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After Wife's Death
🕑 Added 2021-07-19 12:41:01 +0000 UTCJust a short story...
Summary - A crossdresser loses his wife in a car accident and slowly transforms himself into his loved one.
Gary felt that he probably was one of the luckiest guys around. Sarah, his wife, was good-looking and very successful at her job in the jewelry wholesale business. They had been married for four years and, while Gary made a decent income from his home-based computer software business, it was Sarah who paid for exotic holidays and weekends away. They had no children, partly from Sarah's wish to keep her career going and also because neither of them were really convinced that they were ready for a family yet.
Gary and Sarah could have been mistaken for brother and sister; they both had dark hair and were almost the same height with a slender build. Sarah had the most amazing green eyes, which sparkled when she smiled - which was often, while Gary was often quiet and kept himself to himself. The similarity in their build and appearance was a bonus to Gary as he often took advantage of Sarah's business trips to dress up in her clothes and wander around the house "en femme." Sarah knew of Gary's desire to dress up occasionally. While she didn't really understand why he did it, she was content to let him dress up if she was out of the house. She drew the line at making love with him dressed, although they both enjoyed the occasions when Sarah found Gary in their bed wearing one of her long satin nightgowns and a pair of tight knickers.
Gary longed to dress and go out with Sarah as two sisters, but he respected her wishes and was reasonably content with the status quo. Over the years of their marriage, he had amassed a suitcase full of silicone breast forms, waist clinchers, and body shapers, jewelry for his larger hands and his unpierced ears, as well as the essential beard cover and a few pairs of mid-heeled shoes. He always enjoyed going out shopping with Sarah, particularly if she was looking for a new outfit as he knew that once she had brought it home, he could try it on in the next few days. A few of Sarah's girlfriends had commented, in earshot of Gary, how unusual it was for a man to be happy clothes shopping with his wife.
One Monday, Sarah announced that she would be going away on a business trip up North with her business partner, David Smith, and expected to be away for most of the following week. Gary was sorry to see her go, but once David had collected her from the front gate, Gary went inside the house and immediately started on his well-rehearsed ritual of turning himself into his version of Sarah. He kept his body free from hair, so a quick shower in Channel gel and an all-over dusting with talc made him feel fresh and a little sexy. Pulling on a tiny pair of bikini briefs, he pulled his manhood between his legs and glanced at himself in the mirror as his body started to take shape. The silicone breasts were carefully cleaned and sprayed with adhesive before he stuck them firmly to his chest, applying some Dermacover to smooth the outlines. A new bra from Sarah's M&S collection to match the briefs, and then Gary quickly and expertly applied subtle makeup before stepping into a new pair of sheer nearly black tights; he always loved the feel of the lycra as it rolled up his smooth legs.
Stepping into a new red and black dress Sarah had bought at the weekend, he pulled the zip up, selected a pair of black patent shoes with a 3-inch heel, and returned to the dressing table to brush and fix his shoulder-length dark brown wig, which was set in a style almost identical to Sarah's. Earrings, bracelets, rings, and a gold necklace finished the transformation, and Gary looked at himself in the mirror. To the casual observer, it would seem as if Sarah was the one standing in front of the mirror.
Gary spent the next few days dressed "en femme," changing into outfits as he felt he wanted to and going to bed contentedly in sheer nightgowns after each day. He continued to work at home and communicated with his clients by Email and telephone, so most of them had never met him, but we're happy with his output. Little did they know that the man communicating with them was sat as his computer in an ever-changing array of smart business blouses and skirts.
His work, mostly covering computer software problems which had arisen overnight, meant that everything became quiet after mid-day. On most afternoons, he could dress in a pair of Sarah's trousers or a simple skirt and jumper and step out onto the drive, getting into Sarah's Rover and driving off into the traffic. He enjoyed the feeling of freedom in the car and the fact that most fellow motorists would be blissfully unaware that the attractive woman in the car was not what she seemed. One day, wearing a mid-length green skirt and a roll-neck fawn jumper, he plucked up the courage to stop at a drive-in McDonald's, the young girl serving either had no idea that she was serving a man or didn't care. Having finished the meal in a nearby superstore car park, Gary decided he should try to get a few essentials for the house as there was almost nothing in.
