body, without leaving gaps, makes him smile. When he picks up the package of panties he finds it's a group of three, made of a sheer material, in white, black, and red. When he notices a large section of the panty that would cover his pussy is missing he's horrified. When he looks over the packaging he discovers they're 'assless'. Nervously he puts them on, easily tucking his tiny clitty, which leaves very little bulge.

The white blouse is sheer and sleeveless, with black trim around the collar, arm holes, and hem. The skirt is black, knee length, with a deep slit up the right side. When he moves he can feel the material sliding over his cheeks, where they are exposed by the 'assless' panties.

Holding onto the beds post, he puts on the wedge shoes, red cloth on top and black soles. He picks up the tiny red purse, pulling the small gold chain over his shoulder, and looks at himself in his full length mirror. Lastly, he shakes his head, and runs his fingers through his hair. In the back of his mind he wishes he'd gotten his hair styled.

Turning from side to side, he's excited to see his red bra visible underneath the blouse and the way the slit in the skirt shows more leg with each movement.

"Wow! You look great."

David quickly turns, seeing Jeff in the doorway. "Thanks...I guess."

Jeff walks into the room. "Claire asked me to check on you. My dads really anxious to meet you."

David nods, and holds up the purse. "I don't know what to do with this, it's so small."

Jeff takes the purse and grabs Davids wallet off his dresser. He takes out his drivers license and some one dollar bills, and puts them in the purse. Then he reaches into his pocket and pulls out some condoms and a tube of lip gloss. He puts the condoms into the purse, then hands it and the lip gloss to David. "Do your lips, then put the tube into your purse." Before walking into the hall, he turns and smiles. "By the way, you're not David anymore. Now you're Davie." He heads to the living room.

Davie puts on some lip gloss, puts the tube into the purse, and checks himself in the mirror again.

In the living room Claire, Jeff, and Emerson are sitting and talking. As soon as Jeffs father sees Davie he stands and smiles.

Claire and Jeff stand.

Claire introduces them. "Emerson, this is Davie."

Davie is impressed by his date. Emerson, is 6'0", with short black hair and a goatee, with a hint of gray. Although he's older than Davie, he appears to have a nice body under his clothing. Emerson is wearing a black suit with a white shirt and black tie.

Davie holds out his hand. "It's nice to meet you."

Emerson takes Davies hand and gently holds it. "The pleasure is all mine." He lets go of Davies hand." He turns to Claire and Jeff. "We better go." He picks up a coat that Claire had obviously laid over the back of the couch, and holds it open for Davie.

Davie walks into the coat, letting Emerson put it onto his shoulders. "I won't keep Davie out too late."

Claire giggles. "Whenever, he's all yours tonight."

Davie glares at Claire, not sure he likes what she implied.

Emersons car is a luxury sedan. He opens the passenger door for Davie, then closing it once he's inside. After sliding into the drivers seat Emerson turns to Davie. "You really do look beautiful tonight."

Davie blushes. "Thank you, that's very kind to say." When he glances at Emerson, he notices the man looking at his legs. When Davie looks down he sees that because of the slit, his skirt as fallen between his legs, leaving his right leg exposed. For a second he thinks about pulling the skirt back over his leg to cover it, then decides he likes that Emerson was paying him that kind of attention. He leaves his leg uncovered and turns to his date. "I must admit, this is the first time I've gone anywhere dressed in womans things."

Emerson turns to Davie and puts his hand on Davies thigh. "No one would ever guess that." He takes his hand back, and starts the drive to the club.