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The Fancy Dress Contest
Taylor is addicted to fancy dress competitions and Sophia puts in a real effort to make sure they walk off with the 500 first prize.


“I really don’t see why you are making such a fuss about it Taylor” Sophia said. Her face has the look that teenagers reserve especially for speaking to their parents.

“What you are suggesting is not like a night out Sophia.” I say, I am getting angry. Why can’t she just let it go. “What you are suggesting is totally different.”

Sophia just stares at me for a while then says. “You insist we go to every bloody fancy dress night in the county, it is always the same thing every time. SO how is this any fucking different?”

“Why are you pretending not to understand Sophia?” I’ve raised my voice but only slightly.

“I’m going to work” Sophia says then leaves without another word. The door slamming behind her says it all.

I still have an hour before I need to leave for work. I work at a supermarket in the local mall filling shelves. Mind numbing but we cover the bills - just about. 
Sitting on the sofa with a coffee I think over Sophia’s suggestion, I think over the argument. I am being a jerk I decide and text Sophia ‘I am a jerk’ 

‘I know’ she texts back. Two kisses...we are good.

‘Phoned for interview, talk tonight xxx’ I text. There really was no reason for an argument, all Sophia had suggested was that I go for an interview.

Sophia works as a stylist at the local hair salon, one of her customers had mentioned a local club has a vacancy for bar staff. Sophia’s plan is making more sense as I think it over again. 

I’m a wanna-be writer, the only time I get to write is in the evenings after work. Big problem is after I have been writing I cannot get to sleep, my mind is buzzing and my constant fidgeting in bed keeps Sophia awake.

Sophia’s suggestion was that I apply for a bar job she has heard of, 3 nights at the club would pay more than I earn in a week at the supermarket and as it is evening work I will have every day free to write. Calmly thinking it through now it’s sounding like a good plan to me as well. I can be such an idiot some times.

Sophia was right: 
I do insist we go to every fancy dress night. 
I do always go in a female costume.
I do like to dress up occasionally.

Why did I make such a fuss about being offered the perfect excuse to spend three nights a week femming up I wonder to myself.

Sophia’s customer Junie knows the manager at a club which attracts mostly LGBT customers. Off the record Junie said the club ideally want a tranny to balance up the bar team, but of course the club cannot advertise that which is why Sophia mentioned the job and why she was so certain I could easily walk in and get the job.

The interview is set, Sophia has spent time getting my hair styled just right and I am wearing one of her knee length skirts with a sloppy top. Underneath I wear what she calls ‘my little helper’ a thickly padded bra that adds a little shape to create my bust. I slip on a pair of Sophia’s lower heels.

“I think you only asked me out as we are the same size” Sophia says and smiles “same size and such a stylish dresser.”

“My hair looks stunning” I say “Now you have set such a high standard it is going to keep you busy if I get this job.” I keep my pale blond hair in a pony usually, just below shoulder, for the interview Sophia has styled it in gentle curls, my blonde beard is slow growing and tonight barely shows through my foundation - Sophia had suggested that I did not shave for a couple of days to make sure the bar manager realised I was actually a man. ‘Keep your voice deep or he might think you are a hairy lady’ Sophia had said with a cute smirk.

“You will have to learn to do your own hair, you might be leaving for work before I get home” Sophia says then makes a twirling motion. I do a 360 and a shimmy.

“You can be such a tart” Sophia is laughing now “a natural tranny…what do I see in you?”

“I appeal to your inner lezzer perhaps?” I want to say I love you but don’t want to sound that needy. Instead I say it inside my head.

Nerves have kicked in a little so I persuade Sophia to come with me, she waits in a nearby bar. I am out from the interview in a few minutes having been immediately offered the job, so fast Sophia is still on her first drink. She is sitting at the bar, a guy is chatting to her. I walk up and kiss her cheek.

She introduces me to him. “This is my boyfriend Taylor” Sophia says, she has a full on smirk.

Nothing new about Sophia ‘outing’ me, she does it all the time at fancy dress nights or if she ‘fems’ me up for a night of clubbing and dancing, and I get a little kick out of it as well. The guy shows his surprise and ducks out.

We sit at a table while I tell Sophia all about the job, I start the next night - Thursday till 11:30,  Friday, Saturday till 03:30. 
With 2 drinks inside me I say “I think this will work well, I am quite excited.”

