50 Shades Of Pale Pink Sissy Ch. 02

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The ongoing story of the girly boy.
9.8k words
4.53
66.4k
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Part 2 of the 3 part series

Updated 10/03/2022
Created 06/03/2013
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davine
davine
234 Followers

All characters are over 18.


It's Thursday. Waking up I'm still miserable. I can't bother to look after myself. I'm dirty and bedraggled in old track pants a tee shirt. After I manage a coffee and toast I decide to check my computer. First I check my bank account and I'm astounded to find that there is twenty thousand more than I expected. I check my emails and find several from Him. I delete them. My phone has been turned off since Sunday night so I fire it up and find twenty texts from Him. Opening the last SMS I find it just says "Please text me". Quickly I flick through the others and find he is imploring me to make contact. He says he misses me. My heart flutters. "What's with all the cash" I send to him.

"It's termination Pay. Call me," is the reply.

"I don't want it."

"Buy something nice."

"Take it back."

"Only if you ring me!"

"NO!"

Phone rings. I ignore it. Phone rings. I ignore it. Finally after the fifth time I answer reluctantly. "HI; MR HORRIBLE."

"WHAT."

"You Know."

"Know what?"

"Apologise!"

"Why?"

"For terrifying me so badly that I wet myself. I had enough of that at school. And you paid that bastard to piss on me, just so you and Jane could get your rocks watching us suffer."

There is silence for a few moments.

"Sorry. Please forgive me. Can we start all over?"

"Only with new rules."

"I'll think about it."

"Don't think too long" I hang up.

The phone rings and I say nothing when I pick up.

"Have lunch with me tomorrow so we can discuss some possible changes."

"I'll have lunch to discuss definite changes. Take it or leave it."

"Ok. I'll send a car for twelve."

"I'll probably be ready" I answer.

I'm feeling a little better after telling him off. My inner bimbo is rejoicing that I will see him again. I just hope I can calm him down a bit. Strangely I have enjoyed most of our time together. I can handle some spanking and humiliation especially when he allows me some pleasure with it. Just to be with him excites me and the clothes are lovely if a little embarrassing at times. I just can't handle the terror that he inflicted on Sunday.

What should I wear to lunch? Will I dress to tantalize him or to upset him. I know he would like me to stick to his favourite style; short, pink, revealing with heels. I'm tempted to wear jeans and a sweater with running shoes just to annoy him. I decide to show him what he is missing out on but not in his selected style. I need to shop and spend a little of his money. I wash, fix my hair and makeup, and throw on a nice dress and mid heeled sandals. After a quick lunch I'm ready to go.

Young teen and sexy is what he'll get. My inner bimbo will love it as would the nasty maid that was banished to Mistress Rebecca's. I love to clothes shop so I had a lovely afternoon buying shoes, lingerie, skirts, shorts and tops. As soon as I arrive home I start modelling for myself.

Midday Friday arrives. The morning has been spent with preparation for hopefully reconnecting with a milder Mr Black. My body is clean inside and out. My hair and face are perfect. I'm sure that my clothes will seduce him once he gets over the shock of my choice of style. My heart is fluttering and there is a delicious tingle happening throughout my body as I inspect myself in a full length mirror. My hair is styled up high as if I was a bride or bridesmaid or perhaps on my way to the opera. Light foundation covers my face. I have gone heavy with mascara, pink glitter eye shadow and blush with bright pink lips. My finger and toe nails match my lips. I have large silver hoop earrings and a silver chain choker. My black Lycra mini skirt is so tight and short that it barely covers my bottom and is moulded to every curve. I know that I will be pulling the hem down to keep my modesty. My top is a red stretch singlet with spaghetti straps. Underneath I wear my usual control thong and sheer to waist, sparkling nude pantyhose. A sheer underwire bra which has no padding allows my nipples to show but makes me appear fairly flat. I am wearing strappy black sandals with four inch heels and have a matching small shoulder bag with my make up, phone and purse inside. I look like a twelve year old trying to be sixteen. I know that I will attract unwanted attention but just hope to gain His attention.

I wander down to the waiting car. Deliberately late, I'm hoping the driver has reported this to Him. With the driver holding the door I settle into the seat giving him a good flash under my skirt. We both blush.

