Nick's New Job

"I guess we will have to find out, won't we?" he smiled, "I kinda want to see what it feels like. I've never put anything in my ass, so if you want to, be gentle, ok?" Nick said, gently stroking Kaylee's cock.

"You are just full of surprises aren't you?" Kaylee said with a big grin, "In my head, this was going to take at least a month to work up the courage to ask you if I could fuck you, but you are begging for it on our first day together."

"I'm sorry for going so fast. This is really exciting to me, and I just try to live my life to the fullest, no one knows how much time they have left, so why wait for the inevitable? I want it as much as you want to give it to me, don't you?" Nick confessed.

"Oh fuck yeah I do! When I saw you today, I couldn't help but fantasize about you being bent over, while I fucked you in that tight little ass." Kaylee purred.

"Here's your chance, baby girl." As Nick finished speaking, he rolled over onto his back, never breaking eye contact with her.

Kaylee stood up and picked his legs up to get a better look at his ass, "I might have to coax a finger in for a little bit. You look tight, and I don't want your first time to be as painful as it was for me."

Trying to think about anything to help him relax, "Tell me about your first time."

"Meh. It's not a story for this type of setting, I will tell you, just not right now. Now shut up and relax, while I toss your salad." with that, she kneeled down between his legs, and began to eat his ass. Almost immediately his dick jumped and started getting hard again. Kaylee expertly licked his asshole, making his sphincter loosen up a little bit. She looked up, and saw how hard he was already getting again, so she spit in her hand in order to jerk him off while she ate his ass out. Nick couldn't help but lose himself in the sensation coursing through his body. From the top of his head to the bottoms of his toes, his entire body was tingling with lust for her cock. Kaylee loved what she was doing to Nick. The fact that a guy could be so infatuated with her that he wants to get reamed out by her, and never questioning his own feelings. He jumped in head first, and she loved that he felt that way about her. So she would never want him to feel pain from her.

"Do it..." Nick whispered, as his eyes began to roll back in his head, "do it, please... I need you in me."

"Are you sure?" she asked.

"Please! I'll beg if I have to, but please fuck me!" Nick was completely turned into a sexy slut, begging for cock, in her hands.

She stood up and rubbed some spit on the head of her shaft, then placed it on his hole. She never looked away from him as she was so turned on by the way he looked, it was getting her harder than diamonds. Kaylee gently started to push against his ass, while she gently stroked his dick a few times to help loosen him up. He was now moaning, hungry for her to push herself into him. She pushed ever so slightly just to get the tip to push past his puckered hole. Once his ass finally gave way to her intrusion, he let out a sharp yelp.

"Are you ok, do you want me to stop?" Said Kaylee, trying to be as careful as humanly possible.

Nick was feeling the sharp pain of his sphincter being stretched past its normal stopping point, but loved the sensation surrounding it, he lifted his head and almost yelled, "Fuck me like a two-dollar whore, make me your girlfriend! Just fuck me!!!" As he said that, he wrapped his legs around her and pulled her completely into him. She had to release his cock so that she could catch herself.

Both of them let out a moan of pure pleasure in unison with each other. Nick's head rolled back onto the pillow, and Kaylee slowly started thrusting all 8 inches of her cock into his hungry asshole. She pumped slowly for a little bit until she was lubed up enough to really go to town on him.

"How does my new little cock whore like being fucked?" Kaylee said, as she started pumping faster and harder.

"Ungh... oh god... Yes!... Oh my fuck... don't stop, oh yes uh... uh... uuhh!" Nick couldn't speak, it felt like she was pushing all of the organs in his body up into his lungs... he wasn't wrong! Her cock was so far inside of him that his stomach was raising and lowering as she fucked him. The fact that he couldn't talk was making Kaylee ravenous, her balls slapped against his ass making a familiar clapping sound that was driving them both crazy. Kaylee wanted something in her mouth. She realized that she was sucking so hard on her tongue that it was now starting to hurt. She grabbed Nick's leg and put his big toe in her mouth. She wasn't normally into feet, but there wasn't anything else there to suck on, Nick was still lost in la-la-land but he did notice how good it felt. It didn't take much longer before Nick began convulsing as he was in the midst of his very first orgasm without touching his dick. The muscles in his ass tensed up around Kaylee's gorgeous member, and pushed her into her own orgasm, she thrust as hard as she could into him and released her creamy spunk deep inside of him. His dick was now dancing and spitting his hot goo all over his chest, stomach and the bed. Kaylee let his foot go and collapsed on top of him, he just pulled her into him again with his legs, not wanting this moment to end.

