Nick's New Job

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Shouldn't we tell Matt that we are leaving?" Nick asked, before climbing into the cab.

"You worried that your boyfriend is going to lock the doors if you come home smelling like a woman?" Kaylee asked, jokingly.

Nick made a face at her, "Ha ha, Funny! Wait, smelling like a woman? Are you saying that we are gonna...?"

"Oh my God, It is true! That's all you guys think about, is getting laid... you want me to just give you a hand job here, so you don't have to pretend to like me later?" she said, sounding hurt.

"Whoa, whoa, whoa! You got me all wrong!" Nick said, throwing up his hands in retreat.

"Uh huh, next thing you're going to want to play a game of, 'just the tip'. Then you aren't going to call me. We'll see each other at work, and we'll just become one of those people you just say, 'Hey,' to, as you walk past me... you're just like every other guy" she sounded like she was getting a little mad now.

"Stop, please, can we start over? I am sorry for making you feel like a piece of meat, it's just that you are ridiculously gorgeous and cosplay like that does something to me, I didn't mean for the conversation to go that way, I was just trying to be friendly. No, I don't want to wear a dress to work, but if I get to be friends with you, I would go through just about anything, because I really do want to get to know you." Nick confessed.

"HA! You're so easy... I was fucking with you, dude. Of course, I know I look hot. That's the point! In the store, sex sells. We just need to make you sexy too, this could be fun." Kaylee giggled.

Nick felt some relief, knowing that she isn't spooked by his forward attitude, and finally climbed up into the truck. They drove toward her house which wasn't too far away. On the way, he took time to check out her truck. You can learn a lot about someone by the status of their vehicle. The inside of this truck was just as clean as the outside was, it had a good smell, but it wasn't overly fruity, or sweet. The dashboard vinyl was well cleaned and shined with some sort of protectant oil, and wasn't all warped as Nick had seen in so many other older trucks. Kaylee was an enigma. She had a tube of lipstick, and a bullet in the ashtray. One thing he can say, is at least she is not a smoker. That's a plus, but the bullet... that could be scary.

"What's this?" Nick asked, as he took the bullet out of her ashtray.

"Oh, that's just my reminder. My dad and I used to go hunting all the time. Then some things changed, and we don't talk anymore. I keep that bullet to remind myself of the good times we had. It's not a story that I want to share right now, if you don't mind." she admitted.

"Fair enough. This is a really nice truck!" Nick said, changing the subject.

"It was a birthday present from my parents, fully restored. I added the aftermarket stuff. She's my baby." she said, patting the dashboard.

"Sounds like there's a lot of love there. If you ever need to talk, I'm a good listener." Nick offered.

"Thanks, I'm positive you'll hear all about it from Matt, though." she snorted.

"I don't want to hear it from him. I want you to tell me, when you are ready." he confirmed.

Kaylee smiled, this guy seemed to truly want to get to know her. Maybe he's the real thing, time will tell. They pulled into her driveway, Nick noticed that she was living in a pretty upscale neighborhood. They took all of the stuff out of the truck and being a chivalrous gentleman, Nick carried everything in one trip. She unlocked the front door to her house, and pushed it open.

"Welcome to Casa de Kaylee! I don't have much stuff, but I'm working on that," she admitted as her house had more milk crates than chairs, "I just moved in a few months ago, my first house! Once I make some more money, I can get a couch and a recliner..."

"It's perfect!" Nick said in an attempt to make her feel better, "I'd give it about two months and you'll have this place looking great!"

"I hope so!" she said, smiling, "come on, I'll show you my room."

He followed her into the hallway and to the last door on the right. He entered the room and realized that her bedroom was empty. She didn't have a lot of decor but what was in the room was very feminine. She had a pink comforter and pink sheets on her bed, there was a white dresser next to the window, and a matching vanity by the walk-in closet. The vanity looked like any other vanity he had seen in his life, knick knacks strewn on the desktop, half-closed drawers with feathers and strings sticking out of them. A single pink fluffy rug, sat on the hardwood floor, next to the bed. Other than that, the walls were white, and bare.

"Looks like you need a woman's touch in here," Nick joked.

"Ooh, he's got jokes!" Kaylee responded, then fired back, "Why? Are you offering?"

"You wouldn't want that. I don't know the first thing about decorating," he confessed, while wildly missing her attempt at something else.