The drive takes only ten minutes and I am dropped outside a huge Hotel in the centre of the city with instructions to ask for Him at the desk. Oh no! I was expecting another quiet restaurant. The foyer is very crowded and I have lots of eyes and whispers following me as I tap across to reception which is very crowded. While I'm waiting and thinking that my clothing decision was a bad idea, I'm approached by a security guard who asks me what I'm doing there. I explain, he looks sceptical and asks for ID. I show him my licence and he leaves me alone to suffer the stares of the crowd milling around the foyer. Finally a pretty receptionist asks me what I want. She is quite abrupt as she looks me up and down with a sneer.

"I'm here to meet Mr Black" I manage nervously to tell her. She shakes her head and sneers again "I thought he had better taste. Take the lift to floor thirty six. You will be met."

With great relief I tap across to a bank of lifts. Fortunately the wait is short and I'm whisked quickly to my floor. I'm met by a bell hop who takes me to a suite .He opens the door and ushers me in. Master is standing inside waiting. His mouth drops open. He recovers quickly and I can see that he is furious with me.

"I should put you over my knee right now. You look like a slut."

"Isn't that what you want; to own me as your slave and to use me for your fun? I thought you would like this outfit."

"I thought you would dress the way I expect you to."

"It was this or the dirty track pants and tee shirt I've been wearing since Sunday night while I cried my heart out. I decided you would like your little girl to look sexy. Don't even think about spanking me until we talk."

"Ok we'll talk while we eat." He is furious.

Following him I find I'm in a dining room with a table set for two. There is a hotel maid attending a side board loaded with food. We sit and she pours His wine. She looks quizzically at Him. He tells her that I'm old enough so my wine is then poured. I lift my glass in a toast.

"Here's to an acceptable agreement." He clinks glasses with me which gives me hope. After eating two delicious courses and each drinking a little too much he asks.

"Explain yourself!"

"I said yes to you because I couldn't see me living without you. You went too far on Sunday. I loved everything we have done. The spankings and sex were fantastic. I even got a tingle from the club scene, though the humiliation and caning was a bit over the top. But Sunday turned horrible. I hated being terrified and pissed on but the worst part was that I thought you were in danger. Promise you won't do that again and maybe I can be your sub. I have been miserable since Sunday. If you want to piss on me; ask me first and I'll think about it but scat is out."

"Ok" he says stands and helps me out of my seat. Taking me in his arms he kisses me deeply. I melt and break down in tears.

Eventually he sits me down again. "I'm glad you dressed to tempt me. It's not to my taste but better than the alternative. Will you stick to my selections from now on please?"

"Yes Master" I sob.

"Dry you eyes and fix that slutty makeup. Then we will have desert."

I run to the bathroom' dry my eyes, drop my hair and fix my makeup. Returning I sit and the maid serves desert and some Botrytis wine. Master leads me to a lounge where we sit while coffee is served. The maid clears up and leaves us alone. We drink our coffee in silence. Master keeps looking at me. I'm embarrassed and blush.

"Those clothes really are naughty you know" he says. "I should punish you."

"I know" I giggle, stand and lie over his knees.

I feel my skirt being pushed up exposing my plump nylon clad bottom. The panty hose is pulled down so now my cheeks are naked to his gaze and what ever he plans.

"That beautiful bottom needs some colour don't you think?" He gently massages my backside.

"It is a naughty bottom" I answer giggling.

He slaps me playfully six times. My bottom stings a little and I can feel it warm up. I know it will itch a little. My body tingles all over and my little clit is leaking into my gusset. My thong is pulled to one side and I feel his finger rubbing against my wet clit and thong. He transfers the liquid to my hole and slowly eases his finger into me. Gasping, I try to push back against him. As he slowly pumps the finger in and out a steady dribble of juice leaks from me. I'm in heaven as I relish the slow drawn out orgasm which is much nicer than the explosive eruption that usually happens. Eventually I'm spent and start to calm down. I feel empty when the finger is removed. He eases me off his lap and slides me onto the floor on my knees facing him. The finger is extended towards me. I'm glad that I had flushed myself really well as I clean off his digit with my mouth.

"May I serve you Sir?" I ask. Soon I'm enjoying engulfing him as I look at his gorgeous face. I love the feel of him in my mouth. He is so hard; like steel yet covered with a silky smooth skin that tastes a little salty with his excitement. To be here on my knees worshiping the man I adore is close to heaven His breathing becomes laboured as he explodes and fills my mouth with his glorious seed. Hungrily I swallow and then lick the last drops as they ooze out. Squatting back on my haunches I lower my eyes. "May I speak Master?"

