Secret Shared

by Karin Roberts

 

Jim meets Tiffany

 

Christmas came and went and with the folks and family around dressing up games were cancelled for the holiday season. A couple of days before New Year I was relaxing in the lounge watching a re run of an old movie when the telephone rang. My mother answered it and called "Colin it's for you" stepping out into the lounge I picked up the receiver "Hello" "Hi Colin did you have a good Christmas" "Oh it's you Jim, yes thanks what about you" "Yeah it was fine, look I've called to put a proposition to you. When do you go back to college ?" he asked "Not until the ninth how" "Well my parents are off to my Aunts in Dundee the day after New Year and I've slipped out of it" "And" I asked "Well you know I said that I wouldn't mind seeing you dressed how about you come over here and for a couple of days and you can dress up till your hearts content." I paused the thought was very tempting a couple of days dressing up with a friend no chance of getting caught "Eh I'm not sure" I said nervously " Oh go on when are you going to get a chance like this again. I might even let you borrow some of my mom's stuff" Well that clinched it the thought of all her sexy gear , "Ok then I'll clear it with my folks" "Good see you Friday then"he said "Yeah no problem see you then" as he hung up.

For the next couple of days I was in a dreamland half the time thinking of what the weekend would bring both nervous but excited at the same time with the prospect of getting a couple of days to myself, maybe I could even talk Jim into a damsel in distress scenario get him to tie me up , be completely helpless rather than knowing that I could get free any time I wished. My mind was in overdrive with plans and I could not wait !

Clearing my visit with my parents was no problem, I think they quite liked the idea of me being friends with Jim as his parents were rich and came from the better part of town. So when the day came I set of with my bag packed with my limited fem wardrobe and of to a couple of days of my private hobby. As I neared Jim's my nerves increased what if he laughed found me ridiculous etc. I reassure my self thinking what the hell if he did at least I would know how good I was and whether I had any chance of looking a convincing female.

As I arrived at Jim's I nervously looked around half expecting his parents had returned and our rendezvous would be cancelled, but no sign as I stepped up to the door and rang the bell. Jim answered "Good to see you" he said as I stepped inside "Your parents gone then"

"Yeah they rang this morning from my Aunt's there not coming back till Tuesday now so we have the whole weekend to ourselves. You want a drink first or just get started" "I'd love a coke" I replied "Fine come on through" he said gesturing towards the large lounge.

Inside the lounge which was huge his dad had built a small bar complete with optics and a couple of bar stools. I walked over and slipped on to one of the stools. "Ice" Jim asked "Yes please" I responded. "So what do you want to do" I asked "Just a normal day, just like it was just Jim and Colin having a day together only you can dress up. By the way have you given yourself a girl's name when you get dressed." "No it's only ever been me on my own so I've never needed one," "Well I think you should have one today what do you want me to call you" "I don't know I've never thought about it" I responded. "Well is there any girls names that you like" "Eh well I've always thought Tiffany was quite nice" "Oh yeah I wonder why" he said with a smirk. "What" I said "Didn't you used to have a crush on Tiffany West at school" "No I didn't" "Yes you did but I not arguing with you Ok Tiffany it is so do you want to go and change Tiff, I'll meet you back down here" he said. I drained the last of my coke and taking my bag headed off up stairs. "You can change in my parents room" he called after me "It's the first door on the left at the top of the stairs." He was of course right I had had a crush on Tiffany West who was a lovely looking girl with long blonde hair, nothing had ever come of it though and I wondered what had happened to her as I opened his parents bedroom door and stepped inside.

The bedroom was huge there was an on-suite bathroom a large dressing area and a huge double bed with a fancy ornate gold metal headboard. Eh ideal for tie up game I thought easy to secure the wrists and ankles to the metal bars. Oh stop it I said to myself your just here for dressing up there is no sexual link between me and Jim. I opened my bag and carefully took out the items that I had brought with me. I had bathed at home last night eager to get my look as good as possible I had used a hair removal cream as I bathed for the first time, after all it was the dead of winter and some time before I would need to bare any of my now hairless body to the naked eye. I stripped off and pulled on a pair of lacy black panties ripping of a piece of tape from the role in my bag I taped my manhood back between my legs and pulled the briefs up as tight as possible, I took a matching black bra from the bag and putting my arms through it fastened the catch at the back. I stepped over to the dresser and looked at the array of cosmetics on display that Jim's mum owned there was everything imaginable in a vast array of colours and shades. Expensive foundation and powders perfumes the works. I had brought my own limited make up bag with me but decided to use some of the foundation of his mothers. I selected a tone that I thought was close to my own skin tone and unscrewing the lid carefully tipped some out on to my fingertips. A couple of minutes I had a nice flat canvas on which to create the look of Tiffany. Twenty minutes later my look was complete I had not gone too heavy on the make up as I was trying to achieve just a day look and not a glamorous evening look that I usually try to portray. Light shades of pink on my eyes and some pink lipstick from my own collection a little black eyeliner on my bottom eyelid and some mascara not too heavy.

