The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 1

Romantic Sex Story: Chapter 1 - 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 sat at a table in the coffee shop reviewing the local edition of the Daily Racing Form. With a pencil he circled horses in the various races that interested him.

“Refill, Glenn?”

He looked up at one of the baristas. “Sure, Sierra. Thanks.” Sierra appeared to be in her early thirties, tall and slender. She had a long oblong face with a strong chin, a straight nose, wide mouth with thin lips, a high and broad forehead and gray eyes. Her medium brown hair was up in a tight bun and she wore black framed eyeglasses that gave her a school-

marm look.

“How about another pastry?”

“Oh, no thanks. I’m good.”

She carried his empty mug to the counter and brewed a French Roast refill. “I see you in here every weekend with the paper and pencil,” she said as she set the mug and his check on the table. “What are you up to?”

“I’m picking horses for today’s races,” he replied. “When it gets to be post time for the first race I’ll head over to the OTB.”

“Off-track betting? You gamble on horses?” She sat across the table from him.

“It’s a hobby of mine. I have a bit of a system. I’ll pick one horse in each race and bet across the board...”

“What does that mean?” she asked.

“I’ll place bets on first, place and show. I limit myself to two dollar bets, so that amounts to six bucks a race. If there are ten races on the card, it’s only sixty bucks.”

“Why three bets?”

“If my horse comes in first, all three pay off -- different odds, but all three pay. If he comes in second, then the place and show bets pay, and if he comes in third the show bet pays -- hopefully enough to offset all three bets. I’m a good enough judge of horses that most of the time I can pick one who’ll come in the top three. Then, if I’m ahead by the last race, I’ll put half my winnings on the longest long shot. It’s free money by then. If he wins, I hit the jackpot. Otherwise I’m still walking away with more than I came with. Worst case, I’m out sixty bucks.”

“How often does that happen?” she asked.

“Not often but it happens.”

“How do you pick horses without seeing them?”

He held up the paper. “The Racing Form publishes statistics on all the horses entered in today’s races. I compare them, pick a couple for each race and then look at the odds when I get there.”

“You have to be single,” she said. “No wife would put up with someone spending all day Saturday at the OTB gambling on horses.”

“She might put up with it if she were into horse racing, too,” he replied, “but, you’re right -- I am single.”

“Confirmed bachelor?” she asked.

“Widower.”

“I’m so sorry. How? If you don’t mind me asking.”

“Auto accident ... drunk driver. It was about five years ago.”

“It must have been heartbreaking.”

“It was. At least she didn’t suffer. Her car was T-boned at a high rate of speed. It was instant -- she never knew what hit her.”

`’Do you have any children?” she asked.

“No children. By the way, she loved horse racing.”

“I’ve never bet on a horse race,” Sierra said.

“Tell you what -- instead of a tip, you pick a horse and I’ll bet your tip on it. You can keep the winnings.”

She scanned the paper and pointed to a name. “That one.”

“Cuppa Coffee? A filly in the fifth race...”

“Why shouldn’t a barista bet on a horse named Cuppa Coffee?” she asked. “Especially a lady horse?”

“Well -- it’s your tip. Cuppa Coffee is apt to be a long shot.” Glenn made a note on the paper and checked his watch. “I’d better head over there,” he said gulping his coffee. “I don’t want to miss the first race.” He handed her his credit card. “Run this through.”

She picked up the check. “I’ll be right back.”

Glenn signed the slip and swigged down the last in his mug. “I’ll let you know how Cuppa Coffee does.”

He drove across town the Off Track Betting parlor. His first race pick came in second, with relatively short odds. By the fourth race he was down twelve bucks when his pick came in first paying four-to-one, two-to-one and three-to-two, putting him ahead three dollars.

Glenn placed his bets on the fifth race and was about to walk away from the window when he remembered Sierra’s bet. “Two dollars on Cuppa Coffee to win,” he told the clerk and was handed his ticket.

He stood by the video display to watch as the horses were loaded into the starting gate. A glimpse at the totalizer showed the odds -- Cuppa Coffee was at fifty-one to one. Sierra just lost her tip, he thought.

He watched the display as the gates opened. Cuppa Coffee left her gate and followed the pack by about a length and stayed there through the first turn. In the back stretch she found her steam and began moving up on the outside. Through the second turn she was about a length behind the lead horse and continuing to move up. “Come on, Cuppa!” Glenn shouted. The photo finish showed Cuppa Coffee crossing the line first by a nose.

Glenn punched the air. “YES!” he shouted and headed for the window. The totalizer showed the final payout at fifty-three to one. He collected Sierra’s winnings, nearly forgetting his own pick had come in third, paying five-to-two on his show bet.

By the final race Glenn’s luck had improved somewhat and he was twenty-two to the good. He placed his final bet -- eleven to win on a chestnut gelding with twenty-three-to-one odds. This horse also left the gate a length behind the pack and that’s where he finished. Glenn tore up his ticket and threw it in the trash.

