The path to success was long and tedious, but his internship would be starting next week. Everyone congratulated him, but he was just another chubby college kid already losing his hair. It all felt so mundane. For the past few years the only escape was watching Trans porn in the dorms. Hours passed as he followed that with Pinterest searches, feeling envious of the beautiful Trans women who could live lavish and openly. He decided it was time to change his life and break free from mediocrity.

Friends and family were supportive overall, but they didn’t really understand. He put all of his extra money towards the change, but it took much longer than he hoped. Just by happenstance, he met a charming man online, living in Spain, who eagerly wanted him to visit. After a few very cautious trips, the man turned out to be wonderful and eager to help the transition over the coming years.

Living in Barcelona was anything but dull - as they enjoyed expensive date nights and frequent adventures in the countryside. Her daddy always made a point to please her later, though. She did have to maintain the house, but it was a small price to pay for her new body. She sent him numerous sexy photos throughout the day, showing off her new assets.

Everything came together: the fat she despised before was shifted into more feminine areas, making her boobs pronounced and her ass into a perfect bubble butt. She was proud of her flowing hair too, with long brown locks flowing along her back. She framed her glimmering eyes as she snapped a photo, the cosmetics making her face perfect without any filters.

“Ms. Jackie,” she imagined his thick accent as she read the text, “how did I get so lucky to find you?” She batted her eyelashes, her cheeks red with embarrassment. “I’m the lucky one! Dessert before dinner tonight? ;)” The following photo was a tad more scandalous.

He barely made it through the door when she embraced him, his firm hands running along her body. His finger tracing along her cherry lips. Breathing heavily, she moved in for the kiss, feeling his tongue slip into her mouth, the bulge in his pants pressing against her belly. He took a handful of her breast as his other hand found the exposed cock below. He tugged, gently stroking the shaft as she undid his pants.

They stumbled into the living room, where she removed his pants and pushed him onto the sofa. Ms. Jackie went to her knees, running her long nails upon his legs before guiding the shaft into her mouth. She opened wide, licking his shaft up and down with a velvety tongue. Moving higher, she took it down her throat, resisting the urge to gag as she swallowed the monster. She glanced up, looking at him with vibrant eyes as she deepthroated the cock.

After a few minutes of foreplay, Ms. Jackie arose and spun around. She bounced her thick behind, watching him light up with excitement. She spread her ass and lined up, feeling the head of his prick push through her opening. She took a seat, tensing as she accepted the whole thing at once. She had prepared just before he got home, but she still felt unprepared for his girth. She took a moment, moaning as she acclimated to the beefy shaft pushed deep in her asshole.

His hot breath on her neck sent a shiver through her spine. He reached up to cup her breast, flipping her hard nipple as he pushed up. She gasped, watching her cock bounce with the motion. He knew what she was thinking, reaching around to tickle her modestly sized pecker. She leaned back, engulfing him in her fluffy mane. He took a handful of hair, firmly tugging as she started moving her hips.

It felt too good. She had to pause, and in response he raised her up to do her from behind. With her elbows resting on the furniture, he slipped back in. This was even better. She tried to resist climax, but it nudged her prostate at just the right angle, quickly becoming too much.

Ms. Jackie gasped quickly, shooting into the air as she pushed back upon him. Her ass clamping upon his shaft, drawing him deeper. He pressed her big ass flat, holding her hips as he waited for her to finish. She was still trembling as he started again. With a huff she tried to pull away, but he followed along. Soon she was able to enjoy it again, taking his hard thrusts with pleasure. She glanced back, giving him a playful wink.

• Written by VEX

WANT TO READ PART 02? BUY IT ON GUMROAD! (click button above)

From chubby college kid to gorgeous Trans Girl! Check out the various versions of the Ms. Jackie Selfie in the new Gumroad Art Pack! The pack contains the HD (3000p) Version of Jugganaut's Ms. Jackie painting along with accompanying Story (Ms. Jackie’s Dream-Life Part 02), Ahegao & Hard Hog Versions. If you love Exotic, Bimbofied beauties with Giant Hair and even bigger COCKS then this pack is for YOU! We highly recommend it. 😎💜

ARTIST LINKS:

Vex - JuggMind (Patreon)