Maid to be a Housewife

I've always known I should've have been born female ever since I could remember. Unfortunately for me I live in a non trans friendly part of the south and never had the courage to openly be myself. I have accumulated a rather large collection of clothes, lingerie, jewelry, shoes and makeup over the years that I loved to dress up in privately. I wanted more but I was happy to have my alone time to be myself whenever I could.

I had let my hair grow long for years, mostly wearing it in a manly ponytail and had secretly started taking estrogen that I was ordering online. My skin had become softer, my body hair lighter, my face had softened and gotten fuller, my body fat began to transfer to my face, butt and breasts. My erections had became less frequent and my cum had even changed consistency. I was finally beginning to feel a satisfaction with myself. I always wore a loose shirt over my t-shirt to hide my growing breasts. They were small but they were perky and plump and I loved how they jiggled and bounced when I moved.

Then the pandemic started. I got laid off from my job, then not long after, I was let go completely. I was receiving unemployment but it wasn't enough to fully cover my bills and I began spending my savings as well. Everyone was out of work and I couldn't find a job anywhere.

Luckily for me my best friend, Tim, was an essential worker and having an extra bedroom, he offered to let me move in with him. It was a huge relief but I was also sad that my feminine activities would be even more restricted. Tim works long hours and between work and sleep, he doesn't have much time for anything else so I knew I would still get some privacy. Luckily my bedroom had its own bathroom and a large walk in closet so I had plenty of room to safely hide all of my female possessions and my supply of estrogen patches.

After I moved in, I kind of took on the wifely duties of the house, cooking, cleaning, laundry, errands etc. I found it gave me a satisfying feeling I hadn't realized I was missing. Most days I did my housework fully dressed as my female self. Pretending I was the wife was so much fun for me. Some days I would dress up as a cute maid to do my work. The more I took on this role, the more I wanted it for real and I began having sexual fantasies about Tim coming home, catching me dressed and having his way with me. I knew this was an unlikely scenario that would probably end in embarrassment but it was still a huge turn on for me and provided me with daily fantasies.

After a couple of months of our living arrangement, everything was going great. A couple of times Tim had even said I would have made a good wife if I had been born female. We laughed at those comments but inside, it excited me more than anything. I began to hatch a plan. It was going to be very risky, but i thought if it didn't seem to be going in the right direction, it would be easy to back out of it.

Tim has only had one relationship that was short lived. He spent a lot of time using online dating apps and trying to talk to women. He is a good guy but rough around the edges and thinks a lot of himself so women never really go for him. It depressed me to see him fail constantly and I felt that if I was given the chance, I could make him happy.

To help hide my femininity, I was always telling him about a woman I was talking to named Amanda. In my head it was a joke and I always heard it as "A-man-duh!" Once in a while I would go out for hours, telling him it was for a date and I even slept in my car a couple of times pretending I had spent the night with her. He bought it and it was all going into my master plan of attempting to come out to him as my female self.

When October began, it was time to put my plan into high gear. I planned my story carefully and was very nervous. But I had confidence that if my plan worked, I might get the opportunity to live my fantasy. If it failed, I should be able to back out of it with little embarrassment and keep our friendship intact.

Tim spent most nights having a few drinks, watching tv and goofing off on the internet. As we sat in the living room drinking one Friday night I set the alarm on my phone to go off with my text alert sound to seem like I was getting texts.

"Oh man! I don't know about this!" I said loudly to myself getting his attention.

"What's going on?" He asked as he took a drink.

"Dude! Amanda just texted me, she wants me to go to a costume party with her next week." I said as I took a drink. I was so nervous about starting this plan my hand was shaking.

"That doesn't sound bad, might be fun?" He said looking over at me. "What are you going to dress up as?"

I took another long drink of bourbon and coke, it's now or never I told myself as I swallowed. "Well, that's the problem. She says it's a role reversal party. Men go as women and women go as men. She wants us to go as a butler and maid, with me being the maid!"

Tim burst out laughing, "Oh man! That's crazy! I don't know if I could do that."

"Yeah I know!" I said as I made my phone alert go off again pretending it was a text. "She says if I go, she'll be very appreciative and it has a wink emoji."

