Emily Ch. 02

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Emily finds herself.
3.8k words
4.57
13.6k
12

Part 2 of the 2 part series

Updated 06/08/2023
Created 12/26/2016
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ShyTammy
ShyTammy
458 Followers

Emily: God that was intense

Tammy: I know right? We aren't even to the really good stuff yet.

Emily: Wholly shit I didn't realize how emotionally draining this could be.

Tammy: Do you not like doing this?

Emily: No, I love it, it is just harder work than I expected and I am not even writing it. You make it look so easy.

(Hugs)

Tammy: Are you ready to go on?

Emily: Yeah, lets...

(Once again in Emily's voice)

I slept like a baby that night, even though the bed was kind of lumpy and uncomfortable. I woke up early the next morning to a bright sunny day. I almost immediately realized that I had nothing specific to do. My life had been so structured around chores, school and church that it seemed like I was always moving from one task to the next. For the first time I had choices and options.

This feeling was both exciting and scary to me. At first it put me into a kind of paralysis, I couldn't move because there was no obvious direction to move in. Fortunately my body decided to give me some direction when my stomach growled.

I showered, threw on some clothes and left my dark little cave of a room in to a big and brightly lit world. It was hot outside already and it was only 9:30 in the morning. Not sure where to go I just picked a direction on Central and started walking. A few minutes later I was in the University area and came across this restaurant that was bustling with young people.

The place I would later find out is an Albuquerque icon, the Frontier, sold cheap breakfast burritos. I got one and a coffee and sat down among the teeming crowd of college age kids. This was pretty impressive as it was summer and the place was still super busy. I ate in anonymity, too afraid to talk to anyone and yet I was still infected with the optimism of the place.

After my breakfast, with nothing much to do I wandered back to my hotel. As I wandered I thought a lot about what I was going to do. I was nervous as hell, I only had a couple thousand dollars to last me the rest of my life. I also thought a lot about who I wanted to become. My mind wandered back to my early experimentations trying on my sister's clothes.

I got back to the hotel and with nothing better to do I lay back on the bed and thought about the night before. I had had sex for the first time. Thinking about being with Miguel and I pulled my pants down and just openly masturbated for the first time in my life. Oh I had masturbated before, lots of times, but it was always a furtive hiding thing that I had to sneak around with. Lying there in MY place I just rubbed myself and moaned all I wanted to until I came. It was glorious.

Next I figured I should get some supplies to stock my little kitchenette so I wouldn't spend all my money eating out. I emptied my backpack and grabbed my skateboard. Soon I was flying free down Central Ave. towards a Walmart I had seen the night before.

As I shopped for the most frugal groceries I could find (Raman noodles made up the bulk of my basket), my eye was continually drawn to the clothes section, specifically the girl's clothing section. All those bright colors wouldn't leave me alone. I worked up the courage to go over.

Looking around at all the clothes was like being in heaven. I was hyper nervous that someone would figure out what I was up to and boot me out for being a pervert. No one did though. No one even gave me a second look.

I would have loved to have shopped forever and picked out everything perfectly, but instead what I did was grab a couple of cute dresses that looked like they would fit. I also quickly grabbed a package of six pairs of panties, some tights in different colors and two teen bras. I threw in a cheap kids make up kit. Shoes I had to go over to the Women's section for. I eyeballed the size of a couple of pairs of inexpensive ones and threw them in the basket too.

If I did my math right it should all be under the $100 I had brought with me. I stood in line with my heart pounding, but everyone was too busy with their own lives to bother looking at what I was buying. That included eventually the cashier who rung me out with the dull expression of someone who hates their job. I had overestimated and the total bill only came to $63.

Outside of Walmart I stuffed my backpack with all my loot and I was off back to my little sanctuary as fast as my skateboard could take me.

Back at the hotel my bed had been made for me (the bonus of living in a hotel). I put my groceries away and made myself a lunch of Ramen noodles and a banana. Then I carefully laid everything out. Mixing and matching I had enough stuff for about 3 outfits.

After lunch I took a nice long shower, two in one day was a total luxury for me. I regretted not getting some girly soaps or sweet smelling stuff. The hotel samples would have to do though. When I got out of the shower I ripped open the package of panties.

They were nothing special, just simple cotton panties with floral designs on them. The kind my sister wore every day. Pulling them up my legs I couldn't help but shiver with excitement, my cock hard as a rock. I spent a while adjusting them so the set "just so" on my hips and cupped my ass. I thought if I just looked in the mirror between my upper thighs and lower belly I looked just like a girl except for the raging hard cock that was neatly tucked inside.

