Made Up

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A budding crossdresser meets with an experienced trans woman.
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My first story on Literotica! Hope you like x

*****

For the longest time, I've crossdressed alone. I taught myself how to climb into girly clothes, how to roll on tights without tearing them, how to put on my wig without it looking like roadkill. It took time, but I slowly learned how to get myself ready to enter girl mode. But there's a few things I've never been able to do;

1) I've never been able to put on make-up

2) I've never felt fully confident as my alter-ego, Danni

3) I've never been fucked as Danni.

Last night I managed to tick off all 3 of these things, all in one go. This is that story.

It started when I was contacted by a local dresser on my online casual dating profile. We got to chatting and hit it off instantly; although I basically spent 3 hours gushing over her pictures. She was immaculate! Not too drag, not too underwhelming, she was H.O.T. She was experienced in the art of the transformation, and while she wasn't interested in playing, she saw promise in me. She wanted me to be her pet project. I jumped at the opportunity! I packed a humble bag of embarrassing little pieces of clothing; I'd rather turn up with something than be empty handed and have the night cut short.

A short taxi ride later and I found myself ringing a doorbell and standing on a doorstep, my heart pounding in my chest like it was going to burst. I realised I didn't know who would open this door, a man or a goddess...

A beautiful trans woman opened the door and hugged me before I had a chance to say "wow"! I just stood there, my arms pinned to my sides and my knees touching, as this warm, beautiful woman engulfed me with love.

"I'm so happy to see you!" she declared

"You look amazing... Thank you for having me over" I stuttered out nervously

"Aw honey, I'm happy to have company. And with someone with such good taste" she smirked. "Come on in, I've gotta see you as you want me to see you."

I immediately felt so empowered to be around this woman. She knew exactly how I wanted to be talked to, and he long fluffy hair and flowing dressing gown relaxed me instantly. No pressure, no expectations, just a relaxing night ahead.

"I'll be honest Miss, I kinda expected you to be fully dressed to the nines! Not that I wanted it! I just... all your pictures"

"Aw honey, those are for nights out, or when I'm feeling slutty. We're having a nice night in were we get to have fun and you get to be yourself for once. I know how you feel, I was like you too."

I found that hard to believe, but the concept of looking as great is Miss got me instantly elated.

...

So to set-up, I had quickly shaved and removed as much hair from my body as I knew how. And for the past 6 months I've been working out (paying particular attention to my hips and butt with some deep squats for that bubble butt look I'm so fond of!), so body-wise I felt reasonably good. I carried in my bag a pair of thigh-high socks, high heels, my trusty long, red wig, and that was pretty much it.

"Mmm, that's fine, hun, we'll sort out your clothes later. BCHNF! Body, clothes, hair, nails, face. that's the agenda. Let's get to work." Miss declared. Then nothing. She just stood there. We both stood here. In the middle of the living room. She was staring at me. Nothing.

"Uhhh...?" I asked.

"Well... Strip off! I'm gonna give you a look all over to figure out exactly what I'm gonna do with you! Danni is a blank canvas right now!"

I took a deep mental breath, and tried to match her perkiness. I want to be so much like her. I drop my bag to the side, and strip off all my boy clothes. I am standing in the middle of her living room completely nude, cupping my genitals with both hands, and red-faced I wait.

She circled me for what felt like an age or three. She prodded my back to have me straighten my posture, and lifted my arms to see all over.

"Okay you've covered most of the hair, and your butt looks GREAT!" (I smiled so hard, Miss could tell it is my pride and joy), "but I'm gonna clean you up fully to get you super smooth. Now sit down for me please."

I sat on her couch, and was shocked when she lightly wrapped her fingers around my ankles and lifted my legs up above my head!

"Yeah I'll show you how to get all this smooth, if you want a man to spread this you're gonna want this to be trap-immaculate." My entire body turned red, and my cock twitched to life. "Hehe, that is the correct response!"

...

With a bath and some magic lotions that removes hair from everywhere, the voice behind the door guided me to perfection. Then a full-body moisturiser had me feeling like human sex-toy.

I was sat down in front of a huge mirror at a desk covered in all kinds of colours and fluffy things and lipsticks. Miss loved the colour of my wig so much she decided to work her magic on that rather than give me something of hers. It's my "signature". Beautiful wavy locks dangled down my neck as she finished brushing it while talking me through everything. I was so relaxed and pampered, it felt euphoric.

"Okay now spin around honey, I'll do your face for you."

Lipstick, eye liner, blush, all things I never even ATTEMPTED myself as I knew how much of a disaster it'd be. When Miss was done, I looked like a different person. I looked PASSABLE! I looked really fucking sexy, if I do say so myself.

"My oh my you look beautiful! God, you look very fucking yummy, Danni. How does that feel?" Miss asked, as she turned me towards the mirror

"I... I can't... it's... incredible! Thank you so much!" I hugged Miss so hard and tight, as hard and tight as she had hugged me at the door. She looked legitimately happy, too.

"Okay, now, last thing's last, we'll get you dressed up and I'll do your nails while you watch TV. You wanna watch my porn videos? Hehe" she joked.

"Well..." I implied

"Haha! You dirty girl! Okay then!"

...

We stood in front of Miss' open closet, my mouth nearly agape at the variety. It went from black elegant to pink cumwhore. I've never felt jealousy on this scale before.

