Transgendered gay stories: Deep in California. Author: JtellerMT. The story is including: Fiction, Anal, Blowjob, Cum Swallowing, Erotica, Extreme, Gay, Hardcore, Transgendered, Transsexual, Transvestite genres.
Transgendered gay stories: Deep in California – Part 1
Author: JtellerMT
This is a continuation of “The Transformation Jesse”, but you do not need to read the first story to understand this one. I tried to write an erotic story with detailed sex scenes. Some parts are tailored to my own interests, so I hope you enjoy.
Jesse’s new persona had taken full control of “her” life. Her lustrous encounter with Jake had changed her life forever and she loved the new experiences that came with her new lifestyle.
She had grown her long, dirty blonde hair out and started dressing as a fulltime woman. Knowing that the people that had once known her as “Jesse” would not understand or accept her recent transformation, it was time for her to leave town and start a new chapter in a new city.
She dropped out of school and moved to sunny, southern California where she acquired a tiny apartment not too far from the beach. She had thrown out all of her “manly” apparel and filled her closet with cute outfits she was more used to taking off than putting on. Starting a new in a different city was not a cheap endeavor and Jessica soon found herself running low on money. She had worked in a restaurant in her previous town, so she figured she would use her current skill set to try and land a job.
Jessica hopped in the shower and began to clean herself up for her job hunt. She washed her long, shoulder length hair, and lathered her slender body in body wash. She picked up her razor and drew the blades up her tan legs over her supple skin. The way the razor felt as it glided over her legs up towards her center, sent shivers down her spine, moistening her insides. She had begun getting herself waxed, and now that she had shaved her legs, all of her sexual entities were hairless.
With her body now clean and smooth, Jessica hopped from the shower and did a once over in the mirror. She puckered her lips and kissed her reflection.
“Big blue eyes, Check”
“Perfect perky lips, Check”
“Perfect perky tits, Not Check” she giggled
“Slender tummy, Check”
“Tight perky ass, Check” she smirked as she twisted around and gazed upon her bottom.
She lightly ran her fingertips over her groin trailing the strip of hair she had left above her prick. Her fingers ran down over her tip and caressed her hairless balls. She couldn’t help but think of Jake. The way he had made love to her on that beautiful day and made her feel like more than just a woman, but a sex goddess.
Unfortunately, Jake’s desires were similar to Jessica’s and had only recently been fulfilled. Turns out that Jake had a girlfriend which he was not willing to leave. Nor was he willing to admit to himself, or to Jessica, that what they had created was magical. Jessica took her heartbreak and turned it to motivation, which allowed her to make this change in her life permanent and fulfill her desires.
Coming back to reality, Jessica continued her self-inspection. She knew that the restaurant business was a sexist one and in order to land a job all she’d have to do is look good. She went through her closet and decided on a pair of daisy duke cut-off shorts and white blouse.
Although rather unprofessional, she knew it would turn heads even in southern California. She picked a cute black lace thong from her drawer and stepped into them. It still made her heart race each time she pulled a pair of panties up her long legs to snuggle tightly between her cheeks. Jessica had become rather good at hiding her manly package while in public. A pair of tight jeans proved not only to keep her prick well hidden, but complimented her sleek figure, making her more confident with each outing.
Jessica completed her outfit with a black bra beneath her white blouse which slightly showed through the sheen fabric. She still sported her fake implants, but had upgraded to finer ones that provided a more “realistic” look and feel.
With her hair in a side-swooping braid running over her chest, Jessica stood in front of the mirror for one more look.
“Damn, and just when I thought I couldn’t look any hotter” she said to herself.
Grabbing her purse, Jessica headed for the door. As she left her apartment she turned to lock her door dropping her keys on the floor. She turned to pick them up, catching the glimpse of one of her neighbors. Even in a quick glimpse she could see that he was a good looking man. Wanting to test herself, she locked her knees and bent over, straight-legged, to grab her keys. As her hands moved down towards the keys her shorts rose up, grasping tightly to her buttocks, and exposing her long tan legs even more.
From behind her she heard the stranger mumble under his breath, “Fuck me”.
Jessica grinned and knew that she had him looking. She popped up and turned around giving a sultry look in his direction. But, when she gazed over she realized that it wasn’t her that promoted his response. His cute blonde girlfriend had opened the door to the apartment wearing, if you can believe it, even tinier shorts. The young girl noticed Jessica’s gaze and quickly gave her a look as if to say, “Stay the fuck away from my man!”
Embarrassed, Jessica quickly locked her door and turned to head for the elevators. As she turned, she glanced up to see this man following his girlfriend into her apartment. As his girlfriend turned her back, he looked at Jessica and quickly gave her a wink.
“He WAS looking at me!!” Jessica thought as she stepped into the elevator.
