Seven days to sissyhood. Day 5
WEDNESDAY
I decide to go to the office early, then I don’t have to walk past Jane, as I park my car and get out I feel one of my suspenders come loose, there were a group of c***dren walking past so I could do nothing about it, but the building where I work is just across the street, and when I get in there I should be able to ‘adjust’ myself.
I swipe my security pass through the reader, and the doors come open, just my luck the security guard was at his desk, I nodded to him and he nodded back. I will have to wait until I am in my office to adjust myself.
I walk into the outer office, and at that moment, I felt the second suspender come loose, and I could feel the stocking begin to slide down my smooth shaven leg.
Almost safe, but as I look up I see Jane already at her desk, and she was looking directly at me.
There was no-one else in, why was Jane so early?
“Come and stand by my desk Miss Thorne,” she said.
Why was she talking to me like that, I am her boss, but I felt unable to do anything except say “yes Miss Jane.”
As I stood where directed, knowing my stocking was slipping lower, and wondering if it might fall down so low, it might show at the bottom of my trousers she said “I have had a nice conversation with your wife, Susan, or should I say your MISTRESS.”
My heart sank, I wondered if when I heard my wife speaking on the phone yesterday, she was speaking to Jane, maybe even telling her that I was standing in the corner of the bedroom as she spoke.
“She told me what a sissy you are, and you need to be humiliated. I want you to drop your trousers, and show me what she has had you wear today.”
I could myself blush, but knew I had to obey.
I stood in front of her knowing one stockings was attached, and the other was sagging around my knee.
She laughed “You are such a sissy, you can’t even dress yourself. This is how stockings should look.”
And with that she unzipped her dress, and it fell to the floor, and revealed that she was wearing a black leather corset, red knickers, black stockings.
As I said she is more of a Rubenesque kind of figure, and her tits were barely contained in the corset, and she pulled her suspender strap and ‘twanged’ it, “This is how a suspender should be attached.”
“Now pull your stockings up and attach your suspenders properly.”
She watched as I re-attached my suspenders to my stockings “From now on you will report to me every day for a ‘uniform inspection’, do you understand?”
“Yes Miss Jane,” why was my cock so hard being talked to by someone who I should be the boss of?
She opened one of the drawers of her desk and got out a pink leather dog collar, which already had a pink leash attached, and I saw on the collar it had the name ‘Fifi’ stitched on.
She put the collar around my neck, “Kneel down sissy.”
I did as ordered and she wrapped the leash around one of the handles of her desk.
“You normally have a cup of tea in the morning, don’t you sissy,” she said.
“Yes Miss Jane.”
“I can’t be bothered to make you a drink, but you can have my tea, I will want your tongue nice and wet for your duties.”
She then got her cup of tea, and poured it into the saucer, and placed it down in front of me, “Drink up sissy.”
I went to pick up the saucer and she said “No sissy, bend down and lap it up.”
I did not know how long before someone else came into the office and saw me in this humiliating position, so I started licking as ordered.
When I had finished Jane said “Thank me for letting you have my tea.”
“Thank you Miss Jane for letting me have your tea,” will this torture never end, but my cock is still trying to break free from it’s cage, and my balls were aching.
She turned her back on me so her bottom was directly in front of my face, then hooked her fingers in the waistband of her knickers and pulled then down. I so wanted to kiss her bottom, but did not dare do anything that I was not told to do.
Then she turned to face me, and she put her hand in front of her pussy as though being coy, and then slowly moved her hand away, and revealed a trimmed pubic bush, with only a thin strip of hair leading down to her pussy lips.
“Like my cut,” she said.
I nodded my head “Yes Miss Jane.”
She slapped my face “What do you mean just saying ‘yes Miss Jane’, I told you to lick my cunt, get on with it you sissy”
I closed my eyes and bent my head to her pussy and immediately started licking her pussy lips, after being married to Susan for so long and only having her pussy to lick, it felt so different, the taste and smell was different, even how her body reacted to my tongue was different.
I heard a voice behind me “We know who the sissy is in the office,” I recognised John’s voice. “Are your balls aching Les,” that was Peter. When did they get in, how much did they see? Both their statements were correct.
Jane shook my shoulder, I took it as an instruction to lick harder, so I licked harder and faster, she shook me harder and I opened my eyes.
I was in my bedroom, my wife standing over me with just a towel wrapped around her, smelling fresh from the shower “You slept through the alarm, I have had my shower so it is clear for you, you wouldn’t want to be late for work, you never know Miss Jane might have to punish you.”
The dream still felt so real, and my heart was pounding from what I had just imagined, and the thought of what the Jane in my dream would do to me made me feel weak, and I was glad when Susan put on her dressing gown and went downstairs as I did not feel capable of getting out of the bed at the moment.
It took a few minutes before I felt capable of getting up, but knew I had to face the day, and had my shower.
After having my shower, I went back into the bedroom, and as usual I saw my clothes laid out, the suit was normal, she had also laid out a pair of white satin knickers, a white lacy suspender belt, black stockings, and also a white lacy bra!
A bra, she could not be serious, but I know I cannot argue, I usually lose anyway, I got dressed and hoped that as it was white it would not show through my shirt.
When I was fully dressed I looked in the mirror, and there was no mistaking the outline of the bra under my shirt, I tried putting on the jacket of my suit, but there was no way of disguising, I WAS WEARING A BRA!
I thought if I went downstairs, dressed as she wanted, it would show I was following her orders, but showing wearing a bra was not practical, she might let me off.
I went downstairs, and she looked up as I came into the room, but passed no comment.
“Mistress,” I said.
“Yes.”
“You can see my bra.”
“Yes pretty isn’t it, I must admit when I saw it in the clothes that you had kept hidden, I thought it was pretty, I like the lacy cup of the bra, so feminine, and so revealing, I thought about getting something like that for myself.”
This conversation was not going the way I wanted.
“But you can see I am wearing a bra,” I tried stating the obvious.
“That is the problem we women have, wondering how much of our lingerie we can display to keep men interested, but not too much that looks tarty,” was her reply, “I don’t think it looks too tarty.”
“Yes but ‘I’ am wearing a bra,” stressing the word I.
She sighed and said “If it bothers you so much, you can wear a jumper as well.”
