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My thanks go to Mistress Leigh for giving me the experience and allowing me to publish.
My thanks also go to SlaveGirl 70 for her insight and editing assistance.
I stood there, naked as usual, with a quizzical look on my face. To my complete surprise, today’s list of clothes was nothing like the usual elegantly sexual dress and lingerie, body hugging nylon and lycra or rubber fetish wear that Mistress usually wears to work, but a selection of simple clothes that any woman might wear for the day. There was also a selection of male clothing! No man stayed last night so what these were for was beyond me, but as instructed, I entered the walk-in wardrobe (a converted box room) and sought out the items listed.
Mistress Leigh’s clothing for the day consisted of a pair of standard knickers and smooth cupped bra, both in white cotton. A pair of 20 denier shiny nude tights (she always wears stockings. I have never known her to wear tights before!), a pair of denim shorts and a white T-Shirt. I also found the man’s items, which were a pair of black briefs, a pair of beige chinos, a pair of brown cotton socks and a dark green, long sleeved, cotton shirt. All of these items seemed quite small for a man, as if they were for a boy, which just confused me even more. There were also two belts; one, a wide black leather Hugo Boss belt, for the man, and the other Yves Saint Laurent, again made from leather but covered with a gold fabric, for Mistress.
As is our normal weekday routine, by 7am I was brushing Mistresses hair whilst she checked her e-mails. Today, however, I broke the rules by speaking first and asked Mistress about the man’s clothes.
“Don’t be insolent!” Mistress snapped. “All will be revealed when I decide.”
At 7.15 Mistress arose from the dressing table and stood by the chaise longue ready to be dressed. As usual I removed her black, silk nightie and held the knickers for her to step into, which she did. Mistress then sat on the chaise longue as I stretched the tights over her feet and started to smooth them up each leg. Not having dressed Mistress in tights before I was at a bit of a loss as to what to do when I reached her thighs, but Mistress stood up to allow the completion of stretching the tights over her upper thighs, hips and waist.
I then held out the shorts, which Mistress again stepped into and I pulled them up to her waist. I had to tug quite hard, as they were a very tight fit, but I was aided by the slipperiness supplied by the tights. Before I could close the zip and button Mistress turned around, intimating that I should put on her bra first. I clipped the bra behind her back and when she turned around again I settled Mistresses’ size C breasts into the cups. This particular style of bra had the effect of pushing her breasts together and up, thereby emphasising their size and shape. I slipped the T-Shirt over Mistress’ head and pulled it down over her body. It was a very snug fit and had a logo on the front which read, “Dream On” in gold glitter and “I’m with him” on the back, in smaller black lettering. I tucked the T-Shirt into Mistress’ denim shorts and closed the button and zip before finishing off with a thin, gold belt.
To my further astonishment, Mistress now said, “Now it’s my turn to dress you. Bring me the grey box from my dressing room.” I did so and Mistress removed a prosthetic penis attached to a harness. The penis was designed in such a way that it had a cup shape to the inside, testicles hanging below and a cock ring around the base of the penis to which the harness was attached in four places. Mistress drew the harness up my legs and clipped the belt closed at the small of my back pulling it to a tight fit around my waist and thighs.
“Right. Settle the cup firmly onto your vagina whilst I adjust the straps,” Mistress instructed. “You will notice it has a hole in the end, just like a real penis. This is the end of a hollow tube running the length of the prosthesis, which will allow you to urinate standing up like any man, and you will do so all day today. To ensure it doesn’t leak you will need to hold it firmly against you, just like any man holds his cock to piss. And don’t forget to squeeze and shake when you are done otherwise it will drip into your pants.”
I was flabbergasted! What on earth was going on?
The next step was for Mistress to tightly strap down my small size B breasts with flesh coloured latex tape in order to flatten the tell-tale feminine shape from my upper body. Mistress then pulled from the box something I am more used to wearing: a corset. But this was a corset with a difference. I put it on and Mistress laced it up quite tightly around my waist and once it was fitted I could feel it compressing my waist by a few inches, as normal. Mistress then used a small hand pump to inflate pockets around the waist, which straightened out my figure to that of a more shapeless man’s torso. The air pockets at the front even gave me a six-pack!
