This is a work of FICTION for ADULTS only. Do NOT read this if you are under 18 or if you are not an adult according to the laws of your state or country. Do NOT read this if you are offended by fantasies involving sexually explicit material.

Comments welcome to bethjac@hotmail.com and/or sararever@hotmail.com

 

Ian and Me                         Co-authored by Bethany Jacques and Sara Rever Eveille

 

1 - Just friendly fun

It wasn’t really Ian’s fault, the way it turned out, Just two guys having fun, being mates together, supporting each other. Me, the goalie in the team, and Ian the striker. We had known each other for years, since school, got drunk together, pulled girls together, even on one memorable occasion fucked two sisters together. We were just ‘mates’. And we were sympathetic to each other’s needs and desires, not the least in helping each other in our ‘hobbies’.

Ian’s is fairly harmless. He finds it totally fascinating, me, well, I can see why but quite a few of the other guys in the team would have poked fun. He collected stamps. I know, a wimpy hobby for a macho guy like Ian, big he-man striker, but he liked it, and I could see his point. I was just someone to appreciate what he had done, look at his collection, act as a sounding board. That’s what mates are for, surely. But my hobby, well. At least that’s what I call it, my hobby. I like to get dressed up, of course, but I am maybe a bit strange. I get a great thrill from dressing in women’s clothing. OK, it sounds a bit weird but I enjoy it, and it doesn’t do anyone any harm. And Ian was my audience too, I liked to show him a new bra or a pair of earrings, anything to make me look and feel a little more feminine. But I had never had the chance to go the WHOLE way. After one session when I had shown him a new make-up I had bought, and been very pleased with the result, Ian had suggested it. "You know, Richard, I think you could. You know, look the part, look properly female I mean. You’ve got the legs for it, I know that, when you got those new stockings a couple of weeks ago, your legs looked great. Really. You should try the lot, in one go."

So we had agreed, the next Thursday evening, I would try. Good Friday next day, no football on the Saturday, we were playing Easter Monday. A long weekend, and an opportunity to dress up at the start. I am not too tall, about 5-9 in stocking feet, quite thin, fair haired, quite round faced, I had been impressed with my own attempts at dressing and looking good, I really did think I could look a presentable, maybe even an attractive woman. And that evening I was going to make the most of the chance. The planning took me all week, calling in at shops on my way home from work to buy just one more makeup item, one pair of tights or stockings, one pair of clip earrings etc, sometimes in with normal family shopping. And on the Wednesday before MY Thursday, I had stopped at a ‘sex-shop’ on the edge of town. I had driven past it many times but never dared call in. But this time I did. I had rung them a few days earlier to ask about a couple of things and been told that, yes, they did cater for transvestites (that’s people who dress as the opposite sex) and had quite a range of things. I asked about underwear, and wigs, and prostheses. The answer was yes to all, when I had told the guy in the shop what that last one meant, false breastforms and caches to cover up my private parts. OK, only Ian was going to see me but I desperately wanted to FEEL the whole thing, to ‘be’ female outside and in, or at least as much as I could.

I was nervous when I went in, I told the guy it was me who rang about cross-dressing, I was still nervous when he turned and opened the door and went into the back of the shop. I looked round, fortunately there were no other customers, I had dreaded meeting anyone I knew in there. And I was VERY nervous when, from the back of the shop, a woman came to offer me some assistance. She was rather matronly, a bit large, about 40, but turned out to be very friendly indeed. Probably used to guys like me with strange requests, in fact probably used to people much stranger! She asked my briefly what I was after, then led me to the back of the shop and round behind a shelf. I expected to see a few wigs and so on, but there was a whole room there, with everything I could have imagined and more, wigs, shoes, dresses, undies, breastforms, makeup, the lot! The clothes were fantastic. I looked at a bra, gold, gorgeous lace edging, and very low-cut, it would show off a girl’s nipples. And a skirt, tight red leather, I knew it was called a hobble skirt and it was obvious why, gold buttons right down from the waist to the ankle. Lovely! She saw my eyes open at the sight, and smiled.

"Now then, tell me again, you mentioned breasts and a cache, what do you have in mind."

"It’s a bit strange, I know, but I have the chance to dress up a lot at the weekend, and I want to really do a good job. So I really wanted to get some special forms instead of just padding a bra with tights and so on." "It’s not strange at all my dear" she replied, smiling again, she really was good at putting customers at their ease, AND at guessing exactly what they would like, or rather what she could sell them. "Now, looking at your frame, you could probably wear pretty big breasts, would you like that?" She knew I would! I had intended taking about 15 minutes to get a few items, I left the shop an hour later. I had chosen the forms, to give me a really large bust, the assistant reckoned it would be 42DD, and a flesh-coloured latex cache. And the adhesive and makeup for the breastforms and the cache. And a pair of absolutely to-die-for shoes, and a really tight bustier to show off my latest acquisition. And a wig, blonder and more expensive than the one I already had but gorgeous, it was difficult to tell with my suit but I thought it looked good and Helen, that was her name, said it looked great. But then she would, wouldn’t she. The wig - well, I got it, and I got an extra pair of earrings too.

Excited though I was, somehow I got through work OK on the Thursday, and hurried home. That evening, having showed enormous self-restraint in not trying things on piecemeal, I began my own ‘makeover’. I took off my ‘work’ suit and hung it up, then stripped totally. The two cases came out from under the bed, the first large one containing all my feminine ‘goodies’ for the weekend, the second with male things, trainers, jeans, pants, socks etc, with some toiletries.

Then I bathed, not for too long because I was keen to get on, besides I had my ‘hair’ to do. I smeared depilatory cream, supposedly the best on the market, over my arms, chest, legs, everywhere it might be needed, then rinsed it off with the shower hose five minutes later. Then I undid the shower spray and fitted a nozzle to the end and gave myself a rear-end ‘douche’ - something I had read about in an online TV (transvestite!) magazine. It was effective, I felt ‘clean’ inside, though I must admit I didn’t get quite the thrill I had read about in the article. I had bought a large, lemon-yellow fluffy towel, and appreciated the smoothness of my skin as I dried myself. I had several new razors, I used one with very hot water to smooth my face, very carefully and thoroughly, twice. Back in the bedroom I got out the scarlet nail varnish, and did my toenails. Just for me, I wouldn’t even see them with the new shoes on, but it felt good. While the varnish dried I took the breastforms from the large case. These I had bought new, specially for this weekend. I NEEDED to see just what I looked like, and how I managed, with VERY large breasts. I had read the instructions with the adhesive carefully, several times, I nearly knew them by heart. One quick spray with the adhesive all the way round the edges, lie down, wait half a minute, press firmly into place with the nipples aligned, then wait three minutes. I gave them five to be sure, then sat up. That feeling was gorgeous, as I moved upright the weight of ‘my’ boobs pulled down, and they swung. As I moved from side to side, they moved, but just a little later, the result was very impressive indeed. Quickly, but not rushing, I got to work with the solvent, removing the excess adhesive round the edges, delighted with the colour, so close to my own skin tone, and with the edges, very smooth indeed. Again with the instructions to hand, I smeared and rubbed the makeup all the way round, rubbing it to blend in the edge of the forms with my own skin.

It was just beginner’s luck, I know that now, on occasions since I have had to clean up and start again, once I had to do that twice. But that first time I got the blend just right, I sprayed the fixative over the top and marveled as it dried at the seamless join between skin and artificial boob. Back in the bedroom I looked, carefully, at the cache. It was not of quite the quality of the breastforms, but it was good. I was a little aroused, obviously, but that helped as I slid the thin ‘condom-like’ tube over my own penis and tucked it tight between my legs. I sprayed the edges of the latex triangle with adhesive and pressed it into place, just like the breastforms. A few minutes later I teased a few pubic hairs across to hide the edges and inspected my crotch carefully. I had a pussy! A deep pink, glistening, pussy, complete with thatch, it looked as real as I had hoped. The adhesive was set so I padded to the bathroom to pee, and did so sitting down with no trouble whatsoever. I was feeling more female by the minute. By now I had to move. I slid on black panties temporarily, jeans, socks and trainers, and a large baggy sweater. I grabbed a big jacket to cover everything, grabbed both cases, checked my keys, cards, other necessities and loaded the cases in the car. Then I quickly locked up the house, got into the car, and headed off. Two miles to Ian’s house, then the fun would really start.

I got there just after 6.30 and unloaded, unlocked the door and switched off the alarm, and closed the door behind me. Safe for several hours! I took the cases upstairs and opened the large one on top of the bed in the bedroom, by now I was REALLY excited. It took me less than ten minutes to spread my outfit, wig, blouse, skirt, basque, new pack of stockings, shoes, on the bed. I put my makeup case and small jewellery box on the dresser and stripped again.

