Aidan’s favorite time of year had rolled around again. The New Orleans Jazz Fest was in full swing, and some less-than-ideal weather had done little to dampen the festivities. On this night, Aidan was in a chill kind of mood, so he had chosen to forgo the more raucous areas of town and was instead enjoying some live music from a jazz trio in a small bar on Bourbon Street. To be honest, the trio wasn’t much better than average, but he was starting on his third Amaretto Sour and was feeling entirely at peace with the world. But that didn’t stop him from noticing the beautiful young woman seated three tables over who was watching him more than she was watching the band.
Aidan did his best to ignore her. He was married with two young children, and he had certainly not come to New Orleans to cheat. Aidan’s wife, Paige, hated jazz and so had sent Aidan off alone with strict instructions to enjoy himself and to come home in one piece. But when this woman stood up to stretch her legs, Aidan granted himself permission to turn his head and get in one quick look.
She was a tall brunette in a canary-yellow dress. The dress was not revealing, but Aidan could tell by the curves and contours alone that this woman had a gorgeous pair of breasts. Not huge, but firm and high. She wore simple, yellow flats on her feet. She had an orange flower tucked in her hair, just above her right ear. On her left wrist she wore an orange scrunchie.
As he was drinking in the sight of her, his gaze moved upward and their eyes locked. Yeah, she had caught him red-handed. He turned his attention back to the stage, trying to seem as unfazed as possible. But he could feel her eyes undressing him. And though he wasn’t proud of it, he couldn’t deny that he liked it. What guy wouldn’t?
Ten minutes later, this striking woman paid her check, picked up her purse, and headed for the exit. “Well, it was fun while it lasted,” Aidan thought to himself as he watched her walk out the door. He got up to pay a visit to the men’s room, and as he was walking back to his table, he felt a hand on his shoulder. It was her.
“Hi,” she stammered nervously. “Look, I never do this, but I haven’t been able to take my eyes off you all night, and I would never be able to forgive myself if I didn’t at least introduce myself. My name is Kimilee.”
“Well, it’s very nice to meet you, Kimberly.” Aidan was trying his best to seem suave, but the reality was that he was a huge bundle of nerves right now.
“Actually, it’s Kimilee, not Kimberly,” she corrected him while still smiling warmly. “Just call me Kimmie. Everyone does.”
“Kimmie it is, then. I’m Aidan. Would you care to join me at my table, Kimmie?”
Kimilee offered Aidan her arm. Aidan looped his arm around hers and escorted her to the table. Upon arrival, he pulled out her chair and gestured for her to have a seat.
“Such a gentleman!” Kimilee said in all sincerity. “Not many like you around these days.”
“Sadly, men like me are a dying breed,” Aidan stated with equal sincerity.
The waitress walked over just as they were sitting down. Aidan ordered another Amaretto Sour. For Kimilee, it was a Sunset Passion Colada. The small talk was cautious at first–each of them afraid of saying something foolish–but they were soon laughing and joking as if they had known each other for years, with Kimilee playfully putting her hand on Aidan’s knee several times throughout the conversation.
The band announced that they were taking a break. By now, Kimilee was resting her chin on her hand, just looking deeply into Aidan’s eyes, saying nothing.
“Aidan, you obviously know by now that I find you very attractive,” she finally spoke. “And I know that you feel the same way about me.” Aidan nodded slightly, almost imperceptibly. Kimilee took a pen out of her purse and began to write on one of the cocktail napkins. When she had finished, she folded the napkin in half and slid it across the table to Aidan.
“That’s the name of the hotel I’m staying at and my room number.” Kimilee sandwiched Aidan’s left hand between her hands, placing one hand on top and sliding the other underneath. “I want you to come up to my room. I want you to make love to me.” Kimilee allowed for a lengthy pause, but Aidan didn’t speak.
“I hope I will see you tonight,” she continued. “But if I don’t, then just know that I’ll always be grateful that I got the chance to get to know you, and I wish you nothing but the best as you move through life.” Kimilee removed her hands and reached into her purse to pull out some money.
“Don’t you dare!” Aidan finally spoke. “I’ll take care of the check.”
“Still the gentleman,” Kimilee said with a smile. She picked up her purse, turned, and walked out the door.