Sophia waits up in our apartment for me to get home the first night, new job excitement fills my head as I tell her all about my first night at the club. We are getting undressed when I show her my share of the nights bar tips.

“Will you wear the same dress tomorrow night please?” Sophia says, it is simple black dress, an older one of hers. “Jazz it up with a belt, I haven’t enough clothes for the both of us.” 

We are laying in bed Sophia says that I need to get some of my own ‘work clothes’ as she put it, adding that I will need more undies as well. 

Next day she takes a couple of hours for lunch, I am loaded with bags as we hit one charity shop after another. We finish up at a department store where Sophia picks up a few bra and pantie sets.

“Is it OK if we both go in?” Sophia says to the assistant at the changing room. The assistant nods, we are standing in the change cubicle when Sophia says “Try this bra on first Taylor.”

I ‘Shhh’ to make her keep her voice down.

“Don’t be such a sissy, just try the bra on” Sophia says still at her normal volume. “Now try your shirt over it to make sure.”

She swishes the curtain open and takes my hand, a feeling of excitement sweeps over me as I realise I am being outed in a new place. “Just a moment Sophia…I want to take it off…” I’m purposely all whiney now.

“We haven’t time to mess around, I need to be back at work” Sophia says as she puts the undies on the counter “He is wearing this” she puts the tag from the bra I’m wearing on the counter.

With my new undies paid for I am ready to head home. “I’ll see you later” I say

“Oh I forgot to tell you” Sophia said “I booked you in with Angela at the salon for nails and studs in your ears, you will look soo cute at work tonight.”

I keep the bra on for the afternoon, Sophia isn’t home by the time I head off to work in a ‘new-to-me’ skirt and blouse. We really don’t get much time together until Sunday as Sophia is at work all day and me all night. 

Sunday morning Sophia asks me to put on a fashion show for her with all my clothes from the charity shops. She is still in bed watching when she decides the leggings and a sloppy top is her favourite for ‘casual’ and to keep it on ‘for now’. All thoughts of sleep are gone for now and I go to tidy the apartment. Sophia is wearing a similar outfit when she comes out of the bedroom. 

“Lets have a wander around the shops and get lunch out, you can treat me with your tips” Sophia says.

“I’ll change” I say

“No, I like that look…tranny or heroin thin girl…that will keep them wondering” Sophia says then throws her cute smile. “Tranny with his fag hag would be my guess.”

“Which one looks the engagementest?” I say. We are in a fashion accessory shop, I am looking at a tray of bling-rings. Sophia looks confused. “Most like an engagement ring?”

“Is engagementest even a word?” Sophia says “you are really sweet…but I’m not sure we are quite there yet Taylor.”

I explain the ring is for me, Sophia bursts into uncontrollable laughter when I explain that it is for me to wear at work. I hoped it might stop people hitting on me.

“People?…what sort of people?” Sophia is beside herself, barely able to keep from laughing. 

“Customers” I say.

“Men or women…” The laugh escapes Sophia. “Silly me…I doubt many women would” laughing she continues “…you want to buy a ring to save your ring”

“Just fucking customers…it does not matter” I say low and close to Sophia, she knows I’m angry and points out 3 rings.

“I am sorry Taylor, how about this one, look, they have matching drop earrings. Should I get a ring as well?” Sophia says.

“Do people hit on you then?” I say as jokily as I can. Sophia ignores the question.

My writing is coming along, I’ve been working at the club for just  over a month now. Money is easier with my increased wages and tips. The ‘h’ key on my laptop is being temperamental, why couldn’t it be the ’>’ I wonder. Time to begin saving for a new laptop.

Sophia was right, the gap between writing and bed has let us both get a good nights sleep - well not on Friday and Saturdays when I make Sophia breakfast before going to bed. I sometimes  notice a smell of alcohol in the bedroom in the mornings and assume Sophia has a glass of wine in some evenings when I am at the club.

“It’s Anns birthday Saturday, we are having a girls night out” Sophia says as she is leaving for work. “We might pop in to see you for a while” 

Pausing swearing at my misbehaving laptop keyboard I say “it will do you good to get out for a change.”

“It’s sweet Taylor that you think I sit in watching television alone every weekend. “ Sophia says as she leaves for work. 

That’s new I think as I am spraying switch cleaner into the keyboard, Sophia has never been in the club. 