"Well, that might be worth it. At least you'll be getting some action afterwards." He said looking at me with a smile.

"That's true," I said as I took another big drink, my hand trembling so much the ice in my glass clanking against the glass. "It is a costume party with people I don't know, so it wouldn't be too embarrassing."

Tim looked me up and down, "With your small frame, you should be able to pull it off, you're smaller than most females I know." He said laughing.

Hearing that gave me butterflies in my stomach. I couldn't believe this was really happening. "Oh thanks man!" I said pretending to be a little offended. "What the hell, I don't have anything else to do that night. I'm going to tell her I'm in." I said pretending to text her back but really making my alert go off again. "She says for me to come by tomorrow and get the stuff for my costume." I said with a deep sigh of relief. I had successfully started my plan and left myself plenty of room to back out if I got too scared.

Tim laughed as he took another drink. "A maid sounds about right for you! You can practice wearing it while you clean the house!" He said laughing loudly.

"Oh wow, thanks for the support!" I said sarcastically as I wadded up a piece of paper and threw it at his head.

Not much else was said about it that night as we sat drinking, a few little jokes here and there but so far, so good.

The next morning I woke up early, excited that my plan was moving forward. I cooked breakfast, set it on the table and began cleaning up and washing the dishes as Tim walked into the room.

"Well, there's my maid!" He said laughing as he sat at the table to eat.

I could feel the heat on cheeks as my face blushed. "Yeah if the shoe fits, wear it, I guess?" I replied nervously. "Thanks for reminding me, I forgot I had to pick up that stuff from her today."

After eating, Tim left for work and I went into my closet and got everything I need for my 'costume' and put it all in a bag. I finished all of my daily chores and took a bubble bath. I shaved my entire body and applied lotion to make my skin soft and silky smooth.

It was almost time for Tim to get home so I grabbed my bag and left the house. I drove around town and ran a couple of errands, giving him time to get home and settle down in his chair. As I pulled up in our driveway I swallowed the lump in my throat and nervously got my bag and walked inside. Tim was sitting on his recliner and looked up at me as I entered the door and sat the bag on the couch.

"That's a pretty big bag? That your new work outfit?" He jokingly said laughing.

"Haha!" I replied mockingly. "Yeah, she said it has everything I need. I haven't even looked at it yet." I said as I sat on the couch peeking into the bag.

I pulled out each item, holding them up and faking regret like I wasn't sure about my decision. Tim laughed at every item, the maid dress, the stockings and garter belt, the hair bow, the high heels, the jewelry, the panties, padded bra, silicone bra inserts to help push my small breasts up and the makeup.

"Damn dude!" Tim said as he pushes his recliner back. "She has you going all in doesn't she?"

I faked a sigh as I began putting everything back in the bag. "Yeah she does! She said there's a $1500 prize for the winning couple though. She told me to spend the week practicing with the makeup and clothes. She said to make sure I get lots of practice with the heels and trying to mimic the mannerisms of a woman. If I do good and we win, I'll be rewarded greatly."

"That's good, I know you could use the money too. If there's anything I can do to help just let me know. I'm finding all of this amusing anyway." He said as he got up to fix a drink.

"No, wait!" I said placing my hand on his knee. "Let your maid get that for you." I said with a smile and a wink as I took his empty glass from his hand.

"Oh, I'm going to like this!" He said laying back in his chair.

As I poured his drink, his offer to help echoed in my mind. "Hey, do you really not mind helping with this?" I said biting my bottom lip. I hadn't planned on this part of the plan but since the offer had been made, I would regret not taking advantage of it.

"No, of course not. What do you need me to do?" He called out from the living room.

I entered the room and handed him his drink. "Well, this is kind of fucked up and if you don't feel comfortable with it I completely understand." I said as I sat on the couch facing him. My mind racing, my stomach butterflies swarming! I was improvising and so nervous I was fidgeting with my hands.

"What is it?" He looked a little concerned at my sudden nervousness.

"Amanda says if we win, I can keep all of the money since she's still employed. But, there's a part of the competition I'm going to have a problem with that she says I need to spend a lot of time practicing." I explained as I took big gulps from my own drink, trying to relax.

