Punished

by Tina Majors

  It helped that I was an absolute, bona fide expert on the era having studied it for a single semester on my Liberal Arts degree. I would put in some John Hughes, a little bit of course of the Brat Pack pantheon of classics, the original Buffy The Vampire Slayer movie – this would then segue into Teen Wolf, the less heralded but still cult classic Teen Wolf 2, some Clueless, maybe The Craft, and then some Paul Veerhoven action, Starship Troopers and Showgirls.

  It felt like a very well put together selection that covered all the bases.

  I knew my movies, no one could deny it.

  I only hope that my tastes were appreciated.

  I looked around and realised that I had missed a patch with my hoovering. I placed the tv remote on the large comfy corner sofa – that, ironically, had two corners, it was kind of a U shape, easily large enough to fit eight people on comfortably.

  Perfect for a movie night.

  I plugged the hoover back in, a top of the range model that actually made hoovering a pleasant task, believe it or not, and quickly manoeuvred it over the affected area. Like I expected, it easily lifted the remaining dirt.

  I switched the hoover off and surveyed the room.

  I had done a good job, of that I was confident.

  I heard the phone ringing in the kitchen but to be quite honest couldn’t be bothered to walk in and answer it.

  After all, it would probably no doubt be some kind of telemarketing service, trying to get me to sign up to some kind of new insurance plan or making some kind of accident claim or some such scheme.

  Now even if I was the man of the house, which of course I certainly wasn’t!, there was no way I would get involved with something like that.

  I was actually just a bit tired from all my hard work.

  I let the phone ring out and took a seat on the large sofa and switched the TV on and casually flipped around the channels, just taking a breather and getting some relaxation in.

  The thing is, even though tonight was meant to be a fun sleepover, I just had a kind of feeling – and no without good reason – that it may not be all that relaxing for me.

  **

  Madame Jennifer shouted up for me. She was downstairs and had just come off the phone with Madame Annabelle. I had tried to make out what was being said but also was careful to not be caught doing so as eves dropping would not go down well with either of them.

  It was very important that I knew my role as a beta male – important conversations did not concern a bimbo like me, I was here to do and serve as I was told.

  Truthfully, this thought not only relaxed me, it also excited me.

  I had to be careful not to get too excited however as I finished changing into my outfit for the evening ahead.

  As it was a sleepover, Jennifer had decided that I would be wearing a highly feminine, sensual cropped pyjama set. In other words, tight pink satin trousers that were tight around my sissy ass, and a very small matching pink satin button up top that was short around my midriff, revealing my smooth, shaved chest.

  Oh, and of course, underneath the pyjama bottoms I had been given a pair of absolutely tiny panties that were designed to keep any unwanted stiffness under control.

  When I say tiny panties, I mean they were ridiculously small.

  Apart from the front piece of material, that was so small it struggled to keep even my tiny dick inside, there were two strings that connected to a virtually non-existent back.

  If you didn’t know I was wearing anything underneath the bottoms, I don’t think it would be possible to tell.

  “I won’t tell you again, sissy, get down here!” Jennifer called out, her voice authoritative and a little bit impatient.

  I finished checking myself out in the mirror and left my room to take the stairs down to the ground floor.

  I couldn’t deny it, I was feeling a whole range of emotions. Part of me was incredibly turned on by the prospect of my first sissy sleepover, the thought of several women, all in the mould of Jennifer, having fun at my expense, ridiculing me, punishing me if I took a step wrong, and who knows what else, was a major cause for excitement.

  But on the other hand I was also petrified by the idea.

  What if I wasn’t able to please them?

  What if their plans for me pushed me too far, tried to make me do something I just wasn’t ready for?

  There was also the unknown factor. As I hadn’t experienced an overnight situation, I had no real idea what to expect, what the possibilities truly were.

  I would soon find out.

  Just as I was letting my mind run away from me, I remembered Jennifer’s impatient tone of voice and got down the stairs in double quick time.