For once Sophia is home before I leave for work on Saturday. 

“Quiet at the salon for once” she says, then takes a new shift dress from a bag “a little present…wear it for me tonight?”

I detect the rising inflection and say “it’s really pretty” then wondered when I started speaking like that. Sophia did my hair for me then make-up as well as I sat wearing just my gaff under my bathrobe. As I dressed she added new forms to my bra then handed me a new pack of seamed hold-up stockings. 

“They feel heavy and look bigger” I said.

“I want to be proud of you…you know…looking your best for me tonight” Sophia says.

“This dress is really short on me even before I put my heels on.” I said as I looked in the mirror. 

“It looks cute on you…I going to wait up for you, slip your panties down and have my wicked way with you.” Sophia said, paused for effect “but if you think it’s too short why not wear your black one, I quite like that on you as well.”

“I will have you added to VIP list, I’m on table service tonight” I say

I know what Sophia’s ‘quite like’ means and wear the short shift dress to make sure of sex. I’m feeling self conscious about the forms, the are bigger and I realised when freshening my make-up at work they have erect nipples moulded in. My thin bra and dress material do nothing to hide them, for the rest of the night I feel that everyone is staring at them.

Sophia arrives at the club just before 2am with 4 other girls, she is the worst of the group -  bordering on drunk and swaying. I arrive at their booth. Sophia is sitting next to the aisle talking to the group, I wait to be acknowledged. 

“My boyfriend works here, I can’t see him” Sophia makes a theatrical sweep of the room with her head. 

“Oh look here he is, right here…” Sophia is drunk loud, she stands unsteadily and kisses my cheek. “He does look sweet. Short little dress. Fake engagement ring. What a prick teaser. A little tarty but sweet, I like my trannies like that you know, what’s excited my baby? Look at your hard nipples…”

Two of the other girls slipped out of the booth to quieten Sophia a little then they bustled her to the restrooms. I took drink orders from the table then made sure someone else served the table. The club was heaving as usual and next time I looked they had left the club.

The argument began mid afternoon next day, well Sophia was in bed asleep and groaning until then. Arriving home after the club shut to find her comatose in bed had only served to increase my anger at her behaviour. I had ripped the dress in two and cut up the awful nipple tipped breastforms before slamming out of the apartment.

Nearly a whole week had passed since we spoke, I had blocked Sophia’s number on my phone and ignored her texts. I had sofa surfed until Thursday afternoon when I needed to dress for work. 

I let myself into the apartment not knowing what to expect, I was hoping Sophia would be at work, I was out of luck. The smell of cooking filled the apartment, I turned to leave.

“Please wait” Sophia said. 

Make-up did little to hide her puffy eyes. I shook my head. “There isn’t much to say”

“I hoped you would come back for your work clothes, I have apologised to your boss for…well…being loud and embarrassing” Sophia said “I asked him if we could have tonight to talk if you came home.”

“I doubt you even know what you did and said” I said

“Ann showed me…she was recording her birthday on her phone…now I am even more ashamed” Sophia said.

“You’ve got it on fucking video?” I said as I began to collect some work clothes together. Sophia had washed and pressed every one of my clothes.

Life in the apartment was fragile to say the least, I agreed to move back in after more apologies were followed by sex. Sophia had gotten back to her ‘old self’ well better than that really, she had become much more attentive, taking more interest in my writing and even adding her tips from work to my new laptop fund jar. 

Gradually I began to get over the shame of that night.

“You could always look for another job…you know…go back to the way we were before…” Sophia said out of the blue one night as we watched TV. I said that I liked my job and the people at the club, mostly they are all really nice to me. “You get the odd difficult customer” I said.

“Yes I was real bitch…” Sophia said. “It still hurts me when I look at that.”

“You still have the video?” I say. 

“I mean think of it…see it in my mind” Sophie said blushing. “Can I say something?” 

I nodded and waited.

“You hardly ever wear mens clothes, like tonight you are wearing a bra, panties, hose, a dress and it’s not even a work night. I can’t even remember the last time you wore mens clothes” Sophia said. “And when we go shopping, people, you know friends mention it.”

“OK, only to work” I say.

“Now don’t be like that Taylor, just not all the time that’s all. People have begun asking if you are a transvestite as well” Sophia said.