She laid there on top of Nick, still inside of him for a while. They kissed and stared into each other's eyes, lovingly caressing each other's skin. When she finally pulled out of him, he felt like someone just punched him in the gut. He hated the feeling of her not being inside of him.

"I wish we could just lay here and fuck all day. I never knew that I was into transsexuals until now. But I don't want it to end, ever!" Nick gushed, "Now that I've found you, I need you in my life. I think... I think I might be falling in love."

Kaylee smiled, "I can't believe I JUST found you and you've made me cum twice within a few hours. If it isn't love, don't tell me the truth because ignorance is bliss!!"

The rest of that evening they laid around had sex a few more times before completely collapsing in bed, in each other's arms, asleep.

CHAPTER 4

The next day, Nick awoke and realized where he was. Kaylee was still sleeping, her silhouette as she slept was so feminine and beautiful that Nick couldn't keep his hands off of her. He reached under the pink comforter and found her cock with his hand, he quietly positioned himself to give her a morning blow job. As he licked the tip, he could see her starting to move around a bit. He slowly started sucking and nodding his head to get her hard, which didn't take long. Before he knew it, she grabbed the back of his head and started pushing him down on her massive cock. He tried his best to put it all in his mouth, but left about 2 inches of shaft. She quietly moaned as he bobbed up and down on her. As she came, she told him not to swallow it all, because she wanted some. He gathered all that she offered him in his mouth, when she let go of his head, he crawled up and kissed her, sharing her cum with her, as they both hungrily lapped it off of each other's faces.

"Good morning, Kaylee, my new love." Nick whispered in her ear.

"You got that right! It is a VERY good morning. 'New love', huh? I could get used to that!" Kaylee replied.

"What's on the agenda for today? Or did your plan stop at calling off from work?" Nick teased.

Kaylee clicked her tongue and smacked him, "You know what, just for that, I am changing my plans. You are going to be my slave today. You will obey my every command, or you will be punished."

"Hmm, I like where this is going!" Nick smiled, "I'm game!"

"Good!" she looked at the clock, "It's 8:20 now, so you agree to be my slave for 24 full hours, right?"

"You had me at 'sex slave', honey." he confirmed.

"You assume that I mean sex slave... we'll see." she thought for a moment, "Hehe, go get a shower and get into your costume... and I don't mean Batman."

"Ok." he said, as he bounced off the bed to do her bidding.

"...Mistress!" she told him, with a smile.

"Yes, Mistress!" he corrected himself.

A short while later, he came back out into the bedroom, wearing a pink maid's outfit with a white silk apron and long white silk gloves. His face was red from embarrassment, but didn't let out a peep, in complaints.

"Oh my God! Baby, you are so fucking hot right now. You just need to add a couple of things and adjust a few others, but you have got the body to rock girl's clothes!" Kaylee swooned.

"I am a little embarrassed to ask this, since my new favorite flavor is 'Kaylee's cock', but how did you pick your name? I don't think you were always named Kaylee, were you?" Nick asked, softly.

"That's a good question, my given name was Kenneth Lee Jones, I just put the K on my middle name, 'K','Lee' became Kaylee Jones." She thought for a second, then cooed, "Why? Are you thinking about becoming my 'girlfriend'?"

"I dunno." Nick embarrassingly stated, as he looked at what he was wearing, "maybe when I'm dressed like this, you could call me... Nikki?" Nick asked.

Kaylee's eyes widened as she smiled, "I love it, baby!"

"Thank you, Mistress!" he replied with a curtsy.

Kaylee taught Nick a few things as she saw something out of place, she adjusted the shoulders so they looked symmetrical, the dress itself was twisted a bit. She reached under the dress to see if he was brave enough to put on panties, when she got a handful of hard cock, she smiled and knew what he wanted, but she was going to let him suffer for a bit.

