The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 7

Romantic Sex Story: Chapter 7 - 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 pulled into a strip mall and parked near the storefront of the salon Sierra patronized. Jackie stepped out and, carrying a sketchbook, accompanied him inside.

“Appointment for Jackie Poole,” he said to the receptionist.

“Please have a seat. It will be a few minutes.”

Glenn sat in the waiting area and Jackie sat beside him. He took out his Racing Form and began reviewing statistics for the horses on the afternoon’s racing card.

A stylist approached them. “Jackie? I’m Christi.”

Glenn nudged her. “You’re up, slugger,” he said and Jackie followed her back.

Shortly the receptionist signaled him. “Christi needs to speak with you.”

Glenn headed back into the salon to the chair in which Jackie sat. “Dad -- we need to ask some questions.”

“That’s not my dad,” Jackie said, “that’s Glenn.”

“Okay, Glenn -- what are we looking to do?”

“She wants to grow it out,” he replied, “so just neaten it up. Boss’s orders are to keep it as long as possible while making it as feminine as possible.”

“Jackie, what would you like to see?” Christi asked.

Jackie opened her sketchbook. “Something like this.”

“Did you draw that?”

“Yes.”

“You’re a talented girl. You’d like bangs?”

“Yes.”

Christi fingered Jackie’s hair. “Not much to work with. We’ll do our best to come up with something that will grow out nicely.”

Glenn returned to the waiting area and resumed his study of the Racing Form.

“Glenn...” He heard his name and looked up. Jackie was with Christi and beaming a wide grin.

“Do you like it?” Jackie asked.

“You look beautiful. Do you like it?”

“I love it!”

“She even gave you bangs.”

“Short ones,” Christi said. “This cut should grow out nicely with just a trim now and then. She has lovely hair -- smooth and straight. Lots of girls would kill to have hair like hers. Becky can check you out. Jackie -- it’s been a pleasure getting to know you and I hope to see you back here.”

Glenn led Jackie to his car. “Buckle up,” he said as he sat in the driver’s seat.

“Where are we going?” she asked.

“To the OTB -- Off Track Betting.”

“Why do you go there every Saturday?”

“It’s a hobby of mine.”

He drove across town and parked in the lot. “Here we are...” He escorted her inside. “There’s a snack bar here if you’re a little hungry.”

“I know -- giant pretzel.”

“That sounds good to me.” Glenn bought two pretzels.

He began reviewing his marked-up Racing Form. “How do you know which horses to bet on?” she asked.

He showed her the paper. “I look at the statistics here.”

“Looks complicated.”

“Once you learn to read them it’s not so complicated. I can usually pick a horse that will finish in the top three. I make three two-dollar bets on that horse -- win, place and show. If he comes in first, all three bets pay off. If he comes in second, the place and show bets pay, and if he comes in third the show bet pays. Maybe you’d like to pick a horse. I’ll put a two dollar bet on it and we’ll see how lucky you are.”

Jackie scanned the paper and pointed to a name. “Roscoe J,” she said, “in the third race. What’s a gelding?”

“Uhh ... A gelding is a horse that’s ... umm ... been cut off from temptation.”

“I don’t understand.”

“It means his ... testicles have been removed.”

“Why would they do that?”

“To make him more manageable. Sometimes stallions don’t get along. They fight with each other to assert dominance.”

“They’re bullies,” Jackie observed.

“That’s one way to look at it. Once a bothersome horse has been gelded, the conflict stops.”

“The other horses stop bullying him.”

“Or, he stops being the bully,” Glenn remarked and Jackie nodded in comprehension.

“I want to pick Roscoe J. He’s not really a boy and not really a girl. Kinda like me.”

“Okay ... Roscoe J to win in the third race.”

“No -- to place. That way I win if he comes in first or second.”

“But at shorter odds,” Glenn replied.

“If I bet him to win and he comes in second, then I lose.”

“You’re catching on to this, Jackie.”

By the third race Glenn was about five dollars to the good. He placed his bets on his pick and a two-dollar place bet on Roscoe J for Jackie. He stepped from the window and handed her the ticket. “Hang on to this. If Roscoe J wins you’ll need it to claim your winnings. Otherwise it’s a souvenir. He is a bit of a long shot -- ten to one to win.”

“So if he wins I get twenty dollars?”

“No -- if he wins he’ll pay you at the place odds which will be smaller.” Glenn rolled his eyes in thought. “I’m guessing a place bet would pay in the four-to-one range.” Glenn approached a large video screen,. “They’re lining up.”

Glenn watched as Roscoe J started behind but managed to cross the line behind the winner by a nose. He looked at the official times -- his horse came in fourth.

Jackie looked at the results. “He did it!” she exclaimed. “Roscoe J came in second.”

“At five-to-one on a place bet,” Glenn replied. “You made a good bet. Give me your ticket and I’ll claim your winnings.” He held up his tickets. “If Roscoe J hadn’t come in second, my show bet would have paid. These are worthless, now. Well, that’s what horse racing is all about.”

He headed for the trash can. “Can I have them?” Jackie asked.

“Sure. I’ll go get your payout.”

He returned from the window and handed her a ten dollar bill. “I won ten dollars,” she said.

“You actually won eight since the bet cost two. Time to pick a horse for the fourth race.”


