XXX What My Big Sis Started
Here's my slant on every Sissy's favorite story line of a young man being made a sissy.
Posted on
Add A New Story
  Click!
I whipped round in shock, 'cos I thought I had locked myself in.
There stood my big sister Ayla with a triumphant grin, brandishing her phone.
"Caught you at last!" she laughed.
I was too embarrassed to answer too speechless. She had indeed exposed me, and just as I was enjoying the lovely sensation of pulling up her soft tights over my private parts!
I had nothing to say. I was standing in Her underwear, wearing Her pink bra, in Her bedroom. She'd told me she was out on a date.
But obviously not.
She slipped into Her room, closed the door, and locked it.
"Better not let mum see you like this, Terry!"  she giggled again.
"No, no. I-I..."
"Of course, I knew you've done this before, haven't you?"
I nodded slightly.
"Yeah, when I smelled my clean panties recently, I knew it was you! And now, little bro', I've got you where I want!"
I stared at her, scared. She was only a year older than me, but had always enjoyed being my superior. Whatever way I tried, she always came out on top- like now.
"You're not gonna tell...?" I hesisted to choke out the question.
"Not if you're a good boy. And you are a good boy little Terry, aren't you?"
"I-I hope so."
"Mum is always worrying me to look after you now you've started college, and now I'm in a position to properly care for you, aren't I?"
"Are, are you?" I wasn't sure what she was driving at.
"Oh yes, you wouldn't want mum to see the photo I took just now of you, would you?"
I shook my head firmly. Though I loved my mum, I was always  scared she might find out my little secret. She'd be furious, because she wanted me to be her big boy, but somehow I knew I hadn't lived up to her expectations.
It wasn't my fault.  Mum wouldn't take me to a doctor, I think she didn't dare to admit I hadn't been the same as the others at high school. The internet calls it delayed puberty.
"Well, if you do what I ask," continued Ayla, "I'll give you permission to wipe that photo from my phone."
"Promise?"
"Promise."
I waited still shaking from being found out,  hoping she wasn't gonna ask me to do anything like appear in public in one of her dresses. Actually I'd fantasised about doing just that, but I'd never have dared in a million years.
"Okay, little bro'," she began, as I drew in my breath, "my best friend in college says she doesn't believe your voice hasn't broken yet, and that you don't need to shave. She bet me £20, so I wanna win by letting her see you."
This didn't sound too bad.
"Oh, I did say you'd pass for a girl," she added to my horror, "so  you'd need to convince her, then I will allow that photo to be deleted."
My mind was racing. It was bad enough my Big Sis had seen me, but I couldn't possibly let a complete stranger see me like this.  I thought of a myriad  difficulties.
"Where and when do I meet her? I'm not going out in public like this..."
"Oh no, little bro', she'll come over here, and we can lock the door like now. Is it a deal?"
"Yeah, but..." I was hesitating. He who hesitates.... I daren't let mum see that photo, as for my few friends...
"Okay," I agreed at last.

    Patty lived in London, only minutes from our college.
My big sister met her train at Woking station, and walked the mile with her to our home.
I was nervously waiting in Big Sis's bedroom. We'd fixed a date near the end of the holidays, when mum had gone up to London. Before leaving, Ayla had made a fuss of me, making me look as girly as possible.
I had complained loudly about the humiliation, but secretly I had actually loved her dressing me in her dark green silken panty, then her matching bra, which needed a teeny bit of padding.
"Wow," Ayla admired, "I'm so jealous of your soft smooth skin, perhaps you were meant to be a girl?" she had  giggled.
I blushed. She gazed down to my little willy, slightly bulging under the panty. She shook her head. "Well, perhaps not...."
Then she had covered me with a frilly pale green dress that I had never seen her wearing. It has numerous frills, and was lined with a frilly dark green lace.
After admiring her handiwork, I was left alone, feeling an odd mixture of pleasure and anticipation, mingled with an indefinable overriding fear.
I hear the front door open, and girly voices fill the house. Mostly it sounds like they are laughing excitedly. 
I hear steps ascending the stairs, and I tense up.
Will sis win her bet? I hope so, for my sake. Will Patty think my hair too short, for I don't think it looks very girly. Oh, I hope this nightmare could soon be all over.
