The Coffee Shop - Cover

The Coffee Shop

Copyright© 2019 by Unca D

Chapter 5

Romantic Sex Story: Chapter 5 - 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 drove toward the coffee shop. “The anesthetic is wearing off,” Jackie said.

“Does it hurt?” Sierra asked.

“It feels itchy.”

“Try not to disturb it. Dr Langley said you may feel some discomfort for a few days.”

“Mom -- can I get a wig?”

“A wig?”

“Yeah -- so I can have long hair.”

“You have perfectly good hair. We’ll let it grow and it’ll be at your shoulders in no time.”

He parked behind the shop and the three went upstairs. Sierra unlocked her apartment and they headed inside.

“Let’s see you try on what we bought tonight,” Glenn suggested.

“Okay...” Jackie modeled a skirt with two different tops and a floral dress.

“They all look good on her,” Sierra said.

“She does make a cute girl.”

Jackie headed for her room and returned wearing the cropped top and matching culottes. “May I wear this out, now?” she asked.

“No!” Sierra said emphatically.

“Why not? I’m a full-time girl now. This is my favorite.”

“Why do you like it so much?” Glenn asked.

“Because I feel most like a girl in it.”

“No child of mine, boy or girl, is going out on the street with a belly button showing.”

“Aww ... When I’m sixteen?”

“By then I hope you’ll have grown out of it. You may wear it in the apartment and you may wear it to bed. Speaking of which...”

“Yes, Mom ... I’ll get ready.”

Jackie headed for the bathroom and returned to the living room. “Good night, Mom,” she said.

“Good night. Did you thank Glenn for the clothes and for paying for your procedure?”

“Thank you, Glenn,” Jackie said and hugged him.

“You’re welcome, Jackie. I love you.”

“I love you, too. Goodnight.”

“Remember -- lights out at nine.”

Jackie headed for her room and closed the door. Sierra opened her cabinet and surveyed her collection of Bourbon. “Tonight calls for something special...” She selected a bottle and took two glasses into the kitchen for ice. Then she poured two servings. “This is a cask-strength, straight, four-year product from a craft distillery in Kentucky.”

Glenn sipped his. “Wow -- this is strong.”

“I like to let the ice melt a little,” she said. “It softens it and the flavors open up.”

“What will you do while that happens?” he asked.

“I have an idea.” She sat on his lap and kissed his lips. “You are staying the night, aren’t you?” She loosened his tie and unbuttoned his collar.

He held up his glass. “After this I’ll have no choice.”

“You can hold your liquor better than that.” She kissed his lips again.

“Actually I was anticipating this and packed an overnight bag. It’s in my trunk. I’ll go get it.”

“Plenty of time for that.” She kissed him passionately, driving her tongue into his mouth.

Glenn ran his hand along her slender legs. “Your legs feel extra smooth tonight.”

“I shaved them this morning. They were getting kinda gross.” Sierra sipped from her glass. “This is about right, now.”

He sipped from his. “I see what you mean. It’s a lot smoother. Straight from the bottle it’s like drinking rocket fuel.”

“Mmm ... I’m feeling it already. Feels really good.”

“I’m feeling it more than usual myself,” he said. “I have to be careful. I’m reaching the age when too much alcohol can impair my performance.” He stroked her face. “I suspect that alcohol improves your performance.”

She kissed his lips. “I love making love with a buzz on.”

Glenn drained his glass and set it on the end table. “That was potent but smooth and tasty,” he remarked.

Sierra emptied her glass and set it with his. “That is an expensive bottle,” she replied. “It set my dad back close to two hundred bucks. I only tap it for very special occasions.” She kissed his lips. “Like tonight.”

“Why don’t I go down and get my bag?” he asked.

“Okay -- I’ll start getting ready.”

Glenn headed down the stairs. He popped his trunk and retrieved a carry-on sized soft-sided bag and carried it upstairs and into the apartment, bolting the door behind him. He carried the bag into her bedroom, set it down and began stripping to his briefs.

“Sierra?” he called.

She stepped out of the bedroom’s closet wearing a floor-length nightgown in red. The spaghetti-strapped bodice was of sheer lace that barely concealed the twin charms of her bosom. The skirt was of a diaphanous gauze, open in the center from her navel to the floor and its hem lined with the same sheer lace. Under it she wore briefs made of the same sheer gauze and trimmed with the same lace. She had brushed her hair so it framed her face in casual curls and cascaded down her shoulders. “You like?”

“You look sensational. Where did you find that number?”

“On line,” she replied. “I do a lot of shopping on line. I can do it from the shop and I don’t need to figure out bus routes.”

