A Sissy is Born Ch. 02

Story Info
You push my buttons and test my limits!
2.7k words
4.43
53.5k
12

Part 2 of the 4 part series

Updated 10/19/2022
Created 12/12/2012
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

Authors Note: This is, after all, Chapter Two. Reading the first chapter might enhance your enjoyment of this offering. As is often the case when I try to write a story the characters seem to move in a direction entirely different from my original outline. I hope you like where they want to go!

*

You turned and started back to your car so abruptly that I was left kneeling and speechless on the old viaduct. The noise from the train obscured anything you may have said! I was left with a mouthful of cum and wondering what would come next. I stood and followed you still savoring the sweet/saltiness of your semen. The brisk November air made the small drop on my chin feel cold and wet. I wiped it off with the back of my hand and licked it up eagerly. I checked my jacket for traces and found none. As I approached my car you drove by, slowed and handed me an envelope. You drove off without saying a word.

I stood in silence and watched you drive away before glancing at the envelope. The message was brief and explicit: "Well done, Cock Sucker! Do not open this envelope until Tuesday and then follow my instructions to the letter."

So that was it; nothing to do but wait and wonder. The stickiness began to melt away and soon our brief encounter was only a memory. I took some satisfaction from your words of approval.

Tuesday came after what seemed like an eternity. I drove to work and wondered if I should read your instructions before or after work. I knew I would be distracted all day long if I did but would I be even more distracted if I didn't? I couldn't wait. Knowing seemed the better choice. I parked in the back of the lot. My fingers trembled with excitement as I opened the envelope. The message was very specific: "Are you ready to take the next step, Sissy Boy? Go to the Ambiance store at Southgate. You will buy a bustier. You will tell the clerk it is for you to wear and you need help getting the right size. Get a pair of matching stockings. Next go to any of the shoe stores and get a pair of high heel sandals. Finally, go to Party City and get a blond wig. Once you have made your purchases send me an email with copies of the receipts. You have until 8pm tonight. Complete this challenge and we will meet again this Saturday...fail and we will never meet again!"

My heart was thumping in my chest. How could I just ask for help at a sex store? My "clit" was rock hard. I knew I would do it but thinking about it all day increased my anxiety! My shift finally ended. I drove to the store and parked. I took a deep breath, got out of the car and walked towards the store. My heart was thumping; my "clit" was throbbing. I took a deep breath and entered.

"Good evening, Sir! How may I help you?" A very young lady greeted me.

I couldn't look her in the eyes. I looked around the store. I mumbled, "I'm here to buy a bustier."

"Well, you've come to the right place! My name is Candi. I'm sure I can help you find just what you want. What size is your lover?" Candi (she was wearing a cheery holiday name tag) was very professional and polite. I was almost calm as I answered.

"Ah... it's not for my wife. It's for me."

Candi didn't show a hint of surprise and barely hesitated as she ushered me towards the lingerie section of the store. "Well, I'll bet we can find something you'll love wearing. Take off your jacket; I'll need to measure your hips, waist and chest."

As we walked through the store I noticed another clerk waiting on a man in the men's lingerie section. It was you! You smiled and winked. I nearly fainted.

Candi calmly explained the different styles and fabrics. It was as if she sold things like this to lots of men. I picked out a pink bustier with matching panties. She suggested I might consider getting a thong in the men's section since panties don't have room for a man's "extra baggage". I declined but said I did need stockings.

"Of course you will." She giggled. "I'll need to measure your leg to get you the right size."

She measured my inseam and I swear she held her fingers against my throbbing "clit" on purpose. "We have just what you need over here."

As we walked towards the stocking display she paused by the "Toy" section of the store. "Would you like to surprise your lover with one of our toys to spice things up?"

I blushed as I looked at the dildos and vibrators and things I didn't even know what to call. "Not tonight." I mumbled.

"Well, maybe on your next visit." Candi rang up the sale, put my items in a bag and smiled as she handed me the receipt. "Please come back and ask for me, I'm here most evenings." Candi was professional to the end.

"Thank-you, Candi, you can be sure I will!" I said as I handed her a twenty dollar tip.

"I hope so, Sir! And, thank-you!" She smiled. "Now go have some fun with your lover."

I walked towards the store's front door and looked for you. You left and I don't know when.

The shoes and wig were a snap after that. I went home. I hid my purchases in the trunk of my car. Hurried in the house and sent you the copies of the receipts. You didn't respond until Thursday.

"I hope you had as much fun Tuesday as I did watching you. Isn't Candi a trip? I hope you like your next challenge. There is a medical office building on Blaine Ave. On the second floor there is a unisex restroom. On Saturday you will enter that restroom at 12:45pm sharp. You will dress up for me complete with lip stick and face powder. At 1pm I will knock on the door. One knock, a pause of one beat and then three quick knocks. You will let me in. Don't forget a towel and wash cloth and you might want a pair of sunglasses, I'm going to take pictures!"