Aidan felt exhilaration, joy, and peace all at the same time. More than that, he was feeling particularly masculine right now. This had truly been a night to remember, but it was over now. Sure, Aidan had indulged in some harmless flirting, but he hadn’t crossed any lines. And he wasn’t going to. He was being a good boy. He finished his drink, paid the check, and headed out the door. He had gotten a few feet down the sidewalk when he happened upon an open-top trash receptacle. He took the napkin from his pocket, crumpled it up, and said, “Goodbye, Kimmie” as he tossed it in the trash can and resumed walking toward his hotel.
Ten minutes later, the waitress who had been serving Aidan and Kimilee earlier that evening stepped outside for her smoke break. She was just about to take the third drag from her Virginia Slims Menthol Gold when she heard the sound of running footsteps coming towards her. She turned her head and immediately recognized who the running man was. It was that guy from table six who had been sitting with the tall woman in the yellow dress.
“Probably forgot his phone or dropped his keys or something,” she thought to herself. But just before he reached the entrance to the bar, he did something unexpected. He stopped at a trash can and plunged both arms down inside. He rooted around frantically (obviously looking for something) before finally pulling out what appeared to be a crumpled-up napkin. He opened it up, looked down at it for a few seconds, then stuffed it into his pocket and began moving at a half-run in the direction from which he had came.
“Umm, that was fucking weird!” The waitress spoke out loud. “Well, at least he was a good tipper.”
Twenty-seven minutes later, Aidan stood outside the door to Kimilee’s hotel room. “God, forgive me,” he whispered to himself. He knocked.
It took nearly two minutes, but Kimilee opened the door. She was wearing a bathrobe and had a towel wrapped around her head. She had obviously just gotten out of the shower. When she saw Aidan, her face lit up like a 1,000-watt bulb.
“Oh my God, you’re actually here! I had given up on you. Please, come in. Come in.” Kimilee waved him in then shut the door. “I was just thinking about…”
Before Kimilee could finish whatever she was about to say, Aidan placed his hands on the sides of her head, pressed his lips to hers, and pushed his tongue into her mouth as far as it would go. Most women like to be kissed slowly and gently, but Aidan instinctively knew that Kimilee liked deep, aggressive kissing. He wasn’t wrong. She returned his kiss with equal vigor. When they finally pulled their mouths apart several minutes later, Aidan was surprised to find a deeply troubled look plastered on Kimilee’s face.
“Kimmie, is something wrong? Did I do something wrong?” Aidan worried that he had been too forceful.
Kimilee turned away from Aidan and moved a few steps away from him before speaking. “No, Aidan. You’ve done nothing wrong. But there’s something you need to know about me. I’ve been putting this off for as long as I could, but now I need to tell you the truth. You deserve to know the truth.” Kimilee turned back around to face Aidan and pulled open the top part of her robe, revealing her breasts. Aidan had been right; they were gorgeous! Firm and high. She closed her eyes, took a deep breath, then fully opened her robe. Aidan moved his gaze downward, eager to get his first look at her pussy. But what he saw instead made him gasp loudly.
“I’m trans, Aidan. I consider myself to be all woman, but I still have my man parts downstairs, as you can plainly see.” Kimilee closed her robe. “Aidan, if you want to leave right now, I totally get it. No explanations or apologies needed. You can just go. There will be no hard feelings.”
For a long time, Aidan just stood there, as if frozen in a trance, before finally turning and walking quickly toward the door. When he reached the door and turned the handle, Kimilee couldn’t help but let out a sharp sob. Rejection always hurt, but this was especially painful. Kimilee hadn’t felt this way about a man in a long time. Maybe ever. Aidan opened the door, then stood motionless in the open doorway. Kimilee was just about to wish him a tearful goodbye when he did something shocking. He lifted the plastic “Do Not Disturb” sign that had been hanging on the handle on the back side of the door and moved it to the front side of the door. He then closed the door and engaged the deadbolt.
“There,” he said, as he turned back around to face Kimilee. “That should guarantee us some privacy.”
Kimilee was euphoric. She ran towards Aidan with outstretched arms, intending to give him a big hug, but Aidan lifted his hand indicating that he wanted her to stop.
