Emily Ch. 01

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Tammy writes her best friend and roommate's story.
3.4k words
4.39
21.8k
16

Part 1 of the 2 part series

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

Author's Note: I have decided that I would mix in some stories from some of my close friends who want their stories told. This story is about my best friend and roommate Emily. She read my stuff and liked it and asked if I would write hers. She's Trans like me, but comes at it from a much different place. I like to write in the first person so I start out in the form of a chat and transition to telling the story from her perspective; I hope that comes across well in the story. I hope you'll find her story both sexy and compelling. I know I did!


"Hi gorgeous!" I greet Emily as she came into the little dining area of the townhouse we share.

My best friend and roommate Emily is absolutely gorgeous. She's tall and thin with a cute pixy cut. Her hair is strawberry blonde right now, but that changes a lot.

She's dressed casually in jeans and a shirt that is tight and short, showing off her sexy midriff and small perky boobs. It's just us so she's not wearing a bra and her lovely nipples poke through the thin material. I know because we are occasional lovers that she has a wonderful six inch long cock well concealed in her jeans. She's naturally a red head with a fair complexion and she has the cutest sprinkle of freckles across her cheeks. Her bright green eyes are always full of energy.

It was mid-afternoon on a rainy Sunday when we sat down to chat. The kind of day that is good for introspection and long conversations.

"Hi Chica, I just finished reading 'My Life' and I loved it, totally hot."

"Aww thanks; I am glad you liked it." I replied as she gave me a hug.

"I had no idea about some of that stuff; did you really fuck your teacher?"

"Yes" I replied, blushing.

"That's fucking hot."

I just laughed in response as I poured her a cup of coffee.

"It got me thinking..." she started.

"About fucking your professors?" was my snarky reply.

"Ha-ha, no, I already think about that all the time!"

"Ok, what then?"

"Well do you think my story is worth telling?" she asked.

"Of course it is!" I replied, totally excited that she's into it, "You totally should!"

"Yeah..." she replied pensively.

"What?"

"Well it is just I can't write as well as you Tammy, I love the way you put things."

"Let me go get my laptop," I responded smiling "we can work on it together"

Emily's Story

(Emily's voice)

I guess the day I stepped off the bus in Albuquerque, well it must have been fate even though I don't really believe in all that. The day happened to be the same day as the gay pride parade. The streets down town near the bus station were full of happy and proud queers flying their freak flags, rampant sexuality on full display. It was the most incredible thing I had ever seen and the feeling of absolute awe I felt, well I can still feel it today when I think about it.

Looking back on it I almost can't believe the person I was. To me it felt like the whole world had been flipped upside down, it also ironically felt like home. This was supposed to be just a stop in some dusty desert town on my way to L.A. I would of course learn that even bigger cities such as L.A. had bigger Pride events, but nothing would ever match that first time for me. I felt like a house had been lifted from my shoulders. I never did get back on that bus.

I mean there I was an 18 year old kid, running away from home and on my own for the first time. All that I had to my name was a skate board, a backpack with some clothes and the $1,683 left of all the money I had saved for the last two years.

The reason I left home was obvious if you would interact with me for more than ten seconds. I was one of those gay boys who can't hide who and what he is. I was small for my age and very skinny to the point of scrawny with ridiculous bright red hair. I had a lisping way of speaking that I couldn't stop no matter how much I policed my mannerisms. I didn't walk right either; it seemed that nothing I could do was boyish or mannish in any way. I was extremely uncomfortable in my own skin.

I come from a conservative Christian family in a rural part of Oklahoma. My nature didn't mix well with my surroundings. Both of my parents hated and distrusted me since before puberty, I know that sounds awful but it's true. They were not shy about letting me know it. I was an embarrassment at church and a freak at home. Getting caught by my Mom wearing my older sister's underwear, bra and skirt just solidified for my parents what they already knew, I was an abnormality, even worse according to the bible I was an abomination.

When I was 16 years old the harassment at both school and home got so bad that I tried to kill myself, I still have ugly scars on my wrists as a reminder. No one in my community wanted me anyway. I think my parents would have just let me go, but my younger brother found me first and called 911. After that I got some mandatory therapy from a secular state appointed therapist. She was from New York originally and was way more understanding of my sexuality. She helped me understand myself and helped me devise a plan to make it through the next two years and get the hell out.

