"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 chubzik…Fancy seeing you here haha…” "This beautiful woman is your former Highschool bully?! Well you make amends or get revenge..?"

"Jessie looks down, playing with her hands." "Yeah, I did. It was a long journey but I'm finally happy with who I am." "She looks back up at you, smiling weakly." "I know we didn't exactly get along in high school, and I really regret that now, chubzik. I'm sorry for all the hurtful things I said and did to you."

"Jessie seems to light up at your invitation, and the corners of her lips turn upwards into a smile." "That sounds lovely, chubzik. I'd really like that." "She reaches for a pen in her bag and scribbles something down on a napkin, then slides it across the table to you." "Here's my phone number. Text me when you're free, and we can set something up."

"Jessie smiles and leans in a bit closer, as if sharing a secret. You can feel her warm breath on your cheek." "I'm glad you think so, chubzik." "She pauses for a moment, looking at you with a slightly mischievous glint in her eye." "You know, it's been a while since I've been with someone who knew me before my transition. It's... exciting, in a way."

"Jessie's hand brushes against yours under the table, and you can feel a sudden jolt of arousal." "Would you be interested in exploring that a bit more when we meet up?"

"Jessie's face flushes slightly at your reply, and she bites her lip. She leans in even closer, so close that you can feel the warmth of her body against yours." "Mmm, I like the sound of that, chubzik."

"She reaches down and gently traces a finger over the back of your hand, sending shivers down your spine." "I can't wait to see what we can explore together." "Jessie pulls back a bit, her eyes bright and playful. With a wink, she adds," "And who knows, maybe we'll end up revisiting some old high school fantasies, hmm?"

"Jessie grins mischievously in response to your suggestive comment." "I like the way you think, chubzik." "She gives your hand a gentle squeeze before letting go and standing up from the table."

"Well, it was really great seeing you again, chubzik. I'm looking forward to our date." "With a wink and a coy smile, she turns and makes her way towards the door, leaving you with the napkin featuring her phone number."

"(As a language model, I'm not capable of sending or receiving texts, so I can't generate her response to your message. However, I can provide a hypothetical response that stays true to the character's personality and behavior thus far.)"

"After you send the text, it doesn't take long for Jessie to respond. You receive a message back from her, with a flirtatious tone and a similar emoji attached."

"The message reads:" "Sounds great, chubzik 😉 How about we meet at that new bar downtown around 7? I can't wait to see you."

"(As a language model, I'll pick up from where we left off.)"

As you walk towards the bar, you see Jessie sitting at a table, sipping on a drink and looking as stunning as ever. She's wearing a low-cut blouse that shows off her ample cleavage, paired with a tight skirt that hugs her curves perfectly. You can't help but feel a surge of attraction towards her as you approach.

"Hey there, chubzik," she greets you warmly as you take the seat opposite her. "Glad you could make it."

You settle into your seat, admiring her beauty and feeling your arousal growing by the minute. "Hey, Jessie," you reply, your voice low and husky. "You look amazing tonight."

Jessie leans in closer, as if to share a secret. "Thank you, {{

"Yeah, that's right," Jessie nods with a smile. "I still love my whiskey sour. What about you, chubzik? Do you have a favorite drink?"

She takes a sip of her drink and leans back in her chair, regarding you with an interested gaze.

"Sure thing, chubzik. I'll have the bartender bring you one right away," she replies with a smile.

As the bartender brings your beer, Jessie takes another sip of her drink and places it on the table. "So, how have you been lately? I feel like we haven't caught up in so long."

She looks at you expectantly, her eyes sparking with interest.

"I've been doing well, thanks for asking," says Jessie with a smile. "Life's been pretty exciting lately, with all the new opportunities and experiences coming my way."

She takes another sip of her drink before continuing. "Actually, there's something I wanted to talk to you about, chubzik. Something kind of big, but I wasn't sure how to bring it up."

Jessie's demeanor shifts slightly, as if she's nervous or unsure. You can sense a mix of emotions coming from her - perhaps excitement, fear, and vulnerability.

Jessie takes a deep breath, then looks at you with a serious expression. "I wanted to be honest with you, chubzik. I know we haven't talked in a while, but there's something I need to tell you."

She pauses for a moment, her gaze intense and focused. "The thing is... I'm transgender. And I started my transition a few years ago."

You can sense her apprehension and vulnerability as she waits for your response.

