High School Reunion

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High school reunion leads to a little anal between classmates.
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All characters are over the age of 18.

***

Finally walking off the plane from my first class seat on a Thursday evening. It feels good to be home. I'm back in town for my 10-year high school reunion. This time I'm going to be the one everyone's jealous of. I've got the perfect job, making more money than I know what to do with. Well... being an accountant for a huge tech firm, I obviously invest my money to earn interest and make more money... but my point being, I'm far better off than all the people I went to high school with. There's no way any of those jerks are making as much money as me. Especially Logan Hanson and Devin Bates. Those assholes made my life hell in high school. There's no way they're better off than I am.

Logan maybe, he was at least smart enough to get good grades, Devon, on the other hand, was a complete tool and an absolute idiot. Unless he made it to the NFL, which he didn't, there's no way he achieved anything with his life. But it's Logan I want to show up. He always went out of his way to put me down. He tried to act so manly, but honestly, his voice sounded so girly. I'm surprised Devon didn't give him shit for it. Even though he was shorter than me, being the state champion in wrestling, he had the advantage. Every chance he got, he'd wrestle me down and put me in some kind of humiliating headlock to force me to submit to him. He wouldn't let me out until I said some kind of self-degrading thing. Of course, a lot of the time I probably instigated it further, I could never keep my mouth shut.

Anyways, it's finally time to show those assholes up. As I leave the TSA check-in, I see my mother waiting for me. "Hey honey, it's so good to see you!" she says. My mother hasn't changed a bit. Still has the brighter than the sun smile, with the natural curves and her golden blonde hair. She hasn't aged a bit.

I pull her in a hug, lifting her off the ground. "It's good to see you too, mom."

After I let go of her, she holds me at arm's length and gives me the motherly once over. "I like the new hairstyle. Short on the side and long on the top, it's so professional! You look so grown up with the well-kept beard. My baby's all grown up!"

"Thanks, mom."

We walk over to grab my bag as she fills me in on all the gossip our small town thrives on. "Lucy found out her husband was having an affair with another man, she kicked him out! It's been the talk of the town!"

"Sounds like some things never change," I mutter.

"You can say that again, of course, everyone has pretty much ostracized Greg since they found out he's gay. I don't see a problem with him being gay, it's the whole cheating thing that bothers me," she carries on. My mother has never been one to judge a person based on sexual orientation or anything like that, she's fairly open-minded... But she takes honesty very seriously. Betray her trust and you've earned a spot on her shit list, especially since my dad cheated on her many times over. That's why he's no longer in the picture.

"I feel so bad for Lucy, she's such a nice woman and to go through the shame of being cheated on... It's just so sad," she says as I grab my luggage and we make our way out to her car.

"Kai, you know I don't care if you're gay, right? But you better promise me no matter who you start dating, never ever cheat on them!" Even though I'm not gay, everyone seems to think I am for whatever odd reason. I've dealt with it my entire life, I've kind of just go along with it now.

"Mom, I'm not that kind of guy," I tell her kiddingly. "Give me a little credit, will ya?"

"You're right, I raised a good boy," she says as she opens the trunk and I set my bag inside.

"So where do you want to go to eat?" my mother asks as we get into her car.

"Hmmm, so many choices... How about that Chinese place I love!?" I ask.

"Sorry honey, it closed last year..."

"What!? No way!" I can't believe they would close! They've been open since as long as I can remember...

"I was just as surprised as you were... Hey, there's this new Mexican bar downtown. Want to try it out?" she asks.

"Sure, why not."

It takes us an hour to get to our little town from the airport and we finally arrive downtown. Mom parks the car in a small lot and pays the meter. It was only a couple of blocks to the little Mexican restaurant, called the Cantina. It's a small little joint, in the back alley behind the main strip through downtown. My mom calls it cute. It's a blend of different colors, bringing out the stylish Hispanic culture with all sorts of decorations from little Mexican sombreros in the center of each table to the ponchos the wait staff wear. Truly makes you feel as if you were in Mexico. It was sort of busy, but we managed to get a seat at the outside dining area.

"So, how is work going?" my mom asks as we browse the menu.