Saturday morning couldn't come fast enough. I followed your directions to the letter. I put my regular clothes in the gym bag I brought my sissy costume in and was putting my lip stick on when you knocked. My heart raced and I tried to slow my breathing as I let you in and stepped back.

"Oh.h.h! Cock Sucker! You look marvelous! Now, put on the sunglasses." You latched the door.

For the next few minutes you had me pose in every position possible. When I tried to adjust my panties you told me to let my "clit" do its own thing. You even took picture of me peeing in the pot! You made me kneel and play with my "clit". "Tell me what you are." You insisted.

"I am a cock sucking sissy."

"What do you like to do?"

"I love to suck cock."

"Again." You continued to take pictures.

"I love to suck cock."

"Say it like it's the most important thing in the world to you."

"I lov.v.ve to suck cock.

There was a knock at the door. I was scared to death! "Stay on your knees, Cock Sucker." You knocked twice on the door. There were four quick knocks. You opened the door and let a strange man in. "I told you I had a cock sucking sissy!" You said as you smiled and walked behind me.

"I don't believe it!" Your friend whispered almost breathlessly.

"Believe." You massaged my shoulders. "Tell the nice man you are a cock sucker and that you want to suck his cock."

I look at you helplessly; not sure I'm ready for this.

"Tell him....now"

I swallow hard and try to speak but can't.

"Would you like us to leave you here dressed like you are?" You nudge the gym bag with your foot.

"Oh, please...please don't...you wouldn't!"

Your friend unzips his trousers and pulls his flaccid penis out. It is small and pretty and pink. I look at it and hear myself, "I am a cock sucker!" It is surreal! It is like I'm watching a porn video. Two normally dressed men are forcing a third to be their slut. But it's not a video! It's real and I'm the slut, a very willing slut deep down. I'm just afraid things are happening too fast! I want to suck that cock! I want to suck lots of cocks. Your friend brushes my lips with his penis. I open my mouth and look up into his eyes. My heart is pounding, my chest is heaving, and I lick my lips. He smiles and brushes my tongue with the tip of his penis. "That's right, cock sucker! Say it again." You continue to take pictures all the while.

"Please, Sir, let me be your cock sucker too!" I pant hoarsely.

He laughs. It's a wicked laugh, a dirty laugh. He knows I'm going to suck him off. "I thought you'd never ask, Slut!"

I reach with both hands and grab his ass. My mouth encircles his limp penis. I pull him closer; sucking the tiny thing completely into my mouth. My lips are inside his fly. "You love this don't you, Cock Sucker?" You ask rhetorically.

I moan as his penis starts to grow in my mouth. His hips twitch. I massage his ass as I start the age old dance. Head bobbing, tongue licking, lips pulling. In and out, over and over as my mouth becomes his pussy! I hear eager slurping sounds. I feel a cock growing stronger. It fills my mouth. It grows longer and I try to take it into my throat!" You take more pictures. My sunglasses and long blond wig obscure my face. My knees are beginning to ache but I continue eagerly. I am a cock sucker! I love sucking cock; my "clit" is poking its head out of my panties. I am a cum slut...eagerly working for my reward. It happens. Your friend cums abruptly and he pulls out. Another spurt hit's my forehead. I try to recapture the spurting cock. He laughs and puts his hand on my forehead. "Hold still, Slut!" He commands as he milks the last few drops onto my face. You're still taking pictures.

"That was awesome, Cock Sucker! You're going to love the pictures!" I scoop up as much cum as I can and savor it slowly. "She really likes eating cum. doesn't she?" Your friend observes."

"It's so delicious!" I answer. "So much better that my own, I love it." I say emphatically.

"Would you like more?" You ask as you hand the camera to your friend and unbuckle your belt.

"Oh yes! Please! Please let me suck you too!"

You step out of your trousers. You're not wearing any underwear. Your cock is already hard. I start to take you in but you stop me. "You can start with my balls this time!"

"Of course." I smile and start licking, kissing, sucking first one then the other...then both.

"Your "clit" needs attention, Slut. Play with yourself! I want you to cum while you suck my balls! I want you to empty your balls for me. Catch your cum in your hand and eat it for us. Show us what a dirty cum whore you really are, Cock Sucker!"

"Not that! Please...don't make me do that. I love the taste of your cum but I can't even think about eating my own." I plead pitifully.

"Don't make us leave you here without any regular clothes, Slut, believe me,,, I will do it!"

I continue to suck your balls and whimper like a scared little girl. "Please don't make me do this...please!"

"You want to do it, Slut. You know you want to show us how perverted you are! You want us to see you licking your cum off your hand. Do it, Slut, start jacking off right now or we both leave with your clothes!"

Tears are welling up in my eyes as I start stroking. My "clit" is so hard it hurts. I make more obscene slurping sounds as I suck your balls. I want to get this over with but my "clit" won't cooperate! "That's better, Slut, doesn't that feel good. You like to jack-off don't you? I'll bet you play with yourself all the time. You dream about cocks and balls and cum and you play with that little "clittie" all the time don't you?"