My parents said they would kick me out of the house unless I changed my ways, I may have been better off if they had, but I complied anyway following the plan. They forced me to go to church several nights a week and join a church youth group. The youth pastor was this creepy older guy who tried to act "cool" and "hip". He failed miserably at trying to fit in with the teens in the youth group.

It wasn't long after my eighteenth birthday that he started to target me. First with a little niceness, of which I was always suspicious, then forcing me to put my hand down his pants and rub him off. It wasn't much longer and he was blackmailing me to suck him off or give him hand jobs two or three times a week. In exchange he told my parents that I was becoming a model Christian, yeah right. At least it kept a roof over my head.

Six months after I had turned eighteen I finally had enough. I had been saving money from odd jobs and holidays ever since the day my therapist and I came up with the plan. I told my parents I had a youth club event in town. I packed a bag, hitched a ride, bought a bus ticket and never looked back.

When I stepped off that bus in the middle of the Albuquerque Pride parade, I found instant acceptance in the world around me for the first time. I was home. I stood on the corner with tears just rolling down my face. I had never been so happy in all my life. I breathed a giant sigh of relief.

When the last of the floats went by I hopped on my skateboard and followed the crowd to the fair grounds. Wow, they had vendors and people and a crazy dance area. It was like a carnival. I just walked around taking it all in. I stopped at the Planned Parenthood booth and got a gift baggie with a condom, lube and some other branded stuff. I also stopped and talked with the people at the Transgender Resource Center. My head was spinning that there was so much to look at.

After a while I did start to notice that there was a key difference between me and almost everyone else out there. I was alone. Almost everyone else was with groups of friends or lovers. I bought a funnel cake and lemonade and sat down to eat it feeling a bit down about things all of a sudden when someone caught my eye.

He was tall and older than me, perhaps twenty eight or so. He looked vaguely Middle Eastern with dark curly hair, a dark complexion and a handsome five o'clock shadow. He was with an apparently heterosexual couple and talking to them with a mischievous smile on his face. Every few seconds he would catch my eye over their shoulders.

After a little bit more eye flirting, he excused himself from his friends and walked right toward me. I watched him walking up and all of a sudden I was extremely nervous. I had never talked to a stranger that I was attracted to and here it looked like I was about to get hit on. My heart was pounding!

"Hi, I'm Miguel." He said, offering his hand and smiling.

"Hi, I'm Brian." I replied offering my hand in return. He took it and brought it to his lips, like a gentleman courting a fine lady. Wow!

(Narrator's note, it was really hard for me to reveal my birth name, which I was still using at that time. It is not who I am today or ever really was. I am Emily and I always have been. I did want to tell the story as truthfully as possible. Now you know something I wouldn't even have told Tammy if she asked. Of course now she knows too because she's writing this for me.)

"You're really cute." Miguel said, "Are you here alone?"

"Yes," I replied, "I'm new in town so I don't know anyone."

"Me too," Miguel said, "I'm helping my sister move here from El Paso, but I still live there."

"Cool"

"Since we're both alone do you wanna hang out?" Miguel asked.

"Yes, I mean sure." I replied bashfully.

We walked around looking at the booths together and talking. I told him of my escape and he totally empathized with me, though his parents and sister were really accepting. I met his sister and her boyfriend at one point, but they left us alone quickly thereafter.

As morning turned to mid-afternoon we ended up near a building and out of the thinning crowd. Miguel pulled me behind the building and started kissing me. I was in heaven! I was so attracted to him and he wanted me. I was so excited my cock was throbbing in my pants as he ground his body against me, pressing me hard against the stucco wall. It felt amazing.

It felt way too amazing in fact, within a few seconds I was trying to squirm away from him because I was going to cum in my pants. I just wasn't used to being with someone I liked. He seemed to know what was happening and he held me tighter. He slid his hand down the front of my jeans and grabbed my cock. Oh god it was so hard not to explode right then when I felt his warm soft hand gripping me. No one had ever touched me before.

