"Oh I know you will, sugar"
Desperate to avoid “extras” for failing to demonstrate full girlish submission when being disciplined “Cindy Sue” arched her back to “accept” the paddle as it descended, kept her sexy pins apart so that her “cute” little pink plums were always on view, kicked said pins to show girlish helplessness and then emitting a series of escalating “ohs” and “oh Ma’am please” followed inevitably by tears and floods of tears. Yes Cindy Sue knew to get to tears as quickly as possible, no tears mean certain extras with the strap and the strap was pure agony.
Sore isn’t it Sweetie!! She tapped the paddle against her palm and continued, “and then there is the strap, tawse I think the Scots people call it, and the crop, much much more painful I can assure you. Any more silliness and we will move on to those”.
“Please Ma’am no more, pleaseeeee”, I’ll be good.
“Oh I know you will, Sugar”, she picked up the panties and dangled them at the end of her finger ………..
Naked, I had just experienced another long hard session with Ma’am’s paddle and it was agony. She was exactly the sort of woman I had fantasised about all my life, tall at almost 5.11 without heels and large - actually fat but not obese – but well proportioned and not the least bit afraid of displaying her womanly curves for full effect on her male victim.
I on the other hand am a wimp, terrible to admit but true. Now almost 25 I was barely 5.3 and small even for that size. Not only that, I had hardly seen puberty and consequently had very little body hair and an embarrassingly small willy. I knew that in the wrong clothes I could easily be mistaken for a girl and consequently had a terror of being “put” into feminine attire.
My small stature meant I was “protected” by my mother by being home schooled and precluded from having male friends, according to Mummy they were always just too rough. Girls too were invariably unsuitable. So until she passed away when I was 19, I spent my days at home very firmly under her thumb. The slightest sign of revolt was met with first a paddling and then straight into one of my many sissy outfits. The rest of the day was then spent doing exactly what I was told, when I was told it. My sole aim to at all costs avoid another paddling by pleasing Mummy. She also had a maid’s outfit for me which went on for her weekly “just us girls” evening. It was short and very frilly and invariably accompanied by tights and heels. As she explained it to the girls, I was a sissy and she did not have the heart to deny me at least on some occasions. I was on my very best behaviour, embarrassing Mummy in front of her friends always ensured a very painful paddling.
That was not all though, you see being in sissy mode invariably made my little nub rock hard which Mummy was well aware of. So it was “on your knees girl” and “lift your skirt and show me your panties, NOW GIRL” followed by a smirk and “why you fight this I will never know, you are a natural…... Now understand this sissy boy, if I catch you so much as touching yourself never mind engaging in that disgusting boy habit that girlish bottom of yours won’t be able to sit down for a week. You my girl will be pretty, eager to please and pure”.
“Well what do you say to your Mummy”.
“I promise to be your good girl Mummy dearest, thank you so much Mummy dearest”
Imagine my reaction then when I was left a fairly significant legacy. I broke out and of course having little or no life experience fell flat on my face. My “no brainer” investments in, guess what property, wiped out my legacy in jig time and so I was now totally dependent on my job as a lowly administrative assistant in Ma’am’s PR consultancy. Unusually it specialised is serving only the burgeoning black business class,
Why she had hired me I initially could not fathom, on my part it was simply that I was besotted by her. Like a lot of heavy but shapely women she was well aware of her effect on a certain type of man. Fully made up on all occasions, her sexy business suits invariably included above the knee skirts and were always accompanied by high heeled court shoes. The twenty or so staff were equally divided between women and what I took to be effeminate gays, both groups strangely all white. What little respect I had from either vanished once I was “promoted” to being Madam’s personal assistant. It happened after one of the “men” started hitting on me and was, according to Ma’am for my own protection. This was not so very unbelievable as it was an unusual office to the say the least. One evening instructed by Ma’am to stay back to work some overtime I heard alternating slapping and whimpering noises from her office and peeked in. There is the twilight I saw Mr Terri, one of the prettier gays, fully en femme and flat across the desk with skirt up and panties down being manfully stuffed by a client who had been in with Ma’am earlier in the day. The paddle on the desk, the obvious cause of the earlier slapping noises, was ensuring full cooperation while a large gag held his mouth in a pleasing “O” and left his only sound a gratifying whimper after each trust. Just before backing out I momentarily caught Terri’s eyes as they glazed over, it was quite obvious that, while she may not at first have been a willing participant, she was being brought to a fine appreciation of the pleasures provided by a dominant cock. That this very burly black man was well hung was evidenced by the very pronounced wiggle in Mr Terri’s walk for the next few days. I also noticed that he barely sat down during the whole of the following day. What was most disturbing to me however was that watching poor Terri submissively taking black cock up her pert bottom left me rock hard and unable to get the scene out of my mind. Was I the “ natural sissy” Mummy said I was?
I found out subsequently that these events were by means unusual, in fact whenever any of the pretty boys annoyed Ma’am in some way this was likely to be his “punishment”. Also it was well known among the black business community that Ma’am’s clients were assured a plentiful supply of sexy white ass.
