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Learning A New Job Changes Me

Learning A New Job Changes Me

by lifeuser
19 min read
4.24 (4500 views)
adultfiction

All fiction, just based off a dream I had. Everyone is legal adults.

My mother, Enola, which means Solitude, is full native Pueblo Indian from New Mexico and my dad, Kyan, no clue what it means, is Asian from Thailand. How they met is a strange story.

He got a scholarship to Colorado University because he was a good soccer player and was found and recruited because he could kick 50 plus yard field goals.

Mom played soccer all her childhood and teen years on the reservation and got a scholarship to play soccer there because a recruiter was watching another player from an opposing team during the State playoffs.

My dad like most Asians, is 5'7"" and has a lean athletic build and my mom is 5'2" and also has a firm lean body.

I am 5'7" and have a very smooth, lean trim body.

They met by pure accident, and I mean accident when his scooter had a flat tire and he skidded into her car. Destiny prevailed and they ended up married and had me, Dakota, it means Friendly Companion. (turned out to be prophetic)

They did well in life, mom started a typing service and dad doing construction work as a supervisor so I had a good upbringing and was a little spoiled being an only child.

Time flew and I just graduated from High school with no clue what I wanted to do in life. Since i was 18, dad got me on with the construction company he worked for and after 6 months of training I liked the job. It was different and interesting learning construction techniques.

His company was expanding into Arizonia where they had a few major construction jobs going on, so he was staying out of town a good bit. One evening when he was home, he asked. "Would you be interested in going back with me and get in on the ground floor of the new construction site?"

I said, "Sure, I would love to, if mom don't mind."

Mom laughed and said, "Go ahead, it will do you good to see the outside world."

Two weeks went by before dad and I went to Sedona where the project was being built. Dad explained that we would be living in a motel that had small kitchenettes in the rooms. Kind of like a small apartment. We had our own rooms so I would have some freedom to come and go after work hours. There were a lot of places within walking distance, including downtown, a major shopping mall and a Grocery Plaza with all types of stores.

Things were going pretty well and I was making a lot of money. I learned dad drank when he was away from home and the little bar, he drank at was part of the motel. I would have a drink with him once in a while but had found a club I liked going to drinking with a diverse crowd more my age.

One night walking back to my room, as I passed his room, I noticed his curtain had a small gap in it and the TV was on. I was about to knock when through the gap, I saw him getting his cock sucked by another man. I froze.

"What the fuck? Dad is bi-sexual?" I hurried on past his room, showered and went to sleep.

I wasn't about to let dad know I saw him with another guy and made sure I paid more attention to his room in the evenings.

Three nights later, coming back for the bar, I noticed a small gap in his curtain and the TV on so I stood to the side and looked through the gap. The same guy was there and Dad was fucking him this time.

I could see his thick long cock sliding all the way out of his ass the pounding it back in. I could hear the other guy grunting in pleasure and even heard, "Fuck me hard Kyan. Damn it feels good. Fuck me with that big cock."

"Well, I sure didn't take after my dad when it came to cock size," was my first thought. "My second thought was, damn that's a turn on."

I have a small cock. It is 3.5" long and thin. I got picked on once at PE in the shower for my small cock and dropped PE and took Industrial Arts and Drafting instead.

I watched until my dad's back arched and I heard him grunting, I knew he was shooting his load up the guy's ass, and I backed away and went to my room, showered, and jacked off.

This same scene repeated itself three nights later and this time I got there just in time to see the other guy walk in and through the curtain gap I watched him undress; to my surprise he had on some panties and a bra.

I stayed long enough to watch them hugging and kissing while my father rubbed the other guy's cock and ass with the panties on. I ran to my room and jacked off.

"Why does this turn me on so much?" I wondered. "Those panties and bra looked good on him."

I turned my computer on and looked up cross dressing, I loved looking at those pictures and it had me thinking.

I tossed and turned all night and barely got any sleep. At work, all I could think of was how hot that guy looked in panties and a bra.

The following day, Dad informed me he was going home for two weeks back to the home office and I was being moved to the drafting room. Since I knew how to draft and they had an opening.

