The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 8

Romantic Sex Story: Chapter 8 - A DIFFERENT KIND OF TRANSGENDER STORY: Software engineer and widower Glenn dates coffee shop owner and single mom Sierra. He meets her 11 year old boy Jack who likes fashion and wearing girls' clothes. Sierra fears he's gay but Glenn, whose cousin is TG, thinks Jack may be transgender. They have him tested and he starts reassignment therapy. This story follows the transition of 11 year old Jack into 18 year old Jackie. Along the way Sierra realizes Glenn may be the man she's been searching for.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   TransGender   Fiction   Anal Sex   Oral Sex   Safe Sex   Sex Toys  

Glenn parked behind the shop and approached the side door. He pressed the button for Apartment A using the long-short-long code he had arranged to identify himself. The door remained locked. He rang again and then rang the shop. With a buzz and a snap the door unlocked.

He entered the shop through the back door and saw Sierra at the register. “Did Jackie come home from school?” he asked.

“Yes -- she’s in the office. She had to set up some software for class.”

Glenn stepped into the office and saw Jackie sitting at the desk wearing a skirt and sleeveless blouse. “Hi, Glenn,” she said.

“How was your first day of school?” he asked.

“Good. Real good. I had to set up for our online classroom system. It’s how we submit homework.”

“Okay. What about kids who don’t have access to a computer?”

“They have computer labs we can use.” She returned to the display and keyboard. “Glenn?”

“What?”

“What did Doctor Langley say I have? Gender something starting with D.”

“Gender dysphoria,” he replied, “D Y S P H...”

“I got it. I’m looking it up on line.”

“I’ll go talk with your mom. Remember if you have computer questions, I’m here to help. It is my profession.”

He approached Sierra. “Jackie seems to be doing well.”

Sierra handed him a packet of papers. “For tonight’s parents’ orientation. We’ll need to leave right after dinner.”

“What is dinner?” he asked

“I have a stew in the slow cooker upstairs. Can you go up and give it a stir? Also give it a taste test? See if it needs salt or pepper.”

“Got it, boss.”

“Jackie and I will be up as soon as my relief shows up. She said she has some homework to do.”

Glenn headed up to the apartment and unlocked the door. He went to the kitchen and lifted the lid on the slow cooker. Smells good, he thought. With a spoon he sampled some and nodded in approval. Then, he put some flour in a bowl along with some salt and baking powder. Into this he splashed enough milk to make a thick batter and spooned it over the stew. He replaced the lid and sat in the living room with his tablet.

The door opened and Sierra stepped in. “Jackie will be up as soon as she finishes her assignment.” She headed into the kitchen. “Glenn! What happened to the stew?”

“Dumplings,” he replied. “I love dumplings with stew. It’s just some biscuit dough steaming on top.”

Jackie came in. “Homework done?” Sierra asked.

“Yes, Mom.”

“Computer turned off?”

“Yes.”

“Wash your hands and come for dinner. We’re on a schedule tonight.”

Jackie sat at the kitchen table and Sierra set a bowl before her. She poked at her dinner with a fork. “What are these white things?”

“Dumplings,” her mom replied, “Glenn made them.”

“To soak up the gravy,” Glenn added.

Jackie took a bite. “These dumplings are awesome!” she exclaimed.

“What about the stew?” Sierra asked.

“It’s real good, Mom. But the dumplings make it.”

Dinner finished, Sierra emptied the leftover stew into a deli container and put it in the refrigerator. “Jackie, can you finish cleaning up and start the dishwasher? Glenn and I need to go to your school to meet your teachers.”

“Yes, Mom.”

Glenn escorted Sierra to the parking lot. He sat in the driver’s seat and started the engine. “I can’t believe how she raved over those dumplings,” she said, “as if my stew was chopped liver. I’m sure it’s because you made them. She’s head-over-heels for you, Glenn.”

“I’m head-over-heels for both of you. I hope you’re not jealous.”

“I am, a little. You know, back when Jackie was Jack I was desperate to find someone who could be a father figure for him. When he started getting interested in girlie things I was sure it was because he lacked a man in his life.”

“I’m not sure that would have made a difference,” Glenn replied.

“I agree ... now. I do think a father figure is a good thing for a girl, too.”

“Girls need a father figure -- someone to spoil them rotten. It teaches them to be proper wives.”

“Very funny.”

“I could never say no to Darlene,” he replied, “unless it was something I was unable to do. Then I felt guilty as hell for not being able to.”

“You haven’t said no to Jackie.”