He had only ever stepped out en femme either to the car on the drive or occasionally he had plucked up the courage to pull on a long coat and walk deserted pavements in the evenings. He knew that "real" women rarely walked alone at night, but he didn't want to be spotted.
He sat in the car and watched the busy shoppers going about their daily business; there was a large number of women - some with children, some alone, all looking stressed as they rushed into the store. Checking his makeup in the mirror and fussing over his hair, he finally decided to go for it, reminding himself to take short steps and to walk slowly. With heart racing, he slowly got out of the car and pulled on Sarah's biggest coat - fortunately, it was bitterly cold. He took the handbag off the passenger seat and double-checked that he had enough cash; he didn't want to get stopped using Gary's credit cards while dressed as Sarah! Walking across the car park, he heard the click of his heels on the concrete and could feel his heart racing; what if he was found out? But most of the store was busy, and he quickly stocked up on a few essentials, adding a pack of tampons and lipstick to his basket. He stood in line at the checkout, where he noticed a neighbor at one of the other queues but managed to avoid any eye contact. The checkout was run by a pimply male who didn't even look up as the purchases were scanned, and Gary paid and walked out.
He felt exhilarated and drove carefully away from the store, smiling at a young man in a sports car who let him out into the mainstream of traffic. Back home, Gary put the shopping away and changed into a housecoat. He planned to have a bath later and really pamper himself; then the 'phone rang, it was the neighbor from the superstore. She asked to speak with Sarah and, when Gary explained that she was away, exclaimed that she swore that she had seen Sarah earlier. Maybe, Gary mused, I am more convincing than I thought. The trips out became more frequent, and Gary spent more time walking around the shopping precincts nearby. He didn't trust his voice or demeanor enough to risk going into the attractive women's clothes shops, but he contented himself with window shopping and slipping into the larger chain stores where he could buy some clothes without the ordeal of a saleswoman continually interrupting him - and maybe guessing what he really was. He had walked past a particular shop a number of times and had gazed at a black evening dress in the window which had been marked down in price in a sale. As he looked again at the dress, a woman approached him from the shop;
"Lovely isn't it, and such a bargain?" she said, "why don't you try it on? I'm sure it's your size". Gary felt himself stammer a falsetto. "I'm not sure," but the saleswoman just smiled at him and held the shop door open. The shop was empty except for the woman and another assistant; she led Gary over to a rail of clothes and pulled out another black dress;
"Size 14, I think, here, the fitting rooms are just over there" she led Gary to a door which opened to reveal a well-lit small room with a full-length mirror. Gary took the dress and closed the door; he quickly removed his coat, skirt, and roll-neck pullover and pulled the dress on; it fitted perfectly. He adjusted his wig and put his shoes back on, they were the wrong color, but the change in posture caused by the mid-heels served to accentuate the elegant drape of the dress.
"Let me see," said a voice from outside. When Gary opened the door, the saleswoman looked admiringly at the new dress and said, "there, I told you it would look good." Warming to her open smiles and frank gaze, Gary mumbled that he would take it and returned to the fitting room to put his street clothes back on. At the checkout, the woman had already wrapped the dress and placed it in a smart carrier bag with the shop's logo emblazoned on it.
"That will be one hundred and forty-nine pounds please, how would you like to pay?"
Without thinking, Gary handed over his Visa card. The woman swiped it through the machine, and they waited for it to print the signing slip; Gary signed rapidly.
"Thank you very much, Madam," the saleswoman said while looking at the signature and comparing it with the credit card. She looked up into Gary's eyes, "I'm sure you'll like the dress, and please feel free to come back at any time; I would be only too happy to pick out a few more things for you." Gary smiled back and walked out of the store. She obviously knew he was not a woman, yet she had no problems about helping him choose clothes; Gary was delighted to have found someone who could accept him for what he really was. Made bold by the success of buying the dress, Gary walked to the nearby theatre and bought a ticket for that evening's performance of his favorite opera, Tosca.
