by Alice Lloyd
"But she'll have to remember to sit down from now on!" Holly added laughing!
"..and you can probably tell that there's an opening for your arse – that should prove useful soon enough."
Next I felt a pair of panties, this time much more delicate in nature, being drawn up my legs and into place. Then came a deep belt of sorts which pulled in at my stomach. The straps hanging down confirmed my suspicion that this was some kind of corset with suspenders. Next at my chest I felt a bra being fastened around my back and, as I later found out, the detachable shoulder straps were put back on the bra and kept it snugly in place. The bra suddenly went heavy and made me change my balance as inserts were place in each bra cup. I was told to lift up one foot at a time as one of them held me from behind and one gently rolled up what could only be silky stockings up my legs, one at a time and attached them to the suspender belt. My cock was straining in it's cage and pouch as the mystery hands fiddled with the suspenders at the tops of my thighs. Then I was told to lift my feet up again, one at a time, before each was inserted into high-heeled shoes – very high-heeled shoes - which forced me to adjust my balance whilst ankle straps were fastened in place. Then, at my ankles, which they had forced wide apart, I could sense two different people attaching and securing a spreader bar with padlocks being locked around ankle cuffs. Finally I could hear the metallic clanking of what sounded like a long chain being attached to the wrist cuffs behind my back.
I struggled, just managing to keep my balance as the chain behind my back was tightened through some kind of pulley high above me, pulling my arms vertically upwards and forcing me to bend double, forwards from the waist.
Only then was the blindfold removed.
At first I did not see my own reflection, I could only gawp with wanton desire at the three gorgeous women pacing around me, who were inspecting their handiwork. First Holly – oh my God - encased from the neck downwards in the sexiest glossy black rubber catsuit, then Jane in a fantasy riding mistress outfit, smirking and brandishing a crop as she passed by, and then Sarah – oh Lord, Sarah, my beautiful fiancée - in a black leather corset and boots which made my chastity cage tighten alarmingly, squeezing the life out of my bound cock.
They circled me like they were stalking prey, taking their time, already certain of the kill.
Ominously, I could see that Sarah now appeared to be looking at the screen on her phone as she pointed the camera in my direction, as if to check the angles for filming.
Holly had disappeared for a few moments, but now came to stand directly in front of me. Protruding from her gorgeous, black rubber-encased thighs, she was now wearing a very realistic-looking flesh-coloured strap-on.
I turned my head instinctively sideways away from the bulb of the cock and saw for the first time a reflection of myself in this bizarre scene. In the mirrors which flanked the three walls of the reception area I could see my newly feminized self in a blonde wig, pink, frilly satin panties, bra and corset, a big pink ball-gag in place silencing any muffled protest I uttered, bent double, my wrists secured and drawn up tightly behind my back, the spreader bar keeping my tan nylon-sheathed legs wide apart, my arse pointing out, invitingly prone in open-crotch panties, whilst I struggled to keep my balance in my shiny pink stiletto-heeled shoes.....not to mention the fact that one of my secretaries, Holly, stood before me in a fantasy dominatrix catsuit taunting me by stroking a gloved hand menacingly up and down a realistic strap-on phallus inches from my face.
I was helpless.
Moving to my side Sarah, looking every inch a dominatrix in her leather outfit, removed my ball gag, "We thought we'd remind you of what kind of a girl you're going to be, before completing your transformation... and I also want a tutorial from Jane in how to use these....," She showed me, one by one, the riding crop, the bullwhip, a heavy wooden paddle, a flogger and a cat-o-nine tails. She placed them on the leather chair behind me and then applied some bright pink lipstick to my lips.