I then put on the men’s briefs and Mistress helped bursa escort me adjust my new 5″ penis into place. I pulled the trousers up my legs, which were an exact fit for my small frame, explaining why I thought they were for a boy, and held them tightly against my padded corset with the belt. I then donned the shirt, which was a looser fit and so designed, Mistress informed me, to more easily disguise my natural shape. Unfortunately it also hid my new six-pack. Easy come, easy go! I finally sat down and put on the brown cotton socks.
Mistress then sat me down at the dressing table and proceeded to clip up my long blonde tresses under a hair net, spreading them evenly over my head, before using hair clips to hold in place a man’s style wig of collar length, short black hair. The final touch was a small black moustache, å la Errol Flynn or David Niven, held in place with theatrical glue as used for movie special effects make-up. The transformation was astonishing. I now looked like a young man, albeit a somewhat effeminate one.
“Go and make us both some tea and toast for breakfast and I will join you shortly,” Mistress said as she sat back in front of the mirror to complete her own make-up for the day.
Mistress will ‘join me’ for breakfast? This was becoming a very strange day.
I walked downstairs with some very strange feelings, both emotional and physical. The attachment between my legs seemed to get in the way with every step, despite being firmly held in place by the harness and pressed against me by the briefs. And after almost two years of my legs being constantly and tightly cocooned in either nylon or rubber it was odd to feel material rubbing against them as I walked.
I prepared some more tea, made some toast and, as instructed, set the dining room table for two with a pot of English Breakfast tea and milk. With the toast I laid out some butter, marmalade, honey, raspberry jam and a bowl of assorted fruit. Mistress joined me after about ten minutes having applied her cosmetics simply and found me standing next to the table, nervously waiting.
“Sit. Join me. Eat something,” Mistress stated, “and I will explain what is to happen today.”
As we sat and drank tea and ate toast together, I felt extremely self conscious and uncomfortable, not only because of my new body parts and look but also because I was not used to being treated as an equal.
Mistress began her explanation of what was going on. “Today you are my boyfriend, suitor or whatever you will, and are taking me out on a date to impress me. You are in charge. I am NOT your Mistress today and you will NOT call me that. Neither are you to call me by my name. I am sure you can think of a pet name or two for me to use throughout the day. You are to be romantic and chivalrous at all times and treat me like the woman you wish to attract and keep. I will follow your lead and behave as would any woman being ‘pursued’ by a wannabe partner or husband.”
“There is a wallet full of cash for you on the hall table”, she continued, “and you are its custodian. Spend it as you wish to impress your ‘sweetheart’. I will tell you what you need to know as the day progresses. Finally, to pass as a young man, you will need to lower the pitch of your voice when you speak and walk with a manlier gait. To do that you need to forget your training and walk with your feet parallel, instead of in line, and with long strides. I know it will be difficult to remember, but I am sure you will manage. Hopefully the unfamiliar genitalia between your legs will assist in keeping your legs apart as well as being a constant reminder. When we are done with breakfast you can clear away the things and then call a cab to take us to Waterloo station.” Yet another strange occurrence, as I have never known Mistress to use the train.
We finished breakfast in silence, Mistress reading the newspaper whilst I nibbled at my toast and honey trying to make sense of what I had just been told. By the time Mistress had finished breakfast my mind was a whirlwind. I cleared the breakfast things away but when I telephoned the cab company I completely forgot about lowering my voice. Never mind, they couldn’t see me so I suppose it didn’t matter this time.
On the table next to the phone were the house keys and the wallet Mistress had mentioned, stuffed full of cash. I put the wallet in the back pocket of my chinos and closed the pocket’s button. I was daunted by this as having not been out in the big, wide world by myself for almost two years I had no idea how much things now cost, but there was a lot of cash in the wallet.
Mistress joined me in the hallway, gave me the keys and reminded me that I was in charge, and sat on one of the chairs by the telephone table and kicked off her slippers. It was only now that I realised I was wearing my mule ‘slippers,’ which I had put back on as habit after earlier donning the socks. Pink, fluffy 3″ heels must look most incongruous with my male attire. Mistress also noticed and laughed out loud. bursa escort bayan “I think you may get some pretty strange looks wearing those today,” she chuckled. “You will find our footwear for the day at the front of the shoe cupboard.”
