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Drama Suspense Transgender

This story contains sensitive content

CW: sexual content, physical violence, drink spiking, suicide reference

I've been cheating on my wife for around six months now. Emma and I have been together for two years, married for about ten months. She's a wonderful wife, she does a fantastic job of taking care of me. Emma is also pregnant, she's around three or four months along. This will be our first kid and I'm pretty excited, but the pregnancy has been impacting her very negatively. She's sick almost constantly to the point where she's had to quit her job. She's been super irritable and she snaps at me more than she ever has our entire relationship. I'm not one to take her shit, so I'll argue back and she'll inevitably end up in tears every time. It's exhausting.

Not to sound annoying, but I need a lot of attention. I'm proud that I can admit that because a lot of men won't. After Em and I got married, she got much more invested in her career than I would have liked her to and I felt like I took the backseat in her life. Now that she's pregnant, her priorities have further drifted away from me. I don't know if I let her get too comfortable or what, but once I felt her focus shift away from me, the urge to cheat came and it hit me full force.

I've cheated before, but not on her. I've cheated on almost every girlfriend I've ever had. I'm disappointed that I've gone back to my old ways, but I'm not entirely surprised. I've done some research and I discovered that infidelity can be an inherited trait, something about oxytocin receptors in your brain or whatever. It also has a lot to do with upbringing. If my parents instilled anything in me at all, it was that cheating is never a dealbreaker. I hope Emma has that same mindset and in our case that those traits skip a generation. I can't lie, I do feel guilty about stepping out on my Emma. Regardless, I still have needs that must be met and I feel like it’s unfair to dump all my desires onto my sick, pregnant wife. 

I made the decision to to reduce my affairs to strictly dates and their consequential hookups, no more girlfriends on the side. This is partially out of respect for my wife and also because I got tired of the reactions that I'd get from these women when I would finally tell them that I'm married. I've been screamed at, spat on, cussed out, had drinks thrown on me, slapped, I've even had a gun pulled on me! Believe it or not, the women who are fine with it are even worse. They claim to not care about the fact that I'm married and choose to continue our affair, then get pissed when I won't leave my wife for them. I’m not the perfect husband, but I would never leave my Emma for any of those gutter-sluts I date. I've gotten a million and one threats from my affair partners that they're going to expose me to my wife, but none of them have actually gone through with it. If she does know, she hasn't brought it up. That's more than okay with me.

Apparently, my picture has turned up on some local forums that are run by women warning each other of men they've met on dating apps and been scorned by. I can tell because my messages have all but dried up, aside from ladies informing me that they had already heard about me, followed promptly with a block. I was abruptly cut off from my main source of attention and it was pissing me off.

I got onto my alternative social media account that Emma doesn't know about and I sent friend requests to every single one of my exes that I could find. As I rapidly prowl through the people you may know section, I find a profile that makes me freeze up. Alice Flynn.

I never thought that I would see her again. She's my ex fiancée, we dated all throughout college and she was the first girl I ever really loved. I proposed to her our senior year, she accepted and I was thrilled. She decided that she wanted to be a housewife, so we agreed that she would drop out of school and we would marry after I graduated. Her parents were so mad at her for quitting school but they were overjoyed that we had gotten engaged. I got along really well with her family. She had two brothers, one older and one younger, which I became really good friends with. Their names were Calum and Anders, they had some odd names that always stuck with me. She had a little sister, too. She was probably around four years old when I started coming around. She was shy, but once she warmed up to me she became very sweet. I remember us playing together a lot. I think her name was Penny or Patty, something like that. God, it's been fifteen years since I last saw that family. That little girl is all grown up now! I wonder what she's up to nowadays.

Obviously, Alice and I didn't work out. Yes, it was my fault. I've matured enough in those fifteen years that I can finally recognize that. I was twenty-one years old, I was a stupid kid. I don't want to get too much into it but to make a long story short, my nearly four year long relationship ended with nothing but a stint in jail and a restraining order that lasted longer than Alice and I did. I feel immune to regret, but I would do anything to change how things ended with her.

Now I'm on her socials, in awe of her matured beauty. She seems so much brighter than she did when I knew her, I'm relieved I didn't end up ruining her life. I decided to send her a message.

"Hey Alice! It's Duke Redmond. Long time, no talk! I'm very happy to see your smiling face again. I've been thinking about you and I was wondering if you'd like to catch up over drinks? There's some stuff I think we need to talk about. Tell your family I said hi!"

I sent messages in a similar vein to my other exes, only really caring about Alice's response. When I check my messages to her, I discover that she blocked me. It finally dawned on me that the reason she never popped up on my regular account was because she had already blocked me beforehand. I feel ill.