The process of dressing I was more used to, even though I was going so much further than before I made rapid progress. I took my makeup bag and padded into the en-suite bathroom to slide off my black panties, then squirted a little KY jelly onto my finger. I slid my finger up my ‘love-hole’ and smeared it round, the first time I had done that - it was cold. Then I pulled up my scarlet thong, silk, the tiniest I thought I could get away with (Helen had promised it would work and it did). When I looked in the mirror to check, the red triangle covered me at the front, and the thin strip up the back settled neatly into my crack, I loved it. The basque I had bought was red ‘silk’ and probably too small for me. I tightened the straps on the basque as much as I could, then sat for a moment. Then I stood and squeezed my stomach in as much as I could, and tightened them again. The basque was quite thin, did most of its job by elastic rather than steel strips, and really did take my waist in several inches, I knew I could cope with size 10 at least round the waist. The bra top was scarlet red, low cut, with wide straps, and supported my bulging breasts, doing just what I wanted, pushing them up and together and leaving a deep plunging ‘V’ between my breasts. I just knew I must have a great cleavage, but resisted the temptation to look in the mirror at the whole effect.

Instead I clipped the six red straps to the edge of the basque, and opened the pack of stockings. These I had been saving. I normally wear black tights or stockings to cover my legs but, having smoothed them, I delighted in something different, a pair of red hi-leg Aristoc stockings, 7 denier, incredibly sheer, they felt sensational as I rolled them smoothly and slowly up my legs and clipped them to the suspender straps. In the bathroom I got a new blade and smoothed my face in hot water, twice yet again. When I felt the effect I knew it was the best I had ever done. Then I started on my makeup. I had bought a brand new Givenchy set for the occasion, and tried out one or two of the colours earlier. After a very light foundation, I applied a rose bloom cover-all thinly, and rubbed it well in to give as near as I could to a no-makeup look. For my eyes I used a mid-blue, not too bright, over my upper lids, merging it into a mauve and a pink almost up to my eyebrows. These are not thick, I was able to gently brush and shape then to give just the right amount of colour, shape and definition.

Then the rest of the eyes, I do so love the sensuality of applying my eye makeup. A fine deep blue line along my lower lid, and then thick, very dark blue eye-curl mascara over upper and lower lashes, extremely carefully, thickening and darkening each lash almost individually. I teased my cheeks with the blusher brush, to highlight the tops of the cheek bones, then sat back and looked. I was thrilled with the result. I was almost, but not quite, ready for my final stages. I had not forgotten - the nails were going to be a bit special. But first I opened my jewellery bag and spread things out in front of me. I don’t really know why, I had already decided what I was going to wear. I clipped on my new thick gold hoops, nearly 3" across, and very carefully constructed so they looked as if they were fitted into pierced ears. They five rings, all ‘gold’, two with large red ruby-like stones on my right hand, three with thick gold bands on the left. I smiled a little as I slid the last onto my third finger of my left hand, it looked rather like a wedding ring. Finally two gold chains, one thin, one thick, both quite long, clipped round my neck so they both fell down and settled just above the edge of my breasts. I reached into my case and got the sexy red minidress I had bought at Miss Selfridge only the previous week. I was desperate to try it on with everything, boobs, nails, stockings, the lot.

It was scarlet, shiny, with a slightly rippled gold effect running all the way through it, and in a stretchy material which I just knew would cling to my ‘new’ body. I pulled down the zip at the back, then stepped in and gently slid it up my legs and up to my waist. The thrill was sensational as it slipped oh-so-smoothly over my nylons. I pushed my arms in, it was a bit tight, a size 10. It was a bit small for me but I was really sure it would look good on me. I settled the front part in place over my ‘breasts’, then reached behind me and pulled up the zip to the top, just above the level of my basque. Finally, before another brief rest, a 3" wide gold belt with a large gold buckle at the waist. I was delighted at how far I could take it in, I would estimate my waist at that moment was about 24"! I sat for a moment again, then got out again my nail varnish and my false nails, a lot longer than I had worn before. But I remembered - before them - my earrings, they would have been difficult to fit with such very long nails. I leaned over to the dresser to get them, a difficult task in such a tight outfit but I did it, and felt pleased at my success in coping. I clipped them onto my earlobes, two large thick gold hoops which did look as if they were fitted into pierced ears.

Then my nails. The toes I had done already, I laid out the ten long clear nails in sequence on top of a sheet of paper on the bed. In turn I put a drop of glue on my own nail, then pressed the ‘falsie’ firmly onto this. The last few were difficult to manage but they looked good, I thought. I took the top/brush from the bottle and began with the small finger on my left hand, worked my way across them all. I was taking my time, being extremely careful, by the time I had finished the first was dry. I started again and added a second coat on top. Again, as I finished I started at the beginning again, this time with a clear, hi-gloss top coat. This took a lot longer to dry, but I could wait.

And it was at this stage I stood and looked in the mirror, not for too long, just to confirm what I already knew. I looked a total fool. I did. But then my own three favourite stages, lips, hair and shoes. Without looking too closely, I took my new scarlet lipstick and began to apply it ever so carefully over my lips, aiming for that cute ‘bow’ shape. With this done I added a clear gloss coat of lip cover over my bottom lip to give what I hoped would be a sexy look, then very carefully outlined the lips with a lip pencil in a very thin line of a slightly darker red. Then I took my shoes, really tarty stilettos, 6" heels, scarlet and very shiny, from my bag and put them on the floor and stepped into them. I love the feeling I get when I do that, the slight tightening of the calf muscles, the re-shaping of the legs in a much more feminine way.

Finally I turned to get my wig, long and very curly and nearly blonde. Even with the long nails I managed to fit it first time. I tugged it into place and was delighted to feel the curls drop and settle over my neck, it was longer and more extrovert than the dark wig I had worn before. Just glimpsing in the dressing table mirror, I teased the curls into place. Then I turned and strolled across the room, enjoying the feel of the heels on my feet, and looked in the long mirror. I was thrilled. Looking back at me was a tallish, slender, voluptuous tart! The combined effect of the figure, the makeup, the clothes, the heels, it looked sensational, I really was delighted.

But really, I could, any man could, I really did think that I looked so good I could have any man I wanted to make love to me. I fantasised just for a moment about meeting a guy and turning him on. Then snapped out of it, grabbed my red handbag, pushed my keys and a small purse and some makeup into it, and went downstairs.

I paraded about for several minutes, feeling really excited and loving every glimpse I caught in the mirrors around the house. I even dared to go outside, knowing that at the back absolutely nobody would see me, it felt incredibly sensuous, the breeze on my legs, just blowing up my tight dress a little. I didn’t stay too long, headed back in and towards the kitchen. I settled there on a breakfast stool, crossing my legs, luxuriating in the feeling as one nylonned leg slid gorgeously across the other. I lifted the glass of wine I had poured for myself from the bottle I had brought, appreciating the thin lipstick mark on the rim. I picked up my red soft leather clutch bag and took out a pack of cigarettes, very long girly ones I had bought specially, and lit it with my new gold lighter. I looked down at my fingers, shiny red nails holding the glass, and lifted it to my lips again. I was intoxicated with the sheer pleasure of my experience. As I finished my cigarette and cleared away, I noticed the clock. Ian would be back in a few minutes. I headed upstairs, just in time.

I heard the front door open, and his voice call out "Richard, you there?" I started out down the stairs, seeing Ian’s back as he went into the kitchen and put his briefcase and the take-away down. In as gentle and sexy a voice as I could, I spoke.

"Sorry, Richard couldn’t make it, will I do?"

Ian turned round to look at me. It was maybe just as well be had put things down, I think he might have dropped them as he looked at me. His face was a picture!

"Christ! Richard! RICHARD! It is you Richard, streuth, you look great. Really great. In fact more than great, you look terrific. I mean it, really terrific. I can’t believe it!"

"Why thank you, kind Sir" I replied in my hopefully feminine voice, just a bit mocking but really enormously pleased at the reaction. "I am so pleased you find me acceptable" Then I dropped the voice, went back to normal.

"Really, Ian, honestly, what do you REALLY think?" "No, honest Richard. You look gorgeous! I would never have known, never, you look like - the phrase ‘sex on legs’ comes to mind, and you DO have sensational legs. Let me see you move then."

I paraded about he kitchen for him, glowing inside at the commendation from my best friend and, sometimes, sternest critic. On occasion Ian had been scathing of my efforts, specially just after I owned up to him. But now he was full of praise. After a few minutes like this we got down to the meal, had the Chinese Ian had brought, I tried to stay ‘in character’ all the way through it, to enjoy my first meal in company as Sara. I even volunteered at the end to make the coffee. As I leaned over to offer Ian’s mug to him he just had to say something.

"Jeez, Richard, I am sorry but I have to say this, those look like absolutely sensational tits, when I look down your cleavage I get a real hard-on. I’m sorry to have to admit it but it is true" And without realising it I made things worse when I sat down opposite him and crossed my legs.

