by Caroline Jane Bradley
His first girlfriend, Julie, used to encourage him to wear her knickers and sometimes her night-dress when they made love in her small bed-sit in Clapham. He loved the feel of the lacy nylon as they rubbed against each other in mutual pleasure. But time passed and Julie left for a job in the Midlands.
Eventually, Steve's career as an office designer took off and before long he had met, and married, Joanna. His job helped fund her through the last stages of Business School and her frequent absences from home on weekend course work enabled Steve to gently re-acquaint himself with the gentle feeling of release and calm when he slid into her underwear and dresses. Steve was fairly big, so few of her things fitted well and by careful purchases in the guise of birthday and Christmas presents, he had built up a small wardrobe of his own "things".
He has tried to carefully instill wearing her night-clothes into their lovemaking, but Julie would always say that she only wanted to make love to Steve, her man, not some girl. He loved Joanna dearly and was very proud of how well she was doing at School, so his dressing up escapades were kept to those few moments when she was late home.
After graduation, Joanna got a job as a Financial Analyst with a big firm of London stockbrokers. Everything was going well for them and they didn't want Children yet as her career was really taking off. Steve's job was also going well, but he really missed the opportunity to dress up, it seemed that, when he managed to snatch one evening "en Femme", his desire to repeat it and go much further increased. Joanna seemed blissfully unaware of his needs and was totally focused on her job.
Two years after Joanna's joining the London Stockbrokers, she was "recruited" to join another firm. She announced her new salary and they went out to the most expensive restaurant in their neighborhood. During the meal, she told Steve that the new job would mean she might have to be away for extended periods, especially in the next few months, but that it was all worthwhile for their future together. Steve expressed his undying support for Joanna and her career, but secretly was delighted as he started to think of all the opportunities of spending time in his favorite short black skirt and creamy blouse.
A few days later, Joanna calmly announced that she had to go off to the USA for a 3-week tour of her new Company's subsidiaries. because the itinerary was so tight, it would not be possible for her to get back to London during that period and, as she was to be working most weekends, it would be impractical for Steve to fly out to join her. Steve immediately began to plan how he could best use this opportunity!
During the weeks leading up to Joanna's departure, Steve increased his shopping forays to amass a number of new outfits, underwear and stockings all of which he was aching to try on. He ordered a new wig via one of the sites on the Internet and, as Joanna would be taking most of her make-up with her, braved the cosmetics counter at Boots to get a supply of his favorite lipsticks, eyeshadows and foundation. A new supply of Dermacover beard cover and some sexy high-heeled shoes in his size and a range of false nails all arrived from his mail order efforts just the day before she was due to leave.
That evening, they made passionate love in the bathroom and in then again in the bedroom before falling asleep. The next morning, Steve ran Joanna to Heathrow and, after a tearful parting, drove on to work. He couldn't concentrate on the job in hand, thinking of what lay ahead for his hoped-for fulfillment of his fantasies. Fortunately, his boss thought it was just pre-holiday excitement as Steve had booked 2 weeks off allegedly so that he could decorate the home as a surprise for Joanna.
Driving home that night, a lot of things were running through Steve's mind on what he was going to do first and whether he dared try to go out of the house "en Femme" - what if he were spotted by someone? What if he bumped into someone he knew? Little did he know what the next two weeks would bring!!
Pulling on a pair of tight-fitting nylon knickers, he then cleaned his chest with an alcoholic wipe before putting on his favorite white bra from Triumph. Unwrapping the new silicone breasts from their box, he re-read the instructions and applied the adhesive before nestling each carefully into the waiting cups of the bra - the weight of the breasts and their feel was a very different experience form the hastily stuffed attempts he had made previously with socks and stockings. After allowing for the adhesive to set, he slowly undid the bra and let his new breasts float under their own weight - the feeling of tension on his chest and the unaccustomed feel of the new additions added to his increasing excitement and heart rate, but he had decided that the first evening was preparation only - he would not dress fully nor would he relieve his bulging insistence cramped within the confines of the nylon underwear.
In knickers and with his new breasts swaying gently as he walked, he moved into Joanna's dressing room and pulled out his hidden cache of clothing. Selecting a long cream night-dress wit matching negligee, he pulled them on over his smooth body and nestled his feet in a pair of Joanna's mule slippers. Feeling increasingly calm and happy with himself, he slowly brought out all of his new purchases and arranged the make-up in the drawers so recently emptied by Joanna's packing and carefully hung up his clothes in the vacant spaces in her wardrobe. He would decide what to wear tomorrow, when he got up in the morning, but the next step was to do his nails.