Later that evening, Gary was standing at the mirror resplendent in the new full-length black evening dress with his hair pulled up to set off his glittering makeup, impossibly long freshly-varnished acrylic fingernails, and a pair of 4-inch black patent stiletto heels. He smiled at the reflection, pulled on a black evening jacket, and walked out to the car. Driving into town, he parked near the central district and joined the throngs of cinema and theatre-goers as they milled about the entrances to the entertainment centers. He followed one crowd in and, showing his ticket to a smart usherette, entered the rapidly filling auditorium where he sat next to an older couple who took no notice of him. The opera Tosca and was quite well sung in English. At the interval, he stayed in his seat; although he noticed one or two of the passing audience looking at him, he ignored them and continued to sit quietly, enjoying the feel of the evening gown and the sheer underwear as he moved in his seat.
It was then that he noticed the saleswoman from that morning sat with a man a few rows in front of him. As they rose to move to the bar for interval drinks, the woman spotted Gary and smiled; his heart sank as she pointed her husband toward the bar and then came over to talk to Gary.
"Well, I'm glad to see the new dress is having an outing already; stand up and let me see it" Gary stood, and the woman complimented him on the makeup, hair, and shoes.
"Tell me, dear, what is your name," she said.
"Sarah, Sarah Howe," Gary stuttered.
"Well Sarah, I hope that you are enjoying the show and your new dress. You really look very good, and I must compliment you on your dress sense. Many women can't co-ordinate clothes as well as you seem to. Please do drop in to my shop, especially on Thursday afternoons when we're not very busy - I'm sure we could find lots of things for you". With that, she touched Gary's hand lightly and moved off to join her partner at the bar.
The opera concluded in its height of emotion and sound, and Gary followed the crowd out, smiling at the older couple as they gushed at how marvelous the soprano was.
Walking back to the car, he drove home. Once back home, he reluctantly removed the dress and shoes; leaving the black underwear and sheer panty-hose on, he slipped into a long black silk nightdress and a thin negligee, let his hair fall loose in cascades over his shoulder and went back downstairs to fix himself a small brandy. The sight of his reflection in the hallway mirror was of a sophisticated woman ready for bed if only he had someone to share with! The thoughts and the pent-up emotion of the last few days eventually forced his penis erect against the tight fabric of the sheer material of his knickers; he sat down carefully and slid himself backward and forwards on the leather sofa, feeling the movement of the fabric against his straining manhood. Releasition came in seconds as he felt himself get bigger and bigger before the eventual climax and the rush of pleasure as he spent his feelings into the warm embrace of the tight underwear. Moving quickly, he stood up and removed the panty-hose before the fluid leaked out from the underwear; he then walked to the bathroom and removed the knickers before cleaning himself up and selecting a fresh pair of black knickers into which he placed a panty liner before pulling the garment tight, encasing his manhood once more. He washed the soiled undergarment and the nylons before returning to the sitting room to drink the brandy before retiring for the night.
The next day was a Thursday, so Gary dressed carefully in a smart but simple woolen dress and returned to the shop at about 4 pm. Once more, the shop was deserted, and he walked in and started to look through the racks of dresses, skirts, and blouses, marveling at the rustle of the material through his fingers.
"Sarah, so nice to see you" the woman had moved into the shop from the stock room.
"See anything you like yet?" without waiting for a reply, she went to the main door of the shop, flipped the sign over to read closed, and bolted the door.
"There, we can have some peace and quiet, and you can try on whatever you want. By the way, my name's Stephanie, but my friends call me Steph". She smiled.
Gary swallowed hard. "Why are you being so helpful and nice to me?" he asked querulously.
"I can see that you aren't really Sarah, but you looked so lost yesterday, and I felt that, after all, what's the harm if one of my customers is a man. You look good in my clothes, and I need the business, particularly on a cold rainy Thursday afternoon". Steph grinned, "now, what do you need for your wardrobe?"
Relaxing into Steph's company and egged on by her insistence that he try on almost everything that fitted, Gary spent three hours in absolute paradise. They finally plumped for two simple skirts in fine fabrics, a smart grey striped business suit with skirt and trousers, and a stunning, short red dress. Steph measured Gary's trousers and arranged to have them lengthened so that they could accommodate his long legs and still look good over high heels. He paid for the goods, and Steph threw in some costume jewelry as a gift; overcome with joy, Gary kissed Steph lightly on the cheek.
"Thank you so much, I've really enjoyed myself, and it's fabulous to have someone help me with clothes," Gary smiled.
