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The New Sissy Secretary

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Hi, I’m Julie and I’ve been cross dressing as a woman since I was very young. Here’s my latest adventure as a sissy maid.
The phone rang, ‘Julie, it’s Peter, we’re having a board meeting tonight and I want you to come and serve drinks to the Directors. Under your maids dress you will wear your usual silk stockings suspenders and knickers and high heel patent shoes. You will make sure you are well lubricated. I know you are wearing your chastity device as I still have the key. You will be here by 7pm. Do not let me down. Do not be late!’
The phone went dead and my cockette – as I had been taught to call my cock – twitched with anticipation and my heart started to beat a bit faster. I had met Peter through our mutual friend Pauline, a few months ago. Pauline had known me since we were at school and realised that I was happier being a girl than a boy. Over the years, she had taught me how to walk, dress, speak and think like a girl. She was working for a finance company in the City and had found out her boss was fascinated by sissys and transvestites when he left his computer open on a TV contact site by accident.
Always looking for an opportunity, Pauline had introduced us both at a party and I became Peter’s fuck slut and Pauline got a promotion! Now it was time to concentrate on getting ready. I ran the shower, stripped and got in. I checked to make sure I was totally hairless and smooth all over. I dried myself and rubbed body lotion onto my skin to make it silky smooth.
Getting dressed in my maids uniform always makes my little cockette stiffen with anticipation, but the chastity device makes sure that any sexual excitement is immediately punished as my cock is crushed cruelly in its plastic cage.
As demanded by Peter, its suspenders,lack seamed stockings, silky knickers, and the rest of my uniform.
The skirt is so short ensuring my sex and bottom are easily accessible by anyone who cares to grope me.
I arrive and Peter immediately checks my preparations. He looks me over and runs his hands up and down my legs checking my stocking seams are straight. His hands caress my chest and give my nipples a playful twist. I moves in and smells the perfume on my neck as he softly kisses my cheek. ‘Very good Julie. Now bend over and spread your legs’, he demands as his fingers are pushed into my sissy cunt. Satisfied that I’m well lubed, he slaps me on my bottom. ‘Good girl, now off you go and serve the men drinks.
There are only 5 men there, but I recognise one I’ve met before – Geoff – he has a huge cock and a wicked streak. I’m not going to get out of here without a well stretched pussy. I move among them and instantly feel hands groping my body. My bottom is patted, stroked, spanked and invaded by curious fingers. My tits are pulled and tweaked. My nipples are teased and crushed between warm fingers. I can only stand there holding the tray of drinks and accepting the humiliations of being a sex toy for their amusement and try to stop my cockette from getting stiffer as I suffer the ecstasy of being abused.
After their initial groping, they take their drinks and I am allowed to put the tray down. ‘OK, Julie, on your knees’ To encourage me, I hear the the familiar swish of Peter’s crop behind me and feel the sudden lick of pain on the back of my legs. I drop to my knees and open my mouth as I have been taught to do in the past.
I hear the familiar sound of zip being undone and I’m presented with the first cock of the evening. I love sucking real mens’ cocks, being on my knees as I offer my mouth to them makes me feel so submissive. I knew the first time I sucked one in the school showers that I was destined to be a cum slut
I take the first cock into my mouth, running my tongue over the head and feeling the heat as it starts to stiffen. He holds my head firmly and starts to face fuck my mouth. His cock is hitting the back of my throat and I start to gag a little, my eyes begin to water and I know my mascara is running. Another man has his cock out and is slapping my face with it. I can feel it getting stiffer with every hit.
Another pair of hands are feeling my silky knickers as they cup each cheek. The fingers reach into my knickers and start to pull them down exposing my sissy cunt to everyone. The same fingers start to push into me, first one, then two and then the third one. They push harder and my cunt is being stretched wide. I don’t mind as it will prepare it for the fuckings that I know will start soon.
