Forced Feminization - Sissy Office Slut Read online

  "Good girl," I teased, once I’d got my breath back and regained my composure.

  I dismounted and left him trussed up on the chair like a beetle on its back as I stepped across the office to my desk where I’d left his keys, phone and wallet.

  "Your oral skills will come in handy if your cock is going to be locked away for long periods of time. I'm so going to enjoy teasing you when you’re all horny, but unable to scratch your itch. I’m looking forward to the point where you beg me to let you out."

  I knew he always kept a condom inside his wallet – always the optimist. I took it out, knelt beside him, rolled it onto his hard cock and then stretched the panties back over his sheathed erection. He exhaled loudly as I touched him and then again as the silk panties stretched back over his cock.

  "Would you like one last orgasm before the girls get back and we lock your cock up? I know this morning has got you all hot and bothered, poor baby!" I said, softly stroking and patting the bulge in his panties.

  He smiled hopefully, but with a degree of mistrust.

  "Of course there will be a forfeit," I said, standing up and towering over him.

  His smile disappeared, his suspicions confirmed.

  "On the very rare occasions that your chastity cage comes off it will be under strict supervision and if you cum you will always be wearing a condom and you will always drink it all up.

  Every. Last. Drop.

  Today will be no exception. Do you understand?"

  He didn’t respond.

  I stepped forward and with one stiletto kicked his balls.

  "I asked you a question, slave. Do you understand what happens from now on to every drop of spunk you produce?"

  "Yes," he whispered.

  Another high-heeled kick to the balls.

  "Yes mistress," he added hastily.

  Nick had to watch helplessly on as I tilted the chair back upright and then got on my knees between his legs, lowered his panties again, my mouth an inch away from the tip of his cock. I blew on it. He flinched.

  He used to ask me all the time to tie him up and give him a blow job. I knew he loved it, especially when I was dressed in my office wear. Well, I wouldn’t be the only one dressed this way soon.

  "You always made me swallow. Now you're a girl, you will have to too."

  I licked the length of his shaft. It pinged rigidly back at me.

  "I’m going to buy a strap-on. A large strap-on. The biggest I can find..."

  I licked the side of his aching cock once again like it was a lollipop. Nick quivered.

  "I’m going to get a strap-on and you are going to learn to give blow jobs."

  Looking up into his eyes with my tongue just brushing and moistening the top of his cock, I said,

  "...and what's more, Nicola, Mistress Sarah is very much looking forward to tying you down over her desk and using the strap-on up your cute little arse..."

  My tongue now taking short little sucks of the very tip of his straining cock...

  "If I dress you like a sissy then I’m going to treat you like a sissy.... a little sissy bitch. I’ve often wondered what it’s like to fuck someone with a strap-on. I won’t lie to you - it excites me....a lot…. and I think, if I do it hard enough, it might even make me cum!"

  My mouth enveloped his cock and literally within a few seconds of sucking it I could sense his whole body convulse and jets of spunk gushed into the condom.

  Chapter 2. [ Holly speaking ]

  Hello. I'm Holly and I suspect you boys (and girls!) will be very interested in my story. A few months ago I took up a secretarial position in a small but very successful company run by a couple called Sarah and Nick. They also hired another girl at the same time, Jane.

  At the end of the first week in our new jobs Jane and I went out to celebrate with a glass or three of wine. We hit it off right away, making each other laugh all the time and in general we felt very much at ease in each other's company. I was so glad she had been hired at the same time as me.

  Emboldened by alcohol and well into the second bottle of wine we decided to play a bit of truth, kiss or dare.

  "Ok, the truth, please.." Jane asked me, "do you fancy the boss?"

  "Nick's a bit of a perv - he keeps leering at my bum and legs..." - then I paused for effect, "...but Sarah? She's really hot."

  After a moment's hesitation where I caught Jane's eye and I could sense she wasn't sure if I was joking, we both burst out laughing. However, it didn't take much more alcohol or many more flirty hints before we both admitted the truth that we both genuinely did fancy Sarah and that we both did indeed like girls.