  “Well I thought you had got lost,” Jennifer said. “I hope this isn’t going to be the precedent for the evening?”

  “No, Madame,” I said, “I will be ready and waiting to serve as promptly as is required.”

  “Oh, sissy, you sound very nervous!” Jennifer laughed. “Perhaps you need a bit of a warm up, just to shake out the nerves?”

  What did she mean? I half suspected that Jennifer would put me over her lap right there and spank me not only for my slowness, but also for my nerves.

  “Anything you wish, Madame,” I replied, hoping that my quick response and respectful, subservient tone would find favour with her.

  “Good. Well, I’m not going to punish you,” She declared. “You need to relax, you need to be in full on slutty sissy mode ready for when the ladies arrive. Okay, here’s what we’re going to do. You are going to answer the door to the caterers, they should be here any minute, and you are going to take them through to the lounge room where they will leave the food.”

  “But, I’m wearing pyjamas… women’s pyjamas!” I said, immediately realising that this was the whole point.

  “Exactly! That’s exactly the idea you stupid little slut,” Jennifer declared.

  Well, the caterers did arrive, and I answered the door to them wearing my tight, feminine, pink satin pyjamas. I could sense the women caterers giggling, staring, rolling their eyes at how pathetic I was. Now the male members of the catering team, I certainly felt their eyes burning a hole in me, especially as I walked in front of them, my sissy ass wiggling in the bottoms.

  As I brushed past one of them, a very muscular man in his early thirties, I felt his crotch bump into lower back. For a split second I felt him grind into me a little.

  This made my entire body quiver and I quickly excited and showed the catering team out of the house.

  “Well, I saw that, don’t think I didn’t,” Jennifer said. “So tell me, did you lie it when the big strong man rubbed his bulge against your sissy boi body?”

  “Yes, I said, “It made my sissy clitty tingle.”

  It was so humiliating and degrading to talk like this, but I knew which words I could use for my erection and if I didn’t stick to them I would get punished – and it was way too early to face a punishment.

  “Well tell me then, do you feel ready to be the perfect sissy?” Jennifer continued, “Because if a big hard cock makes you tingle then there is no way you are a real man, you must be a true cock hungry sissy?”

  “Y-y-y-yes,” I said, my voice wavering, “I am a… cock hungry sissy. Thank you, this has helped me very much.”

  “Excellent, now give me a twirl, then drop to all fours and shake that sissy booty for me!” Jennifer laughed, knowing full well that she had me in the palm of her hand.

  I dropped down and popped my booty, much to her amusement. I felt my cock harden further, I kind of wanted the big strong caterer to witness this. I couldn’t help but say it out loud.

  “Yes, reveal yourself to me, slut,” Jennifer laughed. “Who knows, maybe you will get a chance later? But for now, I hear the doorbell. Looks like the ladies are here!”

  **

  I walked to the door, the sound of loud and excited women was quite apparent – and I felt nervous. The feeling hit me like a sledgehammer and I turned nervously. I
was met with a stern, no-bullshit look from Jennifer.

  She would not tolerate being embarrassed by an underperforming sissy this evening, and had spelled that out to me when she brought up an image on her phone of a quite monstrous black dildo; Make no mistake, she had said, if you don’t do your job this evening, this thing will be going right up into your sissy fag ass… whether you’ve got lube on or not. This was enough of a warning for me.

  I took a deep breath.

  I opened the door and as I had been instructed, made my formal introduction to the women:

  “Good evening, ladies,” I said. “You have been invited to Madame Jennifer’s Weekend Sleepover and I will be your sissy slave for the night. Please feel free to address me as you please, instruct me to your exact specification, use me any which way that meets your requirements.”

  With that, I got on my knees and waved the ladies in.

  Each one walked past me, a couple patting me on the head.

