(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 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, 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 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.
This has to be some mistake, right? Mitch said to himself. There is no way this is the guy that I saw in those pictures. He is so unlike me—there’s no way this will work. In fact, Mitch’s initial reaction to his visitor was so offsetting, that he was on the verge of admitting that this had all been a terrible mistake, and asking him to leave.
But then, just as Mitch was about to say the words, Todd hoisted his black bag and said, “So, where do I change? I’m sure we’ll both be more comfortable after that.”
Mitch forced himself to continue with the planned evening. He showed the newcomer to the bathroom. Todd entered with his black bag, said, “I’ll see you in a few minutes,” and shut the door behind him.
The next half-hour was nerve-racking. Mitch tried to make himself comfortable, sitting down in a chair and crossing his legs. He ran a hand across them and gauged their smoothness. He suddenly realized how much skin the little outfit showed off. Standing back up, he paced around the living room, his hands clasped behind him. He was a nervous wreck. A single drop of sweat rolled from his underarm and down his bicep.
What could they possibly talk about for the entire evening? Mitch thought. Guys like that aren’t crossdressers, are they? This could be an utter disaster? We couldn’t possibly have anything in common. The bathroom door opened.
Mitch turned and his jaw dropped. Standing in front of him was—well, Kaitlyn. The woman from all the pictures on her profile. In thirty minutes, this crude, stalky, tobacco-chewing roughneck had somehow managed to transform himself into an attractive woman. If Mitch hadn’t known better, he would have sworn it was not the same human being.
Kaitlyn wore a simple, but tight, sleeveless red dress that cut off at mid-thigh. Her legs were bare and she wore high heel pumps. Her makeup was expertly done and a blonde, curly wig completed the metamorphosis.
Kaitlyn stepped across the room and introduced herself for the second time that evening. “Hi, I’m Kaitlyn,” she said. Even the voice had changed. She offered her hand and they shook hands once more. A gentle, feminine handshake.
“Hi,” Mitch said, “I’m Nicole.” His voice could barely get the name out. He had never introduced himself—to anyone—by that name. It was merely a name he and Misty had used for his online profile.
“It’s so nice to finally meet you,” Kaitlyn responded.
“You too,” Mitch answered. “You look amazing,” he blurted out.
“So do you,” Kaitlyn said, reaching out and holding Mitch’s hands in a very girlish fashion. “Even better than in your pictures.”
“Have a seat,” Mitch encouraged, motioning towards the sofa. “Would you like a drink?”
“Sure, that sounds great,” Kaitlyn said as she made her way to the couch.
Mitch went to the kitchen and poured two glasses full of coke. He added a generous portion of rum to each one and carried both into the living room. Kaitlyn had made herself comfortable on the middle cushion—meaning Mitch had no choice but to sit right next to her.
He handed one drink to Kaitlyn and then sat down next to her. They each took a sip of the strong beverages. As he took the drink away from his lips, Mitch couldn’t help but notice the lipstick stain that each of them had left on the edge of the glass.
“Nice couch,” Kaitlyn remarked, sliding one hand across the fabric. “I love this upholstery.”
“Thanks,” Mitch responded through a slight chuckle.
“So,” Kaitlyn started, “how long have you been dressing?” she asked as a way of breaking the ice.
Mitch explained his on-again, off-again history with women’s clothing. “How about you?”
Kaitlyn smiled a pretty smile. “Pretty much since I was seventeen or eighteen.”
In just a few minutes, they were talking to each other with ease. They exchanged stories about how they first got started dressing as women and also talked about why they chose their female names. As they chatted, Mitch realized that he had overlooked one important fact. He had assumed that the two of them would have nothing in common. In reality, he understood that they had one very major thing in common and it bonded the two of them together instantly.
They discovered that they actually shared some acquaintances. In a town of that size, it wasn’t surprising. They discussed privacy and how important it was for each of them to remain quiet about the evening’s activities. Mitch revealed his occupation and how damaging it could be if anyone else found out.
