tagTranssexuals & CrossdressersBeing a Sissy for Viv Ch. 01

Being a Sissy for Viv Ch. 01

byCaron©

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I."

"Oh, what was so interesting about it?" I asked.

Viv paused for a moment, her eyes on the wine glass in her hands.

"It was about turning men into maids. Sissy maids."

"Mmm that would be exciting." I murmured. The words out of my mouth before I even realized. I felt my cheeks begin to flush as Viv looked at me closely.

"You find it exciting Chris?" I couldn't answer her but I felt the flush of my cheeks answer for me.

"Well well well." she said softly "So you do."

I couldn't meet her eyes as the heat of my cheeks became even more intense. Instead my gaze rested on her breasts, the lace of her bra discernable under the thin white polyester blouse.

There was a silence between us. All I could hear was the ticking of the clock. My thoughts whirled, the embarrassment of Viv knowing, the excitement at the thought of being a sissy. The two feelings chased each other around in my head and my manhood reacted as it always did when those so familiar thoughts went through my mind.

I'm not sure how long the silence lasted. No doubt a far shorter time than it seemed to me. Eventually Viv took a deeper breath. It pushed her breasts out revealing more of her lace bra cups and allowing me to see I wasn't the only one who was getting hard. Her nipples were becoming increasingly obvious under the thin fabric of her blouse.

"So Chris," She said as she crossed her nylon covered legs, "would you like to be a maid yourself?" She paused.

"A pretty sissy maid in a lovely little maids dress?"

Of course I do, my thoughts cried out, but my lips wouldn't move. Viv gave a short soft laugh and at last my eyes were drawn to her face. She had a wry smile on her face and a twinkle in her eyes.

"It's alright Chris, I can tell you do. I can tell you would get so excited wearing a smart little satin maids dress. And the panties of course. Soft satin panties with those pretty little ruffles peeping out from under your skirt when you bend over."

She had a bigger smile on her face now and her eyes were alight. Under her blouse her nipples seemed more clearly visible.

"And of course we'd have to give you something to fill out your dress properly. A nice pair of boobs and a pretty lacy bra to hold them tight."

She paused to take a gulp of wine and then pushed out her tits, stretching her blouse over her lace bra cups, making her hard nipples proud and obvious.

"Do you like my bra Chris?" Our eyes met and she smiled again.

"Well. Actually I know you do because you've been looking at it all evening. You know what. I'm going to make you wear it. But first you have to tell me you want to be a pretty sissy maid for me."

I could hardly breathe, almost unable to comprehend what Viv was saying. The excitement and embarrassment chased each other even faster through my thoughts. Then slowly, almost in a dream, I nodded my head.

"Tell me what you want to be Chris, tell me what you want to wear for me."

"Please" I whispered.

"Come on Chris. Chrissy, just tell me what you want to be for me."

I hesitated, like my brain had forgotten how to work my mouth.

"To. To be, a maid."

"That's it Chrissy," her voice soft and gentle "what sort of maid, come on you can tell me."

My mind was a whirl of conflicting thoughts and emotions. My body felt weak and my stomach queasy. The enormity of the admission my words were making was like a huge neon warning sign in my head. Even stronger was the excitement. It grew to an unstoppable torrent and the words came out shaky but clear.

"A sissy maid." I said between deep breaths.

"Well done Chrissy you are a going to be a good little sissy. Now tell me what you want to wear for me."

"A dress. A pretty maids dress." The words didn't seem to be mine. Sounding almost detached and far off.

"Of course you do Chrissy, and what about under your dress, what do all sissies love to wear. What gets little sissy boys like you all excited for their mistresses?"

"Pretty panties, pretty little panties and a lacy bra under my dress. Ma'am"

"Well then come on Chrissy and we'll turn you into the pretty girly-boy you want to be."

Viv got up and took my hand, quite literally leading me upstairs. My erection was obvious and made walking both awkward and exciting. Following close behind Viv on the stairs meant my face was only inches from her backside. My eyes studied it as it moved around under her dark knee length skirt, giving my erection no chance to soften at all.

Once in her bedroom she let go of my hand and opened a draw. Inside I could see a jumble of bras and panties. My cock twitched at the thought I was going to be sliding a pair of her panties up my legs in just a few seconds. The thought brought an involuntary deep breath. The confusion of thoughts subsiding slightly as the physical anticipation grew.

After a few seconds of rummaging she pulled out a pair of deep pink lace and satin panties. Lacy at the front and slinky satin on the backside. She held them up between her fingers.

"Do you think these would suit a pretty panty boy?" she asked with humour in her voice.

I nodded as my eyes took the sexy panties in.

"So tell me what they will make you when you have them on Chrissy?"