"That's awesome of her, I know how tight money is for you. That will help you a lot! What is it you have to do?" Tim said taking a sip of his freshly poured drink and clicking on his laptop.

"Well," I took another drink, I was worried this was going to far, I didn't want to scare him off. I swallowed nervously and just blurted it out. "The men, dressed as women, have to give the women, dressed as men, a lap dance in front of everyone and be scored on it. Highest score wins."

Tim looked at me questionably, "You want to practice giving me lap dances?" He asked staring at me. I was so scared, I had gone too far, abort! My mind screamed at me!

"Well, Yeah, if you don't mind. I mean, you don't have too, I can practice on an empty chair. When you offered to help, that popped into my head as the only thing I really need help with. It's stupid though, just forget it." I said trying to play it off as a dumb idea.

"Man, I want to help you win some money and impressing your girl, but," he said stopping to think and looking at his drink. He turned it up and swallowed it all and let out a breath.

"But what?" I managed to ask. My voice almost a nervous squeak at this point.

"But I'm going to need a larger drink." He said holding his empty glass out to me. "And this stays between us! Forever! No one else knows, deal?"

"Deal!" I said taking his glass. "Thank you so much! I'll make us each a bigger drink then go get dressed!" I couldn't get myself to stop smiling as I made the drinks.

I handed him his drink and took my drink and bag of supplies to my bedroom. I locked the door and poured the bag out onto my bed. I couldn't stop smiling as I stripped off my clothes and quickly dressed in my maid outfit.

I took my mirror off of the wall and propped it up against headboard as I quickly and expertly applied my makeup. I knew Tim didn't have much experience with women and seriously doubted he would notice how fast and good I was at applying makeup. I took my hair down from my usual ponytail and quickly teased and styled it. In no time I could barely recognize myself as I looked in the mirror. I was very passable and very pleased with myself.

I took another big gulp of my drink finishing it off. I was feeling quite tipsy from the excitement and alcohol. I took my bong from my stash box and took a couple of hits of some nice bud. Tim didn't smoke but didn't mind if I did as long as I smoked in my room and used air freshener afterwards. I exhaled, watching the smoke stream from my full painted lips.

I stood nervously and adjusted my dress, pulling my breasts up and making very nice cleavage appear from under my bra and put on earrings and a cute choker. I had practiced lap dancing many times over the years. I even had a mannequin in my old apartment that I used to dance on that I had to dispose of when I moved. I was very good at it but I knew to pull this off I had to pretend to be bad at it like I didn't know what to do.

As I put my hand on my doorknob I reminded myself I could stop right now and back out of it. I could just tell him I changed my mind and everything would go back to normal. As I thought about it, my eyes caught my reflection in the mirror again. I was so cute, I smiled in the mirror, "Fuck it!" I whispered as I grabbed my empty glass and opened the door.

A large bundle of nerves attacked my stomach as my high heels clicked on the hardwood floor of the hallway. They were very loud and echoed throughout the house as I avoided the living room and went into the kitchen.

"I hear those heels!" He yelled out laughing. "Do you mind fixing me another drink?"

"Sure!" I said gathering all my courage as I came into the living room setting my drink down. As I turned and looked at him his face was in complete shock.

"You ok?" I asked with a slight giggle, taking his empty glass from his hand. He just stared me up and down, pausing on my breasts, his mouth open.

"Holy fuck!" Is that really you?" He asked as he shifted the laptop around on his lap making me wonder if he was really trying to hide a hard on!

"Don't be silly! You know it is!" I said as I walked away to fix his drink. I could literally feel his eyes on my legs and ass as I left the room.

My confidence skyrocketed! With the alcohol and weed, I was feeling very good with myself. I made his drink, extra alcohol this time, very strong. As I handed it to him, I slightly bent over, making sure he got a really good view of my breasts. His eyes were wide and stared right at my boobs. I was smiling at him but he never knew as his eyes never left me chest.

It was dark outside now and I shut the door and closed the curtains. I lit four candles in each corner of the room and turned the light and television off making it dim but still well lit with candlelight.