"First things first, in the future, the dress is the last thing that you put on. The first thing would be a garter belt. You always want to make sure your garter straps are under your panties, because it can get difficult to go potty when you can't pull your panties all the way down. Especially for us, because it's almost impossible to bend your dick to fit out the back of your panties, when your garters are holding them up. Second thing would be stockings. I like to see a hint of the stocking top showing from under the skirt, because guys go nuts over that. Once you have your stockings properly put on with the line tracing the back of your leg, and the garters securely fastened to your stockings, you can put on your panties. I happen to have a pair that would match this dress perfectly! But first, let me teach you how to tuck..." Kaylee explained how a girl's clothes aren't there to cover up skin, they are to accentuate her form, and make her sexy.

This went on for a while, they talked about shoes, different style panties, when to wear certain clothes, she touched on pretty much everything. Once she had finished with clothes, she began to put makeup on Nick's face. She taught him to always go with colors that accent his natural femininity, and always coordinate makeup and clothes together.

Nick was entranced by this beautiful woman who has obviously had years of training to make sure she would be as perfect as she could be. He learned that she transitioned just after high school, about 10 years ago. Her mother was supportive, while her father couldn't accept the fact that his son looked like a girl, and kicked Kaylee out of the house. Nick hugged her, and tried to comfort her as best as he could. She appreciated the support, but scolded Nick for smearing his makeup on her. Once she was completed fixing what he had smeared, and finished with everything else, about 2 hours had passed. She was finally ready for him to meet Nikki. Kaylee walked him over to the full length mirror and let him see her creation. He was dumbfounded, there was a hot sissy maid looking at him in the mirror, and it was turning him on.

"I don't even recognize myself!" he whispered audibly.

"I told you, you wouldn't! I knew you were going to be sexy as a girl. My turn! I won't take as long as you did, I'm just gonna take a quick shower and throw something on." she stopped and faced Nick, to make sure this point was understood, "You WILL wait right here on this stool until I'm finished, do I make myself clear, sissy slave?"

"Yes, Mistress." he said, as he folded his hands in his lap as if to say, 'I won't do anything naughty.'

Kaylee took about 45 minutes to shower and get ready for the day, "It's almost noon already? Geez, where does the time go? I'm getting hungry, slave, we're going to lunch."

Nick got a shot of a worried look across his face, "You mean go 'out'? Like this?" He gestured to what he was wearing.

"Yeah, why?" She asked.

"I couldn't! People know me in this town!" he stated, while trying not to look so cute, mincing back and forth.

Kaylee was hurt, "I thought that didn't matter... Are you saying that you don't want people to know that you are a closet fag, and crossdresser?"

"Oh God, Kaylee, I didn't mean it like that! My feelings for you haven't changed, and I want people to know that you are mine, but it's just all really sudden, and hitting me all at once." Nick was shaken.

Kaylee looked at Nikki and understood exactly how he felt. It was a little nerve-wracking the first time she wore a pretty dress outside. That was after years of knowing that she wasn't meant to be an average boy. Yesterday at this time, Nick probably would never have assumed that he would be wearing a dress outside, 'Nikki' is not even a day old yet, while 'Kaylee' has been known for years. She knew she was pushing the limits of his bravery.

"I am so sorry, Nikki. I didn't mean to force you. I'm just so comfortable with you, I want to be with you every second of the day. I wasn't thinking about how this is all making you feel." She said, pulling him in for a comforting hug.

"It's not that I don't want to go out, it's just that people will have questions, and I don't have all of the answers yet... I know this sounds silly, but if I do this, will you promise to protect me from people, I might know?" Nick stammered.

"Forever."

Nick sighed and stood up, "Ok then... If you are willing to be gentle today, I am willing... to... come out... today."

A single tear rolled down Kaylee's cheek as she whispered, "Are you sure, because this will pretty much brand you as a queer, a homo, a fag, to everyone you know."

"Why did you say it like that?" Nick asked.

"I'm just saying what everyone in my life called me. I want to make sure that you are ready to take on that challenge." she said, wiping away a tear from her cheek.

"Hmm, good point. I hadn't thought of that." Nick said, as he sat back down on the stool.

"You can cook, right?" Kaylee asked, hopefully.

"The Food Network is my porn channel. I love to cook!" Nick bragged.

"Hmm, my little sissy maid can cook, huh? Well get your sweet little ass in the kitchen, bitch, I'm starving!"

"Yes, Mistress!" with that they made their way to her kitchen.