Pulling on my shorter blonde wig I secured it to my head with a couple of hair clips and brushed it out the fringe just resting on my eyebrows. Leaving the dresser I returned to the bed and began to select my clothing for the day.

I selected a simple tan pair of tights and pulled them up my legs the soft feel on my newly hair free legs sending tingles up my arms as I slid them on. Standing up I picked out a denim skirt around knee length that I had brought with me and stepped into it, I knew that I did not need my waist clincher for this skirt and decided to go without as I said earlier this was more about day wear than glam and I was not sure what we were going to be doing for the afternoon so comfort was more of a priority. A simple white blouse completed the look. I stepped over to Jim's mothers closet and looked for some shoes my high heels did not seem appropriate for day wear so I was looking for something a little more practical.

There was a large collection of shoes and heels in the cupboard some awesome styles and heel heights but I decided on a black pair which had just around two inch Cuban heels they were a bit tight but I could get them on and they were easy to walk around in. I had borrowed a couple of items of jewellery from my mother just a gold bracelet and one of her old watches risky I know but it was good to complete the look with a look in the mirror and happy with the way I looked it was off downstairs to introduce Tiffany to the general public, well Jim anyway.

I stepped down the wooden staircase my heels giving that familiar clicking sound on hard surfaces. Walking towards the lounge I opened the door and walked inside. "Jim you in here" I asked a wolf whistle broke out from my left. Jim was standing behind the bar making a couple of drinks. "What do you think" I asked intrigued in what he thought but nervous about how he would react. "Your really good" he said "I would never have known that you are a guy, you really do look the part" "Really" I asked "Yeah you look even more of a female than the transsexual at University, you would pass no problem outside" "One step at a time , I'm just getting used to being seen by someone else" I responded. "Here drink this" he said handing me a glass of blackish liquid with some ice in it. "What is it " I enquired "Vodka and coke" he answered "thought it might settle your nerves a bit." My hand shook a bit as I took the glass from him and walked over to the settee, carefully trying my best female sit down I smoothed the skirt under my rear and lowered myself down once seated I crossed my legs and took a sip from the drink. "So how does it feel being here dressed as a girl with me" he asked "I'm ok I was really nervous earlier but I'm ok now" He sat in the settee opposite and continued " You know I really meant what I said just know you are really convincing and would have no problem outside" "Thanks" I responded "what are we going to do for the rest of the day" I asked "Oh I thought we would just goof around play some PC game watch a bit of TV and listen to some music then you can change tonight and we can have some dinner and watch some more TV." "Sounds ok to me" I said finishing my drink and placing it on the coffee table in front of me.

So for the rest of the day that was entirely what we did, we played some PC games on the Jumbo screen that his dad had installed in the games room, playing football and golf games which were that much more realistic on this giant screen he had almost like being at the game itself, then a spot of afternoon TV around 4pm Jim suggested that I go and change for dinner as I got up to leave he said "Look I've been thinking why don't you put some warmer stuff on and we could go out for a walk" he suggested. "Eh I don't know" "Look it's dark now we could go for a walk along the street and up along the river bank there might be nobody around" "It's a big step for me" I responded "Look trust me, you'll be fine" he said "Ok" I said inwardly desperate to try it but nervous still the same as I trotted of to get changed.

Back upstairs I began to look out something to wear, In Jim's mum's wardrobe I found a pair of jeans and then in a side cupboard a roll neck sweater I figured they would be a bit tight for me so the waist clincher would be a necessity for the night ahead. I walked into the bathroom and began to clean the make up from my face with a cleansing lotion and some soft cotton wool. Once I had finished removing my make up I figured I had around an hour before needing to get ready again so I relaxed back on the bed and reflected on the day so far. The reaction from Jim had been great, encouraging and just as if it was how he normally saw me. For him it had just been a day with a friend for me it had been a landmark and tonight was to get even better with my first trip outdoors. As I thought about what lay ahead I drifted of into a slight cat nap. Waking up about 45 minutes later I realised that it was dark outside and it was time to get ready for Tiffany's first outdoor adventure !

