I enter Lady Tatiana's bondage playroom, hoping that today will be the day that she unlocks my chastity device. We started my bondage crossdressing sessions 6 months ago and that's when she locked me up in a cruel pink chastity device. Lady Tatiana is an elegant older Eastern European woman with long blonde hair and luscious red lips.
During the last 6 months she has explored my cross-dressing fascination and allowed me to wear pretty women's clothing only in her playroom. I have never walked out in public dressed as a woman although this thought scares and excites me. She has been giving me female hormones and this caused me to have natural small breasts. I'm extremely thin and very passable as a crossdresser. Lady Tatiana has been able to weave a dark brown wig into my natural hair and the wig will not easily come off.
Today Lady Tatiana selected my female clothing for today…a cream chiffon skirt which is very see-through in the day time, a pink silk ruffle blouse with beautiful cascading ruffles on the sleeves and sexy 5 inch black ankle strap heels which are locked. Of course I'm wearing a sexy pink garter belt, pink satin panties, black silk stockings and she gave me a small pink purse which confuses me. She tells me she has an eye opening event planned for me and if I complete a certain task then she will unlock my chastity device.
My locked cock gets hard and my sissy mind is racing as she tells me her special event for me. I'm to walk out into the public dressed in my female clothing, take a public bus and arrive at a certain address to complete my task. The task is a mystery but inside the purse is a note with instructions on what to do. She has also placed some money inside the purse with a lifelike black dildo. The pink purse is lined inside with pink satin material, so the black dildo is noticeable.
She tells me to get going as she pushes me out into the street. The note’s instructions say to walk six blocks down the Main Street, sit on the bench, adjust my garter belt and wait for the 5pm bus. I have gotten used to walking in heels at my home and her playroom, so it's not difficult…But very arousing and scary as people will notice my sexy heels.
I arrive at the bus stop and take a seat on the bench. As instructed I cross my legs, adjust my garter belt straps as men stare and whistle at me. I blush from the attention and my cock is becoming so hard in the small chastity device. An older woman sits down next to me and notices my sexy heels.
"Oh my those are very sexy high heels! How can you walk in those ridiculous heels? I love the style and those tiny fake padlocks are sexy!"
I'm dying from embarrassment and that she might find out that I'm a crossdresser and that the heels are truly locked on. I try to avoid conversation but in a pretty fake feminine voice "Thank you. The fake padlocks add a sexiness to the heels."
She leans in closer "With sexy heels like that I'm sure your husband, boyfriend or whoever fucks you good. Those are truly fuck-me heels!"
I nod yes and see that my 5pm bus has arrived and I quickly read the next set of instructions. I gasp…I'm supposed to open my purse wide as I try to find the right change for the bus ticket, revealing my black dildo to the bus driver!
I step onto the bus with my sexy black five inch heels and I stand in front of the black bus driver. The sunlight is shining and I know that everyone can see through my cream chiffon skirt. I nervously open up my pink purse in front of him, he stares at my sexy silk ruffles as I try to find my money and he sees my black vibrator.
He grabs my hand, he pays for me "Don't worry sexy, it's on me. And my real black cock is larger than your little vibrator. After work I can take you into the back alley and fuck your senseless!"
I can't believe a man thinks I'm a real woman and that he wants to fuck me. I pull my hand away, "No thank you! I'm a lady not a whore." I quickly leave him and walk down the aisle of the bus, no seats only standing room. Then more people enter the bus, we are now packed like sardines and I can hardly move.
Then I feel a hand pinching my ass, I can't even turn my head to see who it is. I can feel my chiffon skirt being lifted and a hand is touching my satin panties. He's soon going to find out that I'm a crossdresser…the hand is now massaging my balls as I moan quietly. Then the hand finds my chastity device as it explores my locked cock. His hand is sending pleasure waves throughout my body, my locked cock is nearing an orgasm.
Oh my this strange man is going to make me cum in public on a bus! He whispers into my ear "My stop is coming up, if not I would have pull out my hard cock and fuck your sissy hole! Yes I know you are a crossdresser…a very pretty fuckable crossdresser. I love your pink silk blouse with the many sexy ruffles on your sleeves! Maybe I will see you tomorrow on the bus?"
The bus stops, he gets off and leaves me frustrated. I'm a straight male and I can't believe this stranger got me so turned on. I'm leaking pre-cum as I prepare for my next set of instructions. My stop is coming up.
I exit the bus and the instructions tell me to walk another eight blocks, turn right into a dark alley and find a certain dive bar. The five inch heels are starting to kill me as I walk down the street. I find the alley and it's very dark and scary. I fear that bus driver could have followed me and then rape me in the dark alley.
I find the dive bar, there are stairs that lead down towards the dark dive bar. The instructions tell me to find the bartender Mitch and he will have my final task. I see the bartender and as I walk towards him I feel very scared to be dressed as a woman in front of strange men.
I tell him Lady Tatiana sent me to him. "You must be prissy. You are very pretty and passable. Come with me and you will find out about your final task."