Suddenly the cock in my mouth is being forced deep into my throat and being held there. ‘Im coming you bitch, get ready. Do not spill a drop’. His cock throbs and the unmistakeable taste of a man’s cum fills my throat. He shoots again and again unloading all his spunk into my mouth.Its a lot for such a relatively small cock but I manage to swallow it all – I don’t want to receive the crop for spilling any. He goes limp in my mouth as I take the final drops and start to clean his cock. I’m thanked with a light slap on the face and a ‘Good girl’.
This prelude spurs the other guys on. I am lifted bodily and laid over one of the deep leather armchairs. My knickers are ripped off and with no ceremony at all the first cock of the evening is pushed hard into my stretched cunt. It takes my breath away with the speed and depth of the first thrust, but I recover quickly as he starts to fuck me with a nice steady rhythm. I’m in heaven as this cock slides in and out of me and causing me to drip pre-cum from my locked penis
My mouth is filled with another cock and my hands are guided to wank the other men. By the size of one of the cocks I know its Geoff. They always leave him until last as his huge cock ruins any girls cunt for any guys following him. The cock in my other hand is getting very stiff as I massage it up and down, slowly and then speeding up, I hear him gasping. He’s new to all of this and the sight of me being fucked and sucking a cock at the same time while Im wanking him is all too much for him. With a gasp I feel him shoot his seed all over my face and now I’m covered in spunk as the cock in my arse starts to speed up. He’s one of those fast finishers and he starts to pound my poor cunt at a tremendous rate. I’m getting a punishment fuck and I can hear the slap, slap, slap sound as our bodies meet. Mercifully he can’t keep this pace up and I feel the unmistakeable throb and squirt as he unloads into my cunt. Simultaneously the cock in my mouth is whipped out and he spunks his seed all over my face to join the previous guys load. ‘What a fucking mess you are Julie’ I hear Peter say ‘ Get off the furniture and clean your self up’ he comes behind me and plugs me with a but plug .’This will keep all that goodness inside you, you slut’ I get on the floor and wipe my face with my knickers.
‘Hello slut’ I hear Geoff say behind me as he wraps a cord around my useless balls ‘Just a precaution as I know how much pre-cum you drip when I fuck you’ He laughs and slaps my bare bottom quite hard. I squeal from the mild pain. ‘Shut up, bitch’ he says as he stuffs the cum covered knickers in my mouth ‘You’ve had it easy so far tonight, now I am going to give you the fucking of your life’
The others gather round to watch as Geoff gives his huge cock a final pull. It must be eight inches long but its very, very wide. I feel him behind me and he unceremoniously pulls out the but plug. It makes a popping sound and I immediately feel warm spunk seeping out and down my thighs. He quickly puts his cock head onto my hole and stops the flow. He pushes quite gently to tease me and increase my apprehension. I know that if I tighten my hole it will hurt a lot more more but its hard to relax when I know what that fearsome cock will do to me. Can she really take that’ I hear one of the guys says.
‘She doesn’t have a choice’ says Geoff, as he gives a mighty thrust of his hips and I’m impaled on that huge weapon. The two loads of spunk I’ve already taken help to lubricate my cunt, but I still scream with pain and pleasure as I am filled with his manhood. His hands grip the sides of my waist and my head drops to the floor. The humiliation as I realise I’m in a room full of strangers, my arse in the air, face in the carpet and a real mans’ huge cock buried deep inside me, knowing that this is want and need.
The fucking starts quite slowly not too deep pulling his cock almost out of me stretching my ring and pushing back in. Then he fucks me hard, fast and deep , then he pauses and gives my poor cunt time to recover before he repeats the process. He fucks me for fifteen or twenty minutes. I have lost all track of time and I’m just a fuck sleeve for his cock.
My pussy is sore and as wide open as its ever been. ‘Grip it bitch…feel that cock’. I squeeze him as much as I can as I know he’s going to cum very soon. His grip on my sides tightens. It’s is like a vice, there’s no escape and I know shall be bruised in the morning. His fucking slows as he starts to shoot inside me. He pushes deep and then shoots, he goes deeper and shoots again and then deeper still for his final spunking. I want to collapse, but those hands hold me in position.