“Kimmie, before this goes any further, I need to say something, and I need for you to listen carefully.” Kimilee nodded her acknowledgement. “I’m married. I have two children. And I’m not looking to upend my life. This will be a one-night stand only. After tonight, we will never see each other again. If you’re not okay with that, then I need to know now.”
Kimilee was saddened but not really surprised. She did her best to put on a brave face before saying, “Aidan, I think you’re an amazing guy, and I would love the chance to get to know you better over time. But I understand the position you’re in, and I wouldn’t want to do anything to cause you problems.” Kimilee took another deep breath. “I will respect your wishes. You have my word.”
Aidan smiled, then began walking around the room turning off lamps and overhead lights. Kimilee walked to the window and opened the curtains just enough to let in a shaft of silver moonlight. They met back at the center of the room. Kimilee sensed the more dominant side of her personality beginning to break through.
“Take off your clothes. All of them. But do it slowly.” Aidan was soon fully nude. Kimilee took off her robe and let it drop to the floor. They took their sweet time scanning each other’s bodies, head to toe. Aidan’s cock was a quarter of an inch longer than Kimilee’s, but she had a bit more girth. She walked up to him, and while never taking her eyes off his, she placed her penis on top of his, gripped them both with one hand, and started stroking. She nuzzled her face into the side of his neck for a few seconds, then raised her head and whispered softly into his ear, “Does that feel good, baby?” as she began to stroke their dicks a little faster.
“Oh my God, Yes!” was Aidan’s breathless reply.
“Good,” Kimilee whispered again. “But this is just the beginning. Tonight, I’m going to send you into outer space.”
Kimilee released her grip, moved behind Aidan, and dropped to her knees. She used both hands to spread his cheeks, then began tonguing his asshole. She moved her tongue up and down, then changed to a roughly figure-eight motion, then back to up and down again. This was Aidan’s first ever rim job, and he couldn’t believe how much he was enjoying it. Just when he thought it couldn’t get any better, Kimilee reached around with her right hand and began stroking his penis from behind, occasionally making rapid circles around the head with her thumb, all the while continuing to lick his back door. Aidan’s pleasure was so intense, his legs began to shake. He honestly believed that he might collapse to the floor at any moment. But he didn’t want to cum too soon, so he decided to change things up. He stepped away for Kimilee, walked over to a nearby chair, and gestured for her to have a seat, just as he had done earlier that evening at the bar. Kimilee knew what he had in mind. She walked over to the chair and sat down, but not before running her fingertips across his cheek and saying, “Still the gentleman.” Aidan got down on his knees, leaned forward, and for the first time in his life, he put his mouth on a penis.
He began by licking up Kimilee’s pre-cum, then moved on to sucking the head of her penis. As he became more comfortable, he took more and more of her cock into his mouth until finally he could take in damn near all of it before triggering his gag reflex. Kimilee was pleasantly surprised by how warm the inside of Aidan’s mouth felt.
“You’re a natural, baby. That feels soooo good!!!” Aidan seemed both delighted and flattered by Kimilee’s praise. But Kimilee had the same thought that Aidan had had a little while ago: She didn’t want to cum just yet. There was still more to do. She gently lifted Aidan’s head from off her cock, leaned in, and kissed him deeply. Then she got up and moved to the bed. She grabbed hold of the blanket and the top sheet and threw them both to the floor. She reached into her purse, pulled out a tube of raspberry-flavored lubricant, and tossed it to Aidan. He wasn’t expecting it, but he had good reflexes and was able to catch it out of the air. Kimilee laid down on the bed and made the “come here” motion with her index finger. Aidan walked to the edge of the bed and stopped. His dick was so hard it could have cut diamonds.
“Aidan, tell me what you want,” Kimilee demanded. “I want to hear you say it.”
“I want to fuck you. I need to fuck you. There’s nothing I’ve ever needed more.” His tone bordered on desperation.
Kimilee placed her hands behind her knees and pulled back on her legs, forming a v-shape in the air. “Fuck me, Aidan. Fuck me now. I need this more than you know.”
Aidan popped the cap on the lube and squeezed out a generous portion. He slathered it all over his cock and then moved onto the bed and up to Kimilee, remaining on his knees the whole time. As soon as he was close enough, he lined up the head of his cock to Kimilee’s asshole, and began to push it in. He closely monitored her face for any sign of discomfort, but there was none. So he pushed in further. And further. And further.