"I'd probably end up with pictures of naked lesbians all over, huh?" she tried again.

"I wouldn't go that far, but a few bare breasts would probably grace your walls... tastefully," he responded.

"Uh huh, are you seriously trying to give me interior design tips? You better pack a lunch, because you'll be up way past your bedtime, trying to keep up with me. I know how to decorate," Kaylee said, with a challenging smile on her face.

"So, do you know what we are doing next?" Nick asked, a little nervous of what was in store for him.

"Yes I do. Strip for me, baby!" Kaylee said, getting comfortable on the bed, propping herself up with pillows so she could still see him.

Nick was kind of frozen in fear. He wanted nothing else but to get naked with this girl, but he was feeling extremely apprehensive, especially with the semi-hard boner in his jeans.

"Well? Do you need help with something?" Kaylee prodded.

"I... don't understand WHY I'm supposed to be getting naked," He replied, still not moving.

"You have to make sure the dress fits for tomorrow, Plus I want to put makeup on you to see what colors work with your skin tone." she said

"I didn't realize that I would be getting naked in front of you, right now, like this." Nick said, again.

"Is widdle Nikki bashful, does he need me to leave the room so I don't see his widdle pee-pee?" she teased.

"Well, yeah. I mean, if I can't use the bathroom or somewhere else to change, could you?" he asked.

Kaylee got wide eyed and had a look of shock on her face, "You're kidding me, right? First, this is MY house. Second, I'm not leaving a pervy guy in my bedroom alone to go through my drawers sniffing my panties or something weird like that," She softened her tone now, as she sauntered seductively toward him, "Third, I've been dying to see what you look like dressed as a sissy maid. If you play your cards right, it just might be a really good night for you." As she got closer to him, her words became more and more sensual. The last words she said were a whisper in his ear. Making his dick stand at full attention.

"You're killing me, here." was all he could find the courage to say.

"Looks like you might be a little excited to get dressed for me." she whispered, as she looked down at the bulge that had formed in his jeans, "I want to see what you're working with!"

She pulled his belt from the loops restraining it, then unbuttoned his jeans and pulled them down. His cock sprang out like a fire hose ready to douse a fire.

"Looks like Little Jimmy is happy to see me, too!" she said, as she opened her mouth wide and took the head inside. Her mouth was hot and wet, Nick was shocked by how nonchalant she was about this. He just met this girl a couple hours ago, and now she's sucking his cock! She slid his dick around her mouth for a little while, tickling and inspecting every inch of it with her tongue.

She looked with her bright beautiful blue eyes, deep into his, and swallowed his entire cock straight to his balls. No warning, no warm-up. She began sucking, and timing her breathing rhythmically with her thrusts, it didn't take long for him to tense up and spray hot liquid all over her face. As she stood up, she looked angry.

"A little warning would have been nice." she said, pointing to her face, "Clean it up!"

Nick didn't know what to do, this girl was definitely a freak. She probably wants him to do it, so he did. He grabbed her face and licked all of the sticky cum from her lips and cheeks. When he had finished, she just stared into his eyes dumbfounded.

"I meant... that I wanted... a towel." she said, stunned by what he just did.

"I-I-I'm sorry. I thought you were being dominant and wanted me to do that." Nick replied, covering his red face with his hands, trying to hide his shame.

"You... liked it, didn't you?" Kaylee asked, softly.

"I don't know, I wasn't thinking about it, I just did it." he said, pulling up his pants, thinking he should find an Uber, to take him home.

Seeing him recoil with embarrassment, she didn't want him to leave, "Wait! I didn't say that was a bad thing. I actually think it's kinda hot. Have you ever eaten your own cum before?"

Nick was feeling a roller coaster of emotions, "No! I don't know why I did it! I'm not like that, I swear!"

"Would you relax a little? I'm trying to tell you that I liked it." she smiled.

"Really? You aren't just saying that to make fun of me are you?" he asked, looking up at her.

"Fuck yeah, that was hot! I had never made a guy clean up his own mess like that before. And as greedily as you were sucking it off my face, I thought you enjoyed it too." Kaylee giggled, as she grabbed his arm and pulled him closer for a hug.

Nick was embarrassed beyond words, but something about licking up his own cum did turn him on. Especially, when the cum was on something as gorgeous as Kaylee's face. This woman was hypnotic! He had never so readily done anything like that, so absent-mindedly before.