  I had been told to keep my head down, show respect for the superior women and not get in their bad books. But of course I couldn’t help take a sneaky look.

  They were all, to put it mildly, absolutely magnificent looking.

  Dressed in smart casual wear of tight leggings and tight fitted t-shirts (all the top level fashion brands of course), they had figures to die for.

  It was like having ten Madame Jennifer’s in the room!

  Each one was different though. Some had the perfect sporty bubble butt that you just know does at least a thousand squats a day and a load of HIT training to go with it.

  Others had larger booties, one lady in particular had a striking resemblance to Serena Williams. I watched as her large butt cheeks jiggled and clapped underneath her shiny, white lycra leggings.

  I knew I had to check myself, and fast, otherwise I would get rumbled for drooling after them.

  I couldn’t deal with the prospect of getting punished, no doubt in a most humiliating way, this early in the proceedings.

  “Sissy!” Annabelle shouted, “Where are our drinks you stupid little slut?”

  Damn, the champagne! I was meant to have it ready. I crawled on all fours as fast as I could to the kitchen, much to the laughter of the women.

  Was this setting the tone for the night?

  I had a sinking sensation it might be.

  The night continued in a similar vein. I was routinely bossed around, made to complete menial tasks, and insulted. How about this a list of insults off the top of my head:

  Bimbo

  Bitch boi

  Beta loser

  Tiny dick

  Wimp

  Pathetic sissy bitch

  Yeah, and there were more, as I am sure you could imagine.

  Jennifer and the women had grown bored of taunting me however and had decided I would have to put on a show for them.

  “Sissy, you have exactly two minutes to get out of those pyjamas and return in the sluttiest get-up you can manage,” Jennifer declared. “When you return we will be expecting you to do a little dance for us, and it better be the most degrading, cheap, tacky, slutty dance you – or we – can imagine. Anything less and we’ll have you sucking off the security guard who patrols the neighbourhood!”

  This caused all manner of a ruckus and merriment in the room. The ladies, who had downed a fair share of champagne, had gotten quite rowdy, and any sense of decorum had long gone.

  Sophia, the Serena Williams lookalike, offered to help me get ready.

  “Just to make sure you get it full on slut level, I’m going to come with you, bitch,” She declared, to the cheers of the others.

  “Wait, why don’t we all take him? Come on, grab him!” Cried out Susan, a woman in her late thirties who was five ten, five eleven, a top level TV executive, and had a body that you could see the full effects of her three hundred dollar an hour personal trainer.

  “So be it!” Laughed Jennifer.

  Before I had a chance to move, I was grabbed all over by the women and suddenly found myself horizontal, staring up at the gan of women as they grabbed and pulled at me as they took me up the flight of stairs to the special Sissy Closet that had been converted from one of the many spare guestrooms.

  As I was dragged into the room and thrown on the fluffy rug, the women walked over me and began to pick out what I should wear.

  Every kind of panty, thong, camisole, bra, suspender, pantyhose was flung at me amongst the hubbub of the women excited by the opportunity to feminize me to the absolute maximum.

  “Now ladies, remember we want him as slutty as possible!” Jennifer stated, calm but also enjoying the high spirits that the moment of spontaneity had created.

  “What about this pair?” Sophia said, holding up a pair of pink panties that had tie-up sides and a frilly waistband that cut straight into a tiny thong back.

  Everyone looked at me, squirming, stripped naked on the floor with my cock sticking up, pumping, hard, ready to explode.

  “Well clearly sissy cumslut approves!” Jennifer said. “Go on, sissy, get into them and show us how depraved and cock hungry you are!”

  I did as I was told, pulling the panties up over my legs and onto my cock. The feel of the smooth, fresh panties on my throbbing dick nearly pushed me over the edge.

  I realised I didn’t have long before I made a sissy mess everywhere but knew full well that I would be expected to put on a show. I began to gyrate and rub my hands over my body, pulling on my nipples, stretching them up to my mouth.

