How I Met Sheri Pt. 01

I woke up as the sun was beginning to rise on the horizon, looking down at the beautiful girl sleeping next to me, and think about the crazy year it was. If you told me a year ago that I'd be engaged, I'd call you crazy. Then I look on the other side of me, and see my other fiancée, yeah it's been an insane year.

Tomorrow is my 26th birthday, this is a story of what happened leading up to when I turned 25.

A little description, and background about myself: My name's James Marshal O'Shay, but everyone calls me Jay. I'm 24 about to turn 25, 6 foot, about 190 lbs, with a hockey physique a lean upper body, with thick legs, and a big ass.

I've been told that I'm good looking, but I just think people are being polite. I have brown hair, that I keep very short, with a neatly trimmed beard, and blue eyes. My father is Irish, and my mother's family is from Sicily. The only thing I'll ever thank her for, is the dark skin I take after her. And I live in Buffalo, NY.

I'm a really confusing or complicated person, while I'm very confident, and know a lot of people. I'm very reserved, who doesn't have many friends, just acquaintances. I've built so many walls around myself, that I won't let anyone get close to me. It's more like I'm afraid to have people get to know me, I figure if my parents hated me so much, why would anyone like me?

Basically I'm a fucked up, and damaged human being. I have several tattoos to prove this, including 'BROKEN' and DAMAGED' across my heart, on the other side of my chest is 'Cursed at Birth'. Along my abs read, 'No Trust. No Love. No Mercy.' I got them during at a dark time, but it does sum up my life so far. Like I said, I'm fucked in the head.

When I was 8 years old, and through my teenage years, I'd sit alone in my bedroom with headphones on listening to music. I'd play Eminem, 50 Cent, Ice Cube, Public Enemy, NWA, and 2Pac, to help me escape my childhood. Rap music made me feel tough, when I wasn't.

In a few days it's my birthday, and I'm about to become very wealthy. My grandfather set me up with a trust fund, worth over $275 million, it'll be the second time he's radically changed my life. The first was when I was 10 years old, when he saw the bruises, and cuts on my back.

When he asked me about them, I made the usual excuse of, 'I fell off my bike'. Like any abused child, I was petrified to tell anyone, luckily for me my grandfather didn't let it go. He was obviously very wealthy, and powerful man in the city. He hired private investigators, who gathered the evidence, pictures, and video of my parents beating me, and of my father coming into my bedroom late at night. To this day, I don't know how the PI got the evidence, but I'm grateful he did.

My grandparents could've went straight to the police to have them arrested, but they didn't. Before his death, my grandpa told me, he didn't want to put me through a trial. As high profile as he was, the story would've made the media, and everyone would know what happened to me. My grandparents wanted to protect me, as much as possible.

My grandparents, and their lawyers confronted my parents, and gave them an ultimatum: sign away their parental rights, or go to jail. Of course they chose option A, there was also a financial payday for them. I rarely saw them after that, the occasional holiday, but they did visit me every night in my nightmares. Even to this day I'm afraid of them, when I do see them, I'll turn around, and flee from the scene.

Starting at a new school when you're 10 years old is hard enough, add to the fact that I was withdrawn, and socially awkward, thanks to the abuse from my parents. The first day of school a few bullies backed me into a corner, and wouldn't leave me alone, until this tiny little girl stepped in, coming to my rescue. Christie saved me that day, and we've been best friends since.

My grandpa could see that I was struggling, and full of anger, as I'm trying to find my place in this world. The only thing I knew at the the time, was the two people I should've trusted, and loved me the most, hated my guts.

I was sent to psychiatrist, counselors, and all kinds of doctors, all wanting to help me. But I'm not the type of person who shares his feelings. I'd sit there for the entire appointment, and not say a word. I wasn't ready or able to talk about the abuse, I'm still not.

One of the counselors I was sent to, was also a youth hockey coach, for kids with similar problems that I have. My grandparents enrolled me right away, since they knew I watched hockey every night with my grandpa, it was our bonding time. As soon as I hit the ice, I fell in love, and was able to break out of my shell.

I quickly became a leader on the team, it was giving me the confidence that I lacked. Not to sound cocky, but I was good, and my grandpa saw that too. By the time I entered high school, I had college recruits, and coaches from Juniors coming to my games. I had zero interest in school, so I chose to play right across the border in Canada, playing in the OHL.