"JEEZ ray, will you stop that!"

He just had to reach down and adjust his trousers! A few minutes later he asked the question I had been waiting for.

"Richard, you look so good. Have you ever thought of going out dressed, you know, as a woman, you could you know, for sure, you would have men all over drooling over you."

I smiled provocatively at him.

"Are you offering, Ian? Seriously I have never thought of it before. I just love dressing and trying to look good, as you know. But I do admit the idea has some appeal."

Ian stood and held out a hand to help me stand, then pulled me into the hall where he had a long mirror. he stood beside me as we both looked at the ‘couple’ reflected there.

"Well I could, maybe, we could go to a pub or somewhere, one night maybe.

Where nobody knows us, if you would like?"

But before I could answer, as we stood there in the hall - the front door opened!

 

2 - HELP !!

And in came a woman I had not seen before, maybe about 50, somewhat agitated. She looked at us both, came over and gave Richard a peck on the cheek, then spoke.

"Ian, my dear, how nice to see you. Sorry for dropping in like this. George has had car trouble, we had to get the AA on the motorway. He said we couldn’t get home tonight, so we thought we would call in to see you. Well, aren’t you going to introduce us?"

Ian was totally speechless. The silence was just about to become very embarrassing when the door pushed open again and a man, again about 50, squeezed into the hall. I realised - I took the initiative. "Please, Mrs. Lyons, come in, please, I’m Sara, pleased to meet you. You too Mr. Lyons, can I make you some tea?"

On the basic pretext that any mother, after being stuck in a car for hours, would really like some tea. It unfroze the moment, we all went in, Ian’s parents sat side by side on the sofa. I was getting away with it! For just a moment I had considered running out of the door, but my car keys had been behind me in my handbag in the kitchen. Or coming clean, telling them I was one of Ian’s weird friends, who thought it was fun to dress up like that. But I had continued the ‘role-play’, the pretence, and got away with it. As they sat I turned to Ian, who had still not said a word. "Darling, could you go put a kettle on please?" He was totally amazed. He just did it. I smiled at Ian’s Mum and ‘excused myself’, heading towards the kitchen to help her son. As I did so they both moved too, he with ‘I’ll just go and see what I can do with the car’, she towards the stairs with an ‘excuse me my dear’ in a tone which was supposed to indicate she was heading for the toilet. But I could tell, I knew better. I followed Ian swiftly into the kitchen, he turned on me and glared.

"What do you think you are playing....."

I placed my hand over his mouth and glared back. He got the message and shut up. I lowered my voice to a whisper.

"Ian, now, YOU listen. OK, we’ve a problem. But would you rather I had said ‘Hello, I’m Richard, a friend of Ian’s, he likes me to dress up like this’?" He looked back at me and past my shoulder, imagining what his parents would have thought.

"OK, now, we still have a problem. Let’s work together on it. As of now I am your girlfriend, Sara, remember that, Sara, don’t dare call me Richard. Now quick, get the kettle on, I’ll sort something in here, now get outside and see what your Dad is doing or they may be here all night!" And they were! I dutifully played the nice girlfriend all evening, provided tea to the men who were trying to fix the car and failing. Generator problems, they decided the earliest they could manage was an 8 am trip to Halfords. I managed to keep the chatting to Mother to a minimum, making excuses to go and sort out the spare bedroom, clean sheets etc, fortunately they were weary after the trials and tribulations of the journey. They went to bed early, so did Ian and I. Yes, we went to bed. Ian was stunned when he realised what would be happening. I got him on his own again in the kitchen to explain in a whisper.

"Look, Ian, work with me, I am desperately trying to get us out of this alive! Your mother thinks, or rather knows, we are sleeping together. I knew when she dashed upstairs, she was snooping, obviously saw our clothes, or rather my clothes, both sexes, on the bed. Added two and two and got four. She thought I was a slut, not fit for her son, if I don’t persuade her she’ll be on your back for months. You know that. What kind of a girlfriend do I look like, fuck-me shoes, a pelmet for a skirt, massive DD cup tits bulging out of my dress. Basically this outfit just shouts it. TART! Mother’s always want to see their sons at the altar with a ‘nice girl’. Do I fit the picture?"

Ian blushed, he knew I was right.

"So, Ian my darling, from now on I am sweetness and light to your mother, which is difficult with your Dad trying desperately to see up my knickers and get an even bigger eyeful of my boobs. Anyway, we can still do this. Streuth, we have seen each other naked even, in the showers after the match. We have to sleep in the same room, and tomorrow morning I do breakfast, you and your Dad fix the car, then they are off. Then tomorrow or later you ring them, Mother will want to know all about me. So you tell her it is off, say that a mate saw me, ‘Sara’, necking with another man in a pub or something. She will think ‘I knew she was no good for my son’ and be all consoling. End of problem. OK?"

Most of the plan went OK. The only problem was in the bedroom when I took my dress off to reveal my scarlet undies and stockings to him. "Christ Richard" whispered Ian. "Quick, come on, I’ve got problems." I looked round - he had, he was trying to take his pants off but had seen me. His erection was enormous. I grinned.

"Not now, darling, we have to sleep."

We slept on opposite sides of the bed, both a bit restlessly. I got up at seven, crept in the bathroom and emerged smooth-faced, fresh makeup and so on, looking radiant I hoped. I even did do breakfast, Ian had told me what they liked, I did cereals, I did sausages and tomatoes and eggs and toast, I did coffee.

"Oh no, Mrs. Lyons, I always grill everything for Ian, have to keep his fat intake under control’ From her smile, I knew she was beginning to be won over, despite the legs. Legs? Yes, I had no choice. I had taken just a few select items to dress up for Ian the previous evening. So dressing down was difficult. The best I could manage was to wear less bright makeup, big gold clip earrings in place of the dangly ones of the previous night, Ian’s football shirt which at least covered my boobs though it was rather tight, the two round swells jutted out proudly, black leather mini and my black 6" stilettos. It was the best I could do!

As we prepared to say goodbye I was beginning to wish I hadn’t pulled the straps on my basque so tight. Just before they came down I decided on one bit of fun - I thought it was necessary, to prepare them for the ‘randy tart’ story Ian was going to spin. I heard them at the top of the stairs, grabbed Ian, threw my arms round his neck and kissed him hard. His parents came down with their cases, I kept hold, Ian’s hands which had tried to push me away suddenly grabbed my bum, I felt him slide his fingers down and onto my thigh. His mouth opened, I pushed with my tongue, we really were kissing!

"Sorry, you two lovebirds but we have to go". It was mother again, descending in front of father, smiling.

And just as we were at the door, the phone rang. When Ian answered it was his sister, trying to find her parents and wondering if they were here. Mother spoke to her for a few minutes, sounding disappointed. "Sorry Ian, but little Timmy has something spotty and maybe infectious. So Evelyn and Tom can’t make the party tomorrow night." She turned to me.

"I wonder, Sara. My daughter and her husband were going to go with us to a party at the castle tomorrow night. It’s a banquet really, you know, sort-of themed. We went last year, it was great fun. Victorian or Edwardian dress, men in uniforms or tails, ladies in flouncy dresses or hobble skirts. You would love it I am sure, how about you and Ian, would you like to come with us?"

A picture flashed across my mind, that tight leather hobble skirt I had seen in the sex-shop. It had looked gorgeous. With a white low-cut blouse, with... well, it would be fun.

I looked at Ian, trying not to give any indication. A totally neutral look.

Up to him.

"Well?" asked his mother.

 

3 - The invitation

He hesitated, he was flustered, I could tell. Part of him liked the idea, to be seen in public with a tart like me. But another part was more sensible, realised that doing this, with a GUY, well...

I had to answer for him. So I answered for ME

"That sounds wonderful! We would love to, wouldn’t we Ian!". He looked bemused.

"Err yes, its sounds, erm, good!" Ian answered. "Good, we will see you there then? Dinner is at Eight okay?" his mother stated.

"Lovely, we will look forward to it!" I answered with my arms wrapped around Ian’s waist. I held onto him as I watched his mother and father get into the car and drive off down the road. As soon as they had gone Ian turned on me. "What on earth do you think your doing, Richard!" he demanded, I released my grip and he pulled away.

"Don’t be so silly Ian. You said yourself only last night that I looked good, you even suggested we should go for a drink before your parents landed on us!"

"I know what I said, and I also know that they are my parents. What if they should find out?"

He was obviously quite upset. I tried to comfort him by once again putting my arm around him, this time he allowed it to stay in place. "Well, we will just need to make sure that they don’t find out, won’t we?" I kissed him on the cheek and walked back into the house. He followed me in and locked the door.