A tall girl, three inches over Ayla, enters the bedroom. Dressed in a black pvc skirt, and a white top, she looks almost like one of our lecturers, only a bit more tarted up.
She immediately comes over to where I am sitting on Big Sis's bed.
"So are you Ayla's little brother?" she queries, scanning me with her deep searching eyes.
"I'm Terry," I reply. Big Sis had ordered me not to say too much, though really my voice is hardly that of a 19 year old lad, it is much more feminine sounding.
Patty looks bemused at Ayla.
"You're kidding me," she says breathlessly, "I suppose Terry can be a girl's name. No she's a girl, no question!"
"Then I win the bet," laughs Ayla.
"No, sorry Ayla, but you can't trick me. I wasn't born yesterday."
"Well, this really is my brother, you know!"
She whisks up my sissy dress,  and before I have time to protest, pulls down my lovely panty.
Patty gasps.
She shakes her head in disbelief.
"But, you're so...." words seem to fail her.
I hastily cover up my little private part, and ask the question that had long been occupying my mind.
"Please can I have your phone now, Sis?" I beg as politely as possible. 
 Big Sis obliges, and continues,
"So I win!"
"You sure do." Patty hands over the cash with  smile. I locate the offending photo and delete it. It was quite blurred, my face hardly recognizable, but though I feel half cheated, I am too relived to complain.
Click!
Patty has taken my picture! Me, in my frilly sissy dress.
"Gimme that" I cry, jumping up. I do feel cheated now.
But Patty passes her phone to Big Sis, as I round on her, then  it is a teasing game, them giggling uncontrollably, as I vainly attempt to grab the phone from them.
"Look, you promised...." I moan to Big Sis, once I saw I couldn't grab the phone. But I am waiting  in case an opportune moment should arise.
"Oh, I did," laughs Ayla.
"- but I didn't!" jokes Patty.
"Look, be fair, you've had your fun. Look, I don't mind wearing another dress, if you like, only, please no more photos."
"Oh, I think this one will do," answers Patty. "I'll give it you back if you do one thing for me."

   So half an hour later you could have seen her taking me to the station.
I was in my normal clothes, you understand, walking hand in hand with Patty as though we were just another couple on a date.
Only anyone who knew me would have been amazed, as I never went on a date with any girl before.
I had failed to find that chance of grabbing her phone in the bedroom. She had kept it in her hand as she outlined what she expected me to do.
"I want you to come to my flat, and let me fondle that lovely little cock of yours!"
"That's two things," I objected.
"Well sort of," she agreed, as Big Sis gave another of her giggles.
"I'll go to see your flat," I proposed, "that's one thing and I'll agree to that."
"Oh, no my little one, I'm the one to make terms. If you don't agree, I'll add some more demands!"
"Oh yes, how about making Terry wear these clothes to your flat?" Ayla suggested brightly.
I shook my head furiously. What was I to do?
I tried snatching the phone from her hand, but she was too strong for me. I groaned in despair.
"That was silly," she scoffed at me. "Are you wanting me to put your photo on the net?"
"She'd do it too," added Big Sis.
"Look, if you agree," said Patty in a seemingly more conciliatory move, "I'll let you carry my phone."
I look at her surprised.
"Then you can delete the picture as soon as  you've let me have that feel of you."
It seemed a chance at least.
Surely I'd get a good chance of slipping away from Patty. 
So that's why I consented, and why she was holding my hand as we entered the station.
"Terry!" it was mum, just emerging off the London train. She stared at me in amazement.
This tall girl with the tarty pvc skirt was then given her attentions.
"Terry, who is this, where on earth are you going with such a girl?" she gasped. I couldn't blame mum.
I was trying to frame my excuse, on the lines of it's not at all what you think, when Big Sis came up behind us.
"It's all right, mum," Ayla laughed, "this is my best friend at college, Patty. I'd just stopped off at the chemist, we're gonna show  Terry some digs that have just become vacant near  Patty's block."
Mum seemed reassured by Ayla's presence. She nodded and left us.
"Phew!" laughed Ayla, "that was close."
"How you get here?" I asked her.
