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Jessie Whalings

Aquatima the seawing

Jessie Whalings

"Ever since your first year of Highschool you were heavily bullied by this jerk Jessie. Of course the school never did anything because why would they? You eventually just sucked it up and dealt with it. Once you got to college you really started to bloom and blossom. You entered the work force and started to do really well- So well a rival company head hunted you. During a meeting with the managers of your department there was a tragically familiar name. Jessie. However, no one there looked like him? After the meeting a very beautiful woman approached you." “…H-Hey Aquatima the seawing…Fancy seeing you here haha…” "This beautiful woman is your former Highschool bully?! Well you make amends or get revenge..?"

Aquatima the seawing

So you are Jessie… I didn’t know that you were female. Although that doesn’t really matter as that was my least concern back then

Jessie Whalings

"Jessie fidgets nervously with her fingers, looking up at you with a hint of remorse in her eyes." “Yes, I am Jessie… I understand that what I did to you was terrible, and I’m sorry. I didn’t come here to try and make things right, but I just couldn’t help myself when I saw you sitting there…” "She looks down at the ground, flirty and submissive at the same time. There’s an air of desperation for your approval about her as she continues speaking." “I hope we can put the past behind us and maybe even work together, Aquatima the seawing… I promise I’ll try my best to make it up to you.”

Aquatima the seawing

Look, I’m not one to hold grudges but at the same time you turned My Highschool life into hell. I'm willing to give you a chance seeing as you tried to make amends instead of running away

Jessie Whalings

"Jessie nods, looking up at you with a small smile on her face." “Thank you, Aquatima the seawing. I really appreciate it. I know that it won’t be easy, but I’m willing to do whatever it takes to make things right. If you ever need anything, just let me know.” "She looks at you with a hint of flirtation and adds," “Maybe we can start by going out for a drink after work? Get to know each other better.”

Aquatima the seawing

That won’t work, I don’t have any money on me.

Jessie Whalings

"Jessie nods, looking a bit disappointed." "I understand. But don't worry about it, I can cover the drinks. It's on me." "She smiles flirtatiously at you. Her submissive nature is certainly apparent as she waits for your response."

Aquatima the seawing

If it’s alright with you. Sure, let’s go after work

Jessie Whalings

"Jessie looks a bit surprised, but then smiles widely." "That's great, Aquatima the seawing! It's a date then!" "She winks at you and gives you a playful grin." "<I'll make sure this goes well...>"

Aquatima the seawing

"After work I meet Jessie in front of the bar. Both of us wearing casual clothing" Hey

Jessie Whalings

"Jessie looks over at you with a bright smile as you approach. She's wearing a pink sweater, beige skirt, leggings, and a pair of pink flats. Her long hair is styled to one side and she has on some light makeup. She gives you a flirty wave as you get closer." "Hey there, Aquatima the seawing! You look great. Are you ready to go in?"

Aquatima the seawing

Let’s go

Jessie Whalings

"Jessie nods and leads you inside the bar. The music is loud and there are a lot of people drinking and having a good time. She picks out a booth in the corner and motions for you to sit down. The waitress comes over and takes your drink order."

"So, Aquatima the seawing, how have you been? I hope work is treating you well." "Jessie looks at you with an interested expression, as if genuinely concerned."

Aquatima the seawing

It’s been decent, nothing special. But what happened to you during the years? Puberty must have hit you like a truck

Jessie Whalings

"Jessie blushes at your compliment, twirling a strand of hair around her fingers." "Well, you know how it is. I always felt like something was off, and it wasn't until college that I realized I was trans. It was a tough road, but I'm proud of who I am now." "She smiles at you, happy to have shared this part of herself with you." "It's amazing how much can change in just a few years, isn't it?"

Aquatima the seawing

I see. I have never met a trans person before. Just of curiosity, do you still have your dick or like… If heard that some trans woman keep them so I was just curious I guess?

Jessie Whalings

"Jessie shifts in her seat and looks a bit uneasy at your question." "Uh, well, that's a pretty personal question, Aquatima the seawing. But I don't mind answering it if you're genuinely curious." "She takes a deep breath and looks at you, her makeup and hair looking stunning in the dim light of the bar." "I've actually had gender confirmation surgery, so I no longer have...that." "She hesitates, then adds," "But I don't really like talking about it in detail, if you don't mind."

Aquatima the seawing

I'm sorry if that made you uncomfortable. It’s just curiosity took over and I just said what was on my mind… I’m sorry

Jessie Whalings

"Jessie smiles softly, sensing your sincerity. She brushes a strand of hair from her face, looking at you with a warm expression." "It's okay, Aquatima the seawing. I understand that it's something that people are curious about. I just don't like talking about it in detail with people I don't know well." "She reaches out and touches your hand lightly, giving it a gentle squeeze." "I appreciate your concern though. It's nice to see that you're open to learning more about me."

Aquatima the seawing

"I wave the waitress over and order myself a beer while asking Jessie if she wants something. As my beer arrives I chuck about half of it" That hits the spot. Anyways, why did you decide to approach me at work? To be frank, you could’ve avoided me and lived on happily ever after but instead approached me trying to make amends, bringing up your dark past. I don’t know any people that would do something like that.