Selecting a pack of false nails in his favorite color - Flame Red, he then carefully shaped his toenails and cleansed them fully before applying first one and then a second coat of varnish. The finished result sparkled back at him in the lights of the dressing room, he then slowly selected the false nails to match the shape of his own and, applying the superglue, attached them one-by-one. Admiring the finished effect in the mirror he was surprised to see that it was past midnight already "A girl must get her beauty sleep he thought", so putting on his wig and allowing the dark curls to fall gently over his shoulders he turned out the lights and slide blissfully into bed.
He got up and admired his reflection in the mirror. Shaving carefully to remove as much facial hair as possible, he applied a thin layer of Dermacover and smoothed it over the darker regions of his face before applying the setting powder - he always enjoyed watching his face change as he applied the foundation and make-up. Re-styling his wig, he then took off the night-gown and put on his bra before changing the knickers for a tight black pair and pulling on a pair of ultra-sheer tights. the feel of the pantyhose against his smooth legs almost made him come into the new knickers and he had to sit calmly to suppress his desire to relieve the tension - later, later he said to himself.
Next was a new, cowl-necked blouse in white with long sleeves and pearl buttons before he pulled on a woolen fitted skirt in dark grey lined with a polyester which crinkled to the touch and fell smoothly against his nylon-clad legs. A pair of black patent court shoes with a 3" heel came next before Steve put on a pair of gold colored clip-on earrings and his 2 favorite rings, borrowing Joanna's gold bracelet and pulling a long gold chain around his neck, he then gave his hair a final coiffure before parading in front of the mirror. The person looking back at him was a very attractive and confident woman, he whooped with delight.
The rest of the day was spent walking around the house, fixing some lunch and surfing the transgendered net - he really enjoyed the chat rooms and became bolder with his on-line talks across the globe. One "girlfriend" asked Steve "Do you have a Femme name?", Steve had often thought about giving his other personality a name, but had never come up with an idea. he responded with a general request to all in the Room about what name he should choose and the replies came thick and fast - many either too "sexy" or just not right. Eventually he saw Caroline and liked the slightly cool-yet-confident nature of the name, "My name is Caroline" he confidently typed into the computer.
One morning, a few days later, Caroline awoke in her short blue night-dress, got up and showered, shaved and made herself up subtly. She had decided yesterday that today was the day to brave going out of doors as Caroline. Choosing a knee-length brown dress, tights and brown shoes, she dressed and put a few "essentials" into one of Joanna's handbags. Inside the handbag, Caroline saw a long cigar-shaped plastic container which, on further probing, revealed two tampons nestled together in a tasteful pack - "Real girls have periods and need protection, what am I to do?".
Moving to the bathroom, she pulled down her tights and cream knickers, finding some moisturizing lotion, she smoothed it over the entrance to her rectum and over the rounded end of the tampon before pushing the tampon in and withdrawing the applicator. It felt very strange and somewhat uncomfortable with the tampon slowly expanding inside her, but she pulled up her knickers and tights and checked herself in the mirror. Selecting a large overcoat from Joanna's collection, she walked downstairs and took out the car keys.
Caroline's heart was pumping hard as she checked outside to make sure that no-one was looking before she stepped out of the front door, pulled it shut and walked briskly to the car. The click of her heels on the front drive, the sway of the dress against her legs and the tight feel from the tampon served to heighten her pleasure and her excitement. Into the car and adjusting the seat - high heels make it more difficult to drive, she drove off carefully and into the town. Driving through busy intersections she noticed a few other drivers being more courteous than Steve would normally expect and many of the other lady drivers smiled.
She drove on into the country and found a quiet car park near a small housing estate - time to try the fantasy out. Se had read many letters on the dangers of going out and the pitfalls of being spotted, but she was far enough from home and it was the one thing she had never done before. Out of the car and, careful to take smaller steps and to swing the hips slightly, she walked towards the houses, enjoining the sounds of her heels on the pavement and the feeling of freedom as the dress moved over her thighs and her breasts moved gently in the confines of her bra. Suddenly, a door opened in one of the nearby houses and a man and woman emerged to get into their car, Caroline almost bolted but the man merely threw her a glance and the woman smiled as she walked past - phew!
Gaining confidence, Caroline walked further and was lost in reverie when a man came around the corner walking his dog. He smiled at her and the dog wagged its tail before they passed each other, the man muttered "Good Afternoon", Caroline smiled back and walked on. She had done it!! There was no sign that he had suspected anything!! She walked back to the car and drove home in a state of complete euphoria. That night she relived the excitement of that day and wondered where to next?