So for me now as her PA it was: get Ma’am’s coffee and exactly the way she liked it, collect that night’s outfit from the cleaners, ensure that her feminine hygiene cabinet was always full and go and purchase tampons at her time of month. I thought it couldn’t get anymore embarrassing but guess what ……… I finally managed a revolt when my annual review “training plan” referred only to courses in manicure and pedicures. I even thought I had won a small victory when Ma’am seemed to back off and very foolishly bragged about it in the office. I should of course have realised that she was only biding her time. Given instead more responsibility in the form of her bank accounts, well you can guess what happened.
The court case was just awful I was petrified of going to jail and would commit to anything to avoid it. The judge who I suspected knew Ma’am was female and initially feigned sympathy for my predicament. She appointed a female parole officer to explore options other than jail itself. Here there was no ambiguity - this lady did know Ma’am, was a very close friend in fact. So it was no surprise when she proposed that I continue to be Ma’am’s personal assistant but in addition was to become her 24/7 houseboy. She giggled at the “boy” bit, just why I would very soon find out.
Being so naïve I did not realise just how strange the court was. I mean how many courts include a cage just high enough to allow an average sized man to crouch in, is staffed solely by females not excluding even the police officers, and presided over by a seriously sexy judge.
Incredible as it may seem the three female officers had even taken a strap to my bottom in the cell prior to my appearance. This supposedly was to make sure I showed the judge her due respect and so during the whole process I was naked on my knees, head bowed and arms folded behind my back.
Neither was I allowed to offer any formal defence, just a statement in mitigation after being found guilty. During this Madam Justice never even looked at me, her concentration being solely on her nails. I asked for this being my first offense and that I had fully cooperated to be taken into account. Continuing to inspect her nails for seemed like an hour she simply said “denied”. Desperate after sentence had been pronounced I followed with a plaintive “oh mercy please please madam” and “thank you madam” when she again responded “denied”.
The sentence was ten years suspended for five while I was placed under Ma’am’s sole authority. It was made quite plain to me that I was hers to do with as she wished. She could at any time request that I be taken into custody to commence the full sentence and at her sole discretion impose an additional ten years.
I was now ordered to be placed in “sissy” irons made from reinforced pink plastic. First I was handcuffed behind my back, placed in leg irons and gagged. Then one of the officers brandished a chastity belt into which went my penis and balls with the key placed in Madam’s hand. Finally I was collared and a chain connected from it to both my handcuffed arms and the leg irons. This was so short I could only crouch even while on my knees. Now one of the officers produced a crop and literally whipped me towards what seemed to be a low table covered to the floor by a heavy black cloth. However as I shuffled forward the cover was lifted to reveal that it was in fact a cage, into which I was forced and the small opening locked with the key once again handed to Ma’am. Forced into a low crouch, gagged, manacled and caged I looked out at Ma’am, Madam Justice and officers chatting amiable as if I did not exist. Shortly however Ma’am did turn round just long enough to view her new possession and, with a wave of her hand, indicate that the covers were to come down. As they did I for a moment caught the triumphant smirk on her face.
And so to Ma’am’s very large and opulent private residence where once again I was naked with throbbing red bottom and facing what I had always dreaded most. Once again, as with my mother, it was on with the panties and then the white opaque glitter tights.
“OK Sweetie now I want you up on your tippy toes and do a twirl for me but first hands on your boobs, girls never leave their boobs exposed when they can avoid it” and so with hands over my nonexistent boobs I went up on my toes and did a slow twirl.
“No no! Arch your back and hold your tummy in, it will give prominence to your bottom and you really do have a gorgeous girly bottom”.
And so off I went again, on my toes and once again hands covering my “boobs”.
“Mmmm very sexy, you are such a lucky sissy to be so so tiny in front, no need for any adjustments there. I think a panty liner will do the trick” She pointed to a pack and I took one out.
“OK now honey you just press the sticky side to crotch line of your panties.” She was treating me as a complete airhead.
“Good, now let me see. Oh yes a lovely flat feminine vie, sorry sweety but another rule for you to remember, you always always wear a panty liner, understood”.
“Now those lovely ankle boots over there put them on” – they were pink leather with a peep toe.
“OK, now honey round you go and let me see your bottom again” I was beginning to think this would never end.
“Oh honey those heels really do it for your pins, so so sexy, all sissies love the effect and so will you. Walking in heels is almost an art form and you girl will learn it”
“Now I want your knickers and tights down, hands back, bend and spread your cheeks for me”. At this point, just for seconds, I was tempted to rebel but quickly remembered the agony of the paddle and the court.
So now I was bent over, hands holding my hot pink bottom cheeks apart, the whole picture framed by my knickers and tights bunched prettily around my thighs.
“Yes very nice botty indeed, so girlish you lucky sissy” and then continued almost dreamily, “just you wait ‘till you’re having lovely girlish things done to it, sissies can never get enough of that”.
“We will have to have your nails done regularly however, varnished feminine nails with that pose and some black hunk and you won’t be able to sit down for a week”.
“So sweet cheeks, another rule, I want you hairless down there at all times, I warn you just one hair and you will be red raw, and moisturise of course every morning without fail, understood?”