  The women were all clapping and cheering.

  I turned and bent over, rubbing my fingers around the string which only barely covered my puckered, excited hole.

  Then I felt myself being flung down over the soft velvet sofa. Sophia grabbed my hips and raised my ass, ripped the thong off and spread my cheeks, spitting violently on my ass.

  “Get it in him!” Came the cry from the women, in unison.

  Then I felt it, a long, hard, dildo being eased into my tiny sissy beta boi ass. I let out a groan, then a moan, then another moan.

  I couldn’t deny it any longer, I was enjoying this.

  “Yes! Yes! Beg for it sissy! Imagine it is a real big black cock!” Sophia demanded, much to the approval of the women, and most notably Jennifer.

  “Please, oooh, please give me that big hard black cock!” I pleaded, not even pretending just to please her. “Fill me with hard, real alpha dick, give me a sissygasm! Oooooooooh, yessssssssss!”

  To loud cheers from the room, I found myself bucking away on the dildo, pushing back, working my little feminized ass on a big black cock, cumming hot sissy cum all over the sofa.

  Finally, when I was spent, I was given a round of applause and told I had ten minutes to compose myself before service would resume for the evening.

  “We’re going down to put one of the movies you chose for us on. How about Showgirls? I think he could practice his slutty moves while we watch it with him?”

  The women agreed and left me to recover as they walked down the stairs and into the cinema room. I was exhausted and completely spent. I couldn’t believe what had happened.

  I also knew that I could never go back from this moment, this was an epic step forwards in my journey as a sissy slut.

  **

  The rest of the evening went as I expected: several spankings, constant humiliations, lots of deeply sissified behaviour as we watched Showgirls – including one especially humiliating moment, recorded on several of the ladies’ phones, that involved me gagging on a banana while each of the women took it in turns to simulate taking me from behind.

  I could feel the wetness of their pussies on me as they did this and it wasn’t long before I was on my back, my face and tongue acting as a pleasure spot for them as one by one they took their turn at riding me until the climaxed.

  Each one seemed to take a specific delight in grinding and riding my face.

  Some pushed down hard, others seemed to hover and tease.

  Both styles were
equally punishing and thrilling.

  Of course, I was forced into cumming again.

  I say forced, it was never that far away from happening naturally.

  As the women retired to their guestrooms for the evening, Jennifer told me to wait back with her.

  “So, sissy,” She said, “You did well tonight, very well. Now, I’ve had a word with Sophia and she might be popping in to see you at some point, so be prepared to serve her well. How does that sound?”

  “It sounds… perfect,” I said, trembling but excited by the possibilities.

  “Excellent,” Jennifer said, patting me on my bottom, “Now, time for you to get to work on my ass and my pussy with that tired little tongue of yours…”

  “Yes, Madame,” I said, as I lay down dutifully on the sofa and got ready for my Goddess.

  There was still life in this sleepover yet…

  **

  The next day, I pulled my car into the supermarket carpark and found a convenient spot not too far from the entrance. Okay, unpopular opinion time but I always kinda resented all the parent and child reserved spots.

  I mean, a kid can walk!

  Okay, so maybe a couple of spots for a parent with a baby is reasonable, but a mom (or dad!) and their twelve year old kid don’t have to be close to the store as a matter of necessity, do they?

  Absolutely ridiculous if you ask me.

  Well, it grinds my gears that’s for sure, but ultimately I suppose it’s not worth getting wound up about in the longer scheme of things.

  So as I say, I parked my car in a decent spot and shut the engine off.

  It was a luxurious car, a 2017 model Mercedes coupe. Really comfortable but with a lot of kick in it too. It certainly drew a lot of glances, probably in no part down to the shocking neon pink colour.

  Yes, it was a bit humiliating being seen stepping out of it, I guess some people could in theory have thought I was driving my wife or girlfriend’s car, but it was also a definite clue.