"Costumes?" he queried. "What are we going to do for costumes?" "Well I have seen something that is perfect for me. I am sure we can hire you something appropriate," I answered as I started up the stairs. I could feel Ian’s eyes following me, and as I neared the top I turned to see him with his hand on his crotch, trying to make his obvious erection slightly more comfortable. I simply smiled and asked in Richard’s voice. "Seen something you like, darling?"

He was looked shifty as though he had been caught looking up a school teachers dress.

"Sorry, Richard, erm, Sara? But you aren’t half a sexy little bitch" he retorted.

"Less of the little!" I answered with a mocking tone, and placing my hands under my breastforms. "These things can hardly be described as small!" We both laughed as he ran up the stairs after me.

After a brief discussion we decided that I should stay at his house and remain in character as Sara his ‘girlfriend’ until after the banquet. We had today and all day tomorrow to prepare for the party and we might as well enjoy it.

Today was Good Friday a bank holiday and so the chances of finding a hire shop open would be remote, so we decided that our costumes would have to wait until tomorrow. Besides today Birmingham were at home to Grimsby Town and we didn’t want to miss the game.

"Doesn’t that hurt?" Ian asked as he watched me take off my skirt and saw my faux pussy poking out of the top of my thong panties. "Quite the opposite actually. It’s like wearing a really tight pair of Kalvin Klein underpants. Once its all ‘tucked up’ provided I don’t get too excited. It’s really quite comfortable." I answered as I put my hand in my panties and poked one of my long red talons into my pussy. "Would you mind if I had a closer look?" he asked a little sheepishly.

"Would you ask a normal girl that?" I answered in a prim and proper voice.

"I guess not!" he was once again a little embarrassed. "Then you’re not going to be inspecting mine then!" I said as I pulled open a pair of ‘George’ sheer black body-shaper tights. Ian disappeared out of the room seemingly a little self-conscious, which bemused me a little. I pulled on the tights and smoothed them up my legs being careful not to snag them. I had these style tights many times over the past few years and they were among my favourites, as far as tights go that is. The control top prevented them from being tugged down as in many other Lycra tights I had tried. Yet my legs felt wonderful encased in the especially sheer and smooth nylon.

I decided that my short leather skirt was not going to be suitable for the match so I opted to keep the Rugby shirt and wear my old jeans. However I wanted to wear my basque underneath, as I loved the tight constricted feel it gave and it really accentuated my figure. I unfastened the suspenders from it and then loosed the laces of and slid it up around my middle. Then as before I took a deep breath and slowly pulled the laces tight and knotted them off. I pulled on Ian’s borrowed shirt again, then stepped into my Levi’s 501’s and eased them up my silky smooth legs. My waist had been pulled in so much that I had to use the last notch on my belt to keep them up, even then I could still get by hand inside the waist, but at least they were secure. I then slipped my feet into the 6" heels and went off to find Ian.

I found him in the bathroom stood over the toilet with his pants down, and by the expression and guilt written on his face I knew what he had been doing. I must admit that I found it very flattering and maybe slightly disconcerting that my lifelong friend had satisfied himself over me. He quickly pulled up his trousers and underwear and turned around. "Is that better?" I asked.

"Erm, yes much!" he answered.

"Good now get ready, its getting on and we have a lot to do." I told him. "My god Richard, you even look ‘hot’ in jeans now!" he said as his eyes devoured me.

"Sara!" I corrected him "Please don’t forget that whilst I look like a girl you must call me Sara."

"Yes, yes I’m sorry Sara!" he answered in a surly tone. I saw his eyes pass down my body too my heels. "You wearing them to the match?" "No they are hardly practical are they. I will be changing into my trainers before the game starts. I’m not too used to wearing high heels for any length of time."

"You really are ‘into’ this aren’t you?" he asked as he watched me flick my long curls back over my shoulder.

"If you mean, do I enjoy looking and feeling like this, then yes of course I do. I feel happy and contented as Sara. I feel like a different person when I am dressed up, I feel ‘comfortable’ I suppose." I tried to explain, but I got the feeling he wasn’t really listening. His eyes and concentration were once again on my breasts.

"For God’s sake Ian. Have you never seen tits before?" "Not a pair like those before!" he answered as his hands reached for them. I felt slightly detached as I watched him touching them, for I couldn’t feel anything.

"They are great!" Ian said admiringly. "And so lifelike." "Ian? Please!" I tried to remonstrate with him, as he massaged my huge silicone bags, he suddenly stopped as he realised his obsession with them was getting a little out of hand.

"Ian, you remember when I kissed you earlier?" I asked as I adjusted the position of my boobs.

"Erm yes!" he answered coyly.

"What was going through your mind? Did it ‘upset’ you." "Erm, well to be honest, it was kind of strange. It felt like it wasn’t Richard I was kissing, it was a girl, Sara, and well, I kind of erm ‘enjoyed’ it I suppose." He blushed as he spoke. "Good!" I simply said as I turned on my heels and walked off down the stairs.

 

4 - Shopping for England

I had never been out in public before but the past day had boosted my confidence so much that I hardly gave it a second thought as we strolled around like boyfriend and girlfriend. I felt cool, calm and utterly confident and Ian appeared to enjoy having a pretty girl on his arm too. We spent the morning in the supermarket doing Ian’s weekly shopping, whilst he went around the food aisles I shopped for a few feminine things in the clothes section. I saw a lovely skirt and top, which I really wanted to try on so I found the young assistant and took my heart in my mouth, and proudly asked.

"Excuse me, would it be possible to try these?" in my best girls voice. It was with a great sense of relief that she answered without appearing to give me a second look.

"Sure, the changing rooms are over their." she said pointing the way with a bright blue nail-polished fingernail. She was a cute looking girl and I quite fancied her.

"Thanks," I answered as I wiggled my way across to it. The skirt was short and box pleated, and fitted my constricted waist perfectly, and also showed off my long legs nicely. The top however which was metal blue, and a rouched material with a high neckline was too small around my more than ample bust. I stuck my head out of the door and caught the assistant’s eye.

"You wouldn’t fetch me a size 12-14 would you? I afraid this is just a little too small for me!" I said pulling at the taut fabric which was stretched over my chest.

"Sure," she smiled and turned away to fetch it. I meanwhile removed the one I was wearing, and placed it back on the hanger. Moments later a quiet knock on the door alerted me to the fact that she had returned. I opened it and her eyes immediately gazed upon my basque.

"Here you are," she said as we exchanged blouses, she then added "That’s pretty" her eyes were indicating toward my foundation garment.

"Thank-you" I answered, "it is isn’t it"

"I hope you don’t mind me asking, but is it comfortable?" she asked. "It’s just that although I have seen pictures in magazines, I have never met anyone who has actually worn one."

"Yes, actually it’s very comfortable" I answered with nonchalance in my voice, then added, "You should perhaps try one, one day?" "Umm, I might just do that" and then turned away and returned to her duties. I closed the door and leaned back on it, and took a deep breath, well as deep a breath as the basque would allow anyway. I had just had a conversation with a girl about my underwear! And she hadn’t even realised that it was a guy who was wearing it! My confidence was now sky high, the blouse was perfect and I decided to buy both it and the skirt. I changed back into my jeans and shirt, and went over to the till to pay. The young girl came scampering over to take them from me, and began ringing them in, as Ian came over carrying two large bags full of groceries. "Hello, sweetie" I said as I greeted him with a warm smile, "Did you manage to find everything?"

I was trying to belittle him a little and make him appear like an unwilling shopping partner.

"That’ll be £38.99, miss" the young girl said, meanwhile Ian was looking a little confused, and answered indignantly.

"Yes of course!" as I handed the assistant two twenty pound notes. I turned back to him and whispered in a loud voice.

"Did you remember my Tampax?"

I shocked him with the words meanwhile the young girl was fumbling for my change, and flashed him quizzical look.

"What?" he said somewhat flummoxed.

"Oh don’t say you forgot, you silly thing!" I was enjoying belittling him.

He quickly recovered his composure and rallied with a response.

"No, no. Umm of course I remembered."

I took the change from the girl and, gave her a knowing look and smiled as I took the bag from her and turned away. As we left the store, Ian spoke. "What on earth was that about, bloody Tampax?" she said somewhat angrily. "Nothing mate", I answered "just having a bit of fun, that all!" and laughed as I said it.

 

5 - Football crazy

The match was a boring 0-0 draw and was a complete anti-climax. However sitting in my seat dressed and feeling as I was went somewhat a long way to compensating for it. As we left however we stumbled into a work colleague of Ian’s.

"Who’s this?" he asked introducing himself as Dave. Ian was quick to appear calm and unflustered.

"Dave this is Sara. Sara, Dave" he said formally introducing us to each other.

"Did you enjoy the game?" he asked, in a tone, which meant did you understand or follow it?

"Apart, from that first half missed penalty, and the continual way they played the offside trap?" I answered.