"Ehh... I'm making good money, but I still feel like I'm at the bottom of the totem pole. I mean come on, I've been working there for 4 years now. I've pulled more than my fair share of work and yet I feel like I still get no respect," I tell her.

"Oh don't worry hun, you'll get there. It takes time. Just keep plugging away."

"I don't know, I've been thinking of leaving for a while now," I admit.

"If that's how you feel, then you should do it. I would just have something lined up before you just up and quit," my mother says.

"You're right." The waitress comes over and takes our orders. I get the three cheese quesadilla and a beer. My mom orders a tossed Mexican salad and a margarita.

"So... Any special girl in your life? Or guy?" she asks.

"Like I have time for a relationship with this job. I'm working 60 hours a week." The waitress brings us our drinks and I take a sip of my beer. I notice a cute girl sitting by herself at the bar. She's got short dark brown hair, shaved on one side. She's sporting a black skirt with black leggings and a pair of black knee-high boots. She's got on a pink tank top and that's when I notice she's kind of ripped, especially for being so small.

The waitress brings out our order and we both dig in. It's so delicious. Wow. The three different kinds of cheeses blend together in perfect melted harmony and you can taste each of the three kinds of cheese. "Oh my god, this is so good! How's yours?" I ask.

"Oh it's amazing," she says.

It doesn't take us long before we finish up. The waitress drops off the bill after she picks up our empty plates. I pull out my credit card and pay before my mom gets a chance to.

"Oh honey, you don't have to pay when you're at home," she says.

"No mom, I should definitely pay. It's not like I can't afford it. Besides, who else am I going to spoil with all my money?"

"You're too kind."

"Hey, I think I'm going to hit up the bars and see if I can run into some of my old classmates if that's alright with you."

"Oh that's totally fine, we'll have plenty of time together later. You're here till Sunday right?"

"Yep, great! I'll make it up to you tomorrow." I say as I walk her out of the restaurant and give her a big hug.

'Thanks for dinner, hun. Next time it's on me."

"Oh, you don't have to, mom. I can easily afford to treat you to a few dinners."

"Well, have fun and call me if you need a ride."

"Okay, mom. I love ya."

"Love you too."

With that, she walks out and I head back into the bar. A seat's still open next to that cute girl with the short hair. I walk over. "Is someone sitting here?" I ask.

She turns to me and her face lights up in surprise. "Kai?" she asks with a familiar voice.

"Yeah... Do I know you?" She looks familiar, but I definitely would remember meeting a girl like her.

"Well, it's a little complicated... But you look good... Really good," she says as her eyes travel up and down my body. "By the way, no is sitting there."

I take my seat and face her. I look into her eyes to solve the mystery that is her. I feel like I know her, but I can't put my finger on it right now. "Why's it so complicated?"

She stares back at me and I can tell she's nervous. "It's... It's a long story."

"I've got all night." She glances away for a moment, before looking back into my eyes.

"Fine... I... uh, how do I put this. I graduated with you."

"I don't remember you... What's your name?"

"Well... It's Noelle, but... I used to go by Logan." I can't help but blink.

"No way! It can't be..." I look deep into her eyes. "Holy shit! I can't believe it!"

"Yeah... I ah... I just want to say... I'm sorry... I was a total jerk to you in high school," she says as she glances away. I'm still shocked at this revelation.

"Yeah, no kidding... You were definitely an asshole. I literally hated your guts. I still can't believe how much you've changed. I would have never guessed in a hundred years that you would end up being transgender," I admit.

"Yeah... Honestly, I kind of knew all along deep down. I think that's why I was such an asshole to everyone. I wanted to make everyone think I was some kind of macho manly dude so they wouldn't see the truth..." She looked away with the saddest expression. "The truth being that deep down I felt more like a girl, than a guy."

"So that's why you were so mean to me?" I ask, she looks back at me, staring deep into my eyes.

"No, not really. Honestly, I had the biggest crush on you and I sort of enjoyed being rough with you. Seeing you humiliated and embarrassed kind of turned me on. You don't know how many times I've wanted to fuck you after I wrestled you to the grown and put you into a submission." She had that sadistic look in her eyes, the same one I remember all too well in high school. "I know it's fucked up and I've always felt so guilty about it. I really never truly wanted to hurt you, I just wanted you and I was afraid of what other people would think if I actually admitted my feelings, especially what you would have thought of me."