After a short while I sense the unmistakable feeling of being filled as he starts to piss inside me. It’s warm and strangely comforting. His hands loosen their grip on my waist as his cock starts to subside inside me. ‘Don’t move Julie, we don’t want a mess on the carpet’ . In one quick movement his cock is replaced with a big but plug to keep all the fluid inside me.
With a final slap on my arse he’s finished with me. I slump onto the floor. I’m used, disorientated, aching, full of Geoff’s piss and seed and covered in sweat and cum with my clothes in disarray.
Becki and the Dress Shop 11/02/2022 In "feminised"
He made me a sissy! 15/10/2021 In "Anal"

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I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked like she was giving it an extra special sway, knowing she would watched.
"Good morning sissy boy," was all she said before entering her office. Immediately the cock between my legs began to rise, being called that aloud in the outer office turned me on. Looking around, hoping no one had heard her call me that.
"Good morning Boss," I replied as she was shutting her door. Trying to concentrate on my work for the next few minutes, as hard as that was, I was wondering what was in store for me today. The panties felt good rubbing against my now raging hard-on. Seeing her hot ass sway through the door had me quite excited.
"Sissy boy, come in here now!" the intercom sang.
Nervously I grabbed my notebook, pen, and the finished Scottsdale account paperwork, then went into her office.
"Yes Bo..." as I tried to say, but was cut off before the words left my mouth.
"Show me now," was all she said when she interrupted me. I stood there dumb founded for a minute, not sure, what she meant. "Show me the panties sissy boy and be quick about it! I will not ask twice!" she said in a commanding tone.
As quickly as I could I removed all my clothes, except the panties, but it was not quick enough.
"Well aren't we slow this morning! From now on, you had better be dressed properly when you are in this office! On your hands and knees and get the riding crop. Do it right now!"
The look in her eyes told me that she was enjoying my discomfort. As I crawled over to the filing cabinet, stealing looks at her crossed legs as I went, I could feel her eyes on me. Her legs looked great, with one crossed over the other, bouncing slightly. This made the skirt ride higher up on her thighs, showing off her sexy thighs. The top few buttons of her blouse were also undone, leaving the top of her healthy breasts on display. Her hard nipples pressed against the thin fabric, reminding me that she enjoyed this too. After I got the riding crop, I crawled back over to give it to her. The scent of her driving me wild, the closer I was to her.
"Stand up and bend over the desk! You must be taught a lesson!" My ass was totally exposed to her in this position.
Swish. smack! Without warning the first blow struck. "OUCH!" I responded without a chance to think.
Swish...smack...swish...smack. The next two strikes hit. "Did you forget how to respond?" Swish. smack.
"OUCH, I'm sorry, 3 maim, thank-you maim!" but this was too late.
"I don't believe we start counting at 3 do we?" obviously enjoying her control over me. Swish. Smack.
"OUCH, that's 1 maim, thank-you very much maim," my ass already getting hot.
"That's better," as she rubbed the riding crop on my burning ass. Up and down the crack a couple of times as she did. Then without warning, swish. Smack.
Better prepared now, "That's 2 maim, thank-you very much maim," I responded.
She continued to smack my ass and alternately just rub it until the count of 10.
"That's 10 maim, thank-you very much maim." Now I could feel my ass really burning, something I thought I would have to get used to.
Leaving me bent over she pushed her chair back and stood behind me. While rubbing her hands over the red, sore ass and then in between them to caress the now raging hard-on, "OH this color looks good." Not sure if she was talking about the red of the ass or the color of my pink panties until she said, "But I do think we will have to get you a few more pairs." She continued to caress the ass as she spoke, which felt so good.
"Now stand up and lie down, I don't think these panties will last with you straining the front of them like that."