On the ice, and the locker room, I was a natural born leader, but off the ice, I was still broken, and a complete mess. I was captain of my junior team when I was 17 years old, and there was talk of me getting drafted in the next year.

My life was going as well as it ever had, I was having a great season on the ice, scouts were following me around. I finally thought I found my path in life, until I lost both my grandparents within six weeks of each other, and I felt lost again.

When my grandfather's will was being read, my parents, and some other family members were there. My parents never said a word to me, I felt truly alone in the world. Unbeknownst to anyone, my grandpa left his entire fortune to me. When I turned 25, I would be worth a quarter of a BILLION dollars! That was a mind fuck, that I still haven't wrapped my head around.

I had no idea they had so much money. They raised me in a modest three bedroom ranch house, no fancy cars or jewelry, they were down to earth people. My parents on the other hand, who didn't have anywhere near the amount of my money, flaunted what they had, living way above their means.

I truly think, that not only did my father expect to be given the estate, but also the family business, but my grandpa had a little surprise for him. Instead of taking over the company, it was to be sold off, with all proceeds going to charity. I also think my grandpa gave me all this money, as a way of apologizing that his only son, abused his grandson, even though he has nothing to say sorry for, it's not his fault.

If I thought my parents hated me before, this took it to another level. They tried everything to get their greedy hands on the money, they tried to say I was a con-artist, and wasn't mentally fit. Thankfully my grandpa, also left me a very good lawyer, who beat them in court every time.

After the reading of the will, the funniest part was, suddenly I was flooded with calls from cousins, aunts, and uncles. People who barely acknowledged my existence, when my grandparents were alive, were inviting me over for dinner. They didn't give a fuck about me for 18 years, so fuck them now. I'm not a forgiving person, you do me wrong one time, I'm done with you.

The night I buried my grandpa, I hung out with Christie, after everyone left the house, I told her the truth about my childhood. It was the first time I told anyone, she sat with me all night, as we cried together. I felt safe confiding in her, I knew she would never betray my confidence. When we were 16, she told me she was a lesbian, and to this day, I've never told anyone.

A week after the funeral, I did get drafted, and I played nine games in the NHL. What should've been the best time of my life, was actually the darkest. I was a black hole of misery, but at the same time, when I was sent down to the minors, I still played well. After the season was over, so was I, I walked away from my childhood dream, and quit playing.

I began working in construction, just biding my time, until my trust fund kicked in. I just didn't know what I was going to do, all I knew was I wanted to do some kind of charity.

As I got closer to my 25th birthday, I went house shopping. Right now me, and Christie live in a small two bedroom, one bath home. Our new house is, 7,500 square feet, 7 bedroom, 8 and half baths. A nice in-ground pool, an incredible patio, and a theater room. I made sure the house had two master suites, so Christie can stay as long as she wants, it's her house, as much as mine.

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I walked into our small living room, and see Christie on the couch, looking at an old porn magazine. This isn't unusual she loves porn, and has a vast collection.

"I miss magazines." She says, tossing it to me.

"You've heard of the internet, right?" I joked.

"It's not the same, you..." she asked, as she walked into the kitchen, "want anything?"

"Just a Pepsi". I said, picking up the magazine to look through it, when something caught my eye.

The ad was simple, it was a phone sex number: 'Feeling alone, call a horny shemale now 1-800-SHEMALE'. It wasn't the number that's got my attention, it was the picture in the ad.

The girl was pretty, she looked to be Hispanic (my weakness), with long dark hair, large tits, but holding a big cock. It was smooth, with only a landing strip for pubic hair.

I felt my own cock stirring in my sweatpants, my vision became a blur, it felt like a bomb went off in my head. I looked at another ad of a different girl, with an even bigger dick. I was having a war inside my head, I've only been attracted to girls, so why am I turned on now? This doesn't make sense to me. I felt like I was going to pass out.

"What're you looking at?" Christie asked, snapping me back to reality.

"What...I nothing, just..." I stammer, dropping the magazine, "reading a story."

"Says every man when he's caught, let's..." she laughed, as she picked it up, "what's got you so hard."

It's not like she hasn't seen my dick before, we've seen each other naked hundreds of times. She walks around in her panties, most of the day. Christie is a very attractive, five foot, two inch pretty blonde, with b-cup tits, and a nice ass.