"Umm, yes" he seemed confused by my ‘knowledgeable’ response. "You seem to know your stuff!"

"I get by, oh their number eight was gorgeous too, he had nice legs and tight arse!" I added in a girly manner. He stood expressionless for a few seconds then began to laugh. And turned to Ian and said as though I wasn’t there.

"Good sense of humour your girlfriend here!"

‘Girlfriend’! I smiled at Ian.

"Yes, she’s all right" Ian said placing his arm around my shoulder, as we walked away into the crowd.

"What a pratt!" I said.

"Yes he always has been!" Ian answered, once more we both began to laugh. Back home I took on the part of the dutiful girlfriend and made Ian some tea, nothing exciting, just something to ease the hunger. I had kicked off my heels as my feet were killing me, and as me sat watching TV with our trays of food on our laps I wiggled them trying to get some circulation back. The iridescent pink nail varnish I had on my toenails was easily noticeable through the black nylon that enveloped my foot. And I noticed that several times Ian glanced over to look at them, he appeared to admire them as much as I did.

"Fancy going to the pictures to see ‘The Blair Witch Project’?" Ian suddenly said, as he took his tray back to the kitchen.

"Yes, sure. That would be really nice" I answered. It sounded like he was asking me out on a date. "I’ll just nip upstairs and change" Minutes later I was refastening the suspenders to my basque and pulling on a pair of pale grey glossy lace topped stockings up my legs. I squeezed my slightly swollen manhood into a pair of tight black panties, then I took my new blouse and skirt from the shopping bags and broke off the plastic price labels and slipped them on. They, in conjunction with my black stilettos, looked knockout and made me feel fantastic. I then teased my hair into shape and touched up my makeup.

This time I chose to slightly overdo my eyes with heavier black eyeliner and lashings of mascara, my lashes felt slightly sticky as I applied the second coat to them, but they looked terrific. I took a out a new red lipstick and stroked on a layer onto my lips, and rubbed them together to spread it evenly. I felt excited and in no doubt about my appearance as I carefully walked down the stairs to be greeted by Ian.

"Well? How do I look?" I asked waiting for a compliment, I was not to be disappointed.

"Richard, you look absolutely stunning!" he said as his eyes scrutinised me, "I mean Sara!" he corrected himself.

"Come on lets go!" I said as I grabbed my coat and slipped it on over my shoulder. I then lifted my long hair over the collar. The Multiplex was busy but we managed to get good seats and a huge tub of popcorn in plenty of time before the film started. It didn’t take long to become absorbed into the movie and begin to relax into the surroundings. It was sometime before I even realised that Ian had his arm over the back of my chair, however as soon as I did so I eased myself into his comforting embrace. In turn I placed my hand onto his thigh and occasionally slowly stroked it.

The film was totally absorbing and we were both thoroughly enjoying it. At one particularly scary part I made Ian jump as I dug my long nails into the inside of his thigh.

Although it was a very popular film, several seats around us had not been filled. So on impulse I lifted my left leg and placed it over Ian’s, I was half expecting him to object, but he didn’t, in fact I was rather surprised to feel him lay other hand on my thigh. He even appeared to be keen on the silkiness of my stockings as he continually stroked them. I realised he was getting a hard-on, and decided I had to find out more about the effect of being a girl, on men. Just in the cause of research, of course.

As the film was nearing its conclusion I finally plucked up courage to place my hand on his crotch. I got no reaction from him except for a slight tug on my shoulder, which pulled me in closer to him. I decided to take that as a sign of approval. My elegant long-nailed fingers moved up to his zipper and I took hold of the fastener and very slowly pulled it down, still I felt no objection from him. My hand then felt its way carefully into the opening and found a huge erection waiting for it. I found the top of his shorts and with my thumb and index finger eased the top of them down until I could feel his excited cock. My fingers pulled his foreskin slowly back and very slowly and very gently my fingers caressed the sensitive skin which was exposed. Ian was now shuffling in his seat. I could hear him breathing rather heavily and sensed that he was almost at the point of having to cum. I dug my long nails slightly into the hypersensitive flesh and with a sudden movement I feel hot gooey cum trickling across my fingers. My job done I tucked him back into his shorts and silently zipped his flies up and settled back to watch the closing stages of the film. Not before I had lifted my fingers to my lips and tasted cum for the first time.

He was very quiet on the way back, and although we spoke briefly about the film neither of us mentioned our sexual encounter or feelings that had been exposed. It was as though our mutual embarrassment and progressively prolonged avoidance of the topic prevented it.

As soon as we got into the house Ian immediately disappeared off to his room, after saying a polite ‘goodnight’. I meanwhile sat watching TV with a glass of wine, reliving the events of the day in my mind, after all it had been such a good day!

The following morning I awoke early and prepared myself before Ian had even stirred. I had gone into the bathroom as Richard, but came out as Sara again, and it felt even better than before, for today was going to be an even better than yesterday.

Once in my ‘dressing room’, I put on a pretty deep blue bra and panty set followed by my favourite sheer black tights topped off with the black leather skirt and a tight white T-shirt which showed off my tits to perfection. I toned down my make-up from the previous evening and just applied a light layer of mascara over still quite heavy eyeliner. Eye shadow was quite in subtle tones of grey and blue, with silver highlights around my brows and cheekbones. Lipstick however was loud and very brash in a deep vermilion red. I felt like a vamp when it was complete and I knew I looked good.

I slipped on my stilettos and went round through Ian’s room. It was now nearly 10am but he was still in a deep sleep. I took hold of the curtains and pulled them open quickly letting in the bright morning sunshine. He immediately awoke and complained at the intrusion and the light, which apparently was burning holes into the back of his head. He was lying on his back with the sheet pulled up over his head, I took hold of it and with a single sweeping movement I through it onto the floor. And his huge erection greeted me.

"My, my that’s a nice greeting!" I commented as my eyes feasted upon it.

"Richard!" he complained. "Please don’t!"

"Don’t what?" I protested.

"Please don’t make me feel so," he paused before carrying on "well, so awkward about this" "Ian" I said sitting down on the bed. "Look this is awkward for us both. Just because I like to look and feel like a girl and you find me attractive does not make us raving homosexuals. We just have to take these experiences as they come, and not worry too much about what the social conventions are. When I am Sara I feel like I am a girl and not Richard in a dress. You obviously see me as Sara and not Richard, so why don’t you just relax and enjoy what we have, and not feel embarrassed and awkward by it." With those words echoing in his ears my hand moved across to his still quite firm erection and I began to massage it. This time he didn’t protest he just closed his eyes, and appeared to enjoy it. I knew what I just had to do. I bent my head down and my hair fell forward obscuring my prey. With my spare hand I held back my long blonde curls and kissed the tip of my best friends cock very gently, leaving a slight lipstick smudge on it. I looked up to his face, this time his eyes were open and he simply smiles at me. "Okay with this?" I asked.

"Just fine" he answered, eyes wide apart, puzzled but thrilled at the same time.

I returned to his cock and in one movement I opened my mouth and began to take him into my moist mouth. Slowly at first then gradually faster I eased it deeper and deeper into my mouth. I could taste his salty pre cum as his excitement grew, I knew that he wouldn’t last long but I wanted to savour the time. It was however too late and he suddenly burst into my mouth as I heard him say "Christ!!"

I continued to suck and swallow whilst he pumped his sperm into my mouth, he seemed to take a long time before his body relaxed and his raging erection suddenly began to go limp in my lips. I pulled away and wiped my lips on the back of my hand, and pushed the last of his salty cum back down into my throat.

"I’m really sorry about that," he said in such an apologetic voice. "Don’t be," I simply answered as I stood up and went to the door "Breakfast in twenty minutes" I said as I left his room.

We arrived at the sex shop at about noon, Ian was very nervous about going in but I soon persuaded him. The interior was dark and all around the walls hung racks of fetish clothing, mostly black PVC or leather with the odd bright red outfit. There was no one else in the shop, and so I went to find the owner whilst Ian began to look around. I found a bell on the counter and gave it a quick tap, which turned into a loud ring, within seconds a middle-aged woman with several facial piercings came through a door behind the counter.

"Good morning, can I help?" she asked

"Yes, when I was here a couple of weeks ago I saw a dress which I would now like to try on if I may?" I answered.

"Okay can you describe it?" she asked as I noticed the intricate Celtic tattoo on her arm.

"Well, it was black leather," I almost giggled at the obviousness of those words, "Ankle length with a lace fastening at the back, high neckline almost like a collar and long cuffed sleeves, I think it’s described as a hobble dress" I said the words with confidence and no embarrassment. "I know the one you describe," her face lit up "I’ll just go in the back and get it" with that she disappeared through the door again. I turned to find out what Ian was up to. I saw him at the other end of the shop looking through a whole rack of vibrators and other erotic objects. The woman reappeared carrying the dress I had seen before. "This one?" she asked.