“Thank you Mistress,” I said as I sprinted upstairs.
As winter was approaching it was getting colder, and it is not as though I have never worn a jumper to work before.
I put a jumper on and was pleased that it was not totally obvious that I was wearing a bra, if you looked closely you could just about make out the straps, but if I kept my jacket on I am sure I will get away with it.
I have never been so glad to wear a jumper, I go downstairs and look at my wife and wonder if she is wearing stockings again today.
As though she is reading my mind she bent down to pick something up from the floor, and kept her legs straight which caused her skirt to ride up at the back, and I could see the tops of her stockings being pulled up by her suspenders.
She looked over her shoulder at me , and could see exactly what I was looking at. “Oops,” she said “I had better not do that when Rob is about.”
If only my cock was free I would have shown her exactly what I though about the display she was giving, either I would have fucked her, or at least wanked myself while looking at her.
As it was all I could do was to suffer more pain from my cock as it pushed against it’s prison bars, and my balls as they wanted to release the cum that they had been storing for the past few days.
As we left the house and the door closed, the knowledge that I could not go back in unless she let me crossed my mind.
As I parked up outside the office building, the dream I had popped into my mind, and I got out of my car, half expecting to feel a suspender strap come loose, and the feeling of relief as I walked to the office all the suspenders pulling against my stockings as they should.
I entered the building, and went into the outer office, and there was the normal hum of work going on.
As I looked at Jane at her desk I thought ‘I will say to her today about calling me Les again,’ but unfortunately the though of her standing over me wearing her leather corset came into my mind as well.
She looked up and said “Morning Miss Thorne.”
I heard myself say “Morning Miss Jane.”
FUCK, I will definitely say tomorrow about using my first name.
I went to walk past her desk and into my office when she said “Miss Thorne, I have something for you,” and opened a drawer in her desk, it was the same drawer that ,in my dream, she kept the pink dog collar and leash
I could feel my heart pounding, almost thinking she would be able to hear it.
Fortunately all she pulled out was the report she had been working on yesterday. “There are a few queries I need your help on.”
I stood next to her, and was aware that my stocking straps would be at her eye level height, and began to worry that she might glance and see the obvious sign of a suspender strap, or even accidently her shoulder my brush against my crotch, and feel the hard metal of my cage.
I did enjoy the view down her cleavage, and could even make out that the was wearing a white bra, and made me think that we were wearing the same colour bras.
Thoughts like that did not help my situation.
I could feel I was beginning to sweat, and I hope the answers I was giving her made sense, but all I wanted to do was get into my office.
When she finished with her queries, I took the report, and went into my office.
As I was about to sit down, and to be honest I did feel like collapsing into my chair, I remembered what happened yesterday when a suspender came loose, and sat down with more thought.
It was only when I was sat down I realised what I had done.
I had brushed my hands down the seat of my trousers, because I remembered being glad that my suspenders felt taut so they were firmly attached to my stockings. But that is the action a woman does as they sit down, they make sure their skirt if properly underneath then before they sit, it was such a feminine movement, maybe as I was wearing a dress all the time at home, my actions were becoming more feminine.
I can’t walk like a man, and I can’t even sit like a man, where is this going to end.
I look through the windows of my office at the other workers, but no-one was looking at me so I can only assume my actions were not noticed.
I buried myself in my paperwork, hoping the distraction will take my mind off my situation, it did partially work, but every breath I take makes me aware of the constriction of my chest that my bra causes, any slight movement of my legs, pulls on my suspenders, and I don’t know if it is just my imagination, but I am sure I can feel the lace trim of my knickers, gently tickling the tops of my legs.
My office phone goes off, and as I reach over to answer it, I feel my nipple rub against the lace cup of my bra, and the thought in my mind ‘do women’s nipples rub in their bras, or do their tits fill the cups of their bra so they are not rubbed?’
My mind was thinking of that as I was answering the call, so god knows what gibberish I was saying on the phone, all I was thinking about was going behind Jane, reaching my hands around her, holding her tits in each hand, each tit was more than a handful. Feeling her nipples and asking if her nipples rub against her bra.
It was later that morning that my phone went ‘Whit Whoo,’ and the message ‘Picture time sissy,’ was displayed.
As I walked past Jane I mumbled ‘just popping out,’ to which she just said ‘ok.’
As I went into the toilets, there was someone there, so I slipped into the cubical, and then found the extra problem of having a jumper on caused for showing my lingerie. I was trying to be quiet, people expect a certain amount movement, but what I was doing was unusual.
I could still hear the other person was there then it struck me, the camera makes a noise when you use it.
I was thinking, ‘have a piss, and bugger off,’ but the time was ticking away to the point I knew I had to do something, so tried to position the camera, and as I took the picture, coughed in the hope it hide the sound, then quickly sent the picture.
As the person was leaving my phone when ‘Whit Whoo,’ again, if the person heard or not I don’t know, but when I looked at the message it simply said ‘No Bra?’
When I took the picture it obviously did not show my bra, so I took another picture, making sure my bra was on display, and sent that.
I sat waiting, wondering when I could get dressed again, and it was almost a relief when I heard ‘Whit Whoo,’ and this time the message ready ‘Well done sissy.’
I got dressed, and fortunately there were no other incidents during the day, my wife did text me another time, but was able to take the picture with no problem.
I went home slightly later, as I did not want to be caught waiting outside my own house again, and I was relieved to see my wife’s car already parked.
Before I got out of my car I looked around to see no-one was about, and quickly rang the doorbell.
I began to sweat when the door was not immediately answered, and I was scared to ring again, in case it annoyed my wife, but was coming to the point when I had to do something, when I saw through the frosted glass of the front door, the shadowy shape of my wife coming.
She opened the door, just enough to peep round the door “Yes,” she said with a smile on her face.
“Please can I come in,” I asked.
“Ask me properly,” she replied.
I looked round, knowing the longer I left it the more likely of someone seeing me at my own doorstep.
“Please Mistress can I come in,” I was having to beg to come into my own house, but for some reason my cock loved it, I could feel it throbbing against it’s cage, and my ball aching in sympathy.
She opened the door and I quickly entered.
She closed the door behind me, “Now thank me for letting you in.”
“Thank you Mistress for letting me in,” I replied.
“On all fours, and kissing my feet,” she said.