Kaitlyn revealed that it would be pretty damaging for her as well. As it turns out, she was not a roughneck. She actually worked for the city as part of the sanitation crew. “If the other guys ever saw me like this,” she remarked, “they’d probably beat the shit out of me.”
After a moment of laughter, a question occurred to Mitch. “Have you ever been caught?” he asked.
“Oh, sure,” Kaitlyn answered lightheartedly, placing a hand on Mitch’s knee. “Who hasn’t been caught?” She inched closer so that their bare thighs were now in contact with each other. “My mom caught me fully dressed one time—I was still living with my parents and she came home when I least expected it. Quite a way for her to find out, let me tell you.”
Nearly an hour later, their drinks had been emptied, refilled, and emptied again. All of Mitch’s earlier uneasiness had completely vanished. He had to admit to himself that he was having a good time. He leaned back, resting against the couch. He stretched his arms out, placing one hand across the top of the sofa. The air felt good on his cleanly shaven underarms.
Kaitlyn reached up and delicately stroked Mitch’s arm. “Bold step, shaving your forearms,” she said, sliding her hands all the way to Mitch’s bare shoulder.
They were now gazing at each other intently. Mitch suddenly felt a lump in his throat. The mood had definitely taken a sudden shift.
“Did you invite me over here to talk all night?” Kaitlyn said in a sultry voice.
“Not exactly,” Mitch responded.
Kaitlyn was already making her move. She leaned in and kissed Mitch on the lips. A moment later, her tongue was inside his mouth. Mitch had not kissed another man in years. He had always found the sensation rather odd. Despite her feminine appearance, Kaitlyn’s lips were more coarse, and a slight, sandpapery sensation on the upper lip. But still, not bad.
Mitch could feel his own hands trembling. Could feel his heart palpitating. Could feel another drop of sweat rolling down his arm. Holy shit, this is really happening, he thought to himself. He reached out and placed a nervous hand on Kaitlyn’s smooth thigh, rubbing it back and forth.
Their kiss continued, their tongues exploring each other’s mouths. Their hands began searching for places to go as well. Touching each other’s silky legs, bare shoulders, smooth arms. As they started making out in earnest, Mitch had an odd thought. If one of us was really a woman, or if both were women, the goal at this point would be to take each other’s clothes off—but given the actual situation, clothing is necessary to maintain the overall illusion as long as possible.
But, as things continued to become more hot and steamy, Mitch discovered that ‘Nicole’ was taking control. Little by little, she’d been struggling to get out all evening, and now, fairly intoxicated, Mitch succumbed to his ulterior personality completely. As he allowed his hand to slide up Kaitlyn’s thigh, and under her dress, he no longer felt like Mitch wearing a dress, she felt like Nicole.
Kaitlyn pulled away from the kiss, a trace amount of saliva linking them together for a moment. “What do you want to do, Nicole?” she asked.
Nicole didn’t respond with words. Instead, she simply dropped to her knees and positioned herself between Kaitlyn’s legs. Kaitlyn spread them apart as Nicole pushed her new friend’s dress up over her waist. Almost in the same motion, Nicole gripped Kaitlyn’s panties and pulled them downward. As she did, a good-sized cock sprang from underneath. It had been concealed quite completely.
“Good God,” Nicole said reflexively. Without another word, she leaned forward, opened her mouth, and placed the other’s cock into her mouth. Kaitlyn was thick, filling Nicole’s mouth completely. She took the member into her mouth as deep as she could. It was just barely too long to deep throat. She gagged slightly and then slurped it back out. She held the base of the cock with one hand and began working the shaft up and down in her mouth.
Nicole closed her eyes and savored the sensation of sucking cock. She enjoyed it so much. From the first time I did it, she thought, on my knees in that dorm room when I was eighteen, it has always been one of my favorite sexual activities. It’s been so long. It was almost like a new sensation all over again.
