Decisions, Decisions, Desissyons
How I began …… as a siss’sister. Some are born girls, some achieve girlhood, some have girlhood thrust into them. An adapted quotation. Ooops.
My nipples were rock hard. My groin pulsed with heat, a sensation I’d never felt before. I knew what an orgasm usually felt like. This was so different. My whole groin was warm, it felt moist. Strange – but wonderful too.
His hands stroked my back and flipped the clasp on my bra. My tiny breasts escaped from their silk and satin nests and two thirds of their content fell away. I heard the ‘huff’ of surprise …… and waited ….. but his hands continued to stroke. They wandered to the front and cupped my small excited breasts in two new cups made of warm hands and gentle fingers. It was wonderful. His hands stroked, caressed, slid downwards. At last one hand reached my groin, cupping my tiny stiffness while the other held me to his body and his hard, huge maleness while continuing to squeeze and stroke my nearest explosive nipple.
How had I got to this place, this situation?
When did it all start? Well, I knew the answer to that.
I was just sixteen. Two years ago now.
Mum and Dad and the two big sisters had gone out. I had been left a pile of jobs to do. One of them was to put away the ironing that Alli had finished but not had time to put away. For the first time in years, their private ironing, their fancy underwear rather than their day-to-day varieties, was part of the job. I had never really noticed their things before. But some of these were so pretty. I sniggered – putting their drawers in their drawers. But I knew what I was dealing with were neater, prettier, girlier – not drawers – but panties. And bras too. Lace and satin and silk and, just lovely. I held them in my hands and enjoyed the feel of them. One by one as I put them tidily into their drawers. And I saw the quantity, the variety, the colours, the silkiness, the smooth, soft, excitingness. Then I wondered what they would feel like being worn right, not just being fondled.
Then I found a pair of, well, not panties. These were loose-legged but still with lace and lovely sleek material. Now I know they’re called French knickers. They looked as if they would feel exciting in some way – but different from the snug fit of the panties I was already interested in.
The first time I put on an expensive pair of panties instead of the cotton ones I was used to. Those satin and lace creations had hooked me. They felt SO good. I think that was when this had started.
Over the next weeks, I got more and more excited. It was almost an addiction. I thought about panties all day, every day. I wanted panties of my own. I wanted ….. so I bought panties – for ME. And I wore MY panties. And, lo, it was good. (see the benefits of a Christian education.)
And verily, I went forth, and when accompanied by siblings or mother sadly spent time wandering in the wilderness away from the beauties of the lingerie departments where I would feign be – until I was alone and the need for pretty things overwhelmed me and I gave into temptation. And I bought more panties and my first bra and my first stockings. Weren’t suspenders and clips difficult at first?
Gradually I accumulated a tiny wardrobe. I hid it under the floor of my own wardrobe – a four-inch space. I had to hope that the noise as I lifted the board was not noticeable.
And in the next months, I hope that none suspected. I wore panties as much of the time as I could. Nearly being caught by mischance and wicked opportunity – but good fortune was on my side and I believe ‘they’ never noticed.
That night two weeks ago, I went back to my apartment. I was now living in a micro-flat at the house of a friend of a school-teacher. I had seen the small advert on the noticeboard and applied. Fortunately it was a mile or more from home and served a different school area – so very few people knew anything about me. So I was able to be Olivia more of the time – instead of being dull Dan.
But not all secrets can be kept forever.
I wanted more than just me enjoying the feeling and the excitement. I wanted to share it. I wanted other people to enjoy me looking this good and feeling this good.
And then it was just a short step, well, giggle, a sway and a swish and they were feeling ME. It was fantastic. Stroking my own hands up my stockings or across my satin-pantied bottom was, excellent – Thanks Mr Burns. Even if I couldn’t do the hand gesture single-handed.
But when someone else did it – that was so much better.
So here I am. At the Club. It’s a very, um, selective club for people with a special interest in clothing and so on. Oh stop pussyfooting around, silly boy, I tell myself.
Okay, it’s a club for sissies and men or even women who love them too. There are limits. Skin to skin contact is discouraged – but fortunately not forbidden.
