Forty-seven year old Kyle, is a happily married father of one adult daughter who happens to be away in college. He is also the proud owner of two unrestrained Labrador retrievers, one chocolate and one black, that keep him entertained when his wife is away at work. Kyle has been granted the privilege of working from home as a senior software analyst with lots of free time on his hands. With all of his work duties complete for the day, Kyle is drawn to his laptop where he flips it open and pulls up Google. He's has been spending a great deal of time shopping online for items that will help him transform into his alter ego. His fingers dance across the laptop in quick motion as he types "Glamour Boutique" into Google. Glamour Boutique is a website geared toward the crossdressing community. Essentially they are a company that provides women's clothing designed to fit the larger body frames of men. With his shopping cart was rapidly filling up with items, he eyes the black long sleeve miniskirt cocktail dress with a peplum running across the midriff. He thought "Black is slimming and I need as much of that as I can get." He briefly debated purchasing the dress but was eventually sold at the fact that the peplum would also work nicely to conceal his small protruding pooch. Pondering no further, he clicks "Add to Cart" and considers the items he is about to purchase. After ensuring the items be shipped to his P.O. Box, Kyle was now ready to checkout. His cart included a pair of fishnet stockings, a pair of matching bra and panties, a pair of women's size 14 black patent leather Mary Jane pumps with a kitten heel, a synthetic blonde bob wig with fringe bangs, and a few pieces of costume jewelry. The grand total for all of the items came to roughly three hundred dollars not including the tax or shipping and handling. Kyle's new lifestyle was proving to be costly as these were only the first items to be added to his collection of garments.
Kyle, by and large, considered himself a heterosexual male with a kinky fetish for wearing women's clothing and going out in public. It didn't stop there however, although Kyle was attracted to females the need to dress as his alter ego also brought forth desires of sexually satisfying men. How far Kyle's fetish would lead him down the rabbit hole, only time would tell. Up until this point Kyle had only entertained the idea.
A week later Kyle gets an email notification confirming the delivery of his package so the next day while his wife is at work, he dashes down to the post office to retrieve the delivery that he's been anticipating. In a mad rush to get home, all Kyle can think of is that he would now be able to try on his clothes and check himself out as his alter ego. It wouldn't be until he was fully dressed in the clothes that he would give a name to the mysterious lady whom he would become.
Moments later Kyle is bounding up the stairs with the package in hand. Although he is home alone, he slams the door behind him and locks it for safe measure. He rips the box open and carefully lays the contents across his bed. Kyle quickly undressed down to nothing but his white briefs and contemplated the order in which he should put each item on. Of course the panties would be first so he swiftly took his underwear off and replaced them with the soft pearl colored silk panties. They were high waisted, in other words "granny panties." Checking himself out in the mirror he was distracted by the unsightly bulge created by his penis and wondered if it would somehow create a lump on his miniskirt. He'd deal with that issue later and was now delicately lifting the bra from the bed and trying to figure out how to wear it. Luckily for Kyle, it was a bra that clasped in the front. Kyle was in no shape to be able to reach behind him and hook a bra from behind. Now that bra and panties were on he looked himself over again in the floor length mirror next to his bed. The panties were a problem due to the bulge of his penis but now the bra was a problem because it looked like two deflated bags. Kyle would need to stuff the bra so that his titties would sit up nice and perky as he'd imagined they should be. He then methodically put on the fishnet stockings being careful not to snag them. The undergarments were in place and now Kyle was putting on the cocktail miniskirt. He brought the skirt down over his head as he would a t-shirt and tugged it into place so that the seams were straight on either side. He quickly tossed his heels on and nervously walked over to the mirror again to see his creation coming to life. With a few quick spins and angle checks, Kyle was dying to put the jewelry and wig on to see who he would become. Grace was born the moment Kyle spoke the words "Hello...Grace" to his new reflection (As to not confuse the reader, Kyle will be referred to as Grace in the later portion of the story).
