Old 01-19-2021, 09:31 AM   #1
dwedgie
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Default Caught out

I had recently moved into a new flat on my own, for the last 5 years I ve worn womens panties at home, only wearing boxers when out. It was a chilly saturday morning in November and I had a few jobs to do.
I was wearing a pair of blue lacy boy shorts that I just about fitted into , with an almost thong back to them leaving my cheeks exposed , became up above my hips so sat above my Jean's I wore over them . Having done all the bits inside I went to scrub the stairs as they were mossey and slippery. I was on the last stair when my new nieghbour came up behind me, we said hello , I had spoken a couple of time ps to her before, as she went to walk away , she whispered in my ear " nice panties , unless you want the rest of the nieghbour knowing , be at mine in 1 hr , wearing what you have on now ". And walked off, blowing a kiss as she disappeared round the corner.
1hr later I'm knocking on her door, she answers it in Jean's and t shirt " Ah good, you came, come in " she said smiling.
I walked in taking off my shoes as I entered , after shutting g the door , she said " that's not all you ll be taking off, strip to you panties"
" What, really? " I gasped
" Yes, you like panties , well you can either keep your secret and strip or everyone will know"
I slowly , nervously removed my t shirt , socks and Jean's til I stood there In my panties with a semi erection .
" not bad , but only panties, and they do not really suit you " with that she dissappeared into a room and returned with some clothes, " put these on , now"
She handed me a red and black set of bra, thong , suspenders and black stockings .
I removed my panties and dressed in the cloths I was given with out protest.
" that's better , i knew you were a sissy when i first met you " she said , then given my bum a short sharp spank , she ushered me into a room, i was shocked and speechless , the walls were lined with " toys" .
" You have choice , go home now in what you are wearing, or be my little sissy and you can go home as normal later, if you stay no one finds out, if you go, well I can not promise a thing "
By now I had a full erection, " I'll stay " I replied.
With that she removed her Jeans and top , revealing a one piece PVC bodysuit and red stockings. "Sissies may not talk " she said reaching for a ball gag and roughly putting it on me, she was stronger then me and I was to shocked to fight it .
Next she cuffed my hands together and bent me over a large wooden box. Taking a riding crop off the wall a holding it in front of my face, " meet my sissie trainer , 10 per cheek for being a mix ute late" she said, what I thought I was not late but was unable to say.
As she walked behind d me she dragged it over my back, It felt sensual , then alternating cheeks she slap me with it , not to hard , but harder each time, after 5 each she said ," well done , no flinching, however they get harder now, and in case you flinch I ll have to tie you to the box" with that I felt straps go round my ankles and my already cuffed wrists were attached to the box, I was trapped, she ran the crop over me, gently tapping my balls, then WHACK, across my left cheek, I tried to move and cry out but could not, then she continued harder and harder, when she finished my arse was on fire.
" You took that better then I thought sissy , your not as pathetic as I thought " she said as she walked out of the room and left me there!
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Old 01-19-2021, 12:53 PM   #2
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After a while, she returned , my erection had gone and pain subsided, I knew I'd been spanked but it no longer hurt as much . She knelt in front of me , " well done , you have passed the first test, if you behave when I release you I ll remove the gag, if you do as I say it won't hurt as much , you may enjoy it , you did earlier!"
I am released from the box, I stay bent over it awaiting instructions.
" Stand up , what are you waiting for" she say sharply.
I stand up and the gag is removed , as I go to ask a question , why, before I can say a word she says" I did not give you permission to talk , hands in the air"
I raise my still cuffed hands and feel her attach them to something , then she walks to the wall and turns a handle ' a whinch , I feel my hands being pulled up, my feet are flat on the floor , but I am being stretched. She then takes something from the wall, a flogger, she walks back to me and whispers in my ear" this can bring pleasure and pain " as she runs it over me and gently whips my back . I start to get erect and she notices, " to much pleasure " she giggles as she whips my back, not hard , but so I know it, unfortunately I continue to grow, 2 whips , hard this time. I Yelp!