"A sissy panty boy ma'am." I replied in a small voice after a few seconds hesitation. Slowly I was starting to loose some of my shyness and embarrassment. She handed them to me, my hands shaking as my fingers felt the cool softness of the satin fabric. My cock twitched again, I was eager to feel it settling into the sexy pair of panties.

"Well come downstairs wearing nothing but those and then I'm going to put you in my bra."

As she passed me to go downstairs she paused next to me and our eyes met. She was standing close, one of her breasts against my arm. A hand slowly trailed down my stomach and between my legs. Her eyes seemed to sparkle and lipstick covered lips worked slightly as her fingers brushed lightly over my hardness. I could feel her nipple hard against my arm. As well as the lace of her bra cup, a bra she would soon watch me put on.

As soon as Viv left I stripped off breathing hard and deep, my cock springing out as I removed my briefs. I was so excited, and unsure how I was going to get my cock into her panties without doing myself an injury. I watched in the mirror as I stepped into those pretty pink panties and pulled them up my legs. Almost groaning as I pulled them over my ass cheeks and felt myself settling into the lace. My hard manhood being pushed up against my stomach by the elastic in the waistband.

I watched my erection and felt it twitching in the mirror. It was all I could do to hold back from playing with myself right then. But I knew Viv would not be happy with that and I reluctantly stopped myself. With a great amount of willpower and distracting thoughts I managed to get my manhood soft enough to bend it between my legs. Instead of poking above the waistband it formed a large bulge in the front of Viv's pretty panties.

Taking a few deep breaths I slowly left the bedroom and headed downstairs. Walking about a strange house, naked but for a pair of pink lace panties was a real thrill and the bulge beneath the lace was just as noticeable by the time I got back to the lounge.

"Well now Chrissy you are an excited pretty little panty boy aren't you"

"Yes ma'am." I murmured. It only took me a single glance to realize Viv was no longer wearing a bra under her blouse. Her large breasts were tight against the thin fabric and her nipples and dark areola were very obvious. Her bra lay draped over the couch, the sight of it made my cock twitch, Viv smiled as she watched my panties and the movement inside.

"And what's causing that bulge in those panties of mine your wearing Chrissy?"

I couldn't help smiling, it was abundantly obvious what the bulge was but she just wanted to hear me say the words.

"It's my cock ma'am."

She smiled back "And that shows you're a real sissy panty boy doesn't it Chrissy. You get so excited and your cock gets so hard just because I make you wear a pair of my panties."

She reached out and picked up her bra from the arm of the couch. It hung from one of her fingers, white, lacy, feminine and very sexy. My eyes went to the breasts it had supported a few minutes before. Viv's nipples were now hard and erect under her blouse and easily discernable.

"Well come on Chrissy I know how much pretty little sissies like to wear sexy bras so come and put my bra on."

"Yes ma'am." I stepped towards her and took her bra from her hand. It took me only a few seconds to sort the straps and cups out and then slide my arms into the straps before reaching behind myself to fasten the two catches. "Well well well," said Viv. "by the way you put my bra on I can tell you have done that more than once or twice. You wear bras a lot Chrissy don't you."

"Errr ... yes I guess so ... ma'am."

"What size bra do you normally wear Chrissy."

"A 38 or 40 ma'am. Ummm a B cup."

"Well mine is a 38 C cup so it should fit you just fine, but panty boys need a little help to fill out the bras they have to wear. Go and fill my bra out with some more of my panties."

I grinned and started out the door heading for the stairs and Viv's bedroom once again.

"And make sure you use enough panties to make your boobs a full C cup Chrissy." She called out after me.

With my cock still constrained by Viv's sexy pink panties and her bra tight around my chest I went back upstairs to her draw of lingerie. My bulge pushing at the lace fronted panties as I sorted her knickers out. I would of loved to spend more time examining her collection, but I felt I had better not keep my new mistress waiting too long. I looked at myself in the mirror as I filled her bra cups with panties. I didn't really match I guess with bulging pink panties and a lacy white bra, but the fact that the bra had been supporting Viv's own substantial breasts only a few minutes before more than made up for that. And it felt wonderful with my stiff tool bulging against the intricate pattern in front of her panties and the feeling of the tight straps of her bra around my chest stuffed out to a full C cup with her panties.

Back downstairs Viv was waiting for me, her nipples still hard and obvious under that thin blouse. I noticed she had pulled together the two foot stools.

"Well you do look a picture in your bra and panties Chrissy. But I think its time to do something about the bulge you've got from wearing my pretty panties. Don't you Chrissy?"

I just nodded as my cock twitched again.

"Well lie down on the stools then."

I did as I was told, my head just a few inches from the side of her skirt as she stood watching me getting more comfortable. Her eyes taking in one of her male work colleagues wearing nothing but one of her bras stuffed full of her panties and another pair of her panties stuffed full of his hard rampant erection.