As fast as Kyle had put the clothes on, he was now carefully removing them and neatly placing them in an old suitcase that he kept in the back of his closet. He and his wife had separate closets which was perfect because his wife never stepped foot in his closet therefore she would never find his stash. He knew this to be true because he'd been stashing pornographic magazines in there for years and she'd never discovered them.
Kyles stash would remain untouched for 2 weeks time. The amount of time before his wife would be taking a week long trip to visit her elderly mother in Florida. His plan to introduce Grace to the world was devised to happen once his wife was out of town. Kyle chomped at the bits while waiting for the 2 weeks to come so that he could pull that suitcase out of his closet and don his feminine attire. Those two weeks had gone by and Kyles wife was on a plane headed to Florida. That morning he'd shaved his facial hair and tried his best to shave as much of his body hair as he possibly could. He'd made plans to get his feet wet as Grace by going down to distant honky tonk a few towns over. He felt assured that if he travelled a good distance away he could test the waters as Grace without anyone he knew recognizing him.
It was 9 o'clock that night, the time had come for Kyle to become Grace and go out in public for the first time. This would be a test run for Kyle. Just as he'd done the first time, Kyle put the garments on in the same order. His wig was the cherry on top and now he needed a little something extra to feel like the woman he wanted to be. He went into the bathroom and perused his wife's vanity in search of some cosmetics that would make Grace look more glamorous. "I have no clue what any of this stuff is and how it should be applied." He did recognize the tube of his wife's favorite red lipstick and quickly put it on. Not knowing what anything else was he figured the lipstick would serve a double purpose so he made two round dots on the apples of his cheeks and rubbed them around to create blush. He felt his eyes needed something more to make them more feminine so he found a makeup pallet with an array of colors and he decided the blue would compliment his brown eyes. He swiped a streak of blue across either eye and blended them as best he could. Looking at himself in the mirror he felt his eyes still needed a little something more so he grabbed a black pencil from the vanity and with unsteady hands he traced the outline of his eyes to give himself a dark rim. Before leaving the restroom he picked up a bottle of his wife's favorite perfume, Elizabeth Taylor's White Diamond, and he sprayed himself on his wrists, his chest, and between his thighs. With one last inspection of himself in the mirror, Kyle was satisfied and slightly turned on by the woman he saw before him. "I think this sexy woman should have a purse." He knew that his wife had a bunch of old unused purses that she'd collected over time, so he simply went to his wife's closet and found a small black sequined clutch purse that would hold money, breath mints, and ID. Kyle was now ready to hop in his truck and drive the one hour drive to "Tootsie's Pool Hall & Lounge."
The drive there was spent with Kyle getting into character as Grace. He needed to check his voice and remember to soften his mannerisms. His wife and mother would be his female inspirations. After an hour of driving, Kyle pulls into the gravel parking lot of "Tootsie's Pool Hall & Lounge." It didn't look too rowdy which eased his mind. He stepped into the joint as Grace. It was dark and dusky and there was a lot of chatter throughout the room. He spotted an empty seat at the bar and grabbed it. A bartender who introduced himself as Moe asked "What can I get for you ma'am?" Kyle beamed inside thanks to the bartender not clocking him as a man in a wig. He didn't know if he was passable or if it was the dim lighting that caused the bartender to see him as a "ma'am." It didn't really matter though because the boost of confidence he'd gained caused him to open up more. Kyle had a few drinks then headed out to the dance floor. The drinks had provided Kyle the liquid courage he needed to step on the dance floor which was lit from above by overhead spotlights. Kyle was nobody's dancer but he knew he could do a simple two-step to the beat without looking like a complete clown.