I took the Pepsi, and laid on the couch, as the battle rages on in my head. I know I'm straight, I've only been with women, I don't find anything attractive about men, so I know I'm not gay. Then why am I so turned on, seeing a chick with a dick? I had no good answers, so I grabbed my vape pen to get high...very high.

"You want some?" I asked, she put the magazine down, sitting next to me.

"I gotta work tonight..." She said, she works in the ER overnight as a nurse.

"There's nothing you can't tell me." She laid down, to cuddle with me.

I wasn't sure what she was saying, I closed the magazine before she could see anything. If I did have any questions, she would be the one to talk too, but what can I ask her? I was just confused right now.

I must've dozed off, because I was jolted awake, when Christie jumped up from the couch. Scaring the shit out of me, and made her laugh.

"A little jumpy." She laughed at me.

"You jumped like an ax murderer, was..." I said, a little nastier than I intended, "coming through the window."

"Fuck you bitch, I gotta get to work, what's..." she said, dishing it right back at me, "got your panties in a bunch?"

"I'm not, it's..." I said, wanting to tell her about the shemale fantasy in my head, "just...I'm sorry for taking your head off."

"Don't worry about it, but..." she smiled, "you're still a bitch."

"I could be, I do love you though, besides..." I laugh, "who else would want us?"

"I don't know, I think one of us, *might...* she said mysteriously, "have a new prospect."

I looked at her, as I wondered if she had a new fuck buddy, she didn't tell me about. That would be unusual, she shares everything with me, even when I don't want to hear it. Christie gave me a kiss, before she left for work.

I waited for a few minutes after she left, before I grabbed my IPad, and googled 'Shemale'. I quickly learned, that word is as offensive as the N-word or the f-word. I went to Pornhub, to look at trans porn, and it blew me away. There were so many options, I didn't know where to begin.

Some looked like guys in dresses, while wearing make-up, thankfully my dick didn't respond to them. I scrolled down some more, and found what looked like any other pornstar, hot, and slutty looking.

I clicked on a girl named Jessy Dubai, who I thought was a girl, until she pulled her panties off, revealing a huge dick. She began fucking some guy in the ass, which didn't interest me at all.

I seen Domino Presley videos, who is hot as hell, in one of the videos she was getting fucked in the ass. I kept watching her dick flop back, and forth as she got fucked. I wanted to be the guy giving her that pleasure, when she started screaming, that she was cumming, seeing her penis explode was so erotic. I looked down, and realized I was jerking off, and came all over my sweats.

I was eventually able to tear myself away from the porn, and cleaned myself up. I needed to get out of my head, so I decided to go golfing.

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There's no worst feeling, than when you know you have a big day ahead, but you can't get to sleep, and when you finally do, the alarm goes off. That was my night, my mind was racing between trans women, and the inheritance I was getting today.

I got out of bed, to jump in the shower, so I can get to my lawyers office. I was a few signatures away from getting an obscene amount of money. I had mixed feelings about it, excitement, fear, and embarrassment.

Leaving the lawyers office, I felt like I was living a dream. My life will never be the same, I think to myself. I pulled out my phone, to see I missed a text.

Christie: 'happy b'day bitch, dinner/drinks on me 2nite. No arguments.'

Me: 'where we going?'

Christie: 'it's free, but ur coming to Eden with me.'

Club Eden is an LGTB club in Buffalo, that I like going to. I'm not really into the club scene, but Eden is a laid back place. Christie's fucking the manager Mary, plus my ex girlfriend Renee works as a waitress, so we get treated pretty good there.

Me: 'fine, I gotta make a stop & I'll be home.'

I pulled into the parking lot of the dog shelter, and parked my five year old Hyundai next to my dream car, only this car was white. I planned on getting a black Mercedes S-class 560, as soon as I can. I tried looking in the windows, but the tint was to dark. Whoever owns this car, has good taste.

Walking into the shelter, I go straight to Doug's office, who runs the place. I met him a couple months ago about me volunteering here, he said he never turns away help. He's an older guy in his mid-50's, a little pudgy around his mid section.

I really respected what he was doing here, to save these dogs. He didn't start a shelter to become rich, he did it out of pure kindness. I came today, to give him a little gift.