With her confidence high and the sun shining, Jessica hit the streets. She came upon a night club not far from her apartment. “Le Vista” was the name and it looked rather fancy. She stepped inside and asked the hostess if they were hiring. The girl gave her a once over and in a rather nasty tone, said:
“Ummm, we’re not looking for any help, soooooo, yeah”. Chomping on her gum obnoxiously loud.
“What of bitch” Jessica thought to herself.
As she turned to leave Jessica heard a voice from behind her.
“Wait! Kim, spit that fucking gum out and learn some manners!”
Jessica turned to see a man. He looked to be in his late 30’s with his tan, wrinkling skin and slightly graying hair. His broad shoulders and weathered face made Jake look like a little boy. The tall, dark stranger emerged from the doorway and walked up to Jessica.
“Sorry about that, girls can be evil sometimes” he said, reaching his hand towards Jessica
“I’m Tom, this is my place” He said extending his hand. Jessica reached up and shook it. His grip was firm, yet comforting. The skin on his palm was rough against Jessica’s much softer hand. She imagined his fingers gripping her bottom and pulling her in tight to his chest where she could bask in his musky scent. This was a common day dream that Jessica had when she met a good looking man.
“Are you looking for a job?” he asked
“Yes, I’m Jessica” she replied, giving his firm hand a girly shake.
“Well Jessica, come with me, let’s see what we can do for ya” he said walking away.
Jessica followed him into the restaurant, smirking at the hostess as she walked by. Tom led her back to his office and closed the door behind them.
“So, how much experience do you have Jessica?” he asked.
“Not much, just a little bit in my old town” she replied.
“Well ya know, this is a pretty cut-throat town, gotta be able to bring something to that table if you’re gonna get work around these parts” he smugly replied as he adjusted himself.
Jessica knew exactly where this was going and her heart started racing. Playing along she stood up and slowly strolled around his office, admiring the items hanging from his walls. She stopped and pretended to admire a painting on his wall, bringing her legs together and arching her back, ever so slightly, to perk her ass out in his direction.
“Good looks will only get you so far honey, gotta be willing to use them if you wanna get by in this town” Tom said to her with a chuckle.
Jessica turned around and looked Tom in the eyes.
“Well….you tell me, what’s a girl gotta do to get a job?” she said in the most innocent voice she could muster.
Tom started laughing. “Hahahaha, I like you Jessica. You got spunk!”
“I want YOUR spunk” Jessica muttered with a devilish grin.
“What’s that?” He asked.
“Oh, nothing” She quickly responded
“I’ll give you chance, just be ready to bring your A-game. It’s a competition around here and the girls don’t always play fair” Tom replied.
“So when can I start?” Jessica asked.
“Come by Friday and we’ll get you all set up. We provide the uniforms so just bring that same attitude and we’ll get ya started.” Tom said.
Excited that she had just landed her first job as a girl, Jessica got over excited and squealed as she jumped into Tom’s arms as he extended his hand for shake.
Purely out of reflex, Tom’s hands grabbed Jessica’s body and conveniently ended up of her perky bottom. Even though it was only for a quick moment, Jessica savored the feel of his firm grip on her ass.
They both released themselves from each other and exchanged guilty smiles.
“I’ll see ya Friday! Thanks Tom, I won’t let you down!” Jessica said as she quickly left his office.
Unbeknown to Tom, Jessica was only so eager to leave his office because of her sudden arousal. Tom’s grip had sent blood rushing through her body and it didn’t go to her brain. She awkwardly covered her tiny bulge as she made her way out of the restaurant and past the bitchy hostess.
With her endorphins still pumping, Jessica reached her apartment and quickly stripped off her clothes. Her interview had gotten her all worked up and she needed something inside her. As she peeled the lace panties from between her cheeks the black fabric drug across her opening, sending shivers down her spine. She ran her middle finger over her ass and across her hairless taint. Bringing her finger to her nose, she inhaled deeply, basking in the scent of her smooth underside. The smell of her sweaty bulge mixed with the aroma of her feminine body wash permeated her nostrils.
With her heart pumping, Jessica ran to her dresser and pulled her special toy from its hiding spot. The dildo, that had once brought Jake to her door step and been the source of so many good nights, rose from the drawer.
Climbing onto her bed, Jessica couldn’t help but to imagine she was with Jake.
She pulled the toy to her mouth and engulfed it with her succulent lips. She worked it the same way she had once done Jake’s cock. Lathered in her saliva, Jessica positioned the toy behind her. She perked her ass up high and lowered her hips onto the slick, wet toy.
As the tip worked the outer ring of her asshole, her body relaxed. The bulbous head eased past her opening, allowing for the rest to glide inside her velvety womb.
