Kaitlyn

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(Saturday, Dec. 14, 2013)Mitch was expecting someone. He paced his living room floor nervously, anticipating the person?s arrival. As he took another step, he wobbled and nearly turned an ankle. ?Stupid heels,? he muttered. He was still getting used to walking in high heels. He?d just put them on about fifteen minutes ago. He glanced down at the high heeled sandals, his exposed feet and his red, painted toenails. Is this for real? He asked himself.*He heard the sound of a car door slam. His heart raced uncontrollably. He practically ran to the window (at least, as fast as he could in the heels). He carefully lifted up the blinds and peeked out. Nope, just the neighbors. He breathed a sigh of relief. Maybe he won?t show up, he thought, almost hopefully.*The still somewhat mysterious stranger was due to arrive any second. Mitch had no idea what the guy looked like. Well, that wasn?t entirely true. He knew what Kaitlyn looked like, but he didn?t know what Todd looked like.*Deciding that he needed to relax, Mitch smoothed out and straightened his little black dress as he sat down on his couch and tried to calm himself. Ahhh, my couch, he thought to himself, my magical couch. He had never quite understood what it was about that couch, but for some reason, women really liked it?in more ways than one. Perhaps its luck would hold out tonight as well.*He crossed his smoothly shaved legs as he ran one hand across the couch?s fabric. While doing so, he pondered the situation. What?s going to happen this evening? How?s this going to turn out? What are we going to talk about? What if we don?t have anything in common at all? He hated it when so many variables were up in the air. Ugh, how did I ever let myself get talked into this mess?*It had all started one evening, while under the influence of alcohol, Mitch had admitted to his wife, Misty, that he had once dabbled in crossdressing in his younger, more adventurous days.*?What? Seriously?? Misty questioned, her face brightening instantly.*?It was a long time ago,? Mitch sort of lied, after all, it had been much more recently than he cared to admit. ?I gave it up years ago.?*?Why?!? the petite redhead asked aggressively.*?What do you mean?? Mitch replied, suddenly feeling a twinge of apprehension.*?That?s so hot,? Misty explained. ?You shouldn?t have given it up.?*?You mean you want me to?? Mitch started.*?Yes!? Misty burst out. ?Are you kidding?! That would be amazing to see you like that.?*?But I don?t have the body I used to,? Mitch complained, grabbing his gut.*?Trust me, honey,? Misty retorted, ?your body is still way better than most women.?*The next step involved Mitch figuratively dusting off some ancient digital pictures. Pictures that had been buried in a file deep on his computer. A file within a file within a file, to be exact. Pictures that he had sworn to himself would never see the light of day again. Yet, at the same time, pictures that he had never been able to bring himself to click ?delete? on.*He showed his wife the images, or at least, the better ones, and with each one, Misty became increasingly giddy. ?These are awesome!? she said through a fit of laughter.*Mitch squirmed. He was showing Misty a part of himself that he had put in his past?a part of himself that, in some ways, he was almost ashamed of. He started to feel embarrassed. ?Are you laughing at me?? he asked, trying to sound lighthearted. ?I can?t tell if you?re really enjoying this, or if you?re just laughing at how ridiculous I look in these pictures.?*Misty, knowing her husband as well as she did, must have heard the edge in his voice. She immediately stopped laughing and threw her arms around Mitch?s shoulders. ?No, dear God, no, I?m not laughing at you,? she apologized. ?I?m just overjoyed. I had no idea. I wish you had told me this years ago.?*Mitch huffed, still uncertain.*?And you don?t look ridiculous,? Misty encouraged. ?In fact,? she continued, glancing at the computer screen once more, ?you?re actually pretty hot.?*?You think so?? Mitch replied, his attitude warming a bit.*?Oh yeah,? Misty answered in a sexy voice. ?Nice isvecbahis (https://isvecbahis.live/) legs?really nice,? she added. ?So, who took these pictures??*?Oh, some of them I took myself,? Mitch admitted, clicking open another folder, and bringing a few more of the images on the screen. ?The others, Heather and Tracy took.?*?Of course, Heather and Tracy,? Misty repeated. ?Love those two girls,? she said honestly. ?So, was it their idea??*?Was what their idea?? Mitch asked.*?You crossdressing?? Misty explained. ?Did they talk you into it??*Mitch snickered and grinned sheepishly. ?Well, now that you mention it, it was their idea, originally.?*?Originally?? Misty questioned, raising her eyebrows.*?Yeah,? Mitch answered. ?They practically forced me to, the first time, but I really enjoyed it. So, after that, I didn?t need any encouragement.?*?Interesting,? Misty said, raising an eyebrow. ?So, where all did you?go?like this?? she asked, pointing to the screen.*Mitch shrugged. ?A couple of parties. A few smaller get-togethers for like-minded individuals. Pretty safe environments.? He paused for a moment and then added, ?I mean, it?s not like I was walking around Walmart dressed like this.?*Over the course of the next several weeks, Misty continued applying subtle pressure to Mitch, encouraging him that he should renew his old? hobby. Mitch resisted, but ultimately, his resistance was futile. Misty just wouldn?t take no for an answer. She desperately wanted to see her man as, well, a woman.