Walking the Path

This story is another 'one off' I wrote while my other series was in limbo. While the concept in my head was pretty clear, I found this story kind of took it's own direction, so I just went with it. As a novice writer I'm not sure if that's a good thing or not, but I decided to submit it.

Anybody who has taken the time to read my stuff knows I like complex characters, who above all things, want to be good people. I try to make the sex stuff work with the mood and direction of the story, and I rarely progress in a straight line.

I hope you find something in the context that you enjoy or identify with. My apologies for any missed grammar or spelling mistakes.

Cheers,

C_T

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Walking The Path

For the second time today, I was in the lane getting my knees dirty. The lane was a narrow path located just off the school's main auditorium, shaded by high backyard fences and an abundance of overgrowth from the trees and shrubs; it's where all the cool seniors hung out before school and lunch hour. I wasn't technically classified as one of the cool kids, but I had a certain type of relationship with a couple of guys from our basketball team... they were the definition of cool.

It was 2:15 and instead of being in my geography class, I was skipping class with Antonio, or Tony as his buddies called him, but I'm not really his buddy. Our relationship is a little different, a little more private... sensual. Ok, I'll just come out with it... I'm his cocksucker. While there were plenty of girls in my school who would or could suck a dick, I was in a whole other class, both in talent and gender.

**

My family and I knew I was different from a very young age, but it wasn't until I turned 18, and in my senior year, that I began to embrace those differences. My father, retired military, had tried very hard to steer me away from my natural tendencies, but he was met with disappointment repeatedly. He was never mean or violent towards me and deep down I knew he loved me, but his frustration was hard to hide. My older brother, Luke (also military) was even less happy as my father, but both my parents had ingrained that family is family no matter what. The only way my brother could deal with me was by ignoring me. It was a painful reality, but I also respected him for still thinking of me as family.

My younger sister, Alicia, was the polar opposite and while she was 3 years younger than me, we had the most things in common. We had pooled interests in music, movies, clothes, and we shared much of the same physical attributes. My father and brother were the classic "brick shithouses". Tall, wide, muscular... a man's man so to speak. Alicia and I took after my mom's side. The petite Latino was blessed with thick long, dark hair. Expressive, captivating brown eyes and a large mouth surrounded by the thickest of lips. She was curvy like a real woman, with larger than average breasts, a flat tummy, thin waist, all ending in the stereotypical Latino booty, full and round like an apple.

Alicia got a bit of our fathers height, as she was already taller than me. She got all of mom's female charms, but with slightly longer legs. In a word, my little sister was going to be a bombshell, breaking hearts all across St. Paul. As for me... I was a little more eclectic. While my hair was thick and wavy, it was closer to sandy blonde like my dad's side. My eyes were more grey than blue, also attributed to my fathers lineage. I had my mothers round face, complete with the mouth and lips. I had always been thin (the skinniest in my house) but my mom always said it augmented my sleek musculature. However, my thinness disappeared after my waist and my bottom was all Lopez (my mom's side). I wasn't as curvy as Alicia, but you could never mistake my hips and ass as masculine. At 5'5" everything about me screamed feminine, except for the larger than average appendage between my legs. My mother referred to it as my pleasure curse, the O'Connor men were legendary for the size of their junk. It seemed like a cruel joke or a waste to put an 8-inch, fat cock on a person like me, but my mom told me god never makes mistakes.

My name is Samuel O'Connor. I prefer to be called Sam.

**

"Oh, fuck you're good at this Sam!"

Antonio had both of his hands on the back of my head as he drove his big cock into my throat. It was easy for me to do, and I loved the feeling of having a guy trapped deep like this. I spent a few years practicing on anything phallic shaped until my sister bought me my first lifelike, suction cupped dildo. 10" long, 5" thick with balls too. It had become a regular in my throat.

It was almost comical how a typical 40-minute class period was the perfect amount of time to suck a guys cock. It never felt rushed although there were times, I wish it could go longer... like right now. Antonio had such a nice fat cock, and his big balls never disappointed. When you suck a guys cock often enough, you pick up on his signs when he's getting close, and I could tell by his rapid breathing and contracting butt cheeks he was about to blast me a mouthful.