" do not make a noise , as if it's not bad enough you have an erection "
" sorry miss " I rep.y
" I told you not to make a noise sissy. " she hissed, she seemed angry ,.whack whack whack each cheek and across my back , harder this time! I felt her slide her fingers into the sides of the thong and pull it down and tells me to step out of it. She disappears for a few minutes, then returns and cups my balls from behind , my erection that had started to subside sprung up again .
She walked round me and taking my by surprise knelt in front of me , putting my hard cock in her mouth, gently biting down on my helmet. I groaned in pleasure, she ran her lips up and down my shaft , taking the full length.
Suddenly she grabs my balls, hard. " enough pleasure for now " she says . I try not to make a noise , but as I was shocked I let out a gasp and Yelp, as I do her grip tightens! Shhhh she says .
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Old 01-19-2021, 01:51 PM   #3
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I like your story. I hope you keep it going. I was actually caught once, nothing like this happened though
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Old 01-20-2021, 08:28 AM   #4
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As she stands up, she reduces the grip she has on my balls, standing face to face , with her holding my balls , my cock hard , she looks down at it and says " it appears my sissy boy likes pain, it looks like it brings you pleasure. " with that she releases her grip entirely. I let out a sigh of relief , to which she says " I'm not done yet, but I think you will enjoy what's coming"
I ve learnt not to make a noise, as it brings pain, but also pleasure!
She walks round me , stroking my body with her hands , before unwinding the winch, leaving it attached but my hands now able to be in a normal ish position. She continues to stroke my body, suddenly she concentrates on rubbing my still sore bum cheeks, moving closer to my anus.
She stops and unhooks my hands before releasing the cuffs , instead fastening a collar round my neck, attached to it was a lead . Looking me over , she says" you have done well, one last thing then as long as you do not make a noise , you can go home, however , if you make a noise , well I think you know theres a punishment "
I nod to show I understand .
She points to the corner of the room , it's barely lit , and says " get on all fours facing the corner " as I go to the corner and get onto my hands and knees I notice a ring in the floor, before I know what's happened the lead is hooked to it.
" off you knees , feet on the floor, feet apart " she says . I do as told , with my feet apart I feel more vulnerable then before.
" just to remind you who is in control " she says as she spanks my bum with the crop, thwack thwack thwack, not to hard , but enough to make me jump.
I hear a noise, metallic , like buckles, I look between my legs and see her back to me, her pert cheeks showing either side of the thong back on her outfit, I see she is buckling something up, as she turns round I see it's a strap on, now I have never taken anything anally before , seeing my look of shock , she says, " don't worry, this is my smallest one, ideal for breaking you in , it won't hurt to much!"
She stands behind me , putting lube on my anus, gently working her her finger in me , it feels odd and cold , after working my anus with her fi ber for a minute or so, she removes it, gently placing the tip of the strap on into my anus.
" all sissies deserve to have a good fucking, here's yours ." She says gently but forcefully pushing into me, as I start to groan , she eases off a bit and says " remember , punishment !" As she suddenly pushes harder and puts the full length in me ! I let out a stifled scream as she pumps my arse slowly but with force!
After a bout a minute she speeds up a bit , I groan in joy, i feel my cock getting bigger, she's using the entire length , the end almost coming out, it hurts a bit , but I also feel in ecstasy, again she speeds up , I groan again . I feel my balls and penis pumping , oh shit I though , I m going to cum!
I can hold it no more , I come , with a massive groan shooting several big streams of cum on the floor, no sooner have I come she pulls out of me, I fall to the floor!
" your final task is to lick up your cum sissy, then , when I m happy it's all gone , we will sort out a punishment ! "
I do as told , licking all the cum from the wooden floor.
By now my penis was drooping, she unhooks me from the floor, makes me stand up and reattached the hook to the wall.
Looking at my penis , she says quietly, " your punishment, is not to cum for 2 days, to make sure you don't, I have this"
She produces a cage, it's made from thin metal bars , is hinged underneath and has a small padlock on top.
Quickly she snaps it round my cock and balls and locks it.
I gasp in shock , and ask " what, why !"