"Speak."

"Will you take me soon Master? I need you inside my tight little hole so much. It will make me truly yours. I know I can stand the pain and girls are meant to bleed on their first time. Please Master I beg you."

"It will soon little one. We just need to stretch you a little more so be patient. I promise that there will be a little pain but I don't want to damage you."

"I need to move to a bigger plug master."

"You may have the biggest one that will fit when we go out tonight."

I wonder where he will take me tonight and what he will do to me. Hopefully it won't be too extreme. My lipstick is a mess and so I ask if I can repair it. With a smirk he refuses my request and tells me to stand in front of him. He digs his nails into my pantyhose at the knees laddering them.

"Now you will walk back to the car which is waiting outside to take you to my house. When your skirt rides up at the back do not pull it down. You wanted to look like a whore so now you look like one who has just done her work. If you need anything from your place get the driver to take you past there. Maid will help you prepare for our outing tonight. I will travel separately as I don't want to be seen leaving with an underage hooker."

With a slap on my bottom he sends me on my way. I can feel the skirt riding up and exposing my bottom as I tap my way to the door. He laughs.

Once out the door in the thankfully deserted corridor I quickly walk to the elevator. Fortunately the elevator is empty and I descend alone to the lobby floor. There are mirrors on all walls. Hell I look so slutty with my ruined lipstick and hose. Unconsciously I pull at my hem which has ridden up exposing my bottom and exit into the still crowded lobby. My phone rings. I stop and answer it as it is Master.

"You are in trouble little one. I'm watching you on CCTV and saw you in the lift. What did I tell you?"

"Not to pull my skirt down master."

"As punishment I have sent the driver away. You will have to wait out the front until he returns. With luck you won't get arrested." He hangs up.

My skirt rides up as I tap noisily across the lobby attracting stares and whispers all the way to the footpath. I know he is watching so I just have to put up with becoming more exposed with every step I take. Finally I'm at the curb waiting for the car to arrive when a security guard accosts me and tells me to move on. I explain that I'm waiting to be picked up.

"I know that you little slut. You can't work from here and if you don't move along I'll call the police."

Bursting into tears I try to tell him that I have a car coming to pick me up. Quite a crowd has gathered and I feel a hand rubbing over my bottom and then I'm pinched which makes me squeal. I'm about ready to run when I see my limo arrive. I tear the back door open, dive in and pull the door shut. We are soon on the move. My heart pounds as I try to sniff back my tears. Curling up on the seat, I shut myself off from the outside world vowing never to defy master again. Eventually I am composed enough to tell the driver to take me straight to Master's. I must have dozed off as the next thing I remember is the driver shaking me through the open door. Helped out of the car I make my way to the doorway where Mary the maid is waiting for me.

"Come" she says. "We have two hours to get you ready."

I am led upstairs to my room where Mary strips off my clothes, takes me to the bathroom and flushes me out several times. After showering I dry my hair and style it into ringlets. Mary opens a small wooden chest which has a selection of plugs. Rather than black, these are pink and shaped like a penis. They have the base plate and chains that the black ones had. Selecting one that I think will just fit I pass it to Mary. I kneel on the bed with my knees spread wide while she lubricates the dildo and eases it into me. Gasping with the pain I push back against the invader till it pops in. I feel so full but the pain soon subsides. Mary fixes the chains around my waist. Walking around a little I'm very conscious of the plug stretching me. I find that if I sway a little more than usual as I walk I'm not so uncomfortable. If I wasn't so anxious to have Master inside me I would have selected a slightly smaller one.

Soon I'm laced into a tight pink corset which shapes me and exposes my nipples, white stockings and my thong. I settle down uncomfortably at my dressing table and apply a heavy dose of make up. Stepping into a long pale pink dress which is split to the waist on both sides I slip a pair of silver stripper shoes on and practice walking with the plug expanding me. As usual I'm totally exposed while dressed. I wouldn't be less modest if I was naked. Exposed I might be but one look in the mirror tells me that he will find me irresistible.