"Here's the deal..." Sarah said, as Jane swished a few practice strokes of the riding crop in the air,
"We figure that Nicola is the kind of girl who loves a hard cock in her mouth. She loves it. We want you to convince us that's true - we want a perfect performance. If at any stage we don't believe that you're enjoying it, I will get to use the crop, the paddle and the whip..... Did I mention Holly's cock, at 6'', is the smallest of the strap-ons she bought? We’ve got plenty of different cocks to try out on you. The advantage of this one is that it has a little reservoir in the balls, which, if you squeeze them, ejaculate. Unfortunately we didn't have any spunk to put in them, but milk will look pretty convincing for today.... and you will make her 'cum'. Do you understand?
I nodded, which provoked the first swish of the crop across my backside. I was shocked by how sharp the pain was - my God, I'm going to have to do this well - that really hurts!
"Your mistress asked if you understood?" Sarah barked.
"Yes Mistress," I replied.
"That's better, slut. I suggest you learn to obey my instructions first time, every time otherwise it will be a painful learning experience. Now, first I want you to beg Holly to let you suck her cock, ...make it good...imagine she has a real cock and you want nothing else in the world than to take it in your mouth and feel her cum shoot down your throat..."
She nodded to Jane.
I heard an electronic bleep as Jane selected video record on her phone (‘Yes, we’re taping it!’) and Holly took a step forward, the bulb of the realistic cock now an inch from my lips....
"Holly.....errr......" (Crack! Ow!)
"Please, Holly....please let me suck your lovely big hard cock......I errr...," (Crack! Ow!!)
"I'm a dirty little slut and I want to taste your spunk, please, please let me suck your cock..!!"
"Nicola, you really are a whore.... but, seeing as you asked so nicely," Holly replied, with a big wide grin, and thrust the cock into my mouth.
I had to endure a torrent of stinging blows on my backside as I sucked Holly’s cock, first from Sarah and then from Jane, who I thought would take it more easily on my aching buttocks, but she whipped me far harder than my fiancée and seemed to love making her ‘little pony’ go faster....
I got a brief respite as they all moved out of view and talked in hushed tones. When they returned their plotting became clear.
All three of them now were wearing identical squirting, flesh-coloured strap-on.
"You’ve made us all so horny, Nicola. Look what you did! We’ve all got hard-ons now!" they giggled, "And we all want to cum all over you..! "
"Holly – we promised you’d get to cum down her throat. Jane – I’d like you to record everything from the side and you can spunk over her face..... and as far me?..... I’m going to deflower my sissy boyfriend’s cute little arse and spunk inside his bum!"
They moved into position. Holly once more positioning the cock centimetres from my lips and grabbing hold of my hair in both hands, Jane to the side, pressing record and holding her phone in one hand, whilst masturbating the shaft of her strap-on lewdly with the other and Sarah now behind me, picking up a serious, heavy duty whip.
"Beg us to fuck you, Nicola," ordered Sarah as she cracked a warning strike on the polished floor next to me, "Tell us what you need, what you want us to do and what you will do for us now that you’re our sissy bitch!"
I knew that whatever I said, it wouldn’t be enough to avoid a beating, but it might just shorten it. Sarah had made it clear she wanted to try every whip and she’d been obviously saving this one until last.
The blow that struck my backside hurt like merry hell, the second was much worse and after the third I thought I might pass out.
I started jabbering away about wanting them all to treat me like a slut, a whore, their bitch. I wanted their cum inside me and all over me. I wanted them to spit roast me, it’s what I’m for... I’d be their slave... I’d do whatever they wanted....No matter how depraved or humiliating.... PLEASE.... FUCK
.... ME....!
And they did. Holly rammed hers into my mouth and held me in place with her hands gripping my hair, Jane warned me she was so horny she wouldn’t be able to stop herself cumming on my face very soon, and Sarah, having lubricated her cock and my arse, inserted her dildo up to the hilt in my bum and started to buck and thrust holding on to the chain from the ceiling that restrained my wrists.
They all clapped and cheered when Jane, in a fine acting performance, started orgasming loudly and spattered her cum all over my face, then I felt Sarah thrusting hard and vigorously before liquid spurted up and out from my arse and then Holly, cock fully inserted to the point at which I gagged, squirted down the back of my throat.
