The Avery Chronicles - Directions

My name is Avery. I'm 25 years old. I'm a trans woman living in New York City. I've got a great job working in tech sales. I began my transition when I moved away from my home in the south and attended college. I am active and in shape; I go to yoga and pilates routinely. I have a great group of friends who support me. My sense of style is unmatched. I have a great body. I'm 5'7", 155 lbs with tan skin, long jet black hair, soft brown yes, and B cup breast implants. I've got a cute 6.5" cock that's got a nice curve on it. I consider myself to be pansexual, I can find the beauty in anybody, as long as they're beautiful on the inside. And a lot of times, especially navigating life and dating as a trans woman, what's on the inside is equally as apparent as what's on the outside. And lastly, I can absolutely get it.

I wasn't always this confident. In fact, I spent my entire childhood vacillating between horrible spells of sheepishness and grotesque displays of overcompensating the insecurities I felt on a daily basis. I had what was essentially a non-existent support network, and I fell deeper into my isolation as I got older. I had a small group of friends that always felt temporary. I never dated. And I grew up under the overbearing and watchful eyes of my conservative parents. I couldn't see what I truly was because the world around me was busy telling me what I was supposed to be, and reminding me that I was alone because I wasn't good enough at convincing people I was what they wanted.

It wasn't until I moved away from home and got settled into my new reality as a woman. It was a slow transition, taking years of denial, anxiety, and fear about the unknown. As I grew further and further apart from my family and the burden of expectations, I found that with my newfound freedom came a developing sense of true self. By the time I graduated college I'd completed a wardrobe, gotten so good at my makeup I could do it for other women better than I could on myself, and I'd fully adopted my true she/her pronouns. Along the way came a lot of development with picking a new name, taking hormones, training my voice to sound like a woman, and some plastic surgery procedures that helped me realize my true form and present myself the way I'd always felt.

Once I was living in my true skin, I became a completely different person. Once I was Avery I was able to go out and own who I was. Which made everything in life easier. Finding a job. Finding a network of friends. Finding interesting partners to date. I spent some time working a job in my home state before finally saving up enough money (and enough credit) to move to New York City. Being in the city was everything I needed to finally get the opportunity to experience life as a woman. I'd been able to experiment a bit with my newfound sexuality and identity in college, and I was excited to grow into that more when I finally got the keys to my apartment and bought my first metro card. I was ready. I had gotten a one bedroom apartment that I furnished with a more retro look, with a leather couch in the living room, a queen size bed in my bedroom, and a small dining table for two by the kitchen.

In my past, I've been with women, men, and other trans people. Who I got with really came down to how I was feeling each day, and if I was more interested in the chase - or being chased. I could switch between submissive and dominant tendencies, taking cues from my partners and my own internal desires. I'm really game for anything, and I'm more about taking the opportunities that present themselves to me as opposed to waiting for the perfect moment to fall into my lap. As far as I see it, the most perfect chances are the ones you've built for yourself.

I want to keep a diary of sorts about my experiences and adventures. I think it is a testament to my growth, to my newfound confidence in myself, and hopefully an idea of where your own journey could take you. I've been in the city for a few months now, but I feel as if I'm withholding some valuable insights. Or maybe you're just here because you want to read about the time I hooked up with my dad's long-time business partner on his fishing boat.... Maybe I should tell that story. Another time, perhaps. But this is a story of where I'm going. Not where I've been.

*XOXO, Avery*

I've been trying to get out every Saturday and go explore a different neighborhood on foot. I'll take the subway, and then hop off and walk around on foot without looking up any places ahead of time. First, I'll pick out a coffee shop and sit down to read my book while I nurse an iced tea. Then, I'll walk around until I find a nice wine bar to sit out on the patio while I sip a glass of chilled white wine. Then, I hop back on the subway and find my way back home. It's a nice way to get out and do something new by myself, before having to go out and really run out my social battery in the evening while hanging out with friends.

Today I felt the need to go explore a neighborhood I'd been putting off for a while because it was down in Brooklyn. It took me a while to find a coffee shop that I really liked, but after a while I was settled in and making really good progress on my book. I was moving over to my wine bar when the rain started to lightly pour down. I frowned as I felt the water drip onto my hair and shoulders. 'Guess I'm going to be done early' I thought to myself, shrugging as I tried to find the nearest subway station to get home. I was wearing a gray linen long sleeve blouse, khaki short shorts, and a pair of white sneakers that showed a lot of wear, with white socks going halfway up my calves. I found the station and sprinted down the stairs.