“Yes Ma’am”. At this point I couldn’t help but recall the scene in Ma’am’s office where that gay boy on the staff was being royally bum f…ed and felt a deep dread as to where all this was leading.
“Now lets see the other heels and smock on you…” These shoes were mary janes with a two inch block heel and the smock came to just below mid thigh. Ma’am however was not about to stop rubbing it in.
“Oh don’t look so glum, I know it’s not as short as you would like but you do after all have to do some work between teasing the boys. All sissies are dreadful sluts and you will be no different if let I’m sure”.
“You however Honey will be ladylike, by which I mean no flashing of your pretty panties or it’s spanking time”.
“The heels” she continued “are pretty but practical for standing on all day. They will also prepare you for high heels which you will be wearing to work whenever we have clients calling. You will also be glad to know that your smock for those days will be a much shorter”. “The no flashing of panties rule will be relaxed then also but more of that later”.
“OK now listen up girl, in case you don’t know what you are wearing is a stylist’s and beauty therapist’s smock, it and others like it will be your everyday wear from now on. Your place in my private life and work will require these skills - you will be acting as personal assistant both to me and all the staff in the office. Training will start shortly and I expect 100% effort, Madam Charlotte who you will meet shortly is an experienced sissy trainer and moreover has my full permission to discipline you when and however she sees fit. She is a stickler for details and I assure you that no sissy has emerged from her clutches other than feminine, complaint, submissive and obedient”. And so I did.
It was some months later and I had long since discovered that Ma’am’s clients had very specific needs, needs that her staff were required to indulge without the slightest objection. To the contrary we were the blonde airheads – I was long since strawberry blonde – giggling and teasing non stop. Ma’am had said that when clients called my smock would be shorter and it was very short. Gone too were the “sensible” block heels – now it was sexy ankle boots with a very thin high heel. With no tights my long tanned legs were displayed sexily having been moisturised to a sensuous satin sheen. Oh Madam Charlotte’s training had rendered me one very effeminate sissy, well schooled in pleasing my man of the moment.
This party for “special” clients was at Ma’am’s private residence and well before it we girls had been put through our paces. It was akin to a military briefing at which targets were allocated and it was made quite plain anything less than an excellent report would have dire consequences for us. My “target” was a gorgeous hunk of a black man very nervous as this was his first time with a sissy. Having very obviously licked my lips while looking at the OMG very large boner in his parts I was now leading him to one of the available bedrooms, making sure to walk a few feet ahead so that he could enjoy my long legs and wiggling bottom. Once in the room it was arms around his neck and “Please be patient sir, I’m very new at this.” He just picked me up and carried me to the bed, depositing me on my back.
I had no idea I’d become such a slender waif that I could be picked up and helplessly deposited like that! Opening my blouse he turned me on my side, unfastening my bra. Removing it he returned me to my back before he climbed atop of me and mouthed one breast, then the other. My nipples had really become sensitive!
My back arched in surprise and he laughed before smothering my heavily painted mouth with kisses, and sticking his tongue practically down my throat. I found myself getting hot and didn’t try in the slightest to resist.
Pulling away and after removing his slacks and underwear he knelt on the bed himself motioning for me to come near. He was fondling his very large penis and I knew instantly what was expected of me.
Tentatively I crawled to him, positioning myself yogi style before taking him first in my hands and guiding him into my mouth. I began to suck, lick, and fondle his penis and genitals. I slurped it in and out of my mouth as Madam Charlotte had taught me. I paused to take it out, kiss his balls and look up into his eyes sexily. He was already quite big and as I sucked him off he grew bigger. He began to pant heavily and said to me, “Don’t worry my sweet. I don’t intend to cum in your mouth this time. We’ll save that treat until later.”
He held my head from behind and guided me through the every step of the way. Stopping me he then directed me to face the headboard of the bed and hold on to it. I knew what was coming and I tensed.
I felt his jellied finger enter me from behind and lubricate the walls of my anal cavity. Then he stepped off the bed and covered his penis with the same creamy jell. Getting back on the bed he mounted me, wrapping his arms about my breasts as he entered me from the rear. He did it slowly but when I stiffened momentarily he swatted my butt.
I yelped and as I did he entered me, pushing his member inside me to the hilt. Slowly and carefully he rode me, alternating between massaging my breasts and my own genitals. I whimpered enough when he touched my genitals that he said, “Oh, so you like that? I’ll keep it up then.”
Over the initial shock my training again kicked in I forced myself to relax and started to thump my rear against him. To my horror I quickly realised I was enjoying it, whether it was the submission, being taken or whatever my clitty was stiff stiff. I now sensed him getting close and hoped he didn’t finish before I did. Luckily for me, when he stiffened and his penis swelled to max proportions the pressure against my sphincter was enough that I popped like a cork. He spewed forth his semen at the same time and I ground myself into the mattress as he pumped for all he was worth into me.
When he rolled off of me I went to him crying, half out of shame the other out of pleasure. Sobbing and of course lying I told him I was no longer a virgin with a man. I let him relax for a little while and then started once again to fondle his penis, he responded immediately. I thought to myself “oh yummy this is going to be a long long night”.