Sarah, worryingly, her face flushed with excitement, seemed absolutely delighted with her first experience of fucking my arse and immediately instructed Jane to send it to her email for her entertainment and my further humiliation.
They untied my aching arms from the chain hanging from the ceiling but left me lying in a pool of their ‘spunk’ to reflect on what had just happened whilst they went to plan the rest of the day.
I felt used, I felt ashamed and I felt embarrassed....
………..and yet the only thing between me and a constant, raging hard-on was the snug bit of plastic containing my frustrated cock.
Chapter 6. [ Jane speaking ]
It was approaching lunchtime when we left Nick lying, still restrained, still wearing his, blonde wig, pink sissy outfit and fuck-me shoes, still in his vagina panties and fake boobs, covered in our fake cum.
In the space of one morning his working-life had changed beyond all recognition, and even if he was having second thoughts, Sarah wasn’t and it was way too late for him to try to change her mind.
We went through from our reception area to Sarah’s office and she discussed with us how the rest of this day and the rest of our lives working at this company would run.
She was the boss now. We were next in seniority and as for Nicola..? She would be everyone’s bitch.
Sarah gave us direct instructions not to let up with the humiliation. He’d asked for it and we would be happy to provide it.
Acting in my new capacity as person in charge of Nicola’s make up and wardrobe, I decided to send her off to the shower while I picked a slightly more demure outfit. She would be going to pick up our lunch order from the deli shop around the corner (formerly one of my jobs) and I wanted to see if we could get Nick to pass as a convincing girl. The temptation to put him in skyscraper heels and a skirt up his backside would have to wait until he’d practised the art of being a woman.
To be honest, most of the outfits we’d chosen were very slutty indeed. The least-worst option from his point of view would be the girly-girl look – a navy blue pinafore dress with a long-sleeved crisp, white blouse underneath, coupled with Mary Jane shoes and some nearly-black stockings. The first wig he’d worn – a long blonde number – was now covered in our ‘spunk’ and would need washing, so the back-up wig – a cute, straight, shoulder-length golden blonde one would be used.
The others agreed that this version of Nicola could, if you didn’t look too closely, convince many that she was a girl. The boobs and vagina pants gave her an impressive, voluptuous figure and Nicola had great legs, especially in heels.
We gave her a coat, a pat on her (still sore!) arse and said she should hurry back with our lunch – we’d built an appetite and she should not keep us waiting.
Sarah had written-off this day as ‘team-building’ and went to retrieve some bottles of wine left over from the Christmas Party from the stock cupboard. It had only just gone noon, but she poured us each a glass and we toasted our new office arrangements.
"Do you think Nicola might make a bid for freedom and run away?" I asked.
"Not if he knows what’s good for him," replied Sarah, turning the screen of her computer round to show us the video I’d taken.
Holly had other reasons to be sure he’d be back.
"Richard Thornberry," she said.
"I’m sorry, who?"
"He was the boyfriend I mentioned earlier to you, Jane, when Sarah was telling Nick off in her office – you know, the one I said I’d dated ages ago, before I discovered ‘bi-curious’ for me was actually just ‘bi’ and also before I met you and that convinced me that ‘bi’ probably means ‘lesbian’ in my case... "
"I have that effect on girls, you know Sarah – once they’ve fallen for my charms I can turn straight girls gay! You’d better watch yourself !" I added with a wink.
Sarah looked as if she might be blushing a bit.
"So what about him?" I asked.
"Well, he had plenty in common with Nick and he’d love it if he were the one being forced to dress up as a girl and being sent out in public to be humiliated – that was just his type of thing."
We asked Holly for details.
"Well things weren’t exactly going well in the bedroom for us when we were dating and after yet another rather uninspiring and aborted attempt at standard missionary-position sex, we’d discussed how that really didn’t do it for either of us.