"Come on, let's go over to the coffee bar, and we can chat a bit more, and you can tell me about Sarah." Gary and Steph left the shop and walked, arm in arm, to the coffee bar, where they sat at a quiet table and chatted. Gary told her everything about his desires to dress up, his wife's understanding, and his wish to try to pass as a woman. Steph was supportive and laughed and joked to the other patrons of the coffee bar; here were two women enjoying an afternoon together after a shopping spree.
At Steph's house, she invited Gary in and introduced her to her husband, Steve, who was just leaving for an evening out with some business partners. They left the bar, and Gary offered to drive Steph home as she usually walked the half-mile or so. Once alone, Steph took Gary's hand and led him up to the bedroom. Gary stared as Steph stripped off to reveal a black boned basque with suspenders holding up her black stockings. Without pausing, Steph stepped up to Gary and unzipped his skirt, easing it down to the floor. She reached down to Gary's panties and released his hardened penis from the embrace of the underwear; taking him into her mouth, she started to rock gently backward and forwards, the shaft of Gary's manhood pushing deeper and deeper into her welcoming mouth.
Gary moaned with pleasure and saw his reflection in the full-length wall mirror. An attractive woman with her partner riveted to her genital region; it looked so sexy and fulfilled Gary's wildest fantasies. With a rising crescendo, Gary's back arched as he came full into Steph's waiting mouth. She swallowed greedily and then licked the head of his penis, wiping all traces of cum from his now flagging manhood.
"Wow, that was wonderful. Now it's your turn" Gary bent down to lift Steph up. Gently he lay her on the bed and started kissing the moist patch on her jet black knickers; moving the material to one side, he slid his tongue into the waiting folds of Steph's vagina. Moving tongue and hands, he rapidly brought Steph to a climax as her body writhed and arched in multiple orgasms.
They lay together for a short while, and then Steph got up and got dressed. Gary followed suit, and they went downstairs and chatted happily. Steph's husband eventually returned home, but he ignored the two chatty women, contenting himself with watching TV.
Gary left the house later that evening with a glint in his eye and promised to visit Steph at the shop the next day. Their lovemaking continued at every conceivable moment. Trying on a new dress in the changing room, Steph burst in and virtually raped Gary, forcing him against the wall as she pulled his penis out from the underwear and into her waiting moistness.
The week with Sarah away was nearly over, and Gary was getting ready to remove his feminine wardrobe when the telephone rang. It was the Police asking if Gary was in, he said yes, and they asked him if he was expecting his wife home this evening - Gary was immediately suspicious and asked what the problem was. The Police replied that there had been an accident and they would send an officer round to the house to talk to him.
Gary's mind was racing; what could have happened? Was Sarah all right? What was going on? He quickly ran upstairs and removed his makeup and wig, disguising the firmly stuck breast forms with a tight T-shirt and a loose jumper; he pulled on some jeans just as the front doorbell rang. Opening the door, he was confronted by a male and a female Police officer who asked to come in. Gary heard that Sarah had been in a car accident as a passenger and was dead in a daze. He never heard the rest of their consolations, his mind was a whirl, and he couldn't take in what they were saying. The next few weeks went by as if Gary was somehow disconnected from the world. Sarah's parents came down the next day, and between them, they organized the funeral and all the petty details that help people get through the grief and disbelief. After the last mourner had left, Sarah's mother offered to take her clothes away, but Gary, in a brief period of lucidity, said that he didn't want to let her go just yet.
All too soon, Gary was alone in the house. Sarah's insurance had now paid the mortgage and left him with a fairly comfortable income; a few friends had dropped in to offer help and "anything we can do, just shout," and then some of them had promptly disappeared. Steph had called by, and they had talked, but Gary wasn't up to her advances, and they agreed to part as friends, maybe picking up their affair when Gary had sorted himself out.
He was now alone; what can he do now? He despaired, cried, shouted, threw things at the wall, and was very rude to the few friends he had left until no one bothered to call him. He had not done any work for weeks, and clients who had been understanding over deadlines started to pressure him to deliver, he told most of them to off, and they rapidly moved their business elsewhere.