I retrieved said footwear from the cupboard and helped Mistress into a pair of long, black, thigh high boots that had a 4″ Cuban heel and extended half way up her thighs, leaving only a few inches of her shiny nylon tights visible between them and the cropped, tight shorts. Mistress folded down the top 3″ of the boots, pirate style, which now left about 5″ of visible nylon clad thigh. I must admit that Mistress looked pretty hot in this outfit, especially the way the shorts clung to her shapely behind. The boots showed off her beautiful, long legs and the tight T-shirt emphasised her firm breasts. Mistress then picked up a small, black leather handbag, which she slung over her left shoulder, ensuring the strap crossed between her breasts to further enhance her cleavage.
My shoes were a pair of lace-up, brown leather ‘Oxford brogues’ with a heel of about half an inch making us look totally mismatched. A young, nervous, effeminate looking ‘boy’ of only 5’7″, plainly dressed, paired with a confident, sexily outfitted, older woman (with all due respect, Mistress) who towered over him at 6’2″. The ultimate odd couple!
The cab had arrived promptly and it was a little before 9am when I locked the apartment door as we left (another weird feeling). I completely forgot to pay the cab driver as we got out at the station and Mistress had to nudge me to remind me. As we walked into Waterloo station I tried to affect a male ‘swagger’ and Mistress grabbed my hand and smiled at me. I nervously smiled back and we continued on to the ticket office.
“Two returns to Chertsey,” Mistress whispered in my ear as we approached. I nervously requested these tickets in such a false low voice that the woman behind the window looked at me strangely, and then smiled. I have no idea if this was because she saw through my disguise or just thought I was a nervous young man, but I think the former was more likely.
We proceeded to the busy platform and, as we waited for the train to arrive, I suddenly realised how small I felt. During my time with Mistress I had always worn heels of at least 5″ when around other people, and a minimum of 3½” with Mistress herself when she was barefoot. I had become accustomed to being 6′ tall, give or take an inch, when with other people. Today I was only 5’7″ and for the first time in ages I felt lost in the crowd as almost everyone on the platform was at least my height or taller. Mistress bent down, hugged me and kissed me firmly on the lips for all to see. Mistress elbowed my arms towards her and, having got the hint, I clasped her firmly in return. “I am so looking forward to today, Darling.” she cooed in my ear as we broke our embrace. This was definitely turning into a most surreal experience!
The train journey was just over half an hour and we spent this time making romantic small talk interspersed with the occasional kiss and cuddle. I cast my mind back to my university years and tried to remember how my boyfriend treated me back then when we went places together. Mistress was calling me ‘Darling’ so I started calling her ‘Honey,’ which was his pet name for me. The looks we got from other passengers ranged from curious stares to downright distaste. I was beginning to think it was obvious that I was a woman posing as a man, at least when under closer inspection. Or maybe I was just being paranoid? I mentioned this to Mistress, but she assured me that it was just the general reaction of different people to a loving couple snogging in public?
We disembarked the train at Chertsey and Mistress instructed me to get a cab to Thorpe Park. OMG! We are going to a theme park for the day. I had been to a theme park once before with my university boyfriend and enjoyed most of it, although some of the rides were really scary.
With me being in charge for the day, can I refuse some rides, or does Mistress expect me to ‘man up’ and go on everything? I guess the latter applies, as I am ultimately still her slave.
We got to the park, and this time I remembered to pay the cab driver as we exited. We again held hands and joined the queue for tickets. As I had been earlier informed that money was no object, I purchased two ‘fast track’ passes along with the entry tickets, which allowed us to jump the queue at every ride for the whole day. I know Mistress never likes to wait for things and I think she was pleased as she smiled at me when I did so.
Once through the gate the first thing I purchased, as instructed in the cab, was a refillable drink bottle, which I immediately had filled with coke and started drinking. Mistress wanted me to use the toilet several times today so I was to drink a lot. After two cups of tea this morning I already needed to use the bathroom and was somewhat apprehensive bursa merkez escort about doing so. “Do you mind holding my drink, Honey,” I asked stiltedly, “whilst I use the toilet?”