"So what do you want to wear?"

"I've only been able to wear what was lying around. I've never worn "girly" clothes, or felt sexy."

"Oh. I think I know where this is going."

Miss reached into the Cumwhore Section and pulled out a latex corset so small it was basically a strip of rubber.

"Whoa."

"Yeah you don't want to wear this."

"What? It looks super slutty!"

"Honey, your ass turned red when I lifted your ankles, you don't want slutty you want to feel SEXY! And to feel sexy you need to feel believable and comfortable. That's the most important thing right now. When you feel like a natural girl, then we'll get you fucked and you can start worrying about catching jizz in your waiting mouth." she laughed. "So I'll ask yo again, what does Danni wanna wear?"

We ended on some casual, tight streetwear. A sweet Beatles shirt, small hoodie, colourful form-hugging leggings under a little black skirt with pockets and old black Converse sneakers. Miss took a picture of my outfit, hair and make-up for future reference, and to remind me how I should carry myself. Remember point #2? I felt so comfortable and looked so much like a girl I could feel my confidence going through the roof. Miss was completely right! She seemed to beam with pride when I told her.

...

So there we were, sitting on her couch watching videos of trans women sucking fat cocks and being fucked wide open. Chatting so casually about sexual experiences and fantasies and opinions, I felt like one of the girls. I wanted to go on a night out with Miss and her friends from the pictures. I wanted to flirt with older men at bars and high-five my new girlfriends on the way out the door. Miss reveled in this.

She finished painting my last pinky finger a shiney black. "Honey, you're welcome any time. we'll have to protect you, you look so cute the men will be tripping over themselves to get to you! I'll feel jealous of them, too. I'm very bi, and I would top you in a heartbeat." And that was when I heard the sultriest, sexiest laugh in my life. I froze, but tried to hide it. My heartbeat increased. I wondered if Miss knew this, as she felt my hand and casually ran a hand onto my wrist.

Then, in what felt like a choreographed moment of perfection, the TV faded into a clip of a young trap girl sucking the cock of a dominant, latex-covered shemale.

"You like that?" Miss asked, with a voice hushed down a notch from her usual, perky tone.

I nodded.

"I know you said you didn't have much experience with sex as a girl. You feel like practicing?"

I bit my lip and looked into Miss' eyes. I nodded, my hair slightly hanging over my nervous face. Miss reached up and brushed a lock out of my face, then ran her hand up to the back of my head. She pulled it down, and I followed obediently. As she did this, her other hand expertly pulled her gown to the side, revealing her beautiful bulge in a pair of smooth silver panties. I leaned right down onto her panties and took over. I began kissing over her panty-covered cock, taking secret sniffs of her while down there. She brushed my cheek with one hand, mostly to give her space to free her chubby, impressive cock out into the open. I kissed it on the tip, pulling the foreskin down a touch, and continued kissing the precum out from her. I sucked her for 20 minutes, and was surprised she gave me no notes, no advice, she just let me do my thing while she sat back and moaned in pleasure. I took this as a great sign.

"Hun, you wanna feel like a real girl?"

Her cock completely in my mouth, I managed a slight nod and a muffled "Mm-hmm!"

I was subsequently bent over the couch, and Miss pulled my new leggings down to my knees. My skirt was thrown up onto my midriff. My perfectly smooth butt hung out in the air, and my new shemale mistress rubbed it all over. A sharp spank or two liberated me. Those spanks felt like girly initiation, so I thanked her for them with pleasure moans.

I felt the cool lube drip down onto my ass, and my new pussy felt the intense, nerve-tingling sensation of a warm, wet cock rubbing up and down. Then I felt the pressure of Miss' tool pushing against my puckered hole, tip first. It suddenly felt much bigger in this context.

I was fucked like a beautiful, sexy little girl. I felt like a slut, a whore, a bitch, a doll. I loved every fucking second of it. I wanted more! I screamed Miss' house down and covered her couch in cum (No hands! first time!).

"Danni, time for your reward honey!" Miss exclaimed.

She pulled out of my pussy, and yanked me down onto my knees. I already had my mouth open and my tongue out. She grabbed me by the back of the head and forced her soaking, filthy dick into my mouth and continued fucking like she forgot we changed positions. I felt thick ropes of warm cum shoot wads onto my tongue and down my throat, and when Miss slowed her humping, I pumped my head on her cock to keep it going ( I saw that a few minutes ago in one of her videos!)

...

"Thank you so much" I wheezed.

We lay on her couch, I rested my head on Miss' heaving chest.

"You are definitely coming out with me on Saturday. I'll give you tits, we'll get you a Daddy. You're basically my daughter now." We giggled together.

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8 Comments
richgo50richgo505 months ago

Thoroughly enjoyed this story. Would love to experience something like this myself.

sissyboi69Aricsissyboi69Aricover 2 years ago

I loved your story. I have had a fantasy of having a Momma like her for a long time. I would love to be her daughter.

AnonymousAnonymousover 7 years ago
OMG

Wow, I would love to have a wonderful shemale for a play mate !!!! Wonderful story, thanks. .

LadyPenelope784LadyPenelope784over 8 years ago
:-)

Liked the "daughter" part at the end. :-) Always imagined myself transitioning from son to "daughter" xxxx.

AnonymousAnonymousover 8 years ago
Oh dear

More deluded nonsense.

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