The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 11

Romantic Sex Story: Chapter 11 - 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  

“My dad sent me a new Bourbon,” Sierra said, “want to try it out?”

“Make mine a short one,” Glenn replied, “the clock change always does a number on my routine. I’m afraid too much Bourbon would knock me out.”

“I know. We have to take down the Halloween decorations in the shop and put up Thanksgiving ones.” She handed him a glass and sat beside him on the sofa.”

“I just hate driving home in the dark.” He took a sip. “Well, my lease is finally done. I just need to wait for the property management to refund my security deposit. I did make the first deposit in our reserve fund.”

“We should start thinking about our wedding,” Sierra said.

“What do you have in mind? If you’re going to balk at a four-figure engagement ring, I don’t know how you’d go for a five-figure wedding ceremony.”

“I absolutely would not,” she replied. “A simple ceremony at City Hall.” She sipped from her glass. ““That’s all I want or need. I told my folks about us and they’re absolutely delighted.”

“You waited until now to tell them?”

“They were on a month-long eco-tourism trip to Costa Rica and just got back. They want to visit us over the holidays. Maybe that would be a time to schedule a wedding service. They could attend. What about your family?”

“I’m alone in the world,” he replied. “My parents are both dead and I don’t have siblings. I think a holiday ceremony with your folks would be just right.”

“It just flashed on me ... Where can they stay? Last time they came up to visit I let them use my room and I slept on the sofa. With you in the picture, what can we do? Put them in Jackie’s room and have her sleep on the sofa?”

“There are things called hotels,” he replied and drained his glass. “Well, we should turn in.”

Glenn headed to the bedroom, stripped to his briefs, slid under the covers and waited for Sierra to perform her nightly routine.

She stepped in wearing a knee-length flannel robe. Sierra slipped out of the robe. Underneath she had on a sheer light gray bra and matching briefs.

“Ooo-la-la,” Glenn remarked. “Those really show off your assets.”

“Do you mean this asset?” She turned around, leaned over and wiggled her hips.

“A thong. Outstanding. Is that new?”

“No -- I bought it years ago to please another fella, but we broke up before I could wear it. I had forgotten about it until I found it in my drawer. It still had the tags on it.”

“So, it’s a virgin.” Glenn lifted the covers. “Come into my parlor, said the spider to the fly.”

Sierra slid into bed. They faced each other and began kissing deep and passionate kisses. Glenn hooked one shoulder strap and slid it down her arm, revealing her breast. “Did I ever tell you how much I love your pinks and tans and how they decorate your bosom?”

“I believe you have at least once,” she replied sweetly.

Glenn leaned in to kiss her nipple. Suddenly the doorbell began ringing frantically. “What the hell?” he asked.

Sierra pulled up her shoulder strap and peered out the window. “It’s a police squad car,” she said and slipped back into her robe and slippers. She headed down the stairs with Glenn following in his robe.

“Police, ma’am,” the officer said as she opened the side door. “We’re here on a welfare check on one Marge Lipscomb, in apartment C. Her daughter called -- she didn’t show up for work this morning and her daughter has been unable to reach her.”

“I’m the landlord -- I own the building,” Sierra said. “I can let you in.”

Two officers followed them up the stairs. Sierra retrieved a keyring from her kitchen and unlocked the door to the studio apartment.

The officers stepped inside. One returned shortly. “There’s a deceased subject inside,” he informed Sierra.

“Oh, my God!”

“It looks like natural causes but we’ll need to call in the medical examiner and notify next of kin. We may be here for a while.”

Glenn followed Sierra back into their apartment. “It looks like you need a stiff drink,” he said.

“I’m shaking... “ Glenn poured her one. “Poor Marge. She’s been in that apartment since before I bought the place.”

“Both your tenants are so quiet I hardly know they’re here.”

“It’s just the shock.” She sipped her drink. “I’m starting to calm down ... Glenn -- I don’t want to sound mercenary, but with that apartment empty we lose four hundred a month in rental income.”

“That’s no problem,” he replied, “I’ll simply divert four hundred a month from our reserve fund to our day-to-day. We’ll still be building a reserve, just not quite as fast.”

“We’ll need to put it back on the market but I doubt we can get the rent we need in the shape it’s in. We’ll need to renovate it and that’s going to be an investment we can’t afford.”

“Let’s not worry about it now, with the holidays coming up. I can carry the loss in revenue until we figure out what to do.” He held her as they sat together on the sofa. In the hallway they could hear the authorities talking and moving equipment.

“One thing,” Glenn suggested, “we can do is to put your folks in that apartment when they come visit. It’s perfect -- it has a kitchen, private bath and sleeping quarters.”