I pulled of my outfit from earlier in the day and slipped into a bathrobe. Once more at the dresser I began my make up foundation and powder this time with light and dark blue eyeshadow for my eyes and then some blue mascara that I found in Jim's mums collection finished off by some red lipstick not too bright but a nice shade. I decided to paint my nails and finding a nail varnish to match the lipstick I sat about painting them my nails were short and it did not take long to carry out the task and then wait for them to dry before applying a second coat. Once dry I picked up my waist clincher and slipped it on pulling the laces in I reduced my waist by a couple of inches which I figured would be enough to fit into the jeans. Sure enough I pulled on the jeans and they fitted nicely I was even quite impressed with the look of my nice round firm bum in them. Fastening the catch I took the wine roll neck sweater and having carefully removed my wig pulled it over my head and tucked it inside my jeans. The sweater as I expected clung to my outline exposing a nice chest size and a nicely reduced waist. Now for shoes Jim had mentioned the river path which I new was not that great a surface so stilettos would be out. Opening the cupboard I looked for suitable footwear suddenly at the rear I found several pairs of boots a couple had high slim heels but there was a pair although around 3 inches high was a block heel this will do nicely I thought removing them from the cupboard I unzipped them and slipped my feet into them pulling the zips closed with my jeans inside them the black leather settling just below my knees, perfect I thought. Selecting a black wool coat which came down to just under my waist and a pair of black leather gloves I left the room and headed of downstairs.

As I stepped into the living room I could see Jim was busy on the telephone "Yes mum everything is fine, yes Colin is here and we've had a good day do you want to speak to him, Ok here he is" as I waved no at him desperately as he pointed the phone in my direction. I had to take it "Hello Mrs Evans, yeah thanks for letting me stay over yes were just going out for a breath of fresh air and then have some dinner. Ok we won't stay up too late. Do you need to speak to Jim again, no ok yes you too have a nice break." While this was all going on Jim was in knots of laughter until I put the phone down. "You shit" I said,

"What it was so funny you standing there making small talk with my mother while your dressed in her clothes" walking towards him I slapped him with the gloves and said "Ha Ha now are we going or what" , "Ok let me just get a jacket" and he skipped off upstairs.

Once he returned I asked "You sure about this" "Yeah no problem you look so convincing and we'll hardly meet anyone at this time, so lets go" So as he opened the door I pulled on the gloves and Jim and Tiffany stepped out into the night air for the first time.

Walking along the heavily lit path with Jim my heart was pounding out of my chest this was the highlight for me so far. Out dressed as a young woman walking along the street all be it in darkness but I was outside. Several cars passed us with me half expecting one to stop and the occupants to leap out and ridicule me or should insults. But none did Jim obviously could sense my nerves and kept up a running conversation none of which I heard or understood as I was too busy savouring the moment and concentrating on my walking terrified that I would trip in these boots and give myself away. In no time we had reached the river path and turned down it, "We'll just go as far as the bridge and then turn back that should be far enough for today" Jim said "Ok" I mumbled finally acknowledging something Jim had said since we left the house. We were around 200 yards down the path when I saw two people approaching us a man and a woman walking their dog. I froze momentarily Jim sensing my mood said "Tif it will be ok nobody can tell, now just calm down" and he began to move on with me following. Closer and closer we got with my stomaching tightening as we moved towards them just as we were about 50 yards from them Jim reached down and took my gloved hand. I glanced sideways and he just smiled as we the approached the couple "Nice night" the gentleman said as we got to them "Yeah it is" Jim replied "I love your jacket" the woman said looking directly at me "Eh thanks" I stuttered as we passed them and walked on. Once out of earshot Jim said "See I told you it would be ok" "Eh you did" I said as we walked on. What had really calmed me down though were the tingles that were running through my body because Jim was holding my hand.

The remainder of our walk went largely unnoticed and we arrived back home and opening the door stepped inside "Superb" I said with a broad smile "I told you it would be ok, you really look good and have no trouble passing", I could have kissed him but was not sure how he would react so I decided not to and took of my jacket. We both went into the kitchen and Jim opened the fridge "What do you fancy for dinner" he asked "Oh anything I'm on too much of a high" I responded he laughed and took out a couple of simple microwave dinners for us opening them out and pushing them inside the microwave "I think we deserve a treat how about a couple of glasses of wine" he asked "Fine by me" I said "Ok, I'll just get a bottle from the cellar" he said turning and leaving me along in the kitchen. Today had been just perfect so far and I had another day still to go I thought to myself, this was definitely the best experience of my life so far and I was grateful to Jim for giving it to me. I wondered how he would react if I did flirt or come on to him but as I heard him coming back I decided to leave it for now as I did not want to put tomorrow in jeopardy.