“But Mistress, someone might see me through the glass.”
“Would you prefer the door open so they can see you clearly,” she said as she went to open the door.
I immediately dropped to my knees, started kissing her feet, and between kisses said “Thank you Mistress for letting me come in,” knowing the quicker she is satisfied with my humiliation, the faster she will let me into the house properly.
When she was satisfied with my humiliation, she said “I will have to think of a way of you coming in, without me being at you beck and call.”
In my mind I did think ‘if you give me my key back then you would not have to open the door for me,’ but I did not have the courage to say anything.
“I have laid your clothes out, so get dressed and then we will see what we are going to do this evening,” she said.
I went upstairs, and I was almost thinking of the tennis dress, and the shoes as my uniform.
When I had got dressed I went downstairs, and my wife pointed in front of her, so I stood where she indicated.
She kicked her shoes off and said “it does feel good to take the heels off, they do make you feel feminine, but can be uncomfortable.”
She made no indication that I could take my heels off so I just said “Yes Mistress,” as I picked her shoes up and tidied them away, then returned to stand in front of her.
“I have been thinking about what you said yesterday about you needing some ‘relief’, and I don’t want you in discomfort, so as long as you behave yourself this evening, I think I can help give you some relief.”
I have never felt so happy at the thought of having a wank, or wondering if my wife would wank me, or even suck me off!
“Thank you Mistress, I will behave myself.”
“You will have to do everything I ask you to do, if not then you will have to wait for your security pass to come,” she said.
“Yes Mistress,” I thought I had been doing as I was told anyway, so nothing would be different.
“That’s good, Janet (her best friend) is coming round for a coffee this evening, and you are going to serve us,” she said with a smile.
There was a look of shock on my face, and I looked down at the dress I was wearing, as though she read my mind she said “It’s alright you will not have to have your dress on, unless you would like to be our maid, you never know it might be fun to have a maid to serve us.”
I immediately said “Please, no Mistress,” but as I was saying no, the image of me standing in front of them and curtseying came into my mind, which lead to my cock swelling, and my balls aching. God I desperately need a wank.
I know when Janet usually comes round I disappear upstairs, many times I am watching tranny porn on the computer, and sometimes I used to have Susan’s silky knickers and would wank myself, thinking of them downstairs, and me being so close, and the slight risk of being found adding to the excitement.
Sometimes I would go out with her hubby, Stuart, and we would go to the pub while ‘the girls’ had their natter.
If Janet saw me in a dress, she would surely tell Stuart, how would I be able to have a drink with him then?
“But how would I serve you, Janet would think it is odd,” I said.
“Don’t worry I have thought of that, all you will have to do is follow my lead. If you don’t want to do it though, that is fine, but you get no relief today,” was the answer she gave.
I was so desperate for a wank I said “OK I will do it,” what have I let myself in for!
I prepared the tea, as is my duty, and cleaned up, with lots of ‘Yes Mistress, and No Mistress’, as I did not want to do anything to screw up my chance of some relief.
Susan said “Time to get changed,” and led me upstairs.
She took out a sweat shirt and pair of jeans for me, at least she was not going to make me wear a dress.
I took my dress off, and began to unclip my bra.
“What are you doing?” she asked.
“Getting changed,” I replied.
“Your lingerie stays on.”
I suppose it was too much to hope for that I would be allowed to dress ‘normally’.
At least the baggy sweat shirt would easily hide my bra.
Then she held up two lipsticks, one bright red, one the subtle shade coral, “Hmmm, I wonder which one I should put on, and which one you will have on.”
I knew I had to take quick, manly, and decisive action, so I dropped to my knees and said “Please Mistress, can I have the coral lipstick.”
“Ok as you asked so nicely I will wear the other lipstick, but you will have to be a big girl someday and get your own make up, you can’t always borrow Mummy’s.”
I did not like where this statement led but said “Yes Mistress.”
Then she told me to sit at the dressing table, and instructed me about putting my lipstick on.
I do wish my cock was not throbbing so hard as my wife instructed me “That’s right, now press your lips together, as though you are trying to gently chew your lips, it helps to spread the lipstick. Now pout as though you are blowing yourself a kiss.” She then inspected me and was satisfied with the result, and touched up her lipstick.
I looked at my reflection, and the result on my lips was not dramatic, and I am sure Janet probably would not notice, but in my head I could imagine her going home and telling Stuart ‘when I went to Sue’s house, you will never guess but Les was wearing make up, and I am sure that he had a bra and stockings on.’
Stuart would probably think I an some kind if fairy, and it would not make it any better by saying ‘my wife made me do it.’
The doorbell went and my wife said, “Go and answer the door.”
I went downstairs and opened the door and let Janet in.
“Hi Les,” she said, she gave me no funny looks, so I assume that the fact that I was wearing lipstick was not obvious, and when we went into the living room my wife was there and they did the obligatory ‘air kisses’ as greeting, then my wife said to me “I know you have all that paperwork to do, and you said you needed the whole space of the dining room table to spread out what you need. Would it be ok if ‘us girls’ had our natter while you are working, and so we don’t disturb you too much, as we have to walk through the dining room to get to the kitchen, it might be easier if you got the coffees, is that ok.......................Les?”
Oh god I thought she was going to make me call her ‘Mistress’, in front of Janet, but as she called me Les, I can call her Sooze.
There was a feeling of relief as I said, “Sure Sooze, that’s a good idea.”
“What can I get you ladies,” I said putting on my best waiters voice.
They gave their ‘orders’, and I went into the kitchen to boil the kettle, and while that was boiling I took some random papers out of my brief case, and a calculator, to do my imaginary work.
I made the coffees and took them out to them, gave a mock bow, and said “There you are ladies, don’t hesitate to call if you require more service,” then retired to the dining room to start my imaginary work.
I had made myself a coffee, and to make it sound like I was working I kept tapping the calculator, knowing that my wife knew that I was not doing anything, but to Janet it would sound believable.
In my boredom, I was fiddling with my coffee cup, and was slowly turning it around, it was only on the third rotation that I suddenly realised what I was looking at, the rim of the coffee cup had lipstick prints on the rim of the cup, MY LIPSTICK PRINTS.