"I hope you don't mind," I said with my back to him. I bent over to light the last candle, arching my back and feeling my little dress rise up and expose my panty clad ass cheeks. "I just thought this would go better with less light." I said turning quickly, catching him staring at my ass.

"No," Tim said clearing his throat and taking another drink, "I like it, it's more relaxed this way."

I strutted past him toward the kitchen. His eyes all over me, making me feel confident. I grabbed a kitchen chair and put it in the middle of the living room. I patted the chair and motioned for him to have a seat.

As he stood I could clearly see a big bulge in his sweat pants. I tried not to let him see me notice it as he sat down and tried to tuck it down secretively. I got my phone and opened my playlist, I have a long list of songs I've always practiced my dancing too. I connected it to our Bluetooth system and pressed play as I sat my phone back down on the table. He turned up his drink and emptied the glass again. I took the empty glass from him and placed it on his table. He had drank a lot more than usual and I knew he had to be pretty messed up because I was too.

As the music began to play, my hips began to sway. "Don't laugh at me," I'm probably not going to be very good at this!" I said as I slowly walked closer to him. He didn't respond, just stared at me with a look full of lust I hadn't seen before.

I slowly danced around his chair, twisting my hips, arching my back, bending over, as I closed in on him I realized I wasn't scared anymore. I put my hands on his shoulders and bent over towards him. His eyes going from my eyes to my breasts. I smiled as I bent down further and tossed my hair over his face. My face was inches from his crotch. I could smell his musty scent as I looked down at the huge obvious tent in his loose sweatpants.

I straightened up and straddled his lap as I rolled my hips closer to him. I placed my arms on his shoulders as I sat on his lap. I could feel his hard cock beneath me. I placed my hands on the back of his head and looked him in the eyes as I pulled his head forward and arched my back upward, making his face go into my chest through my dress.

I suddenly realized I was grinding my ass on his hard cock and he was grinding up against me. I was so horny I could feel my own precum from my tucked penis as it spurt out of my little cock and splattered against my hole. I pulled the top of my dress down and unclasped my bra and tossed it onto the floor. My sensitive breasts tingled as the cool air teased my skin making my nipples harden.

Without a word he placed his mouth on my breasts and began licking and sucking at my nipple make me bite my lip and moan as our bodies ground together in rhythm with the music. As he lightly bit and teased my nipples I reached down and pulled at the waistband of his sweatpants until I felt his hard cock spring free between us.

My head spun as I wrapped my warm hand around his cock. I pulled away from him and dropped to my knees on the floor. I pulled his pants off and slowly began stroking his cock as he laid his head back and closed his eyes. My mouth salivated as I lowered my head and twirled my tongue around the head of his cock. I noticed how salty his flesh was as I opened my mouth and placed my lips around his head and began sucking and licking. With one hand I firmly stroked his shaft as my other hand lifted and squeezed his heavy balls.

I felt so powerful as his precum began oozing from his top and coated my warm mouth making us both slippery as he began fucking my face. I stopped and told him to lie on the floor as I removed my panties which were now soaked with my precum.

I straddled him as he lay on the floor and lowered myself on top of him. I rocked my hips along with the music, his cock pressed firmly against my slick ass as his hands came up and caressed my breasts and nipples. I reached behind me and grabbed his rock hard cock. I bit my bottom lip as I pushed back against him feeling just the tip of him at my tight opening. I pushed harder, feeling the sharp pain as his head began to penetrate me.

As we rocked against each other along with the music he suddenly thrust upward. I cried out loudly and fell forward as his huge cock split me open and embedded into me! His mouth quickly found my breasts and began sucking an my nipple as I gasped and felt my eyes water and mix with my mascara and eyeliner as he began slowly fucking me.

I relished in the feeling of his cock fucking me. My boobs and ass shaking and jiggling with each thrust. I began to relax and enjoy the sensation. I bounced my ass on his cock as he thrust upward into me. The sounds of our bodies slapping together mixed with the music as candlelight made shadows dance on the walls and ceiling.

I was feeling really good as I bounced wildly on his cock. Just then he grabbed my hips firmly and tried lifting me up but I pushed down harder against him. I didn't want to stop, I need him inside me.