"Oh, I was following, just as well really. We had an idea you might try and give us the slip...." 
"I don't want you to come," I objected.
"What you want don't matter," said Patty firmly. "You  coming? The train's coming in."

   The three of us were walking hand in hand out of Waterloo station, past the college to where I journey daily from home. I had found the daily journey very tiring, and Big Sis had suggested that she try and find digs for me near where Big Sis stays, and near the college. Mum had surprisingly agreed, and  Big Sis had been asking around during this vacation. 
So her story to mum had been plausible, but I knew it weren't true.
I had had no chance to get away from them. I had Patty's phone in my pocket, but they had iron grips on my hands. Once, when we had to cross a road, I tried pulling away, but they evidently guessed my intentions. 
Now we were in a seedy street, a mix of shops and old houses converted to bedsits. We must be getting near. I was panicking.
Their hands grew tighter, as we passed a dingy looking place with bright lights and pictures of girls all round the flashing signs by the entrance.
Surely this wasn't our destination?
We carried on past.
Next door was the first in a row of nineteenth century terraced houses, and I was all but pulled into here. This was our goal!
We made our way along a dark corridor to a downstairs back room, which Patty opened with a smile.
"Here you are my little one!"
The room was a mighty contrast to the corridor, bright and spacious, an ensuite in one corner, a curtained sleeping area along another side, around a central living area with colorful contemporary furniture.
"Ayla's not watching?" I asked nervously.
"Oh no," Big Sis smiled. "I'll relax on the sofa while you keep your promise to Patty." I guess she also meant, to make sure I didn't slip away. She let go my hand. But Patty had my other and was dragging me to the curtain.
I had no choice but to yield. Shut your eyes and it'll soon be over, I told myself. After all, she's not gonna hurt you. It was just that I didn't really want her to see me naked, 'cos I knew she'd not be impressed. So with a swallow, I allowed her to pull me behind the curtain, where was revealed a large single bed with a pink silken bedspread.
"Lie there," Patty commanded, letting go my hand at last.
I lay down, scared, yet also in my heart of hearts, quite liking the attentions she was bestowing on me.
"Right, let's get those socks and shoes off quickly. Now that shirt, shall we?" Patty began her stripping of me, as I shivered. I had a feeling her loud voice was for the benefit of Big Sis.
"Oh yes," she laughed, "I've never seen a man so smooth! And you are a man, I can see that under your panty, can't I?" She was talking as though I were her little plaything. "Now let's make sure you are, shall we, little one?"
She'd whipped off my pants and pantie in a flash, "oh yes, you do have a cock, don't you? Though I must confess it's not the biggest I've ever seen!"
I mumbled incoherently, about my delayed puberty. She must have understood.
"Well, Patty knows how we can delay it further, or bring it on. Which would you like, little boy?"
Her hands were slowly approaching my willy,  interlocking themselves as they rubbed together.
"Well, Terry, do you want us to hasten your puberty so you can be like other young men?"
I wasn't sure what she was meaning, as her hand made its first contact with my willy.
"Ooooh, it's lovely and soft, Ayla. Sooooo soft and innocent."
I heard Big Sis giggle.
Patty looked at me.
"Thank you, Patty," I answered, "can I get my pants and give you your phone back now?"
She only laughed.
"Oh, yes, in one minute my sweet. But let your nice Patty fondle your cock properly first!"
As I breathed more deeply, she caressed my willy and called to Big Sis,
"Yeah, it's real soft, the foreskin's completely untouched."
I heard another giggle from Big Sis.
"So little boy, you haven't answered my question, do you want to delay your puberty any longer?"
Patty was fondling my balls now, rolling them between her fingers.
It was quite a pleasant sensation, and I suddenly relaxed.
In truth, I was not sure what she was asking, but my sixth sense told me that if I told her to try and bring on my puberty, we'd be here even longer.
His testacles feel so delicious," exclaimed Patty, as a warm feeling overwhelmed me. Her fondling felt 'delicious' too.
She was looking at me, awaiting my answer. I was lying back, abandoned in the pleasure she was giving me.  But I still wanted to get it over, so I replied,
"Stay like I am, miss," were my fateful words. 