The bras were more of a problem. I had gotten the "training bra" kind because I figured I didn't really have a chest to speak of. The first one turned out to be way too small and I ripped it trying to put it on. The other one was adjustable in the shoulders so I was able to get it on with a struggle.

Then I sat down at the nicotine stained and chipped Formica desk in my bra and panties. I opened my laptop and plugged it into the Ethernet. Immediately my mailbox dinged with over thirty pieces of mail. I avoided that for the time being and opened a web browser. Searching I found hundreds of videos on how to apply makeup.

I took out my little makeup kit and followed along as best I could. I could see I would need to get more things as this kit was for kids and really basic. The important thing I think is that I learned the names of the things I needed and what they looked like. I did after a couple of hours of messing around end up with a look I really liked.

I did lavender around my eyes and some blush on me cheeks. I added a pink lip gloss and I looked kind of like Molly Ringwald with my messy, short red hair.

That done I tried on some more of my clothes. Again I misjudged the size. I am really skinny but I probably too tall to be shopping in the "Girl's" section. I vowed next time I would try "Women's". Still the first dress I tried on was a struggle to get into but it eventually worked. It was really tight and short. It was a thin cotton pink solid color dress. I could pull it down far enough to cover my ass but after a bit of walking around it would hike itself up and I would have to pull it down again.

I put on a pair of white tights, which thankfully fit me well. Then I tried on a pair of shoes, just a simple pair of white pumps with a short heel. Before long I was prancing around my little hotel room and talking to myself in a girly voice.

"Who's that sexy girl over there?" I'd say to myself in the mirror.

"Teehee who me?"

"Yes you, you're hot and you know it."

It was ridiculous but I felt giddy and free to be who and whatever the hell I wanted. I was so high on it I thought to myself "I'm going to walk right out that door and down the street."

I went to open the door and stopped. I peeked out the window and watched the people walking up and down the street. I got scared and sat back down. I really wanted this though. It would show the world I could be who I wanted. I tried again, I chickened out again. I practiced my walk and my voice and my look in the mirror. I tried again and failed again.

It was late and dark by the time I worked up the courage to leave. I timidly opened the door. No one was coming or watching. I scooted out onto the sidewalk then walked as fast as I could in my heels away from my door. Then I was on the sidewalk and I tried to walk down the street as if nothing was happening.

And nothing was. I wasn't used to the relative anonymity of a city yet. Albuquerque is small but big by the standards of where I came from. There everyone would have recognized me right away. Here, no one cared and even if they noticed they had seen stranger things before.

So I walked the half a mile to the convenience store. I bought a soda. The clerk, a cute and kind of punky girl with a bunch of piercings smiled at me.

"Have a nice day." She said after I paid her.

Other than that no one noticed me at all. It was a bit of a letdown, I meant this was such a big moment for me and no one cared, no one even cared enough to ridicule me. That was the first time I realized I was lonely.

This was really the first bit of reality to sink into my grand adventure. I didn't let it get me down though, lonely as I was; I took advantage of the anonymity to perfect my female form as much as possible. Over the next two weeks I made several more trips to Walmart to build up my makeup, cheap jewelry and wardrobe collection. I also watched a lot of videos on how to be feminine and practiced and practiced with a dedication I had never really had to anything before.

I was getting pretty good at pulling off a female persona. I was becoming Emily, the cute strawberry blonde with freckles and a flirty attitude. My confidence growing I even found myself going out of my little hidey hole during the day. As far as I could tell I was passing for a young girl. It was intoxicating.

I still hadn't given up on Brian completely. I got a very androgynous haircut that really could go either way. Emily was great, she was feeling more and more like my true self, but Brian was legit, had ID and a social security number and all that. Watching my ever dwindling pile of cash I became both more frugal and started looking for jobs, something I felt only Brian could do. This was Brian's main function, filling out applications for entry level jobs, something I knew I would have to get before long.

Eventually my confidence was high enough that I got around to reading my email. There was one note from my Mom and another from my perverted Youth Counselor. I read the note from my Mom. It was full of how much of a mistake I was and that my Father would likely kill me as see me again, and other very Christian sentiments. I deleted the one from the Youth counselor without reading it. Then I noticed one from my little brother. It was short and heartbreaking.

"Mom and Dad are pissed, please don't come home. Sis and I miss you though so please let us know you are OK. We won't tell anyone."