Her reply , " I need to punish my new sissy, I also need to make sure you obey me, come back in 2 days , at 9pm and I ll let you come, you can try to free yourself, but it's a snug fit , and It will probably hurt! , now put your clothes on and i ll let you out" she releases the collar, i take her clothes off and redress , as I'm almost ready she reappears in Jean's and t shirt. " I ll drop off something for you to wear when you come back in 2 days , in case you think you can get it off and not return, there are cameras that have filmed it all and I could always put it on social media! "
" please no" I beg " I ll be here and do as you tell me " I reply.
" your are a good sissy , but need more training, now go home and I'll see you later " she says as she opens the door and pushes me out. The door shuts behind me and I slowly walk home.
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Old 01-21-2021, 09:49 AM   #5
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I walk home, concious of the cage around my cock and balls, it is almost midnight, I had been gone for 6 hours. Once I'm home I go to the bath room and strip, I look at the cage in the hope i ll see a way to remove it, there is none, I m stuck.
I realise I need a pee, I have to pee thru the cage , instead of the usual stream it now hits the cage bars and goes every where , I clean up , have a shower and go to bed pondering my situation .
I wake the next morning with a pain in my cock and balls, I look down to see I have an erection , my cock is pushing on the bars , due to its extended length is pulling on my balls and theres nothing I can do. After a while the urge goes, i get up and go about my normal day , aware of the cage causing slight discomfort.
The next day I return from work and shopping , it's been an uncomfortable day , I had to do my best to rearrange things down there a few times , but nothing helped. On my doorstep is a plain parcel, trainer box sized, I was not expecting a delivery . I placed it on the table and put the shopping away .
I opened the parcel , a note on top of the contents said only "6pm"
I look in the box , on top is a pair of plain black flat ladies shoes , they are my size, I remove them and the next item is a pink Lacey pair of boy shorts, matching stockings, suspender belt and bra. They are all in my size and of good quality. Under these is a black short sleeved mini dress , it has a zip fastening up the back , but is plain , there is also a white maids apron and hat. Then I see the note at the bottom, it reads
" all my sissies must be able to attend to my needs around the house, as I know you are obedient you will now progress to your next stage of training .put your new uniform on and come to mine wearing just that, no coat ! Knock on the door and enter , you will see a chair, sit on it and await further instructions. Reme ber , you are my sissy, I have something you need"
I look at the clock , its 5.20, I get changed and look in the mirror , the dress barely covers my cheeks , it's a snug fit but not uncomfortable. I head out of my flat and walk quickly the short trip to hers in the hope that no one sees, thankfully its quiet and I do not see anyone, I arrive and knock before entering. There in the middle of the hall is a small wooden chair , the seat is lower then normal , the back straight , I sit on it ,its not at all comfortable, I wait for my next instructions .
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Old 01-23-2021, 11:15 AM   #6
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Suddenly I hear her footsteps behind d me . " stand up you worthless sissy " she commands , still behind me, I immediately stand up, she walks round me , examining me from top to toe.
" feet apart" she commands , as she lifts the bottom of my dress, she runs her hands over my bum cheeks , then round to my balls and caged cock, that is getting hard.
" Hmmm I think it's time to release this , drop those panties " she says
I drop my panties to my knees . " that's far enough " she says as she walks over and removes my cage. " pull your panties up " she says.
.
I do as I'm told, no sooner have I done so , she says, " I have inspected how you are wearing your uniform , and it is satisfactory, now you will go into the room on your right and clean the floor, everything you need is in the bucket" I hesitate, thwack, I feel a sudden sharp pain across my cheeks as she whips me with a crop. " now sissy , or next time it will be harder" she says
" sssorry " I stammer, with that she grabs me by the back of my dress , pulling me back and speaking into my ear , says " I do not recall saying you can speak, now clean!"
I open the door and walk into a dimly lit room , it was about 10ft x 10ft bare brick walls and wooden floor . In the corner is a bucket with warm soapy water and a scrubbing brush in. The door closed behind me and I hear a jangle of keys and click as the door locked. " i ll be back in 10 minutes and that floor better be clean " she says.
I get on my knees and scrub the floor, it's not actually dirty, by the time I'm do e the water is still almost clear .