Gary felt very alone and very sorry for himself. Opening the wardrobe to find things to wear, he was captivated by the smell of Sarah's perfume on her clothes, and it was not long before he found solace in dressing up in her outfits and spending more and more time pretending to be Sarah. Feeling wretched one weekend, he went out to the local pub in jeans and sweatshirt over a tight set of bra and briefs with matching suspenders and nearly black stockings. He drank for most of the evening, ignoring the bartender's gentle suggestions that he had drunk enough and should really be going home. At closing time, he staggered to his car and set off for home. About a mile before his home, he saw a flashing blue light in his rearview mirror, and he was pulled over - he lost his driving license immediately and a few weeks later received a 12-month ban and a hefty fine.
Now he could do nothing, no driving, no friends, nothing.
He missed Sarah terribly and only felt human when he dressed in her clothes. Her handbag had been returned intact from the accident, and he found her driving license and credit cards safely in the purse he had bought for her one Christmas. Well, if Gary was no longer allowed to exist, why couldn't Sarah return? With increasing daring, he started to return to the ways he had learned during the week Sarah was away, spending days and weeks as Sarah, going out and ignoring the neighbors' stares as he tried to build a life as Sarah. A reminder letter from Sarah's optician allowed him to get a repeat prescription for her contact lenses with a solid green tint which, after much experimentation, made his face look even more like his dead wife's.
The months went by, and Gary had let his hair grow. He had been taking her oral contraceptives and had got a repeat prescription, which made his skin smoother and his beard growth less vigorous. His nails were getting longer, to the point where he did not need the acrylic extensions to create an image of sophistication. He believed he was Sarah and, to a casual observer, was the image of her.
Walking into the shop on a Thursday lunchtime, Steph was delighted to see him and immediately commented on how good he looked. She noticed the smoother skin and the green eyes, and her interest was piqued. They went to the coffee bar, and over copious quantities of strong, dark coffee, Gary talked to Steph of his thoughts. She asked him if he was attracted to men, and Gary answered, honestly, that he had not given it much thought. He had noticed the looks he got when walking out like Sarah and enjoyed the attention, but he had not considered the sexual implications of a permanent change to being Sarah. He increasingly thought of making the transition to Sarah more permanent and plucked up the courage to try and reopen his friendship with Steph from the shop to ask her. They talked for a while, and Steph was very supportive; she even suggested they went out on a double date so that Sarah could get a feeling for a man's attentions. Reluctantly, Sarah agreed, and they set a date for the next Saturday evening, nothing too rushed, just a quiet dinner at Steph's house with her husband and a male friend.
All through the next Saturday, Sarah (for Gary had got to the point of thinking himself as Sarah) bathed and washed her hair before trying on virtually every outfit in her wardrobe. Finally pleased with a simple, knee-length black knitted dress and subtle makeup, she drove to Steph's, where she eventually plucked up the courage to ring the doorbell. It was answered by Steph's husband, who immediately introduced Sarah to Alan, a tall, well-dressed man with greying hair and a ready smile. Over dinner, they all chatted, and Sarah and Alan seemed lost in just talking to each other about everything and nothing. Making an excuse to go and powder their noses, the two ladies compared notes in Steph's bedroom,
"Well, what do you think of your first date as a girl?" Steph asked, eyes shining mischievously.
"He's nice, and I like him. It's so good to be able to just talk with someone, but I'm not sure I want to go any further," Sarah replied.
The rest of the evening went well, and Sarah accepted a kiss on the cheek from Alan as he said his goodbyes, he slipped her a note with his 'phone number on it, but Sarah knew this was not for her. Steph and her husband invited many eligible men to dinner with Sarah. She slowly lost her inhibitions and enjoyed herself thoroughly, never going beyond a chaste kiss and a promise (unfulfilled) to 'phone. One evening, Steph suggested that they eat at a new restaurant and for both girls to wear their best, most sexy, outfits as there was dancing and a cabaret.
Sarah's companion for the evening was a dazzlingly well-dressed man in his late thirties with clean clothes and equally considerate manners. They had a great time, laughing at the comedy sketches and dancing to the disco. When the last dance came, Sarah's partner pulled her onto the dance floor and held her tight as they moved to the slow music. Sarah could feel the hard outline of his penis against her stomach and, to her surprise, felt her own much-neglected organ start to respond. He kissed her full on the lips, and she responded with vigor, the music faded away, and they just stood there in each other's arms. He leaned close to her ear and said :
"Sarah, don't worry. Steph has told me all about you, and I know your secret. Will you come home with me tonight?"