"That the one!" I replied.

"Would you like to try it on?"

"I sure would" she led me over to a changing cubicle, and I called Ian over to help.

"Is it okay for my boyfriend to help me into it?"

"No problem, just give me a shout when your ready." she answered. I took off my blouse and skirt, whilst Ian fumbled with the lacing in the back of the dress. When he had loosened it I took it from him and stepped into it, the first thing that struck me just how narrow the bottom of the dress was. I slipped my arms into the sleeves then up onto my shoulders, it was immediately apparent that although the size was about right the bodice was going to be far to small for me. I called for the owner, and she quickly appeared.

"I think I am going to need a corset with this, you have them?" I asked "Sure do, honey, I’ll just go and get one that will be suitable" she answered with pound notes in her eyes. I stepped out of the dress again admiring the soft suppleness of the leather. It took a couple of minutes for her to reappear, but when she did she had brought a black leather corset. "I am sure that will fit you!" she said as she handed it to Ian, who quickly passed it on to me.

This corset was more heavily boned than my basque and would not support my breasts, so I would need to wear a bra with it. It was laced at the back and I could hardly wait to try it on. I undid the laces loose enough for me to be able to step into it and squeeze it up over my thighs and bottom. Then with my instruction Ian began to tighten the laces and the corset started to pull me in, after much tugging and heavy deep breaths he tied it off. I had no means to measure my waist now but it was certainly much smaller that it had ever been before.

I then tried to bend over to step into the dress again, only this time it was much more difficult. The fit seemed was much better, and Ian managed to lace me into it without problem. The collar and cuffs closed tightly around me and the fastening looked like it would take a small padlock, which excited me.

Ian opened the door and I attempted to walk out of the cubicle. The dress would only permit me to take small stimulating steps, so the journey over to the mirror took quite a time. However once I stood it front of it and saw my refection I was even more staggered. The corset and dress felt amazing but it looked even better. I was sheathed neck to toe in black leather, which clung to my body like Clingfilm. My tiny waist accentuated my breasts, which now looked even bigger, and my hips much more feminine. It was even better than I could have dreamed about, I turned to Ian. "Well what do you think?" I asked.

"Fucking fantastic!" was all he could say.

"You look amazing in that," the owner said as she came over.

"I’ll take them both!" I said to her.

I then regrettably had to go through the reverse process of taking my new dress off, though it was much quicker than putting it on. Even for the short time I had been wearing it, the relief of the loosened corset was huge. Once back in my own clothes, we looked around the shop for some accessories. Ian found some tiny padlocks, which would effectively ‘lock’ me into my hobble dress. I found some American nylon stockings, which had seams and cuban heels, a matching black leather bra and panty set, and a pair of fingerless black lace gloves. I also noticed a ‘Betty Page’ style raven black wig, which would suit the dress far better than my blonde locks. Ian surprised me when he told me he would buy the entire ensemble for me as a gift. I left him with the pierced lady to pay for and wrap the things we had selected, whilst I went up the street to Boots and bought some black nail polish, for tonight I was going to be the first ‘Victorian Goth’. The rest of the day, I spent in seclusion preparing myself for the night ahead. Ian meanwhile had instructions to go and hire a Edwardian morning suit, such that he could pass for Dracula on any other occasion. The taxi was due to collect us at half past seven, and so it was about an hour before that I began to paint my nails and apply my makeup. Stroking on the glossy black varnish onto my fingernails was a truly erotic experience. The contrast between my pale flesh and the jet-black polish emphasised my long nails and delicate fingers.

Ian came in to help me dress, he looked very sophisticated in his long tailed coat and wing collared shirt with frilly tie. "You look amazing, Sara." he said as he saw me stood just in my underwear and new black wig. I was thrilled that he was pleased and also that he was now starting to call me Sara without even questioning it. "And you look very handsome!" I repaid his compliment. I was stood with my back to him in my leather bra and panties, with the corset already loosely fastened around my waist. As before he took hold of the laces and began to pull them tight, this time I swear it was even tighter than before by the time he had knotted them off. My waist was so constricted that I could hardly bend, and Ian had to help me roll my stockings up my legs and fasten them to the six suspenders dangling from the corset, which he seemed to relish. He then guided my feet into my 6" stiletto heels, and at my prompting checked my stocking seams. He then surprised me by revealing a number of additional ‘gifts’ he had purchased. First was a diamante tiara, which he placed carefully on my head, then a matching bracelet and necklace, which he also fastened into place. "These are wonderful!" I said as I admired them. "They must have cost a fortune?"

"Actually surprisingly little you would be amazed at how cheep faux jewelry is these days" he answered, before adding. "Err I also have another gift for you" This time he seemed a little bashful, as he took out of a bag a small vibrator. I say small but it must have been about 5" long and about 1 ¼ inches in diameter.

"A dildo?" I questioned.

"Actually its more than just a dildo. It’s a radio controlled vibrating dildo" he proudly explained. "I thought you might like to experience the occasional burst every now and then?"

"Wow, I’m not sure" I had to admit. "I guess you’ll have the transmitter?" "Of course, but if you would rather not try it. I will understand!" Ian said as he began to put it back into the bag.

"No!" I remonstrated. "Let me try it"

As if he was already prepared Ian took from the bag a small jar of lubricant, and proceeded to smear a liberal quantity onto the vibrator, then he motioned to hand the jar to me.

"You do it please" I asked as I eased my tight leather panties, down my thighs, and presented him bottom.

He gingerly at first dabbed the gel onto the rim of my anus, then as he got used to it actually probed it slightly. When he was confident that I was adequately lubed he slowly pushed the dildo into me. It slid in without causing any pain or discomfort, and actually felt quite satisfying. I pulled my panties up again, which prevented it from coming out again. "Well how does it feel?" He asked.

"Delightful!" I simply responded. "Now help me into my dress the taxi will be here soon!"

Freedom of movement was now quite difficult, my corset was bad enough but now the dildo had made things a little worse. However after some struggling we managed to get the dress into place and Ian laced me securely into it, before taking the three gold padlocks and snapping them closed onto the back of my collar and two cuffs. I was now helpless and without Ian I could not get the dress off, nor get at the dildo.

"Are you really sure about all this?" Ian asked me, as I grabbed my bag, ready to leave with him. The taxi had just arrived. "Why do you ask?"

"Well Richard - er, sorry again, Sara. "Barely 48 hours ago it was just a bit of fun, at least that’s what I thought. You know, you getting dressed up at my place, me the audience, telling you how you looked, encouraging you, a bit of a strange hobby I thought but it didn’t do anybody any harm. And now, well, you looking like that, honestly, a total fucking tart, you look incredible, you really do. And you - well - sucking me off, and all, and my mother thinking we were sleeping together. Is it all too much?" "What do you think, Ian? Didn’t you like the blow job?"

"No, really, it was stupendous, looking like that I can hardly see Richard.

In fact I can’t, you are totally female to me. But what is it with you?" "Well Ian, I have to admit, I was terrified when your parents walked in and assumed I was - what they saw. But I have warmed to the idea. I always wondered what it would be like to be a woman, and now I am finding out. It is fun! I just love looking like this!"

"Well. Sara, I have to say I like you looking that way too" grinned Ian. I couldn’t help it, I just flung my arms round his neck and kissed him.

 

6 - Party time

The taxi came, I ‘hobbled’ out to it, Ian struggled to walk too, he had suddenly got a real hard on, I could tell! At the Castle we were set down just outside the main entrance, good job too, I really couldn’t have walked far. Just as we went it I got a taste of what was to come. I took a sudden sharp breath at the vibration in my arse, Ian had turned on the dildo to give me a quick blast.

"Just wanted to see if it was working. I can tell it is" he smiled. We saw Ian’s parents straight away, his mother came over to get us, obviously unsure about this suddenly. She had seen my outfit, obviously, and I am sure considered it extreme. It was! Black leather, really tight, with the bondage padlocks and gold buttons, and the makeup, deep red lips outlined in black, extreme black eyeshadow, the black nails. "Sara my dear, you have really gone all out haven’t you. What a costume, I hope that skirt isn’t too tight, it looks a mite uncomfortable" Well, it was really, very restrictive but that was part of the fun of it. I tripped carefully across to the bar, and was joined by Ian’s father as mother fussed over her son, straightening his tie, maybe having a few words about his choice of girlfriend. I had tried the previous morning to overcome the ‘tart’ image but, this outfit was reinforcing it again. And I was rather surprised, as we stood at the bar, to find Ian’s father’s hand on my bum. It was there, it was pressing firmly, it was squeezing just a little. Dirty old man! But then I thought again, why not? I was obviously flaunting myself, maybe he regarded my attire as some sort of invitation. Anyway, I was enjoying the attention!