"I did... kinda like it." Nick finally whispered.

"I think we are going to have a lot of fun together. Call Matt, tell him that you can't start tomorrow, you need a day to get your head right. I'm gonna call in sick too. I have a secret that I need to tell you, and it might be difficult to hear."

Nick wondered what the news could be, but decided it would be alright since he knew that Kaylee was a freak, and liked sex.

"What is it, you aren't sick are you?" Nick asked.

"It's nothing like that. Don't worry about it now, just talk to Matt." she said, as she walked to the bathroom.

Nick shrugged and got his phone from his pocket. He found Matt's number and hit the connect button.

"Hayday Games! This is Matt." he answered.

"Matt, hey, I hit it off with Kaylee pretty well, she wants to do some getting to know each other activities, tomorrow. So if you don't mind, I'm going to push back my start, at work, by a day." Nick stated.

"Really? I would have never guessed." Matt sounded surprised.

"Uh, yeah... Anyway, I hope there isn't a fraternization policy at work, because I think Kaylee and I are going to be seeing a lot of each other." Nick boasted.

Matt sighed into the phone, "Well, you're a grown man, I'm not going to get in the way of your happiness, as long as it doesn't hurt my bottom line. I guess I will call Rachel and see if she can cover for Kaylee, tomorrow. So you aren't going to be home tonight, are you?"

"Not if I can help it!" Nick said, with a huge smile, "I'll talk to you later, bud. I gotta see where this is going!" he finished, as he hung up the phone to await Kaylee's return.

Kaylee wasn't too long, as she exited the bathroom, Nick could see that she was now in a new outfit, if it was a cosplay costume, Nick didn't recognize it. Kaylee was wearing a white silk blouse that looked nice, but it was looser than the Sailor Moon costume. It did nothing to accentuate her figure, not to mention her perky tits. The skirt she was wearing looked like it was made from a shiny black liquid. It was so tight around her ass, he thought he could make out the line of her panties in back. If she were to bend over, he's positive that he would be able to see what color those panties were. She now had white fishnet stockings on too. On her feet she wore stiletto heels so high, that she was almost as tall as Nick now.

Kaylee sat on the stool by her vanity carefully, as not to show Nick too much skin. She had a semi-serious look in her eyes and nodded toward the bed, to have him sit down.

"I have to tell you something, but before I do, you have to promise me that you won't do anything to hurt me, in response." Kaylee said, with a shaky voice.

"Kaylee, after what you just did for me, you can tell me anything. I don't think I could get mad at you if you tried. But if you are that worried about it being detrimental to our relationship, don't say it."

"I have to. It has to do with our relationship. I didn't want to tell you like this, I never thought we would be rounding third base on our first day together. Which is why this is so hard for me to say."

"Kaylee, stop. You're starting to scare me. Do you have an STD?" Nick asked, with some concern in his voice.

"No, I'm clean... I just..." she couldn't find the right words to say.

Nick thought about worst case scenarios, the worst thing that he could think of is an STD, if she wasn't sick, what was she worried about? Then it clicked with him.

"Did I just get a blow job... from a... transsexual?" he asked, knowing the answer as soon as he asked it.

"Please don't be mad." Kaylee said, immediately.

"You have a penis?" he asked, holding his breath.

"I-I do. C-Can you forgive me for deceiving you?" Kaylee asked.

"Now I understand why Matt was so strange about you. He knows doesn't he?" Nick asked, trying to make the pieces fit.

"He kinda found out while I was stocking the shelves one day. I bent over to straighten a row of game cartridges, and it slipped out of my thong, he got a perfect view of it. The next day he called me in the office, he told me that I had to update my employment information to say that I was a male. He was not mad that I was a guy, just that I lied on my application. So do you hate me?" she asked, looking at the floor.

Nick looked at the young woman sitting in front of him and studied her features, not one thing remotely hinted at this person being a man. Nick had never given any thought about being gay, he was brought up to believe that love could hit anyone, anywhere, at any time, regardless of gender. He was questioning himself as to why he wasn't angry. He didn't feel the slightest twinge of animosity. Shocked, yes but not angry. He figured he must be ok with it then. The only thing this changes, is he may have to learn how to have gay sex.

"I think... I think I'm ok with this." Nick said, finally.

Kaylee snapped her gaze back to him, "Really?"

