Chapter 2: Chapter 2 – The First/Second? Date

I boot up a game and play for a few hours before realizing I have some chores to do. But first and more importantly, I pull out my phone, and send a quick message.

 

“Hey Ela, last night was amazing. Thank you so much. If you ever want to play some games again, let me know.” I then include my various gaming handles.

 

I start to go back to my chores not expecting a quick response. My phone starts to vibrate with a message. I look down at my phone, confused. There is no way she responded this quickly, it must be a coincidence. I look at my phone and I see it is actually from Ela. “I would love to, I’m running around town, but when I get home how about some non drunken Mario Kart?” It says in plain text. Right in front of me. If the proof weren’t right there I would never have believed it.

 

I start typing out a new message. “Just so you know. I am trans. I haven’t acted on it, but something you should know.” I quickly deleted it. I type it out again, and delete it again. I think she deserves to know, but I can’t tell her. It’s a bit soon, and I want to tell her in person. Why am I so nervous about telling her. I always told myself that if there was a chance of getting involved with someone I would tell them soon. I know each trans person feels comfortable at different rates, but this is my choice. But why can’t I follow through? I just have to steel myself and tell her next time I see her. Sure it might ruin it, but if she can’t accept me, there is nothing to ruin. Instead I type out “That would be amazing. Let me know when. I am going to be doing some cleaning around my place.”

 

I go about cleaning my place listening to some music and humming along with it, occasionally singing when the right song is on. It’s not much longer until I get a text from Ela “Oh, being a cute diligent maid are you?” I can practically see her grin behind her screen, but only if she knew how close to the mark she was.

 

I responded back “Nope, not today. Just some light chores, no fun stuff.” Wait… why did I say that? I haven’t told anyone about my maid stuff. Oh well, she won’t realize, because that would be embarrassing.

 

It wasn’t long before I got a response from Ela. “Oh well, I am sure we can see about that later. ;) Sadly I have to run around, talk to you later.”

 

I got up to start doing some cleaning, my eyes quickly glanced over to my maid outfit. I could do it, but I decided against it. It’s just not as fun solo as I had hoped. I throw in my headphones and turn my music to shuffle. Letting myself get lost in the music as I clean. I dance around my place while cleaning. It might make things take a bit longer, but it takes my mind off the chores. A couple of hours later I finally finished and sat down to watch some TV, having the idea to just relax for the rest of the evening. After not finding anything interesting on, I decide to boot up my switch. I decided to practice some MarioKart, I got to improve after all. I play a few races before I get a text from Ela.

 

“Hey, I just finished my errands. I see you are playing some MarioKart, how about we pick up where we left off yesterday.”

 

In lieu of a text response, I sent her an invite to play and chat. We proceed to play MarioKart for the next few hours. Switching back and forth who is winning. Eventually I know I need to log off to finish my chores.

 

“Alright Ela, sadly this is my last game for the night. I really need to finish my chores. This has been great fun. I hope we can play again at some point.” I said getting ready for the last set of 4 races.

 

“That is fine by me, but let’s make this interesting. How about we have a wager on it. If I win, I come over with a costume and watch you clean, then we can have some dinner.” Ela responds, I can practically hear her grin through the headset, as I decide on the bet.

 

Feeling confident, possibly stupid, “You are on.” We start on the first match of the night, and just prior to me getting across that finish line I am hit by a blue shell, letting her win the race. We start up the second race, and I make a few mistakes, and end up in 3rd place, with Ela in 1st. Getting nervous, and possibly excited, we start the third race. I can tell my distracted nature is causing poor performance, this time I end up in 5th, Ela again gets 1st. A win by me isn’t impossible, but I need first, and she needs last. We start the 4th race, and I try and get my head back in the game. I pulled into a quick lead and finished the first lap in 1st. I am making a turn when I am hit by a green shell and I hear Ela laugh through the sound system. This shell also bumped me off the side and I got rescued by Lakitu, but everyone passed me. I try to use the last place item advantage to get back in a higher position, with no success. I ended up last. I can hear Ela laugh as she asks for my address. Feeling my cheeks burn I text it to her.

“Alright, cutie I will be over as soon as I can. I’ll bring the outfit and some stuff for dinner. Be over soon, best prepare yourself.” She then disconnects from the chat and the game, and I do the same. I go jump in the shower to clean off the grime from my earlier light cleaning session.

 

I throw on my own pajamas to make it easier as I wait.  It isn’t shortly thereafter I hear my doorbell go off and I go answer the door. Seeing her at my door takes my breath away again. She is amazingly beautiful just like when we met at the bar. “Umm, please come inside. Welcome to my home.” I move out of the way so she can enter, closing the door behind her. I watch her walk down the hallway into my kitchen, admiring her walk, as well as her body. I snap out of it and quickly follow.

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“So, Sam, mind if I put some stuff in the fridge while you go change?” She motions to the bags she put on the center island counter.

 

“Go for it. I guess hand me my punishment outfit…” I start and finish quietly. Ela points towards one of the bags and I grab it, heading downstairs to my room. I opened the bag and let out a shocked “EEP!” It is a french maid outfit, with panties and everything. For a second I think about backing out, I rarely dress femme, and never around others. But I realize if she brought this over she is into this type of thing. I mutter to myself “in for a penny in for a pound” and get changed. The clothing fits perfectly, and somehow gives me a figure I never thought I’d achieve. It must be a trick of the clothing, I look in the mirror admiring my figure before I realize I have a guess and head back upstairs, but not before putting on the shoes she brought. They are small 2 inch heels, also perfect for my feet. I get to the door to my room and hesitantly open it and go upstairs.