“As well as what?” I say

“As well as a crossdresser of course silly” Sophia says

“They say that?” I say

“…I really don’t care what they say, I like your fem side.” Sophia smiled. 

A public holiday neared, with people not working on the Monday the club decided to open on the Sunday night, an extra night, extra profit and extra wages and tips for me. Our manager asked for suggestions to fill the club on the Sunday, I suggested a fancy dress competition of course.

“There is going to be a fancy dress competition” I say.

“And we are going of course” Sophia said. 

“500 first prize” I say.

We chatted at every opportunity about costumes, we both knew our theme would be same as always. Sophia checked the charity shops for ideas as I needed a new costume and came back with a peach colour satin bridesmaids dress with a modest round neck, fitted to the waist and half sleeves. Whoever the dress had been made for must have had a massive bust.

“Mistress and Maid as usual, your dress will need some alteration of course.” Sophia said as I tried it on.

We had done well with mistress and maid characters at other fancy dress competitions and we felt quite confident about the clubs competition. Sophia already had a really nice mistress outfit and would wear that again. The bridesmaid dress was a bargain and there is a seamstress in town who does alterations. Sophia came with me for the fitting.

“Waist needs to be let out, we can’t even fasten it and the bust needs to be made smaller” I said as I stood while the seamstress tucked and pinned the bottom hem.

“No that’s OK” Sophia said. “It came complete with the undies, waist will fit perfectly when you are wearing the corset.”

The alterations would take 2 weeks, the competition was in 3 weeks.

“Plenty of time if any final alterations are needed” The seamstress said.

“Why don’t you put that little grey minidress on and find a pinafore while I shower” Sophia said. It’s the Monday after we went to the seamstress, we had an evening at home planned. Pasta and sauce, an evening watching TV. Sophia showered while I changed out of my mens clothes. She was wearing her mistress costume when she came out of the bedroom. 

“I just thought I would check it for size” Sophia said. “I like my maid in grey, I like my maid in grey so much I have a present for him.”

‘Thank you mistress” I said - we have played this game before. It always ends well.

“Are you wearing panties?” She asked. I nodded “bad, bad maid. Take them off and bend over”

Two gentle slaps from her riding crop, just hard enough to sting. I was led to the bathroom, I knew what was coming, my hard cock tented out the front of my dress. 

“Over the sink” Sophia instructed in her sternest voice. 

I was ready for an edging, my cock is over the sink. Sophia squirts lube in my hand then on my cock, I wrap my hand around my cock, Sophia wraps her hand around mine then she begins  slowly moving my hand up, down, up, down…

“Don’t you dare cum” Sophia says. Around my hand her grip builds little by little, her speed increases little by little.

“Mistress” I say. I try to let go but Sophia’s grip around my hand is too tight.

“Be silent sissymaid” Sophia says

“Mistress, mistress…please stop” I say in desperation even though I know it is already too late.

Sophia lets go, I don’t have any willpower to stop and continue to finish the wank as I pump my load into the sink.

“You bad maid…I told you not to do that.” Sophia says as she slaps my arse, hard this time. “Now clean yourself up and lay on the bed face up.”

I see it on the bedside, we have talked about chastity play before. “Please forgive me mistress” I say playing my part in the game. ‘I promise it won’t happen again.”

“Silence…you cannot be trusted, right in front of me you satisfy yourself, now I will make sure you do not disobey me again.” Sophia says.

I cook the dinner, do the dishes, clean the kitchen, bring Sophia coffee, tidy the living room all the time curtsying and calling her mistress. My cock is straining against the cage, trying to get hard, I love this game. 

I continue playing my part and instead of joining Sophia in front of the television I bustled around until we headed for bed. I spooned up to her, began caressing her hip.

“I’m ready again Sophia” I said as I strained against the cage.

“Ready for what?” Sophia said.

“I am ready to be unlocked mistress” I say

Sophia sat up, smirking, I could see she was beside herself with excitement. 

“I am not your mistress. That game is over Taylor we are not wearing our costumes” Sophia said.

“Come on unlock me, I want to please you…” I say

“Then you will have to think of another way to please me tonight, I think your key is still at work” Sophia said as she turned the light off and began to spread her legs.

“You left it at work? Why? How will I get it off, and how much did it cost?”

“So many questions…I must have left your key on the side when I was showing the girls…”

“You showed them this?” I say, not sure if it is anger, arousal or shame I can feel building inside me.