One of the guys went home for a week and the other quit. It was my opening to get that position. He showed me the drawings that were marked up and needed redrafted and wished me luck.

I did nothing all day but take my phone and google cross dressing. I was going to do it. Since I barely had any body hair and my complexion was smooth and dark skinned, Indian, and Asian blood, and my eyes were a little slanted, I thought I could pass without problems. I made a list of the things I needed to buy to pull this off.

That night, Friday, I took my measurements, researched sizes, and ordered pickup from a famous lingerie store, two sexy lingerie outfits made of silk, some leggings and a popular selling light brown colored wig that was shoulder length. I ordered me some bra padding D cups online from a local clothing shop nearby for pickup that were supposed to look like the real thing, it even had nipples that protruded some.

Saturday, I went to a thrift store and found a couple of nice sexy dresses and got more than one strange look. But, fuck it, it had to be done and no one knows me here.

I went and got my hair cut very short and bought some body hair wax removal.

I had a hard on all day picking up orders and buying stuff so as soon as I got back to my room I jacked off.

I showered, shaved all of my cock area, waxed my legs, trimmed my toenails, and painted them with some of the red polish I got and then I remembered, I forgot to buy shoes. Fuck, will have to go out again, I also forgot to get make up. Shit I was a nervous wreck. I found shoes online at a shoe store near me and had them held for pickup. I stayed away from heels since I was new at this. But I had future plans if I pulled this off.

I pulled on a pair of jogging pants and a light shirt and took off to the shoe store, grabbed my shoes then I walked next door to the beauty shop and bought a total make up kit.

I couldn't quit shaking, I was really going to do this?

For two hours I sat in silk panties with my D cup padded bra on and applied makeup. I also learned how to use the D cup padding to make it look real. Thank God for internet. "Damn these panties feel good against my skin."

I had a lot of learning to do to pull this off, how to use makeup and how to put the wig on so it looked real and not fall off. I even painted my fingernails red. I sat there just looking at myself in the mirror and kept thinking about what I was doing. I had to admit, I didn't look bad and could easily pass for a female in a dark environment.

I have no facial hair so that was a bonus and the makeup and my eyes made my face look female.

It was now 10 pm and I finally decided to try on a dress, put on a pair of shoes and go downtown to the local bar that I drank in at times. I knew the crowd there had gays drinking there also. Looking in the mirror again before I left, I was pleased at how I looked.

I stopped at the door and watched people go in and out before I got brave enough to walk in. I went to the bar and while waiting to be served a guy moved up to me and said, "Let me buy your drink."

"Thanks, I said softly,"

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"My name is James" he told me, "Nice to meet you."

"I am Dakota," I replied back softly. With the music loud I hoped my voice didn't give me away.

"Hey, don't run away but I know you are a guy. It's cool, I was hoping to meet a crossdresser one day. I think it's so sexy." James confided.

"Am I that obvious?" I asked nervously.

"Not until I got near you and offered you a drink. Let's find a table over in the corner and talk. If you don't mind."

We ordered two drinks each and found a table in the far corner where we could sit and talk. It had a round bench seat so James sat next to me.

"What made me so obvious?" I asked.

"Your makeup," he told me. "You need to learn how to put it on better, and trim your eyebrows, then the way you looked standing, too straight and man like. I will be happy to give you lessons."

"I'll think about it," I replied back.

After a few more drinks I excused myself to leave and James asked, "You driving?"

"No, I walked here from the motel nearby. It isn't too far."

"It's almost a good mile away, you walked here?" he exclaimed.

"I'm used to walking and it gave me time to get courage or chicken out."

"Let me drive you back, I really am interested in you. Honestly, I always hoped to meet someone like you."

"Okay, but I can't promise anything will happen, this is a first time for me to even try anything like this. It was an infatuation and I had to try it." I told him.

"No problem, you are safe with me; By the way, you do look really good. With time and experience nobody will be able to know you are a male, I promise."

We got to the motel and James asked if he could come in and visit some more to get to know each other better. Reluctantly, I agreed. Curiosity was getting the better of me.

We talked a while longer and come to find out we had a lot in common. We never talked sex but then it came out.

"Dakota, can we hug?" James suddenly asked.