In just a moment, her head had developed a natural rhythm, bobbing up and down, up and down, as she performed her first blowjob in years. She glanced down, Kaitlyn was completely smooth between her legs. Not a single hair or ounce of stubble to be seen. Nicole slurped at the knob of Kaitlyn’s cock and then licked down the entire shaft. She desired to feel that clean-shaven sack in her mouth as well. She licked at the other’s balls, sucked at them, kissed them, tickled them with her tongue. Then, back up the shaft.
She flicked at the purple head repeatedly with her tongue, making it rapidly dance across the tip of Kaitlyn’s cock. Back down, deep into her mouth. Up and down. She heard Kaitlyn make a pleased and very satisfied kind of sound. She glanced upwards, looking into the other’s eyes, hoping for approval. Kaitlyn glanced down and nodded. No words were necessary.
Nicole pulled the dick out of her mouth and sat back on her knees, smiling. She wiped away the spit from the corners of her mouth and momentarily wondered just how messed up her makeup was. She placed both hands on Kaitlyn’s thighs, in the hopes of indicating that she wanted more.
“Why don’t you stand up?” Kaitlyn encouraged.
As Nicole stood up, Kaitlyn did as well. Now they were standing toe-to-toe and Kaitlyn slid her arms around Nicole’s waist. Their lips met once more and Nicole could feel Kaitlyn’s rock hard cock pressing against her thigh.
Still holding on by the waist, Kaitlyn turned Nicole around and started hiking her dress up from behind. Nicole instantly realized what she was trying to do. She decided to make it easier for the other. She bent over at the waist and braced herself against the top of the couch. Kaitlyn tugged at the back of Nicole’s panties, pulling them down just far enough to expose her ass. Nicole felt a finger against her asshole and then it slipped inside. The finger slid in and out several times and, in just a moment, Nicole was lubricated and loosened up.
She then felt the head of Kaitlyn’s cock pressing up against her asshole. She knew how thick Kaitlyn was. She also knew that it had been years since she had been penetrated by a stiff cock. She thought to herself, this is really going to hurt. It did.
Kaitlyn pushed inside. Nicole grimaced in pain. Kaitlyn drove in further. Nicole felt like crying out, but didn’t. Then, she felt Kaitlyn’s hands on either side of her hips and she started thrusting. Her cock began working in and out, little by little. In just seconds, she was slamming Nicole’s ass. The sound of skin slapping against skin and heavy breathing were the only sounds that could be heard.
Nicole was still in extreme pain. Has it really been that long? She thought. Was Kaitlyn really that big? Not even my virgin fuck had hurt this bad. She was almost ready to tell her to stop. She couldn’t take it anymore. However, Kaitlyn was now fucking her so hard, Nicole was fairly certain she wouldn’t stop even if she told her to.
Then, something happened. Almost instantly, the pain went away. In a split-second, Nicole had crossed a threshold—and she was so fucking glad she had not told Kaitlyn to stop. It was no longer excruciating agony. Instead, it was blissful ecstasy. She leaned her chest against the couch as Kaitlyn’s thrusting became harder and faster.
Nicole gripped the edge of the couch with both hands as Kaitlyn continued to pound from behind. Kaitlyn’s hands slid higher up Nicole’s torso, and felt her tummy, scrunching her dress up at an odd angle, then back down to her hips. Strong, firm hands.
Nicole’s knees shook. Her thighs quaked. The small of her back ached. She could hear Kaitlyn’s breathing grow heavier, not because she was close to cumming, just from exhaustion. She’d been fucking Nicole for what felt like twenty minutes. She slowed her pace and then pulled out, gasping for breath.
Nicole knew she was spent. She turned around, completely out of breath herself. “Holy fuck,” she said, “I’ve never felt anything like that in my life,” she said honestly.
Kaitlyn smiled and once again wrapped her arms around Nicole’s waist. They kissed once more and again Nicole could feel the rock hard member against her thigh.
“I’m pretty close,” Kaitlyn said. “But I’m wiped out. Do you think you could finish me?”
Nicole smiled. “Of course,” she said simply as she dropped back to her knees. As she stared at the cock in front of her, she realized it had just come out of her ass. This probably isn’t sanitary, she momentarily thought to herself, but slipped it back into her mouth anyways.