I looked up at the door, almost expecting Janet and my wife to be looking at the evidence on my cup, fortunately they were not there, but so afterwards I heard my wife's voice shout out “Les, when you have a moment, do you think you could bring in some biscuits?”
“Sure Sooze,” I shout back.
In some ways I was glad to do something, I got the biscuits from the kitchen, and took them into the living room, and again jokily said “There you go ladies, anything else I can do?”
They laughed and said no.
Just as I was about to leave the room my wife said “Actually, I fancy another coffee, how about you Janet?”
I am sure that she left it so late so I had to come into the room again.
“Same again?” I asked.
They both nodded, and as I picked up their cups, I noticed the lipstick stains on the rims of their cups, which made me think of my lipstick, then unfortunately it made me think of what I was wearing, and my cock came alive and tried to strain against it’s cage.
As my mind was thinking about lingerie, I could not help but thinking about what lingerie Janet was wearing, and I could just make out through her dress she had a bra, which was mainly white, but appeared the have different colours on, I assume they were pictures of flowers.
It was not an overly sexy bra, but my mind began to run riot, wishing I could have an hour alone and ‘uncaged’ to explore her underwear drawer. The ridiculous thing was that the chances are that what I was wearing at the moment was probably as sexy, if not sexier, than anything Janet might have. But the thought of dressing, and wanking, in lingerie that belongs to a woman, then seeing her and wondering if they are wearing the knickers you have previously wanked in is such a turn on.
These thoughts did not help the pain in my balls as they ached for relief.
I took the cups, and as I left the room I heard Janet say “I wish Stuart was as helpful as Les is.”
I hesitated once I was outside the door, to hear what my wife said, I do not know if she knew I was listening in but her reply was “Some men think that you need to be wearing knickers, to be useful around the house. Maybe you should put Stuart in some knickers and see if he magically starts being useful around the house.”
Both of them giggled at that thought, my mind though took that thought further and imagined myself and Stuart dressed fully in frilly French maids outfits, doing our chores while our wives are dressed sexily at the pub, on the pull. Unfortunately that thought made me even more excited, and leading to the usual pain.
As I took their coffees to them my wife said “Are you hard at it dear? Is there anything I could give you a hand with later?”
I knew what she was getting at so just played along “Something has come up, but it can wait until you have some time.”
I went back to the dining room, and continued with my non existent work until eventually Jane left and my wife called me into the room.
“See sissy, you could serve us. I must admit I almost decided not to give you the relief when I saw you ogling Janet’s tits,”
I didn’t know if it would make it better or worse to say I was actually ogling her bra, so kept quiet.
“But on the whole you did as you were told. So go upstairs and have a shower, and when you come into the bedroom, all you need to have on is your nightie, I think your knickers would be surplus to requirement.”
I have never been so happy at the thought of having a wank.
After my shower I went into the bedroom, just wearing my baby doll nightie as requested, and saw my wife on the bed, wearing her nightie, and rather unusually, wearing the thin latex gloves she usually wore when she was doing the gardening.
I wondered if in her mind she thought it would be more humiliating to wank me, but her hands not in contact with my cock, but to be honest, I did not care.
“Get on the bed on all fours,” she said.
I did as I was told and watched as she got something out of her drawer. I was a box, and it said KY Jelly, she opened the box and casually threw it on the floor, I knew I would be tidying it up later, and squeezed a few drops onto her gloves, and rubbed her hands together to lubricate them.
Then lifted the hem of my nightie, so my cock and balls were totally on display, then I felt a cold sensation as she squeezed a few drops of the jelly on my bum, I must admit I did gasp when I felt it.
Then she slowly pushed her hand down my bum cheeks, towards my balls, I felt like screaming ‘Take my cock out of my cage, and wank it,’ but was not in a situation to make any demands.
Just before her hands touched my balls, she reversed the direction her hands went, and was stroking back and forth, and I could feel my body responding.
Then her finger hovered over the entrance of my anus, and the it struck me that she was going to enter me, she has never done anything like that before, I was not even sure how I felt about her doing that.
The pressure increased and then I was aware she had entered me.
“Oh dear you are no longer a virgin,” she said.
It felt unusual but as she started to gently move her finger in and out I began to move my hips to go deeper.
Soon another finger entered me as well, and I could feel me being even more filled.
“There it is,” she said.
Then I suddenly felt my cock spurt, I looked worriedly between my legs, it felt like no orgasm I have ever had in my life. I was worried in case for some reason I had lost control of my bladder, and was relieved when I saw what was spurting from my cock was white, so was obviously semen. It even make me think of the joke.......’Why is semen white, and urine yellow...................so men know if they are cumming or going.’
I was definitely cumming, there was none of the feeling of pleasure, but I saw jet after jet of cum from my cock, after seven or eight jets, there were a few more dribbles and then it stopped.
I had cum, but for some reason I felt none of the pleasure, or feeling of release I would normally get, in fact I felt hornier. It must be like when a dog has been ‘seen to’ by the vet, he will still try to hump your leg, but doesn’t know why.
In my mind I was screaming ‘I was to fuck something, or have a good wank,’ but my cock was no longer straining to get out of it’s cage, so I doubt I would be able to do either of these activities.
My wife could see the puzzlement on my face and said “It is called milking, I read it on the internet, when you said about the pain you were in, I saw if there was anything I could do to help you.”
I really wanted to say was, a wank would have done, but what I said was “Thank you Mistress.”
She smiled and said “Do let me know if you want milking again, let’s hope it is not when Janet, or any of my other friends are around, just think having to ask to be milked in front of them. If you needed that maybe we could had a milking party, rather than ‘cheese and wine’ party, it would be a ‘milk and wine party.”
My mind was considering the humiliation of me having to stand in front of all her friends and begging to be milked, all of them laughing at me, and in my mind it was the most exciting thought, but at least my cock did not reveal how exciting I thought it would be, by getting hard.
She casually took the gloves off and threw them on the floor, then lay on her back, spread her legs, and said “Now you can really thank me for milking you.”
As I positioned my head between her legs, and started licking, I could feel my cock respond slightly because of what I was doing, but there was no pain, and my balls did not ache, I was even slightly worried that I would not be able to get a ‘proper’ erection, but I served my Mistress until she had at least three orgasms, and she told me to stop, so we could have some sleep.
