Transformed - Cock Hungry Sissy Ch. 01

Story Info
Two best friends turn Jessie into a sissy.
1k words
4.43
56.5k
54

Part 1 of the 4 part series

Updated 06/11/2023
Created 04/29/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Hush1223
Hush1223
534 Followers

"You like to wear panties???" my best friend Chloe exclaimed as we were in her car driving back to her place.

"Yes," I sheepishly say while looking out the window. It was my biggest secret, and it was one I couldn't keep to myself any longer. Chloe was my best friend and very progressive. I was hoping she'd understand and not judge me for it.

"Wait, are you joking? Why?"

"Um, I'm not really sure why to be honest. They're just different than guys underwear. They're more comfortable, I like the way the feel, and I don't know... I like the colors."

"Oh my god. This is not what I expected when you told me you had to tell me something," Chloe says as she pulls into her driveway. "When did this start?"

"It started pretty recently honestly. It's something I wanted to do for a long time, but never really had the courage to go out and buy some. I did the other day. But I was so nervous in there, I got a bunch of random sizes and types. Only one fits me well."

"Well, you do know you are going to have to show me what you're wearing right now, right? Oh my god, I really can't believe this."

"I can't show you that! That's weird! Plus, I'm not even wearing any right now."

"Wait, why not? I thought you said you liked wearing them?"

"I do, but I only have the one pair that fits, and it's not like I wear them all the time or anything."

"But you want to don't you?" I hesitate answering before she asks, "Wait, so are you a cross dresser or something? Or is it only panties?"

"Well, it's only panties but..."

"Oh my god, you're a closet crossdresser!" she says giddily while getting out of the car. "Okay, come on inside, I have so much more to ask you. Do you like to wear makeup? Have you ever gotten waxed? Do you shave your legs?"

I follow her into her house, staring at her sexy trim figure as I do. She's wearing a tank top and light blue, tight workout shorts, with a very obvious thong outline showing. I wondered what color it was as I walked inside.

"Okay," Chloe says as we sit on her couch, "be completely honest with me right now. Do you really like to wear panties?"

"Yes.."

"And would you like to dress in other feminine clothing, like skirts and dresses?" I again hesitate to answer. "Be honest with me Jessie, it's totally okay. I'm not going to judge at all."

"I think I do..."

"Eeeeeeek!" Chloe says jumping up from her seat, clapping, "This is so exciting! I'm going to turn you into the perfect girl. Wait, can I call Maya? She would so love to help me transform you."

Maya was another good friend of mine, and an even better friend of hers. I was comfortable telling Chloe my secret, and even having her help me transform, but Maya I wasn't as close to.

"Please, please, please, please," Chloe begs.

"Okay fine, but no one else can know about me."

"Yay!" Chloe exclaims and quickly gets Maya on the phone. "Okay, she's coming over in 20 minutes. In the meantime, go in the bathroom and take a shower. Use my little shaving kit to get those nice little legs of yours all smooth, if they're not already," she said giving me a wry smile. "Just come out in your towel when you're done."

In the shower, I was finally able to reflect on what just happened. I just told my best friend I wanted to experiment with cross dressing, and not only was she fully accepting, she brought my other good friend into the mix, and was about to give me a full makeover. I couldn't contain my excitement as my little dick grew to 4 inches hard and I jerked it furiously until I came. I finished shaving and dried myself off, admiring my smooth white legs.

Chloe was waiting for me in her room with Maya. Maya and Chloe were similar in size. Slightly taller than Chloe, and skinnier, but still gorgeous just the same.

Maya ran up and hugged my toweled body. It's a good thing I just jerked off, because I would've gotten hard on the spot. "Oh my god Jessie! I'm so excited to turn you into a pretty girl! You're gonna look so cute," she stood back admiring my naked body, "You have the cutest little frame. This is gonna be so easy."

My face flushed, all I could do was nervously smile. I wasn't big like other guys. I was a modest 5'7, only a few inches taller than Chloe and 1 inch taller than Maya.

"Hmmm..." Chloe said while twirling a pair of small frilly pink panties in her hands. "We can just give you a makeover here. We're about the same size, in everything. I might be a little smaller than you, but you should be able to fit into my outfits... BUT, I think it would be sooooooo fun to have you go to the mall looking all male and icky and leave looking like a drop dead gorgeous girl!"

Maya clapped and smiled playfully, "That's a wonderful idea Chloe."

"I know right! So Jessie, you're going to just put back on the exact outfit you came here in, but you're going to wear this pretty little thing instead of those disgusting boxers you came here with," she said still twirling the thong around. "We're going to be trying on panties in Victoria's Secret, and you can't just try them on without something underneath. Believe me I tried, they won't let you."

"Are you sure he'll be able to fit into those Chloe? Wouldn't his man bits sneak out? "Maya said.

"Hmm, you may be right Maya. Jessie take off that towel and show us what you're working with."

Before I can protest, Maya rips the towel off my waist, as my "man bits" are revealed to two of my good girl friends.

"Oh my god! You're so small! Perfect!" Chloe says, throwing me the frilly pink panties that I now see to be a thong. "And you did so well shaving! Now put that on with your sweats and sweatshirt, and meet us in the car. This is gonna be so fun!"

The girls walk outside as I look at the soft, frilly, girly material in my hands. What did I get myself into?

Hush1223
Hush1223
534 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
4Leather4Leather8 months ago

Loved it, can’t wait for the next chapter, Shopping in Victory Secrets can be a mind blowing time.

dreamer31adreamer31a10 months ago

cant wait to start next chapter

AnonymousAnonymousalmost 2 years ago

i am a boy ready to get fucked by a shemale and dominatrix message me on insta jhon739146

ChrisissyChrisissyalmost 2 years ago

Great start on every CD, TV, or TS's dream come true!

LannaLaceLannaLacealmost 2 years ago

Intriguing beginning!! I would sooo love to go to V Secrets with a couple of hot chicks and have them dress me up in sexy stockings n garters, panties, bras, bralettes, corsets!...and then what CUMs next?

Show More
Share this Story

Similar Stories

Sissified Ch. 01 Young boy is helped by his hot tutor in his transformation.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
Pool Day Takes a Turn Randy forgot his bathing suit.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
More Stories