I pulled my mouth back till just the fat head was between my lips and I began a gentle massage of his balls, encouraging them to send me everything they had.

"OOOHHH FFUUUCCKKK!"

Yes... here it comes! There's no way to describe the pleasure one feels when the first, rapid jet explodes into your throat and tongue, followed by a series of 5 or 6 more filling your oral cavity with its' creamy goodness. I've cum myself from sucking a dick like Antonio's, but here on school property, I have to keep a lid on that. Thank god for tight yoga pants and miniskirts!

As experience has taught me, he's always too sensitive after he cums, so I just let him soften in my mouth and gently released him, watching him tuck my treat away.

"I don't know how you do it Sam. Nobody even comes close to you and your mouth."

"Not even Betty?" I teased him. He's been dating Betty for 2 years and everyone knows she hates sucking dick.

"Real funny Sam. We should get back though. I'll head back now, and you can follow in 5 or so?"

"For sure Antonio. Thanks!" I gave him a smile and a tiny wave as he headed back for, what would be the final period for the day.

I watched him jog back until he got to the side doors and chuckled at how much my life changed this year. Much to the disappointment of the men in my family, I wanted to embrace my more feminine side and with encouragement from my mom and sister, I started wearing skirts with leggings or stockings, and a variety of more feminine tops. I wore my hair in a pony or pigtails now and even dabbled with light makeup, mostly eyeliner and lip gloss as my mom said less is more.

A drunken encounter with a classmate Peter in his basement, after one of his parties this past summer, which ended up with his cum in my stomach, was a catalyst for my new life. While I have met some resistance and even some types of bullying, most of the people in my school and area have been quite good with it. Sucking the cocks of some of the more popular and bigger guys has also come in handy as they secretly watch my back behind the scenes.

By all accounts, my senior year was the best year of my life. I was sucking cock almost everyday and sometimes twice a day. There was Peter, Antonio, Marcus, Jimbo, Steven, and Predrag. Those were just my fellow students; I also had a few occasions to swallow some faculty spunk too. Mr. Jackson, our head Janitor, was one of my favorites and I always volunteered for cleanup after dances, and boosters or any other school function that required a big clean up. Mr. Jackson was always happy to find a hidden place in the school to feed me his big black cock. He was older and a part of me felt like I was taking him back to his youth every time he fed his 'pretty girl'. I think he was married but I knew better than to ask those kinds of questions. Nothing kills a mood more when you poke around someone's moral compass.

Graduation was difficult for me, even though I had a lot of secret friends, no one had the nerve to take me to a function as a date. I knew my mom was disappointed but deep down I think my father had a breath of relief. So, instead of going to my prom, I worked with the clean up crew made up of junior students, faculty, and janitorial staff. I still remember the look of surprise and sadness when Mr. Jackson saw me sweeping.

"Sam... my pretty girl, why are you here cleaning? Shouldn't you be off at some party losing your virginity?" He was clearly trying to make light of things for my benefit.

"No special night for this Cinderella. No one wanted to be outed by taking me as a date, so here I am."

With his hands on his hips, he looked at me, then around the room watching others clean up.

"So many stupid boys in this school. In my day I would have been pounding down your door to take you."

His kindness made me smile... and blush, I'm sure.

"When you finish this section come see me in my office in the basement, ok?"

"Of course!" My smile returned to my face. The night wasn't going to be a complete loss thanks to Mr. Jackson and his black cock.

Twenty minutes later I made my way to the stairs, making sure no one saw me exit the room. I walked past the locker rooms and showers smiling to myself thinking about all the boys cocks I ogled over the years, until I came to a small dark door that had the words 'Head Janitor' on it. I was about to knock when the door opened in front of me was startled by the unexpected action."

"Oh!" I squeaked.

"I'm sorry Sam. I saw you coming and wanted to minimize any noise."

His apology was weird as I wondered how he saw me coming through a door. He gently took my hand as we walked past his desk and into another smaller room. It wasn't much bigger than a closet but there was a small table, a chair and what looked like linens and pillows stacked in the corner. When he closed the door, I could see a small monitor in the corner that was behind the door he opened. It was a split screen image that looked like the hallways leading to the locker rooms. He saw me look at it and gently cleared his throat.