All comments appreciated
I decide to go to the office early, then I don’t have to walk past Jane, as I park my car and get out I feel one of my suspenders come loose, there were a group of c***dren walking past so I could do nothing about it, but the building where I work is just across the street, and when I get in there I should be able to ‘adjust’ myself.
I swipe my security pass through the reader, and the doors come open, just my luck the security guard was at his desk, I nodded to him and he nodded back. I will have to wait until I am in my office to adjust myself.
I walk into the outer office, and at that moment, I felt the second suspender come loose, and I could feel the stocking begin to slide down my smooth shaven leg.
Almost safe, but as I look up I see Jane already at her desk, and she was looking directly at me.
There was no-one else in, why was Jane so early?
“Come and stand by my desk Miss Thorne,” she said.
Why was she talking to me like that, I am her boss, but I felt unable to do anything except say “yes Miss Jane.”
As I stood where directed, knowing my stocking was slipping lower, and wondering if it might fall down so low, it might show at the bottom of my trousers she said “I have had a nice conversation with your wife, Susan, or should I say your MISTRESS.”
My heart sank, I wondered if when I heard my wife speaking on the phone yesterday, she was speaking to Jane, maybe even telling her that I was standing in the corner of the bedroom as she spoke.
“She told me what a sissy you are, and you need to be humiliated. I want you to drop your trousers, and show me what she has had you wear today.”
I could myself blush, but knew I had to obey.
I stood in front of her knowing one stockings was attached, and the other was sagging around my knee.
She laughed “You are such a sissy, you can’t even dress yourself. This is how stockings should look.”
And with that she unzipped her dress, and it fell to the floor, and revealed that she was wearing a black leather corset, red knickers, black stockings.
As I said she is more of a Rubenesque kind of figure, and her tits were barely contained in the corset, and she pulled her suspender strap and ‘twanged’ it, “This is how a suspender should be attached.”
“Now pull your stockings up and attach your suspenders properly.”
She watched as I re-attached my suspenders to my stockings “From now on you will report to me every day for a ‘uniform inspection’, do you understand?”
“Yes Miss Jane,” why was my cock so hard being talked to by someone who I should be the boss of?
She opened one of the drawers of her desk and got out a pink leather dog collar, which already had a pink leash attached, and I saw on the collar it had the name ‘Fifi’ stitched on.
She put the collar around my neck, “Kneel down sissy.”
I did as ordered and she wrapped the leash around one of the handles of her desk.
“You normally have a cup of tea in the morning, don’t you sissy,” she said.
“Yes Miss Jane.”
“I can’t be bothered to make you a drink, but you can have my tea, I will want your tongue nice and wet for your duties.”
She then got her cup of tea, and poured it into the saucer, and placed it down in front of me, “Drink up sissy.”
I went to pick up the saucer and she said “No sissy, bend down and lap it up.”
I did not know how long before someone else came into the office and saw me in this humiliating position, so I started licking as ordered.
When I had finished Jane said “Thank me for letting you have my tea.”
“Thank you Miss Jane for letting me have your tea,” will this torture never end, but my cock is still trying to break free from it’s cage, and my balls were aching.
She turned her back on me so her bottom was directly in front of my face, then hooked her fingers in the waistband of her knickers and pulled then down. I so wanted to kiss her bottom, but did not dare do anything that I was not told to do.
Then she turned to face me, and she put her hand in front of her pussy as though being coy, and then slowly moved her hand away, and revealed a trimmed pubic bush, with only a thin strip of hair leading down to her pussy lips.
“Like my cut,” she said.
I nodded my head “Yes Miss Jane.”
She slapped my face “What do you mean just saying ‘yes Miss Jane’, I told you to lick my cunt, get on with it you sissy”
I closed my eyes and bent my head to her pussy and immediately started licking her pussy lips, after being married to Susan for so long and only having her pussy to lick, it felt so different, the taste and smell was different, even how her body reacted to my tongue was different.
I heard a voice behind me “We know who the sissy is in the office,” I recognised John’s voice. “Are your balls aching Les,” that was Peter. When did they get in, how much did they see? Both their statements were correct.
Jane shook my shoulder, I took it as an instruction to lick harder, so I licked harder and faster, she shook me harder and I opened my eyes.
I was in my bedroom, my wife standing over me with just a towel wrapped around her, smelling fresh from the shower “You slept through the alarm, I have had my shower so it is clear for you, you wouldn’t want to be late for work, you never know Miss Jane might have to punish you.”
The dream still felt so real, and my heart was pounding from what I had just imagined, and the thought of what the Jane in my dream would do to me made me feel weak, and I was glad when Susan put on her dressing gown and went downstairs as I did not feel capable of getting out of the bed at the moment.
It took a few minutes before I felt capable of getting up, but knew I had to face the day, and had my shower.
After having my shower, I went back into the bedroom, and as usual I saw my clothes laid out, the suit was normal, she had also laid out a pair of white satin knickers, a white lacy suspender belt, black stockings, and also a white lacy bra!
A bra, she could not be serious, but I know I cannot argue, I usually lose anyway, I got dressed and hoped that as it was white it would not show through my shirt.
When I was fully dressed I looked in the mirror, and there was no mistaking the outline of the bra under my shirt, I tried putting on the jacket of my suit, but there was no way of disguising, I WAS WEARING A BRA!
I thought if I went downstairs, dressed as she wanted, it would show I was following her orders, but showing wearing a bra was not practical, she might let me off.
I went downstairs, and she looked up as I came into the room, but passed no comment.
“Mistress,” I said.
“Yes.”
“You can see my bra.”
“Yes pretty isn’t it, I must admit when I saw it in the clothes that you had kept hidden, I thought it was pretty, I like the lacy cup of the bra, so feminine, and so revealing, I thought about getting something like that for myself.”
This conversation was not going the way I wanted.
“But you can see I am wearing a bra,” I tried stating the obvious.
“That is the problem we women have, wondering how much of our lingerie we can display to keep men interested, but not too much that looks tarty,” was her reply, “I don’t think it looks too tarty.”
“Yes but ‘I’ am wearing a bra,” stressing the word I.
She sighed and said “If it bothers you so much, you can wear a jumper as well.”
“Thank you Mistress,” I said as I sprinted upstairs.