"So instead you just continued to humiliate me?" I ask with a hint of sarcasm. "Definitely see the logic there."

"Hey... High school was a confusing place. It's really more like a ruthless prison than a place of learning. It just felt like you either had to be the bully or be bullied. I just wished I was more like you. You were never afraid to do the right thing or speak your mind."

"Are you kidding me? I was deathly afraid of you and Devon. I avoided you both at all cost. I just hid behind sarcasm, not that it did me any good." She grins at me with an innocent smile.

"I wish things could have been different. Maybe we could have been friends or something more." She takes a long sip of her drink. "By the way, Devon is an asshole and I regret hanging out with him."

"Haha, yeah I wonder how his life turned out so far... " She lets out a laugh.

"He's definitely a deadbeat somewhere, probably a bum." We both share a laugh at that.

"By the way," I tell her. "I don't see why we can't be friends now."

"Maybe something more?" she asks. "I mean... I know you're gay and I'm sure a transgender girl isn't really your type... But... I still have a dick... so... I would gladly fuck that ass of yours! If that's what you're into. Besides, I'm sort of a dominant top, if you couldn't tell."

"I don't know why everyone thinks I'm gay, I'm not gay," I tell her.

"Really!? No way!" She looks at me in disbelief. "If you're not gay then how come you've never had a girlfriend?"

"Because every girl thought I was gay!"

"Oh... I guess that makes sense... I'm so sorry. I feel so... stupid." She looks down in embarrassment, tearing her gaze away from mine.

"Forget about it, you're not the only one who makes that mistake."

"So obviously that means you don't want something more..."

"I never said that either, I mean... I don't know. This is all so..."

"All so sudden? Confusing?"

"Yeah..."

"I understand if you want to take time and think about it."

"You want to go for a walk?" I ask.

"Ah... Sure... Definitely. I'd love to."

I wave the bartender over and put my credit card down. "I'll get her tab as well."

"You don't have to do that."

"Don't sweat it."

After I pay, we head out of the bar and stroll down the alley, making our way towards the main street through town.

"So... ah... What have you been up to since high school?" I ask as I shove my hands in my pocket, not sure what else to do with them.

"Well, that's sort of complicated."

"It seems like everything with you is sort of complicated." She lets out a laugh.

"You could say that. Well, I was recruited by this private company to deal with problems after I graduated college."

"So when did you start to transition?" I ask nervously. "If you don't want to talk about it, don't feel like you have to."

"Don't worry, I don't mind talking about it," she says as she lowers her gaze down to the pavement. We finally arrive on the main street and start making our way towards the drawbridge that separates the south side of town from the north side. "I actually started transitioning in college. I walked in on my roommate crossdressing. He thought I was going to freak out, but I completely understood. I kept his secret, eventually started asking questions. Finally, I partook in it and discovered how good it felt to wear women's clothes. I think that's when I finally realized, that this is who I really am."

She paused after we made our way down the steps to the channel, looking out at the water... "When I finally got the courage to come out of the closet, it was rough. My teammates on the wrestling team didn't accept me. I got bullied quite a bit from them. I ended up quitting. I guess... that's karma for you."

I couldn't help but feel sorry for her. I reached over and grabbed her hand, interlocking our fingers together. She looks up at me, I can see the pain in her eyes. I brush a stray strand of hair from her face, softly rubbing my thumb against her cheek. She wraps her arm around my back. I lean in and place my lips against hers. My thumb continues to stroke the soft skin of her cheek as her tongue seeks entrance into my mouth. I let her in and our tongues embrace each other.

Finally, she breaks away and looks into my eyes. "You want to go back to my hotel room? I've got a few beers in the mini fridge."

"I would love to. What hotel are you staying in?" I ask.

She points across the channel to one of the most expensive hotels in town, I almost burst out laughing. "And here I thought I was going to come into town and show you up with my success. It looks like you've made out quite well in life."

She smiles. "I guess solving problems pays well. Where are you staying at?"

"I'm at my mom's for the weekend. Speaking of parents, how are yours handling all of this?"

"They've pretty much disowned me, although my sister and I are still close."

"Oh... I'm sorry..."