She moved down my body and patted my thighs.

"Come on Chrissy spread your legs for me. Show me what a slut you are. You are a slut, all sissies are sluts aren't they Chrissy."

"Yes ma'am" I replied, spreading my legs for her as ordered. Feeling the front on her panties pulling tight on my stiffness, almost making me cum.

"That's right, all panty boys are sluts because when their dressed their cocks get really excited by all that soft pretty underwear. And when their really hard and excited they'll do just about anything to get wanked off just like a slut would. Isn't that right Chrissy. Will you beg me to wank you off in my panties just like the little sissy slut you really are?"

She was right. I was so excited by now I would do almost anything to feel her fingers on me.

"Yes ma'am, please wank me off ma'am."

"Tell me what you are Chrissy" her fingers stroking up the insides of my splayed thighs.

"I'm a sissy slut ma'am."

Her fingers continued to roam between my legs, tracing the edge of her panties. My cock twitched under the pink lace, aching for the touch of her fingers.

"And what do sissy sluts want Chrissy, tell me what you are and what you want and I might just give it to you."

I moaned as Viv lightly ran one of her fingernails across the top of my erection.

"Come on Chrissy, you can tell me." She said as a moan escaped from my lips.

"I'm a slut ma'am, a sissy slut and I want to be wanked off ma'am."

Viv's finger slipped inside the leg of her panties, gently probing between my hard manhood and balls.

"I'm a panty boy and I want my Mistress to make me cum."

Her fingers were now on my cock gently caressing it through the lace of her panties. I was gasping and moaning gently.

"Come on Chrissy tell your mistress what it is you need so badly."

"Please wank me off ma'am. I'm a sissy slut and I want to be wanked off, made to cum in your panties."

She was squeezing my cock, just using her finger and thumb to pump the head. Making the tip slide back inside the foreskin.

"Mmmmm" came out of my mouth as her fingers played with me through the lace.

"I'm a girlie panty boy."

She kept up the rhythmic pumping on my cock.

"I'm a sissy slut who wants to cum in your panties."

Squeezing on the tip making it slide inside my foreskin then letting go

"I'm a little sissy slut, please, mmm, make me, ahhhh, cum in your, panties, please."

There was no let up in the rhythm of her fingers, just her thumb and two fingers pumping away through the lace of her pink panties she had told me to wear. Squeezing the head of my erection back into the foreskin and then releasing to let it emerge before squeezing it back in again over and over.

"I'm a panty slut and I want to fill your panties with my cum." I groaned and took in a huge gasp of air suddenly feeling the bra straps around my heaving chest. I glanced down at her white lacy bra round my chest, stuffed with Vivs panties to give me jutting C cup titties. Panting for breath I raised my head higher looking at the huge bulge of my cock in Vivs pink panties. Her fingers on the bulge, still pumping away, inevitably bringing me to the point where I would fill her pretty panties with my cum and show her just what a sissy panty boy I really was.

"Beg me for it Chrissy, let me hear what a real panty boy you are."

"Please ma'am, make me cum, make me cum in your panties."

There was no holding back for me now.

"I'm a sissy slut and I want to fill your panties with my cum. Make me fill your panties with my sissy cum. Please ma'am."

I erupted into Vivs pink lace fronted panties, my hot sticky cum spurting out, her pumping fingers slowed but didn't stop. Slowly milking my cum out of and into her panties. Her fingers becoming slick and slippery. She stopped pumping and slowly slid her hand inside. I bit my lip as her fingers delved through my pubes, going the length of my softening prick and squeezed gently. Then her hand started spreading my cum around, methodically rubbing the fluid around inside her panties. Soon her hand and my cock and balls were sticky and slippery.

Only then did she bend forward, her warm breast against my arm, her hand still holding my semi limp manhood.

"Well Chrissy I think you are going to make an excellent panty boy. And I am just going to love making you wear lots of pretty girly things and then watch you show me just what a sissy slut you are."

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by Anonymous

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by Anonymous12/09/14

great story

This reminds me of when I finally told my wife about my cross-dressing. Just like in your story, I felt fantastic and actually relieved when I finally said the words out loud to my wife. I said to her:more...

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by Anonymous12/06/14

panties in bra, really?

more...

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by Anonymous05/07/14

good story

yes i become my female room mate bitch i was put in panties and bra and told to wear a dress then she throw out my male clothes you wont need these any more you be dress as a girl well after five monthmore...

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by Anonymous02/18/14

Cindy's house Part 1

Hello, from Jenny. Here's another event from my story section. My neighbor Cindy keeps Bobby totally humiliated all the time. This is the first of our wimpy pathetic sissy's training.

I came home at lunchmore...

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