“Of course not, Darling.” Mistress replied with a smile. I headed for the toilet block and caught myself almost going into the ladies. I casually changed direction, hoping nobody had noticed, and continued towards the gents’ door. Obviously I knew of the layout of a gents’ toilet, in comparison to a ladies, but I was not fully prepared for the impact of the feeling I had of being in the ‘wrong’ place.
I was so nervous about standing at a row of urinals, next to a line of men with their cocks out, and I desperately tried to act natural as I crossed the room to do something I never had before. I suppose I could have used a stall, but if Mistress questioned me later I know I would be unable to lie to her and would be in trouble after all the effort she had gone to arranging the day. I moved to the urinal in the corner and stood at an angle in order to hide myself from the rest of the room. I unzipped my trousers and struggled to pull my ‘penis’ out from the briefs. I finally got it free and, as instructed, pressed it firmly against my vagina and tried to pee. This was not as easy as it might sound at first, as I have never urinated from a standing position. I had to overcome the overwhelming impression that I was about to wet myself and force myself to ignore the natural tendency to try to stop peeing. It seemed like ages before I could force myself to complete the ‘task at hand.’
What a strange feeling it was. There I was, feeling like I was wetting myself, but actually watching a stream of piss pouring out of the end of a 5″ long, 2″ diameter, tube of rubber I was holding in my hand. I realise this was as natural as night and day to a man, but it felt really weird to me. When my flow finished, I squeezed the latex phallus in my hand and shook it so vigorously that a man at the next urinal gave me a strange look. I again struggled to replace it in my briefs but eventually succeeded and finally closed the zip on the trousers. I went to the sink to wash my hands and as I did so I noticed in the mirror how red and flushed I looked. My uneasiness and embarrassment with the situation was plain for all to see but the reason for it was no doubt a mystery to those same observers.
I rejoined my girlfriend (as I will now call Mistress) outside on the terrace around the entrance building and joined her in surveying what we could see of the park from here.
“Are you alright, darling?” she enquired as I stood next to her.
“Yes, honey, I’m fine, thank you,” I responded. “Just a little disconcerted and self-conscious.”
“Don’t be. You’re doing fine.” she reassured me. “Have another drink and let’s get on a ride.”
It was now ten-fifteen and we made our way down the steps into the park proper. Needless to say that during the day we went on a number of roller coasters and, in contrast to my manly appearance, I screamed like the girl I am on all of them despite myself! Surprise, surprise, eh?
Within an hour I began to relax, in no small part to my girlfriend making me feel more and more comfortable about the situation with her small talk and jokes, etc. Mistress really was behaving as if she was just out on a date with her boyfriend. Most of the time spent walking between rides was done holding hands and whenever we were in one of the fast track queues we tended to have a short kiss, or sometimes a bit longer if it seemed to annoy someone nearby.
By lunch we had been on half a dozen or more rides and I had been to the toilet again, but felt less anxious on this occasion. We had lunch at a KFC, which I chose, as I hadn’t had fried chicken for about two years and I really fancied it once I caught the smell. I had to eat mine carefully, as I didn’t want to get the grease on my moustache and have it fall off during the afternoon, but otherwise it was most enjoyable.
With all the walking and standing around, I had gotten used to my male parts during the course of the morning and had lost my feeling of self-conscious paranoia. After lunch however, as we strolled around the park towards the next ride, another less predictable problem soon made itself known.
I had spent the last 21 months or so in servitude with Mistress, and during that time the smallest heel I had been permitted to wear were my 3½” mule slippers. The only time I did not wear heels was in the shower or at night whilst asleep in bed, but I was even required to wear my slippers if I left my bed to use the bathroom during the night, which was admittedly a rarity. Generally, throughout the day my various uniforms consisted of five or six-inch heels. It had taken some time to become accustomed to constantly wearing such towering heels and when I first began my servitude the balls of my feet were killing me by the end of each day and even the 3½” heels were a blessed relief. However I was now completely acclimatised to tall heels and thought nothing of wearing them all day. Today it seemed I was having exactly the opposite problem as my feet, and especially my calf muscles, were really beginning to ache due to the total lack of heel on the shoes I was now wearing. Who would have thought that NO heels could be painful?
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