To be honest the so-called banquet was a bit of a disappointment. All image and no substance, fancy plates and serving wenches, but the food was not very good. It was maybe just as well, I certainly couldn’t eat much, I was feeling so constricted in that dress. I took Ian’s arm as he led me away from the table and into the bar again.

And it was then the fun really started! Well, not really fun, it started out uncomfortable, got painful, at one stage very painful, and ended up in glorious relief!

I just about managed to perch on a bar stool, legs side by side, the leather dress stretching to really show off the shape of my thighs and bum. Two or three of the guys nearby noticed, well, they could hardly help it, my legs smoothly covered in glistening leather, my ultra-high heels provocatively on display. I swivelled a little but Ian was gone, I spied him chatting to another man at the other side of the room.

It was Adrian! His ‘twin striker’ in the team! I was aghast, he mustn’t see me. But too late, he had, they were both heading in my direction, making their way through the throng. I had to think quickly, to use whatever means I could not to give Adrian any clues as to who I was. I turned to a man next to me at the bar, a rather young man, probably thought rather dishy by young women. He seemed on his own and was just getting served.

"Hi there, my name’s Sara"

He looked me up and down. Then up again, his gaze resting on my breasts. I breathed in deeply, allowing my bosoms to swell, almost busting out, surely he had to be interested. He was.

"My partner has left me all alone, how about a drink for a lonely lady?" I asked in mock misery.

"Sure" he said, turning towards the bar again.

"And I really could do with a cigarette, please?" He complied with my request, I inhaled deeply and pushed out my boobs again as he lit it for me. That might put Adrian off, I didn’t smoke as ‘Richard’, just thought it added to the picture as Sara. I took his arm and slipped off my stool.

"Let’s get some air" I said, picking up my drink and my bag and heading towards the large French windows which led out into the courtyard. By the time Ian and Adrian got near the bar we were well out of sight, appreciating the cold night air.

My partner smiled as he turned towards me.

"Well, lonely lady, let me introduce myself, I’m Clive. I couldn’t help notice what that was about. Someone you were trying to avoid?" I looked across at him - hell! I was surrendered by bloody footballers. It was the number eight, the Grimsby player, the one with the nice legs and arse. I blushed - under the makeup he must have seen. "What’s wrong?" he asked. "Something I said?"

"Oh no" I replied, rather embarrassed. "It’s just - I saw you this afternoon, at the match. I thought you would have all gone, you know, on the team bus. Back up to Grimsby."

He smiled. "Oh, I see, well, usually I do but my Mother is in Brum, so I took the chance to visit. Then she offered me her tickets for this do, so I came with a mate of mine. He got off with a blonde as soon as he came in. So right now I’m on my own. Or was ‘til now" He smiled at me - suddenly I was very wary. This was a fit young man, doubtless with a healthy sexual appetite, looking at me in a very desiring way. His mate had got off with a blonde, I was in no doubt at all that he wanted to ‘get off’ with me.

So why did the idea excite me? I was just about to make a move - I had to ‘go’ one way or the other, when he effectively made the decision for me. Out of site of the bar and the banqueting hall he slid his hand up my thigh, breathing in deeply as his fingers moved over the soft thin leather. I sighed too - not just because of that, but also because of Ian. I felt a sudden sharp pulse in my arse - he had given the dildo a quick burst. I wanted to turn and see where he was, and to flash a dark look at him, but I didn’t get the chance. Clive was suddenly all over me, burying his face in my neck, his hand now snaking up over my waist to caress my left breast. It heaved as I squirmed and reached up, to caress his head, to run my long black nails down his cheek. I moved my lips towards his - then Ian did another blast.

I managed to turn and see him - and glare, but he was just grinning, standing with Adrian, with his hand in his tunic pocket, obviously on the control. I had to get away, to stop him, he was ruining things, I was beginning to feel really horny, I was turning Clive on. And his attentions, and the buzzing in my arse, were turning me on. But I managed to get his hands off me, then to stand, wobbling a bit on my ultrahigh heels, and started over towards Ian.

"Won’t be a minute, darling" I called to Clive. I got over to Ian, desperately hoping that Adrian wouldn’t recognise me. I needn’t have worried really, the smooth shining figure, the provocative makeup, the bulging boobs, no way was I in any way resembling his mate ‘Richard’.

"Ian, my dear, I need a word" I hissed, grabbing his arm and pulling him back into the bar. "What the fuck are you playing at, stop it, will you, turn the fucking thing off and leave it off. Better still, give it to me. NOW!" I rasped, staring to show I meant business. He reached into his pocket and took out the small control box and held it out. It was the nails, the very long black-varnished fingernails, I just wasn’t used to them, I fumbled and dropped it. I gasped, hoped no-one would see. But of course absolutely no-one would realise even if they did. Ian was apologetic, he bent over - I couldn’t in that dress, and picked it up. As he did hand it over I realised it was on and operated the switch. Nothing happened. It was still on! I pressed again, several times. Maybe I was doing it wrong, I handed it back to Ian.

"Turn it off, it’s still on, it won’t work!!" I almost cried, it was not on the fast setting thankfully. But it was on!!. He fiddled with the controls several times, looked across at me, he could tell the control was not working.

"Sorry Richard"

I hissed at him, annoyed he was so cool about this. "Don’t call me Richard, not here, not now, silly, look you have GOT to get this sorted, can’t you take out the batteries or something?"

"Sara, I will never be able to get at it, you will have to take the dress off. Can’t we go in the loo or something, maybe I can do something there?" "Stupid, which loo, they are both busy, neither of us can sneak into either. And there’s not enough room in a cubicle, I need space to stretch to get this dress off. We have to go home. Mine, yours, anybody’s home." Though we were being quiet in our hissings and whisperings, it must have been obvious we were having a disagreement of some sort. Ian’s father was hovering near, waiting to interrupt, he butted in "Now then, what’s this, a lovers’ tiff? Take it easy you two. I am afraid I have a problem, mother is feeling unwell, she had had a little too much to drink. We are going to have to go, thanks very much for coming you two. Don’t stay too late though, will you?"

"Oh Mr. Lyons" I piped up. "I am so sorry, but we also have to go very soon, I have to be up and about tomorrow, family things you know." "OK. Our taxi should be here any moment, why don’t we share, I am sure mother won’t mind."

I jumped at the chance, this would be by far the quickest way to get things sorted. The dildo was still throbbing in my arse, not painfully really but I was beginning to get extremely aroused, my cock was uncomfortable now, I could tell things would soon become painful. We all piled into the taxi, in fact sitting down helped after the difficulties of getting into the back in that skirt and those heels. I tripped a little as I got in, fell towards Ian’s father, gave him another pleasant surprise as he reached out to help me and caught my left tit!

Things were going OK, I was coping, I could see an end in sight. Until the taxi stopped and the driver turned round.

"Sorry folks, just heard on the radio, a lorry had jack-knifed on the bridge, I can’t get over the river. Looks like a long delay. OK with you?" It most definitely was not. Ian’s dad made the suggestion, I wouldn’t have considered it normally but these were dire circumstances. "You could come and stay with us for the night. Then try to get over the river tomorrow. How about it?"

It was the only solution, the taxi managed to turn round, we all poured out at Ian’s parents’ house, mother dashed to the loo. Ian quickly showed me to his old room where presumably we were going to sleep. He had my little case with him, with emergency male clothes and - more importantly, the keys to my padlocks.

By this time I was getting desperate. Ian was too, in a different way, his pants were tight, the selfish sod got me the key, handed it over, and then proceeded to concentrate on getting off his own boots and trousers! I couldn’t manage the locks and the key, not with the long nails and in my extremely agitated state. My arse was pumping, almost literally, as the vibrating dildo, which must have had long-life batteries, throbbed away. I was sweating, the tight corset and the extremely tight dress did not allow easy access to the locks.

"Ian, you fucking arse-hole, come on, I need help, I am going to explode" He did help, standing there in tunic top and pants, his own cock making a very large tent at the front, but he did manage to undo all the locks quickly, we then together set to the task of undoing all the gold buttons down the side and easing the zips. Finally after two of three minutes struggling we managed to slide the whole dress off in one go. I breathed one sigh of relief. Then, bending over and reaching into my panties, I got hold of the end of the dildo and pulled it out, dropping it on a towel. My arse was so wide, loosened by the continued activity for nearly an hour, I just gasped with the luxury of freedom of movement down there. But. All was not totally well. My own cock had been restricted so much it had not been able to expand. Whatever hormones had been pulsing round down there hadn’t been able to do their job, I felt physically very relieved in one sense but there was still a vast sense of unease, something else was needed. I looked over at Ian.