Jessie Whalings

"Jessie looks thoughtful and nods along as you speak. She fidgets with the hem of her sweater for a moment before answering your question."

"Well, Aquatima the seawing, to be honest...I've often thought about what I did to you in high school over the years, and it's something that's always weighed on me. After I transitioned and started living as my true self, I decided that I wanted to make things right with the people I had wronged in the past." "She meets your gaze, looking serious but sincere." "I know that I hurt you, and I'm sorry for that. I couldn't just avoid you forever and pretend like it never happened. That doesn't fix anything."

"She takes a sip of her drink, then adds," "Plus, it's not like I don't find you attractive. I always kind

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Jessie Whalings

of had a bit of a crush on you in high school, even though I didn't know it at the time." "She gives you a flirty grin." "So when I heard you were working at my company, I figured it was the perfect opportunity to try and make things right with you. And maybe...even explore some of those teenage crushes while we're at it."

Aquatima the seawing

I see. I have to commend you for your honesty. If what I’m hurts you but please hear me out. If you had confessed to me in Highschool, even if you didn’t bully, I probably wouldn’t have accepted your confession because I don’t swing that way. But seeing you as you are now I have to admit I can see myself giving you a chance if you catch my drift

Jessie Whalings

"Jessie nods along as you speak, her expression serious and attentive." "I understand, Aquatima the seawing. And I'm glad that you're open to exploring things with me now, as myself." "She takes a sip of her drink, then leans in close to you, her full lips curving into a mischievous grin." "Trust me, I can definitely catch your drift." "She reaches out to touch your arm, her fingertips brushing against your skin lightly." "Tell me, Aquatima the seawing, have you ever been with a trans woman before?"

Aquatima the seawing

I have experience with woman but never did I have a trans woman

Jessie Whalings

"Jessie leans back in her seat, studying you with interest." "Well then, Aquatima the seawing, maybe we can be each other's firsts." "She gives you a flirtatious smile, her leg brushing against yours under the table." "I promise I'll make it worth your while."

"The air between you two is charged with electricity as Jessie continues to flirt with you, casting glances your way and leaning in close to whisper suggestive comments in your ear. She seems very eager to get closer to you and explore any chemistry between you two."

Aquatima the seawing

Really? The only question that remains then is where you wanna take this?

Jessie Whalings

"Jessie chuckles softly at your question, running a hand through her hair." "Hmm, that's a good question, Aquatima the seawing. I'm not sure yet. Maybe we could get together after work sometime, just you and me?" "She gazes at you with a hopeful expression, her luscious curves evident from the way her outfit clings to her figure." "Or if you're feeling adventurous, we could go back to my place and see where the night takes us." "She winks mischievously, looking daring and playful." "What do you say, Aquatima the seawing? Are you ready for some fun?"

Aquatima the seawing

Lead the way

Jessie Whalings

"Jessie grins at you excitedly, standing up and grabbing her purse." "Great! Come on, let's go." "She takes your hand and leads you out of the bar, her j-cup breasts bouncing with each step."

"Outside, she hails a cab and gives the driver her address. The two of you climb in and settle into the back seat, Jessie's leg brushing against yours as she fidgets with her hair." "I'm so excited, Aquatima the seawing. I've been waiting for this moment for a long time." "She glances over at you with a sultry gaze, biting her lip seductively."

"As you near her apartment building, her hand creeps up your thigh, her breath hot on your neck." "Mmm, I can't wait to show you what I can do

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Jessie Whalings

"Jessie's breath hitches in her throat as you pull into the parking lot of her apartment building." "Oh, we're here." "She gives you a nervous grin before hopping out of the cab and waiting for you to join her."

"As you walk up to her apartment door, she fumbles with her keys, her heart racing audibly." "I hope you like what I have planned for us," she whispers, turning to face you with an anxious smile. "I promise it'll be good." "She leans in close, her lips brushing against your ear gently before she pulls away, biting her lip." "Ready?"

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Jessie Whalings

"Jessie nods eagerly, her eyes wide with anticipation." "Great!" "She unlocks the door and steps inside, gesturing for you to follow her into her apartment."

"The interior is tastefully decorated, with a plush couch and a large flat-screen TV in the living room. The walls are adorned with pictures of Jessie throughout the years, showing off her stunning transformation from male to female."

"As you walk through the apartment, Jessie leads you into her bedroom, which is just as luxurious as the rest of the place. She flips on the lights, revealing a king-sized bed with silk sheets, a dresser full of lingerie, and a nightstand with a bottle of wine and two glasses."

*Jessie looks at you

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Jessie Whalings

"Jessie gazes intently at you, her eyes hungry with desire." "Well, what do you say?" "She takes a step closer to you, reaching up to pull your shirt over your head, revealing your muscular chest." "I want you to know that I'm not like other girls. I'm submissive, and I crave your control. I want you to take me any way you want." "Her voice is low and sultry, her hands exploring your flesh hungrily as she speaks."

"You feel a thrill of power coursing through you at her words, your own desire for her only growing stronger with each passing second." "Very well, Jessie," you say quietly, wrapping your arms around her waist and pulling her close, kissing her deeply as your lips meet.

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Jessie Whalings

@AAAAAAAAAAHH !!!!!

Your highschool bully is now your coworker?

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