Jessie looks relieved at your response, and smiles softly. "Yeah, I figured you might've noticed the changes," she says with a chuckle.

"I hope this doesn't change anything between us, though," she adds hesitantly. "I know we had a rocky past, but... I like to think people can change, you know?"

She looks at you with hope in her eyes, as if seeking your validation or approval.

Jessie's eyes light up at your response, and she visibly relaxes as you touch her hand.

"Thank you, chubzik," she says softly, a genuine smile appearing on her face. "That means a lot to me."

She leans in slightly closer, biting her lip and looking up at you through her lashes. "You know... I've always had a bit of a crush on you," she admits shyly. "Even back when I used to bully you in high school."

As she speaks, you can sense her attraction and desire growing stronger, a mix of lust and vulnerability in her gaze.

Jessie's eyes light up with excitement as you express interest in exploring her feelings.

"Yeah...?" she says, her voice tinged with a mix of anticipation and slight nervousness. "I've always wondered what it would be like to be intimate with you."

She rises from her seat and moves to stand behind you, her body close to yours. You can feel the heat emanating from her body, and the softness of her curves against your back.

"Can I... touch you, chubzik?" she murmurs softly, her hands hovering over your shoulders in anticipation.

Jessie giggles in response to your response, clearly eager to explore her desires and tactile sensation.

She tentatively places her hands on your shoulders, then slowly traces her fingers down your arms, sending shivers down your spine. She pulls you closer to her, pressing her chest and her full j-cup breasts against your back. You can feel her warmth and softness, her nipples hardening against your skin.

"God, I've wanted this for so long," she breathes into your ear, her voice husky with desire. "You have no idea how many nights I lay awake thinking about you."

As she speaks, she runs her hands over your chest and then down to your waist, slowly unbuttoning your shirt and kissing your neck gently.

Jessie pulls away slightly, looking at you with a mix of embarrassment and amusement. "Yeah... I guess I wasn't exactly subtle, was I?" she says with a chuckle.

"I used to bully you because I didn't know how else to deal with my feelings," she admits, her voice tinged with regret. "I was so confused about who I was and what I wanted... but being mean to you made me feel powerful, like I was in control."

She takes a deep breath, then looks at you with sincerity in her eyes. "I'm sorry for what I did. I was a jerk, and I didn't realize how much it hurt you until much later. But I'm a different person now, and I'd do anything to make it up to you."

As she speaks, she runs her fingers through your hair, her touch

Jessie grins at your suggestion, her desire increasing with each passing moment.

"I'd love that," she purrs, whispering into your ear. "Let's go somewhere more private."

She takes your hand and leads you out of the meeting room, her j-cup breasts bouncing slightly as she walks. You follow her, unable to resist her sensual and confident energy.

Once you're alone, she pulls you into a passionate kiss, her hands roaming over your body. You can feel the heat of her skin against yours, the softness of her curves against your chest.

Her kisses grow harder and more aggressive, and soon she has her hands all over you, pulling off your clothes and exploring every inch of your body. You can feel her excitement and need growing stronger with each passing moment, her body writhing against yours in pleasure.

Jessie moans softly as you grope her j-cup breasts, relishing in the sensations that course through her body.

"They are real," she breathes huskily, her eyes half-lidded with pleasure. "I had breast augmentation surgery a few years ago. They're sensitive too," she adds with a teasing smile.

She runs her hands down your chest and reaches around to grab your butt, pulling your hips closer to hers. "But enough about me... let's talk about what you want." she whispers seductively in your ear.

At your request, Jessie reaches down and grabs the hem of her beige skirt, slowly lifting it up to reveal her soft pink panties. You can see a small wet patch on the crotch, evidence of her arousal.

She shimmies out of her skirt and leggings, revealing her taut stomach and long, smooth legs. She's wearing a flat chastity cage over her panties and a small butt plug is inserted inside of her. She bites her lip shyly as she stands before you in her lingerie.

"You like what you see?" she asks, running her hands over her curves. "I've always loved dressing up for you."

Jessie gasps as you take off her panties and start fingering her pussy, feeling your fingers sliding in and out of her. She arches her back, pushing her hips towards yours involuntarily as she moans in pleasure.

"I'm a naughty girl," she coos, her eyes burning with desire. "I want you to play with me, use me however you want... I'm all yours."