I couldn't help but cry. This adventure was a one way street and I knew it. There would be no going back to my parents under any circumstances. I tried not to think about failure and what that would lead to, but there was a voice in the back of my head that was like a bank robber or something saying "I won't go back to that life alive." I remembered that time I tried to end it all, if I did again there would be no little brother there to save me this time. I really did try not to think about it too much. Instead I wrote back.

"Thank you so much you guys. I am doing good, safe. I love you!"

That was it. I closed the family chapter of my life. I cried myself to sleep. The next day I had put it behind me and was back to working on Project Emily.

Then one Saturday night I was just walking down Central as Emily, enjoying the warm night air and the feeling of life all around me. I had on a tight dress, thigh highs and a strappy pair of wedges. I looked amazing and was getting some looks from people passing by on the street. I loved it.

Then a really big car pulled up next to me and followed me slowly. The window rolled down. I thought that the fat man driving might need directions or something; I was delighted to interact with anyone at this point.

"Hey cutie." He said as he pulled to the curb. I just blushed at this.

"You lookin for a date Sweet Cheeks?"

"I uhh umm..." I stammered, not quite sure what to say. I mean I wasn't attracted to him at all, but it was flattering.

Those of you who are more worldly will see what was going on here, I was pretty clueless when I went up to his open window. He seemed harmless enough, he was overweight and white, but clean and well dressed with a nice car.

"How much you chargin Honey." He clarified.

"Oh I'm not, I mean, I uh." It finally dawned on me what he was getting at. He wanted to pay me for sex.

"I don't know, I'm new to this." I confessed. I wasn't even really sure I was going to do it. It was so out of the blue.

Here is the thing; I wasn't completely naïve as many of my neighbors in my fleabag hotel were prostitutes and junkies. I just never pictured myself in that scenario, yet here I was. I knew I didn't want to be like most of them, but I also knew I needed some money.

"Why don't you get in Sweetheart and we'll chat about it."

"OK" I said stupidly.

So there I was in this strange man's car. His hand went immediately to my stocking covered leg sending a thrill of fear and something else through my body.

"You've never done this before have you Sweetie." He said with a Texas twang and an eagerness that freaked me out a little.

"No sir." I replied meekly.

"Well shit." He said with a squeeze of my thigh, "Seems to be my lucky night. How much you want?"

"I don't know, like $300?" I said nervously, not really even realizing what I was selling.

He laughed, "You got solid gold between those sexy legs?"

"What's a better price."

"Ha I should charge you for lessons honey, but I'm feelin ya so advice is free tonight."

"It really all depends on what you're willing to do." He continued "I'll pay you $40 for some quick head, but you're such a cute girly boy if I can convince you to give me an hour of fun I'll give you $120, nuthin too kinky mind, just show Daddy a good time."

"I think I can do that." I said.

"Great!" he replied with enthusiasm, "You got a place?"

"Yeah" I said, my confidence growing a bit, I gave him directions to my hotel.

He followed me into my room, his hand on my ass. This sent those same ambiguous thrills throughout my body. When we got in he took me in his huge embrace and we kissed a little. Then he pushed me back.

"OK advice point number two." He said getting out his wallet, "Always make em pay first, don't want no tricky dicks rippin off my Baby Girl."

Handing me the money he asked me to put on some music. He took off his pants and button up shirt and sat on my bed in an undershirt and clearly tented boxers.

"What should I do next?"

"Call me Daddy." He said.

"What should I do next Daddy?" I replied blushing furiously.

"Strip for me."

I swayed to the music, not quite dancing. I pulled my dress over my head. Then I took my bra off, exposing my flat chest and rosy pink nipples. He pulled me in to suck on them as I stood in front of him in just a lacey pair of panties, stockings and wedges.

"Sweet as November rain." He said after he was done sucking my nipples. His hand massaged my hardening cock through the front of my panties. Then he took it out and gave the head a little kiss.

"Mmm mmm." He said like he was eating home cooking.

"Why don't you go down for a bit Sweeting, get Daddy's motor running." He said as he pulled out his cock. It seemed like his motor was already running, his cock was thin, pink and clearly already as hard as he was going to get.

I knelt on the floor and kissed the head of it. Then I started to suck him. He leaned back on the bed and just moaned as his cock slid in and out of my wet mouth. As I was sucking him I was thinking "this isn't so bad at all."

His moans were getting louder and I picked up the pace.

"Whoa, whoa, whoa, Honey that ain't what we agreed to. Get that sweet ass up here."

"Turn around." I did.