“They said I would never get you to wear it” Sophia paused to giggle “they will be surprised when I tell them how willing you were to lock your cock away. It was the last chastity device they had in the adult shop so price is unimportant and in answer to your most urgent question, without the key I was told you will definitely not be able to remove it.”

“You mean I will have to wear this all night?” I say

“No Taylor…you will wear it until you earn release once we are mistress and maid again” Sophia said, she was giggling again. 

“When will that be Sophia?” I ask even though I can guess, she continues giggling “No…not the fancy dress competition…please Sophia…please be reasonable…that’s weeks away.”

“Your constant begging is unpleasant for me to hear, no more about it please, not another word, let's concentrate on winning the contest shall we?” Sophia said, kissed my cheek then added “then you can get that new laptop with the winnings.”

I had asked several times about the second fitting for my dress but Sophia repeatedly insisted it would be fine. 

The day of the fancy dress competition finally arrived. Sophia was home for the whole day, she had collected my dress and now we both needed full hair, nails, make-up etc.

“I love this perm on you, just above shoulder or perhaps mid neck might look better” Sophia says to herself as she snips away. 

“The perm worries me a bit Sophia and you seem to be cutting a lot…” I say. 

Before I can finish the sentence Sophia says “Who is the hairdresser?”

I sit quietly as she works away. As usual before every contest we enter the mirrors have been turned to the wall or covered. Sophia hates it when I give her advice and we both love the ‘big reveal’ at the end. Anyway hair is not that big of a thing as lots of guys are sporting curls this year. 
I haven’t shaved for two days. 

Sophia says “I am tinting your stubble and brows dark to give a ‘male contrast’ in case anyone thinks you are just woman wearing a sissymaid dress.”

“You have said ‘sissymaid’ a couple of times, how does that differ from a maid?” I ask.

“I’m not sure, the person in the adult shop used ‘sissymaid’…do you think it is what they call a man in chastity dressed as a maid?”

“We will have to look on the internet” I say “I am so looking forward to getting this chastity thing off, I am horny every second I am awake. You have got the key here?”

“I like the sound of sissymaid, that is what we will enter as ‘Sissymaid Taylor and his Mistress’

“The key?” I repeat.

“Are you really desperate to cum” Sophia says.

Hopeing slipping into character will help I nod and say “yes mistress, if you allowed me to I would beg you for release”

“Do you regret entering chastity?” Sophia says. I nod “how much?”

“I wish more than anything we had never started…please let me out, I’ll do anything mistress” I say in a whiny voice.

“Shall I tell you what the sales associate said when I bought it?” Sophia said.

I nod “please mistress”

“Chastity only begins when you no longer want it” Sophia smirked “…and so chastity begins…”

“Have you seen the time?” I say. The clock is showing 7pm, I need to be in work at 8.

“My sissymaid is all ready apart from his undies and dress” Sophia says. “I am coming along later, shortly before 10 when the contest starts. I want to make sure I am fully in control and sober this time.”

I stand and slip my bathrobe off, my hair feels massive and cannot feel it on my shoulders, I sit on the edge of the bed and slide my seamed stockings up my hairless legs.  I am excited, I can’t wait to see us all finished. Sophia takes the corset from the bed, I’ve seen it laying there for a while, it looks complicated to say the least. My arms go through the shoulder straps, the front clips together then Sophia begins tightening the laces at the back. 

“How am I going to get this off.” I say

“Let me worry about that sissy” Sophia says, she runs a measuring tape around my waist. “A little bit more.”

“It’s already uncomfortable, hard to breathe” I say. She measures again then ties the laces off. The front busk is so tight I will never be able to get out of the corset without help. Sophia puts two massive forms in the corsets cups. 

“They are too big, I won’t be able to see over them to serve customers” I say. “They must have cost a lot like the chastity thing, where did you get the money for all these things Sophia?”

“Do stop moaning sissy, they are only D’s or perhaps double D’s” Sophia giggles “I borrowed the money from your new laptop saving jar - just until we win that 500 first prize…let's get your titties settled, that’s better, now shoulder straps.” She steps behind me and tightens the straps. 

“How much did you take from the jar? I can’t lift my arms far Sophia” I detect a whine in my voice that I didn’t put there.