"Don't be, I didn't come here for them." She gives me a sad smile and leans into me. I wrap my arms around her and pull her close. She hugs me tightly, nuzzling her face against my chest. She leans up and our lips connect once more.

Finally, we make our way back up the steps and cross the bridge hand in hand. As we make our way up to the hotel, the entrance is made out of complete stone. The inside is equally as impressive. A lush, rich carpet covers most of the floor. The steps leading up to the reception desk is also made out of stone. Off to the side is a giant fireplace made with giant stones as well. I follow her past the lobby, down the hall, we take a few turns and go up a flight of stairs and we finally stop in front of the door to her room. After she slides her card, we head inside. The room is amazing. A huge queen size bed comes out from the far wall, two bedside tables on each side with lamps on top. There's a nice sofa against the wall to the left of the bed and a sliding glass door that leads out to the balcony. On the ride side of the bed is a little jacuzzi with the bathroom on the other side. There's a door to the bathroom directly to my right and a small spot with a microwave, sink and mini fridge underneath between the door to the bathroom and the jacuzzi. To my left is a dresser with a flat screen TV on top and a desk on with a comfy office chair on the other side of it.

She walks over to the mini-fridge and grabs two beers then hands me one. "Thanks," I say.

"You're welcome," she says and I follow her over to the sofa. "So... I've told you my story, now it's your turn."

"Well... there's really not much to tell. I just studied my ass off in college. Got an accounting degree and started working for this tech firm called Vortex straight out of college. I make good money, but the job itself isn't the best." She listens intently as she takes a sip of her beer.

"How come?" she asks.

"I feel more like a glorified assistant, than an actual accountant. Most of the time I do a lot of accounting bitch work if you know what I mean. I've been there 4 years and I still feel like they treat me as if I was an intern," I admit.

"Well.. not to be mean or anything, it's because you're kind of a pushover," she says bluntly. "You were in high school and you still are."

"Wait to put it bluntly," I mutter.

"I'm not saying it's a bad thing, well... What I mean to say is that you're a nice guy. One of the good guys. Which, unfortunately, also means you're easy to push around." She scoots a little closer, legs touch.

"Well at least you're honest," I say.

"It's one of the many reasons why I like you, most guys are assholes." She places her hand on my thigh.

"True..."

She bites her lip as her hand slides up my thigh. "Ahh.. so..." before I could even finish what I was going to say, her mouth attacks mine. I somehow manage to put my drink on the side table as she starts to crawl on top of me, pushing me down on the sofa. She spills some of her beer before she puts hers on the table. Finally, I breaks away from the kiss.

"So... how exactly are we going to... ah... do this?" I ask her as she straddles me, pulling off her tank top to reveal a set of rock-hard abs and a small pair of breasts underneath a black lace bra.

"I know you're not gay, but I desperately want to fuck you," she says as she grabs my wrists and pins them above my head, leaning down once more to kiss me.

Finally, I pull back and look her in the eye. "I don't know... I've never actually done anything like this."

"Obviously," she says, rolling her eyes. "Have you ever stuck it in a girl's ass before?"

"I... I'm still a virgin," I admit, tearing my eyes away from her in embarrassment.

"Really? No way! How has no one claimed you yet?" She releases my wrists and places her hands on my face, bringing my gaze back to her eyes. "I want to make you mine," she says as she presses her lips softly against mine. I wrap my arms around her and hug her tightly against me.

She pulls back and looks deep into my eyes. "Let me take your virginity away, I'll be gentle... I promise."

"Like stick it in my ass?" I ask nervously.

"Yes..." she says, biting her lip once more.

"Will it hurt?" I ask.

"Just a little at first, but I swear I'll be gentle."

"Can I fuck you?" I ask. She sighs and contemplates what to say. After a few seconds, her face lights up with an idea.

"Want to wrestle for it?" She asks. "If I win, I get your ass... If you win, you get mine." She's got a wide smile on her face at the thought.

"No way! You were all-state in high school. I wouldn't stand a chance." She sticks out her bottom lip and pouts.

"Oh come on, don't be a wuss," she says. "It would be so much fun, we can wrestle naked."

"As tempting as that sounds, there's no way I would ever win against you."

She lets out a sigh. "Fine... What if we just take turns?"

"Okay, who goes first?"

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