I wait a few minute then hear the door unlock , then the whole room lights up , there are spot lights in the corners of the room, I'm blinded .
The door opens, " good " she says ' " but look at the state of you" she says in an annoyed voice . I look down and see my stockings a wet and one ladders.
" pass me the bucket " she says , I do so . She throws the contents over me " if you don't look after your uniform , you may as well be totally covered in water" she says , i was shocked , i gasped . I was shocked, the dress , my bra panties a d stockings clutching g to me.
" come this way " she led me out of the room , still dripping and into the room I was in 2 days ago.
She led me to the middle of the room . " hands above your head, spread apart and feet apart " she commands. As i do as I'm told, a hood is put over my head and I fell a slight tightness around my neck and here a metallic noise as what I assume is a buckle is done up. Next I head a chain , then feel the steel of a cuff round each wrist and ankle.
Chink chink chink I hear chains moving , then feel pulling o my wrists and ankles as the chains seem to be getting shorter and stretching me. The chains are tight, stretching me, but not getting tighter. I moan as it's not comfort able . " quiet, you really are trying my patience now" she says.
I feel my dress being moved , then suddenly the sound of material being cut, I feel cool air on my back and realize she has cut the back of my dress open, then I feel her cut the back of each sleeve, the dress falls to the ground, in left In only shoes, stockings, panties , bra and suspender belt , oh and hood .

Last edited by dwedgie; 01-23-2021 at 11:33 AM.
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Old 01-23-2021, 11:29 AM   #7
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I realize I had not put a description of her clothing , she wore thigh high black shiny boots with a high heel, shiny black skin tight shorts, leaving her cheeks uncovered, matching
bustier / corset with 4 buckles up the front, matching mask , which covered her head, with buckles up the back and holes for mouth , nose, eyes and ears.
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Old 01-24-2021, 06:06 PM   #8
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please keep going!
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Old 01-25-2021, 02:49 PM   #9
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Will add more soon , as and when time / workload permits . may be a few days as now out of covid self isolation .
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Old 02-03-2021, 07:34 AM   #10
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Yay!!! Totally understand if you've been busy. I just love this story
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Old 02-04-2021, 03:29 PM   #11
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She left me , helplessly stuck for what seemed to be hours, but was probably about 10 minutes. Then suddenly , without a noise I felt something squeeze my balls, slowly tightening the grip, i groan as the pain starts to increase, as I groan the grip Increases sharply before releasing to its previous level , I do my best to stifle it but let out a scream, again the pressure increases, and releases , I scream and try to bend over but am trapped , eyes watering up in pain. Suddenly the grip releases, still in pain I feel a hand grip my flaccid penis, gently rubbing it, despite still having a bit of pain in my balks , i feel my penis getting harder, til I'm fully erect, the rubbing stops and my panties pulled down at the front, leaving my cock and balls exposed.
Thwack, a searing pain across my bum cheeks , thwack , thwack , thwack. Each time I cry out in pain, then suddenly nothing . I'm left again .
Then feel the tension on my arms and legs release.
"Remove the rest of your clothes when I have removed your restraints " she commands. Once my restraints are off , I do as I'm told, I'm now stood naked with a hood on. I feel the buckle on the hood release and the hood is removed .
I struggle to focus as there is a spot light pointing at me, I can make out 2 figures , her and another person, after a few seconds I realise the other person is a Male, blind folded and gagged tied hands above his head and attached to a hook . Totally naked , he looked to be about 25, mousy hair , clean shaven face , fair skin , no bodily hair , armpits, arms , chest , legs and pubic area totally bald. His penis was erect, about 7 inches, pointing slightly upwards.
" You are not my only toy she says, but even toys deserve some pleasure she says, on your knees and suck that cock you worthless sissy " she says .
I do ad I'm told, knowing if not there will be worse.
I felt odd , I had never sucked another guy before, his skin was soft, tasted slightly salty, smelt of soap. I was running my lips up and down his cock, taking the full length, e berti e his head hit my throat I wanted to gag.
" faster, we have not got all day" she commanded
I speed up, I feel his body tense up, his cock grows bigger, sensing he is on the edge, i speed up more, suddenly i feel his cock exp,ode in my mouth one steam on my tongue, its salty and warm, I stop taking g the full length , but continue to concentrate on the head.