The dry spell on the dating apps I'll normally use has led me to the gay ones. I am not gay, but I’ve learned that gay men are a lot easier to deal with than straight women. Hookups are very straightforward. They don’t care that I have a wife, some of them have wives too. I exclusively top, so I go for the more girly ones and pretend I’m in a woman’s ass. My dick can’t tell the difference. I’d prefer to be with women again, but I’ll take what I can get.

It was Friday night, Emma was in bed while I was taking a shower. When I finished, I sat on the toilet and scrolled through a gay hookup app until I got a message.

“Hi! You’re really handsome. I like older men.” Initially, this annoys me. I’m not old, I’m thirty-six. Before I tell this kid off, I click on his faceless profile. His name is Reuben, and his bio only mentions three things. Trans-man. Twenty-one. Basically a virgin. This piqued my interest, I’ve never been with a trans man before. The idea of it leaves me nearly salivating. Instead of ragging on him, I ask, “What does basically a virgin mean?”

He answers me quickly, "I've never been penetrated before." I love that.

As if he can read my mind, he elaborates, "I've only been with two people in my life, but I just never ended up getting that far. My ex dumped me a few months ago on my birthday. I wanted her to take my virginity but she refused to."

I offer my condolences, "I'm sorry about that. I appreciate you saving yourself for me, though."

He replies, "Funny. I planned on sleeping with my friend who's also a virgin but he keeps flaking out on me."

Let's get back on track, Reuben.

I tell him, "That's probably for the best. I'm much more experienced. I know exactly how to please you, baby."

He doesn't respond, so I get ready for bed. To my relief, Emma is already asleep when I leave our bathroom. I plug my phone in and I slide under the covers, snuggling up next to her and resting my hand on her belly.

Emma is gone when I wake up, she usually spends Saturdays with her mom. This is perfect, my entire day is cleared for Reuben. I text him and asks if he wants to call, which is met with my phone immediately ringing. I accept, when he says hello I discover that his voice is only slightly deeper than my wife's.

I laugh, "Your voice is pretty cute. What're you doing today?"

"Nothing much, I'm just gonna hang out at my apartment."

"How'd you like to get something to eat with me around noon? There's this really good Mexican place I know, I'll send you the address. We can have a little date before we hook up."

"Sure. Are you paying?"

"Obviously. Anything for you, prince."

"Cool."

We're both silent for a minute. Finally, curiosity overtakes me and I ask him, "How tight are you, baby?"

He sounds annoyed as he scoffs, "How the hell would I know? I'm a virgin. No one's been in there before."

I laugh this off, but he stays quiet. I try to prompt him a bit more, "I'm so excited to see your pretty face... When you texted me, you said I was handsome. What else do you think about me?"

I can almost hear his eyes rolling over the phone. He clicks his tongue and informs me, "You're okay, I guess. You're the only guy that answered me. I just wanna get it over with because I find being a twenty-one year old virgin a little ridiculous. I’m just trying to hopefully get drunk enough to sleep with a man and not wanna kill myself afterwards. I gotta go, send me the address.”

Ouch. I ignored how much that stung and sent him the address. Honestly, I couldn't care less how about eager he is to see me. Whether he loves me or hates me, that pussy is mine.

When Reuben arrives at the restaurant, I'm disappointed to learn that he's much more masculine than his voice led me to believe. His face is a bit chiseled, his dirty blond hair is starting to thin out, and he’s got some mutton chops and a bit of a unibrow going. I’m not going to complain, I’ve gotten with much uglier men before, but if he weren’t trans I wouldn’t look twice at this kid.

He barely spoke the entire time and he didn’t make eye contact with me once. For someone who apparently wanted to get plastered before we hooked up, he didn’t drink anything, whereas I had two large margaritas. He didn’t order much food and barely pecked at it. That’s fine, I’m just happy he didn’t ask for something expensive. When I’m done with my meal, I pay the tab, take his hand, and we leave.

Before I release his hand, I ask, “You planned on me coming to your place, right? I don’t want my wife to come home and catch us.” This finally forces Reuben to look directly at me and I notice his icy blue eyes look glazed over.

“You’re married?” He sounds disheartened by this, so I save myself with, “Yeah, it’s fine. We’re pretty open but her pregnancy is making her really emotional so I don’t want to stress her out with somebody being in the house.”

His lips part like he’s going to say something, but they squeeze shut again. He clears his throat and says, “Sure. My apartment complex is just up the road, so we can walk there.”