I slowly stood up and we hugged for awhile and then he reached under my dress and started rubbing my ass. I froze a little but let him continue.

"Damn silk panties feel great to rub your ass with, your ass is so soft. Do they feel good against your skin?"

"Yes, I love the way they feel, I also love the way the leggings feel, they make me feel sexy." I said breathless.

Jame then moved to my cock and rubbed up and down and the heat in me rose to a point I thought I was going to pass out. I moaned softly.

James took the que and started to kiss my neck and moved toward my lips. "Fuck, I want this," I thought. "Just do it," my brain said.

I let his lips touch mine and then slowly our tongues explored each other's and the inside of our mouths. I was in total heat.

James laid me back on the bed, took off his shirt, then pants and I saw his nice 6" circumcised cock standing straight out.

"You don't have to do anything," he whispered. I want to hold you naked. He then proceeded to undress me and hugged his naked body against mine. We kissed some more and he said softly, "you really do have a very soft body, it feels good against me."

I couldn't stand it, I wanted to feel his cock, it rubbing against me just kept me on fire. I reached down and slowly touched his shaved cock and then cupped his shaved balls; it felt so good.

"That feels so good Dakota" he said softly.

We kissed more and it just happened, I moved down his body until my lips were at this cock.

"What am I doing?" I asked myself. "You are doing what you want," my mind told me back. "Try it, you will like it, I promise," my mind told me. "This is what you have been missing in life."

I let my tongue run over the head of his cock and tasted his body and precum, it wasn't bad. In fact, it was an intoxicant and I wanted more.

I slowly tasted the full length of his cock, moved down to his balls and back up. James announced he was going to cum and it just made me want it more. I sucked the length of his cock up and down and when I felt it get hard; I took it all and sucked the cum out of him.

His load gaged me some but I was determined to swallow it all and make him beg me to stop. The after taste wasn't so bad.

"Uncle," James called out laughing. "Damn Dakota, you sure are full of surprises."

I smiled and worked my way back up and kissed him. "Yes, I am, even to myself. You can stay the night if you want."

"I would be happy to," They cuddled together and fell asleep.

Moring came and James had morning wood and I wanted to suck his cock again. I moved down the bed and sucked his cock deep into my mouth and worked the head of it with my tongue. I felt it twitch and a load of cum shot down my throat.

"I think that is the fastest I have ever come," James said smiling. "Good morning"

"Good morning to you" I said as I slid back up and kissed him. "Want some breakfast?" I asked.

"I like coffee and toast," James replied back.

"Give it a few minutes," I said and got up to fix it.

We had our breakfast, went for a walk, I did not dress up, just had my joggers and a shirt on.

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"Anyone ever told you your ass is nice looking?" James asked.

"No, you would be the first." I laughed.

"Well, you do, it's a riding ass, made to climb in behind it and ride." He spoke.

"Hum, never tried it but you might get lucky and take it for the first time." I looked in his eyes saying it.

"I would be honored," he smiled back.

We finished our walk and showered together. Him bathing me and kissing me and my body had me turned on again. He had me lean against the shower wall, spread my legs, and started kissing and French kissing my ass inside and all around it. My knees were buckling to the point I had to say stop, turn off the water, dry us off and lead him to the bed.

He resumed his kissing and sucked on my small cock for a little then turned me over, spread lubricant all over his fingers and on and in my ass then worked his fingers slowly one at a time until I was pumping his fingers.

"Are you ready?" He moved up to my ear and whispered.

"Yes, please it's yours," I said back in a heated voice.

I felt his cock rim me and slowly pumping in and out until he worked his way fully inside of me. I was expecting some pain but he did it so perfectly, it felt great.

James slowly started small strokes and worked his way to long strokes.

"Fuck me James, fuck me with that hard cock. Cum in me please." I was panting.

James kept fucking my ass harder and harder then, I heard him grunt, "Yes James, fill my ass deep with your load, Fuck me good."

It wasn't long and felt his cock get hard and I started tightening my ass to match his strokes, suddenly I could feel the warmness of his cum shooting inside of me.

"Oh Fuck," he called out and kept pumping my ass until his cock started getting soft. "Damn Dakota, you sure were a great fuck,"

"You sure fucked me good," I said back smiling. "I might walk bowlegged for a few days.