  I took the very next opportunity in our game to dare Jane to kiss me.

  "I thought you were never going to ask!" was her beaming, twinkle-eyed reply and we snogged the face off each other.

  We ended up that night back at my place having rather drunken, but great sex and ever since then we've been a couple. We didn't tell Sarah and Nick. It was more fun to keep it a secret.

  In the office both Jane and I got a kick out of teasing Nick. We tried to out-do each other in the tightness of our sexy short skirts and skimpy office blouses. It was hugely entertaining and Nick fell for it every time. He, like most men, I suspect, clearly had a thing for sheer dark nylons and patent leather heels. It was just too easy!

  One day, quite on purpose, when Sarah was out and we knew Nick was listening we struck up an audibly-loud conversation about which hosiery we liked best, stockings or tights? Jane said she was a stockings girl and that the ones she was wearing were simply to die for, super sheer and fit beautifully. She especially liked the retro tops. I asked her to show me as I loved stockings too - they actually made me feel quite sexy when I wore them. We could hear Nick get out of his chair [ bingo! ] and tip toe across his carpet. We pretended not to see him staring through the crack in the door which was slightly ajar. I could feel his eyes tracing my movements as I ran my hand over Jane's thigh,

  "I told you! They’re so unbelievably sheer and silky, aren’t they?"

  "Oh God, yes, Jane, you're right, they're simply gorgeous! Your legs look and feel divine in them. I’m so jealous. I’ve got to get some."

  How we stopped ourselves from bursting out laughing I’ll never know, especially when Nick brushed past us quickly, hoping we wouldn't see the bulge in his trousers as he raced to the toilet at the far end of the corridor.

  Then Sarah started to notice Nick's wandering eyes, but she clearly thought we were entirely innocent parties in this and that there was no question of provocation or deliberate teasing. She was even very sympathetic when we felt we had to make an official complaint about his behaviour to cover our backs. We felt bad for Nick but we really didn’t want to lose our jobs and we thought it would just blow over. In reality we didn't mind one little bit that Nick loved our sexy outfits - teasing his prick and messing with his mind had become one of our favourite past-times – but perhaps what we were doing was unfair on Sarah. He was her fiancé after all.

  Our life in the office came to a head one day when Sarah and Nick had a blazing row in Sarah's office about his wandering eyes.

  Initially we felt bad, mostly for Sarah, and tried to keep as quiet as possible as we eavesdropped at the door. However, Jane and I couldn't help but giggle when Sarah started to tell him that she should make him wear a secretary's outfit around the office - and also a chastity device for his cock!

  For a few moments it went quiet in Sarah's office. Jane looked a bit anxious and whispered that she thought Nick must have hit Sarah or something, surely no man would put up with this kind of abuse?

  I suggested an alternative;

  "When I used to date guys I met a man called Richard who would have given anything to be in Nick's position right now. You know, I think there’s a chance he might just agree to do it. God I hope so - we could have sooo much fun!"

  We nearly wet ourselves with excitement when Sarah asked us in to her office, gave us the good news, and invited us
to share in Nick's humiliation. He'd agreed to do it! All of it! We were like schoolgirls clapping and squealing in delight.

  From then on the poor guy didn't stand a chance. Three attractive women, dressed in what were clearly his ultimate fantasy office outfits – Sarah was looking particularly fine today - discussing how they were going to lock him away in a chastity device, dress him up like us, only sluttier, and then tease him mercilessly. He clung on to the lever arch file by his groin but I knew he must have had a raging hard-on. The guy I mentioned to Jane would have given a kidney, a limb, even his soul to have been in Nick’s position. It seems some guys are just like that and as far as I was concerned this would be a win-win-win for all of us.

  Sarah was such a natural domme. My crush on her had never been stronger and I knew Jane felt the same way. We heard her order Nick to take off all his clothes and then she came through to the main office handing them to me in a bag with directions to their apartment around the corner. She certainly wasn’t messing about and I loved how she was taking charge of the situation. Assertive suited her.