Two songs in and Kyle was starting to get winded when suddenly a hulking figure in a cowboy hat approached. Kyle could only see the silhouette of the figure because the lights were haloing him from behind but from the looks of his figure he was tall with broad shoulders and huge biceps. "Hey there purdy lady! I was watching you from across the room and you sure know how to move." Kyle checked his voice before speaking and meekly uttered a thank you to the compliment. Kyle was getting a little nervous because although he'd had desires about men coming on to him, he never really considered what he would do should it actually happen. Was he safe should this man discover Kyle to be a man? Kyle would soon have his answer. "My name is Jeffrey... and you are?" Kyle nervously introduced himself for the first time as "I'm Grace." Pleasantries aside, Jeffrey had an agenda. "Grace would you like to join me in my camper? It's parked out back." Kyle as Grace said "Sure, why not?"
Kyle awkwardly traversed the gravely parking lot in his kitten heels, careful not to twist his ankle on the uneven rocky surface. Jeffrey as sure footed as he could be in his gator boots, lead the way in silence. The compact vintage camper that was hitched to a pickup truck was finally in front of them. Jeffrey unlocked the door and invited "Grace" to step inside before him. He pulled the draw string to a light switch that hung from the ceiling and the camper was illuminated in warm light. "Grace, watching you dance really did something for me. I love a tall woman with courage." Kyle blushed at this but said nothing. Jeffrey could see that his charm was working and he would eventually get down to the true reason he'd invited "Grace" back to his camper. "Grace can I ask a favor of you sweetheart?" Kyle started to get goose bumps in knowing that Jeffrey was about to seduce him with a sexual request. "What is it?" Jeffrey could see it in "Grace's" eyes that she was a woman ready for action. "Grace, there's something about those bright red lips and that shiny blond hair, it turns me on." As Jeffrey is saying these things he is also becoming more touchy feely as he slowly brings his thumb up to "Grace's" lower lip and gently rubs it. "Grace" falling for the seduction licks his thumb several times before opening the mouth wider. For a minute or two "Grace" passionately sucks Jeffrey's thumb imagining it was his cock instead. Jeffrey's penis was doubling in size beneath his Wranglers but "Grace" would not know this until Jeffrey grabbed "Grace's" hand and placed it at his groin. While feeling Jeffrey's burgeoning boner, Kyle began to get a boner of his own. "Grace put your mouth on it sweetheart. Do what you were doing to my thumb and make my dream come true." Kyle received the invitation that he'd been hoping for. Never had Kyle given a man a blowjob but in many of his sexually charged dreams, Grace was a slutty harlot and she was a certified deepthroat diva." Kyle was about live out a fantasy of his own and suck a cock for the first time.
Kyle removed the rings and bracelets as he prepared for the task at hand. He then got down on his knees as Jeffrey planted his feet firmly with ample enough space for Grace to show him what she was made of. Jeffrey went to undo his belt buckle and unzip his jeans when Grace took over the job. "Let me take care of that for you." Jeffrey's pants and underwear were lowered to just above his knees and Grace was met face to face with Jeffreys thick 8 inch erection which bobbed up and down as blood pumped through it. Kyle had never been this close to another man's erect penis before but in his imagination Grace had handled many of them. The banana shaped cock which pointed downward was aligned perfectly to slide down the path of Grace's eagerly awaiting esophagus. Something else that Grace had noticed was the thick curly brown hair that encircled Jeffrey's shaft. Jeffrey had not been seen without his cowboy hat, so it was never known if Jeffrey was blond or brunette until this moment. Wasting no more time, Grace got down to work and encapsulated Jeffrey's warm member within her spacious mouth. She knew to start off slowly so that Jeffrey could enjoy the sensation of a warm wet mouth gently caressing his cock from the tip of the head to the base of the shaft. For five long minutes she passionately bobbed back and forth against Jeffrey's delicious dick. Jeffrey was pleased but Grace felt it was time to step things up a notch. She increased the pace and introduced a cupped hand to the underside of Jeffrey's gyrating balls. Holding Jeffrey's balls gave her the idea to gently suck them but before she would do that she would be sure to take her free hand and stroke his cock so that the erection would hold it's firmness. As Grace was sucking Jeffries balls she discovered that this was a sweet spot for him as he moaned louder to this new and pleasant sensation. Grace understood that she would bring Jeffrey to climax simply from sucking his balls and sure enough his scrotum tightened into a firm knot against the base of his shaft and a stream of thick milky cum shot across her face where some of it landed in the fringe of her wig. Once the load was extracted and Jeffrey's cock began to deflate, Grace released her mouth from Jeffrey's tightened balls. Jeffrey was momentarily at a loss for words. After gaining his ground from wobbly legs, Jeffrey showered Grace with compliments on a job well done. "Amazing, Grace... simply amazing."