"Jay, what're you doing here?" He asked.

"Just wanted to talk to you."

"Hope you're not quitting already." He joked, as he offered me a seat.

"No, I'm looking forward to it, I just wanted to say, how..." I said, "much I admire what you've built here, and wanted to give you this."

I handed him an envelope, and waited for him to open it. For some reason I felt nervous, my hands started to shake. I'm also feeling happiness, and joy, two feelings I don't have very often.

"What's this..." he asked, as his eyes went wide, when he read the check, "is this for real?"

"It better be, I'm..." I joke, before telling him honestly, "new at this, I didn't have the best childhood, but my grandparents had this little yorkie, who was able to make me smile, when I had nothing to smile about. I **need ** to do this, so please accept the donation, there's no strings attached, if I suck at my job, fire my ass."

I meant it too. If he fired me, I might give him more money, just for having integrity.

"Oh don't worry I will, are..." he laughed, before asking, "sure you can afford this?"

"Yeah I can, but..." I said, "please don't tell anyone."

I really don't want anybody to know about my financial situation. The only person who knows, besides the lawyers, and family, is Christie, who I know will keep my secrets. There's a reason I have 'No Trust' written on my stomach.

"It'll stay between us, this'll..." he said, with a big smile on his face, "keep the doors open a long time."

That's what I wanted to hear, I want the money to help as many dogs as possible. In many ways I like dogs better than people. With dogs, you always know where you stand, they either love you or they don't, they don't fake their emotions. What I like the most about them, no matter what you tell them or what you've been through, they won't judge you.

"I hope so, well..." I said standing up, "I'll see you next week."

"I really appreciate this, it's beyond generous, I..." he said, shaking my hand, "feel like I should call you Mr O'Shay."

"Please don't, that..." I said, "reminds me of my father, and that's the last thing I want."

Doug nodded his head, I think he understood that might be a sensitive topic, and dropped it.

As we were leaving his office, I saw the most beautiful girl I've ever seen. She was about my age, and looked similar to actress Roselyn Sanchez, but a little darker skin. She had jet black hair, that was in a ponytail, high cheekbones, with sparkling brown eyes, and the most kissable lips.

Doug walked down the hallway with me, as the Hispanic beauty approached us, my heart was skipping beats. She had this little smile on her face, like she knew a secret.

"Hello." She said in the sweetest voice, looking me in the eyes. My knees went weak, as butterflies fluttered in my stomach. She acted like she knew me, but that wasn't possible, because there's no way I'd ever forget her.

"I ummm...you...uhhh...h-h-h-h-hi." I stuttered like an idiot. I've never been tongue tied by a girl in my life.

She giggled as she walked by, she knew the effect she had on me. This goddess was wearing scrubs, but I can tell she has a nice body, she isn't very tall, maybe five foot, four inches, weighing 125 lbs.

"That's our vet, I'll introduce..." Doug began to say.

"No, I'll..." I interrupt him, "meet her next week."

I couldn't even say 'hello' to the stunning vet. I didn't want to make a complete ass out of myself, as a first impression. Maybe in the next week, I'll work up the nerve to talk to her.

I look over my shoulder, to check out her ass, and I busted her looking at my ass. She handled it so gracefully, by giving me a little wink, before disappearing through a door.

"She's really an incredible girl, very smart, she's..." Doug said, like he respected her, "not even getting paid, she donates her salary."

Beautiful, smart, sexy, and a big heart, I got to get my shit together, so I can try to talk to her.

I said goodbye to Doug, and headed home. I started thinking; maybe the trans porn I watched, was a one time thing after seeing the hot vet. That confirmed I was attracted to women.

"Don't forget, you..." Christie said, when I walked in the door, "can't wear sweats at the restaurant."

"Yeah I know, I'll change."

I own two nice pairs of jeans, and one suit, the rest of my closet is filled with Nike sweats. I just don't like dressing up, I prefer comfort over fashion. I've worn Nike clothes since I was a teenager, and I doubt I'll ever change my style.

I grab my vape pen to get stoned, as I take a shower. By the time I'm done getting ready, I'm high as a kite. Marijuana is the only way I'm able to function, when I'm around people. If I wasn't high, I would be sitting in a corner, and not saying a word. Some people drink alcohol, I smoke weed.