Sarah stared at him and then looked across at Steph, who smiled and winked back.
"I don't know. Will you excuse me? I need to go to the bathroom" with that, Sarah disentangled herself and, grabbing Steph's hand, dragged her into the ladies' room.
"What have you set up here" Sarah demanded of Steph.
"You like him, don't you. He's nice, and I've known him for a long time. He's bisexual and was very happy to come out with us tonight and just to take things as they come. It's up to you now, girl" Steph smiled.
Sarah returned to her companion and asked him to give her more time. She promised to 'phone him in the next day or so. With that, the party split up, and everyone returned to their own home.
Sarah 'phoned Steph the following morning in complete confusion over what she should do. Yes, she was attracted to him, but the idea of sex with a man still wasn't easy to think of, yet she had felt her response to his touch, and there was no denying that she had not had sex for a long time. Eventually, they agreed for Steph to come round that evening to talk it through so that Steph could be there when Sarah 'phoned him.
Steph arrived straight from the shop at 6.00 pm, and they talked and talked. It was clear that Sarah wanted the love and affection; she just wasn't sure about the physical part. Eventually, Sarah picked up the phone and talked to her date from last evening. He was insistent but gentle. Finally, Sarah agreed to go around to his place in an hour. Steph was thrilled and rushed out to her car, carrying in loads of garments wrapped in tissue paper. To Sarah's delight, she pulled out a new, lacy white basque with white stockings and white satin court shoes. Handing Sarah a pair of white silk knickers from Janet Reger, she also gave her a pot of Vaseline and a pack of tampons.
"These are for you, it's your first big date, and I want it to go well. Make sure you get yourself ready, smear plenty of Vaseline on the tampon, and experiment with getting it into you. You'll find it's easy after a couple of goes. Then put as much Vaseline into you as you can and put a tampon in to hold everything in place. Believe me, it's worth it" Steph was the boss now.
Sarah did as she was told and enjoyed the smooth feeling as the Vaseline coated her rectum, the tampon slipping in smoothly. The underwear was beautiful, and she slipped on a simple, short white silk dress. Steph touched up Sarah's makeup, and then, giggling like schoolgirls, they got into Sarah's car and drove over to her appointment with her destiny.
Alone in his bedroom, he slowly slipped off her dress and began to run his tongue down her bare stomach. Reaching her white silk knickers, he felt for the pulsating penis within the material and slowly ran his hands along the outline of the shaft. Sarah moaned with pent-up pleasure, and she started to undress him until he was naked. Taking his huge penis in her hands, she knelt down and brought it up to her face, she could smell the pre-cum on him, and it was arousing her in a way she never expected. She knew she wanted to feel him inside her and she slowly brought his member into her mouth, the sensation was wonderful! He groaned loudly, and she took the whole length of him into her, gagging as his penis head touched the back of her throat. Rocking backward and forwards in a rhythmical motion, she could feel him tense, and his penis gets bigger. In the bedroom mirror, she could see a sexily-clad woman ministering to her man, and that woman was her!
Suddenly, he let out a grunt, and his penis swelled before releasing its hot salty contents into her throat; automatically, she swallowed the cum and savored the sensation as it ran down her throat. He pulled her off him and laid her gently on his bed, positioning a pillow under her back to lift her hips into the air. She watched with fascination as she pulled her knickers to one side and pulled on the tampon string, removing the now swollen device from her well-lubricated hole. He went to the bedside cabinet and withdrew a pack of condoms which she could see was the ribbed type; he pulled a black one onto his once again erect penis and slowly advanced towards her supine body. Without saying a word, he slowly pushed the end of his penis into her waiting body; Sarah could feel pain as the size of his member pushed apart the virginal lips of her anus. The pain turned to pleasure as he started to thrust himself into her; the feeling was wonderful. Sarah's erect penis was pushing up against the silk of her underwear and was being massaged backward and forwards with each thrust of his penis into her eager body. The pent-up emotions of the last few months and her uncertainty were washed away in a beautiful mutual orgasm, her own penis releasing its load between their two writhing bodies.