On the drive home, Kyle was pleased with his first excursion as Grace and knew that there would be many more to come. "I think I like Amazing Grace better."
Kyle, by and large, considered himself a heterosexual male with a kinky fetish for wearing women's clothing and going out in public. It didn't stop there however, although Kyle was attracted to females the need to dress as his alter ego also brought forth desires of sexually satisfying men. How far Kyle's fetish would lead him down the rabbit hole, only time would tell. Up until this point Kyle had only entertained the idea.
A week later Kyle gets an email notification confirming the delivery of his package so the next day while his wife is at work, he dashes down to the post office to retrieve the delivery that he's been anticipating. In a mad rush to get home, all Kyle can think of is that he would now be able to try on his clothes and check himself out as his alter ego. It wouldn't be until he was fully dressed in the clothes that he would give a name to the mysterious lady whom he would become.
Moments later Kyle is bounding up the stairs with the package in hand. Although he is home alone, he slams the door behind him and locks it for safe measure. He rips the box open and carefully lays the contents across his bed. Kyle quickly undressed down to nothing but his white briefs and contemplated the order in which he should put each item on. Of course the panties would be first so he swiftly took his underwear off and replaced them with the soft pearl colored silk panties. They were high waisted, in other words "granny panties." Checking himself out in the mirror he was distracted by the unsightly bulge created by his penis and wondered if it would somehow create a lump on his miniskirt. He'd deal with that issue later and was now delicately lifting the bra from the bed and trying to figure out how to wear it. Luckily for Kyle, it was a bra that clasped in the front. Kyle was in no shape to be able to reach behind him and hook a bra from behind. Now that bra and panties were on he looked himself over again in the floor length mirror next to his bed. The panties were a problem due to the bulge of his penis but now the bra was a problem because it looked like two deflated bags. Kyle would need to stuff the bra so that his titties would sit up nice and perky as he'd imagined they should be. He then methodically put on the fishnet stockings being careful not to snag them. The undergarments were in place and now Kyle was putting on the cocktail miniskirt. He brought the skirt down over his head as he would a t-shirt and tugged it into place so that the seams were straight on either side. He quickly tossed his heels on and nervously walked over to the mirror again to see his creation coming to life. With a few quick spins and angle checks, Kyle was dying to put the jewelry and wig on to see who he would become. Grace was born the moment Kyle spoke the words "Hello...Grace" to his new reflection (As to not confuse the reader, Kyle will be referred to as Grace in the later portion of the story).
As fast as Kyle had put the clothes on, he was now carefully removing them and neatly placing them in an old suitcase that he kept in the back of his closet. He and his wife had separate closets which was perfect because his wife never stepped foot in his closet therefore she would never find his stash. He knew this to be true because he'd been stashing pornographic magazines in there for years and she'd never discovered them.
Kyles stash would remain untouched for 2 weeks time. The amount of time before his wife would be taking a week long trip to visit her elderly mother in Florida. His plan to introduce Grace to the world was devised to happen once his wife was out of town. Kyle chomped at the bits while waiting for the 2 weeks to come so that he could pull that suitcase out of his closet and don his feminine attire. Those two weeks had gone by and Kyles wife was on a plane headed to Florida. That morning he'd shaved his facial hair and tried his best to shave as much of his body hair as he possibly could. He'd made plans to get his feet wet as Grace by going down to distant honky tonk a few towns over. He felt assured that if he travelled a good distance away he could test the waters as Grace without anyone he knew recognizing him.