“We’d need to spruce it up,” she replied, “at least some cleaning and painting.”

“Jackie and I can deal with that. Do we own the furniture?”

“Yes. Both apartments were rented furnished.”

A knock came on the door. Sierra opened it with Glenn standing behind her. “We’re done here. We’re transporting the body to the morgue. There’s no sign of foul play. I’d like your contact information. I’m sure the next of kin will want to go through the apartment for personal effects.”

Sierra stepped away from the door and returned with a business card. “I run the coffee shop downstairs,” she said. “I’m always around.”

The officers headed down the stairs and the door to apartment B cracked open. An older woman in a long flannel nightgown stepped into the hallway. “Sierra -- what’s going on?”

“Oh, Alma, something terrible. Marge has passed away.”

“Oh, no.”

“The cops were here on a welfare check,” Sierra continued. “They found her on the floor.”

“Marge was such a sweet soul,” Alma replied. Her gaze met Glenn’s. “I don’t think we’ve met.”

“Alma, this is Glenn, my fiance. Glenn, Alma rents the one-bedroom with her partner Elsie.”

“Pleased to meet you,” Glenn said.

“Fiance? This must have been fairly recent.”

“Since summer,” Sierra replied.

“So that explains the car that started parking in your spot. I thought maybe you had sprung for one.”

“No, it’s mine,” Glenn replied.

“Have you set a date?”

“We thought maybe over the holidays, a simple ceremony at City Hall.”

“That sounds sensible. No need to pay for a big, overblown event. Well, good night, you two. Congratulations and so sorry to hear about Marge.”

Alma headed back into apartment B. “I’m going to make sure everything is locked up,” Sierra said. “Be right in.”

Glenn slipped back into bed. Sierra entered, slipped out of her robe and joined him. “I have lost the mood,” she said as she snuggled against him. “I don’t think even your voodoo can recover it.”

“I lost the mood, too. How about a backrub?”

“Mmm...” She rolled onto her stomach and Glenn began stroking her back.

“I think we can lose this,” he said as he unhooked her bra back-strap. “We’ll save this outfit for a make-good. I think it has potential.”

Sierra slid her arms out of the straps and set her bra on the foot of the bed. Glenn resumed making full-length strokes on her back. “Mmm,” she purred. “Keep this up and I’ll be asleep in no time.”


Sierra set a cup of coffee in front of Glenn. He sat at his usual table in the shop and studied his Racing Form.

She sat at the table across from him. “One thing good about being engaged to the owner,” he remarked, “free, unlimited refills.”

“Anything promising at the track?” she asked.

“A couple races look interesting.”

“You do remember we need to take Jackie and Marcus to that Melonheads concert tonight.”

“Shit -- I forgot.”

“How can you forget? Jackie’s been bouncing off the ceiling anticipating tonight.”

“That’s right,” he replied, “the concert’s at seven but Carla wants us to meet at the theatre at five. She has our backstage passes and tickets. That means I’ll probably miss the last three races.”

“The sacrifices parents make for their kids,” Sierra remarked with a smirk.

“I had an idea about the apartment. We can look it over tomorrow while the shop is closed and see what renovations we need. Then we should rent it out short-term.”

“Short-term? As in, like an Air-BNB?”

“Exactly. I’ll bet we could get a hundred a night for it.”

“Why would someone want to rent that studio?” she asked.

“We’re in a nice part of town, close to services. We’re not far from the State University. We have off-street parking, the room has a kitchen, full bath, bed and sitting area. Plus, we could offer free continental breakfasts here in the shop from open to close.”

“I don’t know if I want to take on something like that,” she replied. “With a lease, it’s turn-key income.”

“If we could rent it on average for five nights a month, we’ll be a hundred a month ahead of what Marge was paying. I think we could get more business than that. A lot more. Plus, we could have it for ourselves when we have out-of-town guests.”

“You say ‘we’ like I have a mouse in my pocket. Sounds like a lot of work that yours truly would be doing and it’s not like I’m sitting on my hands all day.”

“We’d get Jackie to help out. Worth considering.” He gulped the last of the coffee. “I’m off to the OTB. Don’t worry -- I’ll be home in time for the concert.”

“Remember we also need to pick up Marcus on the way. He lives in the other direction.”

Glenn drove to the OTB parlor. He did well with the first four races but lost all his bets on the fifth and sixth. He was about to place his bets on the seventh when the proceedings were delayed due to an officiating dispute. He looked at his watch and decided he needed to head back to the shop.

After parking in the lot he rang the bell for the apartment and saw Sierra. “I had James come in to cover,” she said. “We close at six on Saturday but I told him it was okay to lock the door at five-thirty if there wasn’t any business. It’s usually pretty dead by this time.”

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