They fell asleep in each other's arms, awaking to repeat their lovemaking the next morning. Sarah felt whole and was convinced this was her true future.
Comparing notes with Steph a few days later, they both agreed that she seemed happier than ever before. Sarah talked again about gender identity, and Steph agreed to go with her to a clinic in London to discuss what could be done. Three weeks later, they were sat in a quiet reception area, Sarah wearing one of her smart business suits in a grey pinstripe with a white silk blouse, black suede court shoes matching handbag, and simple jewelry and makeup. The receptionist had been very professional, and the nurse who came to take blood samples had been chatty in a very friendly way. The doctor was also a woman, and she asked many questions about how Gary had first started dressing and how long he had now been living permanently as Sarah. She also talked with Steph and asked her many questions about their relationship, which Steph described as "Once lovers, now she's my best friend."
At the end of the interview, the doctor appeared happy that all was well and prescribed more powerful hormones and a course of injections. They discussed surgery to make things more permanent and agreed on a future visit schedule to evaluate progress - Sarah was struck by how matter of fact it all was and was even more surprised when the doctor said that she too had started out life as a man.
The months went by. Sarah had stopped seeing her first man as they really did not have much in common besides sex. She had braved the local beauty salon and had come away with a wonderful glow after hairstyling, manicure, pedicure, and facial. The offer of a bikini line and leg wax was only avoided at the last minute when Sarah realized that the beautician might find more than she had bargained for. Sarah heard a car screech to a halt. Walking out of the salon, and saw his wife's old boss leap out of the car ashen-faced and run towards her. Dave was very apologetic but said that she was so like someone he once knew that he thought it was a ghost. They chatted briefly, and, reluctantly, Sarah agreed to meet him that evening at a local bar - Dave was taken aback when Sarah told him her name.
The evening was a great success, they chatted endlessly about the old Sarah, and Dave confessed that he was in love with the late Sarah and could never forgive himself to be driving the car that was involved in the fatal accident, even though it was not his fault. He kept saying how much the new Sarah was like his old love. The evening ended, and they parted awkwardly; Sarah kissed Dave lightly on the cheek and thanked him for his company, and agreed to 'phone him in the morning. Back at home, Sarah sat down on the sofa. She was confused, throughout all his time as Gary and now as Sarah, he never considered himself as attracted to men, despite her earlier "deflowering," yet Dave was different. He clearly loved the old Sarah and, in that, had a strong bond with Gary. Both were lonely and missed the one they loved, yet Gary was now Sarah - what should he do? Was it the intensive hormone treatment that was changing his orientation? Sarah slowly got ready for bed. She dressed in her favorite nightdress fell asleep feeling a warm glow she had never experienced before.
Sarah and Dave went out together frequently over the next few weeks. Eventually, Dave plucked up the courage to ask Sarah back to his house, and, much to Gary's surprise, Sarah said that she would love to. One in the house, the two kissed passionately, and Sarah was shocked at her instant sexual response to Dave's advances. The only problem was that part of the sexual response was a stiffening of her penis, which had become smaller and more flaccid as the hormone treatment took hold. Breaking for air, Sarah pushed Dave away and said that they must talk. Slowly, Sarah explained who she really was to an increasingly incredulous Dave. They talked about the hormonal treatment and Sarah's wish to complete the transformation; Dave talked about his own loneliness and the need for a focus on his life. He was not gay and had never slept with a guy; Sarah said that she had, but for her, love was more important than sex, and they both laughed. The tension broke, and both were soon kissing and embracing with increasing intensity.
Dave took Sarah's hand and led her up to the bedroom. He unzipped her dress and looked longingly at the curved trim body in black lace underwear and stockings which was presented to him. Sarah asked to go to the bathroom, where she found a tub of men's moisturizer, which she sampled before thoroughly moisturizing her anus and rectum. Looking at herself in the mirror, she checked her makeup and applied fresh lipstick, then she smiled at the reflection of an eager woman looking forward to making love to her man.