We walk side by side to his building, I’m swaying slightly from the drinks. Once we get in his room, I plop down on the couch and immediately put on a movie as he goes into the kitchen. He comes back with a glass of red wine in each hand and he gives me one before he sits down next to me. I take a long sip of the drink, it’s much more bitter than any wine I’ve ever tasted before, but I like the flavor. I finish the glass as the movie begins.

“If you want some more, the bottle is on the kitchen counter.”

I shake my head at his offer and I set my empty glass on the coffee table. “No, thank you. I shouldn’t drink too much, I need to drive back home tonight.”

Around twenty minutes into the movie, I’m hit with a wave of nausea. Whenever I blinked, my vision got blurrier. I forced my eyes to stay open as the misty room began to whirl around me. I touch my palm to my forehead and I discover that I’m drenched in sweat. I think Reuben asks if I’m okay, but I can barely hear him over the pounding of my heart echoing throughout my body. I slowly stand up, but my knees buckle under my weight and I crash headfirst into the coffee table.

When I find the strength to force my eyes open, I find myself sitting upright at Reuben’s kitchen table. He’s sitting in the chair closest to me, his chin resting on his interlaced fingers as he stares at me, a small smirk on his face and a chef’s knife lying in between his elbows. I try to get up but I can’t move. I look down and I see that I had been duct-taped by my chest, hips, arms, and legs to the chair he’s sat me in. I look back at him and I notice six narrow cardboard rolls on the table, pushed to the side. My mouth is dried up, but I groggily ask, “What did you do?”

 “I spiked your drink. You’ve been out for a while.” Reuben scoots his chair a bit closer to me and he stares into me, more composed than he’s been all day.

“Do you recognize me?” He looks at me with anticipation as I rake my hazed brain for where I could know this guy from. I’ve never seen this kid before in my life.

I shake my head no and he chuckles, “I knew you wouldn’t. I’ll be honest, I’m a little offended that you forgot about me. It’s been years and I’ve just never been able to get you out of my head.”

I tell him, “I think you’re looking for a different Duke Redmond. I don’t know you, man.”

He drums his fingers on the table before he asks, “Does the name Penny Flynn mean anything to you?”

My eyes nearly pop out of my head, which brings a huge smile to his face. I finally recognized him.

He reaches behind himself and picks up the knife. I plead, “Penny… I mean, Rueben, please don’t hurt me! Please let me go! You know I have a wife, I have a baby on the way, they need me!”

He snorts in amusement, “That’s cute. Your wife and baby weren’t enough to stop you from seeing me in the first place. You don’t care about them, what makes you think I will?”

Tears start to spill down my face, snot begins leaking out of my nose. I sob, “Is this because of what I did to Alice? I was drunk! I’m sorry, I made a mistake!”

His free hand shoots out and wraps around my neck as far as his fingers will let him. He snarls, “Your mistake put her in the hospital! Your mistake almost killed her! My family and I stayed with her the whole time! I see her battered face every time I close my eyes, do you know what that’s like? Do you know how horrifying that was? I was six!”

As his grip on my neck tightens, I keep mouthing 'I'm sorry’ to him. He spits, “The day I found my sister in the state you left her was the day I learned what wrath felt like. I’ve had to sit with it for my entire life and it never went away, no matter what I did! She told me you reached out to her and I was disgusted, but I knew I’d be able to get you back. Now, I’m getting the closure I need.”

He releases my neck and I gasp for air. Reuben takes the blade of the knife and he presses it into the soft skin just above my collarbone.

I steady my trembling lips enough to ask him, “Are you going to kill me?”

He puckers his lips and they veer off to one side of his face. His eyes drift along my body and the floor as he contemplates his answer. He says, “I don’t know, I haven’t decided yet. But I’ll tell you this, you are gonna know how I felt that night. All the pain, all the suffering, all of the heartache you caused my family is coming right back on you tonight. Either way, it’s gonna hurt, Duke.”

He flashes me one last smile. Looking in his cold eyes, I see some glint of contentment. I can tell that he’s made his decision. I feel the sick sting of regret.

October 04, 2024 02:51

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5 comments

Trudy Jas
22:56 Oct 10, 2024

Hey Montrell. Rueben gets his revenge and Duke his just desserts. You described the character so well that I was ready to volunteer to do his castration. LOL

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Montrell Burke
03:02 Oct 11, 2024

LOL I'm so glad you enjoyed it!

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Trudy Jas
15:01 Oct 10, 2024

Montrell, just so you know, J Foster's review is AI generated. Feel free to ignore it.

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Montrell Burke
21:30 Oct 10, 2024

Thank you for letting me know!

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Unknown User
00:44 Oct 10, 2024

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