*Finally, he consented. They had gone online together and purchased all the necessary items. Bra, panties, high heels, a wig, a nice little black dress that concealed all the right spots, but was short in all the right places. Misty helped him measure, to ensure that they got the right sizes. As they ordered, Mitch began to realize just how much bigger he was.*?I used to wear size 5 panties?now I?m a size 7 or 8?!? he said in disbelief.*Misty just shrugged. ?You were like twenty-two when you wore size 5, now you?re thirty-six?it happens.?*The items arrived and the big night finally came. Mitch locked himself in the bathroom. After a couple of hours of shaving, he did his makeup as best he could with his limited abilities, changed, and revealed himself to his wife for the first time. She absolutely loved it and they had a really fun night together (in all sorts of ways).*Since then, they had played dress-up several times and she?d even convinced Mitch to go to a Halloween party that was attended by very open-minded people. Misty found it entertaining?not to mention arousing?to buy new items for Mitch, and as a result, his wardrobe had expanded quite a bit.*Through their exploration and self-discovery, Misty began to understand that her husband?s natural bisexual nature had been suppressed for far too long. She?d always known he was a bisexual, pretty much since the moment they had met. Even their first sexual encounter had been a bisexual experience for Mitch?a threesome involving her then-husband, Justin.*She began to realize, however, that in their four years of marriage, their sex life had been rather pedestrian. They had great sex, and both of them truly enjoyed it?but she was now seeing just how much she had been unintentionally restraining Mitch?s sexuality. So, one evening, she just asked him.*?Mitch, do you want to have sex with a guy?? she said bluntly.*?Wh-what?? Mitch stammered, totally not expecting the question and nearly dropping the book he had been reading.*?Did I stutter?? Misty joked. ?I thought it was a pretty straightforward question. Do you want to have sex with a guy??*?There?s nothing straight about that question,? Mitch quipped.*Misty rolled her eyes. ?You know what I mean,? she countered.*?N-no,? Mitch began to reply cautiously. ?No, not really, why do you ask?? As he said the words, he lifted the book back up, trying to look disinterested.*?Oh, come on, Mitch,? she prodded. ?You know you do. Don?t be embarrassed by it. I know you?re bi. Don?t forget, I?ve watched you suck another man?s cock.?*Mitch set the book down once more. ?But, we?re married?? he countered.*?Oh, isveçbahis giriş (https://isvecbahis.live/) boo-hoo,? Misty shot back. ?That shouldn?t stop you. I was married the first time you had sex with me. You and I have shared the same woman before. I?ve been with a woman by myself since we?ve been married. You know that, and I told you every detail about it. So, why shouldn?t you be able to be with a man??*Mitch searched for an answer, ?Because??*?Because nothing,? Misty filled in the blank. ?You?re holding yourself back.? She reached over and wrapped her arms around him, resting her head against his chest. ?And aside from that, I?m missing out too! If you did that, I would want to hear all the juicy details!? She sighed, massaging his chest with one hand. ?Soooo, do you wanna fuck a dude or not??*Mitch placed a comforting hand on his wife?s shoulder. ?First off, you?re right. You know I?m bisexual. But,? he chuckled, ?You also know that I wouldn?t ever ?fuck a dude.??*Misty laughed. ?Oh, all right?damn, you really are half-woman sometimes,? she joked. ?Allow me to rephrase myself then. Do you want a dude to fuck you or not??*Mitch snorted with laughter. He thought about it for a moment and then finally responded, ?I have to admit, it does have a certain appeal to me. And, besides, it has been a really long time.?*So, the next question became?who? Neither of them had any friends who were into that sort of thing?at least, not that they knew about. Coworkers? No, definitely not. Long-lost acquaintances that they used to know? Probably best not to light up an old flame, they decided. They finally settled on the next best option. The internet.*?After all, it?s a brave new world,? Misty said, as she typed in a key phrase into that popular search engine that rhymes with doogle. ?Lots of people are using the internet to find romantic partners these days, right??*?Please don?t use that word,? Mitch said with a grimace.*?What word?? Misty teased, ?internet??*?No,? Mitch returned, ?romantic. I am certainly not looking for a romantic partner.?*?Would you rather I say ?fuck buddy?'? Misty returned.*?Umm, well, yes, actually,? Mitch replied, chuckling.*They found a website that catered to Mitch?s particular interests (no, it?s not that one?no, not that one either) and created a profile for him. They posted several pictures of him?or, that is to say?they posted several pictures of his female persona, whom they had been referring to as Nicole (named after an old crush of Mitch?s from many years ago). Then, they waited.*Within days, several men began showing interest. Most, they would both take one look at the other man?s profile and immediately say, ?No.? Some were disturbing. A few were downright frightening. Finally, after several weeks, one young man seemed to show genuine interest in Mitch.