As he entered the kitchen, Nick noticed how spotless everything was. Not a fork out of place, nor a spot of water in the sink. As he found and gathered the items needed for breakfast, he wondered if Kaylee ever truly used the kitchen, as everything looked brand new.

"Sweetie, have you ever used any of this stuff? Everything looks like you just took the tags off." Nikki asked, admiring the craftsmanship of a 4 inch saucepan.

"Um... no... I actually have a little confession... I just moved into this place a couple months ago, as you know. I rarely cook, and when I do, it's something simple like eggs or microwave dinners. I eat out a LOT." Kaylee admitted as she plopped down on a chair at the table.

"How do you afford that, on what Matt pays you? Sorry, nevermind if it's too personal."

"No baby, this is the stuff we need to talk about! I want there to be complete transparency with us. Besides, you make a good point, the math doesn't add up. That's because my grandma left about a half million dollars to me when she passed away. That's how I paid for my operations, this house, and new cookware, and some of the other things I have. I've invested a lot of it, and I can almost live off the interest, I fall about $200 short per month, every month. Hence the job working for Matt." Kaylee explained.

"So are you saying I should make sure Matt pays me really well, so that I can be as gorgeous as you one day?" Nick asked, playfully.

"Meh, I like the way you are right now. I like being the cute one!" she said, stretching her arms behind her, and thrusting her tits out to remind him again.

"No arguments there! You are adorable!" He said, kissing her cheek.

"You're pretty sexy when you cook too, you know that? If I weren't so hungry, I would probably be eating your ass, or fucking you over the table with the blinds up so the whole neighborhood can see my little slut get reamed." Kaylee cooed, biting her lip.

"Geez, already? I just gave you a blow job!" Nick teased.

"I know and it was fan-fucking-tastic! You just don't realize how sexy you really are. When we go out, I will have to keep you next to me, guys will try to snatch you up, believe me!" Kaylee said, with a smile, "but don't worry, you're only coming home with me."

Nikki finished cooking breakfast, and even showed Kaylee the difference between a chop, slice, and julianne when cutting an onion. Once everything was cooked, he expertly plated each omelette, sausage, and hash browns. Served Kaylee her food, then went back to finish making his plate. Once he was done, he cleaned up the kitchen so there wouldn't be anything to do later, except dishes.

They sat and talked about food, and how Nick was going to be a chef at one point, before this stupid virus hit. They were really into their food, and talking with each other, because he never noticed that she did raise the blinds, so people outside the window, walking by on the sidewalk could see her new sissy. They were giggling and pointing at the sissy pink maid, cooking food for a beautiful woman.

They talked for hours about everything in their life that they each wanted to know. They loved each other's taste in music, and they realized that they were actually at 3 different concerts together, but just didn't know it. One concert, Crëwfest in Virginia Beach, they had seats about 20 feet from one another, but never knew each other back then. Obviously, they also shared a love for video games and comic books, since they met at Matt's store.

Then, the inevitable happened. Nick was explaining where he lived, and how he basically lost everything due to COVID. Kaylee just sat quietly and let him explain his story. When he finished, she smiled and asked him if he wanted to move in with her.

"Wow, Really? I would love that, but you don't think we are moving too fast?" Nick asked.

"Not really, we like to see each other naked, so that's a plus. You don't have to pay anything unless you want to. We work together, so carpooling will save gas... This makes sense! In a while, if we find out that we are just too different, we can part ways at that point." she admitted.

"It seems that my mind is made up for me, huh?" Nick said, with a smile.

"Well, if you don't like my big cock in your ass everyday, then we can just..."

"Hey now, let's not get crazy! You know I'm addicted to you, already." Nick said, jokingly.

Kaylee bit her bottom lip, "Soooo... it's settled then?"

"It seems that way... Wow! I never thought I would ever be so spontaneous!" Nick said, admittingly.

"I'm wondering..." Kaylee started, with a sly smile, "How far do you really want to go with this? I see no apprehension when you dress up with me, but going out might be a little much. If you just want to dress up in secret, that's fine. But if you want to go further, I have some ideas..."

"I don't know yet, but when I'm with you, I feel safe. As long as you are there, I think I could make it through... but for now, let's just enjoy each other." he said, as he seductively licked his sausage link.