I’ve only been here a few times. I was so lucky to be in the lingerie shop buying some new bras when Lady Prendergast came in. She knew instantly what I was and gave me a card for The Club.
I was SO nervous that first time. One of the other girls saw me and came straight over. “It’s your first time, isn’t it?, she giggled.
I was too busy admiring her breasts to answer. Then she tipped my chin with a long red-nailed finger. “Look here, darling. Even if you’re just admiring. Even if you’re thinking that you want boobs like this for yourself.” Another giggle.
“How ….”
“You’re not the first pretty-boy to come here you know. And I mean ‘come’ “– and her hand brushed across the front of my tented skirt – and I almost did!!!! “But you’re very pretty. Almost girly enough to, well. I mustn’t say too much or I’ll be punished. And I might not like that.”
“Is it that obvious? I mean that ….”
“Only to those of us who know, darling. And what’s your name, your girl-name?”
I’d never really thought about it – but instantly I chose my new name, Olivia. I loved her drawings and had pages of them stored. And Christeen. And LatexAndy.
That was the first night. Adama, that was her name, introduced me to quite a few people. I enjoyed them seeing what and who I was. The first people I met were the other girls who worked at the Club, the barmaids, waitresses and servers. And, what a surprise, almost every one had a name like me. Paula, Patricia, Carla, Charlotte, Denise, Roberta, Robette, Sandy, Alex.
And, eventually, I let one of the men hold me to their side, and stroke my bottom, and my thighs, and my side-boob and, well not quite all over.
That was Rojer. A Scandinavian, he said. I didn’t care. I was just dazzled by his interest in me. I didn’t remember anyone caring about me the way he said, the way he, um, demonstrated. At one point, he took my hand, my long thin glittery fingers held in his big strong masculine paw, and pressed it to his trouser-front. I gasped at what I felt there. So BIG. So interesting.
I went back a few nights later. Not the next two because Rojer said he wouldn’t be there. Did that make me an easy target. I don’t know. I didn’t really care. I just knew that I was eager for more attention from him.
But he brought some friends with him. They sort of surrounded me. Keeping me captive in a prison made of their legs – all pressed together leaving a little room for me to turn and tease.
They made a game of it. Pushing me from one to the other. Making me wobble and topple on my not-very-high heels. So many times, I could only prevent myself from falling headlong by putting my hand on their, er, thighs, or nearby. They smiled and I giggled each time.
I tried not to drink everything they gave me. But what’s a guy to do when they’re being so generous. Fortunately for me, Rojer told me to stop when I had drunk the second one. He told the others not to tease me. “My pretty one here is so young, so tender. It would be unkind to make it too easy by making him too drunk.” And he turned to me and whispered, “Do you want to be my pretty girly-boy or pretty-boy?”
I blushed and giggled yet again, “Whatever you would prefer. I just love being with you.”
Rojer was so kind when I said that. He replied. “Sweetie, I’m the first man who has noticed you here. It may be that a stronger man will claim you – and I will have to let you go. But in the meantime, I’ll think of you and treat you as a pretty-boy – as you are indeed so pretty and still a boy.” And his hand stroked across my front, giving a little squeeze too. I felt that squeeze all the way from my hard, hard (mid-size) penis to my heart and to my soul and to my brain. And everybody said ‘MORE’.
If I could have gone brighter red with excitement and embarrassment – then I would have done. Instead I squeaked because one of the others, Frank, gave my bottom a squeeze just at the same time. That just added to the excitement and the certainty that – in this place, here and now, I was attractive and wanted.
After a while, by mid-evening, I was barely able to stand and was perched on Rojer’s knee. He held me tight by my waist. I felt so comfortable, so relaxed.
Then he pulled me gently towards his lips and kissed me like I had never been kissed before. Alright, more truth, I had barely been kissed before. And never by a man like Rojer. I loved it. I loved him. I turned within his arms and dedicated my lips to his. My hands went round his neck as if I was welding my mouth to his. Tongue snaking against tongue. Never was there a kiss like that. At least one of the other men in our tiny circle sighed as Rojer got his reward.
Rojer’s comments made me think. Next time I went to the club I arrived early so that I could talk with Allison, one of the girls I had really felt a rapport with.