"Just let it happen." He whispered intensely in my ear.

My body was shaking and convulsing. I couldn't hold on and my orgasm completely overwhelmed my senses. He kissed me deeply as I pumped hot cum into his hand. It felt amazing, but I also felt so embarrassed. I came so quickly even though we had hardly done anything.

Miguel didn't seem to mind at all. He brought his cum soaked hand to his mouth and gave it a big lick. "Yum." he said smiling. Then he wiped the rest the cum off on a napkin he took out of his pocket. He kissed me again and I could taste my semen on his lips, it was intoxicating.

I could feel that he was still hard. In the same position, with my back to the wall I slid down to sit on my heels, my eyes level with his cock. We both looked around and he unzipped his pants and pulled his cock out. It was long and straight and a nice brown that matched his overall skin tone. I immediately took him in my mouth, swirling my tongue around the head. He groaned in response.

Then I let him push it between my soft wet lips. I had done this part before with that douche from church back home, so I kind of knew what I was doing. The big difference was I really liked Miguel; it really did make all the difference in the world. I sucked him and let him fuck my mouth and I was happy about doing it. When he held my head and started pumping faster between my lips I got so excited. When he finally came, I relished all the hot cum filling my mouth and sliding down my throat. It was like manna from heaven.

After we straightened ourselves up, we wandered around some more, but this time more like a couple. I was so happy. In talking to Miguel I did find out he was headed back to El Paso in the morning, which I was really bummed about, but I decided to just enjoy the time we had.

"Was that your first time?" he asked.

"Well kind of.." I responded hesitantly.

"Didn't seem like it, felt really good." He replied.

"It's complicated." I said

"Well I've got time if you want to explain?"

So I explained about my parents and church and even the creepy Youth Pastor as we walked the fairgrounds holding hands. He would give my hand a comforting squeeze when he noticed I was having a hard time talking about something. I was totally falling for him.

"I wish you were saying." I said.

"Me too, but I have a boyfriend back home." He said without a hint of shame.

"Oh" I said suddenly downcast.

"Don't worry, I mean we're open and all that." he said.

"I don't understand."

Miguel explained open relationships to me. This was an entirely new concept to me and something it took me a while to get my head around. I wasn't super excited about the news, but at least I didn't feel bad for cheating. In some ways it was just information overload. My world had expanded almost as much as it could in one day, or so I thought.

"Let's make out again." He said, seeing I was a bit off.

"Ok" I said as he took my hand and led me between two buildings and behind a bush.

We started kissing and it got pretty heavy with both of us grinding into each other. Then he turned me around to face the wall and started kissing my neck as he ground his cock against my ass. I couldn't help but grind back against him. God this felt so right. I wished I could do this all the time. His hand moved into my waistband and grabbed my cock and squeezed.

"Do you have that baggie of party favors?" he whispered intently in my ear.

"You want to do it here?" I asked nervously, "Now?"

"Yes!" he whispered again, punctuating it with a thrust of his cock against my ass.

I handed him the baggie from Planned Parenthood with the lube and condoms in it. He did something I couldn't see, and then I felt his hand slide down the back of my pants. His fingers were wet with something cold and he immediately found my tight little asshole and started pushing his lubed up finger into me.

I have to be honest here, I was scared and I really didn't like it at first. It hurt a little and felt weird, but Miguel wanted it and I wanted to please him so badly I let him keep going. I started to enjoy it more when he started kissing my neck again.

Then he unbuttoned my jeans and started working my pants down over my hips. I felt so exposed out there in public. No one could see us, but the sounds of the waning crowds were still all around us. This was different than before, more involved somehow. Still, I found that I wanted this more than I was worried about getting caught. I let me push my pants down to about the middle of my thighs.

He frantically unbuckled his belt and then I felt the warmth of his hard cock on my ass. He rubbed it against my ass a few times before he was fumbling again, putting on the condom I supposed.

Then he shuffled behind me again and it was then that I felt it, he big hard head of his cock pushing against my entrance.

"Just relax Baby." He said as he started to push.

"Ugh," I grunted "It hurts."

"Just relax and let it happen." He said again a bit more urgently and pushing harder.