 

“YOU LOOK AMAZING!” Is the first thing I hear Ela exclaim. I feel my blush coming back as I walk over to her. “Let me look at you. I can’t believe everything fits perfectly. Come on, do a spin for me!” Following her instructions I do, and I can feel the skirt flare up around me. I try to contain my giddy-ness at the euphoria. “Alright my cute little maid, go finish your cleaning and I will pretend to be the mistress of the house.” 

 

Ela then proceeds to go into the living room and turns on the TV. I can’t help but feel excited at what is going on, but I manage to control myself. With the light cleaning I did earlier, there isn’t much for me to do, but I start another load of laundry and start cleaning the kitchen and the living room after my gaming session. “Alright El… Mistress” I say through a light giggle, “cleaning is done, would you like me to start on dinner?” Then whispering and breaking character slightly. “Ummm, what did you bring for that?”

 

Ela responds confidently. “Perfect my maid, as for dinner, let's go into the kitchen and we can discuss dinner.” She stands up takes my hand and walks up the couple of steps into my kitchen. Opening the fridge she reveals what she bought for dinner. Some premade curry sauce, chicken, and some rice. “This is what you shall prepare, I decided to go easy on you today. Get the chicken cut and put in the curry then come back to me please.” Ela then heads back to the living room where I can see her sit down and watch me. I again follow her instructions and chop up the chicken and throw it in a pan with the curry sauce. Putting that on low to do a slow cook, I walk to Ela again. She leans in close and whispers “I hope this has been ok for you, it was a spur of the moment thing, and I grabbed what I had. Both the outfit and the food.”

 

Looking into her eyes, I nod replying “Oh it is great fun. I didn’t expect anything like this.” I then steal myself and try to continue. “Plus I’m…. I’m…”

 

Before I can finish Ela pulls me into a hug, “I know sweetie. Don’t worry about it, don’t worry about it.” Then like she is trying to break my brain she starts to caress my leg. “How smooth your leg is, I bet you love it don’t you.” But not allowing me time to speak she pushes me onto the couch and sits on my lap. Looking down into my eyes with a hunger I haven’t seen since yesterday. She then proceeds to attack my mouth with her own. Staking claim to it as if she were a European in the early 1700s. “How soft your skin is as well, I must learn your moisturizing routine.

Before I have a chance to wonder about soft skin, she stops her attack “Now go put on the rice cutie. And do it right, rinse it and everything.” Ela then helps me up, pushes me towards the kitchen and pats me on the ass lightly. I let out a slight giggle and went into the kitchen. Following the instructions to rinse and cook the rice, it doesn’t take me long. While the rice is cooking I grab some bowls and forks to get everything ready. When the rice is finished I place it in the bowl with the curry on the top of the rice and put everything on the table. Grabbing a couple of glasses I tell Ela dinner is served.

 

We have our dinner with a couple of glasses of wine. Chatting about various topics throughout dinner, we eventually finished. I collected the bowls, glasses, and silverware, rinsed them off and put them in the dishwasher. Unknown to me, Ela walked up behind me. The first I know is her whispering in my ear “Good girl” as she wraps her arms around me. She then turns me around and pushes me against the sink and kisses me again. All I can do is moan as we make out heavily. Eventually she breaks off from the kiss. “So my cute little maid, where is your room? I would love to see it.” I see the hunger in her eyes again as I just nod and lead her to my room.

 

As I am showing her my room I start to pass my bed as I feel her hands on my shoulder pushing me onto my bed. She then climbs on top of me and starts the aggressive make out session again. I feel her hand caress my thighs and slowly up the skirt. She reaches my dick, and all I can do is moan as she starts playing with me through the panties. She starts going faster and faster, and I can feel myself getting closer, when she stops. “I’ll finish you off, if you let me try a few things.”

 

Looking at her eyes I can see a bit of a twinkle added to the hunger, I don’t know what mischievous things she has in mind, but I know it will be fun. “Please go for it. I trust you.”

 

Ela’s smile grows wide as she moves down the bed and her head disappears beneath the skirt. I feel her remove my panties as she starts to blow me. I just relax into the pleasure slowly losing what is left of my brain when I get a surprise. I feel her hand move below me as a finger gets close to my rear opening. It then moves in as if it were perfectly lubed. Ela then proceeds to redouble her efforts on my dick, and I can feel the pleasure overwhelm any sensible part of my brain. I feel close to bursting and I try and stammer out a warning, but I don’t get very far. I can feel Ela accept everything I have into her mouth when she comes back up next to me. She grabs me by the chin and proceeds to kiss me, it wasn’t until her tongue is in my mouth when I realized she still had my cum also in her mouth. She shares it with me as we kiss and swallow it. This act elicits another moan from me, as I feel my brain tell me it is time to sleep after the eventful day.

 

“Fuck Ela, that was amazing. But it took all my energy, let's head to bed. I don’t have any pajamas for you though. I’m sorry.”

 

“Don’t worry about it my cute little maid, let me help you get undressed and let's go to sleep.” Ela coos into my ear. We then both get undressed with her helping me in my state of bliss, and we slip into the covers and pass out for the night.

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