It's time. I clatter out of the room and head down the stairs where I see him waiting in the foyer. Oh he looks hot; in boots, leather pants and jacket over a white shirt. He has his right hand in his coat pocket and an evil grin on his face. Suddenly the plug starts to vibrate inside me. I grab the banister to save myself from tripping and gasp with shock and pleasure. He laughs and pulls a small box out of his pocket. The vibration stops when he presses a button on the box. My legs are shaking when I reach him and he takes my arm to support me. Pulling me into his arms he holds me while I get control of my self. I'm still tingling inside when he leads me out to the car. A short trip later we pull up at a tall office building where I'm whisked out of the car and up to the roof of the building. My bottom must be stretching as I now hardly notice the size of the plug. On the roof I'm strapped into the passenger seat of a chopper. Master climbs into the pilot's seat and we are soon zooming above the city and out into the countryside. Wow this is all too much to comprehend.

"Do you like your little toy inside you?" he asks with a laugh.

"Yes master. It was a bit of a shock when it started but I did enjoy it."

"Be prepared as you will never know when it might start again. I can increase the speed when ever I feel like it." The thing suddenly starts vibrating so hard that I'm gasping with pleasure within seconds. Then it stops. He laughs and reaches over to squeeze my leg. "You are going to enjoy tonight."

"Will you hurt me?"

"If you misbehave I will spank you. But that is all. Tonight is for our pleasure."

We land near a huge mansion. It's more like a castle. In the growing dusk I can see that the whole place is surrounded by a high wall a few hundred meters out from the building. From the chopper I tap along next to Master as we follow a path to the house where we are greeted by a tall beautiful maid. The house is sumptuously furnished with paintings and exotic rugs. Along a hall we are led to a doorway into a ballroom where we are met by a striking red haired woman in a stunning black evening dress. Master introduces me to Mistress Rebecca. I keep my eyes cast down and give a little curtsy.

"What a cute little toy you have here. Maybe you can lend it to me sometime. I'm sure it would amuse me in the dungeon." Mistress says.

I shiver with terror until Master answers "No Rebecca. I'm sure you have plenty of toys yourself. This one is mine and mine alone." I melt. He values me and protects me.

"Of course if she is naughty you may get to see me punish her."

I know he likes to humiliate me in public so I promise myself to give him the opportunity at some stage.

Mistress waves us into the huge room where about twenty men and women are mingling and chatting. Along one wall there are a similar number of subs kneeling with eyes downcast. All are dressed in white. They are all feminine in some way. There are boys and girls dressed in cloaks, dresses or body stockings. All have their faces made up and their long hair styled. I find it hard to tell what sex some of them are. I start to move towards them thinking that I am meant to join them. Master grabs my arm and pulls me close.

" Stay close to me. You are not one of them tonight." My heart gives a little skip of pleasure at this news.

Mistress Jane approaches and gives Master a kiss on his cheek. I'm jealous but hide it.

"How did your little toy enjoy our Sunday scene?" she asks Master. "I've had to keep mine sedated for most of the week she was so traumatised."

"Antoinette has grown stronger from the experience." Master tells her. "She won't be asked to play that sort of roll again."

Oh I love this man. I gasp as the vibrator starts inside me for a couple of seconds and then stops. Mistress Jane looks at me quizzically and then excuses herself. We are offered drinks. Master takes two wines and passes me one. I keep my head down and follow him as he works the room. Many of the doms complement him on his fine taste in toys. Some stare at me trying to work out exactly what I am. They are all used to Master having a feminized boy with him and also wonder why I'm not kneeling with the others.

"Dinner is served" Mistress Rebecca announces.

We all move to the dining room and settle in at the long table. The other subs follow and kneel behind their Doms. I am the only one allowed to sit. We enjoy a sumptuous feast of four courses with matching wines all served by beautiful maids in matching uniforms. Master whispers that Mistress Rebecca's staff are all she males. I feel something between my legs. Someone is feeling me up from under the table. I peek and find that one of the boy subs is down there trying to feel inside my panties. I slap his hand away.

Master leans over and whispers "that is his job for the night; he has to try to suck or eat every person at the table. I'm glad you didn't succumb to his ministrations." Oh how glad I am that master is not forcing that kind of humiliation upon me. Occasionally my bottom starts to tingle as Master starts the plug vibrating. He tortures me by running it long enough to get me squirming with pleasure and leaking a little juice before shutting it off to frustrate me again.

davine
davine
234 Followers