For several minutes, he moved slowly back and forth before Kimilee instructed him,” Aidan, it’s sweet that you’re trying to be gentle with me, but you can go faster. It’s okay, you won’t hurt me. Just let go.”
Kimilee pulled back further on her legs to raise her ass up more and give Aidan a better angle, and he took full advantage. He began thrusting faster and more forcefully, prompting Kimilee to enthusiastically exclaim, “Yes, that’s more like it! Fuck me, you handsome man! Fuck me like a stallion!”
Aidan was giving it all he had when he looked down and observed that Kimilee had a full erection. “It would be a shame to let that go to waste,” he thought. He reached over and picked up the lube (which, thankfully, was still within reach), squeezed a ping-pong ball sized portion of it into his palm, and then wrapped his hand around Kimilee’s cock and stroked rapidly, adding a bit of a twisting motion each time he moved his hand up her shaft. Kimilee let out a guttural moan and her eyes rolled back in her head. Her pleasure was… well, no words could do it justice. She felt like she could float right off the bed.
Aidan was getting close, and he was hoping to time it so that they would cum simultaneously. It was several minutes later when Aidan had the most intense orgasm of his life. He shot what felt like a half-gallon of cum into Kimilee’s bowels. Feeling Aidan’s cock jerk and twitch inside of her as he came was enough to trigger her own orgasm. Aidan looked on in amazement as long strands of Kimilee’s creamy semen flew from the tip of her dick and high into the air, landing mostly on her tits. Without hesitating, and without removing his dick from Kimilee’s ass, Aidan lowered himself until his forearms were flat on the mattress and his torso was inches above Kimilee’s body. He slowly began to lick and suck Kimilee’s fresh, warm cum off her tits. When he was satisfied that he had gotten all he could, he held it in his mouth but he didn’t swallow. Instead, he moved his head up until he was face-to-face with Kimilee. Kimilee and Aidan began kissing passionately with Aidan using his tongue to swirl Kimilee’s cum all around inside her mouth before she finally swallowed. They kept kissing for a long time after that until Aidan finally rolled off and lay next to her. Kimilee reached out and grasped Aidan’s hand, and they turned their heads toward each other and exchanged tender glances until they both fell asleep with fingers intertwined.
Morning arrived. Kimilee was sitting on the edge of the bed in her bathrobe, watching Aidan get dressed. “If you’re looking for your undershirt, I have it here.”
“Oh, thanks.” Aidan reached for it, but Kimilee pulled back.
“Please don’t think this is weird, but I’d like to keep this,” Kimilee said hopefully.
“Sure,” Aidan responded. “I understand.”
“Here, I have something for you.” Kimilee reached into her purse and pulled out a small, brown paper bag and handed it to Aidan. He reached in and pulled out a lapel pin in the shape of a jazz trumpet.
“I love it, Kimmie. I’ll keep it in a safe place always. And whenever I look at it, I’ll think of you.” Aidan’s voice began to tremble slightly. “Kimmie, if we had just met sooner…I mean, if the timing were different…”
Kimilee stood up and covered Aidan’s mouth with her hand. “Aidan, I hate long goodbyes. We both knew how this was going to end. It’s what we agreed to. Just go. Have a safe trip.” Kimilee gave Aidan one last deep kiss, then turned him toward the door and gave him a slap on the butt. “Go!”
Aidan walked to the door and opened it, but then just stood there. His mind was telling his feet to move, but it was his heart that was in control.
“Aidan, if you don’t leave right now, then I’m going to drop to my knees, wrap both arms around your lower leg, and beg you to stay. Then when you leave, you’ll have to drag me across the floor with each step. Just imagine the strange looks we’ll get from everyone!” Kimilee’s voice softened now. “Aidan, please don’t make this any harder than it has to be. Just go.”
It took every ounce of willpower he had, but Aidan forced himself to leave the room and walk down the corridor. The door closed gently behind him. For a good while, Kimilee just stood there staring at the closed door. Then she took off her bathrobe and tossed it aside. She lay down on the bed and masturbated while she held Aidan’s undershirt up to her nose and inhaled his scent.
Aidan and Kimilee never saw each other again.