As winter was approaching it was getting colder, and it is not as though I have never worn a jumper to work before.
I put a jumper on and was pleased that it was not totally obvious that I was wearing a bra, if you looked closely you could just about make out the straps, but if I kept my jacket on I am sure I will get away with it.
I have never been so glad to wear a jumper, I go downstairs and look at my wife and wonder if she is wearing stockings again today.
As though she is reading my mind she bent down to pick something up from the floor, and kept her legs straight which caused her skirt to ride up at the back, and I could see the tops of her stockings being pulled up by her suspenders.
She looked over her shoulder at me , and could see exactly what I was looking at. “Oops,” she said “I had better not do that when Rob is about.”
If only my cock was free I would have shown her exactly what I though about the display she was giving, either I would have fucked her, or at least wanked myself while looking at her.
As it was all I could do was to suffer more pain from my cock as it pushed against it’s prison bars, and my balls as they wanted to release the cum that they had been storing for the past few days.
As we left the house and the door closed, the knowledge that I could not go back in unless she let me crossed my mind.
As I parked up outside the office building, the dream I had popped into my mind, and I got out of my car, half expecting to feel a suspender strap come loose, and the feeling of relief as I walked to the office all the suspenders pulling against my stockings as they should.
I entered the building, and went into the outer office, and there was the normal hum of work going on.
As I looked at Jane at her desk I thought ‘I will say to her today about calling me Les again,’ but unfortunately the though of her standing over me wearing her leather corset came into my mind as well.
She looked up and said “Morning Miss Thorne.”
I heard myself say “Morning Miss Jane.”
FUCK, I will definitely say tomorrow about using my first name.
I went to walk past her desk and into my office when she said “Miss Thorne, I have something for you,” and opened a drawer in her desk, it was the same drawer that ,in my dream, she kept the pink dog collar and leash
I could feel my heart pounding, almost thinking she would be able to hear it.
Fortunately all she pulled out was the report she had been working on yesterday. “There are a few queries I need your help on.”
I stood next to her, and was aware that my stocking straps would be at her eye level height, and began to worry that she might glance and see the obvious sign of a suspender strap, or even accidently her shoulder my brush against my crotch, and feel the hard metal of my cage.
I did enjoy the view down her cleavage, and could even make out that the was wearing a white bra, and made me think that we were wearing the same colour bras.
Thoughts like that did not help my situation.
I could feel I was beginning to sweat, and I hope the answers I was giving her made sense, but all I wanted to do was get into my office.
When she finished with her queries, I took the report, and went into my office.
As I was about to sit down, and to be honest I did feel like collapsing into my chair, I remembered what happened yesterday when a suspender came loose, and sat down with more thought.
It was only when I was sat down I realised what I had done.
I had brushed my hands down the seat of my trousers, because I remembered being glad that my suspenders felt taut so they were firmly attached to my stockings. But that is the action a woman does as they sit down, they make sure their skirt if properly underneath then before they sit, it was such a feminine movement, maybe as I was wearing a dress all the time at home, my actions were becoming more feminine.
I can’t walk like a man, and I can’t even sit like a man, where is this going to end.
I look through the windows of my office at the other workers, but no-one was looking at me so I can only assume my actions were not noticed.
I buried myself in my paperwork, hoping the distraction will take my mind off my situation, it did partially work, but every breath I take makes me aware of the constriction of my chest that my bra causes, any slight movement of my legs, pulls on my suspenders, and I don’t know if it is just my imagination, but I am sure I can feel the lace trim of my knickers, gently tickling the tops of my legs.
My office phone goes off, and as I reach over to answer it, I feel my nipple rub against the lace cup of my bra, and the thought in my mind ‘do women’s nipples rub in their bras, or do their tits fill the cups of their bra so they are not rubbed?’
My mind was thinking of that as I was answering the call, so god knows what gibberish I was saying on the phone, all I was thinking about was going behind Jane, reaching my hands around her, holding her tits in each hand, each tit was more than a handful. Feeling her nipples and asking if her nipples rub against her bra.
It was later that morning that my phone went ‘Whit Whoo,’ and the message ‘Picture time sissy,’ was displayed.
As I walked past Jane I mumbled ‘just popping out,’ to which she just said ‘ok.’
As I went into the toilets, there was someone there, so I slipped into the cubical, and then found the extra problem of having a jumper on caused for showing my lingerie. I was trying to be quiet, people expect a certain amount movement, but what I was doing was unusual.
I could still hear the other person was there then it struck me, the camera makes a noise when you use it.
I was thinking, ‘have a piss, and bugger off,’ but the time was ticking away to the point I knew I had to do something, so tried to position the camera, and as I took the picture, coughed in the hope it hide the sound, then quickly sent the picture.
As the person was leaving my phone when ‘Whit Whoo,’ again, if the person heard or not I don’t know, but when I looked at the message it simply said ‘No Bra?’
When I took the picture it obviously did not show my bra, so I took another picture, making sure my bra was on display, and sent that.
I sat waiting, wondering when I could get dressed again, and it was almost a relief when I heard ‘Whit Whoo,’ and this time the message ready ‘Well done sissy.’
I got dressed, and fortunately there were no other incidents during the day, my wife did text me another time, but was able to take the picture with no problem.
I went home slightly later, as I did not want to be caught waiting outside my own house again, and I was relieved to see my wife’s car already parked.
Before I got out of my car I looked around to see no-one was about, and quickly rang the doorbell.
I began to sweat when the door was not immediately answered, and I was scared to ring again, in case it annoyed my wife, but was coming to the point when I had to do something, when I saw through the frosted glass of the front door, the shadowy shape of my wife coming.
She opened the door, just enough to peep round the door “Yes,” she said with a smile on her face.
“Please can I come in,” I asked.
“Ask me properly,” she replied.
I looked round, knowing the longer I left it the more likely of someone seeing me at my own doorstep.
“Please Mistress can I come in,” I was having to beg to come into my own house, but for some reason my cock loved it, I could feel it throbbing against it’s cage, and my ball aching in sympathy.
She opened the door and I quickly entered.
She closed the door behind me, “Now thank me for letting you in.”
“Thank you Mistress for letting me in,” I replied.
“On all fours, and kissing my feet,” she said.