She slurped at the cock once more, sliding it back and forth, in and out of her mouth. Kaitlyn had been right, she was close. Nicole could hear her breathing change. She placed a hand on the back of Nicole’s head and muttered something. It was the only cue that Nicole needed.
As Kaitlyn shoved her cock further into Nicole’s mouth, she felt that old familiar sensation of hot syrupy cum drenching the back of her mouth and tongue. Nicole swallowed twice and then lapped at the salty fluid as it continued to drip out of Kaitlyn’s cock. Another thrust. Another few drops rolling down Nicole’s tongue. She let the member fall from her mouth.
A moment later, Kaitlyn pulled her panties back up and tucked everything away. Nicole got off her knees, standing up on now very wobbly legs. Her thighs felt like jello. She straightened her dress out and tried to make herself look presentable once more.
“I need a smoke,” Kaitlyn remarked, “You want a cigarette?”
Mitch didn’t smoke. But, in an instant, he made a bold decision. He didn’t smoke, but Nicole did. “Sure,” she answered confidently.
They stepped out onto Mitch’s back porch. It was nice and dark and there was a tall fence to shield them from any neighbor’s eyes. They each took a seat in the chairs that Mitch had on the back porch and Kaitlyn offered a cigarette. She lit it, and Nicole took a drag from it. It was not Mitch’s first cigarette, but it was Nicole’s first. It felt good. It revitalized her. She could feel a surge of energy flowing back through her body.
In the dim light coming from the kitchen window, she stared at Kaitlyn’s pale thighs, her firm, bare shoulders. She still couldn’t believe this was the same person who had walked into the house two hours ago. She noticed Kaitlyn returning the stare, checking out Nicole’s own legs and body.
The cold December air felt good. They were both sweating. They were both still breathing hard. They were both—well, thoroughly satisfied.
They spent the night together that night. There was little sleeping. It was a long, alcohol-fueled, drunken romp. When they ran out of rum, they started on the beer. As it turns out, Kaitlyn could stay hard forever and could quite literally fuck all night if she wanted to. For lack of a better way to say it, she made Nicole her bitch that night. All night. And Nicole enjoyed every single minute of it.
Sometime around eleven o’clock the next morning, Kaitlyn decided it was time to go. She returned to the bathroom and emerged as the man she had been, some sixteen hours before.
Mitch—or Nicole—gave Todd one last goodbye kiss and helped him out the door.
Author’s note: I’m sure, the obvious question on most minds is: did Misty ever have a threesome with them. Well, sadly, no. While Kaitlyn was awesome in bed, there were some other issues that are far too complicated to discuss here, that prevented that from happening.
However, it should be noted that Misty and Mitch did continue to explore “Nicole’s” sexuality and… well, that threesome eventually DID happen with another man… but maybe that’s a story for another day.
Sooo… while doing my research for this story, I asked Mitch what his experience felt like… His response was so perfect, I asked him if I could just copy and paste in his response… So, these final two paragraphs are written by Mitch, trying to give you some insight on what it feels like to get dicked up the ass:
“What was it like? All I can say is that there is nothing—and I mean absolutely nothing—that feels as good as having a good-sized cock up your ass—and getting pounded all night long. I mean, fucking pounded—especially by a guy who doesn’t fucking cum at all and can literally fuck the holy hell out of you until he’s utterly exhausted—yeah, that’s what happened to me that night. I got laid—seriously laid, and it was totally unexpected, because I had no idea who this guy was or what he was capable of, and what falls into my lap? But a fucking freight train.
And yes, when I say there’s nothing that feels as good as having a dick up your ass, I mean ANYTHING. Trust me, I’ve pretty much had every kind of sex you can imagine with both women and men. And while I love my wife and love having sex with her, and love having sex with other women, and love eating pussy, and love sucking cock… nothing, and I mean nothing compares to getting fucked up the ass by a man who knows what he’s doing.