I usually keep to myself on the platform, and this time I quickly threw my earphones in and played some music to drown out any noises. The platform was relatively empty, and I leaned against the wall in an area that kept me as far away from others as possible. This was more of a residential neighborhood than I'd realized, and I was beginning to feel disappointed that I'd made the trek from Manhattan down here. I started scrolling through my social media feeds, mindlessly looking at what everybody else was up to when I felt a soft tap on my shoulder. I don't look up, assuming it's somebody that I would rather not talk to. But after a second tap on my shoulder, I pop my right earphone out and turn my head.

"Excuse me..... I'm so sorry. But I'm lost. Could you help me?" A young woman was standing next to me. She had her arms crossed, holding an oversized purse by the straps close as she looked to her left and right timidly. She must have stood at about 5'3", with pale white skin and freckles on her face. She wore a pair of rounded glasses, which seemed to magnify her green eyes. She sported a petite frame, which was accentuated by her tight fitting green and white striped t-shirt and denim short shorts. As you moved your eyes down her body, you'd find a tiny pair of pink tennis shoes. She was all alone as she nervously smiled at me.

I immediately smile back. From my first impression this girl was incredibly cute, and I absolutely didn't want to push her away. "Umm... yeah... yeah sure. Where are you going?" I ask, picking myself up off the wall as I turn and face her head on.

"Well, I need to get back to my hotel. And I have no idea where I am. My phone didn't charge last night in the room and I can't pull up directions. I think I missed my intended stop and now I'm here." She spoke with a slight twang, and she was a bit too quick to hand over the fact that she wasn't from around here.

"Yeah it's no problem. Can you tell me where you're staying? I can try and load the directions down here." I say, feeling sorry for her as I pull up navigation on my phone.

"Well it's called the City Suites. It's in downtown!" she says. "Then again, everything looks like downtown here."

"Yeah, I guess it does." I say with a slight chuckle as I try to pull up the suggested train route back to her hotel. But my phone is getting horrible service on the platform, and it won't load. "I'm so sorry, it just won't pull up for me. How about this, I'll help you get to the general area, and then I'll try and pull up the directions the rest of the way when we get to a stop I know would be in the area?" I say. I genuinely want to help this girl, and not leave her stranded on the subway helpless. I also want to spend more time with her, so why can't I do both? She's incredibly cute, and I get to be a good samaritan for the day.

"Really?? You would do that for me??" She said, perking up as a massive sigh of relief leaves her body. "You are literally my hero!" She says, smiling at me as she lets her arms drop to her side. My eyes catch a glance at her chest, and I can't help but show some surprise at her large, probably D cup breasts. As her face opened up, she revealed a cute smile that flashed white teeth and her own pair of dimples.

'Fucking hell, those are nice' I think to myself as she stands in front of me. "Yeah, no problem at all." I say with a smile as I try and prevent myself from giving away any obvious signs of attraction. She is REALLY cute. And her little accent does something for me. "You really shouldn't be lost and alone here, it's really not safe." I'm feeling an almost desire to take care of this girl, obviously out of her element and in need of some safe keeping while trying to navigate her way back to her room.

"Oh my gosh I know, I was honestly so scared. Thank you so much!" She says, extending out her hand to shake mine. "I'm Maddie by the way!" She leaves a small hand out in front of me, and I reach out and shake it back. I want to pull her in for a hug to feel her body in my arms, but I decide against it. For now at least.

"I'm Avery, it's nice to meet you Maddie." I say with a smile. My eyes dart back down to her chest, and her low collar sits at the perfect spot between tease and imagination. "Is this your first time here?" I ask, making small talk as she comes and huddles closer to me. I turn and face the track, noting the sign showing another couple of minutes until the next train arrives.

"Yes! I honestly can't believe I'm doing this. I'm here alone, and it's like, so overwhelming!"