He embraced her and kissed her lips. “You look absolutely beautiful. And the glasses complete the look.”

“I forgot I had them on.” She began to remove them.

“Leave them on,” Glenn replied. “When you’re downstairs with your hair up in a bun they make you look like a school-marm. Now you look like a sexy school-marm.”

“You like the look?”

He kissed her lips again. “I always wanted to bang a school-marm,” he said and scooped her off her feet, carried her to her bed and set her on it.

“I already set the clock,” she said.

He regarded the nightstand and saw no strip of condoms. Opening the drawer he looked in. “Where are the condoms?” he asked.

“I put them away. We won’t need them -- I also have an implant.” She lifted her left arm and pointed to a red spot on the inside of her biceps. “It’s a contraceptive implant.”

“When did you get that?” he asked as he lay beside her and caressed her face.

“I had my annual gyno appointment last week. I asked about going on the pill and my doctor suggested this. It lasts for three years -- and, my insurance covered it.”

“Three years?”

“Yes ... too bad Jackie’s only lasts one year. I was surprised the insurance covered it. I guess they’d rather pay for one implant than a whole string of pregnancies ... with pre-natal care and...” Glenn kissed her lips passionately and tenderly at the same time. “ ... and hospital expenses...” He kissed her again. “I am so horny,” she said. “I am so looking forward to not needing a condom ... not smelling like latex...”

He covered her face with kisses. “So am I. You look so pretty in that gown, it’s a shame to take it off.”

“I like foreplaying in lingerie,” she replied. “I like how it makes me feel sexy. But I prefer coupling in the nude.”

He began covering her upper chest with kisses. “That’s a formula I can get behind.”

“I want to savor tonight,” she said. “I feel like a virgin.”

“Any time you want to be a virgin, just say the word,” he replied.

“Then, I’m a virgin tonight. Be gentle with me ... but, not too gentle.”

“Let’s try this...” He sat up, resting against her headboard and coaxed her to sit between his legs and snuggle her back against his chest. He held her around her waist and kissed her shoulders.

“I like this,” she said. “I like how you’re holding me -- the closeness -- and I like your kisses.” He crossed his wrists and cupped his hands over her breasts. “Your hands are warm. Feels nice.”

Glenn began languidly fondling her nipples. They firmed under the lace of her gown’s bodice. Sierra drew in a breath and released it slowly. She began making soft, happy murmurs as he pinched and rolled her firmly erect nipples.

She ran her hands along his thighs. “You have nice legs,” she said and gripped them. “God, this feels so good,” she purred.

Glenn hooked his fingers under her shoulder straps and slid them down her arms. He resumed fondling her firm, fleshy nipples, skin on skin. Her heart was beating faster and he could feel it under her left breast.

She rolled off to the side and onto her back. Glenn lay atop her, pressing his hip against her mons and firmly caressing her breasts, using a milking motion from back to front.

Sierra’s lips parted, she half closed her eyes and rolled her face to one side. He could feel her belly twitching. “I love how you foreplay,” she said. “Your pacing is perfect ... your touch is perfect ... mmm ... I’m feeling it in my womb, Glenn. You’re making my womb throb.”

“Did I ever tell you how pretty your breasts and sexy your nipples are?”

“Once or twice.”

“I want to see how firm and tall I can make those nipples be.” He began sucking her right nipple and tugging it with his lips. “Look at that...” He repeated with her left nipple. “They look so sexy.” He began nursing her right breast. “Your hard nipple feels so good on my tongue,” he remarked and then drew her flesh into his mouth.

Sierra held his head and ran her fingers through his hair. She began making soft murmurs as she caressed his face. “Switch sides,” she whispered.

Glenn nursed her left breast, his hip still pressed against her mons. Sierra rocked her hips, pressing hard against his hip, and her thighs twitched.

Sierra released her grip on his head. “Make me come,” she said.

Glenn folded open the long skirt of her gown and smoothed his hand along her legs from her ankles to her thighs. “I love those long, slender, sleek legs,” he said as he savored the shapes of her calves. “You have the cutest knees.”

He caressed her thighs and hips. Then he grasped the waistband of her briefs. Sierra lifted her buttocks off the bed and he slid them off of her. “That pussy is extra smooth tonight, too,” he said.

“I shaved it this morning, too.”

“You were planning on today being special?”

“You know I like to be prepared.”

Glenn covered her mons and labia with kisses. He ran his lips along her smooth skin. Parting her labia with his fingers he kissed and licked her slit and savored her scent. Then he began a rapid back-and-forth with the tip of his tongue against her clitoral hood using the lightest of pressure.

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