If she looked disappointed, it was only for a brief second. Then she nodded as Big Sis was inexplicably crying out, "yes! yes!"
Patty handed me my pants, and I was half surprised when she allowed me to wipe the offending photo, which would indeed have shocked mum.
I returned her phone with my thanks, and got up to get dressed.

I could hardly believe it. It was over!
With a huge sigh I grabbed my discarded clothes and pulled up my pants. Thus, semi decent, I pulled open the curtain to reveal myself to Big Sis.
"I think you liked it," she whispered.
I think she was right, but was I gonna admit it? Never. All I had to do now, was make myself decent and take the train home.
My shirt was on when Ayla offered this:
"Don't you wanna see the digs I found for you?"
I'd forgotten what she'd told mum. I thought she'd been lying.
"Yes, it's only five minutes walk to the college, it's ideal."
"What here?"
I heard Patty laugh from behind the curtain. What was she up  to?
"Oh no, Terry," responded Ayla, "but it's right near by, should you ever wanna come and visit Patty."
Both girls laughed.
"Well, okay, can I see the place now?"
"Of course, you ready, Patty?"
"She doesn't need to come with us, does she?"
"Well, I've gotta be going, Terry, sorry. But Patty has seen the room with me, she'll take you."
Once again I began to feel uneasy.
"Look, Jana who owns  the property gave me these figures she charges for rental."
Big Sis handed me a scrap of paper. It didn't look too professional.
It read:
£150p.w. for one bedroom, shared use of kitchen and all facilities.  Alternatively £10 nominal rent.
 It sounded possible, can't be very nice can it? I didn't understand what the alternative was. Still it must be worth a look. I nodded to Big Sis.
"Okay, I'll tell mum," she said and departed before I had time to tell her that I hadn't agreed yet.
I waited while Patty prettied herself, then we left, via the empty kitchen and out the back door.
Puzzled, I followed Patty as we pushed thru a gap in the fencing to the back yard next door.
"Why we come this way?"
I called to her.
"Quicker," she laughed, and pushed open the kitchen door.
Inside a couple of girls, looking even more tarty than Patty were drinking wine, Patty greeted them like old buddies, and pulled me into the back corridor,  knocking on a door marked Office.
We entered when a high voice bade us come in.
"Jana, this is Terry. Terry, meet Jana."
I shook hands absently with this girl, as tall as Patty and oozing charm. her earrings tinkled as she moved forward and kissed me gently on the cheek. I was stunned by her shiny red pvc dress with lace ups all down her front, showing off her smallish breasts to advantage.
I think I was staring at them too much, 'cos she broke into my reverie.
"You'd like to see .... your room, then?"
I tried to say yes, but I was too overpowered by this dominating woman.
I did manage a nod, and Patty took me by the shaking hand and led me out the office.
In the corridor, a scantily clad blonde in only a bra and skimpy pantie passed us. My room was opposite the office, in fact the same location as in the house next door where Patty lived.
It was a very similar room in size, but the layout was different, a double bed in the centre of the room, covered with a plush maroon silk  bedspread. There didn't seem anywhere to sit, certainly nowhere to do my studies, the ensuite was in the alcove where Patty's bed had been.
"Feel the bed," suggested Patty, as Jana kept her eyes on me. Patty bounced on it.
Cautiously I felt the springs and agreed it was comfy.
I was about to ask if the bed could be changed for a smaller one, to make room for a desk, when Jana joined us by the bed and asked me:
"Patty tells me you're a boy."
"Oh yes, miss," I nodded.
"But she had thought you were a girl! I must say you look a girl to me too!"
"Yeah, I suppose my voice and looks are quite girly."
"Very girly," corrected Jana. "You may have noticed, Terry, that actually all the rooms are rented to girls here."
"Yeah, I had noticed."
"You really are a boy, then?"
"Oh yes, miss."
"How does Patty know?"
"Well, er...." 
The conversation was drifting into territory I had rather avoid. Yet even more I felt drawn like a magnet to this woman, who reminded me of my mum, only ever so much younger and ever so much more alluring.
"Oh I do know," explained Patty.  "I saw Terry just now, when he was in my room naked."
"Show me," she purred.