"You couldn't find a friend to come with you?" I say, smiling at her as I brush my hair. I look down at her hand and feel a pang of frustration. There's a big engagement ring on her finger. 'Damn... well still better to watch over another girl' I think to myself. "Or... your man? I don't wanna assume of course" I say, gesturing at her engagement ring.

"Ohh yeah, my man" she says with a nervous laugh. "Yeah people usually assume in Nebraska, so it's a bit weird to have to clarify that." She says with a shrug. "But yeah, we were supposed to come together to celebrate me getting my associates degree. But his uncle asked him to come along on some hunting trip in Montana last minute. So with everything already paid for, I decided I should just come alone, since he wasn't gonna come with me." She said, rolling her eyes as she shrugged her shoulders. "I've been here for two days now and I'm probably even more confused about how to get around than when I first got here."

"It takes a lot of time, but you get the hang of it." I say, "Do you like it here?" I ask, my ears absolutely picking up on the disappointment in her voice as she talked about her fiance ditching her for a hunting trip. Was there some disenchantment there? "And what do you study? That's so wonderful about getting your degree. You should feel very proud of yourself!" I say as I hear some commotion down the track.

"I'm studying to become a paralegal. Not that it's what my fiance wants. He'd rather I didn't work, but I want to feel like I did something, you know?" She frowned for a moment and I could pick up on her own dissatisfaction, even if she was trying her best to hide it.

The train arrived at the stop and I helped Maddie on, gesturing for her to sit down at an empty seat as the train took off. She continued on as the train took off.

"Oh yeah, it's been a bit overwhelming but I always love trying new things. I've done almost everything I wanted to, but I haven't been to a nice dinner yet here. We had reservations for a nice Italian place but I canceled when my fiance bailed." She said, frowning and looking down. "It's honestly really embarrassing.... I wouldn't want to even go alone." She shook her head as she turned back and laughed nervously. "I'm so sorry, I shouldn't even be dumping all of this on you."

I raise my hand and softly tap her shoulder as I reach around. "You don't need to apologize! It's really alright, I'm here to listen."

"You're really sweet Avery, I'm so lucky I ran into somebody kind like you." She says.

I keep my arm wrapped around her shoulder. 'Oh, I'm very lucky you ran into me.' I think to myself, my eyes wandering down to her legs before heading back to her chest. "I'm sure he misses you, and that he's crushed he isn't here right now." I suggest, trying to poke a hole in exactly where I think she's most upset.

"You know...." She says, her head dropping. "He hasn't even called me once since I got here. He's so uninterested in everything I'm doing."

As her head hung low, I extended my hand out and caressed hers. "Hey.... it's okay...." I say, seeing her looking so upset. "It's okay... it is really upsetting. This trip was supposed to celebrate you. And that's not what happened at all." I slowly rub her fingers with mine as I look at her, giving her a reassuring smile. "You know what, you should celebrate yourself!" I say, perking up in my seat and turning fully towards her.

"What do you mean? How? It's my last night in the city!" She said, looking perplexed but interested in my train of thought.

"I'll tell you what. Did you pack for a nice dinner out?" I ask her.

"Yes! I brought my dress, I was hopeful I'd find a reason to wear it out but of course nothing happened." She said.

My eyes wandered down her body again as I tried to imagine her in a little black dress. What her legs would look like in a pair of high heels. I really wanted to see that.

"I'll tell you what. Since you brought your dress, and you're celebrating such an awesome moment, why don't you come with me to dinner tonight? There's a great Italian place near my apartment. I think you'd really love it!" I say.

"Really??" She asks, perking up in excitement. "Are you serious??" She clapped her hands together excitedly. "Oh my gosh Avery I would love that! Are you sure?? I don't want to be a burden."

I wrap my arm around her shoulder, pulling her in for a quick hug before pulling back and looking her in the eyes. "Maddie, you are not a burden. It's my pleasure, you're such a sweet, beautiful woman. You deserve to celebrate yourself, and be celebrated!"

"Avery that would be soooo incredible!" She said as a smile broke across her face.

I look up at the station out the window. "Hey, this is our stop!" I help her off and walk her out of the subway station. I lean in to give her a hug. "Here, give me your number, I'll send you everything you need." I say as I hand her my phone.