We talked for such a long time. Even after the clients began to arrive we kept talking. Until Rojer came over to me and asked if he might interrupt. I didn’t really answer but jumped up and cuddled him instantly. It was a sort of answer without words really.
He smiled and hugged me back. His strong arms went around me and he lifted me off the ground as he held me tight. I could feel his wonderful penis grow hard and solid as my front-bottom pressed against him. Even though I had never seen it and only felt it once before – I knew it was hard, male, eager, longer than mine, thicker than mine, needier than mine. And with the little brain it had, it wanted me.
I sighed with pleasure as he bent his lips to mine. Then his hands tightened and he pressed me even harder into his truly man-sized groin. My own tiny groin shuddered with a tiny heat – as if I was having a tiny orgasm.
Rojer grinned, “Well done, sweet boy. Your first sissygasm if I’m correct.”
It wasn’t the same as a boy-cum. I was used to them. But my panties were wonderfully oozy and damp. And the perfume of my excitement spiralled to my senses.
I would never have guessed that such a thing was possible. But it was gorgeous, wonderful, more satisfying somehow than the wank-type outpourings I managed by myself. And without being touched. I wondered what it would feel like – skin to skin.
I think Rojer guessed. He smiled even more broadly. “Sometime soon we must find out how well we, um, get on together. I’m looking forward to more than kisses, you know.”
I swooned and tucked my head into his neck. He smelt wonderful. Manly, Inviting. I felt so delicate next to him. Skinny, small and vulnerable next to a true man.
What came next was the hook that drew me finally and completely into my new life. He touched me.
It was so fantastic as he first touched me properly, y’know, the way that a man touches a sissy. At last he put his hand on my, well, I call it my front-bottom like some children do. I jolted with shock. I’d never had another hand placed there. Not like that. With a masculine firmness. So different from playing with myself. Doing it myself, even at times of maximum relaxation, I was always going to know what my hand would do next. But another person, another hand, so different. So nice.
Then he gave a little pat, and a stroke. And everything in my world jolted. I jerked in his hand as my sissy-sperm splashed into my panties. If being touched was so wonderful, then having my first man-touch orgasm was enough to make me want this life forever.
We spent a lot of time talking that night. He wanted to know about me – the real me. The one who had been hiding for so long. He tried to help me decide what sort of girl-boy-sissy I actually was.
What did I think of my penis? Did I love it? Did I want it gone? What sort of things did I like doing? Or having done to me? Innocent?! I was as naïve as a ….. well, fill in your own guess! I thought more about myself than I had ever done. And he refused to let me have more than a coupe of sips because he said it was so important that I knew who I was – and where I might be going.
Rojer was such a kind man. He knew so much about the needs of sissies and how they differed from each other. Now I know that he was, in fact, a sort of catcher and trainer for The Club on behalf of more senior, more experienced people.
But knowing what I know now, well I’ve never stopped loving him for his kindness even if there was some subtle, to me, indoctrination of as they now call it grooming. I was a new, young, eager sissy and I wanted more of the attention, the affection.
But, as I said, some secrets come out to play when you want them to stay neatly hidden in the safety of darkness.
It was sister Anya who found out.
No – no cliché. She didn’t come to the club for some escapade of her own. She wasn’t tracking me down to see what awfulness I was doing. She just wanted to see me. She came to my tiny little apartment. And she saw no evidence at all of a boy or a young man living there. She peeped through the curtains and saw – well, let’s be truthful, scanties and undies and dresses and all the things that an eager young girl or her somewhat-male sissy equivalent would need for a life of leisure and pleasure.
So she waited, just around the corner until I got back from work – yes I had a job as an office gopher – and was aiming to get ready for an evening out. Not, on this occasion, at The Club but an ordinary evening out for Olivia.
I’d been in for nearly half-an-hour when the doorbell rang. Being a sissy and therefore at times of maximum sissyhood a bit dim, I opened the door. There was I in my yellow and cream undies facing my sister. I don’t know what she was wearing.
She gasped. She began as if to run away. Then stopped. “So all the borrowing of my things, it’s made you gay has it?”
I was appalled. She had known! How? When? For how long? What about the others, Mum and Alli.