After my second glass of wine I opened up to him about wanting other types of sex and even mentioned being bi-curious. I also told him I preferred being assertive during sex. I liked to be the boss and, to be honest, quite liked the idea of bondage and domination.
I asked him if there was anything he’d always wanted to try but hadn’t had the courage to ask a girl to do it for him. He took a big glug of his wine and then confessed, red-faced, that he was secretly turned on by pretty much the same thing. He liked assertive women – he was excited by what I had said. He fantasized about mistress-slave scenarios too. A lot.
Well that sounded very promising, I thought and I pressed him for specifics – this was his big chance to get a girl to do this type of thing with him.
After a lot of encouragement from me he said his particular thing was to be sexually teased and humiliated – and, he added, not just a little bit of tying up and name calling, he meant really humiliated.
Well, to have said I was intrigued would have been an understatement! I forced him to tell me exactly what he had in mind – with a huge grin on my face I said I could always spank him until he confessed.
We didn’t need a whip, though in the end. After a lot more encouragement and pressing from me, and also a fair bit more alcohol, he said his ultimate turn on would be if the girl was really into it – if she got some twisted pleasure or some kind of benefit out of it – he didn’t want to feel like he was asking to be humiliated, he wanted her to want to do it......perhaps the girl might get a kick out of it? ......perhaps it made her laugh to get the guy to do embarrassing things ..... or, and he hesitated at this point, ..... the girl want to blackmail him...it might entertain her to get him to do things for her or buy her things.
He described it as a ‘feedback loop’ – the more the girl enjoyed doing it to him, the more humiliating it would feel and the more turned on he would get and so on."
"Well I sincerely hope you didn’t disappoint the poor little lamb?" I said.
"Jane, honey, you of all people should know I always aim to please in the bedroom, especially when someone confesses their dirtiest fantasies to me! So, of course I made him do it – it was going to be like a little experiment and a big, sexy adventure for me – how could I say no?"
Holly was right. I did know from personal experience how obsessed she was with finding out what turned her lover on and then she would want them to live out their fantasies with her. That was definitely her thing in life.
She would for example, tie me to the bed and use a vibrator on me for what felt like hours, edging me and holding me at the point of cumming, and she would make me look in her eyes, enjoying every second of my heightened sexual arousal...forbidding me to cum until she wanted me to.... then finally make me say her name over and over again, before finally allowing me to orgasm. The satisfaction on her face was always sincere, as
if it were a job well done (‘Look what I’m making you do! Look how I am making you feel!’) but I also thought there was also a slightly sadistic side to that pleasure (‘Look what you were prepared to do for me! Look at what I made you do!’)
So, depending on how you looked at it, Richard had either picked the wrong girl to confess to, or alternatively, his choice had been perfect.
Holly continued her story,
"We started off gently. I got him, whilst he was still a bit tipsy and before he could change his mind, to tell me how a girl might blackmail a guy. You know, hypothetically-speaking, I said, with a sweet smile. We both knew full-well that I’d be making him do it before long.
He told me about consensual blackmail mistresses on the internet and I made him show me them. They took all a person’s contacts, phone numbers, email addresses and then made sure they had something incriminating that they would never want anyone else to see;
Enforced crossdressing was obviously a favourite, but there were also other ways to humiliate a guy – freeze his cock and balls with ice and make it look like he had a pin dick and take pictures, make him play with a dildo, public humiliation, even forced-bi.
I told him if we did this I would not limit what I made him do to things he actually liked. I would have to make him go at least a little beyond what he was comfortable with if it were to be genuinely humiliating. He swallowed hard and then nodded, saying he was pleased I had understood, but I could also tell that he was a little bit scared now. I was taking to this like a duck to water and things were moving fast.
As we looked further at these sites I remember it was the first time I’d ever seen a male chastity device. It fascinated me and I made him order one right away. To be honest he was that excited he didn’t actually need that much persuasion.
To seal the deal I wanted just one email contact (his female boss) and one phone number (his ex-girlfriend), which, again, in his excitement he did right away.