I follow this scary fat tattooed man towards the back area. He opens up a door to a very small narrow room with a stool in the room. Before I can react he places a collar and attaches a chain leash to the collar and he closes the door.
"Wait! Come back. What is going on? What's my final task?" I get no response as I look around the small room, the chain leash allows me movement but I can't reach the door…I'm trapped. Then I notice two holes on both sides of me and there are cushions on the floor. Oh shit! This is a glory hole! Lady Tatiana expects me to suck cocks for my freedom.
Then I see the first cock enter the hole, it's only a small white cock about 5 inches…not very impressive But still it's a real cock only inches away from me.
My straight mind and sissy mind are battling each other as I fight the urge to reach out and grab that cock. I can't stop looking at it and I think what's the harm in just holding it.
My sissy hand with the pink silk ruffles all around reaches out and softly holds this strange cock. As my hand feels his cock I can hear him moaning. His cock is growing and I'm causing it. "Mmmm…please Prissy suck my cock! I want to feel your sweet lips on my cock!"
How and the hell does he know my name? As I ponder whether I should suck his cock, my own locked cock has grown larger and more pre-cum is leaking. I stare at his cock and I know if I do this I will forever become a sissy…a cock sucker!
I open my red lips and I taste his cockhead, he moans, I suck on his cockhead and without warning he cums inside my mouth. I'm disgusted as I taste my first cumshot and I see a digital display sign that now reads 1.
Mitch opens the door as I wipe the cum from my mouth "You have already guessed that this is a glory hole. Your task that you must complete to earn your freedom is to make 10 men cum inside your mouth. You have a time limit and you only have 20 possible cocks to suck. If you fail Prissy, no key and a possible punishment."
The door closes again and another cock appears…its a black thick cock. It's so thick I can hardly put my lips around it. After a few minutes the black thick cock retreats and this becomes my first failure. I await my next cock and try not to think about punishment.
The next cock is a 7 inch brown cock. I get my red lips around his cock, sucking it to earn my freedom. "You are so pretty Prissy! I love those sexy heels and pink silk blouse! Mmmmm…I love how you suck my cock."
I stop sucking his cock "How do you know my name and what I'm wearing?"
"There's a giant sign outside of this glory hole with your picture and it says 'Prissy: the glory hole slut'…I love how you are featured on your knees with your red lips open."
I can't believe I'm being advertised for a glory hole and men might recognize me. Shit I got to get focus on sucking cocks and swallowing their cum to earn my cocks freedom. Then suddenly he pulls his cock back before he can cum and this becomes my second failure.
My sixth cock sucking is my worst experience. As I'm sucking his cock and playing with his balls I achieve my goal and he cums inside my sissy mouth. His cum is disgusting so thick, salty and he is cumming three times as much as the last man. I swallow every disgusting drop of cum.
The next man begins to flatter me and gives me sweet compliments as I deep throat his cock. He is moaning hard, "Oh yes Prissy! I love you Prissy! Come home with me! I will make you my beautiful bride! I have a basement where I can tie you down to the bed and fuck you hard! Please I want to fuck you Prissy!"
I push his cock away, "You sick bastard! I'm not a sex slave or a whore!" At that moment he cums but inside my mouth, he sprays my face, hair and pretty silk pink ruffle blouse with his cum and this becomes another failure.
After a few hours my digital sign readout says ‘nine’ and I have one last cock to suck. I'm going to give this last stranger a blowjob that he will never forget. I'm so close to earning my freedom.
A large 9 inch black cock appears, "Well hello Prissy, remember me? The bus driver and I know you need me to cum so you can get that key to unlock your chastity device. You are going to fail and will face punishment."
"Please sir, I'm sorry! Let me suck your cock so I can taste your cum. Please!"
I try my best to please his black cock, but it's useless…he's not cumming. Then he becomes another failure and my cock will remain locked up.
The door opens and Mitch, the bus driver and Lady Tatiana are standing outside. As Lady Tatiana torments me by showing me the key that will not be unlocking my chastity device. "Well my sweet Prissy, you failed to swallow ten cumshot's therefore you will be punished."
The bus driver stands in front of my Lady Tatiana, "How much for that chastity device key?"
I'm shocked, scared and quickly answer for my Lady Tatiana, "The key is not for sale…you asshole!"
Lady Tatiana slaps my face. "That was very rude and how dare you answer for me! I have had enough of you with your constant questions about releasing you from chastity."
She turns and looks at the bus driver as she hands him the key to my chastity device. "Give me 10 dollars for this key."
I watch in horror as they exchange money and my key. She looks at me "I'm done with you and find your own ride back home or you can walk in those hooker heels at night…it's only about 3 miles back home."
She leaves me alone with Mitch, the bus driver and my thoughts about getting home safely.
The bus driver looks at me "You basically have two choices come home with me or walk alone at night at the risk of getting raped! It's your choice Prissy"
As he holds my key and as I think about the scary rape possibility or going home with the bus driver…my locked cock squirts sissy cum into my pink satin panties!