Thinking quickly, Caroline took off the night-dress she had been wearing and threw on a pair of jogging pants and a tight tee-shirt to compress her breasts before putting on a loose-fitting sweat shirt. Fortunately, she had fully cleansed her face the night before and had removed her false finger nails in preparation for a new color and set for the next day.
"Hi, Sandra" a flushed but smiling Steve said as he opened the door, "Sorry, you caught me sleeping in late, do come in". Sandra walked in and started to talk in that rapid emotional manner that Steve had always found irritating on the few occasions that Steve and Joanna had dinner with Sandra and her odious husband, Mike.
Sandra said that she knew that Joanna was away and had dropped by to see if Steve was OK. It soon became obvious that something was clearly wrong and Steve asked Sandra what the problem was.
"I've got a problem with my marriage and I think you might have a problem with yours" Sandra blurted out. It emerged that Sandra was convinced that Mike was spending some of his evenings in the local bars picking up girls for one-night stands, often coming home late stinking of alcohol and cheap perfume. She had challenged him but he became violent and she was worried what might happen. Steve tried to console her, but it was obvious that she just wanted to get her problems off her chest.
After drinking tea together, Sandra asked "Steve, I know it may be none of my business, but I am Joanna's best friend and I don't want to see her hurt. You're on your own here for three weeks and a friend of mine saw a woman coming into your house a few days ago. She said this woman was a tall brunette and that she was driving your car - Steve, what's going on?" Steve blushed and stuttered that he had taken a few days off work to do some decorating and that a work colleague had dropped by because her car had broken down and she wondered if she could borrow Steve's whilst he was at home. Sandra seemed pacified by the answer, but looked at Steve in an odd way, Steve glanced down at the floor and saw, to his horror, his bare feet sticking out from his jogging suit bottoms resplendent with nail polish freshly applied last night. He looked up quickly and his eyes met Sandra's - she had seen his feet too and a glint appeared in her hazel eyes.
"Joanna has told me that you had asked her if you could wear some of her things during lovemaking. I said that it was probably harmless and if it helped, what the hell. So what's going on, Steve - or should I call you something else?"
Steve, slowly at first but with gentle persuasion and understanding from Sandra, told her everything about Caroline and how he had been planning this two week vacation so carefully. Sandra seemed to understand and jokingly said "Well, if you want a girlfriend to go out with, let me know - although how believable are you?". They talked about Mike and his infidelities over more tea, gradually relaxing in each other's company before Sandra said it was time for her to go. As she stood at the front door she said "I'll be around tonight at Eight, be ready for a girl's night out, see you then Caroline".
Six or seven changes of outfit later, Caroline sat nervously on the sofa waiting for the knock at the door. At eight fifteen, she had convinced herself that Sandra wasn't coming. At eight thirty a sharp rap at the door almost sent Caroline into cardiac arrest, checking her hair in the hall mirror she opened the door and blinked as a flashgun exploded with light from the camera Sandra was holding. "Wow, you look really good" said Sandra taking two more shots in quick succession, " You've got better legs than me you bitch". They laughed and Sandra got Caroline to pose for more photos until she finished the roll of film.
"Let's go girl". They got into Sandra's BMW and drove for half-an-hour to a bar in a part of town Steve had never been to. "Where are we?" asked Caroline, " Sufficiently far away that we'll not be spotted and in a bar where we won't get molested by the low-life males that prowl the city center. Caroline had not given any thought to the dangers of being a girl out on the town, it worried and excited in equal measure.
Sandra ordered drinks for both of them, Caroline's voice was wrong and needed some training but she would pass provided nobody got too close. They chatted in the quiet ambiance of the bar, ordered dinner and had a great time. Caroline could not help noticing the admiring glances from the male patrons of the bar, wondering what the two well-dressed women looked like to the casual observer.
Sandra said "I really must go to the washroom, want to come with me?", Caroline gulped smiled and followed Sandra to the Women's room watching the eyes of the other diners as they fixed themselves on Caroline's exquisite legs. In the privacy of the toilet, they chatted quietly whilst washing hands and fixing lipsticks "You know, you're really good - we need to work on the voice and walk, but you could pass almost anywhere" said Sandra. Caroline smiled and was about to reply when a stunning blonde walked into the room and proceeded to adjust her stockings, Caroline couldn't take her eyes off but a sharp dig in the ribs by Sandra quickly brought Caroline to the realization that, whilst she had a male sex drive, this would look odd coming from someone obviously female. The blonde shot Caroline a frown and the two ladies returned to their table.
Back at Caroline's house, they shared a coffee and Sandra left for home saying that she would be back to take Caroline shopping the next afternoon. "Wear something casual, a skirt and jumper, nothing too outrageous".