I moan in agreement, nodding my head as I suck your balls and stroke my "clit". "I knew it!" You exclaim excitedly. "You touch yourself all the time at work when no one is looking, don't you?" I moan. "You rub your "clit" in the car too!" I moan. "You pull it out while you drive, don't you slut boy?" I moan louder, suck even more eagerly, nodding my head in agreement as I look up into your eyes. Your buddy continues to take pictures. I can't stop. I wouldn't stop even if I could! I gasp for air. I'm going to cum. I feel it building, ready to boil over. I feel pre-cum on my thumb and fingers. My balls tighten; I'm panting, slurping, sucking, and moaning. My "clit" is burning up, almost painfully burning, deliciously burning, and ready to spill my hot load. You step back. The best cum in weeks...maybe months! My semen spurts into my hand.... once.......twice.... three times. You snarl, "Eat it Cum Boy.....do it! Do it now!"

I don't hesitate. I can't hesitate; if I do I know I'll fail! I bring my hand to my lips and eat my fresh, hot, sticky cum. I feel queasy, light headed....spent. My limp "clit" is still dripping, I'm sucking my own cum from my fingers. I'm enjoying giving the two of you this dirty little show. You're putting on your trousers. "Let's go." You say quietly. "Bring the bag."

"No....no...Not that! Don't leave me like this!"

"You're going to be just fine, Cock Sucker! You're even going to like what's coming next!"

You leave me kneeling in the restroom wearing only the bustier, tiny panties, and stockings. My face is a mess, there's cum on my wig and sunglasses, I'm sobbing, semen is dripping from my wilted "clit" as a woman enters and locks the door behind her.

She's in her early forties, twenty years younger than me. Short, a little over weight; very pleasant looking. "Honey, you are a mess! What have those bad boys done to you?"

I'm speechless. I try to talk but can't.

"You don't have to say a word, Dearie. You've been a very bad girl, haven't you?" She offers me her hand to help me up. "Let's get your shoes on and get you out of here."

"I can't leave like this!" I object.

"Of course you can, Sweetheart, you can't stay here forever, can you? She takes off her car coat. "Here put this on." It fits a little snugly but at least it closes around my chest. It seems to only half cover my ass! "Let's go!" She takes my hand leads me into the lobby and to the stairwell. I'm having trouble walking in the heels. "Steady, Sweetheart, don't fall and break something." We enter the lower lobby and head for the front door. A custodian is sweeping the far end of the hall. The cool air makes it feel like my crotch is completely exposed. As we cross the parking lot a woman is walking towards the building. She stares in disbelief.

We get in the woman's car; I take a deep breath and let out a sigh of relief. Her hand strokes the top of my stocking clad thigh. She squeezes my thigh gently. "Mama's going to take good care of you, Sweetie!"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
cdCindy1cdCindy1about 6 years ago
fantastic

Loved this story. I too go shopping and I tell the salesgirls that the clothes are for me. At first it was a bit embarrassing but now it's very exciting. Telling a complete stranger that I'm a sissy faggot cocksucking CD is wonderful.

AnonymousAnonymousover 10 years ago
Oh my Aching clitty!

I can not. Wait to read what Mama is going to

Do. I love forced bi / feminizAtion.

She like myself loved to submit and the

Humiliation is devine!

AnonymousAnonymousover 10 years ago
Great story

I am loving it. Dreaming it is me. I can feel precum on my black lace Victoria

secret panties.can't wait for part three.

sally_spandexcdsally_spandexcdover 11 years ago
mmmmm cock sucking sissy,,,aren't we all

What a sexy and hot hot hot story. Isn't it fun being a normally straight man and then becoming a slutty cock sucking sissy.. I know it is for me. After douching as I slide into a pair of pantyhose and tucking my clit away, its like BOOM , and all I can think about is getting some cock. Then as I pull on a tight spandex dress that barely covers my ass and hugs it like a firm hand the feelings only get stronger and stronger and as I put on my make-up I make sure its super slutty because I want all that see me to know Im wanting some cock. And cock I will get, either at the highway rest area or the motel about 3 miles from there or maybe the ABS, where one might I sucked 7 cocks and never came untucked,, no no that night I was a true cock sucking sissy...Oh god back to your story,,,HURRY..I cant wait to see what the new woman in the story has in store for the sissy,,,kisses Sally

AnonymousAnonymousover 11 years ago

dont stop there i must read more of this story

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

I Begged Him To Kiss Me! Ch. 01 A young married guy is seduced by his elderly male neighbor.in Transgender & Crossdressers
A Day with Ron as My Master Ordered to give blowjobs for humiliation.in Transgender & Crossdressers
Bitch Once a sissy whore, always a sissy whore.in Transgender & Crossdressers
Caught by Neighbour Husband in panties is left in an awkward position.in Transgender & Crossdressers
Birth of a New Sissy Ch. 01 Average guy meets a neighbor and finds a new hobby.in Transgender & Crossdressers
More Stories