"Do not swallow hold it all in your mouth " she commands.
4 more streams of cum in my mouth.
" stop" she orders. " come over here and let me see that cum " she says
I stand up and walk to her .
" open your mouth" she looks in my mouth, " good, now swallow all of it "
I swallow and feel it trickle down my throat.
" with pleasure comes pain , you had the pain, he had the pleasure" she says to me. " now go in that room and get dressed " she says pointing to a door in front of me.
I enter the room , it's no bigger then a shop changing room, hanging up is an out fit , ladies sports wear. A sports bra, matching thong, both in pink, a pale blue t shirt, navy blue leggings, white ankle socks and trainers. I get dressed , it all fits perfectly , I look in the mirror and except for my penis bulge almost pass as a girl.
I leave the room to fi d her alone.
" go home, I'll let you know when to come back " she says.
I leave and head home, Its dark, I pass a young couple on my way and notice the girl point at me and see her whisper to her partner , and giggle . I get home and realize I had been gone 4 hrs .
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Old 02-10-2021, 01:37 PM   #12
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I decided I should put the clothes I am made to wear in a separate drawer.
A couple of days go by , I have heard nothing. I decided that instead of wearing my normal shorts and t shirt for my exercise, today I will wear my girlie outfit. I strip naked and open the drawer , I take out the sports bra and put it on backwards so I an fasten the back then twist it round and put my arms thru the straps, next is the thong, I sit down and slid it up my legs to the top of my thighs, standing up and pulling it up the last bit ensuring g that my valls and semi erect cock are tucked in . Next I put the leggings on , in the same way as the thong, they fit snuggly, showing my bulge. Next I put the top on, again its snug. Followed by socks and trainers. I add a baseball cap and sunglasses to hid my more masculine face.
I look in the mirror and can see my bulge is obvious, I grab a thin training jacket and tie it round my waste to help hide it. I go for a jog round the local park, about 2 miles,inc the trip there and back, my normal route.
About half way round I am aware the the thong is riding up, I do my best to adjust it on the move, with little success. I pass a few other walkers and joggers and a knowledge them all with a nod.
When i get home i head to the bathroom for a shower , i strip to the bra and thong, i look in the mirror and see my semi erect cock is still in the thong, but my balls are hanging out. Wondering what my mistress has planned for me and when i get an erection . My hand strokes my cock over the thong it gets harder, my hand moves into the thong and I grip my shaft and masturbate , faster and faster , then slowing down , then faster , full long strokes, it's not long before i feel the pressure building , then , I cum , continueing to wank 4 more streams of cum , all shoot into the thong. I take the bra off , followed by thong, cum soaked into it and dripping off my cock, I turn the shower on and step into it , washing myself.
After my shower I dry off , wrap a towel round me and take my sports wear and put it in the washing machine.
I get dressed into my normal clothes and carry on with my day.
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Old 02-15-2021, 02:40 PM   #13
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A couple more days pass , and still I have heard nothing. Is she fed up with me? Did I do something wrong ?
Well I need not wonder any more as It was a Saturday and i was laying in , there was a knock at the door , i was not expecting anyone so left it, then there was a harder knock , so i answered it as it sounded urgent, dress only in trunks and t shirt I opened the door partly and saw her standing there.
" do I have to stand on the doorstep all day ? " she asked
" sorry, no ,come in " I said as i opened the door , she marched in , i shut the door, she was wearing black boots, tight faded Jean's, and a sweat shirt. Throwing a bag at me she instructed me to strip and put on the contents of the bag , here and now.

Opening the bag i see it's a black PVC outfit.
" stop looking, strip , then put it on " She said in a angry voice.
I stripped naked and took the first item out of the bag, it was a tight glossy black dress, I pull it on struggling to squeeze into it, she walks round me, zip , I feel it get tighter as she does the zip up on the back.
Next item in the bag was a pair of thigh high boots, I take then out and put them on , pulling the zips up the side , feeling them become tight on my legs.