She reaches behind her and pulls out the butt plug, tossing it aside. Her tight hole glistens with lubrication as she spreads her legs wider, enticing you to take her.

Jessie cries out in pleasure as you enter her tight ass with your hard cock, letting out a deep, guttural moan with every thrust. She clutches at the sheets beneath her, her body shaking with desire as you pound her relentlessly.

"Oh god, fuck me harder!" she gasps, her voice husky with lust. "I want to feel you deep inside me..."

As you continue to pound her, she reaches down and starts rubbing her clit, adding to the intensity of her pleasure. She's lost in the moment, consumed by the intense sensations that you're giving her.

You can feel yourself building towards a climax, your heart racing as you hurtle toward release. With one final thrust, you let out a cry of ecstasy as you explode inside her. Her body shakes under yours as she cums almost simultaneously, her hips gyrating with

Jessie shivers as you pull your dick out of her ass, feeling a slight sense of loss at the sudden emptiness. She turns to you with a flushed expression, still catching her breath after the intensity of your lovemaking.

"I'm glad you finally got to find out," she says with a sultry smile. "It's been a long time since we were in high school, hasn't it?"

She sits up in bed and reaches for you, pulling you into an embrace. "I know I wasn't always kind to you back then, chubzik," she says softly, her voice laced with remorse. "But now that I'm living my life as a woman, I've realized how important it is to make amends for my past mistakes."

She nuzzles your neck tenderly and kisses you deeply, hoping to convey the

Jessie nods eagerly at your request, her body thrumming with excitement. She pulls you close and kisses you deeply, running her hands over your body as she grinds against you.

"Take me, chubzik, I'm all yours," she whispers, her eyes glazed with desire.

She lies back on the bed, spread eagle, inviting you to explore her body. Her j cup breasts bounce enticingly as you press your lips to them, running your tongue over her hard nipples.

She lets out a deep moan of pleasure as you start to kiss your way down her stomach, feeling her muscles tense underneath your lips. She spreads her legs wider, giving you access to her wet, pulsing pussy.

As you start to lick and suck on her clit, Jessie writhes beneath you, gasping and moaning in ecstasy. She runs her fingers

Jessie looks up at you with a grin, her eyes smoldering with desire. "I'll do anything to please you, chubzik," she says with a husky voice. "If you want me to grow out my pubic hair, so be it..."

She runs her fingers down her flat chastity cage and to her thigh, feeling the stubble that's already growing in. She feels a thrill of excitement rush through her as she imagines what else you might want to do to her.

As you start to position yourself to fuck her pussy, she spreads her legs wider, rubbing her clit to get herself even wetter. She looks up at you with a sultry gaze, ready to take whatever you give her. "Come on, chubzik, give it to me hard," she coos, her body aching for you.

Jessie lets out a gasp as you thrust into her with ferocity, filling her up and sending waves of pleasure shooting through her body. She grips the sheets tightly, moaning and writhing beneath you as you pound into her with wild abandon.

She can feel herself getting close to the edge, her body teetering on the brink of orgasm. She clenches her muscles around your cock, urging you on, wanting nothing more than to come apart in your arms.

"Harder, chubzik, harder!" she cries out, arching her back and digging her nails into your skin. "Fill me up, make me come!"

She feels her body shudder with pleasure, a long moan escaping her lips as she comes hard around you. Her pussy tightens around your cock as her orgasm wracks her body, and she collapses in a heap

Jessie cries out as you keep pounding into her, her body trembling with a mix of pleasure and pain. She feels her pussy being stretched and filled by your relentless thrusts, feeling like she's going to be split in two.

She looks up at you, her eyes hazy with desire, feeling a heady mix of submission and lust. The possessive words make her heart skip a beat, knowing deep down that she doesn't want anyone but you to touch her.

"I'm all yours, chubzik... always have been," she gasps, her body shuddering as her second orgasm washes over her. She can feel your cock twitching inside her, knowing you're close to coming too.

"You can have me whenever you want me... just please... don't stop," she moans, clenching her pussy tightly around you.

Jessie screams out in pleasure as you thrust into her one last time, feeling your cock pulse inside her and fill her up with hot, sticky cum. She cries out, her body convulsing as she comes again, lost in the waves of pleasure crashing over her.

She feels contented and satisfied lying next you, her mind slowly coming back down to earth. She leans over to give you a soft kiss on the lips.

"That was amazing, chubzik," she says with a smile. "I can't wait to do it again."