“But Mistress, someone might see me through the glass.”
“Would you prefer the door open so they can see you clearly,” she said as she went to open the door.
I immediately dropped to my knees, started kissing her feet, and between kisses said “Thank you Mistress for letting me come in,” knowing the quicker she is satisfied with my humiliation, the faster she will let me into the house properly.
When she was satisfied with my humiliation, she said “I will have to think of a way of you coming in, without me being at you beck and call.”
In my mind I did think ‘if you give me my key back then you would not have to open the door for me,’ but I did not have the courage to say anything.
“I have laid your clothes out, so get dressed and then we will see what we are going to do this evening,” she said.
I went upstairs, and I was almost thinking of the tennis dress, and the shoes as my uniform.
When I had got dressed I went downstairs, and my wife pointed in front of her, so I stood where she indicated.
She kicked her shoes off and said “it does feel good to take the heels off, they do make you feel feminine, but can be uncomfortable.”
She made no indication that I could take my heels off so I just said “Yes Mistress,” as I picked her shoes up and tidied them away, then returned to stand in front of her.
“I have been thinking about what you said yesterday about you needing some ‘relief’, and I don’t want you in discomfort, so as long as you behave yourself this evening, I think I can help give you some relief.”
I have never felt so happy at the thought of having a wank, or wondering if my wife would wank me, or even suck me off!
“Thank you Mistress, I will behave myself.”
“You will have to do everything I ask you to do, if not then you will have to wait for your security pass to come,” she said.
“Yes Mistress,” I thought I had been doing as I was told anyway, so nothing would be different.
“That’s good, Janet (her best friend) is coming round for a coffee this evening, and you are going to serve us,” she said with a smile.
There was a look of shock on my face, and I looked down at the dress I was wearing, as though she read my mind she said “It’s alright you will not have to have your dress on, unless you would like to be our maid, you never know it might be fun to have a maid to serve us.”
I immediately said “Please, no Mistress,” but as I was saying no, the image of me standing in front of them and curtseying came into my mind, which lead to my cock swelling, and my balls aching. God I desperately need a wank.
I know when Janet usually comes round I disappear upstairs, many times I am watching tranny porn on the computer, and sometimes I used to have Susan’s silky knickers and would wank myself, thinking of them downstairs, and me being so close, and the slight risk of being found adding to the excitement.
Sometimes I would go out with her hubby, Stuart, and we would go to the pub while ‘the girls’ had their natter.
If Janet saw me in a dress, she would surely tell Stuart, how would I be able to have a drink with him then?
“But how would I serve you, Janet would think it is odd,” I said.
“Don’t worry I have thought of that, all you will have to do is follow my lead. If you don’t want to do it though, that is fine, but you get no relief today,” was the answer she gave.
I was so desperate for a wank I said “OK I will do it,” what have I let myself in for!
I prepared the tea, as is my duty, and cleaned up, with lots of ‘Yes Mistress, and No Mistress’, as I did not want to do anything to screw up my chance of some relief.
Susan said “Time to get changed,” and led me upstairs.
She took out a sweat shirt and pair of jeans for me, at least she was not going to make me wear a dress.
I took my dress off, and began to unclip my bra.
“What are you doing?” she asked.
“Getting changed,” I replied.
“Your lingerie stays on.”
I suppose it was too much to hope for that I would be allowed to dress ‘normally’.
At least the baggy sweat shirt would easily hide my bra.
Then she held up two lipsticks, one bright red, one the subtle shade coral, “Hmmm, I wonder which one I should put on, and which one you will have on.”
I knew I had to take quick, manly, and decisive action, so I dropped to my knees and said “Please Mistress, can I have the coral lipstick.”
“Ok as you asked so nicely I will wear the other lipstick, but you will have to be a big girl someday and get your own make up, you can’t always borrow Mummy’s.”
I did not like where this statement led but said “Yes Mistress.”
Then she told me to sit at the dressing table, and instructed me about putting my lipstick on.
I do wish my cock was not throbbing so hard as my wife instructed me “That’s right, now press your lips together, as though you are trying to gently chew your lips, it helps to spread the lipstick. Now pout as though you are blowing yourself a kiss.” She then inspected me and was satisfied with the result, and touched up her lipstick.
I looked at my reflection, and the result on my lips was not dramatic, and I am sure Janet probably would not notice, but in my head I could imagine her going home and telling Stuart ‘when I went to Sue’s house, you will never guess but Les was wearing make up, and I am sure that he had a bra and stockings on.’
Stuart would probably think I an some kind if fairy, and it would not make it any better by saying ‘my wife made me do it.’
The doorbell went and my wife said, “Go and answer the door.”
I went downstairs and opened the door and let Janet in.
“Hi Les,” she said, she gave me no funny looks, so I assume that the fact that I was wearing lipstick was not obvious, and when we went into the living room my wife was there and they did the obligatory ‘air kisses’ as greeting, then my wife said to me “I know you have all that paperwork to do, and you said you needed the whole space of the dining room table to spread out what you need. Would it be ok if ‘us girls’ had our natter while you are working, and so we don’t disturb you too much, as we have to walk through the dining room to get to the kitchen, it might be easier if you got the coffees, is that ok.......................Les?”
Oh god I thought she was going to make me call her ‘Mistress’, in front of Janet, but as she called me Les, I can call her Sooze.
There was a feeling of relief as I said, “Sure Sooze, that’s a good idea.”
“What can I get you ladies,” I said putting on my best waiters voice.
They gave their ‘orders’, and I went into the kitchen to boil the kettle, and while that was boiling I took some random papers out of my brief case, and a calculator, to do my imaginary work.
I made the coffees and took them out to them, gave a mock bow, and said “There you are ladies, don’t hesitate to call if you require more service,” then retired to the dining room to start my imaginary work.
I had made myself a coffee, and to make it sound like I was working I kept tapping the calculator, knowing that my wife knew that I was not doing anything, but to Janet it would sound believable.
In my boredom, I was fiddling with my coffee cup, and was slowly turning it around, it was only on the third rotation that I suddenly realised what I was looking at, the rim of the coffee cup had lipstick prints on the rim of the cup, MY LIPSTICK PRINTS.