She types in her phone number, handing it back with the contact name *Maddie <3*

"Oh my goodness that's so cute Maddie, you're literally perfect" I say as I smile down at her. I reach out and give her a hug, holding on a bit longer than I was expecting as I liked the way she fit in my arms. As I pull back, I brush her hair to the side and say "your hotel should be two blocks that way."

"Thank you so much Avery.... How can I thank you?"

'Oh I can think of a few ways' I think to myself as I imagine watching her change into her dress, stripping off that tight fitting shirt and letting me help with her bra. "You just come by looking like your sexy self, and that'll be enough of a thankyou for me." I say.

"Thank you so so so much.... Text me!" she says as she turns to walk back to her hotel.

"I will... make sure to charge your phone!" I say with a laugh as I watch her walk away. I immediately pull out my phone and text my friend Thomas, who I had plans with tonight.

*Hey Thomas, I'm gonna have to cancel. Recent developments, let's chat over brunch tomorrow.*

*No problem... can't wait to hear about it.* He writes back.

I walk back to the train, riding it back to my apartment. As I walk back, I stop and buy a bouquet of flowers for Maddie. I get back to my apartment and send her a note.

*Just got back, and confirmed our dinner time. 7:00 sharp, don't be late :)* I write to her. *To help you, I'm calling you a cab... is this your hotel?* I send a link to the hotel she told me she was staying at.

*OMG.... Yes it is! Avery you are too wonderful! Thank you thank you!* She writes back.

I schedule her cab on an app and begin to get ready myself. I shower off after a long morning of walking around in the sun and rain, and then I begin to put my makeup on. As I'm picking out my dress, which is a blue and white sundress with no shoulder straps, I get a text message from Maddie.

*Is this too formal? I'm not sure what the dress code is at the restaurant.* She writes. She sends a photo of herself in her dress. She's wearing a dark red cocktail dress that barely goes halfway down her thighs.

"Holy shit....." I moan to myself, feeling my body begin to shake a little as I look at her in the dress. I reach into my panties and begin to stroke the growing erection inside. I have to stop myself, can't blow it all now. I stare at her legs, noting her curves shown off by her form fitting dress. It's strapless, and I can't help but notice how much cleavage is shown off. "Ohhh... my..... God......" as I zoom in on the picture. I send back a heart emoji, and write to her *Oh my goodness, no! It's perfect! Ugh you're so fucking hot! It's not fair!* I write back. My eyes wander down and and notice her in a pair of black heels. My weakness.

*Awwww! Thank you Avery! I'm so excited for dinner!!!* She writes back.

Oh my god, it's as if she's teasing me with this photo. Hooooly shit she looks good. *I can't wait! Your cab should be there shortly :)* I write back, as I stand up and slip into my white open-toe heels. I look at myself in the mirror, hair curled and looking fabulous as I grab the bouquet and secure the table at the restaurant. I am not going to let this girl pass me by.

I take a seat, following along as she sends me updates on her trip. She's so cute, as I can tell she's never taken a cab before. I order two glasses of sparkling wine for the table and wait.

Shortly after she texts me *Here.... I think!*

I see her walk into the restaurant, and I can feel the other patrons inside all turn and watch as she steps through the doorway in that tight red dress. She looks even more incredible in person. I walk over to her and lean in for a hug, handing her the bouquet.

"Avery!! Oh my gosh!!! These are beautiful!!" She says, smiling as she takes the bouquet. "Oh my goodness, this place is so incredible! Am I dressed appropriately? I think I drew a lot of stares when I came in." She said as I gestured towards our table.

"Of course you are!! You look fucking hot...." I say as I try and sneak a peek at her ass while she walks towards the table in front of me. "They're just all in awe. Probably some jealous women here." I say as I pull her chair out.

"Avery!! Oh my god!! I've literally never been treated like this! Are we on a date" She says with a giggle as she sits down.

"We're just two girls who are out to celebrate a queen for getting her degree! And for doing something for the first time." I say with a smile as I raise my glass up in the air. "A toast to Maddie! Congrats!" I say, clinking our glasses together as I take a long sip.

The waiter comes by and takes the order, and I watch her intensely as I try and hold my gaze on her chest as long as I can. My eyes catch her hands as she gives her menu back to the waiter. "Maddie! What happened to your engagement ring?" I ask, my heart leaping as I lean in to ask her with a quieted voice.