  She asked us several times if we were OK with this and we assured her that we were having an absolutely fantastic start to our morning at work. We would love to help her bring her fiancé back into line and this would actually be a lot of fun.

  We left with company credit cards in our purses and a bag of Nick’s male clothes to dispose of.

  We put them in the bin. Something told us he wouldn’t be needing many male clothes in the future.

  Jane said ‘See you soon’ and left for the department store to buy Nicola's new outfits, and I headed for the sex shop. I knew my way around there and was no stranger to it.

  There was a wide choice of chastity devices, so I rang Sarah to see which one she wanted me to get. I half expected her to say that it was all off and that they had changed their minds, but, on the contrary, she told me to get a couple and she’d choose the one she liked. She also asked if they had any other interesting gear which might come in handy.

  "They've got a whole shop full of interesting gear. What did you have in mind?"

  She asked if she could be candid with me. I told her I was a big girl and that she should just tell me what she wanted - she was my boss after all and I was on an errand on company time - I would get her whatever she wanted.

  "I'd like a riding crop..." she paused, "...or maybe three?"

  "Look Sarah, how can I make this clear..? Jane and I would absolutely love to help you tease and train Nicola, if that's what you're asking."

  "Even though you know he fancies you both?"

  "By the looks of these chastity devices I’m pretty sure we will all be fine once you lock him up - and if you're concerned that Jane or I have feelings for your fiancé you needn't worry at all about that - we're lesbians."

  "Oh……really?" Sarah said with more than a hint of curiosity audible in her voice.

  "Yes, we're a couple - have been for a while. Now what else did you want? I promise you'll have to work very hard to shock me - a ball-gag? butt plugs? nipple clamps? Perhaps a vibrator for you whilst Nicola is under lock and key...? "

  We played a fun game of me on speaker phone describing the toys and equipment in the shop and Sarah telling me how much it made Nick squirm in his chair (apparently she'd tied him up). What Sarah didn't tell me, and I only found out much later, was that the heavy breathing I could hear wasn't his, it was her. She was sitting on the desk right in front of him, masturbating furiously as I described the fetish wear and toys. She told me much later that she had to bite down on her arm to stifle her cries as she came when I described to her my favourite vibrating strap-on harness and how utterly amazing it felt to wear.

  Sarah insisted I bought half the shop and that I should go to the department store to see how Jane was getting on. I was having a brilliant morning at work.

  Chapter 3. [ Sarah speaking ]

  Nick had the temerity to look accusingly at me as I masturbated my way through Holly's description of what a power-trip it was to have a 9'' strap-on jutting out obscenely from between your legs while the internal vibrators in the harness rippled through your bum and pussy. My fingers between my thighs speeded up when Holly described how it made the wearer tingle all over - she was pretty much addicted to hers - and Jane loved it too..... Nick's eyes were on stalks as I couldn't stop myself jerking and spasming to another glorious climax – that made it two of my best ever in one eventful morning!

  He looked anxious. I don't know what concerned him the most; - the imminent prospect of me taking him up the arse? - me having accepted, very eagerly, Holly's flirtatious, but genuine, offer for her and Jane to provide us with some very kinky staff training when Nicola needed to be 'inducted'? - or was it the dawning realisation (for both of us) that I was also lusting after the image of Holly wearing a strap-on and using it on Jane.......... or me!

  To be quite honest, all these scenarios made me wet and I couldn't tell which had made my heartbeat quicken the most and had hastened me to an unexpectedly quick climax.

  Nick was clearly concerned.

  "But.....Sarah.....I mean Mistress Sarah.....you're not... gay.... are you?...we're supposed to be getting married...oh, God......you've been planning this all along with Holly and Jane...haven't you?"

  "That's rich!" I snorted, and just for a moment the dying embers of our recent argument looked like they might be rekindled, but a quick glance at the hapless figure still bound to my chair by his wrists and ankles, still wearing my make-up and dressed in my sheer hold-ups, the bulge of his flaccid cock and balls in my baby pink silk panties… that all convinced me that there wouldn't be many arguments in the future. At least if there were, there would be only one winner. I would get to do whatever I pleased from now on and my 'man' would do exactly as he was told.