I looked up at the door, almost expecting Janet and my wife to be looking at the evidence on my cup, fortunately they were not there, but so afterwards I heard my wife's voice shout out “Les, when you have a moment, do you think you could bring in some biscuits?”
“Sure Sooze,” I shout back.
In some ways I was glad to do something, I got the biscuits from the kitchen, and took them into the living room, and again jokily said “There you go ladies, anything else I can do?”
They laughed and said no.
Just as I was about to leave the room my wife said “Actually, I fancy another coffee, how about you Janet?”
I am sure that she left it so late so I had to come into the room again.
“Same again?” I asked.
They both nodded, and as I picked up their cups, I noticed the lipstick stains on the rims of their cups, which made me think of my lipstick, then unfortunately it made me think of what I was wearing, and my cock came alive and tried to strain against it’s cage.
As my mind was thinking about lingerie, I could not help but thinking about what lingerie Janet was wearing, and I could just make out through her dress she had a bra, which was mainly white, but appeared the have different colours on, I assume they were pictures of flowers.
It was not an overly sexy bra, but my mind began to run riot, wishing I could have an hour alone and ‘uncaged’ to explore her underwear drawer. The ridiculous thing was that the chances are that what I was wearing at the moment was probably as sexy, if not sexier, than anything Janet might have. But the thought of dressing, and wanking, in lingerie that belongs to a woman, then seeing her and wondering if they are wearing the knickers you have previously wanked in is such a turn on.
These thoughts did not help the pain in my balls as they ached for relief.
I took the cups, and as I left the room I heard Janet say “I wish Stuart was as helpful as Les is.”
I hesitated once I was outside the door, to hear what my wife said, I do not know if she knew I was listening in but her reply was “Some men think that you need to be wearing knickers, to be useful around the house. Maybe you should put Stuart in some knickers and see if he magically starts being useful around the house.”
Both of them giggled at that thought, my mind though took that thought further and imagined myself and Stuart dressed fully in frilly French maids outfits, doing our chores while our wives are dressed sexily at the pub, on the pull. Unfortunately that thought made me even more excited, and leading to the usual pain.
As I took their coffees to them my wife said “Are you hard at it dear? Is there anything I could give you a hand with later?”
I knew what she was getting at so just played along “Something has come up, but it can wait until you have some time.”
I went back to the dining room, and continued with my non existent work until eventually Jane left and my wife called me into the room.
“See sissy, you could serve us. I must admit I almost decided not to give you the relief when I saw you ogling Janet’s tits,”
I didn’t know if it would make it better or worse to say I was actually ogling her bra, so kept quiet.
“But on the whole you did as you were told. So go upstairs and have a shower, and when you come into the bedroom, all you need to have on is your nightie, I think your knickers would be surplus to requirement.”
I have never been so happy at the thought of having a wank.
After my shower I went into the bedroom, just wearing my baby doll nightie as requested, and saw my wife on the bed, wearing her nightie, and rather unusually, wearing the thin latex gloves she usually wore when she was doing the gardening.
I wondered if in her mind she thought it would be more humiliating to wank me, but her hands not in contact with my cock, but to be honest, I did not care.
“Get on the bed on all fours,” she said.
I did as I was told and watched as she got something out of her drawer. I was a box, and it said KY Jelly, she opened the box and casually threw it on the floor, I knew I would be tidying it up later, and squeezed a few drops onto her gloves, and rubbed her hands together to lubricate them.
Then lifted the hem of my nightie, so my cock and balls were totally on display, then I felt a cold sensation as she squeezed a few drops of the jelly on my bum, I must admit I did gasp when I felt it.
Then she slowly pushed her hand down my bum cheeks, towards my balls, I felt like screaming ‘Take my cock out of my cage, and wank it,’ but was not in a situation to make any demands.
Just before her hands touched my balls, she reversed the direction her hands went, and was stroking back and forth, and I could feel my body responding.
Then her finger hovered over the entrance of my anus, and the it struck me that she was going to enter me, she has never done anything like that before, I was not even sure how I felt about her doing that.
The pressure increased and then I was aware she had entered me.
“Oh dear you are no longer a virgin,” she said.
It felt unusual but as she started to gently move her finger in and out I began to move my hips to go deeper.
Soon another finger entered me as well, and I could feel me being even more filled.
“There it is,” she said.
Then I suddenly felt my cock spurt, I looked worriedly between my legs, it felt like no orgasm I have ever had in my life. I was worried in case for some reason I had lost control of my bladder, and was relieved when I saw what was spurting from my cock was white, so was obviously semen. It even make me think of the joke.......’Why is semen white, and urine yellow...................so men know if they are cumming or going.’
I was definitely cumming, there was none of the feeling of pleasure, but I saw jet after jet of cum from my cock, after seven or eight jets, there were a few more dribbles and then it stopped.
I had cum, but for some reason I felt none of the pleasure, or feeling of release I would normally get, in fact I felt hornier. It must be like when a dog has been ‘seen to’ by the vet, he will still try to hump your leg, but doesn’t know why.
In my mind I was screaming ‘I was to fuck something, or have a good wank,’ but my cock was no longer straining to get out of it’s cage, so I doubt I would be able to do either of these activities.
My wife could see the puzzlement on my face and said “It is called milking, I read it on the internet, when you said about the pain you were in, I saw if there was anything I could do to help you.”
I really wanted to say was, a wank would have done, but what I said was “Thank you Mistress.”
She smiled and said “Do let me know if you want milking again, let’s hope it is not when Janet, or any of my other friends are around, just think having to ask to be milked in front of them. If you needed that maybe we could had a milking party, rather than ‘cheese and wine’ party, it would be a ‘milk and wine party.”
My mind was considering the humiliation of me having to stand in front of all her friends and begging to be milked, all of them laughing at me, and in my mind it was the most exciting thought, but at least my cock did not reveal how exciting I thought it would be, by getting hard.
She casually took the gloves off and threw them on the floor, then lay on her back, spread her legs, and said “Now you can really thank me for milking you.”
As I positioned my head between her legs, and started licking, I could feel my cock respond slightly because of what I was doing, but there was no pain, and my balls did not ache, I was even slightly worried that I would not be able to get a ‘proper’ erection, but I served my Mistress until she had at least three orgasms, and she told me to stop, so we could have some sleep.
All comments appreciated
2 lata/lat temu