"I installed them a few years ago, it helps me keep tabs on people as they come to my office."

He could see the questioning look in my eyes.

"Think of it as a silent alarm Sam. It lets me know if I need to be prepared."

If he thought his explanation was helpful, he was grossly mistaken. I went to open my mouth, but he interrupted me.

"I guess you can keep a secret huh?" I nodded my head curiously.

"Let's just say there's more than a few women that work at this school that like to take a ride on good ol Mr. Jackson's pipe. I almost got caught one time when the principal randomly came looking for me, so I installed the cameras one weekend when the school was empty."

I smiled at both his ingenuity and his secret sex life.

"Can you tell me who? You know I'd never tell, besides I'm out of here in two weeks!" I gave him my best pouty face.

I could see him wrestle with my request until a soft smile broke at the corner of his mouth.

"Would be nice to actually tell someone..." He started. "You promise! You'll never say anything? It would ruin my career not to mention several relationships and marriages."

I sat in the chair and nodded animatedly, excited with the dirt he was about to share.

"There's been quite a few in my 15 years here, but you won't know any of those people. I'll just tell you about a few current ones... excluding my pretty girl of course."

I always felt so good when he called me that!

"Let's see... there's Mrs. McQuewen, the math teacher. Her husbands older and has ED problems, so once a week she comes down here for some deep dicking."

I squirmed in my chair. I had Mrs. McQuewen last year and the revelation that she liked to get fucked by Mr. Jackson got my motor running.

"Janet, the librarian... she mostly just jerks me off, with the occasional blowjob, but she's just a curious size queen. That new drama teacher, Linda, now there's a real firecracker! She's knocking on my door a couple times a week now.'

I was giddy with excitement learning about the secret lives of our faculty.

"I'm pretty sure Mr. Lem, the junior physed teacher, is gay. He keeps dropping hints but I'm not gay. The only other one is Mrs. Lawson."

"Mrs. Lawson? As in Mrs. Lawson the vice principal?" I was shocked and he chuckled at my reaction.

"For 6 years now. Freaky one that ol gal. Works out religiously, her ass is so hard you could break walnuts on it. Yeah, good ol Elle..."

I could see he was replaying some fond memories of her. He leaned down until he was right near my face.

"She loves the anal sex that one! I have no idea how she can walk out of here some days!" He smirked.

I was glowing with all this information, and I was also horny as fuck now! I could tell he was too when he stood up, his big cock grossly tenting in his blue work pants. Instinctively, I reached out and ran my hand along the lengthy girth.

"But you... my pretty girl, will always be my favorite." He smiled at me.

"Save the sugar Mr. Jackson, we both know you're about to get your cock sucked." I giggled.

He stood patiently as I unsnapped the waist an pulled his zipper down. I gently pulled his pants and boxers down his legs, getting a nice tap in the face from his hot, hard cock. I continued until he kicked off his works shoes and I removed his garments completely. I sat back up and took in his glorious sight. I don't know why but a moment of sadness hit me when I realized that my special moments with Mr. Jackson would be coming to and end soon with my graduation. I gave my head a little shake to get the negative thought out of my head and reached for my candy.

"I'm going to miss this too Sam, very much."

I looked up at his sad smile, amazed he was thinking the same thing I was.

"It's a shame you never got the whole prom experience pretty girl. You deserve to be happy."

"I am happy Mr. Jackson. I'd rather be here right now then on a sympathy date." He stroked my face.

"Sam... I'd like to give you a proper graduation present if you'd let me."

I was shocked... why would he buy me a gift. It was so unnecessary, after all the fun times we had together, but the look on his face led me to believe this was no ordinary gift.

"I'd like to take your virginity tonight, if you'd let me, Sam."

I have no idea what my expression looked like, but my mind went into overdrive.

Take me virginity? But he knows I'm actually a boy! My god, no one's ever offered before... Should I? Fuck it's going to hurt!

"I... I didn't think you would be interested in something like that with me, you said you weren't... gay."

With his hand on my face, he gently gestured for me to stand up and I did. He took a small step back and gave me a slow, up and down, once over.