  I got off the desk and moved behind his chair so he couldn't see that I was smiling. I let him think I was angry with him as I reminded him of his predicament;

  "Seriously? I'm getting grief about my sexual preferences from my fiancé - who many would say is supposed to be my manly protector, but who prefers, it turns out, to ogle my secretaries and then wants to wear my lingerie and make-up and be treated like a dirty little sissy slut...... speaking of which.... do you still have the aftertaste of spunk in your mouth, darling? .... I must remember to upload that video file too - your expression was priceless!...Awww, poor baby!.....all us girls find it a bit salty and icky at first, but after you've had some practice, you'll come to acquire a taste for it....isn't that what you said to me once....?"

  I knew I was pushing him - seeing how far I could go. He didn't look like he was going to argue back but just to make sure I got some more parcel tape and put it over his mouth, making sure he didn't interrupt me whilst I explained a few home truths.

  No, I hadn't planned any of this, but now that he'd handed to me, on a plate, the means to ensure my husband-to-be would obey my every whim and desire, I wasn't about to pass up the opportunity. I also told him no, I didn't think I was a lesbian.....'bi-curious' is what I think they call it....and besides, he could hardly disagree that Holly and Jane were both very sexy indeed.....and no, he wasn't the only one who had admired their tight little sexy bums and pretty legs, but the difference was that I was far more discreet when I took a sneaky look at them. If I was going to dabble in girl-on-girl I would love it to be with them! If I was going to fuck other women, or men for that matter, it would be entirely my choice and he would not stop me.

  I could see, still hanging out from my panties, Nick's flaccid penis had started to twitch and stir back to life. He had closed his eyes and I could tell he was trying to fight it. This, not for the first time today, made me grin - it was like he had a built-in lie detector between his legs! I ordered him to keep his feet off the floor and pushed my wheeled desk-chair over to the full length mirror on the wall, and ordered him to look at himself.

  "Nicola, darling, you will never wear the trousers in this relationship ever
again, is that clear?" I said it in a tone that invited only the response it got,

  "Yes, Mistress Sarah."

  From behind the chair I started to run my hands gently and lazily over his chest, but stopping just short of his lap.

  "Would it really be so terrible for me to have sex with two other girls? " I said in a much softer, seductive voice, my hands now gliding over the outside and up the inside of Nicola's stocking-clad thighs, just avoiding his cock.

  "Holly and Jane have such lovely pert breasts, don't you think?" I teased, lightly flicking and rubbing his nipples.

  "Maybe you might come into my office one day and find me, skirt hitched up, blouse unbuttoned, Holly licking and playing with my nipples (I reached over licked his nipples) ...and Jane would be between my legs licking my pussy. Hmmm...would you like that Nicola? All locked away in your new chastity device - I'm sure that would be almost unbearable for you...watching us girls getting each other off?" His breathing was now heavy as his cock kept swelling and straightening.

  "...or perhaps we'd take pity on you and take the chastity device off...? Don't misunderstand me, it wouldn't be because we were being generous, we'd make sure you were fully restrained first of course. We'd be laughing at you as you'd buck and thrust at thin air in frustration......hmmm....I should definitely make that happen. It would serve you right for all the times you used to cum before me and then didn't think to find a way to finish me off....... I'm going to hang some shackles from the ceiling beam right here in front of the mirror, especially for you Nicola. From here you'll be able to see yourself bound and gagged, a damsel in distress, made up and dressed up in one of the sexy little secretary outfits you love so much, your ankles, knees and thighs bound together and your sheer stockings rubbing together as you squirm with excitement, your tormented cock rigid but always out of reach.... and in the background you'll be able to see me being fucked by two pretty girls. Even if you closed your eyes, you still wouldn't be able to shut out the sounds of our pants and moans."