Moving over and straddling my head with her knees, her wet pussy just inches above my face; she reached down to stroke my hard-on through the fabric of the panties. Moving the panties to one side, she began to move her hand up and down the hard cock slowly. She reached back to raise her skirt up and over her hips. Slowly she moved her pussy down to meet the waiting lips. Immediately my tongue was licking her pussy from the bottom to the top, paying close attention to her erect clit, nibbling it softly. She leaned over to stroke and lick my cock, bottom to top, running her tongue all around the head. It only took about 10 minutes before I erupted into her mouth, both of us moaning so loud I was sure everyone in the building could hear us. Once done she licked my now deflating cock clean and placed it back into the panties.
Standing up and re-doing her skirt, "Much better, now they will last longer."
As I stood up she planted gave me a very passionate kiss, our tongues intertwining. Breaking away, she handed me the crop, "Put this away, I don't think we will need it for a while."
She returned to her seat and began reading the Scottsdale report, ever so often sneaking a look at my ass as I crawled back to put the crop away. I retuned to the side of her desk awaiting instructions.
After a few minutes she looked up, "This is great work! I am sure the company will go for this. As a reward we are going to take the afternoon off to go shopping."
Not sure how shopping was going to be a reward for me, since I hate to shop. Little did I know just how much fun this adventure was going to be.
"OK that will be all for now. There is other work to do now before we go and I need to get it done."
I put my clothes back on and returned to my desk, sitting gingerly on my ass. I diligently worked on the next 2 hours, with the shopping trip on my mind. It seemed like forever but 11:30, lunchtime, finally came.
Elaine came out of the office, suit jacket on and blouse buttoned back up, "Ready to go? Lunch will be my treat Sissy boy."
Without waiting for my response, she started for the elevator, giving me a great view of her hot ass. Quickly getting up I followed her.
Arriving at the restaurant, after a short drive, with her at the wheel, I watched the skirt ride up as she exited the car. Walking in front of me, she stopped at the door, waiting for me to open it.
"Thank-you Sissy boy," she said in the middle of the waiting lunch crowd. For the rest of lunch she continued to refer to me as Sissy boy, regardless of who heard. Her foot found the way to my crotch several times during the meal, caressing it gently.
The rest of the meal went events, unless you consider her calling me Sissy boy in front of everyone eventful. Elaine paid for the lunch on our way out, and to the car, we went, with me following her like a puppy dog in heat. Soon we were on the way to go shopping.
After a short drive, we arrived at what looked to be a warehouse with a single door. The only sign anywhere was on the door, which said, "You must be 21 to enter." This part of town I had not been in before. Entering I see that both walls are filled with all sorts of sex toys. Further on are isles of magazines and movies. Going to the back of the store, I see all sorts of lingerie outfits. The back wall has a few doors side by side, the dressing rooms I assume. Elaine started looking through the outfits, ignoring me for the time being. Taking the time to look around I notice about 10 other women in the store. I over hear a sales woman telling a customer that indeed this outfit is easy to remove when you dance. It seems that the local strippers use this store.
Elaine chose three outfits for a French Maids outfit, a schoolgirl outfit, a hooker's uniform, for me to try on. She hands them to me then points at an open changing room. I grab the outfits and enter the room. Putting on the French Maids outfit first, I open the door and try to stay inside as Elaine and the sales woman talk. I motion Elaine to come look at how the outfit looks.
"Sissy boy, how do you think we can see it with you in there?" Elaine says loud enough for everyone in the store to hear,"Come out here so we can get a good look!"
"Don't be so shy sissy boy! Turn around so we can see it all!" I do as requested and model the outfit for them. They reach up and run their hands over the outfit saying how cute it looks on me.
"Now bend over so we can find out if it's short enough."
Bending over so my pink ass is fully in view of everyone, I hear giggles from a couples shoppers near-by.
"That does look cute and short enough. It looks like your Sissy Boy has been bad already today."
"Yes Sissy Boy needed to be taught a lesson this morning, but Sissy Boy has been good since then," Elaine was telling the sales lady while she rubbed my ass, swatting it a couple of times. "Now stand up and walk around a bit Sissy Boy, I want to see how it looks."
Walking back and forth in fron
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