"Sam... you're all girl no matter what you got between your legs. I just wanted to, maybe give you something to remember the good times while you were here. I'm not going to do anything you don't want to... I just wanted to let you know I'd like to."

I could tell he was studying my reaction and despite any argument that I could come up with, the ultimate answer to his question was going to be yes. Yes, because it's him... yes, because I've been curious and yes, because I wanted to have the real prom experience.

"You promise to be careful? I know it's going to hurt, and it doesn't help that you are... big." I gulped.

"Hurting you is the last thing I want to do pretty girl. Now why don't you remove those tights and skirt."

I was so charged up at the moment. A combination of knowing what was going to happen and undressing in front of a man for the first time was off the charts! I carefully pulled my tights and panties (yes, I wear panties!) down and pulled them off over my feet. I stood for moment and was about to undue my skirt when he reached out to my arm to stop me.

"On second thoughts... I really like that skirt on you."

I smiled knowing all men loved the schoolgirl skirt. His eyes dropped to my groin, and I could see a question in his eyes. I looked down to see if I could figure out what he was looking at when he reached out and lifted my tented skirt. His eyes went large in surprise.

"Wow... pretty girl is sporting some serious cock! I always thought the feminine white boys had tiny dicks, but that's the complete opposite of tiny!"

I panicked for moment thinking I just ruined my graduation present, but he quickly put my mind at rest when he saw my panic.

"It doesn't change a thing for me." He made me turn around and his big hands were all over my ass. "I've admired this curvy ass all year pretty girl. It's going to look so sexy stuffed with my black cock."

He gently bent me over the small table and grabbed a jar a Vaseline from shelf nearby.

"Compliments of Mrs. Lawson." He winked.

Squatting behind me I could hear him applying the lubricant to his erection as his tongue explored my virgin hole. Shocks of pleasure ran through my spine as his tongue probed and licked around my tiny knot. He introduced a finger that was slick with Vaseline and played ring around my rosie, before gently inserting itself past the tight sphincter. Surprisingly there was no pain... just a sense of exhilaration. One finger slowly became two, now he was standing behind me rubbing his hard, slick cock with one hand while he worked a third finger in, stretching my hole from side to side and in tiny circles.

"Ok pretty girl... I think you're ready." He whispered in my ear giving me shivers throughout my body.

His fingers made a slow exit from my asshole leaving me with an empty feeling. He stood behind me and hiked my skirt over my waist and pulled me back just a little. One hand was gently trying to pull my cheek aside as the other was guiding the head of his big cock to my little hole.

"Be an angel and pull your cheeks open a little for me pretty girl."

Without hesitation, I reached behind with both hands and pulled my butt cheeks apart. This gave him more space to work with and he used one finger to massage my ring while the other hand pressed his big cock head with slow determination. I could feel my asshole giving away, it was getting painful and part of me wanted to tap out, but a bigger part of me wouldn't let that happen. No sooner did I lose my internal debate, did his head pop past the tight sphincter, and stopped. I know I yelped from the sharp pain and surprise, but it was his deep groan that got me through it.

"Oh my... FUCK, you're tight!"

He just stood there moaning while my breathing evened out and that's when he did a little circle with his cock and pushed a bit deeper. It hurt, but nothing like the initial cherry pop. I wiggled a little to let him know I was good to go. He pulled back and pressed forward moving another inch or so deeper. I knew he was being extra careful, but my own patience was wearing thin. I wanted this more than anything, so on his next out and in maneuver, I gritted my teeth and pushed back until I felt my cheeks bump his pelvis.

"Oh holy... holy fuck you're so deep! Don't move! Please don't..." I begged like my life depended on it. My lack of patience was clearly a rookie mistake, and the pain was through the charts right now. Mr. Jackson gently rubbed my low back and bottom, groaning at the tight grip I had on his big cock.

"So good pretty girl... so fucking good! Squeeze my cock honey!"

I did as he asked, and he moaned even more. I noticed the pain was less when I relaxed, so I did it over and over and it was making us both feel good.

"Now comes the real fun." He growled lightly and pulled back a few inches and drove it back home. He hit something that shot straight to my cock and the sensation was incredible.