He was just staring. At me. I realised that in bending over I had given him a full-frontal view of my ‘breasts’, that he was staring right down the chasm of my substantial cleavage, bulging in the black leather bra, and that it was having an effect on him. He was in many ways a normal, red-blooded male, with normal desires. He had to ease his pants, as he did so I saw his cock, huge, erect, slightly throbbing itself. At that moment I was a woman, turned on by all the sexual activity of the evening, still excited, still horny, in fact - desperate for it. I didn’t hesitate. I pushed him over onto the bed and climbed on top of him, leaning over to press my lips against his.

 

7 - A woman at last

"Christ, Sara, you really have got it together, you are a real woman" I didn’t reply, just reached down and grabbed his cock and squirmed, settling the head against the entrance to my ‘cunt’. He squirmed himself, realising what was going on, and started to speak. "Sara, wait, we can’t..."

"Like fuck we can’t, come here my lovely gorgeous one, I need you up me - now!" I replied, leaning over and pinning his arms to the bed to hold him, attacking his lips with mine, and lowering my ‘cunt’ towards him. "Christ, Sara, what are you doing, we can’t, not here, not now" I was so loose, so hot, so lubricated. I felt him buck, resist, try to get out of it. I am not enormously strong but in that situation, in that position, he couldn’t compete.

I slid up and down, he squirmed again, then stopped. His tongue entered my mouth, NOW he was enjoying it. I had started out to rape him, but he was now a willing partner. I released his arms, they slid round my back as we rolled over. I smiled up at him, spread my legs wide and reached up to accept his enlarged cock into me. He fell on top of me and thrust himself into me simultaneously For an instant, I was face-to-face with Him. His eyes were glazed over, his breathing heavy and his shirt was open. He pushed me strongly, staring down at my body below him, lust in his eyes! I cried out as he penetrated deeper into me. The feel of his enormous cock inside immediately returned me to the ultra-aroused state I had been in before, and more. He pumped furiously in and out of me. My legs wrapped tightly round his waist, pulling him deeper into me. My long black nails clawed hard into his back as his thrusts penetrated deeper and deeper.

Our animal-like movements became uniform and fluid as I thrust up in exact rhythm to his downward thrusts. Our primal instincts had taken us over, pushing us to physical pleasure. His tempo changed and I knew he would cum soon. My body adjusted to match his. I was now on the threshold as well and felt myself tightening around him.

We kissed again, passionately, our tongues both exploring each other’s mouth, our bodies hot and smooth, gliding together as we move din unison. Suddenly, he gave one final thrust and his body stiffened. I felt his hot creamy liquid pulsing into me as he let out a long, satisfied moan. Almost simultaneously, my own body erupted into a screaming orgasm too! After what seemed an eternity we both lay there for a moment, gasping for air. I opened my eyes and looked up at him, feeling the post-orgasmic afterglow surround me. He lifted himself up slightly and slowly began to withdraw from me. I was deflowered, no longer a virgin, but I was somewhat surprised to see that he was still far from limp. Before I could say or do anything, he thrust his still hard cock back into me! My sensitive nerve endings screamed in both pain and pleasure as he hammered me again! Another orgasm quickly built up... and exploded within me!

He was working like a man possessed.

Pushing himself into and through me...over and over, my body gave a final, violent shudder.

"Ssshhhh" I whispered, pressing my lips to his to keep the noise down as we subsided.

"Sorry, I am so sorry, it’s just you looked so provocative, so foxy! Sorry Richard" "Don’t call me Richard!" I hissed again. "And anyway, I started it, I was so turned on and seeing your bulging knob, there was only one way out. So how was it for you?"

"One hell of a fuck!!" he moaned.

I got myself out from under him and undid the waist cincher, then clad only in my leather bra and panties and stockings, and a shirt over the top, I dashed to the bathroom and cleaned myself up. I took off most of my makeup and swapped wigs, Ian’s parents had me down as a blonde who had worn a wig for the do. As I slipped back to the bedroom Ian’s father was just coming up the stairs. I couldn’t help it, the shirt flapped open to reveal my sexy undies.

"How is Mrs. Lyons?" I asked politely. I couldn’t help noticing he was staring at my bulging boobs and to be honest I couldn’t blame him. "OK now, I think, just needs a good night’s sleep. Sleep well yourself" I don’t think he realised any of what was going on, obviously not the details but I am sure he didn’t appreciate his son had just fucked me. "Oh good, well, goodnight" I muttered and slipped into Ian’s room. When I woke the next morning I realised the problem I had, I got in the bathroom again and redid my makeup, smoothed my face and so on. I also managed to swap my nails, the black/violet goth was gone but I only had long red ones with me. With those and the high-heels I was still promiscuously dressed. Luckily Ian’s mother was aware, realised I couldn’t wear THAT dress, she found some older stuff of her daughter’s which fitted me. The skirt was too short, even for me, but the sweater was OK, the ensemble didn’t look too bad.

 

8 - Caught out - in a way

The problem occurred after a brief breakfast, when Evelyn arrived. First to say Timmy was better, it was in fact not contagious. And secondly to meet Ian’s girlfriend!

She didn’t mind me wearing her old clothes, in fact she was very friendly. And I was very nervous! Passing at a party, with lots of people around, dressed up etc was one thing. But here I was in close proximity to a woman my age, who was treating me more like a friend, a sister, whatever. It got really difficult when we got left alone!

Ian and Dad had to shoot off, the car was still causing problems and it needed the two of them to go, to arrange something with a mutual friend, Gareth, who knows everything there is to know about Volkswagens. And mother went out to visit a friend of hers whose daughter had just brought her own daughter to visit. So Evelyn and I were on our own. "Sara, please, I am very sorry I couldn’t go to the party last night but I am delighted you and Ian could. Now I must see the dress you wore. Mother says it was something special."

I had to show her. I was getting more and more nervous, I had to explain the more extreme features, the zips, the gold buttons, the padlocks... And it got worse.

"OK Sara, it looks my size, is it a 10? Good, I just MUST try it on." With that she stood up and pulled off her sweater and slid down her jeans, revealing - to ME - a very shapely body. And she insisted I help her with the dress and posed for a few minutes, looking in the mirror and flaunting her figure. Then she asked me to go downstairs to make some tea, which I did.

It was ten minutes before she reappeared. I had just finished getting the tea ready, not sure what would be coming next. Then Evelyn came in. I gasped.

She was totally encased, head to foot, in what I can only describe as a full-on dominatrix outfit. Black PVC basque, and thighboots, laced tightly, very high heels. And the makeup was heavy, dark, foreboding. Black choker too, and wristbands, with the severe makeup and jewellery, she looked, in a way, frightening. I wasn’t sure what to make of it, but she didn’t care, she was in ‘domme’ mode. She came over towards me, gabbed my breasts to pull me towards her, and kissed me - hard!

"Well, Sara, you can see, you’re not the only one who goes in for this sort of thing. My friend Jacqui and I have enormous fun dressing to please, sometimes. Pity we have no time now, mother will be back soon. She doesn’t know about this lot, it’s in a case under the bed in my old room. Now then, Sara, what are we going to do with you?" I was puzzled, didn’t realise what she meant. Then - I saw the look in her eyes. Did she know?

"You are good. I mean it, REALLY good" she said. She did know! "I’ve always known Ian was a bit of a wimp. But I didn’t know he is a faggot too. Does he fuck you? Up your arse, maybe? Those are extremely impressive tits, I will say that, you are probably the best transvestite I have met, really, I have several friends who would LOVE to meet you. And fooling Mum and Dad, too. I wonder how you have the nerve. So tell me about it." I just had to. Tell her. About being caught out, pretending to be Ian’s girlfriend, the dressing up, the wank in the cinema, the party, finally about having sex in Ian’s room.

"Wow!! You really have got it all together. Now. Hear this. There isn’t time today, and I do want to have a word with my best friend Jacqui. Whoops, better change."

She dashed upstairs as we heard the back door open, Ian and Dad came in having sorted the car, properly they hoped. Mother appeared too via the front door, we all had tea. They were all chatting, I was worried. What had I been let in for?

Evelyn came down, redressed in jeans and top, smiling.

"You are lucky, Ian. With Sara, I mean, we have got on so well together". She hugged me and kissed me, on the cheek this time, steered me out into the garden.

"Right Sara, or whatever your name really is. Listen. Next Friday evening, 5.30, outside the entrance to Boots on the High Street. You had better be there. Dress tarty, really tarty. You know, the promiscuous secretary look, incredibly short skirt, with black stockings and ultra-high heels, you transvestites like that don’t you. And don’t even think of not being there!" She turned and left to go back in, apparently said quick goodbyes and left. I did too a few minutes later, Ian borrowed Dad’s car to run me home. He probably wondered why I was so quiet.

I got in, poured myself a gin and tonic, and sat in the armchair, legs crossed, thighs exposed. Thinking. Just what had I got into?

The end?

 

 

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