We fumbled around a bit because I didn't really know how to relax in this situation. Then it just happened, he pushed, I did something and he was in me. He was filling me up. It hurt, it felt amazing. I just froze not knowing what to do.

Then he was doing it. He was fucking me. His hands gripped my hips hard. It hurt but there was also something so very right about it that I didn't complain any more. My cock was hard and bouncing with his thrusts, which felt good. I just held on to the wall and took it.

It was so intense, I could feel his hot ragged breath on the back of my neck as he took my virginity.

"Uh Ugh uh Uh ugh uh..." he was really going to town fucking me. He didn't seem like the same person at all while he was doing it. My mind started to worry that we were getting too loud, that we'd get caught, but his cock ramming in and out of my ass was relentless. I could hear my own voice like it was someone else, the voice was moaning, it was just such a needy voice. I realized I was cumming all over the wall in front of me as my body shook uncontrollably.

"I'm gonna cum!" he whispered harshly in my ear. Then I could feel it, his cock pulsing in my ass as he buried it deep inside me.

Then it was done. He pulled out leaving me feeling empty. He took off and tossed the full condom into a bush and pulled up his pants. I was just so shocked and dumbfounded by what had just happened. I was leaning against the wall, pants still down and bunched around my ankles. Eventually I pulled myself together enough to pull them up and sort myself out.

I had just been fucked. I wasn't sure how I felt about it. It had made Miguel behave in a way that scared me a little. There was also something that felt really good about it, though it was hard to place what that was. It seemed like just the right way to do things for me I guess, hard to pinpoint it more than that. I did get off too, so that was really nice.

I wish I could say I was unequivocally thrilled with the experience but that would be lying. I guess mostly because Miguel behaved differently towards me after we were done too. We walked out of the bushes. We kissed but there was no passion behind it anymore. Eventually he said he needed to find his sister and left me alone on Central Ave with nowhere to go.

I threw down my skateboard and just jammed down the street hopping curbs as I went. Eventually I found a row of crappy hotels and checked in to one that had weekly rates. The room was pretty shitty, but it was clean enough for now. I settled in and decided that I was proud of myself. I went out into the world and I had experiences and made my own decisions. I also realized that today was the first full day that I could remember where no one made fun of me, no one took advantage of me, and I felt accepted. I felt at home.

ShyTammy
ShyTammy
458 Followers
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AnonymousAnonymousover 2 years ago

To those who have a problem with the last few lines about not being taken advantage of I think are missing the point. Sure in a normal relationship sense that may be taking advantage, but from her perspective as a person who had only experienced sex in a shameful and abusive way, at least this was consensual sex and that in and of itself is empowering. You shouldn't judge her perspective. I have a similar background and I totally get the feeling of empowerment when you have a sexual experience you agree to an like after all other experiences were abuse. Don't be so judgy.

LatexSolarBeefLatexSolarBeefover 3 years ago
My first

This is the first piece of gay porn I've ever read. I liked it, very well written. I'll read the rest of the series. Thanks.

AnonymousAnonymousabout 7 years ago
Used

Unfortunately, you were taken advantage of, by an older, more experienced male. Then he left you hanging. Hopefully, you have learned from your early naivety.

cdmartinecdmartineover 7 years ago
Great story

A good story line can't wait for the next one

DianeRedfernDianeRedfernover 7 years ago
Beautiful and real - can't wait for the next installment

I absolutely loved the emotions and all of the character development. I certainly want to learn more about Emily and Tammy too. The gay-but-not-really sex was hot and obviously was an important step on the journey to let Emily know who she really is. Very stark emotion, more literature than soft porn (a supreme compliment) but titillating enough to more than exceed requirements of the latter. Please keep writing. I'll be watching for Emily's next chapter.

xoxo,

Di

P.S. I'm not sure how long you've been around Literotica but for whatever reason, it attracts a cadre of trolls with nothing better to do than rag on stories that fit the category perfectly but are offensive to their so-called "moral codes." The bully/coward "Anonymous" (What a coincidence. All these cowards share that name) is obviously one of them. Please ignore him as you would ignore the stench of a passing skunk once identified for what it is.

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