I froze, willing, yet scared. Patty hadn't mentioned my willy was so tiny. I didn't want this woman to despise me because of it.
I felt Patty remove my shirt for the second time, then pushed me on the luxurious bed, as Jana gazed at my shaking body.
Soon my pants and panty had been removed and I lay there completely naked.
She fondled my willy.
"Yes, it is lovely and soft," she was purring again. I lay there not caring whatever she did would be lovely.
"Patty tells me you want to keep your delayed puberty, if you can," she smiled at me.
I nodded my head slowly. "Yes, miss."
"Fetch the stuff, Patty."
Patty left us. We were alone. I with this beautiful woman. I was half scared, half excited.
She continued very softly feeling my willy and balls, uttering quietly to herself  under her breath words which were evidently of approval.
"Do you ever play with this?" she asked, pressing my willy a little firmer.
I was shaking my head when Patty returned.
I saw her hand Jana three tablets and a small phial, Jana took them in her free hand, the other continued fondling me so pleasantly.
Patty brought over a glass of water, then silently departed.
We were alone again.

   "These two tablets are to start your hormone treatment to stabilize and increase your femininity."
She handed them to me.
"You do want to delay your puberty as long as you can?"
"Yes, miss."
She gently guided my hand to my mouth and the pills popped in. What was I doing? 
"Then swallow them down," she handed me the water. 
They went down easily.
"Now one more pill, 'cos I can tell you like me fondling you, don't you Terry?"
"Yes miss."
"Good, then here's one more pill."
It was larger and it took a big mouthful to get down.
"That's a good girl!"
I looked at her. But she had no explanation this time. 
"Good girl!" she repeated and resumed her fondling as a kind of reward.
I relaxed once again and abandoned myself to whatever Jana had in store for me.
I felt her roll back my foreskin, which made me wince slightly. But she after inspecting it like a doctor, she rolled up the soft skin again.
"I'm just gonna spray this lotion on you," she told me, opening the phial. It may sting slightly.
"Wow!"
She was right, it did sting. A lot.
My little willy smarted and tingled, my balls felt like they had been electrified.
"That's good," she comforted me by caressing slowly my little willy, while her other hand soothed my forehead.
As the tingling continued, I began to find the sensation very delicious.
"So, you'd like this room, would you?" she asked. A needless question.
"So the only thing to decide," she went on, fondling me, "if whether you wanna pay £150 each week, or ten."
There must be a catch. I could see that.
"I'm not sure," I answered, "it's a lot of money."
"Not if you only pay £10 a week. You see, only girls are permitted to use this building. You'd have to dress...."
"as a girl," I completed her sentence. "But I can't attend college as a girl, miss!"
"You could say you've had the operation," she offered, but seeing my dislike of that suggestion tried, "look, as long as you dress in here as a girl...."
"Mmmm," I interrupted.
"What's wrong?"
"Oh nothing, miss, it feels so nice you feeling me like this!"
"Oh I'm glad you love it. Well I was gonna suggest you could change next door in Patty's room. She'll agree to that, because she often works in here."
"In here?"
"Yes, I can tell you that though we charge a nominal £10 rent, you can earn a lot more- we take a percentage."
This was too good to be true.
"All you have to do is entertain our clients...."
I suddenly clicked what she was offering. This was the place with the pictures of all those alluring girls outside!
She spotted my sudden shift of mood. I felt her rubbing my willy more firmly and I felt that delicious sensation overpowering me.
I felt my little willy become harder and somehow bigger.
"That's what you want isn't it?" she softly purred. "never tried it before have you?" Let your Jana show you. You can enjoy all this and get paid, and I am in the room opposite whenever you want me...."
I was shaking with excitement now as her pulsing my willy became more and more intense. I couldn't say no to this alluring woman.
I was nodding eagerly as she lowered her mouth lovingly down to my big willy.
"Then seal the deal, big boy," she cried.
"Yes miss," and I splattered out  my foaming liquid down her eager throat and then dripped over her smiling face.

  THE END
Last Post
55,721 views
1 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
 
Add your message here..
 
bill19192005
More please, more! 
Reply
Quote
What kind of post would you like to make?
Topic
Video
Audio
Image
Story
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.