Returning to the bedroom, she found Dave in bed. She joined him, and they kissed and writhed against each other's body before Sarah moved her lips down Dave's torso and onto the base of his erect penis. Dave groaned as Sarah's lips encircled the base of his manhood, and slowly she ran her tongue and lips up and down the shaft; she felt him growing bigger, and she tasted him as a drop of pre-cum glistened on the end of his member. She plunged her mouth over him and felt the penis head touch the back of her throat as Dave began to thrust himself rhythmically into her, growing bigger and bigger. She found that she could speed him up or slow him down by decreasing or increasing the pressure her lips put on the base of his penis. Suddenly, he seemed to grow at least 2 inches, and she felt the tension in his body rise before a pulsating tide of semen gushed into her waiting mouth. Without thinking, Sarah swallowed, and the sweet-salty tide rushed down her throat.
Dave pushed her head off his spent member and brought her lips to his in a long, passionate kiss. Then he gently stood her up and led her to the dressing table, turning her to look at her reflection in the mirror; Dave made her lean forward until she was holding on to the table, her behind straining the fabric of the underwear. He pulled the black knickers up tight into her buttocks and moved them to one side. Sarah felt Dave's fingers exploring her behind, slowly and gently massaging her anus as he pushed first one, then two fingers into the lubricated hole. Sarah felt a burning sensation and looked behind to see both of Dave's hands-free, his now erect penis pushing its way into her. The feeling was a mixture of pleasure and pain, pleasure taking hold as Dave's hands reached around the front of her underwear and start to massage the now hard penis through the fabric. Dave's hands freed her penis, and she looked at her reflection in the mirror; her lipstick was spread around her mouth, but her expression was one of joy, she could see her penis in Dave's hands, and it looked as if Dave had thrust himself through her completely and was masturbating himself. With this view, she could feel Dave get bigger, and, with a grunt, she felt the warm flow of his juices enter her. At the same time, Dave's increasing rhythm on her own erect member caused it to rear up and shoot its contents against the mirror. Sarah screamed in agony and ecstasy; she looked at herself through the splattered mirror and realized she was in love.
Sarah moved in with Dave, and he supported her as she went through surgery, helping choose the silicone breasts as she entered the final phases. Two months after the final operation and feeling well, Dave arranged for them to go away to a country hotel where, over a romantic dinner, he proposed marriage. They made love passionately over that weekend, Sarah often glancing at the diamond engagement ring on her left hand.
Steph was Sarah's matron of honor at a quiet registry office wedding, having given the bride a gift of her wedding dress and a beautiful electric blue silk suit as her trousseau.
The End.
Comments
My Freeze
I enjoyed the fast pace of this story. Look forward to more stories.
Jason Dunn
I just want to say, I love the story! Just like every single other piece of your writing! However, how does she not even give a second thought to the fact that this guy considered The "old Sarah" the love of his life while she and Gary were still married? I mean, regardless of the current situation, and Dave never mentioned a physical relationship but i feel like there probably was one. personally, I would be a little upset in that position I feel like. Obviously nothing can be done now, but still. Just saying.
Urban
Hey Jessica, sorry for the late reply and thank you very much.....
J Chimera
A terrific short story Urban. Thanks so much.
Jessica Maddison
WOW .... Urban, a New short story. In just 48 hours, after your last posted. A very Impressive story, well written and to the point, with a Happy Ending. As always I Love your writing.
Randy linders
❤️❤️❤️❤️❤️❤️❤️❤️❤️👏🏻💋
Julia Miller
This was a really good short story. I felt sorry for Gary at first as he was an unfulfilled CD, and it was terrible news for him that his wife died, but he was able to move past it, taking the persona of his deceased wife. I don’t know what the legal implications would have been but if he applied for a legal name change and sex change for his ID, I don’t think there would be any issue. Life is full of chance meetings with other people, and Gary was lucky to meet Steph, as she ended up helping him out of his funk and into becoming Sarah. Another chance meeting with his late wife’s former boss, led to Sarah fulfilling her destiny, and finding a man who loved her and ended up marrying her. Once again, a great story.
Brianna Demonet
Great shoet story. Tragety that ends with love and the holes in both hearts fufilled. It never ceases to amaze me how a little honesty and support can help heal the heart and make a person whole and happy again. Great job Urban!😃😃😃😘😘🥰🥰