The warmth of the sun fell upon her body as she moved up and down. She worked her hips, driving the toy to the hilt, deep inside her ass. Jessica moaned as it massaged her insides. Clenching her cheeks and arching her back, Jessica’s motions sped up. With the tip of her veiny toy now working her manly G-spot, Jessica’s body began to convulse.
Thoughts of Jake’s cock exploding inside her brought her sweet body to orgasm. With her hairless prick flopping up and down and her balls smacking the sticky shaft of her toy, Jessica’s body released. Hot ropes of cum jetted from her tip, covering her sheets and slinging up onto her bare chest.
She collapsed onto her bed as the toy slipped out from inside her. Her gaping hole pulsated as she ran her fingertips over her body, rubbing the cum into her skin.
In this time of ecstasy, Jessica’s mind fixated on her night with Jake.
“I need to feel that again” Jessica thought to herself.
She dragged her finger over her stomach, gathering any cum that had been left behind. She brought her creamy finger to her lips and twirled it inside her mouth. The salty, tangy flavors rolled over her taste buds and down her throat.
“Why do I love this stuff so much?” she asked herself as she quietly giggled.
The days came and went as Jessica prepped herself for her first day at work. She was nervous, but excited. She had never worked in such a large city let alone as a woman.
When she woke on Friday morning, Jessica was as excited as a child on Christmas morning. She spent all day making herself look good. She shaved and waxed, exfoliated and moisturized, dressed and undressed. She finally got the look she wanted and headed out for her first night of work.
She arrived at Le Vista earlier that Tom had told her to be there. The staff was already there getting things ready for the night. She heard a voice from behind her.
“Can I help you?” they said
Jessica turned around to see her neighbor from down the hall
“Don’t I know you?” the girl asked
“Oh, hey. I’m Jessica, I’m your neighbor” Jessica said with a smile as she extended her hand.
“Oh yeah.” The girl said as she extended her hand apprehensively and gave Jessica a hand shake.
“I’m Candice” she said. “What are you doing here?”
“Oh, Tom hired me” Jessica replied.
Surprised, but still polite, Candice said, “Oh nice. Let me take you back and we’ll get you all set up”
Jessica felt relieved that Candice was being polite given their earlier run-in.
She followed Candice to the back and was run through the processes. She was given her outfit which instantly made her nervous. It was a rather short, form fitting, polyester skirt and sheer white blouse. There wouldn’t be much concealment if she was to bend over or get remotely aroused, but she swallowed hard and took it excitedly.
Candice was very polite as she walked Jessica around introducing her to the other staff and telling her about the nightly routines. After the tour and crash course Jessica was sent to the back to get changed.
She slipped into her new work clothes and observed herself in the mirror. The skirt barely covered the cusp of her bottom, but it did make her assets look very appealing. She was happy that she wore tight undies tonight to help keep her package in place. The white blouse that completed her outfit was beautiful and the sheer fabric allowed her black lace bra to show through, just as she liked.
“Well this should help with the tips” Jessica thought to herself, trying to calm her nerves.
As she walked from the back room, Jessica ran into Tom.
“Oh wow!” Tom said as he saw her
“You’re gonna be raking in the dough tonight girly” He continued.
“Thank you sir” Jessica replied.
“Are you ready?” he asked
“A but nervous, but I’m ready” She said
“Well follow Candice til you get the hang of things and just remember to smile” He quickly said as he walked away
It wasn’t long before the night was in full swing and the place was packed with patrons. Jessica was doing great. Her customers were giving great tips; the guys were all flirting with her and her confidence was soaring. She was having the time of her life and getting paid for it.
As Jessica gathered drinks at the bar Candice came to her.
“Jess?” she asked
“Yeah?”
“Can you do me a HUGE favor?” Candice continued. “I have a guy in the VIP section and he specifically asked that you help serve his table. He’s a huge spender and if you can help, I think we could both make a lot”
“He asked for me!?” Jessica asked rather surprised.
“Yeah, he’s been known to get a little frisky with the servers, but if you can handle it, we’ll both make out good on this ticket” She said
“Of course!” Jessica replied, “I can hold my own” she said with a grin.
Nervous and surprised that the man asked for her, Jessica was excited to see who he was. She gathered the drinks, which of course were whole bottles, and headed to the VIP table.
Like a slow motion scene out of a movie, Jessica topped the stairs and scanned the table in the VIP section to try and find the man that had asked for her. Her eyes instantly caught the gaze of a gorgeous man. He looked to be in his mid thirties. He had broad shoulders and short dark hair. He had a little bit of stubble on his face covering a defined jaw line. His bright blue eyes followed her as she neared the table.
She nervously looked to him and then at the floor as she placed the bottles in front of him and his guests.
Jessica stood at the side of the table as Candice asked the group if there was anything else they needed. She could see from the corner of her eye that this handsome man had not taken his eyes off of her.
“What is your name my dear?” He finally spoke.