It was 9 o'clock that night, the time had come for Kyle to become Grace and go out in public for the first time. This would be a test run for Kyle. Just as he'd done the first time, Kyle put the garments on in the same order. His wig was the cherry on top and now he needed a little something extra to feel like the woman he wanted to be. He went into the bathroom and perused his wife's vanity in search of some cosmetics that would make Grace look more glamorous. "I have no clue what any of this stuff is and how it should be applied." He did recognize the tube of his wife's favorite red lipstick and quickly put it on. Not knowing what anything else was he figured the lipstick would serve a double purpose so he made two round dots on the apples of his cheeks and rubbed them around to create blush. He felt his eyes needed something more to make them more feminine so he found a makeup pallet with an array of colors and he decided the blue would compliment his brown eyes. He swiped a streak of blue across either eye and blended them as best he could. Looking at himself in the mirror he felt his eyes still needed a little something more so he grabbed a black pencil from the vanity and with unsteady hands he traced the outline of his eyes to give himself a dark rim. Before leaving the restroom he picked up a bottle of his wife's favorite perfume, Elizabeth Taylor's White Diamond, and he sprayed himself on his wrists, his chest, and between his thighs. With one last inspection of himself in the mirror, Kyle was satisfied and slightly turned on by the woman he saw before him. "I think this sexy woman should have a purse." He knew that his wife had a bunch of old unused purses that she'd collected over time, so he simply went to his wife's closet and found a small black sequined clutch purse that would hold money, breath mints, and ID. Kyle was now ready to hop in his truck and drive the one hour drive to "Tootsie's Pool Hall & Lounge."
The drive there was spent with Kyle getting into character as Grace. He needed to check his voice and remember to soften his mannerisms. His wife and mother would be his female inspirations. After an hour of driving, Kyle pulls into the gravel parking lot of "Tootsie's Pool Hall & Lounge." It didn't look too rowdy which eased his mind. He stepped into the joint as Grace. It was dark and dusky and there was a lot of chatter throughout the room. He spotted an empty seat at the bar and grabbed it. A bartender who introduced himself as Moe asked "What can I get for you ma'am?" Kyle beamed inside thanks to the bartender not clocking him as a man in a wig. He didn't know if he was passable or if it was the dim lighting that caused the bartender to see him as a "ma'am." It didn't really matter though because the boost of confidence he'd gained caused him to open up more. Kyle had a few drinks then headed out to the dance floor. The drinks had provided Kyle the liquid courage he needed to step on the dance floor which was lit from above by overhead spotlights. Kyle was nobody's dancer but he knew he could do a simple two-step to the beat without looking like a complete clown.
Two songs in and Kyle was starting to get winded when suddenly a hulking figure in a cowboy hat approached. Kyle could only see the silhouette of the figure because the lights were haloing him from behind but from the looks of his figure he was tall with broad shoulders and huge biceps. "Hey there purdy lady! I was watching you from across the room and you sure know how to move." Kyle checked his voice before speaking and meekly uttered a thank you to the compliment. Kyle was getting a little nervous because although he'd had desires about men coming on to him, he never really considered what he would do should it actually happen. Was he safe should this man discover Kyle to be a man? Kyle would soon have his answer. "My name is Jeffrey... and you are?" Kyle nervously introduced himself for the first time as "I'm Grace." Pleasantries aside, Jeffrey had an agenda. "Grace would you like to join me in my camper? It's parked out back." Kyle as Grace said "Sure, why not?"