"I guess love comes in all shapes and forms. You turned me on with your body, before I knew you were a guy, you made me laugh as a girl, you have a lot of cool things in common with me, so... yeah, I think you're worried about a moot point." Nick said, with a smile.

"You'd... really accept me for who I am? You don't want me to change?" Kaylee asked, and she couldn't believe her luck.

"If you do, run it past me first." he confirmed, with a wink.

"I suppose that takes us to the second elephant in the room." Kaylee said, this time more relaxed.

Nick shifted on the bed, "Oh? And what might that be."

"I'm bigger than you." she admitted, proudly.

"What?!" Nick was thrown off.

"Mm-hm, by at least a couple inches." she said, stretching her arms and pushing her tits out for him to enjoy.

Nick's pride was bruised, but muscled through it until she proved it, "Bullshit, proof or GTFO." he dared her to show him.

She stood up and walked slowly to where he was sitting on the bed. She took his hand and brought it to the buckle on her belt, in an effort to have him undress her. She did this for two reasons: first, it's sexy to have your lover undress you, and second, she didn't want to scare him, she wanted him to see it at his own pace. Nick's eyes shot back and forth from her sparkling blue eyes, to her belt buckle as he tried his best to be smooth and not fumble with it too much. Once he unclasped the belt, he reached around and unzipped her skirt. Slowly, he pulled the shiny latex material out of his way revealing a sexy pair of cream colored satin panties, but no bulge. He looked at Kaylee as if she were pulling his leg at first. He then pulled down her thong, he noticed that she had tucked her penis between her legs, tightly. She spread her legs a little, to let free her last remaining shred of manhood... all 8 inches of it.

"How is that possible!" Nick was shocked, as he fell back on the bed.

"I'm sorry, do you want me to put it away?" she asked, still not convinced that he wouldn't try kicking her ass.

He looked deep into her blue eyes and reached out a hand to touch her dick. As his hand brushed against the skin, she jumped a little, this caused her cock to continue to grow. As he slowly pumped the almost fully engorged, circumcised dick, he couldn't believe how big it was getting, also that it was owned by the most beautiful girl he had ever seen. The entire time his eyes were locked with hers, he was trying to reassure her that this was okay, he accepted her for who she was. When he finally broke eye contact with her, he looked at the monster staring at his face. He stuck out his tongue and licked the tip of it, as she shuddered with anticipation.

"P-p-please," she whispered, "Please suck it."

He smiled at her one last time, then shoved her cock as far into his mouth as he could put it. He explored the veiny member intruding his mouth with his tongue as she slowly rocked back and forth, fucking his face. He took a deep breath, she smelled so sweet, he couldn't wait to make her cum so he could taste his second load of the sticky juice, ever. He began to move in rhythm with the tranny that was now fucking his face a little harder. He could hear her breathing become heavier as he sucked. A couple times she pushed a little too hard and made him gag, but he didn't mind, he was actually enjoying the fact that he was turning her on enough to get her hard. Just as he was getting settled in to suck this cock all night, she grabbed his ears and started skull fucking him hard.

This didn't take long before she growled, "Swallow it, baby. I'm gonna cum in your mouth!"

With that, he felt her dick swell once more, and started spasming in his mouth. The first shot of hot liquid he greedily swallowed, followed by another and another, before she was done, he was gagging and coughing because there was so much cum. She collapsed on the bed next to him and pulled him in for a sloppy cock and cum flavored kiss.

"How'd I do, for the first time?" He asked between breaths.

"I don't think I'm letting you out of my sight, That was the sexiest sight I have ever seen, you sucking my cock." Kaylee admitted, as she attempted to catch her breath.

Nick thought to himself, 'If this is gay sex, I am fine with it. I came once already and now my dick is already hard again, and begging for more.'

"I could definitely get used to that! Now I understand why you like guys that crossdress." Nick said, "You are looking for someone like you!"

Kaylee shook her head, "No, I was just waiting to find you it seems." and brought him in for another kiss.

They stayed like that for a while, then Kaylee got an idea, "Do you want to see how hot you look as a girl? I have been itching to put make-up on you all day!"

"Hey, who said we were done? I want to fuck!" Nick gushed, "Hold on... how does that work, do I just do you, or do we do each other?"

"That's up to you, baby. I know I can handle your little guy, but can you take mine?" she asked inquisitively.