Glenn headed back to the coffee shop and saw Sierra chatting up another customer. He caught her eye and she headed toward him. He handed her the wad of bills comprising her winnings. “Cuppa Coffee was a good choice,” he said. “I should’ve bet on her, too. She finished first paying fifty-three-to-one. I don’t know what sweet nothings her jockey was whispering into her ear, but she found herself on the back stretch and won by a nose.”

Sierra counted the bills. “There’s a hundred and eight here.”

“Yup. At fifty-three-to-one, two bucks pays one-oh-six ... plus your two dollars back.”

“I’m beginning to see the appeal of your hobby, Glenn.”

“Believe me, this sort of thing doesn’t happen often. In parimutuel betting, you’re betting against the other bettors. Cuppa paid fifty-three-to-one because most of the bettors were betting on other horses. I won a big payout only once on a long shot -- I was about ten bucks to the good by the final race, so I put five on a thirty-to-one long shot who came in first. I collected a hundred fifty from that bet. This sort of thing is what makes horse racing exciting.”

“How did you do today?” she asked.

“I’m ahead about ten bucks. At least I didn’t lose money, which is my objective -- to have some fun and not lose money.”

Sierra riffled through the bills. “I still can’t believe this,” she said.

“Keep it -- it’s yours. Tell your boss I tipped you two bucks.”

“Glenn -- I am the boss. I own the place.”

“You own it? I thought Wilma was the boss.”

“She likes to think she is. I bought the place with an inheritance from my grand-parents. Wilma worked for the previous owners and I kept her on.” She held up the bills. “This will come in handy, believe me.”

He looked into her gray eyes and then scanned her. She wore a short-sleeved dress and a brown apron embroidered with The Coffee Spot and the shop logo. He followed her left arm down, pausing on a rose tattoo on her left forearm and then to her hand, noticing no ring.

“Sierra ... could I take you out to dinner tonight -- to celebrate your winnings?”

“I’m flattered, Glenn,” she replied. “I can’t. Jack and I are going to the ball game.”

“Jack is your...”

“He’s my son. He’s eleven, turning twelve in a couple months.” She took her phone from her back pocket and manipulated the screen. “This is Jack -- short for Jackson. When he was born I thought I wanted to be an artist and Jackson Pollack was one of my favorite painters.”

“Dribbler more than painter,” he remarked. “I can see your face in his -- good looking kid. What about Jack’s dad?”

“He’s ... out of the picture. Jack’s the happy outcome of a foolish relationship I had during my teen years.”

Glenn performed some mental arithmetic. “So, you’re ... twenty-nine ... ish?”

“That’s right, twenty-nine.”

“Twenty-nine and owning your own business. You’re doing good, Sierra.”

“Thanks.”

“I’m thirty-six and I never owned a business.”

“You never told me what you do,” she said.

“I’m a software engineer. I work for Allied Bank.”

“Sounds like good steady work,” she said.

“Steady and then some,” he replied.

“Jack and I are going to the zoo tomorrow. In lieu of a rain check for dinner, maybe you’d like to tag along for a family outing.”

“I’d love to do that, Sierra. Just tell me time and place.”

“Noon and right here.”

“Meet you here?” he asked. “Shop’s closed on Sunday.”

She smiled. “In order to buy the business I had to buy the building. There are three apartments upstairs -- a two bedroom, a one bedroom and a studio. Jack and I live in the two-bedroom and I rent out the others. The shop pays the mortgage and keeps the lights on, and the rentals pay the bills and put groceries on the table. Just go in the side door. We’re in apartment A.”

“Got it. Nothing like living above the store.”

“A word of warning -- Jack’s a good boy but he’s a little ... different.”

“Different? How?”

“You’ll find out. I just hope he doesn’t embarrass me too badly.”

“I doubt it,” Glenn replied. “I’m a pretty accepting guy.”

“See you tomorrow,” she said and placed her hand on his. He looked into her eyes and held his gaze for a long moment. “I have other customers, so if you’ll excuse me...”


Glenn parked by the curb in front of Sierra’s closed coffee shop. He went to the side of the building and found a wooden exterior door with a frosted light. Along-side of it were four doorbell buttons labeled Shop and Apartments A-C. He pressed the button for Apartment A. With a buzz and a snap the door unlocked and he opened it.

It opened onto a hallway, at the end of which was a back entrance into the coffee shop. To the side was a wooden stairway, the paint on the treads worn off by years of foot traffic. Glenn climbed the stairs and found himself in a hallway running the breadth of the building. To the front was a door with a brass letter A on it. To the rear were two doors marked B and C. He rang the bell for apartment A.

The deadbolt turned and the door opened. Glenn recognized Jack’s face from Sierra’s photo of him. Today the boy was wearing girls’ clothing -- a printed blouse, a denim skort that came a couple inches above his knees and sandals. Blue nail polish was on his finger and toenails. His hair was cut in a medium unisex way, over his ears but above collar length.

“Hi. You must be Jack. I’m Glenn.”

“Please call me Jackson,” the boy replied. “It’s my name. I don’t like being called Jack.”

“Okay, Jackson. Your mom is expecting me.”

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