We ate in silence Jim had uncorked the wine and I sipped my glass enjoying the moment.

Once finished we retired to the lounge to watch some film that Jim had suggested we watch, in truth I was too excited to concentrate on it but watched it anyway. Once it was finished Jim went back to the kitchen and brought through the remainder of the wine and poured a glass for each of us. "Tiff there's something I need to tell you" My heart stopped as I looked up at him "What" I said "It's about tomorrow you know I said that we would have the weekend to ourselves well when my mother phoned earlier she told me that we have a heating engineer coming tomorrow to work on the boiler" "So are you saying tomorrow's off" I asked "No not off but the engineer is booked and I can't cancel it" "Oh well do you want me to dress as a boy" "Well I don't want to spoil your time could you maybe just stay out of the way, I'll make it up to you, we'll have a good night tomorrow night maybe order in a carry-out meal and have some fun. You know like a dinner party you can dress in one of my mother's fancy evening gowns, how about it." "Yeah that sounds great and you are helping me so much so I do owe" "Thanks" he said "Now lets polish of this wine and I'll get another" he said pouring another glass.

Back with the other bottle we sat closely on the floor of the lounge chatting about days gone buy about people we had gone to school with, what they were doing now etc etc.

Finally Jim said "I think it's time I gave you your Christmas present" "Eh what" I said surprised "I'm sorry but I never got you anything" I said with regret "It's ok my dad gives me such a large allowance I never know what to do with it so I bought something for you" he said getting up and heading out into the hallway, minutes later he returned with a package and handed it to me "There you go open it" he said I tore open the paper and pulled out a box marked Ragazza "What is it" I said "You'll see" he said as I opened the box. I gasped as I looked inside there was an absolutely stunning blonde wig I guessed it was just over shoulder length with a front fringe it was really thick and luscious and felt very natural "What do you think" he asked "It's stunning you shouldn't have" I said fighting back the desire once again just to give him a big kiss. "It's real hair" he said "Top of the range, you can wear it tomorrow night" he said "I will" as I struggled not to start crying.

We sat up for around another hour finishing off out third bottle of wine as the last glass was drunk Jim said "I'm beat it's been a long day, I think we should call it a night" "Yeah maybe we should" I said feeling rather the worse for wear and conscious of the fact that I had spent the last half hour staring into Jim's eyes as we had talked. Getting up I stumbled slightly Jim grabbing my arm "Oops I said maybe a little too much wine" "Yeah probably, look I'll see you for breakfast ok, I'll just clear up here" "Eh ok" I said picking up my gift and heading towards the door as I reached it I turned "Jim" I said "Yeah" "I just wanted to say thank's for today" "No problem" he said "I've enjoyed myself too now sleep well" I will you too" I said and stepped out of the lounge and towards the stairs.

Carefully negotiating my way upstairs I slipped into Jim's parent's room I wanted the day to go on forever and had an idea. Opening one of the dresser drawers I looked for a suitable nightgown. I finally found a red lacy short silk sexy and took it back to my room with me, I was desperate to see what the wig looked like so opening the box I took it out and brushed it out removing my own I tossed it on the bed and pulled my new present on. It was stunning a short fringe coming to just above my eyes and swept back in a thick mass of hair which as I thought fell just below my shoulders. I quickly removed my clothes taking everything of including except my panties and stepped into the nightgown which fell to about five inches above my knee as I pulled the spaghetti straps over my shoulders. "Very sexy I thought the short night dress and gorgeous new hair style. I walked towards the bed and climbed up positioning myself sexily leaning on the pillow's I imagined Jim opening the door and coming to me easing down beside me and reaching out to massage my breast his mouth moving closer to me as his hand gently moved up my leg his breath on my neck as he tenderly kissed it as he slid up on to the bed. Gently cradling my cheek he turns my face towards him and moves forward until our lips meet. My mouth opening and out tongue's meeting, as my eyes closed in a perfect bliss his hand moving up my stomach and on to my breast squeezing the nipple me lost in ecstasy as I stoke his firm bottom. And then, nothing.

I woke up several hours later cold and a bit hung over the effect of the alcohol had taken over and half way through my fantasy I had blacked out. Climbing of the bed I removed the wig and placed it carefully on to the chair before turning out the bedside light and climbing under the covers I went back to sleep, hoping my dream would return and I would discover the end.

  

  

  

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