We spent the rest of the afternoon with him teaching me makeup and trimmed my eyebrows a little. His mother worked in a beauty salon and had side clients at home so he learned a lot listening and watching her make up clients. He told me to watch videos of women walking and learn their mannerisms. After we had a very late lunch, he said, "Dakota. I live about 100 miles from here. I visit an aunt once every few months. I hope we get to meet again."

"Dang, that's a bummer I thought," but actually said, "James thank you for everything. I sure hope we meet again also. You opened a whole new world to me. Also thank you for the makeup lessons and advice on learning women's mannerisms. I will make to sure to use them to the best of my ability."

With that we parted ways and I laid in bed and cried.

The work week went slow and I practiced putting on makeup every evening and learning women's mannerisms and walking. I had to admit, I was looking good and actually felt like I was more feminine and was ready to go out again.

Saturday night I went back to the downtown bar, had a few guys buy me a drink, even after I told them I had a boyfriend. One guy even told me I had a fine ass, made for riding. That made my night. I was all smiles walking back to the motel and when I got to my room, I heard a voice, "hey Misses, that's my son's room."

I about shit in my pants, "What the hell is dad doing back?" I thought he was gone for two weeks." I was thinking in panic.

"Oh, mistake," I said softly heading toward the motel office.

My luck, dad caught up with me and said, "hey, you want a drink?"

I tried to turn away but he saw me and his mouth fell open, "Dakota? What the heck?"

I was caught, pure and simple so I just said, "Yes dad it's me, sorry if I disappoint you but I found out, I like this. It just happened. I hope you understand. I though tyou were gone for another week."

"Dakota, you are the love of my life other than your mom, it's new and different. I thought os also but there is a meeting with the client and I had to come back. How about that drink or two or three." He said as he laughed a little nervously.

"Sure, why not, I need a few right now," I responded back quietly with my head down.

We walked into the motel bar and found a place away from the bar and ordered double whiskies each and another round after that.

"What made you try crossdressing?" dad asked.

I thought for just a second and just told him the truth. "Ever since I got made fun of in PE, I felt alone. Except for the times I was with you and mom. I was walking back to my room one night and saw through a crack in your curtains a man standing next to you wearing panties and a bra. The way you rubbed his panties and all, turned me on. I became obsessed with trying it. It looked good seeing him dressed as a lady. I liked the attention he got from you. Dad, I didn't know you were bi."

"Ah yeah, well, son, I love your mom with all my heart but we quit having sex shortly after you were born because my size hurt her too much. She did her best and let me rub my cock against pussy her until I shot my load. Bless her heart. Then, this job came up. I was having a few drinks in here and went to take a piss and a guy came to the stall next to me. When he saw the size of my cock he said, "I wish I could find a cock like that to worship."

I was drunk and said, "well come to my room and worship it." He did and when he undressed, he was wearing panties. Well, he sucked me, I fucked him and now we see each other a few times a week. He is married and she doesn't do anything but lay still while he fucks her. He tried male sex and likes it, so we are the perfect match to help each other out."

I sat and listened to his story and it aroused me. I couldn't believe my dad aroused me.

I finally spoke, "I met a guy the first night I went out cross-dressed and we got along so well, I took him home and bedded with him and did everything. It just happened. I didn't plan it or even want it when I went out. It felt right at the time. He taught me how to use makeup and even had me watch videos to learn women's mannerisms and how they walk."

"Does it feel right?" dad asked.

"Yeah, I like dressing up like a lady and acting like one, it feels good to have the attention." I confessed to him.

"I understand," dad said. "Going to order another round, excuse me a minute."

Dad got up, went to the bar, came back with two more doubles and we saluted and shot the first one down. After sipping down the next one dad said, "Going to pee, be right back."

I laughed as he staggered toward the bathroom and decided I need to pee also.

I walked to the stall next to him, pissed and looked over the stall at his cock and said, "Damn dad, no wonder why mom was in pain."

"Hey now, you can't be in the men's bathroom and staring at my cock."

"Whoops, need to remember that part when I am dressed up. Fuck dad, the size of it makes you stare."

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