Walking together through the shopping malls, the two ladies mingled without a second glance from the throng of busy shoppers. They went into to a number of shops and, with a bit of trepidation, Caroline agreed to try a few things on. The saleswomen didn't give Caroline a second look, one even pulling the curtain aside to check if Caroline was all right - the shock of being seen in bra and pants almost causing Caroline to shout out loud.
Back at home, tired and exhausted from their shopping, they both tried on their new purchases and had to stop when Sandra started to remove her bra before trying on a halter neck dress. They laughed and Sandra said "Listen, I've been thinking, a friend of mine is a speech therapist and I'm sure she said that she had helped train some men undergoing sex change to alter their voice. I'll get the details from her and call you back - OK?"
The following afternoon, Sandra returned with a bundle of videos and they worked their way through the training sessions, Caroline's voice, breathing and diction slowly mellowing and becoming more feminine. Sandra had also brought a full kit of make-up and acrylic nails and spent hours getting the new nails right before concentrating on Caroline's make-over. They both agreed that the end result was fantastic.
"Sandra, you've been great and I cannot thank you enough - but I don't want to be unfaithful to Joanna and I don't want to become a woman full time. How can I repay you?"
Sandra thought for a while and said slowly "Caroline, I see you as Caroline, my new best friend, not as Steve, my other friend's husband. Were just good girlfriends and I would like to keep it that way - even after Joanna returns from her trip. But there is one thing I want you to do and I'm prepared to publish all these photos I have of Caroline unless you agree to what I want". Caroline put her carefully manicured fingers to her scarlet lips in surprise "What?" she asked in a tremulous voice.
"I want you to seduce Mike" Sandra said in a matter-of-fact voice. "Not all the way, but far enough so that I can get the photographs and evidence to get rid of the bastard"
Sandra and Caroline spent the next few days perfecting Caroline's Femme image and planning the downfall of Mike.
Two nights later, Caroline was sat at a stool in Mike's favorite bar. She had already fended off two attempts from the local Romeos when Mike sauntered into the bar and ordered a beer. He glanced at Caroline and she nervously smiled back - which he took as a signal to come over and talk. "Have we met before, your face is familiar?" Mike opened, "I don't think do, my name's Caroline" she responded, frightened that the carefully laid plans would fall at the first hurdle. Mike started chatting and the fell into a one-sided conversation with Mike telling how his wife didn't understand him and how much he needed female company.
After dinner, Mike asked Caroline where she lived and the plan drew to its conclusion. "I'm not local, I'm staying at the Marriott" she responded and after a little sparring, she agreed to go back to he hotel with him. They drank a few more brandies and than Caroline said "Mike, do you want to come upstairs with me?", he tried to kiss her then but she fended off his advances and they moved to the lift. Opening the bedroom door, Mike lunged at Caroline and she felt his hand moving towards her breasts "Wait a minute, I'd like to slip into something more suitable, get yourself another drink and wait for me".
Mike moved into the sitting areas and opened the minibar to pour a beer, Caroline emerged in her most sensuous night-dress and moved towards Mike's drink, just managing to pour the contents of a small sachet into the glass before his tongue started to explore her body. "Stop, stop, doesn't a girl get a drink as well?" Mike reluctantly disentangled himself and poured a glass of champagne "Cheers" said Caroline and downed the drink in one, Mike followed suit and made one more lunge for Caroline before he grunted and slipped slowly down t the floor.
Caroline picked up the phone and dialed another room, Sandra appeared minutes later. The two girls stripped Mike and moved him to the bedroom, Sandra set up the camera and took a video of Caroline slowly undressing in front of a recumbent Mike before removing her breasts and showing the video camera "her" manhood. Sandra was careful never to let Steve / Caroline's face appear in the viewfinder as they completed the production of a video depicting Mike, the stud being seduced by a transvestite.
Steve left the room whilst Sandra inserted a dildo into Mike and made sure that he would be walking a little gingerly in future. For good measure, she manipulated Mike's flaccid penis until he came all over the bedclothes. Finally taking a series of Polaroids, she scattered them around the room and, when Steve returned reinstated as Caroline, the two ladies returned to the bar downstairs and got thoroughly drunk.
A month later, Joanna told Steve that Sandra and Mike were getting a divorce. Joanna said that Mike had suddenly become very quiet and withdrawn and had been fired from his job over some misconduct a few months ago with a secretary, she though he had been a bit of a *** to Sandra.
Sandra came around often and Joanna's work kept her away approximately one week in each month. During those times, two attractive ladies could be seen having dinner and shopping together, women enjoying each others' company as only women can.
The End