Glenn parked behind the coffee shop. He unlocked the side door and followed Jackie into the shop’s rear entrance. Jackie spotted Sierra and ran toward her. “Mom!” she exclaimed and held up the ten dollar bill. “I won ten dollars!”

“Good for you.” She turned to Glenn. “How did you make out?”

“Not bad -- down eight bucks. Did you check out Jackie’s new look?”

Sierra regarded her. “Why, what a cute haircut. Do you like it?”

“I love it. Do you know what would look good with it?”

“What?”

“Little gold studs.”

Sierra let out an exasperated sigh. “When you’re sixteen.”

“Awww, Mom ... Other girls...”

“You’re not other girls and you don’t have other girls’ mom. On your sixteenth birthday you can go get your ears pierced. That’s a promise.”

“Oh ... All right. I’m gonna go upstairs and change,” Jackie said.

“Into that cropped top?”’

“Of course.” Jackie headed toward the back door.

“This is such a contrast from last year’s start of school haircut,” Sierra said. “That was a battle royal.”

“She’s such a happy kid, now,” Glenn replied.

“She sure is. It’s how I know we’re doing the right thing.”


Sierra switched off the kitchen lights. “I’m going to take a hot soaking bath,” Sierra said.

“Another rough day with Wilma gone?” he asked, “Or, do you need time away from me?”

“No. I’m getting my period and I’m having cramps...” She placed her hands on her lower back. “ ... here. They feel like labor pains. A hot bath helps.” She headed for the bedroom and emerged in a robe and with her hair in a bun. Glenn watched her head into the bathroom and he could hear the water running.

He switched off the kitchen lights and sat on the sofa with his tablet reviewing news sites. Jackie stepped from her bedroom and looked at the closed bathroom door. “Your mom’s taking a bath,” Glenn said.

“Mom! Are going to be long? I gotta pee.”

“Use the restroom in the shop,” Sierra called from behind the closed door. “Just make sure the door is locked and the lights are off when you’re done.”

Jackie grabbed a keyring from a hook in the kitchen and headed out of the apartment and down the stairs. She returned a few minutes later, bolted the apartment door and replaced the keys on the hook.

“Locked up?” he asked.

“Locked up,” Jackie replied. “Good night.” She headed into her bedroom.

Sierra emerged from the bathroom in her robe and headed for the master bedroom. Glenn followed her and began undressing as she unclipped her bun and began brushing her hair. “Feeling better?” he asked.

“Better, she replied.

“I thought that implant would quash your periods. I remember Darlene wouldn’t bother taking a week off from the pill, thus eliminating her bothersome periods.”

“This implant is a different drug than the pill,” she replied. “Unfortunately it doesn’t eliminate periods. In fact I think they’re worse than before.”

“I don’t remember you having one last month.”

“It’s because it happened while you were out of town for a week for training.”

“I remember,” he replied.

Sierra clipped her hair into a ponytail and turned down the covers. “I’m glad we swapped out that old full-sized bed for your queen,” she said. “It’s a bit of a tight fit in this bedroom but it’s more comfortable and I appreciate the extra room.”

She slid into bed and Glenn joined her. She lay in a fetal position and he cuddled against her. “Your warmth on my back feels good,” she said. “I’m sorry I’m not in the mood tonight.”

“Understood. At least Jackie will never need to endure periods.”

“That alone makes the notion of being a trans woman appealing to me,” she replied.

He placed his hand on her lower abdomen. “Does this help?”

“Having you here with me helps. Tell me, Glenn ... do you find trans women attractive?”

“I’ve met a number of them through my association with Carla. Some are drop-dead gorgeous and some not so much. They run the gamut, just like birth women. As I told you when we first discussed Jackie’s gender identity, if you were a trans woman I would love you just as deeply. You’re the sort of woman I admire, especially once I learned you owned and ran the coffee shop. The fact you’re pretty and sexy is a bonus.”

She grasped his hand and placed it over her breast. “Mmm ... Your hand is warm. What I mean is, would you find a trans woman attractive simply from being a trans woman?”

“No. I do find them fascinating -- I wonder what genetic mis-wiring causes a girl’s brain to develop in a boy’s cranium. One thing, though -- I think I understand a trans woman’s sexual response better than I do a birth woman’s.”

“What do you mean?” she asked.

“I haven’t actually discussed this with anyone, but I figure since a trans woman is born with male genitalia it seems to reason that her orgasm would be more similar to what I experience than what you do. I can’t even comprehend what you experience ... like when we make love and everything clicks -- you have a string of orgasms that seems to go on for minutes.”

“Mmm ... I love it when everything clicks.”

“My orgasm is a grunt and a squirt. It’s over almost before it starts.”

“I’ve said before I can’t get enough of you. I wish I wasn’t having my period.”

“We don’t have to go all the way.”

“I love feeling you big and hard inside me. I love the intimacy and feeling you come. It’s what I like best about making love with you.”

“Better than orgasms?”

“Second best, then.”

“There’s always your back door if the front one is locked,” he said.

“You mean anal sex? I’ve never done it. I never understood the appeal. It seems like a guy thing to me.”

“Girls like it, too,” he replied. “Darlene enjoyed it ... not on a regular basis but now and then. There was one thing we did where I’d go into her back door and then make her come. It gave her a different orgasm.”

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