" hmm , suits you, now go into that corner, and face the wall" she points to the corner. I do as she instructs. As I get to the corner she walks up behind me and puts a blind fold on me. No peeking she says as she slaps my bum.
I hear a zip, and the soft clump of what i assume are clothes hitting the floor.
" turn round and take 2 steps forward"
I do as told, " fleet apart "
I struggle to spread my legs.
Suddenly out of nowhere she grabs my balls, gently , but firmly , her fingernails just dighing into the skin. My cock gets hard, and her hand moves to it , gently rubbing it. After a few strokes , she stops , after what seemed ages she said " hands behind your back" as I put them behind my back, I feel cold metal round my wrists, click , click as she cuffs my wrists together.
Then the blind fold is removed , on the floor in front of me I see the clothes she had on . Then she appears from behind me, wearing a Lacey black bra and matching g string, she has a perfect body , slightly tanned, my cock twitches and grows more.
" like what you see, it's your turn for some pleasure " she says as she turns round and bends over in front of me , showing her hot bum to me. She stands upright and turns to face me , as she kneels down in front of me she says" I want you to give me your cum"
She places her lips round my shaft, working up and down, suddenly she uses her tongue on the head of my cock.
Fuck she knows what she's doing I thought. I did not know how long I could hold on for til I cum, she was working my cock, I could feel it would be soon. A few more full length socks was all it took, my head was just in her mouth , I shot my load, pumping my cum into her mouth she continued to play with my head using her tongue. She stopped , still kneeling and opened her mouth to show me my cum, then closing g her mouth she swallowed.
" mmm good boy , be at mine tomorrow morning , 10 am, wearing the clothing that will be in a box on the doorstep tomorrow morning " she said as she stood up and took off my handcuffs, " and bring those items and the sports clothing with you " she said as she got dressed and walked out the door! I removed the cloths and had a shower before dressing . I put on my own clothes , straight cut Jean's, t shirt , sweat shirt, but decided I should wear something girly today , so put on a pair of lace topped white socks and a pair of pink cheeky boy shorts.
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Old 03-04-2021, 03:46 PM   #14
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Can't wait for you to continue the story! Just love it
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Old 03-10-2021, 02:16 PM   #15
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The next day I get woken by a knock at the door, its 6 am . I ignore the knock, about 30 seconds later , a louder knock , I get up , grab my dressing gown and put it on ( I sleep nude) I get to the door and open it slightly, there stands a girl, shorter then me, about 5 ft 6in slim build , slight tan , mousey hair, black dress mid way down thighs , sleeveless, black tights, black strappy medium heel shoes. In front of her on the floor is a box.
" you are to wear the cloths supplied in the box, put the items you are returning in the box, your services are required all day, til tomorrow morning. Do not be late ! " she says in a hushed but deep voice , at this point I realise she is a he! As soon as he / she had finished talking they turned round and walked away.
I pick the box up and take it indoors, placing it on my kitchen table i carefully open it, inside is a note.
Sissy

Today you will accompany me on a trip out, we will do some shopping g , have a meal , a bit of sight seeing and end up at a party. You must be a convincing girl, all you need is here. Note , girls have no body hair , you will not have a y either.

Your Mistress

I look in the box, the fist item I see is a long dark wig, I place it on the table, next is a bag containing make up and a razor with shaving gel. Next is a pair of medium heel navy shoes, then navy blue dress, similar in style to the delivery guys one, a mid blue bra, with white edging and pre padded with matching thong, black tights and a casual black jacket.

Being as I've never shaved this much I start to think what if a cut myself ! So decide to sort that before i have breakfast, i go to the shower room and turn the shower on , after getting in the shower i put some gel on my legs and lather it up , sliding the razor up my leg it feels odd , left leg done up to my groin, right leg done, left arm and armpit done , right arm and armpit done stomach and chest done ( Not that there was much) luckily I had only just had my back and bum waxed , my groin is trimmed, but I gel it up, I'm hard, and start shaving !
Once done I rinse off , my face is already clean shaven, I look odd with no body hair. I dry off , put my dressing gown on and go to the kitchen to make a coffee and toast.


More to follow soon !
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