“No. I’m not gay. I just love undies.”
“From where I’m standing and looking at the way you’re dressed, it’s a lot more complicated than just wearing undies now and again. Just the undies are expensive. But those look like top-quality artificial boobage and those are really expensive and even more so as they fit you properly. Not like most cross-dressers I’ve ever met. Tell me more.”
It was a command – but it did not have the power and weight of a man, a real man, behind it. The confidence that Rojer had given me allowed me to get back control of the situation. “Well, there’s a surprise. Hello, Anya, come into my little abode. D’y want a coffee or a tea maybe?”
“I’ll have a tea, please, jasmine if you’ve got it. Then I want to ask a number of questions of my, erm, are you my sister? I think not. I’d guess you’re more of a girly-boy or even a sissy. Am I right.”
I was in control. “Yes, you’re right, Anny. I’m a sissy now. And I love it.”
“Don’t you think we ought to know. We are your family. And we do love you – even if you seem to have moved off and split somewhat in the last year or so. We know you’re still alive – but not much else. Are you, so to speak, a sissy forever now. Is that going to be your whole life – or just evenings, weekends and so on?”
“At the moment, I’m a sissy when I want to be. I know there may come a time when a Master tries to make the decision for me – but I have no intention of going that way. I know that sissies get old. And an old sissy has very little future. Unwanted, uncared-for, replaced by younger sissies. Not a pretty picture.”
“Sooooo – tell me how you’re going to avoid this fate. Have you enough willpower to stand up to a Master, or presumably to a Mistress? Tell me the last time, tell me the first time you said ‘no’.”
I squirmed and mumbled, “I nearly, no I did say stop last Saturday.”
“And did he stop? Did you say stop again when he didn’t stop?”
“Well, actually, yes I did. But I did give in a while later.”
“So, your tough-sissy approach doesn’t really work, hmm?”
“What can I say?”
“Oh, that you’re just a silly-billy sissy with not much in your head and even less in self-control. And I know that you’re tougher and stronger than that. I’m not letting my little bro – or even little sissyster be made less than she can be. You’re going to need help to avoid going all the way down the sissyslippery slope. We’re going to have to work together.”
“What’s all this with adding ‘sissy’ to words?”
“Seemed rather appropriate to me, kinda clever too. Sissyster means my sissy sister, duh.”
“Mrhggmph.”
“Was that a grumble, some sort of complaint, criticism, hmmm? I’ve got a cure for that.”
And shortly after, my mouth was plugged with her fresh warm panties and a garter-belt stretched to hold it in place. This time when I tried to say ‘mrhggmph’ all that could be heard was something similar like ‘mrhggmph’.
I was actually really excited by this new feeling. I could tell because my tiny sissy-clit was straining for release. I knew that if I could just rub it a little then I would have a humungous and really satisfying cum. But as well as my mouth, my arms were tied and my legs were tied. I couldn’t even rub my thighs together in a no-doubt hopeless attempt to frott myself. I was in agony. And it was wonderful.
It felt like I had to wait hours for Anny to come back. I heard the telephone ring while I was, um, ‘tied up’. I knew that I’d have to be careful how I answered the phone next time. Telling the truth had obvious difficulties. Lying could be worse. Being ‘unavailable’ was not what Sissies were supposed to deliver. Very much wrongo.
But what Anny had said did make me think. I realized that I had been dazzled by people being interested in me. They had groomed me. Obviously I had been a very willing participant. I giggled ‘participanties for me’.
But, how sensible was I being? What was the future if I did continue? What was my future if I stopped? Abd who was I going to get good advice from? Rojer? – don’t be silly! Anny? – maybe. Myself? – don’t be silly! One of the girls at the Club? Doubtful – every one of them had their own plans.
What was I going to do? What did I want from life? Being a sissy had some advantages but so much of this would be in the short term. What was the expectation for an OLD sissy? Was a sissy like me actually capable of competent thought – or was I a bimbo-sissy too. I licked my lips – so nice. shifted in my chair and felt my breasts rub against their satin comfort – so nice. I felt my minicock as it was squeezed by my thighs – so wonderful.
Could I give up all the pleasure I was getting now – for something vague and in the future?
END