He pulled my panties down to my thighs, spread my ass cheeks and started licking my tight little hole. I was really surprised by him doing this and how good it felt. Soon I was moaning and he was rubbing my cock and his tongue was probing my ass.

"You got a rubber sweetie?" I nodded remembering the bag from the pride parade. I went and got one and some lube too.

"Always make em wear a rubber sweetie," he said "don't know what these fuckers will give ya."

"Now put it on me, there ya go." He moaned while I worked the condom down his long thin dick.

"Ok, now lay back on that bed right there." He encouraged, "yeah there you go, get nice and comfy for Daddy."

Then he spread my legs, kissed my hard little cock again. Then he kissed his way up my body until he was kissing my lips. Grabbing his cock he started guiding it toward my ass.

There were a few awkward attempts to push in.

"Fucking hell you are tight girl." He said with a bit of frustration.

"I'm sorry." I said lamely.

"Oh don't you apologize for a thing Sweetie, this is gonna be amazing."

Then he was pushing at me again, this time he was more successful. His cock was neither big nor thick, so it didn't really hurt when he finally penetrated me. Next thing I knew the whole world was moving back and forth as he pushed his cock in and out of my ass and he kissed my neck frantically. My world became absorbed in his humping moving mass as he fucked me.

The bed started hitting the wall rhythmically. Just as it was starting to feel really good he pulled out and scrambled to a kneeling position, pulling off the condom and pumping his cock red-faced.

"I'm gonna cum all over you!" he shouted and then he did as shots of cum were landing on my hard cock and belly. He just kept shooting all over me.

"Shit, sorry Missy." He said, "you're so damn tight I shot my wad too soon."

"No problem" I said, keeping in mind he was paying me "It felt really good Daddy.'

"I wanna watch you cum too sweetie." He said grabbing my little cock and rubbing it. Then his other hand reached between my legs and started fingering my ass again. The stimulation was too much as he really knew what he was doing. Soon my back was arched and I felt like I would explode.

"Oh my god Daddy, I'm gonna cum!" I warned him, he just stroked me that much harder.

Then I was shooting cum all over myself and his hand.

"Ooohhweee! That was a gusher!" he exclaimed.

I looked at the clock; we'd been at it for about 40 minutes of his hour. I got up and went to the bathroom. I cleaned myself up and then brought a warm, wet wash cloth out to clean him up too.

Not sure what to do with the rest of the hour I just laid next to him and snuggled up to his huge bulk. He was actually kind of cuddly and it had been so long since I had any human contact. He made a lot of contented noises as we just lay there.

Then right on time he sat up and started getting dressed.

"Damn Sweetheart, I wish I could spend all night working that fine little body of yours, but I gotta run, you got a number I can call if I want some more?"

I gave him my cell number and he tipped me another thirty dollars as he left.

I wasn't sure if I would do this again, but it felt good to know I could make money if needed. It felt good to know that someone desired me so much that they would pay for my company. It was a huge ego boost. I was also fairly sure if Daddy called I would accept.

ShyTammy
ShyTammy
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6 Comments
LatexSolarBeefLatexSolarBeefover 3 years ago
Ch. 3

Give us Chapter 3, please!

AnonymousAnonymousabout 5 years ago

Hot story about Emily as a crossdressing hooker. But how did she find herself and become Emily? Her story is only half told. Did she ever reconnect with her accepting siblings? (Screw her hateful parents.) The "youth minister should be in prison. It is not easy being a t-girl.

AnonymousAnonymousover 6 years ago
my first comment

Tammy your stories are all wonderful I have never made s comment to anyone here but I just had to tell you how great you write, and I think your a even better person. Please keep up the good work and making all your readers smile and happy.

THANK YOU TAMMY

PS AND EMILY

ajignatsajignatsover 6 years ago
Awesome

I love the story so far.

This is my first story from you and it’s fantastic so far.

Excited to read the rest.

ShyTammyShyTammyabout 7 years agoAuthor
Thank you Sexy

I Love the feedback, you are so sweet! I have a tendency to work on multiple stories at a time, so sometimes I publish in bursts. I am working on Emily's story and Ch3 will probably be the next thing I post, though getting her to sit down and write with me is kind of like pulling teeth LOL. She is such a procrastinator! I am also working on another story from my life and another story someone commissioned me to write. I will have to get permission from the requester to post that one, though I think she'll say yes. Thank you for continuing to read my stories! You keep me writing!

Kisses,

Tammy

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Emily Ch. 01 Previous Part
Emily Series Info

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