“Thats it...stockings clipped to your corset, seams nice and straight. Dress next…step in” Sophia says “nearly ready then the big reveal…excited?”

I nod and step in, guide my arms in and feel the back being buttoned up, the neck comes up higher than before, almost like a polo neck. Sophia pauses, the neck tightens then a click.
“What was the click?” I ask.

“ A little catch to keep the collar in place…show me a nice deep curtsey…good, hold it there while I clip this on…oh your little maids mop cap looks so sweet. The seamstress made the cap and garter from the material she cut off the bottom”

“We are all done…your shoes are in the hall, ready  Sissy?”

“You forgot my panties” I say 

“You don’t wear panties with this costume sissy” Sophia says as she slips the garter up my thigh.

“Please don’t call me sissy all the time” I say, that whine is back in my voice.

“For tonight you are Sissymaid Taylor” Sophia says.

I step into my heels.

Sophia puts her shoes on “Perfect timing, I’ll drive you to the club”

“We haven’t had the reveal” I say.

“No time for messing about now, you’ll be late for work. I’ll take a photo, show you on my phone when we get there, trust me you look a perfect sissymaid.” Sophia says as she does little hops in excitement. We chat about how Sophia wants to film me walking from the car to the club.

I get out of the car, the club is a short walk and Sophia has gone on ahead to video me getting out of the car and walking along the street, we have run through what scenes Sophia wants to get. I am excited. I love competitions. We need to win tonight if only to replace my savings. Passers by stop and stare, I hold my head high to make sure they can see my look. A group of people have walked in front of her phone, as I near Sophia she calls out for me to repeat, I go back to the car and begin walking. 

Bob crosses the road, I know him from the club, he is one of the straight customers who pop in the club at the start of the night before moving on elsewhere, we chat briefly. He walks on and I continue towards Sophia, she gives a silent thumbs up from behind her phone and I stop a few paces away. 

I curtsey and say “good evening mistress”

“Who was that man sissymaid?” Sophia says

“It was Bob mistress” I say in character

“Tell me did Bob like your sissymaid dress” Sophia said

“Bob said how much he likes my sissymaid dress Mistress” I said even though he said no such thing. I was having fun being in character

Sophia says “did he ask if you would suck his cock?”

“No mistress” I say then look down at the pavement “why are you asking that mistress”

“Does my sissymaid want to suck his cock?” Sophia says.

“No mistress” I say. Even though I am shocked at the off script questions I try to keep in character. 

“Are you sure?” Sophia says

“Yes mistress” I say

“YES???  You want to suck his cock?”” Sophia says. She looks shocked.

“Mistress I meant I am sure I will not”  I say as Sophia waves her hand towards the steps.  

Resuming the routine we planned I climb the four steps then turn in the doorway back towards Sophia and curtsey to her “Good night mistress” I say.

Sophia had crouched down as I had my back towards her, now she stood and bounced up and down with glee, a smile filled her face. I walked back down the steps, Sophia’s phone flashed a couple of times. She held up her phone to show me the pictures.

“What was all that about sucking cocks” I asked softly “Can I see the video?”

“I imagine sissymaids suck guys off and I was having a little fun, your face was a picture, I cannot wait until you see it” Sophia leant in and air kissed both cheeks “mustn’t spoil your make-up…I need to go and get into my costume this very minute - I’ll show you the video later.”

By 9:30 the club was as busy as a Saturday, there were only 5 entries for the fancy dress. The bar quietened as time for the Fancy Dress Contest drew near. I checked out the other entrants and began to feel confident of taking first prize.

I joined Sophia who had arrived and was sitting at a table with Ann and Angela from the salon and three men including Bob who I had spoken to earlier. Sophia introduced me in turn to each woman and her boyfriend, so 2 couples, she finished the introductions with ‘and you know Bob.’ said with a smirk. 

“May I have a word in private mistress” I said keeping in character, we stood about three feet from the table.

“From across the bar you looked like three couples” I said. “What the fuck is going on with Bob…I may look like a sissymaid for the contest…” was as far as I got before Sophia slaps my face.

“How fucking dare you embarrass me in front of my friends and workmates” Sophia begins, she is not keeping her voice down, heads swivel towards us, 

“Bob is” Sophia takes my left hand “making sure other guys don’t hit on me as I do not wear a fake engagement ring…” She held my hand out towards the table. “Enough of your nonsense sissymaid, now apologise before you sit.” She is gently tapping her riding crop against her thigh. 