Kyle awkwardly traversed the gravely parking lot in his kitten heels, careful not to twist his ankle on the uneven rocky surface. Jeffrey as sure footed as he could be in his gator boots, lead the way in silence. The compact vintage camper that was hitched to a pickup truck was finally in front of them. Jeffrey unlocked the door and invited "Grace" to step inside before him. He pulled the draw string to a light switch that hung from the ceiling and the camper was illuminated in warm light. "Grace, watching you dance really did something for me. I love a tall woman with courage." Kyle blushed at this but said nothing. Jeffrey could see that his charm was working and he would eventually get down to the true reason he'd invited "Grace" back to his camper. "Grace can I ask a favor of you sweetheart?" Kyle started to get goose bumps in knowing that Jeffrey was about to seduce him with a sexual request. "What is it?" Jeffrey could see it in "Grace's" eyes that she was a woman ready for action. "Grace, there's something about those bright red lips and that shiny blond hair, it turns me on." As Jeffrey is saying these things he is also becoming more touchy feely as he slowly brings his thumb up to "Grace's" lower lip and gently rubs it. "Grace" falling for the seduction licks his thumb several times before opening the mouth wider. For a minute or two "Grace" passionately sucks Jeffrey's thumb imagining it was his cock instead. Jeffrey's penis was doubling in size beneath his Wranglers but "Grace" would not know this until Jeffrey grabbed "Grace's" hand and placed it at his groin. While feeling Jeffrey's burgeoning boner, Kyle began to get a boner of his own. "Grace put your mouth on it sweetheart. Do what you were doing to my thumb and make my dream come true." Kyle received the invitation that he'd been hoping for. Never had Kyle given a man a blowjob but in many of his sexually charged dreams, Grace was a slutty harlot and she was a certified deepthroat diva." Kyle was about live out a fantasy of his own and suck a cock for the first time.
Kyle removed the rings and bracelets as he prepared for the task at hand. He then got down on his knees as Jeffrey planted his feet firmly with ample enough space for Grace to show him what she was made of. Jeffrey went to undo his belt buckle and unzip his jeans when Grace took over the job. "Let me take care of that for you." Jeffrey's pants and underwear were lowered to just above his knees and Grace was met face to face with Jeffreys thick 8 inch erection which bobbed up and down as blood pumped through it. Kyle had never been this close to another man's erect penis before but in his imagination Grace had handled many of them. The banana shaped cock which pointed downward was aligned perfectly to slide down the path of Grace's eagerly awaiting esophagus. Something else that Grace had noticed was the thick curly brown hair that encircled Jeffrey's shaft. Jeffrey had not been seen without his cowboy hat, so it was never known if Jeffrey was blond or brunette until this moment. Wasting no more time, Grace got down to work and encapsulated Jeffrey's warm member within her spacious mouth. She knew to start off slowly so that Jeffrey could enjoy the sensation of a warm wet mouth gently caressing his cock from the tip of the head to the base of the shaft. For five long minutes she passionately bobbed back and forth against Jeffrey's delicious dick. Jeffrey was pleased but Grace felt it was time to step things up a notch. She increased the pace and introduced a cupped hand to the underside of Jeffrey's gyrating balls. Holding Jeffrey's balls gave her the idea to gently suck them but before she would do that she would be sure to take her free hand and stroke his cock so that the erection would hold it's firmness. As Grace was sucking Jeffries balls she discovered that this was a sweet spot for him as he moaned louder to this new and pleasant sensation. Grace understood that she would bring Jeffrey to climax simply from sucking his balls and sure enough his scrotum tightened into a firm knot against the base of his shaft and a stream of thick milky cum shot across her face where some of it landed in the fringe of her wig. Once the load was extracted and Jeffrey's cock began to deflate, Grace released her mouth from Jeffrey's tightened balls. Jeffrey was momentarily at a loss for words. After gaining his ground from wobbly legs, Jeffrey showered Grace with compliments on a job well done. "Amazing, Grace... simply amazing."
On the drive home, Kyle was pleased with his first excursion as Grace and knew that there would be many more to come. "I think I like Amazing Grace better."