*He was about twenty-eight and he too was a crossdresser. All of the images posted to his profile were of his female character, whom he referred to as ?Kaitlyn?. He?or she??lived close by, and most importantly, didn?t come across like a potential serial killer.*In other words, he had never sent them an unsolicited picture of his dick. He had never sent a message implying that he had just jerked off to Nicole?s pictures. He had never sent a message talking about how much he wanted to cum all over Nicole?s face. And he had never referenced tying anyone up or using whips and chains. (Yes, these were all things that other respondents had done). By comparison, Kaitlyn seemed downright normal.*They took their time. Over the next several months, they sent messages back and forth to one another, through the website at which they had met. Each day, both Mitch and Misty eagerly came home, excited to read the next message. They learned enough about him to know that yes, he was genuinely interested, he seemed mentally stable, and discretion*was as important to him as it was to Mitch. After all, Mitch had been a teacher in this community for many years. If something like this ever got out, it could ruin him.*?I think it?s time,? Misty said one evening.*?Time for what?? Mitch replied.*?I think it?s isveçbahis yeni giriş (https://isvecbahis.live/) time for Nicole to meet Kaitlyn.?*?Ohhhh,? Mitch answered, understanding what his wife meant. He thought about it for a moment and then added, ?I agree. I think it?s time.?*So, with nervous fingers, Mitch typed out the message, asking Kaitlyn if she wanted to meet. They picked a time and agreed that a suitable place would be Mitch and Misty?s home. Misty volunteered to go visit her parents that evening and stay the night. That way, regardless of how the evening went, she wouldn?t be at risk of interrupting anything.*The big day finally arrived. Mitch shaved his legs, his underarms, his crotch, his chest, his ass?even his arms. After all, it was the middle of winter, and no one would see his arms until next spring. Misty helped him apply his makeup, both of them wanting it to look as perfect as possible for such a big night. Then, Mitch slithered into the tight, form-fitting black dress they had bought just for the occasion. The last step was the wig. He placed it on his head, and gently ran his fingers through, making it look just right.*?You look incredible,? Misty remarked, appraising her husband as he checked himself out in the mirror.*?You think?? Mitch asked, completely unsure of himself.*?My beautiful Nicole,? Misty said teasingly, ?you have nothing to worry about. You?re gorgeous.? As she spoke, she playfully slapped him on the ass. ?Good luck,? she added with a smile. ?Who knows, if things go really well, maybe I?ll join in the next time.?*A moment later, she said goodbye and left Mitch alone to await Kaitlyn?s arrival. So, there he was, sitting on the couch, legs crossed, just minutes before seven o?clock, the designated time he was supposed to arrive.*He? Mitch considered the term curiously. She?? There was no doubt, it was a man that would be arriving. I don?t even know his last name! Mitch thought. A dozen other horrifying thoughts flashed through his mind. What if this is some kind of elaborate setup? And someone is just trying to make a fool out of me? What if he really is some kind of crazy lunatic? It even occurred to him that Kaitlyn could be a former student. He had students that were the same age. But no, he tried to reassure himself, he and Misty had asked enough probing questions to make sure that none of those things were true.*He raised himself from the couch, and stepped into the kitchen, just to check the necessary supplies one more time. Rum? Check. Bottles of Coke? Check. Beer? Check. Just then, the doorbell rang.*Mitch?s mind raced. He hadn?t heard a car drive up. He hadn?t heard a door slam. His heart hammered inside his chest. His palms suddenly became very sweaty. He raced to the front window and peeked out, just as he had before. In his driveway, sat a big, black, dirty, four-door Dodge Ram. What? Mitch thought, that doesn?t seem right.*He peeked the other direction. Standing at the door, was a short, stalky young man, who appeared to be about the right age, holding a big black bag at his side. Mitch took a deep breath and adjusted his false breasts one more time. He reached for the doorknob, his hand trembling. The last thought that went through his mind as he turned the knob was, Oh dear God, please don?t let this be a pizza delivery guy who got the wrong address.*Mitch pulled the door open and quietly greeted his guest. He pushed open the screen door, yet cautiously stood back, out of the door frame, so that curious neighbors couldn?t see him dressed as Nicole.*?Hi, I?m Todd,? the man greeted, introducing himself. Mitch quickly closed the door behind him, glancing each direction outside as he did so. They shook hands, a rugged, firm handshake, and they spoke for only a moment. It was, without a doubt, the most awkward exchange of Mitch?s life. He was standing in the middle of his living room, wearing a dress, a wig, and high heels?and he was talking to a complete stranger. Yet, on some level, he had actually ?known? this person for several months.*The mysterious stranger, Todd, was absolutely nothing like Mitch had anticipated. He was, for lack of a better way to describe him, a roughneck. He talked with a slow, Southern drawl, wore a baseball cap, and had a toothpick in his mouth. His lower lip protruded, in the telltale manner of one who normally dips snuff.