 I say “yes mistress” curtesy and apologise to the table, my turn to overplay my part I decide and I say “thank you Bob for protecting my mistresses honour.”

The table erupted in laughter.

My cock was ready to explode in its cage, this was role-play on steroids. Apologies over I sat between Ann and Angela.

“May I sit next to Bob sissymaid?” Sophia said, she had a smirk. I nod in agreement and look down. “And can I apologise for us causing him embarrassment?” 

I nod in agreement again. I know Sophia is planning something and I do not have to wait long.

Sophia says “please excuse my sissymaid’s bad manners Bob” then leans in, they kiss.

“You will have to think of your own way to make it up to Bob sissymaid” Sophia says, the smirk becomes a smile as she looks around the table. 

Everyone is giggling, the mood lightens as I accept compliments from Ann and Angela about my costume, an announcement came over the speakers that the contest was beginning. Sophia and I made our way to the stage area. We are last up and stand waiting. Each entrant stops at the microphone, introduced themselves outlining what their costume is then exit the far side of the stage. 

“Right remember the plan, you stay one step in front of me to my left, I’ll use my crop to let you know I am close enough, when I tap the back of your thigh with my riding crop you kneel” Sophia said for the twentieth time. 

“I understand and will obey mistress” I say

Sophia is waving, gesturing for someone to join us as she says “I forgot about your video”

Of all people it was fucking Bob who was walking over.

“Bob be a honey and show my sissymaid the video” Sophia says. “Bob is a wizard with computers, he’s added titles and everything.”

I am watching as Bob holds his phone up for me to see, all pretty much as expected. Pink titles fade and my walk from the car begins. I am thinking how much I hate fucking Bob as I realise what a ‘wizard with computers’ he really is. The video is playing on a loop:

…I curtsey and say “good evening mistress”

“Who was that man sissymaid?” Sophia says

“It was Bob mistress”

“What were you and Bob talking about?” Sophia says

“Bob said how much he likes my sissymaid dress Mistress”

Sophia says “I expect you asked to suck his cock?”

“Yes mistress” I say then look down at the pavement.

“Does my sissymaid want to suck his cock tonight after the fancy dress competition?” Sophia says.

“Yes mistress” I say.

“Are you hoping he will fuck you in your sissy pussy?” Sophia says

“Yes mistress” I say

“Then you have my permission to suck his cock real good as your reward for being such a good sissymaid” Sophia says.

“I am sure I will Mistress”  I say then curtsey. 

On screen I climb the steps, from the low angle Sophia is holding her phone my bare arse comes into view, at the top step I turn’ curtsey and reveal my shiny bright silver chastity to the camera.

The bastard has cut, swapped, dubbed and copied the video. Sophia has re-recorded her voice saying different things. As if I have been frozen I can’t look away. I can’t stop watching. I can’t even see the joins in the edits.

Sophia pokes me in the ribs “sissy…we’re on”

My head is in turmoil as I manage to lead out onto the stage, as planned Sophia is a step behind me. For now I try to forget all that has gone on in the last hour, the show must go on. Then I begin to wonder if this is all a cruel joke, perhaps later the seven of us will sit around the table laughing…

“Kneel sissymaid Taylor” Sophia says as we arrive at the microphone.

A blinding pain explodes in my thigh as Sophia brings her crop down. I let out a whimper.

“Did I give you permission to make a noise sissy?”

“No Mistress Sophia” I say then look down, in the corner of my eye I see a mans legs standing next to Sophia.  I realise the bottom of my short skirt is stiff enough to stay up exposing my chastity device to the audience. 
I begin to move my hand from my side to hold my dress down but Sophia rests her riding crop against my arm. Not wanting another swipe from the crop I freeze. 
Thoughts run through my head…this is not what we planned…who is the man…how much worse can it get…

Sophia begins speaking…

“Good evening I am Mistress Sophia, to my left is my cuckolded sissymaid whom you may recognise as Taylor who works behind the bar. To my right is my alpha male lover Bob…”

All I can hear is the steady ptt, ptt, ptt sounds my tears make as they land on my beautiful peach colour satin sissymaid dress.
Thanks Ash for another exciting story
Thanks for putting this up for comment, Ash. A real rollercoaster ride (for Taylor, in particular).

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