“I haven’t really had to, yet. I admire the way you deal with her. You’re firm but reasonable. You set limits, like with that cropped top she likes to wear. It’s something I need to learn to do if I’m going to be in her life.”

She reached for his hand. “You’re a real decent guy, Glenn. You are good for her.”

Glenn parked in the lot of a sprawling two-story structure. Holding hands he and Sierra headed inside. She consulted a sheet of paper. “Mrs Lipke is her home room teacher,” she remarked. “First floor -- near the office.”

They located the room and stepped inside. A stocky woman who appeared to be a few years older than Sierra was speaking with a couple.

Glenn headed for a table with stacks of papers. “Drug policy, permission slips,” he remarked. “I think we already have copies of most of these. I wonder how much paper a place like this wastes in a year.”

The woman approached them. “Hello. I’m Irene Lipke.”

“I’m Glenn Reston and this is Sierra Poole.”

“I’m Jackie’s mom,” Sierra added.

“Pleased to meet you. This is one of the home rooms for our special needs students.”

“I know the school classified Jackie as special needs. Other than being transgender, she really doesn’t have any special needs. She’s bright and a good learner...”

“Special needs doesn’t imply learning disabled,” Mrs Lipke replied. “Classifying her as such permits us to excuse her from phys ed, for example. Sixth grade is when they start wearing gym uniforms and changing in locker rooms.”

“That wouldn’t be good,” Glenn remarked.

“We have students that require medication. I’m also a licensed nurse and can dispense meds as needed. We have a boy with epilepsy who requires medication throughout the day.”

“But, wouldn’t she be better off mingling with the others?” Sierra asked.

“The special needs home rooms are smaller,” Lipke replied, “ten to fifteen kids. The regular ones are twenty-five to thirty. I’ve looked over Jackie’s transcript from Liden Elementary. She made the boy to girl change over the summer, I presume.”

“Yes.” Sierra replied. “Dr Langley prescribed a puberty blocker.”

“Middle school is a big change for all students. It’s a new routine for them -- changing classes and all, plus the fact that Clinton Middle is so much larger than the four elementary schools in the district. We have over nine hundred students in three grades here. Add to that the fact that Jackie is still adjusting to a new gender identity. We have had a few transgender students in the past and we think a more intimate home room helps them adjust. I want Jackie to know that she can come to me with issues and that this is a safe place for her. I don’t teach any classes so I’m always available.”

“That sounds very accommodating,” Glenn remarked.

“We’ll re-evaluate her after the first semester,” Mrs Lipke continued, “if all goes well and if she desires it, we can discuss moving her to one of the regular home rooms. She will be taking classes with the regular students. Based on her grades I believe she was put in the accelerated group.”

“Seems reasonable to me,” Glenn remarked. “I am impressed with how accommodating you are toward someone like her.”

“Our goal is a successful experience for all our students. Jackie is a delightful girl. I’m sure we’ll get along just fine. Do you have any other concerns?”

“I am nervous about Jackie mixing with other students from Liden Elementary who knew her as Jack,” Sierra replied. “We considered enrolling her in another district but the logistics were something we couldn’t manage.”

“We are sensitive to that. There are no others from Liden in this home room. She was placed in a section in which she is the only Liden alumnus, and all her teachers have been apprised of her situation. Some mingling is inevitable but we try to minimize it.”

“That’s a comfort,” Sierra replied.

“We should see her other teachers.” Glenn remarked. “We’re already into the next time slot.”


Glenn parked behind the shop and rang their apartment bell -- no reply. He rang the shop, again no reply. Digging his keys out of his pocket he unlocked the side door and headed up the stairs to the apartment and let himself in.

“Jackie?” he called and noticed the ladder to the attic was extended. He climbed it and saw her rummaging through boxes. “Jackie -- what are you looking for?”

“Call me Jackson -- it’s my name. I’m looking for the box of clothes Mom took out of my closet to go to Goodwill.” She opened a box, removed a tee shirt and pair of jeans and headed down the ladder and into the second bedroom...

Glenn followed and Jackson emerged wearing the tee and jeans. He could see distress on her face and her eyes were red from crying. “Something must have happened at school,” he said.

“Something happened all right. Two boys from my old school pushed me into the boys’ room. One put his hand up my dress and grabbed my...” Tears flowed down her face. “I don’t want to be a girl any more. I want Dr Langley to take out the implant.”

“You wait right here.”

Glenn bounded down the stairs and into the shop. He saw Sierra standing by the cash register. “Sierra,” he said. “We need you upstairs.”

“Glenn -- we have customers.”

“This is important.”

She looked around. “Rhonda -- can you watch the register? James should be here for his shift any time now.”

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